US2011015185A1PendingUtilityA1
Benzofuran Compounds
Est. expiryDec 19, 2023(expired)· nominal 20-yr term from priority
A61P 3/10A61P 43/00A61P 25/24A61P 25/28A61P 25/36C07D 405/12C07D 487/08A61P 25/16C07D 405/06C07D 495/04A61P 3/04A61P 25/14C07D 307/82C07D 403/14A61P 25/20C07D 403/12C07D 453/02A61P 25/00C07D 405/04A61P 25/06A61P 25/22A61P 25/18C07D 409/12C07D 409/14A61P 25/04C07D 307/79
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Claims
Abstract
The present invention relates to compounds of formula (I): wherein P, R 3 , W 1 , and W 2 are as described herein, to pharmaceutical compositions comprising the compounds, to processes for their preparation, as well as to the use of the compounds for the preparation of a medicament against 5-HT 6 receptor-related disorders.
Claims
exact text as granted — not AI-modified1 . A compound of the Formula (I):
wherein:
P is selected from a substituent of Formula (II)-(VII):
wherein:
x, y and j are each independently selected from 0, 1, and 2;
wherein the dashed bonds denote that P and R 3 , respectively, may be attached to either the A or B ring at any carbon atom that allows the substitution, provided that P and R 3 are not both simultaneously attached to ring B;
R 1 is selected from:
(a) C 1-6 -alkyl,
(b) C 1-6 -alkoxy-C 1-6 -alkyl
(c) C 3-6 -alkenyl,
(d) hydroxy-C 1-6 -alkyl,
(e) halo-C 1-6 -alkyl,
(f) aryl,
(g) arylcarbonylmethyl,
(h) aryl-C 3-6 -alkenyl,
(i) aryl-C 1-6 -alkyl,
(j) C 3-7 -cycloalkyl,
(k) heteroaryl,
(l) 4-piperidinyl,
(m) N-substituted 4-piperidinyl, wherein the substituents are selected from C 1-6 -alkyl and aryl-C 1-6 -alkyl,
(o) heteroaryl-C 1-6 -alkyl,
wherein any heteroaryl or aryl residue, alone or as part of another group may be substituted, independently, in one or more positions with a substituent selected from:
(a) hydrogen,
(b) halogen,
(c) C 1-6 -alkyl,
(d) hydroxy,
(e) C 1-6 -alkoxy,
(f) C 2-6 -alkenyl,
(g) C 2-3 -alkynyl,
(h) phenyl,
(i) phenoxy,
(j) benzyloxy,
(k) benzoyl,
(l) benzyl,
(m) —OCF 3 ,
(n) —CN,
(o) hydroxy-C 1-6 -alkyl,
(p) C 1-6 alkoxy-C 1-6 -alkyl,
(q) halo-C 1-6 -alkyl,
(r) —NR 9 R 9 ,
(s) —NO 2 ,
(t) —CONR 9 R 9 ,
(u) —NR 7 COR 10 ,
(v) —C(═O)R 10 ,
(x) C 1-6 -alkoxycarbonyl,
(y) C 1-6 -alkylthio,
(z) —SCF 3 ,
(aa) —CHF═CH 2 ,
(ab) methylsulfonyl, or
(ac) —COOH
with the proviso that when the substituent on the said aryl or heteroaryl residue is selected from phenyl, phenoxy, benzyloxy, benzoyl and benzyl, the phenyl ring thereof may be optionally substituted by one or more of halogen, C i-a -alkyl, C 1-4 -alkylthio, C 1-4 -alkoxy, cyano, or trifluoromethyl;
R 2 is selected from:
(a) hydrogen,
(b) C 1-6 -alkyl,
(c) C 1-6 -alkoxy-C 2-6 alkyl,
(d) hydroxy-C 2-6 -alkyl,
(e) —(CH 2 ) m —CH 2 —F, wherein m is 2-4,
(f) 3,3,3-trifluoropropyl, or
(g) C 1-4 -alkylsulfonyl, provided that P is selected from a substituent of formula (V);
W 1 and W 2 are each independently selected from:
(a) hydrogen,
(b) halogen,
(c) C 1-6 -alkyl,
(d) hydroxy,
(e) C 1-6 -alkoxy,
(f) C 1-6 -alkylthio,
(g) C 2-6 -alkenyl,
(h) phenyl,
(i) phenoxy,
(j) benzyloxy,
(k) benzoyl,
(l) benzyl,
(m) —OCF 3 ,
(n) —CN,
(o) hydroxy-C 1-6 -alkyl,
(p) C 1-6 -alkoxy-C 1-6 -alkyl,
(q) halo-C 1-6 -alkyl,
(r) —CONR 9 R 9 ,
(s) —C(═O)R 10 ,
(t) C 1-6 -alkoxycarbonyl,
(u) —SCF 3 , or
(v) —CHF═CH 2 ,
with the proviso that when W 1 and W 2 are selected from phenyl, phenoxy, benzoyl, benzyloxy and benzyl, the phenyl ring thereof may be optionally substituted by one or more of halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, or trifluoromethyl, and with the further proviso that, when W 1 and W 2 are not selected from methoxy, methyl and halogen, at least one of W 1 and W 2 is selected from hydrogen;
R 3 is H when P is a substituent of Formula (II) wherein R 1 is N-substituted 4-piperidinyl, or R 3 is a group selected from:
R 3 may also be a group selected from:
and further from a group selected from
—O—(C═NH)NR 11 R 11 , or
—(CH 2 ) n —O—NH(C═NH)—NR 11 R 11 ;
wherein:
n=0,1, 2 or 3
r is each independently 0, 1 or 2,
o=1, 2, or 3,
p is each independently 1 or 2,
s=2 or 3,
t=0 or 1,
t 1 =1 or 2,
t 2 =0 or 1,
f=1, 2, 3 or 4, and
f 1 =1, 2 or 4;
with the proviso that when t 1 and p simultaneously are 1, r is not 0;
X is selected from O, NR 7 and S;
X 1 is selected from NR 7 and S;
X 2 is selected from O, NR 7 and S, provided that X 2 is selected from NR 7 and S when t 2 =0;
X 3 is selected from NR 7 and S, provided that X 3 is selected from S when r=1;
X 4 is selected from O, NR 7 and S, provided that X 4 is selected from S and NR 7 when f is
selected from 2, 3, and 4;
Q is selected from CH 2 , SO 2 and oxygen, provided that when Q is SO 2 or oxygen, p is 1;
Z is selected from SO 2 and oxygen;
when P is a group selected from a substituent of Formula (V)-(VII), R 3 is additionally selected from the following groups:
wherein:
n=0,1, 2 or 3
r=0, 1 or 2,
o=1, 2, or 3,
p=1 or 2,
s=2 or 3, and
f=1, 2, 3 or 4;
wherein R 4 is a group selected from:
(a) hydrogen,
(b) C 1-6 -alkyl,
(c) 2-cyanoethyl,
(d) hydroxy-C 2-6 -alkyl,
(e) C 3-6 -alkenyl,
(f) C 3-6 -alkynyl,
(g) C 3-7 -cycloalkyl,
(h) C 3-2 -cycloalkyl-C 1-4 -alkyl,
(i) C 1-6 -alkoxy-C 2-6 -alkyl
(j) —C(═NH)—N—R 11 R 11 ,
(k) —C(═O)—N—R 11 R 11 ,
(l) —CH 2 —CO—N—R 11 R 11 , or
(m) 3,3,3-trifluoropropyl;
R 5 is selected from:
(a) hydrogen,
(b) C 1-4 -alkyl,
(c) hydroxy-C 1-4 -alkyl,
(d) C 1-4 -alkoxymethyl,
(e) halo-C 1-4 -alkyl,
(f) —NR 11 R 11 ,
(g) —CO—NR 11 R 11 ,
(h) hydroxy, provided that the said hydroxy group is not attached to a carbon atom adjacent to a ring nitrogen atom, or
(i) fluorine, provided that the said fluorine atom is not attached to a carbon atom adjacent to a ring nitrogen atom;
R 6 is selected from:
(a) hydrogen,
(b) C 1-4 -alkyl,
(c) hydroxy-C 1-4 -alkyl,
(d) C 1-4 -alkoxy-C 1-4 -alkyl,
(e) hydroxy, provided that the said hydroxy group is not attached to a carbon atom adjacent to a heterocyclic ring nitrogen atom, and further provided that the said heterocyclic ring is not substituted with oxo,
(f) fluorine, provided that the said fluorine atom is not attached to a carbon atom adjacent to a ring nitrogen atom, or
(g) halo-C 1-4 -alkyl;
R 7 is each independently selected from:
