Claims
- 1. A compound of the formula I wherein R1 is a group of the formula G1 whereinR6 is selected from hydrogen, (C1-C6) alkyl, and ((C2-C4)alkyl)aryl wherein the aryl moiety is phenyl or naphthyl, wherein said aryl moiety may optionally be substituted with one or more substituents independently selected from chloro, fluoro, bromo, iodo, (C1-C6)alkyl, (C1-C6)alkoxy, trifluoromethyl, cyano and SOg(C1-C6)alkyl wherein g is zero, one or two; x is zero to eight; each R13 is, independently, (C1-C4)alkyl; R2 is hydrogen, (C1-C4)alkyl, phenyl or naphthyl, wherein said phenyl or naphthyl may optionally be substituted with one or more substituents independently selected from chloro, fluoro, bromo, iodo, (C1-C6)alkyl, (C1-C6)alkoxy, trifluoromethyl, cyano and SOg(C1-C6)alkyl wherein g is zero, one or two; R3 is (CH2)mB, wherein m is zero, one, two or three and B is hydrogen, phenyl or naphthyl, wherein each of the foregoing aryl groups may optionally be substituted with one or more substituents independently selected from chloro, fluoro, bromo, iodo, (C1-C6)alkyl, (C1-C6)alkoxy, trifluoromethyl, cyano, hydroxy, COOH, and SOg(C1-C6)alkyl wherein g is zero, one or two; Z is CR4R5, wherein R4 and R5 are independently selected from hydrogen, (C1-C6)alkyl and trifluoromethyl and n is two; or Z is phenylene optionally substituted with one or more substituents independently selected from chloro, fluoro, bromo, iodo, (C1-C6)alkyl, (C1-C6)alkoxy, trifluoromethyl, cyano hydroxy, COOH, and SOg(C1-C6)alkyl wherein g is zero, one or two wherein two adjacent ring members of Z are also members of ring A and n is one; X is hydrogen, chloro, fluoro, bromo, iodo, cyano, (C1-C6)alkyl, hydroxy, trifluoromethyl, (C1-C6)alkoxy, —SOg(C1-C6)alkyl wherein g is zero one or two, CO2R10 or CONR11R12; each of R10, R11 and R12 is selected, independently, from the radicals set forth in the definition of R2; and the broken line indicates an optional double bond; or a pharmaceutically acceptable salt thereof.
- 2. A compound according to claim 1 wherein Z is CH2.
- 3. A compound according to claim 3 wherein n is two.
- 4. A compound according to claim 1, wherein R3 is substituted phenyl.
- 5. A compound according to claim 1, wherein said compound is selected from:3-[2-(4-methylpiperazin-1-yl)-benzylidene]-1,3-dihydro-indol-2-one; 6-chloro-3-[2-(4-methylpiperazin-1-yl)-benzylidene]-1,3-dihydro-indol-2-one; 5-chloro-3-[2-(4-methylpiperazin-1-yl)-benzylidene]-1,3-dihydro-indol-2-one; 1-methyl-3-[2-(4-methylpiperazin-1-yl)-benzylidene]-1,3-dihydro-indol-2-one; 3-[2-(4-methylpiperazin-1-yl)-benzylidene]-1-phenyl-1,3-dihydro-indol-2-one; 1-(3,4-dichlorophenyl)-3-[2-(4-methylpiperazin-1-yl)-benzylidene]-pyrrolidin-2-one; 1-(3,4-dichlorobenzyl)-3-[2-(4-methylpiperazin-1-yl)-benzylidene]-1,3-dihydro-indol-2-one; 1-(4-chlorobenzyl)-3-[2-(4-methylpiperazin-1-yl)-benzylidene]-pyrrolidin-2-one; 1-(4-chlorobenzyl)-3-[5-fluoro-2-(4-methylpiperazin-1-yl)-benzylidene]-pyrrolidin-2-one; 1-(3,4-difluorophenyl)-3-[2-(4-methylpiperazin-1-yl)-benzylidene]-pyrrolidin-2-one; 1-(2,4-dichlorobenzyl)-3-[2-(4-methylpiperazin-1-yl)-benzylidene]-pyrrolidin-2-one; 1-(3,4-dichlorophenyl)-3-[5-fluoro-2-(4-methylpiperazin-1-yl)-benzylidene]-pyrrolidin-2-one; 3-[2-(4-methylpiperazin-1-yl)-benzylidene]-1-phenyl-pyrrolidin-2-one; 3-[2-(4-methylpiperazin-1-yl)-benzylidene]-1-(4-trifluoromethylphenyl)-pyrrolidin-2-one; 1-(3,4-difluorophenyl)-3-[2-(4-methylpiperazin-1-yl)-benzyl]-pyrrolidin-2-one; 3-[2-(4-methylpiperazin-1-yl)-benzylidene]-pyrrolidin-2-one; 3-[5-fluoro-2-(4-methylpiperazin-1-yl)-benzylidene]-pyrrolidin-2-one; 3-[2-(4-methylpiperazin-1-yl)-benzyl]-1-phenyl-pyrrolidin-2-one; 3-[2-(4-methylpiperazin-1-yl)-benzylidene]-1-(p-tolyl)-pyrrolidin-2-one; 3-[4-fluoro-2-(4-methylpiperazin-1-yl)-benzylidene]-1-phenyl-pyrrolidin-2-one; 1-(3,4-dichlorophenyl)-3-[2-fluoro-6-(4-methylpiperazin-1-yl)-benzylidene]-pyrrolidin-2-one; 3-[2-(4-methylpiperazin-1-yl)benzyl]-1-(4-trifluoromethylphenyl)-pyrrolidin-2-one; and pharmaceutically acceptable salts thereof.
- 6. A pharmaceutical composition comprising an amount of a compound according to claim 1 and a pharmaceutically acceptable carrier.
- 7. A method for treating or preventing a disorder or condition selected from depression, generalized anxiety disorder, phobias, posttraumatic stress syndrome, obsessive-compulsive disorder, and panic disorder in a mammal, comprising administering to a mammal in need of such treatment or prevention an amount of a compound according to claim 1.
Parent Case Info
This application claims the benefit of provisional application No. 06/015,134 filed Mar. 29, 1996.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/IB97/00076 |
|
WO |
00 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO97/36867 |
10/9/1997 |
WO |
A |
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Provisional Applications (1)
|
Number |
Date |
Country |
|
60/015134 |
Mar 1996 |
US |