US2007073056A1PendingUtilityA1
4-Substituted Pyrazoline Compounds, their Preparation and Use as Medicaments
Est. expiryJul 15, 2025(expired)· nominal 20-yr term from priority
A61P 35/00A61P 9/00A61P 5/00A61P 7/00A61P 37/02A61P 3/04A61P 43/00A61P 37/00A61P 25/04A61P 25/36A61P 25/06A61P 25/00A61P 29/00A61P 25/18A61P 25/34A61P 27/06A61P 3/10A61P 25/22A61P 25/30A61P 25/08A61P 25/14A61P 25/16A61P 25/32A61P 25/20A61P 3/00A61P 25/24A61P 29/02A61P 25/28A61P 25/02A61P 1/00A61P 19/00A61P 17/02A61P 11/00A61P 1/12A61P 17/00A61P 15/00A61P 17/04A61P 1/14A61P 19/10A61P 11/06A61P 19/08A61P 1/08C07D 409/04C07D 231/54C07D 401/12C07D 403/12C07D 231/06A61K 31/415
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Claims
Abstract
The present invention relates to 4-substituted pyrazoline compounds, methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans and animals.
Claims
exact text as granted — not AI-modified1 . A 4-substituted pyrazoline compound of general formula I,
wherein
X is O or S;
R 1 and R 2 , independently of one another, in each case represent an unsubstituted or at least mono-substituted aryl or heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system;
or a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bridged by at least one unsubstituted or at least mono-substituted alkylene group;
R 3 an unsubstituted or at least mono-substituted aryl or heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system;
a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bridged by at least one unsubstituted or at least mono-substituted alkylene group;
a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical which together with a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical forms a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing spirocyclic residue via a common ring atom;
a —O—R 6 moiety; a —NR 7 R 8 moiety or a —NR 9 —O—R 10 moiety;
R 4 represents F; Cl; Br; I; —CN; —NO 2 ; —NC; —OH; —NH 2 ; —SH; —C(═O)—H; —C(═O)—OH; —C(═O)—OR 17 ;
a saturated or unsaturated, unsubstituted or at least mono-substituted aliphatic radical;
a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted alkylene group, alkenylene group or alkinylene group and/or may be bridged by at least one unsubstituted or at least mono-substituted alkylene group:
an unsubstituted or at least mono-substituted aryl or heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an optionally at least mono-substituted alkylene group, alkenylene group or alkinylene group;
a —O—R 11 moiety; a —S—R 12 moiety; a —NH—R 13 moiety or a —NR 14 R 15 moiety;
R 5 represents H; F; Cl; Br; I; —CN; —NO 2 ; —NC; —OH; —NH 2 ; —SH; —C(═O)—H; —C(═O)—OH; —C(═O)—OR 17 ;
a saturated or unsaturated, unsubstituted or at least mono-substituted aliphatic radical;
a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted alkylene group, alkenylene group or alkinylene group and/or may be bridged by at least one unsubstituted or at least mono-substituted alkylene group;
an unsubstituted or at least mono-substituted aryl or heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted alkylene group, alkenylene group or alkinylene group;
a —O—R 11 moiety; a —S—R 12 moiety; a —NH—R 13 moiety or a —NR 14 R 15 moiety;
or R 4 and R 5 together with the bridging carbon atom form a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical;
R 6 represents a hydrogen atom;
a saturated or unsaturated, unsubstituted or at least mono-substituted aliphatic radical;
a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted alkylene group, alkenylene group or alkinylene group and/or may be bridged by at least one unsubstituted or at least mono-substituted alkylene group;
an unsubstituted or at least mono-substituted aryl or heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted alkylene group, alkenylene group or alkinylene group;
a —P(═O)(OR 16 ) 2 moiety; a —C(═O)—OR 17 moiety; a —C(═O)—NH—R 18 moiety or a —C(═O)—R 19 moiety;
R 7 and R 8 , independently of one another, in each case represent a hydrogen atom;
a saturated or unsaturated, unsubstituted or at least mono-substituted aliphatic radical;
a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted alkylene group, alkenylene group or alkinylene group and/or may be bridged by at least one unsubstituted or at least mono-substituted alkylene group;
a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical which together with a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical forms a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing spirocyclic residue via a common ring atom;
an unsubstituted or at least mono-substituted aryl or heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted alkylene group, alkenylene group or alkinylene group;
a —P(═O)(OR 16 ) 2 moiety; a —C(═O)—OR 17 moiety; a —C(═O)—NH—R 18 moiety; a —C(═O)—R 19 moiety; a —S(═O) 2 —R 20 moiety; or a —NR 21 R 22 moiety;
R 9 represents hydrogen or a saturated or unsaturated, unsubstituted or at least mono-substituted aliphatic radical;
R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R20, independently of one another, in each case represent a saturated or unsaturated, unsubstituted or at least
mono-substituted aliphatic radical;
a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatorn as a ring member containing cycloaliphatic radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted alkylene group, alkenylene group or alkinylene group and/or may be bridged by at least one unsubstituted or at least mono-substituted alkylene group;
or an unsubstituted or at least mono-substituted aryl or heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted alkylene group, alkenylene group or alkinylene group;
R 16 , R 17 , R 18 and R 19 , independently of one another, in each case represent a saturated or unsaturated, unsubstituted or at least mono-substituted aliphatic radical,
or an unsubstituted or at least mono-substituted aryl or heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or m ay be bonded via an unsubstituted or at least mono-substituted alkylene group, alkenylene group or alkinylene group;
and
R 21 and R 22 , independently of one another, in each case represent a hydrogen atom;
a saturated or unsaturated, unsubstituted or at least mono-substituted aliphatic radical;
a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted alkylene group, alkenylene group or alkinylene group;
a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical which together with a saturated or unsaturated, unsubstituted or at least monosubstituted, optionally at least one heteroatom as a ring member containing cycloaliphatic radical forms a saturated or unsaturated, unsubstituted or at least mono-substituted, optionally at least one heteroatom as a ring member containing spirocyclic residue via a common ring atom;
or an unsubstituted or at least mono-substituted aryl or heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted alkylene group, alkenylene group or alkinylene group;
whereby the following compounds are excluded
[A] ethyl 4,5-dimorpholino-1-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylate,
[B] methyl 1-phenyl-4,5-di(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxylate,
[C] 1-(4-chlorophenyl)-4-(hydroxymethyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid,
[D] ethyl 5-morpholino-1,4-diphenyl-4,5-dihydro-1H-pyrazole-3-carboxylate,
[E] ethyl 4-(4-chlorophenyl)-1-(4-fluorophenyl)-5-morpholino-4,5-dihydro-1H-pyrazole-3-carboxylate,
[F] ethyl 1-(4-fluorophenyl)-5-morpholino-4-p-tolyl-4,5-dihydro-1H-pyrazole-3-carboxylate,
[G] methyl 4-(hydroxymethyl)-1-(2-(methoxycarbonyl)phenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylate,
[H] benzofuran-2-yl(5-(4-hydroxyphenyl)-4-nitro-1-(3-phenyl-1H-pyrazol-5-yl)-4,5-dihydro-1H-pyrazol-3-yl)methanone,
[I] (5-(benzo[d][1,3]dioxol-5-yl)-4-nitro-1-(3-phenyl-1H-pyrazol-5-yl)-4,5-dihydro-1H-pyrazol-3-yl)(benzofuran-2-yl)methanone,
[J] 3-(benzofuran-2-carbonyl)-5-phenyl-1-(3-phenyl-1H-pyrazol-5-yl)-1H-pyrazole-4,4(5H)-dicarbonitrile,
[K] (5-(benzo[d][1,3]didxol-4-yl)-4-nitro-1-(3-phenyl-1H-pyrazol-5-yl)-4,5-dihydro-1H-pyrazol-3-yl)(benzofuran-2-yl)methanone,
[L] ethyl 1-(3-methoxypheyl)-5-morpholino-4-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylate,
[M] ethyl 1-(3-methoxyphenyl)-4-phenyl-5-(piperazin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxylate, which is optionally bonded to copolystyrol,
[N] 1-(3-methoxyphenyl)-4-phenyl-5-(piperazin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid, which is optionally bonded to copolystyrol and
[O] ethyl 5-(4-oxo-2,3-diphenyl-4,5-dihydro-2H-pyrazolo[4,3-d]pyridazin-7-yl)-1,4-diphenyl-4,5-dihydro-1H-pyrazole-3-carboxylate,
optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding N-oxide thereof, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.
2 . A compound according to claim 1 , characterized in that
X is O or S; R 1 and R 2 , independently of one another, in each case represent an unsubstituted or at least mono-substituted 6- or 10-membered aryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system;
an unsubstituted or at least mono-substituted 5- to 14-membered heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system;
an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical or C 4-16 cycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group;
or an unsubstituted or at least mono-substituted C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group;
R 3 represents an unsubstituted or at least mono-substituted 6- or 10-membered aryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system;
an unsubstituted or at least mono-substituted 5- to 14-membered heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system;
an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical or C 4-16 cycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group;
an unsubstituted or at least mono-substituted C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group,
an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical, C 4-16 cycloalkenyl radical, C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical which together with an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical, C 4-16 cycloalkenyl radical, C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical forms an unsubstituted or at least mono-substituted spirocyclic residue via a common ring atom;
a —O—R 6 moiety; a —NR 7 R 8 moiety or a —NR 9 —O—R 10 moiety;
R 4 represents F; Cl; Br; I; —CN; —NO 2 ; —NC; —OH; —NH 2 ; —SH; —C(═O)—H; —C(═O)—OH; —C(═O)—OR 17 ;
an unsubstituted or at least mono-substituted C 1-16 alkyl radical, C 2-16 alkenyl radical or C 2-16 alkinyl radical;
an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical or C 4-16 cycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group;
an unsubstituted or at least mono-substituted C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group;
an unsubstituted or at least mono-substituted 6- or 10-membered aryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
or an unsubstituted or at least mono-substituted 5- to 14-membered heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
a —O—R 11 moiety; a —S—R 12 moiety; a —NH—R 13 moiety or a —NR 14 R 15 moiety;
R 5 represents H; F; Cl; Br; I; —CN; —NO 2 ; —NC; —OH; —NH 2 ; —SH; —C(═O)—H; —C(═O)—OH; —C(═O)—OR 17 ;
an unsubstituted or at least mono-substituted C 1-16 alkyl radical, C 2-16 alkenyl radical or C 2-16 alkinyl radical;
an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical or C 4-16 cycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group;
an unsubstituted or at least mono-substituted C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group;
an unsubstituted or at least mono-substituted 6- or 10-membered aryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
or an unsubstituted or at least mono-substituted 5- to 14-membered heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
—O—R 11 moiety; a —S—R 12 moiety; a —NH—R 13 moiety or a —NR 14 R 15 moiety;
or R 4 and R 5 together with the bridging carbon atom form an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical or C 4-16 cycloalkenyl radical; R 6 represents a hydrogen atom;
an unsubstituted or at least mono-substituted C 1-16 alkyl radical, C 2-16 alkenyl radical or C 2-16 alkinyl radical;
an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical or C 4-16 cycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
an unsubstituted or at least mono-substituted C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
an unsubstituted or at least mono-substituted 6- or 10-membered aryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
an unsubstituted or at least mono-substituted 5- to 14-membered heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
a —P(═O)(OR 16 ) 2 moiety; a —C(═O)—OR 17 moiety; a —C(═O)—NH—R 18 moiety or a —C(═O)—R 19 moiety;
R 7 and R 8 , independently of one another, in each case represent a hydrogen atom;
an unsubstituted or at least mono-substituted C 1-16 alkyl radical, C 2-16 alkenyl radical or C 2-16 alkinyl radical;
an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical or C 4-16 cycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
an unsubstituted or at least mono-substituted C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical, C 4-16 cycloalkenyl radical, C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical which together with an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical, C 4-16 cycloalkenyl radical, C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical forms an unsubstituted or at least mono-substituted spirocyclic residue via a common ring atom;
an unsubstituted or at least mono-substituted 6- or 10-membered aryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
an unsubstituted or at least mono-substituted 5- to 14-membered heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least monosubstituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
a —P(═O)(OR 16 ) 2 moiety; a —C(═O)—OR 17 moiety; a —C(═O)—NH—R 18 moiety; a —C(═O)—R 19 moiety; a —S(═O) 2 —R 20 moiety; or a —NR 21 R 22 moiety;
R 9 represents a hydrogen atom or an unsubstituted or at least mono-substituted C 1-16 alkyl radical, C 2-16 alkenyl radical or C 2-16 alkinyl radical; R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 20 , independently of one another, in each case represent an unsubstituted or at least mono-substituted C 1-16 alkyl radical, C 2-16 alkenyl radical or C 2-16 alkinyl radical;
an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical or C 4-16 cycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
an unsubstituted or at least mono-substituted C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bridged by at least one unsubstituted or at least mono-substituted C 1-5 alkylene group and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
an unsubstituted or at least mono-substituted 6- or 10-membered aryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
or an unsubstituted or at least mono-substituted 5- to 14-membered heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
R 16 , R 17 , R 18 and R 19 , independently of one another, in each case represent an unsubstituted or at least mono-substituted C 1-16 alkyl radical, C 2-16 alkenyl radical or C 2-16 alkinyl radical;
or an unsubstituted or at least mono-substituted 6- or 10-membered aryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
or an unsubstituted or at least mono-substituted 5- to 14-membered heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
and
R 21 and R 22 , independently of one another, in each case represent a hydrogen atom;
an unsubstituted or at least mono-substituted C 1-16 alkyl radical, C 2-16 alkenyl radical or C 2-16 alkinyl radical;
an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical or C 4-16 cycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
an unsubstituted or at least mono-substituted C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical, which in each case may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical, C 4-16 cycloalkenyl radical, C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical which together with an unsubstituted or at least mono-substituted C 3-16 cycloalkyl radical, C 4-16 cycloalkenyl radical, C 4-16 heterocycloalkyl radical or C 5-16 heterocycloalkenyl radical forms an unsubstituted or at least mono-substituted spirocyclic residue via a common ring atom;
an unsubstituted or at least mono-substituted 6- or 10-membered aryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
or an unsubstituted or at least mono-substituted 5- to 14-membered heteroaryl radical, which may be condensed with an unsubstituted or at least mono-substituted mono- or polycyclic ring system and/or may be bonded via an unsubstituted or at least mono-substituted C 1-5 alkylene group, C 2-5 alkenylene group or C 2-5 alkinylene group;
whereby
the rings of the aforementioned ring system are in each case independently of one another 5- 6- or 7-membered and may in each case independently of one another optionally contain 1, 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulfur; the aforementioned heteroaryl radicals in each case optionally contain 1, 2, 3 or 4 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulfur as ring member(s); the aforementioned heterocycloalkyl radicals and heterocycloalkenyl radicals in each case optionally contain 1, 2, 3 or 4 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulfur as ring member(s); optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding N-oxide thereof, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.
