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1-substituted-4-(thiazolyl-2-)-piperazines, -piperidines and -tetrahydropyridines useful as anxiolytic, psychogeriatric, antidepressant and antischizophrenic agents

  • US 4,737,500 A
  • Filed: 06/20/1986
  • Issued: 04/12/1988
  • Est. Priority Date: 06/22/1985
  • Status: Expired due to Fees
First Claim
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1. A compound of formula I:

  • ##STR89## wherein R1 and R2, independently, are hydrogen, (C1-6)alkyl, (C3-6)cycloalkyl, (C3-6)cycloalkyl(C1-3)alkyl, phenyl, phenyl(C1-3)alkyl, orR1 and R2 signify together trimethylene, tetramethylene or pentamethylene, optionally substituted at the same of different carbon atoms by 1 or 2 methyl groups, orR1 and R2 signify together --(CH3)2 C--O--C(CH3)2 --,R1 may additionally signify trifluoromethyl;

    W is alkylene of 2 to 6 carbon atoms, or alkenylene or alkynylene of 4 to 6 carbon atoms, whereby the unsaturation is not adjacent to the nitrogen atoms; and

    R3 is a group of formulae (a)-(n) ##STR90## m is 0 or 1, R4 and R4 '"'"' independently are hydrogen or (C1-4)alkyl,R5 and R5 '"'"' independently are hydrogen, (C1-4)alkyl, phenyl or phenyl(C1-4)alkyl,t is 4 or 5,R6 is hydrogen or (C1-3)alkyl, andR7 is hydrogen, (C1-3)alkyl, phenyl(C1-3)alkyl or phenoxy(C1-3)alkyl,or R3 is a group of formula (o) ##STR91## in which R8 is hydrogen or (C1-3)alkyl,R9 is --COR10, --CON(R11)R12, --SO2 R10 or --SO2 N(R11)R12, wherein R10 is (C1-6)alkyl, (C3-6)cycloalkyl, phenyl or phenyl(C1-3)alkyl, wherein each phenyl is optionally mono- or independently di- or trisubstituted by (C1-3)alkyl, hydroxy, methoxy, methylenedioxy, amino, chloro, fluoro or trifluoromethyl, andR11 and R12 are each, independently, hydrogen or (C1-3)alkyl orR11 and R12 together signify tetramethylene or pentamethylene,provided that when W is dimethylene and R9 is --COR10, wherein R10 is 4-aminophenyl, at least one of R1, R2 and R8 is other than hydrogen,or a pharmaceutically acceptable acid addition salt thereof.

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