US2008221141A1PendingUtilityA1
Spirocyclic Cyclohexane Compounds Useful To Treat Substance Dependency
Est. expiryApr 11, 2025(expired)· nominal 20-yr term from priority
A61P 25/36A61P 25/30A61P 25/00A61K 31/407A61K 31/438A61K 31/485A61K 45/06A61K 31/137
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Claims
Abstract
Spirocyclic cyclohexane compounds useful in pharmaceutical compositions for use in the treatment of substance dependency.
Claims
exact text as granted — not AI-modified1 . A method of treating substance dependency in a patient, said method comprising administering to said patient an effective amount of a spirocyclic cyclohexane compound corresponding to formula I:
wherein
R 1 and R 2 independently of one another denote H or CH 3 or together denote (CH 2 ) 4 or (CH 2 ) 5 and form a ring with the nitrogen atom to which they are bound, with the proviso that R 1 and R 2 are not both H;
R 3 denotes phenyl, benzyl or heteroaryl, in each case unsubstituted or singly or multiply substituted with F, Cl, OH, CN or OCH 3 ;
W denotes NR 4 , O or S, where
R 4 denotes H; C 1-5 -alkyl; phenyl; COR 12 bound via a C 1-3 -alkyl group; or SO 2 R 12 ; where
R 12 denotes H; branched or unbranched, saturated or unsaturated C 1-7 -alkyl, unsubstituted or singly or multiply substituted with OH, F or COOC 1-4 -alkyl; C 4-6 -cycloalkyl; aryl or heteroaryl, unsubstituted or singly or multiply substituted with F, Cl, Br, CF 3 , OCH 3 , or branched or unbranched C 1-4 -alkyl; phenyl or heteroaryl bound via saturated or unsaturated C 1-3 alkyl, unsubstituted or singly or multiply substituted with F, Cl, Br, CF 3 , OCH 3 or branched or unbranched C 1-4 -alkyl; C 5-6 -cycloalkyl bound via saturated or unsaturated C 1-3 -alkyl; OR 13 ; or NR 14 R 15 ;
R 5 denotes H; COOR 13 , CONR 13 , OR 13 ; saturated or unsaturated, branched or unbranched C 1-5 -alkyl, unsubstituted or singly or multiply substituted with OH, F, CF 3 or CN;
R 6 denotes H; or
R 5 and R 6 together denote (CH 2 ) n where n=2, 3, 4, 5 or 6, wherein individual hydrogen atoms may be replaced by F, Cl, NO 2 , CF 3 , OR 13 , CN or C 1-5 -alkyl;
R 7 , R 8 , R 9 and R 10 independently of one another denote H; F; Cl; Br; NO 2 ; CF 3 ; OH; OCH 3 ; CN; COOR 13 ; NR 14 R 15 ; C 1-5 -alkyl; or heteroaryl, unsubstituted or singly or multiply substituted with benzyl, CH 3 , Cl, F, OCH 3 or OH; where
R 13 denotes H or C 1-5 -alkyl; and
R 14 and R 15 independently of one another denote H or C 1-5 -alkyl; and
X denotes O, S, SO, SO 2 or NR 17 ; where
R 17 denotes H; saturated or unsaturated, branched or unbranched C 1-5 -alkyl; COR 12 , or SO 2 R 12 ,
in the form of a pure stereoisomer or a mixture of stereoisomers in any mixing ratio, or a physiologically acceptable salt thereof
wherein said compound exhibits a ratio of ORL1 receptor affinity to μ-opioid receptor affinity of at least 0.3.
2 . A method according to claim 1 , wherein said compound is in the form of a pure enantiomer or diastereomer.
3 . A method according to claim 1 , wherein said compound is in the form of a racemic mixture.
4 . A method according to claim 1 , wherein said compound exhibits a ratio of ORL1 receptor affinity to μ-opioid receptor affinity of at least 1.
5 . A method according to claim 1 , wherein said compound exhibits a ratio of ORL1 receptor affinity to μ-opioid receptor affinity of at least 1.7.