3 . A compound according to claim 1 , characterized in that R 1 and R 2 , independently of one another, in each case represent a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl, isoindolyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzo[2,1,3]thiadiazolyl, [1,2,3]-benzothiadiazolyl, [2,1,3]-benzoxadiazolyl, [1,2,3]-benzoxadiazolyl, benzoxazolyl, benzthiazolyl, benzisoxazolyl, benzisothiazolyl, imidazo[2,1-b]thiazolyl, 2H-chromenyl, pyranyl, indazolyl, quinazolinyl, [1,3]-benzodioxolyl, [1,4]-benzodioxanyl, [1,2,3,4]-tetrahydronaphthyl, (2,3)-dihydro-1H-cyclopenta[b]indolyl, [1,2,3,4]-tetrahydroquinolinyl, [1,2,3,4]-tetrahydroisoquinolinyl, [1,2,3,4]-tetrahydroquinazolinyl and [3,4]-dihydro-2H-benzo[1,4]oxazinyl, which in each case is optionally bonded to the pyrazoline compound of general formula I via the aromatic or heteroaromatic part of the aforementioned radicals and may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , —CH 2 —Cl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , phenoxy and thiophenyl, whereby the thiophenyl radical can be substituted with 1, 2 or 3 substituents independently selected from the group consisting of F, Cl, Br, methyl, ethyl and n-propyl;
or a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, diazepanyl, azocanyl, (2,5)-dihydrofuranyl, (2,5)-dihydrothiophenyl, (2,3)-dihydrofuranyl, (2,3)-dihydrofuranyl, (2,5)-dihydro-1H-pyrrolyl, (2,3)-dihydro-1H-pyrrolyl, tetrahydrothiopyranyl, tetrahydropyranyl, (3,4)-dihydro-2H-pyranyl, (3,4)-dihydro-2H-thiopyranyl, (1,2,3,6)-tetrahydropyridinyl, (1,2,3,4)-tetrahydropyridinyl, (1,2,5,6)-tetrahydropyridinyl, [1,3]-oxazinanyl, hexahydropyrimidinyl, (5,6)-dihydro-4H-pyrimidinyl, oxazolidinyl, (1,3)-dioxanyl, (1,4)-dioxanyl, (1,3)-dioxolanyl, indolinyl, isoindolinyl, decahydronaphthyl, (1,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinolinyl, octahydro-cyclopenta[c]pyrrolyl, (1,3,4,7,9a)-hexahydro2H-quinolizinyl, (1,2,3,5,6,8a)-hexahydro-indolizinyl, decahydroquinolinyl, dodecahydro-carbazolyl, 9H-carbazolyl, decahydroisoquinolinyl, (6,7)-dihydro-4H-thieno[3,2-c]pyridinyl, (2,3)-dihydro-1H-benzo[de]isoquinolinyl, (1,2,3,4)-tetrahydroquinoxazlinyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl and norbornenyl, which in each case is optionally bonded to the pyrazoline compound of general formula I via the (hetero)cycloaliphatic part of the aforementioned radicals and may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—CH 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 .
4 . A compound according to claim 1 , characterized in that
R 3 represents a radical selected from the group consisting of (2,3)-dihydro-1H-cyclopenta[b]indolyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, diazepanyl, azocanyl, (2,5)-dihydrofuranyl, (2,5)-dihydrothiophenyl, (2,3)-dihydrofuranyl, (2,3)-dihydrofuranyl, (2,5)-dihydro-1H-pyrrolyl, (2,3)-dihydro-1H-pyrrolyl, tetrahydrothiopyranyl, tetrahydropyranyl, (3,4)-dihydro-2H-pyranyl, (3,4)-dihydro-2H-thiopyranyl, (1,2,3,6)-tetrahydropyridinyl, (1,2,3,4)-tetrahydropyridinyl, (1,2,5,6)-tetrahydropyridinyl, [1,3]-oxazinanyl, hexahydropyrimidinyl, (5,6)-dihydro-4H-pyrimidinyl, oxazolidinyl, (1,3)-dioxanyl, (1,4)-dioxanyl, (1,3)-dioxolanyl, indolinyl, isoindolinyl, decahydronaphthyl, (1,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinolinyl, octahydro-cyclopenta[c]pyrrolyl, (1,3,4,7,9a)-hexahydro-2H-quinolizinyl, (1,2,3,5,6,8a)-hexahydro-indolizinyl, decahydroquinolinyl, dodecahydrocarbazolyl, 9H-carbazolyl, decahydroisoquinolinyl, (6,7)-dihydro-4H-thieno[3,2-c]pyridinyl, (2,3)-dihydro-1H-benzo[de]isoquinolinyl, (1,2,3,4)-tetrahydroquinoxazlinyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, norbornenyl, 8-aza-bicyclo[3.2.1]octyl and 8-aza-spiro[4.5]decanyl, which may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —O—CH 2 —O—CH 3 , —O—CH 2 —CH 2 —O—CH 3 , —O—CH 2 —O—C 2 H 5 , —C(OCH 3 )(C 2 H 5 ) 2 , —C(OCH 3 )(CH 3 ) 2 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —C(═O)—OH, —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 , CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —O—-Benzyl, benzyl, cyclopentyl, cyclohexyl, pyrrolidinyl and piperidinyl; a —O—R 6 moiety; a —NR 7 R 8 moiety or a —NR 9 —O—R 10 moiety.
5 . A compound according to claim 1 , characterized in that
R 4 represents F; Cl; Br; I; —CN; —NO 2 ; —NC; —OH; —NH 2 ; —SH; —C(═O)—H; —C(═O)—OH; —C(═O)—OR 17 ; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl and 4-octyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of —OH, F, Cl, Br, I, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —CN and —NO 2 ; a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH-group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—CH 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ; a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl and diazepanyl, which may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, ——NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , and —N(C 2 H 5 ) 2 ; a —O—R 11 moiety; a —S—R 12 moiety, a —NH—R 13 moiety or a —NR 14 R 15 moiety.
6 . A compound according to claim 1 , characterized in that R 4 and R 5 together with the bridging carbon atom form a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and cyclooctenyl, which may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 .
7 . A compound according to claim 1 , characterized in that R 5 represents H; F; Cl; Br; I; —CN; —NO 2 ; —NC; —OH; —NH 2 ; —SH; —C(═O)—H; —C(═O)—OH; —C(═O)—OR 17 ;
a radical selected from the group consisting of methyl, —CF 3 , —CH 2 F, —CF 2 H, —C 2 F 5 , ethyl, —CH 2 —CN, —CH 2 —OH, n-propyl, isopropyl, —CH 2 —CH 2 —CN, —CH 2 —CH 2 —OH, n-butyl, —CH 2 —CH 2 —CH 2 —CN, —CH 2 —CH 2 —CH 2 —OH, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl and 3-hexyl; a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl and diazepanyl, a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl) and pyrrolyl, which may be bonded via a —(CH 2 )— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , F, Cl and Br; a —O—R 11 moiety; a —S—R 12 moiety, a —NH—R 13 moiety or a —NR 14 R 15 moiety.
8 . A compound according to claim 1 , characterized in that R 6 represents a hydrogen atom; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl vinyl, n-propenyl, n-butenyl, n-pentenyl, n-hexenyl, ethinyl, propinyl, n-butinyl, n-pentinyl and n-hexinyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of —OH, F, Cl, Br, I, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —CN, —NO, —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —NH—C(═O)—C(CH 3 ) 3 , —NH—C(═O)—O—CH 3 , —NH—C(═O)—O—C 2 H 5 , —NH—C(═O)—O—C(CH 3 ) 3 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C(CH 3 ) 3 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —C(═O)—OH, —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 , —C(═O)—CH 3 , —C(═O)—C 2 H 5 and —C(═O)—C(CH 3 ) 3 ;
a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, 8-aza-bicyclo[3.2.1]octyl and diazepanyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH-group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ; a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH-group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —O—C( 50 O)—CH 3 , —O—C(═O)—C 2 H 5 , —O—C(═O)—CH(CH 3 ) 2 , —O—C(═O)—CH 2 —CH 2 —CH 3 , —CH 2 —N(CH 3 ) 2 , —(CH 2 )—N(C 2 H 5 ) 2 , —CH 2 —N(C 3 H 7 ) 2 , —CH 2 —N(C 4 H 9 ) 2 , —CH 2 —N(CH 3 )(C 2 H 5 ) and —(CH 2 )-morpholinyl; a —P(═O)(OR 16 ) 2 moiety; a —C(═O)—OR1 17 moiety; a —C(═O)—NH—R 18 moiety or a —C(═O)—R 19 moiety.
9 . A compound according to claim 1 , characterized in that R 7 and R 8 , independently of another, in each case represent a hydrogen atom;
a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, 2-(6-methyl)-heptyl, 2-(5-methyl)-heptyl, 2-(5-methyl)-hexyl, 2-(4-methyl)-hexyl, 2-(7-methyl)-octyl; 2-(6-methyl)-octyl, vinyl, n-propenyl, n-butenyl, n-pentenyl, n-hexenyl, ethinyl, propinyl, n-butinyl, n-pentinyl and n-hexinyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of —OH, F, Cl, Br, I, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 ,—N(C 2 H 5 ) 2 , —CN and —NO 2 ; a radical selected from the group consisting of (1,2,3,4)-tetrahydronaphthyl, (2,3)-dihydro-1H-cyclopenta[b]indolyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, diazepanyl, azocanyl, (2,5)-dihydrofuranyl, (2,5)-dihydrothiophenyl, (2,3)-dihydrofuranyl, (2,3)-dihydrofuranyl, (2,5)-dihydro-1H-pyrrolyl, (2,3)-dihydro-1H-pyrrolyl, tetrahydrothiopyranyl, tetrahydropyranyl, (3,4)-dihydro-2H-pyranyl, (3,4)-dihydro-2H-thiopyranyl, (1,2,3,6)-tetrahydropyridinyl, (1,2,3,4)-tetrahydropyridinyl, (1 ,2,5,6)-tetrahydropyridinyl, [1,3]-oxazinanyl, hexahydropyrimidinyl, (5,6)-dihydro4H-pyrimidinyl, oxazolidinyl, (1,3)-dioxanyl, (1,4)-dioxanyl, (1,3)-dioxolanyl, indolinyl, isoindolinyl, decahydronaphthyl, (1,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinolinyl, octahydro-cyclopenta[c]pyrrolyl, (1,3,4,7,9a)-hexahydro-2H-quinolizinyl, (1,2,3,5,6,8a)-hexahydro-indolizinyl, decahydroquinolinyl, dodecahydro-carbazolyl, 9H-carbazolyl, decahydroisoquinolinyl, (6,7)-dihydro-4H-thieno[3,2-c]pyridinyl, (2,3)-dihydro-1H-benzo[de]isoquinolinyl, (1,2,3,4)-tetrahydroquinoxazlinyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, norbornenyl, 8-aza-bicyclo[3.2. 1]octyl and 8-aza-spiro[4.5]decanyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —O—CH 2 —O—CH 3 , —O—CH 2 —CH 2 —O—CH 3 , —O—CH 2 —O—C 2 H 5 , —C(OCH 3 )(C 2 H 5 ) 2 , —C(OCH 3 )(CH 3 ) 2 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH2—CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —C(═O)—OH, —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH3)2, —N(C 2 H 5 ) 2 , —O-Benzyl, benzyl, cyclopentyl, cyclohexyl, pyrrolidinyl and piperidinyl; a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyli, which may be bonded via a —(CH 2 )—, —(CH 2 ) —(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ; a —P(═O)(OR 16 ) 2 moiety; a —C(═O)—OR 17 moiety; a —C(═O)—NH—R 18 moiety; a —C(═O)—R 19 moiety; a —S(═O) 2 —R20 moiety; or a —NR 21 R 22 moiety.