(a) hydrogen, provided that R 7 is not hydrogen when present simultaneously with r and said r is 1 or 2,
(b) C 1-4 -alkyl,
(c) hydroxy-C 2-4 -alkyl, or
(d) methoxy-C 2-4 -alkyl;
R 8 is each independently selected from:
(a) hydrogen, or
(b) C 1-4 -alkyl, and
when both R 8 simultaneously are selected from C 1-4 -alkyl, said C 1-4 -alkyls may be attached to the same or different carbon atoms, or when two groups are present at the same carbon atom they may together form a cyclopropane ring;
R 9 is each independently selected from:
(a) hydrogen,
(b) C 1-6 -alkyl
(c) C 3-7 -cycloalkyl, or
wherein the two R 9 groups together with the nitrogen to which they are attached form a heterocyclic ring; and provided that when the two R 9 groups form a piperazine ring, the nitrogen of the said piperazine ring that allows the substitution is optionally substituted with C 1-4 -alkyl, and further provided that when the two R 9 groups form a piperidine ring, any ring carbon atom in the said piperidine ring may be optionally substituted with methyl;
R 10 is selected from:
(a) C 1-6 -alkyl,
(c) aryl, or
(d) heteroaryl,
wherein heteroaryl or aryl may be substituted in one or more positions with substituents selected from halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, trifluoromethyl;
R 11 is each independently selected from:
(a) hydrogen,
(b) methyl, or
(c) ethyl, provided that R 11 is present in a group R 4 or R 26 selected from —CH 2 —CO—N—R 11 R 11 ;
R 12 is selected from:
(a) hydrogen,
(b) C 1-6 -alkyl,
(c) aryl,
(d) aryl-C 1-6 -alkyl,
(e) C 3-7 -cycloalkyl,
(f) C 3-7 -cycloalkyl-C 1-4 -alkyl,
(g) heteroaryl, or
(h) heteroaryl-C 1-6 -alkyl,
wherein any heteroaryl or aryl residue, alone or as part of another group, is optionally substituted, independently, in one or more positions with substituents selected from:
(a) hydrogen,
(b) halogen,
(c) C 1-6 -alkyl,
(d) hydroxy,
(e) C 1-6 -alkoxy,
(f) C 2-6 -alkenyl,
(g) C 2-6 -alkynyl,
(h) phenyl,
(i) phenoxy,
(j) benzyloxy,
(k) benzoyl,
(l) benzyl,
(m) —OCF 3 ,
(n) —CN,
(o) hydroxy-C 1-6 -alkyl,
(p) C 1-6 -alkoxy-C 1-6 -alkyl,
(q) halo-C 1-6 -alkyl,
(r) —NR 9 R 9 ,
(s) —NO 2 ,
(t) —CONR 9 R 9 ,
(u) —NR 7 COR 10 ,
(v) —C(═O)R 10 ,
(x) C 1-6 -alkoxycarbonyl,
(y) C 1-6 -alkylthio,
(z) —SCF 3 ,
(aa) —CHF═CH 2 ,
(ab) methylsulfonyl, or
(ac) —COOH
with the proviso that when the substituent on the said aryl or heteroaryl residue is selected from phenyl, phenoxy, benzyloxy, benzoyl, and benzyl, the phenyl ring thereof may be optionally substituted by one or more of halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, or trifluoromethyl;
R 13 is selected from:
(a) C 1-6 -alkyl,
(b) C 3-6 -cycloalkyl,
(c) aryl,
(d) heteroaryl,
(e) aryl-C 1-2 -alkyl, or
(f) heteroaryl-C 1-2 -alkyl,
wherein any heteroaryl or aryl residue may be substituted in one or more positions with substituents selected from halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, trifluoromethyl, and acetyl;
R 14 is selected from:
(a) aryl,
(b) heteroaryl,
(c) aryl-C 1-3 -alkyl, or
(d) heteroaryl-C 1-3 -alkyl;
wherein any heteroaryl or aryl residue may be substituted in one or more positions with substituents selected from halogen, C 1-4 -alkyl, C 1-4 alkoxy, cyano, and trifluoromethyl;
R 15 is selected from:
(a) fluorine, or
(b) hydroxy;
R 16 is selected from:
(a) hydrogen, provided that r=0,
(b) amino,
(c) dimethylamino,
(d) F, or
(e) OH;
R 17 is selected from:
(a) hydrogen,
(b) C 1-4 -alkyl,
(c) hydroxy, provided that the said hydroxy group is not attached to a carbon atom adjacent to a ring nitrogen atom;
R 18 is selected from:
(a) hydrogen, or
(b) fluorine;
R 19 is selected from:
(a) hydrogen,
(b) methyl,
(c) trifluoromethyl, or
(d) C 1-2 -alkoxymethyl;
and provided that at least one of R 19 and R 11 , when present simultaneously, is selected from a non-hydrogen substituent, and further provided that when R 19 is selected from trifluoromethyl or C 1-2 -alkoxymethyl, each R 11 is selected from hydrogen;
R 20 is selected from:
(a) hydrogen,
(b) C 1-4 -alkyl,
(c) hydroxy-C 1-4 -alkyl,
(d) C 1-4 -alkoxy-C 1-4 -alkyl, or
(e) fluoromethyl;
with the proviso that when t 2 is 1, R 20 is H;
R 21 and R 22 are each independently selected from:
(a) hydrogen, or
(b) methyl,
provided that, when present at the same time as R 11 , at least two of R 11 , R 21 and R 22 are selected from hydrogen;
R 23 is selected from:
(a) hydroxy-C 1-4 -alkyl,
(b) C 1-4 -alkoxymethyl,
(c) halo-C 1-4 -alkyl, or
(d) —CO—NR 11 R 11 , provided that R 4 is not selected from —C(═NH)—N—R 11 R 11 , —C(═O)—N—R 11 R 11 , and —CH 2 —CO—N—R 11 R 11 ;
R 24 is selected from:
(a) hydroxymethyl,
(b) methoxymethyl, or
(c) fluoromethyl;
R 25 is each independently selected from
(a) hydrogen,
(b) C 1-4 -alkyl,
(c) hydroxy-C 1-4 -alkyl,
(d) C 1-4 -alkoxy-C 1-4 -alkyl, or
(e) fluoromethyl,
with the proviso that when both R 25 simultaneously are selected from C 1-4 -alkyls, wherein said C 1-4 -alkyls may be attached to the same or different carbon atoms and with the further proviso that when one R 25 is selected from hydroxy-C 1-4 -alkyl, C 1-4 -alkoxy-C 1-4 -alkyl, and fluoromethyl, the other R 25 represents hydrogen; and
R 26 is selected from
(a) 2-cyanoethyl,
(b) C 3-6 -alkenyl,
(c) C 3-6 -alkynyl,
(d) C 3-7 -cycloalkyl,
(e) C 3-7 -cycloalkyl-C 1-4 -alkyl,
(f) —CH 2 —CO—NR 11 R 11 , or
(g) 3,3,3-trifluoropropyl;
with the proviso that R 2 and R 12 in Formula (III) are not simultaneously selected from hydrogen; and with the further proviso that the said R 2 and R 12 together may for a heterocyclic ring selected from piperidine, pyrrolidine, morpholine, piperazine thiomorpholine, and provided that when R 2 and R 12 together form a piperazine ring, the distal piperazine nitrogen is optionally substituted by C 1-4 alkyl or aryl, and wherein said aryl may be substituted in one or more positions with substituents selected from
halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, trifluoromethyl; or R 2 and R 12 together form
a heteroaromatic ring of Formula (VIII):
wherein v is 0, 1 or 2; and
further provided that when R 15 is selected from hydroxy, R 18 is selected from hydrogen; and
pharmaceutically acceptable salts, hydrates, solvates, geometrical isomers, tautomers, optical isomers, and prodrug forms thereof.