6 . A method according to claim 1 , wherein R 3 denotes heteroaryl.
7 . A method according to claim 1 , wherein R 3 denotes phenyl, unsubstituted or singly or multiply substituted with F, OH, Cl or OCH 3 , or R 3 denotes benzyl.
8 . A method according to claim 1 , wherein W denotes NR 4 , and X denotes NR 17 .
9 . A method according to claim 1 , wherein W denotes NR 4 , and X denotes O.
10 . A method according to claim 1 , wherein said compound is selected from the group consisting of:
1 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
2 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2-nitrobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
3 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
4 1,1-(3-dimethylamino-3-(2-thienyl)pentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
5 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
6 1,1-(3-dimethylamino-3-phenylpentamethylene)-3,6-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
7 1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
8 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-hydroxymethyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
9 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2,3,4,5,6-pentafluoro-benzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
10 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(methoxycarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
11 1,1-(3-dimethylamino-3-phenylpentamethylene)-7-fluoro-1,3,4,9-tetrahydro-2,9-diazafluorene;
12 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2-aza-9-oxafluorene;
13 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
14 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-acetyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
15 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
16 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-chloro-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
17 1,1-(3-dimethylamino-3-(2-pyridyl)pentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
18 1,1-(3-dimethylamino-3-(3-thienyl)pentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
19 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-acetyl-7-fluoro-1,3,4,9-tetrahydro-2,9-diazafluorene;
20 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
21 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetra-hydropyrano[3,4-b]indole;
22 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2-thia-9-azafluorene;
23 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-6-nitro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
24 1,1-(3-dimethylamino-3-(3-thienyl)pentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
25 1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
26 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
27 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-oxo-1,3,4,9-tetrahydro-2-thia-9-azafluorene;
28 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2-thia-9-azafluorene;
29 1,1-(3-dimethylamino-3-(2-thienyl)pentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
30 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
31 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
32 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-hydroxy-1,3,4,9-tetrahydropyrano[3,4-b]indole;
33 1,1-(3-dimethylamino-3-(3-hydroxyphenyl)pentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
34 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2-thia-9-azafluorene;
35 6,6-(3-dimethylamino-3-phenylpentamethylene)-1,2,3,4,4a,6,7,11c-octahydro-5-oxa-7-aza-benzo[c]fluorine;
36 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
37 1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-2-acetyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
38 1,1-(3-dimethylamino-3-benzylpentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
39 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydro-2,9-diazafluorene;
40 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-methyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
41 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-bromo-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
42 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
43 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-bromo-1,3,4,9-tetrahydropyrano[3,4-b]indole;
44 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-methoxy-1,3,4,9-tetra-hydropyrano[3,4-b]indole;
45 1,1-(3-(1-Pyrrolidyl)-3-phenylpentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
46 1,1-(3-dimethylamino-3-phenylpentamethylene)-7,8-dichloro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
47 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-(1-benzyl-pyrazol-4-yl)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
48 1,1-(3-Methylamino-3-(2-thienyl)pentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
49 1,1-(3-Methylamino-3-(2-thienyl)pentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
50 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-cinnamoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
51 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,3-dimethylbutanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
52 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(cyclopentylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
53 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,3-dimethylbutanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
54 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(pentanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
55 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-furylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
56 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-furylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
57 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-fluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
58 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
59 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-methylbutanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
60 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(cyclohexylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
61 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-benzoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
62 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(cyclohexylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
63 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(phenylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
64 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
65 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(4-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
66 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(thien-2-ylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
67 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(phenylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
68 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-butanoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
69 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(4-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
70 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(3-fluoro-5-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
71 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,3-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
72 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
73 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-phenylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
74 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,4-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
75 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-cinnamoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
76 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,6-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
77 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-methoxycarbonylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
78 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-chlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
79 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-fluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
80 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2,6-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
81 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,4-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
82 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,3,4,5,6-pentafluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
83 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-cyclohexylcarbonyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
84 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-cyclopentylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
85 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-fluoro-3-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
86 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
87 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,4,5-trimethoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
88 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-cyclobutylcarbonyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
89 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,6-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
90 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
91 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-thienylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
92 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-propanoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
93 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,4-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
94 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,5-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
95 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-tert.butylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
96 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(3-methoxycarbonylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
97 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,4-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
98 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-ethylhexanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
99 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
100 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-phenylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
101 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-fluoro-5-trifluoro-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
102 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-fluoro-5-trifluoro-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
103 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-nitrobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
104 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,5-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
105 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
106 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,4-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
107 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(4-chlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
108 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
109 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,3,4,5-tetrafluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
110 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,6-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
111 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-furylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
112 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,4-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
113 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-methoxycarbonylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
114 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-chlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
115 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-fluoro-5-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
116 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-fluoro-4-trifluoro-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
117 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2-thienylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
118 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,6-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
119 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,4-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
120 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(3-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
121 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-methoxycarbonylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
122 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-fluoro-6-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
123 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
124 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,5-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
125 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2-furylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
126 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(pentanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
127 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(6-fluoro-2-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
128 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
129 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(4-tert.butylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
130 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(phenylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
131 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,5-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