10 . A compound according to claim 1 , characterized in that R 9 represents hydrogen or an alkyl radical selected from the group consisting of methyl, ethyl and n-propyl.
11 . A compound according to claim 1 , characterized in that R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 20 , independently of another, in each case represent a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, 2-(6-methyl)-heptyl, 2-(5-methyl)-heptyl, 2-(5-methyl)-hexyl, 2-(4-methyl)-hexyl, 2-(7-methyl)-octyl; 2-(6-methyl)-octyl, vinyl, n-propenyl, n-butenyl, n-pentenyl, n-hexenyl, ethinyl, propinyl, n-butinyl, n-pentinyl and n-hexinyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of —OH, F, Cl, Br, I, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —CN and —NO 2 ;
a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, 8-aza-bicyclo[3.2.1]octyl and diazepanyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )—or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(—O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N (C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(—O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ; or a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH2CH 3 , —O—CH(CH 3 ) 2 , —O—CH2—CH2—CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 .
12 . A compound according to claim 1 , characterized in that R 16 , R 17 , R 18 and R 19 , independently of one another, in each case represent a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, vinyl, n-propenyl, n-butenyl, n-pentenyl, n-hexenyl, ethinyl, propinyl, n-butinyl, n-pentinyl and n-hexinyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —NH—C(═O)—C(CH 3 ) 3 , —NH—C(═O)—O—CH 3 , —NH—C(═O)—O—C 2 H 5 , —NH—C(═O)—O—C(CH 3 ) 3 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C(CH 3 ) 3 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —OH, —C(═O)—OH, —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 , —C(═O)—CH 3 , —C(═O)—C 2 H 5 and —C(═O)—C(CH 3 ) 3 ;
or a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH,CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2, —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —O—C(═O)—CH 3 , —O—C(═O)—C 2 H 5 , —O—C(═O)—CH(CH 3 ) 2 , —O—C(═O)—CH 2 —CH 2 —CH 3 , —CH 2 —N(CH 3 ) 2 , —(CH 2 )—N(C 2 H 5 ) 2 , —CH 2 —N(C 3 H 7 ) 2 , —CH 2 —N(C 4 H 9 ) 2 , —CH 2 —N(CH 3 )(C 2 H 5 ) and —(CH 2 )-morpholinyl.
13 . A compound according to claim 1 , characterized in that R 21 and R 22, independently of another, in each case represent hydrogen;
a radical selected from the group consisting of methyl, ethyl, n-propyl, 5 isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, 2-(6-methyl)-heptyl, 2-(5-methyl)-heptyl, 2(5-methyl)-hexyl, 2-(4-methyl)-hexyl, 2-(7-methyl)-octyl; 2-(6-methyl)-octyl, vinyl, n-propenyl, n-butenyl, n-pentenyl, n-hexenyl, ethinyl, propinyl, n-butinyl, n-pentinyl and n-hexinyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of —OH, F. Cl, Br, I, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —CN and —NO 2 ; a radical selected from the group consisting of (2,3)-dihydro-1H-cyclopenta[b]indolyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, diazepanyl, azocanyl, (2,5)-dihydrofuranyl, (2,5)-dihydrothiophenyl, (2,3)-dihydrofuranyl, (2,3)-dihydrofuranyl, (2,5)-dihydro-1H-pyrrolyl, (2,3)-dihydro-1H-pyrrolyl, tetrahydrothiopyranyl, tetrahydropyranyl, (3,4)-dihydro-2H-pyranyl, (3,4)-dihydro-2H-thiopyranyl, (1,2,3,6)-tetrahydropyridinyl, (1,2,3,4)-tetrahydropyridinyl, (1,2,5,6)-tetrahydropyridinyl, [1,3]-oxazinanyl, hexahydropyrimidinyl, (5,6)-dihydro-4H-pyrimidinyl, oxazolidinyl, (1,3)-dioxanyl, (1,4)-dioxanyl, (1,3)-dioxolanyl, indolinyl, isoindolinyl, decahydronaphthyl, (1,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinolinyl, octahydro-cyclopenta[c]pyrrolyl, (1 ,3,4,7,9a)-hexahydro-2H-quinolizinyl, (1,2,3,5,6,8a)-hexahydro-indolizinyl, decahydroquinolinyl, dodecahydro-carbazolyl, 9H-carbazolyl, decahydroisoquinolinyl, (6,7)-dihydro-4H-thieno[3,2-c]pyridinyl, (2,3)-dihydro-1H-benzo[de]isoquinolinyl, (1,2,3,4)-tetrahydroquinoxazlinyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, norbornenyl, 8-aza-bicyclo[3.2.1]octyl and 8-aza-spiro[4.5]decanyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 3 , —O—C(CH 3 ) 3 , —O—CH 2 —O—CH 3 , —O—CH 2 —CH 2 —O—CH 3 , —O—CH 2 —O—C 2 H 5 , —C(OCH 3 )(C 2 H 5 ) 2 , —C(OCH 3 )(CH 3 ) 2 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —C(═O)—OH, —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , cyclopentyl, cyclohexyl, pyrrolidinyl and piperidinyl; or a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 ) —(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl,.n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2, —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 .
14 . A compound according to claim 1 , characterized in that
X is S or O; R 1 and R 2 , independently of one another, in each case represent a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl); thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl, isoindolyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzo[2,1,3]thiadiazolyl, [1,2,3]-benzothiadiazolyl, [2,1,3]-benzoxadiazolyl, [1,2,3]-benzoxadiazolyl, benzoxazolyl, benzthiazolyl, benzisoxazolyl, benzisothiazolyli imidazo[2,1-b]thiazolyl, 2H-chromenyl, pyranyl, indazolyl, quinazolinyl, [1,31-benzodioxolyl, [1,4]benzodioxanyl, [1,2,3,4]-tetrahydronaphthyl, (2,3)-dihydro-lH-cyclopenta[b]indolyl, (1 ,2,3,4]-tetrahydroquinolinyl, [1 ,2,3,4]-tetrahydroisoquinolinyl, [1,2,3,4]-tetrahydroquinazolinyl and [3,4] dihydro-2H-benzo[1,4]oxazinyl, which in each case is optionally bonded to the pyrazoline compound of general formula I via the aromatic or heteroaromatic part of the aforementioned radicals and may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , —CH 2 —Cl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(O) C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH3, —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , phenoxy and thiophenyl, whereby the thiophenyl radical can be substituted with 1, 2 or 3 substituents independently selected from the group consisting of F, Cl, Br, methyl, ethyl and n-propyl; or a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, diazepanyl, azocanyl, (2,5)-dihydrofuranyl, (2,5)-dihydrothiophenyl, (2,3)-dihydrofuranyl, (2,3)-dihydrofuranyl, (2,5)-dihydro-1H-pyrrolyl, (2,3)-dihydro-1H-pyrrolyl, tetrahydrothiopyranyl, tetrahydropyranyl, (3,4)-dihydro-2H-pyranyl, (3,4)-dihydro-2H-thiopyranyl, (1,2,3,6)-tetrahydropyridinyl, (1,2,3,4)-tetrahydropyridinyl, (1,2,5,6)-tetrahydropyridinyl, [1,3]-oxazinanyl, hexahydropyrimidinyl, (5,6)-dihydro-4H-pyrimidinyl, oxazolidinyl, (1,3)-dioxanyl, (1,4)-dioxanyl, (1,3)-dioxolanyl, indolinyl, isoindolinyl, decahydronaphthyl, (1,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinolinyl, octahydro-cyclopenta[c]pyrrolyli, (1,3,4,7,9a)-hexahydro-2H-quinolizinyl, (1,2,3,5,6,8a)-hexahydro-indolizinyl, decahydroquinolinyl, dodecahydro-carbazolyli, 9H-carbazolyl, decahydroisoquinolinyl, (6,7)-dihydro-4H-thieno[3,2-c]pyridinyl, (2,3)-dihydro-1H-benzo[de]isoquinolinyl, (1,2,3,4)-tetrahydroquinoxazlinyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl and norbornenyl, which in each case is optionally bonded to the pyrazoline compound of general formula I via the (hetero)cycloaliphatic part of the aforementioned radicals and may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2, —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ; R 3 represents a radical selected from the group consisting of (2,3)-dihydro-1H-cyclopenta[b]indolyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, diazepanyl, azocanyl, (2,5)-dihydrofuranyl, (2,5)-dihydrothiophenyl, (2,3)-dihydrofuranyl, (2,3)-dihydrofuranyl, (2,5)-dihydro-1H-pyrrolyl, (2,3)-dihydro-1H-pyrrolyl, tetrahydrothiopyranyl, tetrahydropyranyl, (3,4)-dihydro-2W-pyranyl, (3,4)-dihydro-2H-thiopyranyl, (1,2,3,6)-tetrahydropyridinyl, (1,2,3,4)-tetrahydropyridinyl, (1,2,5,6)-tetrahydropyridinyl, [1,3]-oxazinanyl, hexahydropyrimidinyl, (5,6)-dihydro-4H-pyrimidinyl, oxazolidinyl, (1,3)-dioxanyl, (1,4)-dioxanyl, (1,3)-dioxolanyl, indolinyl, isoindolinyl, decahydronaphthyl, (1 ,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinolinyl, octahydro-cyclopenta[c]pyrrolyl, (1,3,4,7,9a)-hexahydro-2H-quinolizinyl, (1,2,3,5,6,8a)-hexahydro-indolizinyl, decahydroquinolinyl, dodecahydro-carbazolyl, 9H-carbazolyl, decahydroisoquinolinyl, (6,7)-dihydro-4H-thieno[3,2-c]pyridinyl, (2,3)-dihydro-1H-benzo[de]isoquinolinyl, (1,2,3,4)-tetrahydroquinoxazlinyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, norbornenyl, 8-aza-bicyclo[3.2.1]octyl and 8-aza-spiro[4.5]decanyl, which may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —O—CH 2 —O—CH 3 , —O—CH 2 —CH 2 —O—CH 3 , —O—CH 2 —O—C 2 H 5 , —C(OCH 3 )(C 2 H 5 ) 2 , —C(OCH 3 )(CH 3 ) 2 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —C(═O)—OH, —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O—) 2 —CH 3 , —S(═O—) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —O-Benzyl, benzyl, cyclopentyl, cyclohexyl, pyrrolidinyl and piperidinyl;
a —O—R 6 moiety; a —NR 7 R 8 moiety or a —NR 9 —O—R 10 moiety;
R 4 represents F; Cl; Br; I; —CN; —NO 2 ; —NC; —OH; —NH 2 ; —SH; —C(═O)—H; —C(═O)—OH; —C(═O)—OR 7 ;
a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl and 4-octyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of —OH, F, Cl, Br, I, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —CN and —NO 2 ;
a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH-group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ;
a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl and diazepanyl, which may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3, —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ;
a —O—R 11 moiety; a —S—R 12 moiety, a —NH—R 13 moiety or a —NR 14 R 15 moiety;
R 5 represents H, F; Cl; Br; I; —CN; —NO 2 ; —NC; —OH; —NH 2 ; —SH; —C(═O)—H; —C(═O)—OH; —C(═O)—OR 17 ;
a radical selected from the group consisting of methyl, —CF 3 , —CH 2 F, —CF 2 H, —C 2 F 5 , ethyl, —CH 2 —CN, —CH 2 —OH, n-propyl, isopropyl, —CH 2 —CH 2 —CN, —CH 2 —CH 2 —OH, n-butyl, —CH 2 —CH 2 —CH 2 —CN, —CH 2 —CH 2 —CH 2 —OH, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl and 3-hexyl;
a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl and diazepanyl;
a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl) and pyrrolyl, which may be bonded via a —(CH 2 )-group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , F, Cl and Br;
a —O—R 11 moiety; a —S—R 12 moiety, a —NH—R 13 moiety or a —NR 14 R 15 moiety;