2 . The compound according to claim 1 of the general formula (1b)
wherein:
P is selected from a substituent of Formula (II)-(VII):
wherein:
x, y and j are each independently selected from 0, 1, and 2;
wherein the dashed bonds denote that R 3 may be attached to either the A or B ring at any carbon atom that allows the substitution;
R 1 is selected from:
(a) C 1-6 -alkyl,
(b) C 1-6 -alkoxy-C 2-6 -alkyl,
(c) C 3-6 -alkenyl,
(d) hydroxy-C 2-6 -alkyl,
(e) halo-C 1-6 -alkyl,
(f) aryl,
(g) arylcarbonylmethyl,
(h) aryl-C 3-6 -alkenyl,
(i) aryl-C 1-6 -alkyl,
(j) C 3-7 -cycloalkyl,
(k) heteroaryl,
(o) heteroaryl-C 1-6 -alkyl,
wherein any heteroaryl or aryl residue, alone or as part of another group may be optionally substituted, independently, in one or more positions with a substituent selected from:
(b) halogen,
(c) C 1-6 -alkyl,
(d) hydroxy,
(e) C 1-6 -alkoxy,
(f) C 2-6 -alkenyl,
(g) C 2-3 -alkynyl,
(h) phenyl,
(i) phenoxy,
(j) benzyloxy,
(k) benzoyl,
(l) benzyl,
(m) —OCF 3 ,
(n) —CN,
(o) hydroxy-C 1-6 -alkyl,
(p) C 1-6 -alkoxy-C 1-6 -alkyl,
(q) halo-C 1-6 alkyl,
(r) —NR 9 R 9 ,
(s) —NO 2 ,
(t) —CONR 9 R 9 ,
(u) —NR 7 COR 10 ,
(v) —C(═O)R 10 ,
(x) C 1-6 -alkoxycarbonyl,
(y) C 1-6 -alkylthio,
(z) —SCF 3 ,
(aa) —CHF═CH 2 ,
(ab) methylsulfonyl, or
(ac) —COOH,
with the proviso that when the substituent on the said aryl or heteroaryl residue is selected from phenyl, phenoxy, benzyloxy, benzoyl and benzyl, the phenyl ring thereof may be optionally substituted by one or more of halogen, C 1-4 -alkyl, C 1-4 -alkylthio, C 1-4 -alkoxy, cyano, or trifluoromethyl;
R 2 is selected from:
(a) hydrogen,
(b) C 1-6 -alkyl,
(c) C 1-6 -alkoxy-C 2-6 alkyl,
(d) hydroxy-C 2-6 -alkyl,
(e) —(CH 2 ) m —CH 2 —F, wherein m is 2-4, or
(g) C 1-4 -alkylsulfonyl, provided that P is selected from a substituent of formula (V);
W 1 and W 2 are each independently selected from:
(a) hydrogen,
(b) halogen,
(c) C 1-6 -alkyl,
(d) hydroxy,
(e) C 1-6 -alkoxy,
(f) C 1-6 -alkylthio,
(g) C 2-6 -alkenyl,
(m) —OCF 3 ,
(n) —CN,
(o) hydroxy-C 1-6 -alkyl,
(p) C 1-6 -alkoxy-C 1-6 -alkyl,
(q) halo-C 1-6 -alkyl,
(r) —CONR 9 R 9 ,
(s) —C(═O)R 10 ,
(t) C 1-6 -alkoxycarbonyl,
(o) —SCF 3 , or
(v) —CHF═CH 2 ,
with the proviso that when W 1 and W 2 are not selected from hydroxy, methoxy, methyl and halogen, at least one of W 1 and W 2 is selected from hydrogen;
R 3 is a group selected from:
wherein
n=0, 1, 2 or 3,
r=0, 1 or 2,
o=1, 2 or 3,
p=1 or 2,
s=2 or 3,
t=0 or 1,
t 2 =0 or 1,
f=1, 2, 3 or 4, and
f 1 =1, 2 or 4;
X 1 is selected from NR 7 and S;
X 2 is selected from O, NR 7 and S, provided that when t 2 =0 and s=2 then X 2 is selected from NR 7 and S;
X 3 is selected from NR 7 and S, provided that X 3 is selected from S when r=1;
X 4 is selected from O, NR 7 and S, provided that X 4 is selected from S and NR 7 when f is
selected from 2 and 3, and R 6 simultaneously is selected from hydrogen and C 1-4 alkyl;
when P is a group selected from a substituent of Formula (V)-(VII), R 3 is additionally selected from the following groups:
wherein:
r=0, 1 or 2,
o=1, 2 or 3,
p is each independently 1 or 2,
s=2 or 3, and
f=1, 2, 3 or 4;
R 4 is selected from:
(a) hydrogen,
(b) C 1-6 -alkyl,
(c) 2-cyanoethyl,
(d) hydroxy-C 2-6 -alkyl,
(e) C 3-6 -alkenyl,
(f) C 3-6 -alkynyl,
(g) C 3-7 -cycloalkyl,
(h) C 3-7 -cycloalkyl-C 1-4 -alkyl,
(i) C 1-4 -alkoxy-C 2-6 -alkyl
(j) —CH 2 —CO—N—R 11 R 11 , or
(m) 3,3,3-trifluoropropyl;
R 5 is selected from:
(a) hydrogen,
(b) C 1-4 -alkyl,
(c) hydroxy-C 1-4 -alkyl,
(d) C 1-4 -alkoxymethyl,
(e) halo-C 1-4 -alkyl,
(f) —NR 11 R 11 ,
(h) hydroxy, provided that the said hydroxy group is not attached to a carbon atom adjacent to a ring nitrogen atom, or
(i) fluorine, provided that the said fluorine atom is not attached to a carbon atom adjacent to a ring nitrogen atom;
R 6 is selected from:
(a) hydrogen,
(b) C 1-4 -alkyl,
(c) hydroxy-C 1-4 -alkyl,
(d) C 1-4 -alkoxy-C 1-4 -alkyl,
(e) hydroxy, provided that the said hydroxy group is not attached to a carbon atom adjacent to a heterocyclic ring nitrogen atom,
(f) fluorine, provided that the said fluorine atom is not attached to a carbon atom adjacent to a ring nitrogen atom, or
(g) halo-C 1-4 -alkyl;
R 7 is each independently selected from:
(a) hydrogen, provided that R 7 is not hydrogen when present simultaneously with r and said r is 1 or 2,
(b) C 1-4 -alkyl,
(c) hydroxy-C 2-4 -alkyl, or
(d) methoxy-C 2-4 -alkyl;
R 8 is each independently selected from:
(a) hydrogen, or
(b) C 1-4 -alkyl, with the proviso that when both R 8 simultaneously are selected from C 1-4 -alkyl, said C 1-4 -alkyl may be attached to the same or different carbon atoms, or when two groups are present at the same carbon atom they may together form a cyclopropane ring;
R 9 is each independently selected from:
(a) hydrogen,
(b) C 1-6 -alkyl
(c) C 3-7 -cycloalkyl, or
the two R 9 groups together with the nitrogen to which they are attached form a heterocyclic ring; and provided that when the two R 9 groups form a piperazine ring, the nitrogen of the said piperazine ring that allows the substitution may be optionally substituted with C 1-4 -alkyl; and further provided that when the two R 9 groups form a piperidine ring, any ring carbon atom in the said piperidine ring may be optionally substituted with methyl;
R 10 is selected from:
(a) C 1-6 -alkyl,
(c) aryl, or
(d) heteroaryl,
wherein heteroaryl or aryl may be optionally substituted in one or more positions with substituents selected from halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, trifluoromethyl;
R 11 is each independently selected from:
(a) hydrogen,
(b) methyl, or
(c) ethyl, provided that R 11 is present in a group R 4 or R 26 selected from —CH 2 —CO—N—R 11 R 11 ;
R 12 is selected from:
(a) hydrogen,
(b) C 1-6 -alkyl,
(c) aryl,
(d) aryl-C 1-6 -alkyl,
(e) C 3-7 -cycloalkyl,