132 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,3,4,5,6-pentafluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
133 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(3-nitrobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
134 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-nitrobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
135 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,3,4,5-tetrafluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
136 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-thienylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
137 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-fluoro-4-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
138 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-fluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
139 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(cyclobutylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
140 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
141 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2,5-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
142 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-bromobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
143 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-fluoro-5-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
144 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-fluoro-5-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
145 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2,3-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene, and
physiologically acceptable salts thereof.
11 . A method according to claim 1 , wherein said compound is selected from the group consisting of:
2 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2-nitrobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
8 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-hydroxymethyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
9 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2,3,4,5,6-pentafluoro-benzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
10 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(methoxycarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
11 1,1-(3-dimethylamino-3-phenylpentamethylene)-7-fluoro-1,3,4,9-tetrahydro-2,9-diazafluorene;
13 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
14 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-acetyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
17 1,1-(3-dimethylamino-3-(2-pyridyl)pentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
19 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-acetyl-7-fluoro-1,3,4,9-tetrahydro-2,9-diazafluorene;
20 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
25 1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
26 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
30 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
37 1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-2-acetyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
38 1,1-(3-dimethylamino-3-benzylpentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
39 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydro-2,9-diazafluorene;
40 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-methyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
50 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-cinnamoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
51 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,3-dimethylbutanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
52 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(cyclopentylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
53 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,3-dimethylbutanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
54 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(pentanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
55 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-furylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
56 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-furylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
57 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-fluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
58 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
59 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-methylbutanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
60 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(cyclohexylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
61 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-benzoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
62 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(cyclohexylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
63 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(phenylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
64 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
65 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(4-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
66 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(thien-2-ylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
67 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(phenylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
68 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-butanoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
69 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(4-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
70 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(3-fluoro-5-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
71 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,3-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
72 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
73 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-phenylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
74 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,4-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
75 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-cinnamoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
76 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,6-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
77 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-methoxycarbonylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
78 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-chlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
79 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-fluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
80 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2,6-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
81 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,4-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
82 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,3,4,5,6-pentafluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
83 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-cyclohexylcarbonyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
84 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-cyclopentylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
85 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-fluoro-3-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
86 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
87 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,4,5-trimethoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
88 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-cyclobutylcarbonyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
89 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,6-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
90 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
91 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-thienylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
92 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-propanoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
93 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,4-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
94 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,5-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
95 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-tert.butylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
96 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(3-methoxycarbonylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
97 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,4-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
98 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-ethylhexanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
99 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
100 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-phenylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
101 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-fluoro-5-trifluoro-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
102 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-fluoro-5-trifluoro-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
103 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-nitrobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
104 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,5-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
105 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
106 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,4-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
107 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(4-chlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
108 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
109 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,3,4,5-tetrafluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
110 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,6-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
111 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-furylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
112 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,4-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
113 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-methoxycarbonylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
114 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-chlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
115 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-fluoro-5-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
116 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-fluoro-4-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
117 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2-thienylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
118 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,6-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
119 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,4-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
120 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(3-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
121 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-methoxycarbonyl-propanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
122 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-fluoro-6-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
123 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
124 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,5-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
125 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2-furylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
126 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(pentanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
127 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(6-fluoro-2-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
128 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
129 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(4-tert.butylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
130 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(phenylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
131 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,5-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
132 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,3,4,5,6-pentafluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
133 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(3-nitrobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
134 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-nitrobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
135 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,3,4,5-tetrafluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
136 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-thienylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
137 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-fluoro-4-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
138 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-fluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
139 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(cyclobutylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
140 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
141 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2,5-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
142 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-bromobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
143 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-fluoro-5-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
144 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-fluoro-5-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
145 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2,3-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene, and
physiologically acceptable salts thereof.