R 4 and R 5 together with the bridging carbon atom form a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and cyclooctenyl, which may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ; R 6 represents a hydrogen atom; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl vinyl, n-propenyl, n-butenyl, n-pentenyl, n-hexenyl, ethinyl, propinyl, n-butinyl, n-pentinyl and n-hexinyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of —OH, F, Cl, Br, I, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —CN, —NO, —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —NH—C(═O)—C(CH 3 ) 3 , —NH—C(═O)—O—CH 3 , —NH—C(═O)—O—C 2 H 5 , —NH—C(═O)—O—C(CH 3 ) 3 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C(CH 3 ) 3 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —C(═O)—OH, —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 , —C(═O)—CH 3 , —C(═O)—C 2 H 5 and —C(═O)—C(CH 3 ) 3 ;
a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, 8-aza-bicyclo[3.2.1]octyl and diazepanyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH-group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH—CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ;
a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH-group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SOF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O—)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —O—C(═O)—CH 3 , —O—C(═O)—C 2 H 5 , —O—C(═O)—CH(CH 3 ) 2 , —O—C(═O)—CH 2 —CH 2 —CH 3 , —CH 2 —N(CH 3 ) 2 , —(CH 2 )—N(C 2 H 5 ) 2 , —CH 2 —N(C 3 H 7 ) 2 , —CH 2 —N(C 4 H 9 ) 2 , —CH 2 —N(CH 3 )(C 2 H 5 ) and —(CH 2 )-morpholinyl;
a —P(═O)(OR 16 ) 2 moiety; a —C(═O)—OR 17 moiety; a —C(═O)—NH—R 18 moiety or a —C(═O)—R 19 moiety;
R 7 and R 8 , independently of another, in each case represent a hydrogen atom;
a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, 2-(6-methyl)-heptyl, 2-(5-methyl)-heptyl, 2-(5-methyl)-hexyl, 2-(4-methyl)-hexyl, 2-(7-methyl)-octyl; 2-(6-methyl)-octyl, vinyl, n-propenyl, n-butenyl, n-pentenyl, n-hexenyl, ethinyl, propinyl, n-butinyl, n-pentinyl and n-hexinyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of —OH, F, Cl, Br, I, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —CN and —NO 2 ;
a radical selected from the group consisting of (1,2,3,4)-tetrahydronaphthyl, (2,3)-dihydro-1H-cyclopenta[b]indolyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, diazepanyl, azocanyl, (2,5)-dihydrofuranyl, (2,5)-dihydrothiophenyl, (2,3)-dihydrofuranyl, (2,3)-dihydrofuranyl, (2,5)-dihydro-1H-pyrrolyl, (2,3)-dihydro-1H-pyrrolyl, tetrahydrothiopyranyl, tetrahydropyranyl, (3,4)-dihydro-2H-pyranyl, (3,4)-dihydro-2H-thiopyranyl, (1,2,3,6)-tetrahydropyridinyl, (1,2,3,4)-tetrahydropyridinyl, (1,2,5,6)-tetrahydropyridinyl, [1,3]-oxazinanyl, hexahydropyrimidinyl, (5,6)-dihydro-4H-pyrimidinyl, oxazolidinyl, (1,3)-dioxanyl, (1,4)-dioxanyl, (1,3)-dioxolanyl, indolinyl, isoindolinyl, decahydronaphthyl, (1,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinolinyl, octahydro-cyclopenta[c]pyrrolyl, (1,3,4,7,9a)-hexahydro-2H-quinolizinyl, (1,2,3,5,6,8a)-hexahydro-indolizinyl, decahydroquinolinyl, dodecahydro-carbazolyl, 9H-carbazolyl, decahydroisoquinolinyl, (6,7)-dihydro-4H-thieno[3,2-c]pyridinyl, (2,3)-dihydro-1H-benzo[de]isoquinolinyl, (1,2,3,4)-tetrahydroquinoxazlinyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, norbornenyl, 8-aza-bicyclo[3.2.1]octyl and 8-aza-spiro[4.5]decanyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH-group and/or may optionally be substituted with 1, 2, 3, 4 or 5 (substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —O—CH 2 —O—CH 3 , —O—CH 2 —CH 2 —O—CH 3 , —O—CH 2 —O—C 2 H 5 , —C(OCH 3 )(C 2 H 5 ) 2 , —C(OCH 3 )(CH 3 ) 2 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —C(═O)—OH, —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —O-Benzyl, benzyl, cyclopentyl, cyclohexyl, pyrrolidinyl and piperidinyl;
a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH-group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ;
a —P(═O)(OR 16 ) 2 moiety; a —C(═O)—OR 17 moiety; a —C(═O)—NH—R 18 moiety; a —C(═O)—R 19 moiety; a —S(═O) 2 —R 20 moiety; or a —NR 21 R 22 moiety;
R 9 represents hydrogen or an alkyl radical selected from the group consisting of methyl, ethyl and n-propyl. R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 20 , independently of another, in each case represent a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, 2-(6-methyl)-heptyl, 2-(5-methyl)-heptyl, 2-(5-methyl)-hexyl, 2-(4-methyl)-hexyl, 2-(7-methyl)-octyl; 2-(6-methyl)-octyl, vinyl, n-propenyl, n-butenyl, n-pentenyl, n-hexenyl, ethinyl, propinyl, n-butinyl, n-pentinyl and n-hexinyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of —OH, F, Cl, Br, I, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —CN and —NO 2 ;
a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, 8-aza-bicyclo[3.2.1]octyl and diazepanyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═—CH-group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —C—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O—)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ;
or a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH-group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ;
R 16 , R 17 , R 18 and R 19 , independently of one another, in each case represent a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, vinyl, n-propenyl, n-butenyl, n-pentenyl, n-hexenyl, ethinyl, propinyl, n-butinyl, n-pentinyl and n-hexinyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —NH—C(═O)—C(CH 3 ) 3 , —NH—C(═O)—O—CH 3 , —NH—C(═O)—O—C 2 H 5 , —NH—C(═O)—O—C(CH 3 ) 3 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C(CH 3 ) 3 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —OH, —C(═O)—OH, —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 , —C(═O)—CH 3 , —C(═O)—C 2 H 5 and —C(═O)—C(CH 3 ) 3 ;
or a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH-group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —O—C(═O)—CH 3 , —O—C(═O)—C 2 H 5 , —O—C(═O)—CH(CH 3 ) 2 , —O—C(═O)—CH 2 —CH 2 —CH 3 , —CH 2 —N(CH 3 ) 2 , —(CH 2 )—N(C 2 H 5 ) 2 , —CH 2 —N(C 3 H 7 ) 2 , —CH 2 —N(C 4 H 9 ) 2 , —CH 2 —N(CH 3 )(C 2 H 5 ) and —(CH 2 )-morpholinyl;
and
R 21 and R 22, independently of another, in each case represent hydrogen;
a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, 2-(6-methyl)-heptyl, 2-(5-methyl)-heptyl, 2-(5-methyl)-hexyl, 2-(4-methyl)-hexyl, 2-(7-methyl)-octyl; 2-(6-methyl)-octyl, vinyl, n-propenyl, n-butenyl, n-pentenyl, n-hexenyl, ethinyl, propinyl, n-butinyl, n-pentinyl and n-hexinyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of —OH, F, Cl, Br, I, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —CN and —NO 2 ;
a radical selected from the group consisting of (2,3)-dihydro-1H-cyclopenta[b]indolyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, diazepanyl, azocanyl, (2,5)-dihydrofuranyl, (2,5)-dihydrothiophenyl, (2,3)-dihydrofuranyl, (2,3)-dihydrofuranyl, (2,5)-dihydro-1H-pyrrolyl, (2,3)-dihydro-1H-pyrrolyl, tetrahydrothiopyranyl, tetrahydropyranyl, (3,4)-dihydro-2H-pyranyl, (3,4)-dihydro-2H-thiopyranyl, (1,2,3,6)-tetrahydropyridinyl, (1,2,3,4)-tetrahydropyridinyl, (1,2,5,6)-tetrahydropyridinyl, [1,3]-oxazinanyl, hexahydropyrimidinyl, (5,6)-dihydro-4H-pyrimidinyl, oxazolidinyl, (1,3)-dioxanyl, (1,4)-dioxanyl, (1,3)-dioxolanyl, indolinyl, isoindolinyl, decahydronaphthyl, (1,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinolinyl, octahydro-cyclopenta[c]pyrrolyl, (1,3,4,7,9a)-hexahydro-2H-quinolizinyl, (1,2,3,5,6,8a)-hexahydro-indolizinyl, decahydroquinolinyl, dodecahydro-carbazolyl, 9H-carbazolyl, decahydroisoquinolinyl, (6,7)-dihydro-4H-thieno[3,2-c]pyridinyl, (2,3)-dihydro-1H-benzo[de]isoquinolinyl, (1,2,3,4)-tetrahydroquinoxazlinyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, norbornenyl, 8-aza-bicyclo[3.2.1]octyl and 8-aza-spiro[4.5]decanyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —O—CH 2 —O—CH 3 , —O—CH 2 —CH 2 —O—CH 3 , —O—CH 2 —O—C 2 H 5 , —C(OCH 3 )(C 2 H 5 ) 2 , —C(OCH 3 )(CH 3 ) 2 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —C(═O)—OH, —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , cyclopentyl, cyclohexyl, pyrrolidinyl and piperidinyl;
or a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O) NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O) C 2 H 5 —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH2, —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ;
optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding N-oxide thereof, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.
15 . A compound according to claim 1 , characterized in that
X is O or S; R 1 represents a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyI, pyridazinyl, indolyl, isoindolyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzo[2,1,3]thiadiazolyl, [1,2,3]-benzothiadiazolyl, [2,1,3]-benzoxadiazolyl, [1,2,3]-benzoxadiazolyl, benzoxazolyl, benzthiazolyl, benzisoxazolyl, benzisothiazolyl and imidazo[2,1-b]thiazolyl, which may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , —CH 2 —Cl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —NO 2 , —OH, —O—CH 3 , —O—C 2 H 5 , F, Cl, Br, I, —CN, —OCF 3, —SCF 3 , —SCF 2 H, —SCFH 2 , phenoxy and thiophenyl, whereby the thiophenyl radical can be substituted with 1, 2 or 3 substituents independently selected from the group consisting of F, Cl, Br, methyl, ethyl and n-propyl;
or a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl and diazepanyl, which may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, F, Cl, Br, I, —CN, —OCF 3, —SCF 3 , —SCF 2 H and —SCFH 2 ;
R 2 represents a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl, isoindolyl, pyrinidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]furanyl, benzo[b]thiophenyl, benzo[2,1,3]thiadiazolyl, [1,2,3]-benzothiadiazolyl, [2,1,3]-benzoxadiazolyl, [1,2,3]-benzoxadiazolyl, benzoxazolyl, benzthiazolyl, benzisoxazolyl, benzisothiazolyl and imidazo[2,1-b]thiazolyl, which may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —OH, —O—CH 3 , —O—C 2 H 5 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H and —SCFH 2 ;
or a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl and diazepanyl, which may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H and —SCFH 2 ;
R 3 represents a radical selected from the group consisting of which is in each case bonded to the pyrazoline compound of general formula I in any position of the cyclic part of the aforementioned radicals including the NH— groups, preferably said radicals are bonded to the pyrazoline compound of general formula I at the nitrogen atom of the cyclic part of the aforementioned radicals; a —O—R 6 moiety, a —NR 7 R 8 moiety or a —NR 9 —O—R 10 moiety; R 4 represents F; Cl; Br; I; —CN; —NO 2 ; —NC; —OH; —NH 2 ; —SH; —C(═O)—H; —C(═O)—OH; —C(═O)—OR 17 ;