(f) C 3-7 -cycloalkyl-C 1-4 -alkyl,
(g) heteroaryl, or
(h) heteroaryl-C 1-6 -alkyl,
wherein any heteroaryl or aryl residue, alone or as part of another group, may be optionally substituted, independently, in one or more positions with substituents selected from:
(b) halogen,
(c) C 1-6 -alkyl,
(d) hydroxy,
(e) C 1-6 -alkoxy,
(f) C 2-6 -alkenyl,
(g) C 2-3 -alkynyl,
(h) phenyl,
(i) phenoxy,
(j) benzyloxy,
(k) benzoyl,
(l) benzyl,
(m) —OCF 3 ,
(n) —CN,
(o) hydroxy-C 1-6 -alkyl,
(p) C 1-6 -alkoxy-C 1-6 -alkyl,
(q) halo-C 1-6 -alkyl,
(r) —NR 9 R 9 ,
(s) —NO 2 ,
(t) —CONR 9 R 9 ,
(u) —NR 7 COR 10 ,
(v) —C(═O)R 10 ,
(x) C 1-6 -alkoxycarbonyl,
(y) C 1-6 -alkylthio,
(z) —SCF 3 ,
(aa) —CHF═CH 2 ,
(ab) methylsulfonyl, or
(ac) —COOH,
with the proviso that when the substituent on the said aryl or heteroaryl residue is selected from phenyl, phenoxy, benzyloxy, benzoyl, and benzyl, the phenyl ring thereof may be optionally substituted by one or more of halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, or trifluoromethyl;
R 13 is selected from:
(a) C 1-6 -alkyl,
(b) C 3-6 -cycloalkyl,
(c) aryl,
(d) heteroaryl,
(e) aryl-C 1-2 -alkyl, or
(f) heteroaryl-C 1-2 -alkyl,
wherein any heteroaryl or aryl residue may be optionally substituted in one or more positions with substituents selected from halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, trifluoromethyl, and acetyl;
R 14 is selected from:
(a) aryl,
(b) heteroaryl,
(c) aryl-C 1-3 -alkyl, or
(d) heteroaryl-C 1-3 -alkyl,
wherein any heteroaryl or aryl residue may be substituted in one or more positions with substituents selected from halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, and trifluoromethyl;
R 20 is each independently selected from:
(a) hydrogen, or
(b) methyl;
with the proviso that when t 2 =1, then R 20 is hydrogen;
R 21 and R 22 are each independently selected from:
(a) hydrogen, or
(b) methyl,
provided that, when present simultaneously with R 11 , at least two of R 11 , R 21 and R 22 are selected from hydrogen;
R 23 is selected from:
(a) hydroxy-C 1-4 -alkyl,
(b) C 1-4 -alkoxymethyl, or
(c) halo-C 1-4 -alkyl;
R 25 is each independently selected from
(a) hydrogen,
(b) C 1-4 -alkyl,
(c) hydroxy-C 1-4 -alkyl,
(d) C 1-4 -alkoxy-C 1-4 -alkyl, or
e) fluoromethyl,
with the proviso that when both R 25 simultaneously are selected from C 1-4 -alkyl, said C 1-4 -alkyl may be attached to the same or different carbon atoms, and with the further proviso that when one R 25 is selected from hydroxy-C 1-4 -alkyl, C 1-4 -alkoxy-C 1-4 -alkyl, and fluoromethyl, the other R 25 represents hydrogen;
R 26 is selected from:
(a) 2-cyanoethyl,
(b) C 3-6 -alkenyl,
(c) C 3-6 -alkynyl,
(d) C 3-7 -cycloalkyl,
(e) C 3-7 -cycloalkyl-C 1-4 -alkyl,
(f) —CH 2 —CO—NR 11 R 11 , or
(g) 3,3,3-trifluoropropyl; and
with the proviso that R 2 and R 12 in Formula (III) are not simultaneously selected from hydrogen; and with the further proviso that the said R 2 and R 12 together may form a heterocyclic ring selected from piperidine, pyrrolidine, morpholine, piperazine thiomorpholine, and provided that when R 2 and R 12 together form a piperazine ring, the distal piperazine nitrogen may be optionally substituted by C 1-4 alkyl or aryl, and wherein said aryl may be optionally substituted in one or more positions with substituents selected from halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, trifluoromethyl; or R 2 and R 12 together form a heteroaromatic ring of Formula (VIII):
wherein v is 0 or 1.
3 . The compound according to claim 1 , wherein
P is selected from a substituent of Formula (II)-(V)
wherein x is 2, y is 0 and j is 1;
R 1 is selected from
(f) aryl,
(i) aryl-C 1-3 -alkyl,
(k) heteroaryl,
(o) heteroaryl-C 1-3 -alkyl,
wherein any heteroaryl or aryl residue, alone or as part of another group may be optionally substituted, independently, in one or more positions with a substituent selected from:
(b) halogen,
(c) C 1-4 -alkyl,
(d) hydroxy,
(e) C 1-4 -alkoxy,
(m) —OCF 3 ,
(n) —CN,
(o) hydroxy-C 1-4 -alkyl,
(p) C 1-2 -alkoxy-C 1-2 -alkyl,
(q) halo-C 1-3 -alkyl,
(r) —NR 9 R 9 ,
(t) —CONR 9 R 9 ,
(u) —NR 7 COR 10 ,
(v) —C(═O)R 10 ,
(x) C 1-3 -alkoxycarbonyl,
(y) C 1-3 -alkylthio, or
(ab) methylsulfonyl,
R 2 is selected from:
(a) hydrogen,
(b) C 1-4 -alkyl,
W 1 and W 2 are each independently selected from:
(a) hydrogen,
(b) halogen,
(c) C 1-4 -alkyl,
(d) hydroxy,
(e) C 1-4 -alkoxy,
(f) C 1-4 -alkylthio,
(m) —OCF 3 ,
(n) —CN,
(o) hydroxy-C 1-2 -alkyl,
(p) C 1-2 -alkoxy-C 1-2 -alkyl,
(q) —CF 3 ,
(r) —CONR 9 R 9 ,
(s) acetyl,
(t) Cl 1-4 -alkoxycarbonyl, or
with the proviso that when W 1 and W 2 are not selected from methoxy, methyl and halogen, at least one of W 1 and W 2 is selected from hydrogen;
R 3 is a group selected from:
wherein:
n=0, 1, 2 or 3
r is 0, 1 or 2,
o=1, 2, or 3,
p is 1 or 2,
s=2 or 3,
t=0 or 1,
t 2 =0 or 1, and
f=1, 2, 3 or 4;
X 1 is selected from NR 7 and S;
X 2 is selected from O, NR 7 and S, provided that X 2 is selected from NR 7 and S when t=0 and s=2;
X 3 is selected from NR 7 and S, provided that X 3 is selected from S when r=1;
X 4 is selected from O, NR 7 and S, provided that X 4 is selected from S and NR 7 when f is
selected from 2 and 3, and R 6 simultaneously is selected from hydrogen and C 1-4 alkyl; or;
when P is a group selected from formula (V) wherein j=1, R 3 is additionally selected from the following group;
R 4 is selected from:
(a) hydrogen,
(b) C 1-4 -alkyl,
(d) hydroxy-C 2-4 -alkyl,
(g) C 3-6 -cycloalkyl,
(h) C 3-6 -cycloalkyl-C 1-4 -alkyl,
(i) C 1-4 -alkoxy-C 2-4 -alkyl
(m) 3,3,3-trifluoropropyl;
R 5 is selected from:
(a) hydrogen,
(b) C 1-4 -alkyl,
(c) hydroxy-C 1-4 -alkyl,
(d) C 1-4 -alkoxymethyl,
(e) halo-C 1-4 -alkyl,
(f) —NR 11 R 11 ,
(g) hydroxy, provided that the said hydroxy group is not attached to a carbon atom adjacent to a ring nitrogen atom, or