12 . A method according to claim 1 , wherein said compounds is selected from the group consisting of:
8 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-hydroxymethyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
10 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(methoxycarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
11 1,1-(3-dimethylamino-3-phenylpentamethylene)-7-fluoro-1,3,4,9-tetrahydro-2,9-diazafluorene;
13 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
14 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-acetyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
17 1,1-(3-dimethylamino-3-(2-pyridyl)pentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
19 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-acetyl-7-fluoro-1,3,4,9-tetrahydro-2,9-diazafluorene;
20 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
25 1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
50 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-cinnamoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
51 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,3-dimethylbutanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
52 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(cyclopentylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
53 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,3-dimethylbutanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
54 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(pentanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
55 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-furylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
56 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-furylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
57 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-fluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
58 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
59 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-methylbutanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
60 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(cyclohexylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
61 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-benzoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
62 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(cyclohexylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
63 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(phenylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
64 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
65 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(4-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
66 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(thien-2-ylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
67 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(phenylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
68 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-butanoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
69 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(4-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
70 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(3-fluoro-5-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
71 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,3-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
72 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
73 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-phenylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
74 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,4-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
75 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-cinnamoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
76 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,6-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
77 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-methoxycarbonylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
78 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-chlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
79 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-fluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
80 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2,6-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
81 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,4-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
82 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,3,4,5,6-pentafluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
83 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-cyclohexylcarbonyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
84 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-cyclopentylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
85 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-fluoro-3-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
86 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
87 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,4,5-trimethoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
88 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-cyclobutylcarbonyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
89 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(2,6-dichlorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
90 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
91 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-thienylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
92 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-propanoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
93 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,4-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
94 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,5-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
95 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-tert.butylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
96 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(3-methoxycarbonylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
97 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,4-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
98 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-ethylhexanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
99 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
100 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-phenylpropanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
101 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3-fluoro-5-trifluoro-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
102 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-fluoro-5-trifluoro-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene, and
physiologically acceptable salts thereof.
13 . A method according to claim 1 , wherein said compound is selected from the group consisting of:
8 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-hydroxymethyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
10 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(methoxycarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
11 1,1-(3-dimethylamino-3-phenylpentamethylene)-7-fluoro-1,3,4,9-tetrahydro-2,9-diazafluorene;
13 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
14 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-acetyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
17 1,1-(3-dimethylamino-3-(2-pyridyl)pentamethylene)-1,3,4,9-tetrahydro-2,9-diazafluorene;
50 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-cinnamoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
51 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(3,3-dimethylbutanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
52 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(cyclopentylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
53 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3,3-dimethylbutanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
54 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(pentanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
55 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-furylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
56 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(2-furylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
57 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-fluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
58 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
59 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(3-methylbutanoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
60 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(cyclohexylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
61 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-benzoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
62 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(cyclohexylcarbonyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
63 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(phenylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
64 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-methoxybenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
65 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-(4-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
66 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(thien-2-ylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
67 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(phenylacetyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
68 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-butanoyl-1,3,4,9-tetrahydro-2,9-diazafluorene;
69 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(4-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
70 1,1-(3-dimethylamino-3-benzylpentamethylene)-2-(3-fluoro-5-trifluoromethylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
71 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(2,3-difluorobenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene;
72 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-2-(4-methylbenzoyl)-1,3,4,9-tetrahydro-2,9-diazafluorene, and
physiologically acceptable salts thereof.