a radical selected from the group consisting of methyl, —CF 3 , —CH 2 F, —CF 2 H, —C 2 F 5 , ethyl, —CH 2 —CN, —CH 2 —OH, n-propyl, isopropyl, —CH 2 —CH 2 —CN, —CH 2 —CH 2 —OH, n-butyl, —CH 2 —CH 2 —CH 2 —CN, —CH 2 —CH 2 —CH 2 —OH, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl and 3-hexyl;
a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl) and pyrrolyl, which may be bonded via a —(CH 2 )— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , F, Cl and Br;
a —O—R 11 moiety; a —S—R 12 moiety, a —NH—R 13 moiety or a —NR 14 R 15 moiety;
R 5 represents H; F; Cl; Br;—C(═O)—OH; —C(═O)—OR 17 ; or an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl and n-butyl; or R 4 and R 5 together with the bridging carbon atom form a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl; R 6 represents a hydrogen atom; a radical selected from the group consisting of methyl, —CF 3 , —CH 2 F, —CF 2 H, —CH 2 —O—CH 3 , —C 2 F 5 , —CH 2 —CH 2 —F, ethyl, —CH 2 —CN, —CH 2 —OH, n-propyl, isopropyl, —CH 2 —CH 2 —CN, —CH 2 —CH 2 —OH, —CH 2 —CH 2 —OCH 3 , n-butyl, —CH 2 —CH 2 —CH 2 —CN, —CH 2 —CH 2 —CH 2 —OH, —CH 2 —CH 2 —CH2O—CH 3 , isobutyl, sec-butyl, tert-butyl, n-pentyl, —CH 2 —CH 2 —CH 2 —CH 2 —O—CH 3 , 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl and n-octyl;
a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, imidazolidinyl, azepanyl, 8-aza-bicyclo[3.2.1 ]octyl and diazepanyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 and —O—C(CH 3 ) 3 ;
a radical selected from the group consisting of pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl and imidazolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH=CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , F, Cl, Br, I, —O—C(═O)—CH 3 , —O—C(═O)—C 2 H 5 , —O—C(═O)—CH(CH 3 ) 2 , —O—C(═O)—CH 2 —CH 2 —CH 3 , —CH 2 —N(CH 3 ) 2 , —(CH 2 )—N(C 2 H 5 ) 2 , —CH 2 —N(C 3 H 7 ) 2 , —CH 2 —N(C 4 H 9 ) 2 , —CH 2 —N(CH 3 )(C 2 H 5 ) and —(CH 2 )-morpholinyl;
a —P(═O)(OR 16 ) 2 moiety; a —C(═O)—OR 17 moiety; a —C(═O)—NH—R 18 moiety or a —C(═O)—R 19 moiety;
R 7 and R 8 , independently of another, in each case represent a hydrogen atom;
a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, 2-(6-methyl)-heptyl, 2-(5-methyl)-heptyl, 2-(5-methyl)-hexyl, 2-(4-methyl)-hexyl, 2-(7-methyl)-octyl; 2-(6-methyl)-octyl, —CH 2 —NH 2 , —CH 2 —N(CH 3 ) 2 , —CH 2 —CH—NH 2 , —CH 2 —CH 2 —N(CH 3 ) 2 , —CH 2 —CH 2 —N(C 2 H 5 ) 2 , —CH 2 —CH 2 —CH 2 —NH 2 , —CH 2 —N(CH 3 ) 2 and —CH 2 —CH 2 —CH 2 —N(C 2 H 5 ) 2 ;
a radical selected from the group consisting of morpholinyl, piperidinyl, pyrrolidinyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, [1,2,3,4]-tetrahydronaphthyl and bicyclo[2.2.1]heptyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituient(s) independently selected from the group consisting of —OH, —O—CH 3 , —O—C 2 H 5 , —O-Benzyl, benzyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl and n-hexyl;
a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl) and triazolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, F, Cl and Br;
a —S(═O) 2 —R 20 moiety;
a —NR 21 R 22 moiety;
a radical selected from the group consisting of
which is in each case bonded to the pyrazoline compound of general formula I in any position of the cyclic part of the aforementioned radicals including the NH— groups, optionally via a —(CH 2 )— or —(CH 2 )—(CH 2 )— group, preferably said radicals are bonded to the pyrazoline compound of general formula I at the nitrogen atom of the cyclic part of the aforementioned radicals;
R 9 represents hydrogen; R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 20 , independently of another, in each case represent a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, 2-(6-methyl)-heptyl, 2-(5-methyl)-heptyl, 2-(5-methyl)-hexyl, 2-(4-methyl)-hexyl, 2-(7-methyl)-octyl; 2-(6-methyl)-octyl, vinyl, n-propenyl, n-butenyl, n-pentenyl, n-hexenyl, ethinyl, propinyl, n-butinyl, n-pentinyl and n-hexinyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of —OH, F, Cl, Br, I, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —CN and —NO 2 ;
a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, 8-aza-bicyclo[3.2.1]octyl and diazepanyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (═O), thioxo (═S), —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ;
or a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH 3 , —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 and —N(C 2 H 5 ) 2 ;
R 16 , R 17 , R 18 and R 19 , independently of one another, in each case represent a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, vinyl, n-propenyl, n-butenyl, n-pentenyl, n-hexenyl, ethinyl, propinyl, n-butinyl, n-pentinyl and n-hexinyl, which may optionally be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituent(s) independently selected from the group consisting of NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —NH—C(═O)—CH 3 , —NH—C(═O)—C 2 H 5 , —NH—C(═O)—C(CH 3 ) 3 , —NH—C(═O)—O—CH 3 , —NH—C(═O)—O—C 2 H 5 , —NH—C(═O)—O—C(CH 3 ) 3 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C(CH 3 ) 3 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —OH, —C(═O)—OH, —C(═O)—O—CH 3 , —C(═O)—O—C 2 H 5 , —C(═O)—O—C(CH 3 ) 3 , —C(═O)—CH 3 , —C(═O)—C 2 H 5 and —C(═O)—C(CH 3 ) 3 ;
or a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridazinyl, indolyl and isoindolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, —O—CH 3 , —O—C 2 H 5 , —O—CH 2 —CH 2 —CH 3 , —O—CH(CH 3 ) 2 , —O—CH 2 —CH 2 —CH 2 —CH 3 , —O—C(CH 3 ) 3 , —S—CH 3 , —S—C 2 H 5 , —S—CH 2 —CH 2 —CH 3 , —S—CH(CH 3 ) 2 , —S—CH 2 —CH 2 —CH 2 —CH 3 , —S—C(CH 3 ) 3 , F, Cl, Br, I, —CN, —OCF 3 , —SCF 3 , —SCF 2 H, —SCFH 2 , —OH, —SH, —NO 2 , —CHO, —C(═O)—CH 3 , —C(═O)—C 2 H 5 , —C(═O)—C(CH 3 ) 3 , —CF 2 H, —CFH 2 , —C(═O)—NH 2 , —C(═O)—NH—CH 3 , —C(═O)—NH—C 2 H 5 , —C(═O)—NH—C 3 H 7 , —C(═O)—N(CH 3 ) 2 , —C(═O)—N(C 2 H 5 ) 2 , —S(═O)—CH 3 , —S(═O)—C 2 H 5 , —S(═O)—C 3 H 7 , —S(═O) 2 —CH —S(═O) 2 —C 2 H 5 , —S(═O) 2 —C 3 H 7 , —NH 2 , —NH—CH 3 , —NH—C 2 H 5 , —N(CH 3 ) 2 , —N(C 2 H 5 ) 2 , —O—C(═O)—CH 3 , —O—C(═O)—C 2 H 5 , —O—C(═O)—CH(CH 3 ) 2 , —O—C(═O)—CH 2 —CH 2 —CH 3 , —CH 2 —N(CH 3 ) 2 , —(CH 2 )—N(C 2 H 5 ) 2 , —CH 2 —N(C 3 H 7 ) 2 , —CH 2 —N(C 4 H 9 ) 2 , —CH 2 —N(CH 3 )(C 2 H 5 ) and —(CH 2 )-morpholinyl;
and
R 21 and R 22, independently of another, in each case represent hydrogen;
a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, 2-(6-methyl)-heptyl, 2-(5-methyl)-heptyl, 2-(5-methyl)-hexyl, 2-(4-methyl)-hexyl, 2-(7-methyl)-octyl; 2-(6methyl)-octyl, —CH 2 —NH 2 , —CH—N(CH 3 ) 2 , —CH 2 —CH—NH 2 , —CH 2 —CH 2 —N(CH 3 ) 2 , —CH 2 —CH 2 —N(C 2 H 5 ) 2 , —CH 2 —CH 2 —CH 2 —NH 2 , —CH 2 —CH 2 —CH 2 —N(CH 3 ) 2 and —CH 2 —CH 2 —CH 2 —N(C 2 H 5 ) 2 ;
a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl and bicyclo[2.2.1]heptyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —OH, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl and n-hexyl;
a radical selected from the group consisting of phenyl, naphthyl, pyridinyl, furyl (furanyl), thienyl (thiophenyl) and triazolyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )—, —(CH 2 )—(CH 2 )—(CH 2 )— or —CH═CH— group and/or may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, F, Cl and Br;
or a radical selected from the group consisting of
which is in each case bonded to the pyrazoline compound of general formula I in any position of the cyclic part of the aforementioned radicals including the NH— groups, preferably said radicals are bonded to the pyrazoline compound of general formula I at the nitrogen atom of the cyclic part of the aforementioned radicals;
optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding N-oxide thereof, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.
16 . A compound according to claim 1 , characterized in that
x is O or S; R 1 represents a radical selected from the group consisting of phenyl and thienyl (thiophenyl), which may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —OH, —O—CH 3 , —O—C 2 H 5 , F, Cl, Br and I; R 2 represents a phenyl radical, which may be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of —OH, —O—CH 3 , —O—C 2 H 5 , F, Cl, Br and I; R 3 represents a radical selected from the group consisting of which is in each case bonded to the pyrazoline compound of general formula I in any position of the cyclic part of the aforementioned radicals including the NH— groups, preferably said radicals are bonded to the pyrazoline compound of general formula I at the nitrogen atom of the cyclic part of the aforementioned radicals; a —OR 6 — moiety or a —NR 7 R 8 moiety; R 4 represents F; Cl; Br; I; —OH, —CN; —C(═O)—H; —C(═O)—OH; —C(═O)—OR 17 ;
a radical selected from the group consisting of methyl, —CF 3 , —CH 2 F, —CF 2 H, —C 2 F 5 , ethyl, —CH 2 —CN, —CH 2 —OH, n-propyl, isopropyl, —CH 2 —CH 2 —CN, —CH 2 —CH 2 —OH, n-butyl, —CH 2 —CH 2 —CH 2 —CN, —CH 2 —CH 2 —CH 2 —OH, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl and 3-hexyl;
a benzyl radical or a —O—R 11 moiety;
R 5 represents H; F; Cl; Br;—C(═O)—OH; —C(═O)—OR 17 ; or a radical selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl and n-butyl;
or R 4 and R 5 together with the bridging carbon atom form a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl;
R 6 represents a hydrogen atom; a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl or a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl; R 7 represents a hydrogen atom or a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and tert-butyl; R 8 represents a radical selected from the group consisting of [1,2,3,4]-tetrahydronaphthyl, bicyclo[2.2.1]heptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl and cyclododecyl, which may be bonded via a —(CH 2 )—, —(CH 2 )—(CH 2 )— or —(CH 2 )—(CH 2 )—(CH 2 )-group and/or subsituted with 1, 2, 3 or 4 substituents selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, —OH, —O—CH 3 and —O—C 2 H 5 ;
or a radical selected from the group consisting of
which is in each case bonded to the pyrazoline compound of general formula I in any position of the cyclic part of the aforementioned radicals including the NH-groups, preferably said radicals are bonded to the pyrazoline compound of general formula I at the nitrogen atom of the cyclic part of the aforementioned radicals;
and
R 11 and R 17 , independently of one another, each represent a radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl and neo-pentyl; optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding N-oxide thereof, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.