(h) fluorine, provided that the said fluorine atom is not attached to a carbon atom adjacent to a ring nitrogen atom;
R 6 is selected from:
(a) hydrogen,
(b) C 1-4 -alkyl,
(c) hydroxy-C 1-4 -alkyl,
(d) C 1-4 -alkoxy-C 1-4 -alkyl,
(e) hydroxy, provided that the said hydroxy group is not attached to a carbon atom adjacent to a heterocyclic ring nitrogen atom,
(f) fluorine, provided that the said fluorine atom is not attached to a carbon atom adjacent to a ring nitrogen atom, or
(g) halo-C 1-4 -alkyl;
R 7 is each independently selected from:
(a) hydrogen, provided that R 7 is not hydrogen when present simultaneously with r and said r is 1 or 2,
(b) C 1-4 -alkyl,
(c) hydroxy-C 2-4 -alkyl, or
(d) methoxy-C 2-4 -alkyl;
R 8 is each independently selected from:
(a) hydrogen, or
(b) C 1-4 -alkyl, with the proviso that when both R 8 simultaneously are selected from C 1-4 -alkyl, said C 1-4 -alkyl may be attached to the same or different carbon atoms, or when two groups are present at the same carbon atom they may together form a cyclopropane ring;
R 9 is each independently selected from:
(a) hydrogen,
(b) C 1-6 -alkyl, or
the two R 9 groups together with the nitrogen to which they are attached form a heterocyclic ring; and provided that when the two R 9 groups form a piperazine ring, the nitrogen of the said piperazine ring that allows the substitution is optionally substituted with C 1-4 -alkyl;
R 10 is selected from:
(a) C 1-6 -alkyl,
(c) aryl, or
(d) heteroaryl,
wherein heteroaryl or aryl may be substituted in one or more positions with substituents selected from halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, trifluoromethyl;
R 11 is each independently selected from:
(a) hydrogen, or
(b) methyl,
(c) ethyl, provided that R 11 is present in a group R 26 selected from —CH 2 —CO—NR 11 R 11 ;
R 12 is selected from:
(a) hydrogen,
(c) aryl,
(d) aryl-C 1-3 -alkyl,
(g) heteroaryl, or
(h) heteroaryl-C 1-3 -alkyl,
wherein any heteroaryl or aryl residue, alone or as part of another group, may be optionally substituted, independently, in one or more positions with substituents selected from
(b) halogen,
(c) C 1-4 -alkyl,
(d) hydroxy,
(e) C 1-4 -alkoxy,
(m) —OCF 3 ,
(n) —CN,
(o) hydroxy-C 1-3 -alkyl,
(p) C 1-3 -alkoxy-C 1-3 -alkyl,
(q) halo-C 1-4 -alkyl,
(r) —NR 9 R 9 ,
(t) —CONR 9 R 9 ,
(u) —NR 7 COR 10 ,
(v) —C(═O)R 10 ,
(x) C 1-3 -alkylthio, or
(ab) methylsulfonyl;
R 13 is selected from:
(c) aryl,
(d) heteroaryl,
(e) aryl-C 1-2 -alkyl, or
(f) heteroaryl-C 1-2 -alkyl,
wherein any heteroaryl or aryl residue may be optionally substituted in one or more positions with substituents selected from halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, trifluoromethyl and acetyl;
R 14 is selected from:
(a) aryl,
(b) heteroaryl,
(c) aryl-C 1-3 -alkyl, or
(d) heteroaryl-C 1-3 -alkyl;
wherein any heteroaryl or aryl residue may be optionally substituted in one or more positions with substituents selected from halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, and trifluoromethyl;
R 21 and R 22 are each independently selected from:
(a) hydrogen, or
(b) methyl,
provided that, when present simultaneous with R 11 , at least two of R 11 , R 21 and R 22 are selected from hydrogen;
R 23 is selected from:
(a) hydroxy-C 1-4 -alkyl,
(b) C 1-4 -alkoxymethyl, or
(c) halo-C 1-4 -alkyl;
R 25 is selected from:
(a) hydrogen,
(b) C 1-4 -alkyl,
(c) hydroxy-C 1-4 -alkyl,
(d) C 1-4 -alkoxy-C 1-4 -alkyl, or
(e) fluoromethyl;
with the proviso that when both R 25 simultaneously are selected from C 1-4 -alkyl, said C 1-4 -alkyl may be attached to the same or different carbon atoms, and with the further proviso that when one R 25 is selected from hydroxy-C 1-4 -alkyl, C 1-4 -alkoxy-C 1-4 -alkyl, and fluoromethyl; the other R 25 represents hydrogen;
R 26 is selected from:
(e) C 3-7 -cycloalkyl-C 1-4 -alkyl,
(f) —CH 2 —CO—NR 11 R 11 , or
(g) 3,3,3-trifluoropropyl;
with the proviso that R 2 and R 12 in Formula (III) are not simultaneously selected from hydrogen; and with the further proviso that the said R 2 and R 12 together may for a heterocyclic ring selected from piperidine, pyrrolidine, morpholine, piperazine thiomorpholine, and provided that when R 2 and R 12 together form a piperazine ring, the distal piperazine nitrogen may be optionally substituted by C 1-4 alkyl or aryl, and wherein said aryl may be substituted in one or more positions with substituents selected from halogen, C 1-4 -alkyl, C 1-4 -alkoxy, cyano, trifluoromethyl; or R 2 and R 12 together form
a hetero aromatic ring of Formula (VIII):
wherein v is 0 or 1.
4 . The compound according to claim 1 , which has the general Formula (XII):
wherein P, R 3 , W 1 , and W 2 are as defined in claim 1 .
5 . The compound according to claim 4 , wherein
P is selected from a substituent of Formula (II)-(IV)
x is 2 and y is 0;
R 1 is selected from aryl and heteroaryl, wherein any heteroaryl or aryl residue may be optionally substituted, independently, in one or more positions with a substituent selected from halogen, C 1-4 -alkyl C 1-4 -alkoxy and trifluoromethyl;
R 2 is selected from hydrogen;
W 1 and W 2 are hydrogen;
R 3 is a group selected from
wherein
p=1 or 2;
R 4 is selected from:
(a) hydrogen, or
(b) methyl,
R 11 is each independently selected from:
(a) hydrogen, or
(b) methyl,
(c) ethyl, provided that R 11 is present in a group R 26 selected from —CH 2 —CO—NR 11 R 11 ;
R 12 and R 13 are each independently selected from aryl and heteroaryl,
wherein any heteroaryl or aryl residue may be optionally substituted, independently, in one or more positions with a substituent selected from halogen, C 1-4 -alkyl, C 1-4 -alkoxy, and CF 3 ;
R 25 is selected from:
(a) hydrogen, or
(b) C 1-4 -alkyl;
R 26 is selected from:
(e) C 3-7 -cycloalkyl-C 1-4 -alkyl,
(f) —CH 2 —CO—NR 11 R 11 , or
(g) 3,3,3-trifluoropropyl.