14 . A method according to claim 1 , wherein said compound is selected from the group consisting of:
1 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
3 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
4 1,1-(3-dimethylamino-3-(2-thienyl)pentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
5 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
6 1,1-(3-dimethylamino-3-phenylpentamethylene)-3,6-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
7 1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
12 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2-aza-9-oxafluorene;
15 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
16 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-chloro-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
18 1,1-(3-dimethylamino-3-(3-thienyl)pentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
21 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetra-hydropyrano[3,4-b]indole;
23 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-6-nitro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
24 1,1-(3-dimethylamino-3-(3-thienyl)pentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
29 1,1-(3-dimethylamino-3-(2-thienyl)pentamethylene)-6-fluoro-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
31 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
32 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-hydroxy-1,3,4,9-tetrahydropyrano[3,4-b]indole;
33 1,1-(3-dimethylamino-3-(3-hydroxyphenyl)pentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
35 6,6-(3-dimethylamino-3-phenylpentamethylene)-1,2,3,4,4a,6,7,11c-octahydro-5-oxa-7-aza-benzo[c]fluorine;
36 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
41 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-bromo-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
42 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
43 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-bromo-1,3,4,9-tetrahydropyrano[3,4-b]indole;
44 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-methoxy-1,3,4,9-tetra-hydropyrano[3,4-b]indole;
45 1,1-(3-(1-Pyrrolidyl)-3-phenylpentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
46 1,1-(3-dimethylamino-3-phenylpentamethylene)-7,8-dichloro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
47 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-(1-benzyl-pyrazol-4-yl)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
48 1,1-(3-Methylamino-3-(2-thienyl)pentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
49 1,1-(3-Methylamino-3-(2-thienyl)pentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole, and
physiologically acceptable salts thereof.
15 . A method according to claim 1 , wherein said compound is selected from the group consisting of:
1 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
3 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
4 1,1-(3-dimethylamino-3-(2-thienyl)pentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
5 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
6 1,1-(3-dimethylamino-3-phenylpentamethylene)-3,6-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
7 1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
12 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2-aza-9-oxafluorene;
15 1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole;
16 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-chloro-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
18 1,1-(3-dimethylamino-3-(3-thienyl)pentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
21 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetra-hydropyrano[3,4-b]indole;
23 1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-6-nitro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
24 1,1-(3-dimethylamino-3-(3-thienyl)pentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
47 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-(1-benzyl-pyrazol-4-yl)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
48 1,1-(3-Methylamino-3-(2-thienyl)pentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole, and
physiologically acceptable salts thereof.
16 . A method according to claim 1 , wherein said compound is selected from the group consisting of:
22 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2-thia-9-azafluorene;
27 1,1-(3-dimethylamino-3-phenylpentamethylene)-2-oxo-1,3,4,9-tetrahydro-2-thia-9-azafluorene;
28 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2-thia-9-azafluorene;
34 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2-thia-9-azafluorene, and
physiologically acceptable salts thereof.
17 . A method according to claim 1 , wherein said compound is selected from the group consisting of:
1 1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole;
3 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole;
4 1,1-(3-dimethylamino-3-(2-thienyl)pentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indole, and physiologically acceptable salts thereof.
18 . A method according to claim 1 , wherein said substance dependency is opiate dependency.
19 . A method according to claim 1 , wherein said substance dependency is heroin, morphine or methadone dependency.
20 . A method according to claim 1 , wherein said compound is administered in combination with naloxone.
21 . A method according to claim 1 , wherein said compound is present in the form of a hydrochloride, citrate, methane sulfonate or hemicitrate salt.
22 . A method according to claim 1 , wherein said compound is present in the form of a non-polar diastereomer.Join the waitlist — get patent alerts
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