17 . A compound or salt according to claim 1 selected from the group consisting of
[1] cis-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide hydro-chloride [2] trans-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide hydro-chloride [3] cis-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid azepan-1-ylamide [4] trans-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid azepan-1-ylamide [5] cis-[5-(4-Chloro-phenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazol-3-yl]-(4-cyclohexyl-piperazin-1-yl)-methanone [6] trans-[5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazol-3-yl]-(4-cyclohexyl-piperazin-1-yl)-methanone [7] cis-5-(4Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid pyrrolidin-1-ylamide [8] trans-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid pyrrolidin-1-ylamide [9] cis-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid (4-methyl-piperidin-1-yl)-amide [10] trans-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid (4-methyl-piperidin-1-yl)-amide [11] cis-[5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazol-3-yl]-piperidin-1-yl-methanone [12] trans-[5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazol-3-yl]-piperidin-1-yl-methanone [13] cis-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid (hexahydro-cyclopenta[c]pyrrol-2-yl)-amide [14] trans-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid (hexahydro-cyclopenta-[c]py-rrol-2-yl)-amide [15] cis-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid (2,3-dihydro-indol-1-yl)-amide [16] trans-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid (2,3-dihydro-indol-1-yl)-amide [17] cis-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid cyclobutylamide [18] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid cyclohexyl methyl-amide [19] cis-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid [20] trans-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid [21] cis-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid [22] trans-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [23] cis-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester [24] trans-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester [25] cis-5-(4Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester [26] trans-5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester [27] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid cyclohe-xyl ester [28] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,4-dimethyl-4,5-dihydro-1-H-pyrazole-3-carboxylic acid [29] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,4-dimethyl-4,5-dihydro-1-H-pyrazole-3-carboxylic acid piperidin-1-ylamide [30] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [31] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-hydroxy-4,5-dihydro-1H-pyrazole-3-carboxylic acid [32] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-hydroxy-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [33] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-(2-hydroxy-ethyl)-4,5-di-hydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [34] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-(2-hydroxy-ethyl)-4,5-di-hydro-1H-pyrazole-3-carboxylic acid [35] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-fluoromethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [36] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-fluoromethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid [37] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-formyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [38] 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-formyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid [39] 5-(4-chlorophenyl)-4-cyano-1-(2,4-dichlorophenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide [40] 5-(4-Chloro-phenyl)-4-cyano-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid [41] 1-(2,4-Dichloro-phenyl)-5-(4-fluoro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [42] 1-(2,4-Dichloro-phenyl)-4-ethyl-5-(4-fluoro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [43] 1-(2,4-Dichloro-phenyl)-5-(4-fluoro-phenyl)-4,4-dimethyl-4,5-dihydro-1-H-pyrazole-3-carboxylic acid piperidin-1-ylamide [44] 1-(2,4-Dichloro-phenyl)-5-(4-fluoro phenyl)-4-trifluoromethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [45] 1-(2,4-Dichloro-phenyl)-5-(4-fluoro-phenyl)-4-hydroxy-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [46] 1-(2,4-Dichloro-phenyl)-5-(4-fluoro-phenyl)-4-(2-hydroxy-ethyl)-4,5-dihydro-1pyrazole-3-carboxylic acid piperidin-1-ylamide [47] 1-(2,4-Dichloro-phenyl)-4-fluoromethyl-5-(4-fluoro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [48] 1-(2,4-Dichlorophenyl)-5-(4-fluoro-phenyl)-4-formyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [49] 4-Cyano-1-(2,4-dichloro-phenyl)-5-(4-fluoro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [50] 5-(4-Bromo-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [51] 5-(4-Bromo-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [52] 5-(4-Bromo-phenyl)-1-(2,4-dichloro-phenyl)-4,4-dimethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-yiamide [53] 5-(4-Bromo-phenyl)-1-(2,4-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [54] 5-(4-Bromo-phenyl)-1-(2,4-dichloro-phenyl)-4-hydroxy-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [55] 5-(4-Bromo-phenyl)-1-(2,4-dichloro-phenyl)-4-(2-hydroxy-ethyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [56] 5-(4-Bromo-phenyl)-1-(2,4-dichloro-phenyl)-4-fluoromethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [57] 5-(4-Bromo-phenyl)-1-(2,4-dichloro-phenyl)-4-formyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [58] 5-(4-Bromo-phenyl)-4-cyano-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [59] cis-5-(5-Chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [60] trans-5-(5-Chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [61] cis-5-(5-Chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [62] trans-5-(5-Chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [63] 5-(5-Chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4,4-dimethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [64] 5-(5-Chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [65] 5-(5-Chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-hydroxy-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [66] 5-(5-Chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-(2-hydroxy-ethyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [67] 5-(5-Chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-fluoromethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [68] 5-(5-Chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-formyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [69] 5-(5-Chloro-thiophen-2-yl)-4-cyano-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [70] cis-5-(5-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [71] trans-5-(5-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [72] cis-5-(5-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [73] trans-5-(5-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [74] 5-(5-Bromo-thiophen-2-yl)-1-(2,4-di-chloro-phenyl)-4,4-dimethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [75] cis-5-(4-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [76] trans-5-(4-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [77] cis-5-(4-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [78] trans-5-(4-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [79] 5-(4-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)4,4-dimethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [80] 5-(5-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [81] 5-(5-Bromo-thiophen-2-yl)-1-(2,4-di-chloro-phenyl)-4-hydroxy-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [82] 5-(5-Bromo-thiophen-2-yl)-1-(2,4-di-chloro-phenyl)-4-(2-hydroxy-ethyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [83] 5-(5-Bromo-thiophen-2-yl)-1-(2,4-di-chloro-phenyl)-4-fluoromethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [84] 5-(5-Bromo-thiophen-2-yl)-1-(2,4-di-chloro-phenyl)-4-formyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [85] 5-(5-Bromo-thiophen-2-yl)-4-cyano-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide [86] cis-5-(5-Chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid [87] trans-[5-(5-Chloro-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazol-3-yl]-piperidin-1-yl-methanone [88] cis-5-(5-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl) 4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid [89] trans-5-(5-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid [90] cis-5-(4-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid [91] trans-5-(4-Bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid, 92 (+)-cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 93 (−)-cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 94 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 95 trans-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 96 cis-5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid azepan-1-ylamide hydrochloride 97 trans-5-(4-Chlorophenyl)-1-(2,4-dichloro-phenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid azepan-1-ylamide hydrochloride 98 cis-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 99 trans-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 100 cis-5-(4-chlorophenyl)-N-(4-cyclopentylpiperazin-1-yl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 101 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-morpholino-4,5-dihydro-1H-pyrazole-3-carboxamide 102 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(4-methylpiperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 103 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(2,6-dimethylpiperidin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 104 cis-5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid (1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-amide 105 cis-5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid (1H,3H-benzo[de]isoquinolin-2-yl)-amide 106 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-((R)-2-(methoxymethyl)pyrrolidin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 107 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-((S)-2-(methoxymethyl)pyrrolidin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 108 cis-5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid (hexahydro-cyclopenta[c]pyrrol-2-yl)-amide hydrochloride 109 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 110 trans-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 111 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(indolin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 112 trans-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(indolin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 113 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(2-methylindolin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 114 cis-5-(4chlorophenyl)-N-(cyclohexylmethyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 115 cis-5-(4-chlorophenyl)-N-(cycloheptylmethyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 116 cis-5-(4-chlorophenyl)-N-cyclododecyl-1-( 2,4- dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 117 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 118 cis-N-(4-tert-butylcyclohexyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 119 cis-5-(4-chlorophenyl)-N-cyclooctyl-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 120 cis-N-(azocan-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 121 cis-N-(azocan-1-yl)-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 122 cis-azocan-1-yl(cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazol-3-yl)methanone 123 cis-5-(4-chlorophenyl)-N-cycloheptyl-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 124 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-cycloheptyl-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 125 trans-5-(4-chlorophenyl)-N-cycloheptyl-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 126 trans-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-cycloheptyl-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 127 cis-5-(4-chlorophenyl)-N-(cyclohexylmethyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 128 (+)-cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 129 (−)-cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 130 (−)-cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-((1R,2R)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 131 (+)-cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-((1R,2R)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 132 (+)-cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 133 (−)-cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 134 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(4-hydroxypiperidin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 135 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(4-hydroxypiperidin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 136 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(3-hydroxypiperidin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 137 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(3-hydroxypiperidin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 138 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(2-hydroxypiperidin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 139 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(2-hydroxypiperidin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 140 cis-5-(4-chlorophenlyl)-1-(2,4dichlorophenyl)-4-methyl-N-(4-oxopiperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 141 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(4-oxopiperidin-1yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 142 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(3-oxopiperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 143 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(-3oxopiperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 144 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(3,4-dihydropyridin-1(2H)-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 145 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(3,4-dihydropyridin-1(2H)-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 146 cis-5-(4-chlorophenyl)-1-(2,4dichlorophenyl)-N-(5,6-dihydropyridin-1(2H)-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 147 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(5,6-dihydropyridin-1(2H)-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 148 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 149 trans-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 150 cis-5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-py-razole-3-carboxylic acid cyclohexyl ester 151 N-(azepan-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,4-dimethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 152 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4,4-dimethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 153 N-(azepan-1-yl)-1-(2-chlorophehyl)-5-(4-chlorophenyl)-4,4-dimethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 154 cis-5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-trifluoromethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide 155 trans-5-(4-Chloro-phenyl)-1-(2,4-dichlorophenyl)-4-trifluoromethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide 156 cis-N-(azepan-1-yl)-5-(4chlorophenyl)-1-(2,4-dichlorophenyl)-4-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 157 trans-N-(azepan-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 158 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(piperidin-1-yl)-4-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 159 trans 1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(piperidin-1-yl)-4-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 160 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-(piperidin-1-ylcarbamoyl)-4,5-dihydro-1H-pyrazole-4-carboxylic acid 161 5-(4-chlorophenyl)-1-(2,4dichlorophenyl)-4,4-difluoro-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 162 cis-5-(4-chlorophenyl)-4-cyano-1-(2,4-dichlorophenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 163 cis-N-(azepan-1-yl)-5-(4-chlorophenyl)-4-cyano-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 164 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-cyano-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 165 cis-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-cyano-4,5-dihydro-1H-pyrazole-3-carboxamide 166 trans-5-(4-chlorophenyl)-4-cyano-1-(2,4-dichlorophenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 167 trans-N-(azepan-1-yl)-5-(4-chlorophenyl)-4-cyano-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 168 trans-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-cyano-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 169 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-ethyl-4,5-dihydro-1-pyrazole-3-carboxylic acid 170 trans-1-(2 chlorophenyl)-5-(4-chlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 171 cis-5-(4chlorophenyl)-1-(2,4dichlorophenyl)-4-ethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 172 trans-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 173 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-ethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3 carboxamide 174 trans-1-(2-chlorophenyl)-5-(4-chlorophenyl-4-ethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 175 cis-N-(azepan-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 176 trans-N-(azepan-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 177 cis-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 178 trans-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 179 cis-5-(4-chlorophenyl)-N-cycloheptyl-1-(2,4-dichlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 180 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-cycloheptyl-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 181 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 182 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-ethyl-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 183 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(indolin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 184 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-ethyl-N-(indolin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 185 cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 186 trans-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 187 cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 188 trans-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 189 cis-5-(4-bromophenyl)-1-(2-chlorophenyl)4-ethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 190 trans-5-(4-bromophenyl)-1-(2-chlorophenyl)-4-ethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 191 cis-N-(azepan-1-yl)-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 192 cis-N-(azepan-1-yl)-5-(4-bromophenyl)-1-(2-chlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 193 cis-5-(4-bromophenyl)-N-cycloheptyl-1-(2,4-dichlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 194 cis-5-(4-bromophenyl)-1-(2-chlorophenyl)-N-cycloheptyl-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 195 cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 196 cis-5-(4-bromophenyl)-1-(2-chlorophenyl)-4-ethyl-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 197 cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(indolin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 198 cis-5-(4-bromophenyl)-1-(2-chlorophenyl)-4-ethyl-N-(indolin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 199 cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 200 trans-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 201 cis-5-(4-bromophenyl)-1-(2-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 202 trans-5-(4-bromophenyl)-1-(2-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 203 cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 204 trans-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 205 cis 5-(4-bromophenyl)-1-(2-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 206 trans-5-(4-bromophenyl)-1-(2-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 207 cis-N-(azepan-1-yl)-5-(4-bromophenyl)-1-(2,4dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 208 trans-N-(azepan-1-yl)-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 209 cis-N-(azepan-1-yl)-5-(4-bromophenyl)-1-(2-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 210 cis-N-(azepan-1-yl)-5-(4-bromophenyl)-1-(2-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 211 cis-5-(4-bromophenyl)-N-cycloheptyl-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 212 cis-5-(4-bromophenyl)-1-(2-chlorophenyl)-N-cycloheptyl-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 213 cis-5-(4-bromophenyl)-1-(2,4dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 214 cis-5-(4-bromophenyl)-1-(2-chlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 215 cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-N-(indolin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 216 cis-5-(4-bromophenyl)-1-(2-chlorophenyl)-N-(indolin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 217 (+)-cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 218 (−)-cis-5-(4bromophenyl)-1-(2,4-dichlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 219 (+)-cis-5-(4-bromophenyl)-1-(2-chlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 220 (−)-cis-5-(4-bromophenyl)-1-(2-chlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 221 cis-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 222 trans-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 223 cis-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 224 trans-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 225 cis-1-(2-chlorophenyl)-5-(4-fluorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 226 trans-1-(2-chlorophenyl)-5-(4-fluorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 227 cis-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 228 trans-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 229 cis-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-fluorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 230 trans-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-fluorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 231 cis-N-cycloheptyl-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 232 cis-1-(2-chlorophenyl)-N-cycloheptyl-5-(4-fluorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 233 cis-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 234 cis-1-(2-chlorophenyl)-5-(4-fluorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 235 cis-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-N-(indolin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 236 cis-1-(2-chlorophenyl)-5-(4-fluorophenyl)-N-(indolin- -yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 237 (+)-cis-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 238 (−)-cis-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 239 (+)-cis-1-(2-chlorophenyl)-5-(4-fluorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 240 (−)-cis-1-(2-chlorophenyl)-5-(4-fluorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 241 cis-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 242 