6 . The compound according to claim 5 , wherein
R 1 , R 12 and R 13 are each independently selected from phenyl or substituted phenyl selected from 2-methoxy-5-methylphenyl, 2-methylphenyl, 4-methylphenyl, 4-fluorophenyl, 3,4-dimethoxyphenyl, 2-chlorophenyl, 2-trifluoromethylphenyl, 2,6-dichlorophenyl, 3-chloro-4-methylphenyl, 3-methylphenyl, 3,6-dichloro-2-methylphenyl, and 2-chloro-5-fluorophenyl; or heteroaryl or substituted heteroaryl selected from 2-thienyl, 5-chloro-2-thienyl, 5-chloro- and 1,3-dimethyl-1H-pyrazol-4-yl; and R 2 is selected from hydrogen.
7 . The compound according to claim 5 , wherein R 3 is a group selected from:
R 4 is each independently selected from:
(a) hydrogen, or
(b) methyl,
R 11 is each independently selected from:
(a) hydrogen, or
(b) methyl;
R 25 is each independently selected from:
(a) hydrogen, or
(b) methyl.
8 . The compound according to claim 5 , wherein R 4 is selected from:
(a) hydrogen, (b) methyl, or (c) ethyl.
9 . The compound according to claim 5 , wherein R 4 or R 11 is selected from hydrogen.
10 . The compound according to claim 1 , which has the general Formula (XIII):
wherein P, R 3 , W 1 , and W 2 are as defined as in claim 1 .
11 . The compound according to claim 10 , wherein
P is selected from a substituent of Formula (II)-(IV)
x is 2 and y is 0;
R 1 is selected from aryl and heteroaryl, wherein any heteroaryl or aryl residue may be optionally substituted, independently, in one or more positions with a substituent selected from halogen, C 1-4 -alkyl, trifluoromethoxy, and C 1-4 -alkoxy;
R 2 is selected from hydrogen;
W 1 and W 2 are hydrogen;
R 3 is a group selected from
R 4 is each independently selected from:
(a) hydrogen, or
(b) C 1-4 -alkyl;
R 25 is each independently selected from:
(a) hydrogen, or
(b) C 1-4 -alkyl, with the proviso that when both R 25 represent C 1-4 -alkyl, said C 1-4 -alkyl may be attached to the same or different carbon atoms;
R 12 and R 13 are each independently selected from aryl and heteroaryl, wherein any heteroaryl or aryl residue may be optionally substituted, independently, in one or more positions with a substituent selected from halogen, C 1-4 -alkyl, trifluoromethyl, and C 1-4 -alkoxy.
12 . The compound according to claim 11 , wherein
P is selected from a substituent of Formula (II)
R 1 is selected from 2-methoxy-5-methylphenyl;
R 2 is selected from hydrogen;
W 1 and W 2 are hydrogen;
R 3 is a group selected from:
R 4 is each independently selected from
a) hydrogen, or
b) methyl;
R 26 is each independently selected from
a) hydrogen, or
b) methyl.
13 . The compound according to claim 1 , which is selected from
N-(7-{Methyl[3-(methylamino)propyl]amino}-1-benzofuran-5-yl)benzenesulfonamide hydrochloride, N-(7-Piperidin-1-yl-1-benzofuran-5-yl)benzenesulfonamide, 4-Fluoro-N-(7-piperidin-1-yl-1-benzofuran-5-yl)benzenesulfonamide, 3,4-Dimethoxy-N-(7-piperidin-1-yl-1-benzofuran-5-yl)benzenesulfonamide hydrochloride, 3,4-Dimethoxy-N-(7-pyrrolidin-1-yl-1-benzofuran-5-yl)benzenesulfonamide, N-(7-Pyrrolidin-1-yl-1-benzofuran-5-yl)benzenesulfonamide, 4-Fluoro-N-(7-pyrrolidin-1-yl-1-benzo furan-5-yl)benzenesulfonamide hydrochloride, 4-Fluoro-N-(7-morpholin-4-yl-1-benzofuran-5-yl)benzenesulfonamide hydrochloride, N-(7-Morpholin-4-yl-1-benzofuran-5-yl)benzenesulfonamide hydrochloride, 3,4-Dimethoxy-N-(7-morpholin-4-yl-1-benzofuran-5-yl)benzenesulfonamide, 2-Methoxy-5-methyl-N-(7-pyridin-4-yl-1-benzofuran-5-yl)benzenesulfonamide, N-(7-Pyridin-3-yl-1-benzofuran-5-yl)benzenesulfonamide trifluoroacetate, 2-Methoxy-5-methyl-N-(7-pyridin-3-yl-1-benzo furan-5-yl)benzenesulfonamide trifluoroacetate, N-(7-Pyrazin-2-yl-1-benzofuran-5-yl)benzenesulfonamide trifluoroacetate, N-(7-Pyrimidine-5-yl-1-benzofuran-5-yl)benzenesulfonamide hydrochloride, and, N-[7-(1-Aza-bicyclo[2.2.2]oct-2-en-3-yl)-benzofuran-5-yl]-2-methoxy-5-methyl-benzenesulfonamide hydrochloride, 2-[4-5-{[(2-Chlorophenyl)sulfonyl]amino}-1-benzofuran-7-yl)piperazin-1-yl]-N,N-diethylacetamide hydrochloride, N,N-diethyl-2-[4-(5-{[(2-methoxy-5-methylphenyl)sulfonyl]amino}-1-benzofuran-7-yl)piperazin-1-yl]acetamide hydrochloride, N-[7-(1-Azabicyclo[2.2.2]oct-3-yloxy)-1-benzofuran-5-yl]benzenesulfonamide hydrochloride, N-[7-(1-Azabicyclo[2.2.2]oct-3-yloxy)-1-benzofuran-5-yl]-2-chlorobenzenesulfonamide hydrochloride, N-[7-(1-Azabicyclo[2.2.2]oct-3-yloxy)-1-benzofuran-5-yl]-2-methoxy-5-1082 benzenesulfonamide hydrochloride, N-{7-[(2-Morpholin-4-ylethyl)amino]-1-benzofuran-5-yl}benzenesulfonamide hydrochloride, 2-Methoxy-5-methyl-N-{7-[(2-morpholin-4-ylethyl)amino]-1-benzofuran-5-yl}benzenesulfonamide hydrochloride, N-{7-[(2-Morpholin-4-ylethyl)amino]-1-benzofuran-5-yl}-2-(trifluoromethyl)benzenesulfonamide hydrochloride, 2,6-Dichloro-N-{7-[(2-morpholin-4-ylethyl)amino]-1-benzofuran-5-yl}benzenesulfonamide hydrochloride, N-(7-{[2(Dimethylamino)ethyl]amino}-1-benzofuran-5-yl)-2-methoxy-5-benzenesulfonamide hydrochloride, 2-Chloro-N(7-{[2-(dimethylamino)}-1-benzofuran-5-yl)benzenesulfonamide hydrochloride, N-[7-(Pyridin-4-ylamino)-1-benzofuran-5-yl]benzenesulfonamide hydrochloride, 2-Chloro-N-[7-(pyridin-4-ylamino)-1-benzofuran-5-yl]benzenesulfonamide hydrochloride, 2-Methoxy-5-methyl-N-[7-(pyridin-4-ylamino)-1-benzofuran-5-yl]benzenesulfonamide hydrochloride, 2-Methoxy-5-methyl-N-[7-(piperazin-1-ylcarbonyl)-1-benzofuran-5-yl]benzenesulfonamide hydrochloride, 2-Methoxy-5-methyl-N-[7-(piperazin-1-ylmethyl)-1-benzofuran-5-yl]benzenesulfonamide hydrochloride, N-{7-[(3-Aminopyrrolidin-1-yl)methyl]-1-benzofuran-5-yl}-2-methoxy-5-methylbenzenesulfonamide hydrochloride, N-[7(6,6-Dioxidohexahydrothieno[3,4-b]pyrazin-1(2H)-yl)-1-benzofuran-5-yl]-2-methoxy-5-methylbenzenesulfonamide hydrochloride, N-[7(6,6-Dioxidohexahydrothieno[3,4-b]pyrazin-1(2H)-yl)-1-benzofuran-5-yl]benzenesulfonamide hydrochloride, N-{7-[(2-Pyrrolidin-1-ylethyl)amino]-1-benzofuran-5-yl}benzenesulfonamide hydrochloride, 2-Methoxy-5-methyl-N-{7-[(2-pyrrolidin-1-ylethyl)amino]-1-benzofuran-5-yl}benzenesulfonamide hydrochloride, N-{7-[(2-Pyrrolidin-1-yl ethyl)amino]-1-benzofuran-5-yl}-2-(trifluoromethyl)benzenesulfonamide hydrochloride, 3-Chloro-4-methyl-N-{7-[(2-pyrrolidin-1-ylethyl)amino]-1-benzofuran-5-yl}benzenesulfonamide hydrochloride, 2-Methoxy-5-methyl-N-{7-[(3-morpholin-4-ylpropyl)amino]-1-benzofuran-5-yl}benzenesulfonamide hydrochloride, N-{7-[(3-Morpholin-4-ylpropyl)amino]-1-benzofuran-yl}-2-(trifluoromethyl)benzenesulfonamide hydrochloride, 3-Chloro-4-methyl-N-{7-[(3-morpholin-4-ylpropyl)amino]-1-benzofuran-5-yl}benzenesulfonamide hydrochloride, N-[7-({[(2R)-1-Ethylpyrrolidin-2-yl]methyl}amino)-1-benzofuran-5-yl]benzenesulfonamide hydrochloride, N-[7-({[(2R)-1-Ethylpyrrolidin-2-yl]methyl}amino)-1-benzofuran-5-yl]-2-methoxy-5-methylbenzenesulfonamide hydrochloride, N-[7-({[(2R)-1-Ethylpyrrolidin-2-yl]methyl}amino)-1-benzofuran-5-yl]-2-(trifluoromethyl)benzenesulfonamide hydrochloride, N-[7-({[(2R)-1-Ethylpyrrolidin-2-yl]methyl}amino)-1-benzofuran-5-yl]-3-methylbenzenesulfonamide hydrochloride, N-[7-({[(2R)-1-Ethylpyrrolidin-2-yl]methyl}amino)-1-benzo furan-5-yl]thiophene-2-sulfonamide hydrochloride, 5-Chloro-N-[7-({[(2R)-1-ethylpyrrolidin-2-yl]methyl}amino)-1-benzofuran-5-yl]thiophene-2-sulfonamide hydrochloride, 5-Chloro-N-[7-({[(2R)-1-ethylpyrrolidin-2-yl]methyl}amino)-1-benzofuran-5-yl]-1,3-dimethyl-1H-pyrazole-4-sulfonamide hydrochloride, N-(7-{[3-(2-Methylpiperidin-1-yl)propyl]amino}-1-benzofuran-5-yl)benzenesulfonamide hydrochloride, 2-Methoxy-5-methyl-N-(7-{[3-(2-methylpiperidin-1-yl)propyl]amino}-1-benzofuran-5-yl)benzenesulfonamide hydrochloride, N-(7-{[3-(2-Methylpiperidin-1-yl)propyl]amino}-1-benzofuran-5-yl)-2-(trifluoromethyl)benzenesulfonamide hydrochloride, 5-Chloro-1,3-dimethyl-N-(7-{[3-(2-methylpiperidin-1-yl)propyl]amino}-1-benzofuran-5-yl)-1H-pyrazole-4-sulfonamide hydrochloride, N-[7-(6-Aminopyridin-3-yl)-1-benzofuran-5-yl]-2-methoxy-5-methylbenzenesulfonamide, N-{7-[4-(Cyclopropylmethyl)piperazin-1-yl]-1-benzofuran-5-yl}-2-methoxy-5-methylbenzenesulfonamide hydrochloride, 2-Methoxy-5-methyl-N-{7-[4-(3,3,3-trifluoropropyl)piperazin-1-yl]-1-benzofuran-5-yl}benzenesulfonamide hydrochloride, 2-Methoxy-5-methyl-N-{7-[3-(trifluoromethyl)piperazin-1-yl]-1-benzofuran-5-yl}benzenesulfonamide hydrochloride, N-[7-(Aminopiperidin-1-yl)-1-benzofuran-5-yl]-2-(trifluoromethyl)benzenesulfonamide hydrochloride, N-[7-(Aminopiperidin-1-yl)-1-benzofuran-5-yl]-benzenesulfonamide hydrochloride, N-[7-(Aminopiperidin-1-yl)-1-benzofuran-5-yl]-2-chlorobenzenesulfonamide hydrochloride, N-[7-(Aminopiperidin-1-yl)-1-benzofuran-5-yl]-2-methoxy-5-methylbenzenesulfonamide hydrochloride, N-(7-{[cis-3-Fluoropiperidin-4-yl]oxy}-1-benzofuran-5-yl)-2-methoxy-5-methylbenzenesulfonamide hydrochloride, N-(7-{trans-3-Fluoropiperidin-4-yl]oxy}-1-benzofuran-5-yl)-2-methoxy-5-methylbenzenesulfonamide hydrochloride, N-(7-{[cis-3-Fluoropiperidin-4-yl]oxy}-1-benzofuran-5-yl)-2-(trifluoromethyl)benzenesulfonamide hydrochloride, N-(7-{[trans-3-Fluoropiperidin-4-yl]oxy}-1-benzofuran-5-yl)-2-(trifluoromethyl)benzenesulfonamide hydrochloride; 2-Chloro-N-(7-{[trans-3-fluoropiperidin-4-yl]oxy}-1-benzofuran-5-yl)benzenesulfonamide hydrochloride, N-(7-{[trans-3-Fluoropiperidin-4-yl]oxy}-1-benzofuran-5-yl)-3-methylbenzenesulfonamide hydrochloride, 3,6-Dichloro-N-(7-{[trans-3-fluoropiperidin-4-yl]oxy}-1-benzofuran-5-yl)-2-methylbenzenesulfonamide hydrochloride, 2-Chloro-5-fluoro-N-(7-{[trans-3-fluoropiperidin-4-yl]oxy}-1-benzofuran-5-yl)benzenesulfonamide hydrochloride, N-(2-Methoxy-5-methylphenyl)-7-[(3-methylpiperazin-1-yl)methyl]-1-benzofuran-5-sulfonamide hydrochloride, N-(2-Methylphenyl)-7-(piperazin-1-ylmethyl)-1-benzofuran-5-sulfonamide, trifluoroacetate, 7-[(3,5-Dimethylpiperazin-1-yl)methyl]-N-(2-methylphenyl)-1-benzofuran-5-sulfonamide, trifluoroacetate, N-(2-Methylphenyl)-7-[(3-methylpiperazin-1-yl)methyl]-1-benzofuran-5-sulfonamide, trifluoroacetate, 7-(1,4-Diazepan-1-ylmethyl)-N-(2-methylphenyl)-1-benzo furan-5-sulfonamide, trifluoroacetate, 7-{(trans-2,5-Dimethylpiperazin-1-yl)methyl}-N-(2-methylphenyl)-1-benzofuran-5-sulfonamide, trifluoroacetate, N-(2-Methylphenyl)-7-{[(2R)-2-methylpiperazin-1-yl]methyl}-1-benzo furan-5-sulfonamide, trifluoroacetate, N-(2-Methoxy-5-methylphenyl)-7-[(3-methylpiperazin-1-yl)methyl]-1-benzofuran-5-sulfonamide, trifluoroacetate, 7-(1,4-Diazepan-1-ylmethyl)-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide, trifluoroacetate, N-(2-Methoxy-5-methylphenyl)-7-(piperazin-1-ylmethyl)-1-benzofuran-5-sulfonamide, trifluoroacetate, 7-{(cis-3,5-Dimethylpiperazin-1-yl)methyl}-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide, trifluoroacetate, 7-{[trans-2,5-Dimethylpiperazin-1-yl]methyl}-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide, trifluoroacetate, 7-[(1S,4S)-2,5-Diazabicyclo [2.2.1]hept-2-ylmethyl]-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide, trifluoroacetate, N-(2-Methoxy-5-methylphenyl)-7-[(2-methylpiperazin-1-ylmethyl]-1-benzofuran-5-sulfonamide, trifluoroacetate, 2-Chloro-N-[7-(piperazin-1-ylmethyl)-1-benzo furan-5-yl]benzenesulfonamide