trans-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 243 cis-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 244 trans-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 245 cis-1-(2-chlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 246 trans-1-(2-chlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 247 cis-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 248 trans-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 249 cis-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 250 trans-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 251 cis-N-cycloheptyl-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 252 cis-1-(2-chlorophenyl)-N-cycloheptyl-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 253 cis-1-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 254 cis-1-(2-chlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 255 cis-1-(2,4-dichlorophenyl)-N-(indolin-1-yl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 256 cis-1-(2-chlorophenyl)-N-(indolin-1-yl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 257 (+)-cis-1-(2,4-dichlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 258 (−)-cis-1-(2,4-dichlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 259 (+)-cis-1-(2-chlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 260 (−)-cis-1-(2-chlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-(4-iodophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 261 cis-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 262 trans-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 263 cis-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 264 trans-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 265 cis-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 266 (+)-cis-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 267 (−)-cis-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 268 trans-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 269 cis-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 270 trans-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 271 cis-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 272 trans-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 273 cis-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 274 trans-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 275 cis-N-cycloheptyl-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 276 cis-1-(2-chlorophenyl)-N-cycloheptyl-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 277 cis-1-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 278 cis-1-(2-chlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 279 cis-1-(2,4-dichlorophenyl)-N-(indolin-1-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 280 cis-1-(2-chlorophenyl)-N-(indolin-1-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 281 (+)-cis-1-(2,4-dichlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 282 (−)-cis-1-(2,4-dichlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 283 (+)-cis-1-(2-chlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 284 (−)-cis-1-(2-chlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 285 cis-1-(2,4-dichlorophenyl)-N-(4-hydroxypiperidin-1-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 286 cis-1-(2-chlorophenyl)-N-(4-hydroxypiperidin-1-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 287 cis-1-(2,4-dichlorophenyl)-N-(3-hydroxypiperidin-1-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 288 cis-1-(2-chlorophenyl)-N-(3-hydroxypiperidin-1-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 289 cis-1-(2,4-dichlorophenyl)-N-(2-hydroxypiperidin-1-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 290 cis-1-(2-chlorophenyl)-N-(2-hydroxypiperidin-1-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 291 cis-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(4-oxopiperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 292 cis-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(4-oxopiperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 293 cis-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(3-oxopiperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 294 cis-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(3-oxopiperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 295 cis-1-(2,4-dichlorophenyl)-N-(3,4-dihydropyridin-1(2H)-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 296 cis-1-(2-chlorophenyl)-N-(3,4-dihydropyridin-1(2H)-yl)-5-(4methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 297 cis-1-(2,4-dichlorophenyl)-N-(5,6-dihydropyridin-1(2H)-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 298 cis-1-(2-chlorophenyl)-N-(5,6-dihydropyridin-1(2H)-yl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 299 cis-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 300 trans-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 301 cis-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 302 trans-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 303 cis-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 304 trans-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-N-(piperidin1-yl)-4-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 305 1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4,4-dimethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 306 N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4,4-dimethyl-4,5-dihydro-1H-pyrazole-3-carboxamide 307 1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4,4-dimethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 308 1-(2,4-dichlorophenyl)-4-formyl-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 309 1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-3-(piperidin-1-ylcarbamoyl)-4,5-dihydro-1H-pyrazole-4-carboxylic acid 310 1-(2,4-dichlorophenyl)-4-(2-hydroxyethyl)-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 311 1-(2,4-dichlorophenyl)-4-(fluoromethyl)-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 312 cis-4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 313 trans-4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 314 cis-N-(azepan-1-yl)-4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 315 trans-N-(azepan-1-yl)-4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 316 cis-1-(2-chlorophenyl)-4-cyano-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 317 trans-1-(2-chlorophenyl)-4-cyano-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 318 1-(2,4-dichlorophenyl)-4-hydroxy-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 319 1-(2-chloropheny!)-4,4-difluoro-5-(4methoxyphenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 320 1-(2-chlorophenyl)-44formyl-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 321 1-(2-chlorophenyl)-5-(4-methoxyphenyl)-3-(piperidin-1-ylcarbamoyl)-4,5-dihydro-1H-pyrazole-4-carboxylic acid 322 1-(2-chlorophenyl)-4-(2-hydroxyethyl)-5-(4-methoxyphenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 323 1-(2-chlorophenyl)-4-(flUoromethyl)-5-(4methoxyphenyl)-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 324 1-(2-chlorophenyl)-4-hydroxy-5-(4-methoxyphenyl)-N-(piperidin- 1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 325 cis-1-(2,4-dichlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 326 trans-1-(2,4-dichlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 327 cis-1-(2-chlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 328 trans-1-(2-chlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 329 cis-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 330 trans-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 331 cis-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 332 transN-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 333 cis-N-cycloheptyl-1-(2,4dichlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 334 cis-1-(2-chlorophenyl)-N-cycloheptyl-5-(4-ethoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 335 cis-1-(2,4-dichlorophenyl)-5-(4-ethoxyphenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 336 cis-1-(2-chlorophenyl)-5-(4-ethoxyphenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 337 cis-1-(2,4-dichlorophenyl)-5-(4-ethoxyphenyl)-N-(indolin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 338 cis-1-(2-chlorophenyl)-5-(4-ethoxyphenyl)-N-(indolin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 339 (+)-cis-1-(2,4-dichlorophenyl)-5-(4-ethoxyphenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 340 (−)-cis-1-(2,4-dichlorophenyl)-5-(4-ethoxyphenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 341 (+)-cis-1-(2-chlorophenyl)-5-(4-ethoxyphenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 342 (−)-cis-1-(2-chlorophenyl)-5-(4-ethoxyphenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 343 cis-1-(24dichlorophenyl-5-(4-hydroxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 344 trans-1-(2,4-dichlorophenyl)-5-(4-hydroxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 345 cis-1-(2-chlorophenyl)-5-(4-hydroxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 346 trans-1-(2-chlorophenyl)-5-(4-hydroxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 347 cis-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-hydroxyphenyl)-4′methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 348 trans-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 349 cis-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 350 trans-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 351 cis-N-cycloheptyl-1-(2,4-dichlorophenyl)-5-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 352 cis-1-(2-chlorophenyl)-N-cycloheptyl-5-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 353 cis-1-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-5-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 354 cis-1-(2-chlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-5-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 355 cis-1-(2,4-dichlorophenyl)-5-(4-hydroxyphenyl)-N-(indolin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 356 cis-1-(2-chlorophenyl)-5-(4-hydroxyphenyl)-N-(indolin-1-yl)-4-methyl4,5-dihydro-1H-pyrazole-3-carboxamide 357 (+)-cis-1-(2,4-dichlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 358 (−)-cis-1-(2,4-dichlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 359 (+)-cis-1-(2-chlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 360 (−)-cis-1-(2-chlorophenyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 361 cis-5-(5-chlorothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 362 trans-5-(5-chlorothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 363 cis-1-(2 chlorophenyl)-5-(5-chlorothiophen 2-yi)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 364 trans-1-(2-chlorophenyl)-5-(5-chlorothiophen-2-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 365 cis-5-(5-bromothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 366 trans-5-(5-bromothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-ethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 367 cis-1-(2,4-dichlorophenyl)-4-methyl-5-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid 368 trans-1-(2,4-dichlorophenyl)-4-methyl-5-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid 369 cis-1(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-5-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 370 trans-1-(2,4dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-5-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 371 cis-1-(2-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-5-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 372 trans-1-(2-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-5-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 373 cis-1-(2,4-dichlorophenyl)-4-methyl-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 374 trans-1-(2,4dichlorophenyl)-4-methyl-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid 375 cis-1-(2,4-dichlorophenyl)-4-methyl-5-phenyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 376 trans-1-(2,4-dichlorophenyl)-4-methyl-5-phenyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 377 cis-1-(2-chlorophenyl)-4-methyl-5-phenyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 378 trans-1-(2-chlorophenyl)-4-methyl-5-phenyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 379 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide hydrochloride 380 trans-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 381 cis-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 382 trans-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 383 cis-N-(azepan-1-yl)-5-(4chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carbothioamide 384 cis-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carbothioamide 385 cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 386 trans-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 387 cis-5-(4-bromophenyl)-1-(2-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 388 trans-5-(4-bromophenyl)-1-(2-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 389 cis-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 390 trans-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 391 cis-1-(2-chlorophenyl)-5-(4-fluorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 392 trans-1-(2-chlorophenyl)-5-(44luorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 393 cis-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 394 cis-N-(azepan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carbothioamide 395 trans-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 396 cis-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N (piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 397 cis-N-(azepan-1-yl)-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carbothioamide 398 trans-1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 399 cis-1-(2,4-dichlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 400 trans1-(2,4-dichlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 401 cis-1-(2-chlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 402 trans-1-(2-chlorophenyl)-5-(4-ethoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 403 cis-1(2,4-dichlorophenyl)-5-(4-hydroxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 404 trans-1-(2,4dichoropheno)-5-(4-hydroxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 405 cis-1-(2-chlorophenyl)-5-(4 hydroxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 406 trans-1-(2-chlorophenyl)-5(4-hydroxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carbothioamide 407 7-(4-Chloro-phenyl)-6-(2,4-dichlorophenyl)-5,6 diaza-spiro[2.4]hept-4-ene-4-carboxylic acid piperidin-1-ylamide 408 6-(2,4-Dichloro-henyl)-7-(4-methoxy-phenyl)-5,6-diaza-spiro[2.4]hept-4-ene-4-carboxylic acid piperidin-1-ylamide 409(+)-cis-N-N-((1S,2S)-2-(benzyloxy)cyclohexyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide [410] cis-1-(2,4-dichlorophehyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide [411] cis-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-I H-pyrazole-3-carboxamide [412] (4R,5S)-1-(2,4dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid [413] cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid [414] cis-N-(azepan-1-yl)1-(2,4-dichlorophenyl)-5-(4fluorophenyl)-4methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 415 cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-N-(indolin-1-yl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 416 trans-ethyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxylate 417 cis-1-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-4ethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 418 cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 419(−)-cis-5-(4-chlorophenyl)-1-(2,4-dichlorophen yl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 420(+)-cis-5-(4chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 421 trans-ethyl 1-(2,4-dichlorophenyl)-4-methyl-5phenyl-4,5-dihydro-H-pyrazole-3-carboxylate 422 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-((1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 423 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(3-methylcyclohexyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 424 cis-5-(4-chlorophenyl)-1-(2,4dichlorophenyl)-4-methyl-N-(2-methylcyclohexyl)-4,5-dihydro-1H-pyrazole-3-carboxamide 426 trans-5-(5-chlorothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 427 cis-5-(5-chlorothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride 428 cis-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride [429] 1-(2,4-dichlorophenyl)-4-methyl-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid [430] cis-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-5-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide hydrochloride [431] trans-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 432 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 434 cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide 436(+)-cis-N-((1S,2S)-2-(benzyloxy)cyclohexyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 437(−)-cis-N-((1R,2R)-2-(benzyloxy)cyclohexyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 438 cis-N-(azocan-1-yl)-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 439 cis-N-(azocan-1-yl)-1-(2-chlorophenyl)-5-(4methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 440 cis-N-(azocan-1-yl)-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 441 cis-N-(azocan-1-yl)-5-(4-bromophenyl)-1-(2-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 442 cis-N-(azocan-1-yl)-1-(2,4-dichlorophenyl)-5-(4fluorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 443 cis-N-(azocan-1-yl)-1-(2-chlorophenyl)-5-(4-fluorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide 444(+)-cis-5(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid azepan-1-ylamide hydrochloride 445(−)-cis- (4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid azepan-1-ylamide hydrochloride [446] cis-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide N-oxide [447] cis-5-(4-chlorophenyl)-1-(2-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide N-oxide [448] cis-N-(azepan-1-yl)-5-(4-chlorophenyl)-l-(2,4-dichlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide N-oxide [449] cis-N-(azepan-1-yl)-5-(4-chlorophenyl)-1-(2-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxamide N-oxide [450] cis-1-(2,4-dichlorophenyl)-5-(4methoxyphenyl)-4methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide N-oxide and [451] cis-1-(2-chlorophenyl)-5-(4-rethoxyphenyl)-4methyl-N-(piperidin-1-yl)-4,5-dihydro-1H-pyrazole-3-carboxamide N-oxide; optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding N-oxide thereof, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.
18 . Process for the preparation of a compound of general formula I according to claim 1 , wherein R 5 represents hydrogen, characterized in that at least one compound of general formula II,
wherein R 1 , X and R 4 have the meaning according to claim 1 , is reacted with at least one compound of general formula III,
or a corresponding salt thereof, wherein R 2 has the meaning according to claim 1 , in a reaction medium, optionally in an inert atmosphere, optionally in the presence of at least one acid, to yield at least one compound of general formula IV,
wherein R 1 , X, R 2 and R 4 have the meaning according to claim 1 , which is optionally isolated and/or purified,
and at least one compound of general formula IV is reacted with an activating agent in a reaction medium, optionally in an inert atmosphere, to yield at least one compound of general formula V,
wherein R 1 , X, R 2 and R 4 have the meaning according to claim 1 and A represents a leaving group, which is optionally purified and/or isolated,
and at least one compound of general formula V is reacted with at least one compound of general formula R 3 —H, wherein R 3 has the meaning according to claim 1 , in a reaction medium, optionally in an inert atmosphere, optionally in the presence of at least one base selected from the group consisting of diisopropylethylamine, triethylamine, pyridine, dimethylaminopyridine and N-methylmorpholine, to yield at least one compound of general formula I, wherein R 1 , R 2 , X, R 3 and R 4 have the meaning according to claim 1 and R 5 represents hydrogen, which is optionally purified and/or isolated;
or at least one compound of general formula IV is reacted with at least one compound of general formula R 3 —H, wherein R 3 represents a —NR 7 R 8 moiety, whereby R 7 and R 8 have the meaning according to claim 1 , in a reaction medium, in the presence of at least one coupling agent, optionally in the presence of at least one base, to yield at least one compound of general formula I, wherein R 1 , R 2 , X and R 4 have the meaning according to claim 1 , R 3 represents a —NR 7 R 8 moiety and R 5 represents hydrogen, which is optionally purified and/or isolated.
19 . Process for the preparation of a compound of general formula I according to claim 1 , wherein R 5 represents hydrogen, characterized in that at least one compound of general formula R 1 —C(═O)—H (general formula VIl), wherein R 1 has the meaning according to claim 1 , is reacted with at least one compound of general formula VI,
wherein R 4 and X have the meaning according to claim 1 and R′ represents a linear or branched C 1-6 -alkyl radical, a potassium cation or a sodium cation, in a reaction medium, optionally in an inert atmosphere, optionally in the presence of at least one base, to yield at least one compound of general formula II,
wherein R 1 , X and R 4 have the meaning according to claim 1 , which is optionally purified and/or isolated,
and at least one compound of general formula II is reacted with an activating agent in a reaction medium, optionally in an inert atmosphere, to yield at least one compound of general formula VIII,
wherein R 1 , X and R 4 have the meaning according to claim 1 and A represents a leaving group, which is optionally purified and/or isolated,
and at least one compound of general formula VII is reacted with at least one compound of general formula R 3 —H, wherein R 3 has the meaning according to claim 1 , in a reaction medium, optionally in an inert atmosphere, optionally in the presence of at least one base selected from the group consisting of diisopropylethylamine, triethylamine, pyridine, dimethylaminopyridine and N-methylmorpholine, to yield at least one compound of general formula IX,
wherein R 1 , X, R 3 and R 4 have the meaning according to claim 1 , which is optionally purified and/or isolated;
or at least one compound of general formula II is reacted with at least one compound of general formula R 3 —H, wherein R 3 represents a —NR 7 R 8 moiety, whereby R 7 and R 8 have the meaning according to claim 1 , in a reaction medium, in the presence of at least one coupling agent, optionally in the presence of at least one base, to yield at least one compound
general formula IX, wherein R 3 represents a —NR 7 R 8 moiety, which is optionally purified and/or isolated,
and at least one compound of general formula IX is reacted with at least one compound of general formula III,
wherein R 2 has the meaning according to claim 1 , in a reaction medium, optionally in an inert atmosphere, optionally in the presence of at least one acid, to yield at least one compound of general formula I, wherein R 1 , X, R 2 , R 3 and R 4 have the meaning according to claim 1 and R 5 represents hydrogen, which is optionally purified and/or isolated.