dihydrochloride, 2-Methyl-N-[7-(piperazin-1-ylmethyl)-1-benzofuran-5-yl]benzenesulfonamide, dihydrochloride, N-[7-(piperazin-1-ylmethyl)-1-benzofuran-5-yl]thiophene-2-sulfonamide, dihydrochloride, 2-Chloro-N-[7-(1,4-diazepan-1-ylmethyl)-1-benzofuran-5-yl]benzenesulfonamide dihydrochloride, N-[7-(1,4-Diazepan-1-ylmethyl)-1-benzofuran-5-yl]-2-methylbenzenesulfonamide, dihydrochloride, N-[7-(1,4-Diazepan-1-ylmethyl)-1-benzofuran-5-yl]thiophene-2-sulfonamide dihydrochloride, 2-Methoxy-5-methyl-N-{7-[(2-methylpiperazin-1-yl)methyl]-1-benzofuran-5-yl}benzenesulfonamide, dihydrochloride, 2-Methyl-N-{7-[(2-methylpiperazin-1-yl)methyl]-1-benzofuran-5-yl}benzenesulfonamide dihydrochloride, 2,5-Dichloro-N-{7-[(2-methylpiperazin-1-yl)methyl]-1-benzo furan-5-yl}thiophene-3-sulfonamide dihydrochloride, 2-Methoxy-5-methyl-N-{7-[(3-methylpiperazin-1-yl)methyl]-1-benzofuran-5-yl}benzenesulfonamide, dihydrochloride, N-{7-[(3-Methylpiperazin-1-yl)methyl]-1-benzo furan-5-yl}-2-(trifluoromethyl)benzenesulfonamide, dihydrochloride, 2-Chloro-N-{7-[(3-methylpiperazin-1-yl)methyl]-1-benzofuran-5-yl}benzenesulfonamide, dihydrochloride, N-{7-[(1S,4S)-2,5-Diazabicyclo [2.2.1]hept-2-ylmethyl]-1-benzofuran-5-yl}-2-methoxy-5-methylbenzenesulfonamide, dihydrochloride, N-{7-[(1S,4S)-2,5-Diazabicyclo[2.2.1]hept-2-ylmethyl]-1-benzo furan-5-yl}-2-(trifluoromethyl)benzenesulfonamide, dihydrochloride, N-{7-[(1S,4S)-2,5-Diazabicyclo [2,2.1]hept-2-ylmethyl]-1-benzofuran-5-yl}-2-methylbenzenesulfonamide, dihydrochloride, 2-Methoxy-5-methyl-N-{7-[(trans-2,5-dimethylpiperazin-1-yl)methyl]-1-benzofuran-5-yl}benzenesulfonamide, bistrifluoroacetate, 2-Methyl-N-{7-[(trans-2,5-dimethylpiperazin-1-yl)methyl]-1-benzo furan-5-yl}benzenesulfonamide, bistrifluoroacetate, 2-Chloro-N-{7-[(trans-2,5-dimethylpiperazin-1-yl)methyl]-1-benzofuran-5-yl}benzenesulfonamide, bistrifluoroacetate, 1-({5-[(2-Methoxy-5-methylphenyl)sulfonyl]-1-benzofuran-7-yl}methyl)piperazine, trifluoroacetate, 1-{[5-(Phenylsulfonyl)-1-benzofuran-7-yl]methyl}piperazine, trifluoroacetate, 1-({5-[(4-Methylphenyl)sulfonyl]-1-benzofuran-7-yl}methyl)piperazine, trifluoroacetate, 1-({5-[(2-Methoxy-5-methylphenyl)sulfonyl]-1-benzofuran-7-yl}methyl)-1,4-diazepane, trifluoroacetate, 1-{[5-(Phenylsulfonyl)-1-benzofuran-7-yl]methyl}-1,4-diazepane, trifluoroacetate, 1-({5-[(4-Methylphenyl)sulfonyl]-1-benzofuran-7-yl}methyl)-1,4-diazepane, trifluoroacetate, 1-({5-[(2-Methoxy-5-methylphenyl)sulfonyl]-1-benzofuran-7-yl}methyl)-2-methylpiperazine, trifluoroacetate, 1-({5-[(2-Methoxy-5-methylphenyl)sulfonyl]-1-benzofuran-7-yl}methyl)-2-methylpiperazine, trifluoroacetate, N-(2-Methylphenyl)-7-{[(3R)-pyrrolidin-3-ylamino]methyl}-1-benzofuran-5-sulfonamide, trifluoroacetate, N-(2-Methylphenyl)-7-(piperidin-4-ylmethyl)-1-benzofuran-5-sulfonamide, trifluoroacetate, N-(2-Methylphenyl)-7-(pyrrolidin-3-ylmethyl)-1-benzofuran-5-sulfonamide, trifluoroacetate, N-(2-Methylphenyl)-7-(piperidin-3-ylmethyl)-1-benzofuran-5-sulfonamide, trifluoroacetate, 2-Methoxy-5-methyl-N-[7-(piperidin-4-ylmethyl)-1-benzofuran-5-yl]benzenesulfonamide, trifluoroacetate, 3-({5-[(4-Methylphenyl)sulfonyl]-1-benzofuran-7-yl}methyl)pyrrolidine, trifluoroacetate, 2-Methoxy-5-methyl-N-[5-(piperidin-4-ylmethyl)-1-benzofuran-7-yl]benzenesulfonamide, trifluoroacetate, 2-Methoxy-5-methyl-N-{5-[(3-methylpiperazin-1-yl)methyl]-1-benzofuran-7-yl}benzenesulfonamide, bis(trifluoroacetate, 2-Methoxy-5-methyl-N-[5-(piperidin-4-ylmethyl)-1-benzofuran-7-yl]benzenesulfonamide, trifluoroacetate.
14 . A pharmaceutical formulation comprising a compound according to claim 1 as active ingredient, in combination with a pharmaceutically acceptable diluent or carrier.
15 . A method for the prophylaxis or treatment of a 5-HT 6 receptor-related disorder or to achieve reduction of body weight and of body weight gain, the method comprising administering to a subject in need of such treatment an effective amount of a compound according to claim 1 .
16 . The method according to claim 15 , for the prophylaxis or treatment of a 5-HT 6 receptor-related disorder wherein the disorder is selected from obesity; type II diabetes; and disorders of the central nervous system.
17 . The method of claim 16 , wherein the disorder is a disorder of the central nervous system selected from anxiety, depression, panic attacks, memory disorders, cognitive disorders, epilepsy, sleep disorders, migraine, anorexia, bulimia, binge eating disorders, obsessive compulsive disorders, psychoses, Alzheimer's disease, Parkinson's disease, Huntington's chorea, schizophrenia, attention deficit hyperactive disorder, withdrawal from drug abuse, neurodegenerative diseases characterized by impaired neuronal growth, and pain.
18 . A method for modulating 5-HT 6 receptor activity, the method comprising administering to a subject in need of such modulating an effective amount of a compound according to claim 1 , wherein modulating 5-HT 6 receptor activity optionally comprises inhibiting or promoting 5-HT 6 receptor activity.
19 . A cosmetic composition comprising a compound according to claim 1 as an active ingredient, in combination with a cosmetically acceptable diluent or carrier.
20 . The cosmetic composition of claim 19 , wherein the composition comprises an amount of the compound of claim 1 that is effective for the prophylaxis or treatment of a 5-HT 6 receptor-related disorder or to achieve reduction of body weight and of body weight gain.Join the waitlist — get patent alerts
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