20 . Process for the preparation of a compound of general formula I according to claim 1 , wherein R 5 is unlike hydrogen, characterized in that at least one compound of general formula R 1 —C(═O)—H (general formula VII), wherein R 1 has the meaning according to claim 1 , is reacted with at least one compound of general formula VIb,
wherein R 4 , R 5 and X have the meaning according to claim 1 , R 5 is unlike hydrogen and R′ represents a linear or branched C 1-6 -alkyl radical, a potassium cation or a sodium cation, in a reaction medium, optionally in an inert atmosphere, optionally in the presence of at least one base, to yield at least one compound of general formula XXXI,
wherein R 1 , R 4 , R 5 and X have the meaning according to claim 1 , R 5 is unlike hydrogen, and R′ represents a linear or branched C 1-6 -alkyl radical, a potassium cation or a sodium cation,
and at least one compound of general formula XXXXI is reacted with a reagent, that transforms a hydroxyl group into a leaving group, preferably with a reagent selected from the group consisting of methansulfonylchloride and toluolsulfonylchloride, in a reaction medium, optionally in the presence of at least one base, preferably in the presence of at least one base selected from the group consisting of triethylamine, diisopropylethylamine, pyridine and N-methylmorpholine, to yield a compound of general formula XXXXII,
wherein R 1 , R 4 , R 5 and X have the meaning according to claim 1 , R 5 is unlike hydrogen, R′ represents a linear or branched C 1-6 -alkyl radical, a potassium cation or a sodium cation, and LG is a leaving group, preferably mesyl or tosyl;
and at least one compound of general formula XXXXII is reacted with at least one compound of general formula III,
or a corresponding salt thereof, wherein R 2 has the meaning according to claim 1 , in a reaction medium, optionally in an inert atmosphere, optionally in the presence of at least one acid, to yield at least one compound of general formula lVb,
wherein R 1 , X, R 2 , R 4 and R 5 have the meaning according to claim 1 and R 5 is unlike hydrogen, which is optionally isolated and/or purified,
and at least one compound of general formula lVb is reacted with an activating agent in a reaction medium, optionally in an inert atmosphere, to yield at least one compound of general formula Vb,
wherein R 1 , X, R 2 , R 4 and R 5 have the meaning according to claim 1 , R 5 is unlike hydrogen and A represents a leaving group, which is optionally purified and/or isolated,
and at least one compound of general formula Vb is reacted with at least one compound of general formula R 3 —H, wherein R 3 has the meaning according to claim 1 , in a reaction medium, optionally in an inert atmosphere, optionally in the presence of at least one base selected from the group consisting of diisopropylethylamine, triethylamine, pyridine, dimethylaminopyridine and N-methylmorpholine, to yield at least one compound of general formula I, wherein R 1 , R 2 , X, R 3 , R 4 and R 5 have the meaning according to claim 1 and R 5 is unlike hydrogen, which is optionally purified and/or isolated;
or at least one compound of general formula lVb is reacted with at least one compound of general formula R 3 —H, wherein R 3 represents a —NR 7 R 8 moiety, whereby R 7 and R 8 have the meaning according to claim 1 , in a reaction medium, in the presence of at least one coupling agent, optionally in the presence of at least one base, to yield at least one compound of general formula I, wherein R 1 , R 2 , X, R 4 and R 5 have the meaning according to claim 1 , R 3 represents a —NR 7 R 8 moiety and R 5 is unlike hydrogen, which is optionally purified and/or isolated.
21 . Medicament comprising at least one compound according to claim 1 including the aformenentioned excluded compounds and optionally at least one physiologically acceptable auxiliary agent.
22 . Medicament according to claim 21 for the modulation of cannabinoid-receptors, preferably cannabinoid 1 (CB 1 ) receptors, for the prophylaxis and/or treatment of disorders of the central nervous system, disorders of the immune system, disorders of the cardiovascular system, disorders of the endocrinous system, disorders of the respiratory system, disorders of the gastrointestinal tract or reproductive disorders.
23 . Medicament according to claim 21 for the prophylaxis and/or treatment of food intake disorders, preferably bulimia, anorexia, cachexia, obesity, type II diabetes mellitus (non-insuline dependent diabetes mellitus), more preferably obesity.
24 . Medicament according to claim 21 for the prophylaxis and/or treatment of psychosis.
25 . Medicament according to claim 21 for the prophylaxis and/or treatment of alcohol abuse and/or alcohol addiction, nicotine abuse and/or nicotine addiction, drug abuse and/or drug addiction and/or medicament abuse and/or medicament addiction, preferably drug abuse and/or drug addiction and/or nicotine abuse and/or nicotine addiction.
26 . Medicament according to claim 21 for the prophylaxis and/or treatment of cancer, preferably for the prophylaxis and/or treatment of one or more types of cancer selected from the group consisting of brain cancer, bone cancer, lip cancer, mouth cancer, esophageal cancer, stomach cancer, liver cancer, bladder cancer, pancreas cancer, ovary cancer, cervical cancer, lung cancer, breast cancer, skin cancer, colon cancer, bowel cancer and prostate cancer, more preferably for the prophylaxis and/or treatment of one or more types of cancer selected from the group consisting of colon cancer, bowel cancer and prostate cancer.
27 . Medicament according to claim 21 for the prophylaxis and/or treatment of one or more disorders selected from the group consisting of bone disorders, preferably osteoporosis (e.g. osteoporosis associated with a genetic predisposition, sex hormone deficiency, or aging), cancer-associated bone disease or Paget's disease of bone; schizophrenia, anxiety, depression, epilepsy, neurodegenerative disorders, cerebella disorders, spinocerebella disorders, cognitive disorders, cranial trauma, head trauma, stroke, panic attacks, peripheral neuropathy, glaucoma, migraine, Morbus Parkinson, Morbus Huntington, Morbus Alzheimer, Raynaud's disease, tremblement disorders, compulsive disorders, senile dementia, thymus disorders, tardive dyskinesia, bipolar disorders, medicament-induced movement disorders, dystonia, endotoxemic shock, hemorrhagic shock, hypotension, insomnia, immunologic disorders, sclerotic plaques, vomiting, diarrhea, asthma, memory disorders, pruritus, pain, or for potentiation of the analgesic effect of narcotic and non-narcotic analgesics, or for influencing intestinal transit.
28 . Use of at least one substituted pyrazoline compound according to claim 1 for the preparation of a medicament for the modulation of cannabinoid-receptors, preferably cannabinoid 1 (CB 1 ) receptors, for the prophylaxis and/or treatment of disorders of the central nervous system, disorders of the immune system, disorders of the cardiovascular system, disorders of the endocrinous system, disorders of the respiratory system, disorders of the gastrointestinal tract or reproductive disorders.
29 . Use of at least one substituted pyrazoline compound according to claim 1 for the preparation of a medicament for the prophylaxis and/or treatment of food intake disorders, preferably bulimia, anorexia, cachexia, obesity, type II diabetes mellitus (non-insuline dependent diabetes mellitus), more preferably obesity.
30 . Use of at least one substituted pyrazoline compound according to claim 1 for the preparation of a medicament for the prophylaxis and/or treatment of psychosis.
31 . Use of at least one substituted pyrazoline compound according to claim 1 for the preparation of a medicament for the prophylaxis and/or treatment of alcohol abuse and/or alcohol addiction, nicotine abuse and/or nicotine addiction, drug abuse and/or drug addiction and/or medicament abuse and/or medicament addiction, preferably drug abuse and/or drug addiction and/or nicotine abuse and/or nicotine addiction.
32 . Use of at least one substituted pyrazoline compound according to claim 1 for the preparation of a medicament for the prophylaxis and/or treatment of cancer, preferably for the prophylaxis and/or treatment of one or more types of cancer selected from the group consisting of brain cancer, bone cancer, lip cancer, mouth cancer, esophageal cancer, stomach cancer, liver cancer, bladder cancer, pancreas cancer, ovary cancer, cervical cancer, lung cancer, breast cancer, skin cancer, colon cancer, bowel cancer and prostate cancer, more preferably for the prophylaxis and/or treatment of one or more types of cancer selected from the group consisting of colon cancer, bowel cancer and prostate cancer.
33 . Use of at least one substituted pyrazoline compound according to claim 1 for the preparation of a medicament for the prophylaxis and/or treatment of one or more disorders selected from the group consisting of bone disorders, preferably osteoporosis (e.g. osteoporosis associated with a genetic predisposition, sex hormone deficiency, or aging), cancer-associated bone disease or Paget's disease of bone; schizophrenia, anxiety, depression, epilepsy, neurodegenerative disorders, cerebella disorders, spinocerebella disorders, cognitive disorders, cranial trauma, head trauma, stroke, panic attacks, peripheral neuropathy, glaucoma, migraine, Morbus Parkinson, Morbus Huntington, Morbus Alzheimier, Raynaud's disease, tremblement disorders, compulsive disorders, senile dementia, thymic disorders, tardive dyskinesia, bipolar disorders, medicament-induced movement disorders, dystonia, endotoxemic shock, hemorrhagic shock, hypotension, insomnia, immunologic disorders, sclerotic plaques, vomiting, diarrhea, asthma, memory disorders, pruritus, pain, or for potentiation of the analgesic effect of narcotic and non-narcotic analgesics, or for influencing intestinal transit.
34 . A method of modulating cannabinoid-receptors, preferably cannabinoid 1 (CB 1 ) receptors, of preventing and/or treating disorders of the central nervous system, disorders of the immune system, disorders of the cardiovascular system, disorders of the endocrinous system, disorders of the respiratory system, disorders of the gastrointestinal tract or reproductive disorders, comprising administering to a subject, preferably a human, therapeutically effective amount of at least one substituted pyrazoline compound according to claim 1 .
35 . A method of treating food intake disorders, preferably bulimia, anorexia, cachexia, obesity, type II diabetus mellitus (non-insuline dependent diabetes mellitus), more preferably obesity, comprising administering to a subject, preferably a human, a therapeutically effective amount of at least one substituted pyrazoline compound according to claim 1 .
36 . A method of treating psychosis comprising administering to a subject, preferably a human, a therapeutically effective amount of at least one substituted pyrazoline compound according to claim 1 .
37 . A method of treating alcohol abuse and/or alcohol addiction, nicotine abuse and/or nicotine addiction, drug abuse and/or drug addiction and/or medicament abuse and/or medicament addiction, preferably drug abuse and/or drug addiction and/or nicotine abuse and/or nicotine addiction, comprising administering to a subject, preferably a human, a therapeutically effective amount of at least one substituted pyrazoline compound according to claim 1 .
38 . A method of treating of cancer, preferably for the prophylaxis and/or treatment of one or more types of cancer selected from the group consisting of brain cancer, bone cancer, lip cancer, mouth cancer, esophageal cancer, stomach cancer, liver cancer, bladder cancer, pancreas cancer, ovary cancer, cervical cancer, lung cancer, breast cancer, skin cancer, colon cancer, bowel cancer and prostate cancer, more preferably for the prophylaxis and/or treatment of one or more types of cancer selected from the group consisting of colon cancer, bowel cancer and prostate cancer comprising administering to a subject, preferably a human, a therapeutically effective amount of at least one substituted pyrazoline compound according to claim 1 .
39 . A method of treating one or more disorders selected from the group consisting of bone disorders, preferably osteoporosis (e.g. osteoporosis associated with a genetic predisposition, sex hormone deficiency, or ageing), cancer-associated bone disease or Paget's disease of bone; schizophrenia, anxiety, depression, epilepsy, neurodegenerative disorders, cerebellar disorders, spinocerebellar disorders, cognitive disorders, cranial trauma, head trauma, stroke, panic attacks, peripheric neuropathy, glaucoma, migraine, Morbus Parkinson, Morbus Huntington, Morbus Alzheimer, Raynaud's disease, tremblement disorders, compulsive disorders, senile dementia, thymic disorders, tardive dyskinesia, bipolar disorders, medicarnent-induced movement disorders, dystonia, endotoxemic shock, hemorrhagic shock, hypotension, insomnia, immunologic disorders, sclerotic plaques, vomiting, diarrhoea, asthma, memory disorders, pruritus, pain, or for potentiation of the analgesic effect of narcotic and non-narcotic analgesics, or for influencing intestinal transit, comprising administering to a subject, preferably a human, a therapeutically effective amount of at least one substituted pyrazoline compound according to claim 1.Join the waitlist — get patent alerts
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