Heteroarylpiperidines, pyrrolidines and piperazines and their use as antipsychotics and analetics

  • US 5,364,866 A
  • Filed: 10/30/1992
  • Issued: 11/15/1994
  • Est. Priority Date: 05/19/1989
  • Status: Expired
First Claim
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1. A compound of the formula:

  • ##STR163## wherein X is --O-- or --S--;

    p is 1 or 2;

    Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1;

    Y is lower alkoxy, hydroxy and halogen when p is 2 and X is --O--;

    (R1) is R20, R21, or R22, wherein;

    R20 is --(CH2)n -- where n is 2, 3, 4 or 5;

    R21 is--CH2 --CH═

    CH--CH2 --,--CH2 --C≡

    C--CH2 --,--CH2 --CH═

    CH--CH2 --CH2,--CH2 --CH2 --CH═

    CH--CH2 --,--CH2 C≡

    C--CH2 --CH2 --, or--CH2 --CH2 --C≡

    C--CH2 --,the --CH═

    CH-- bond being cis or trans;

    R22 is R20 or R21 in which one or more carbon atoms of R20 or R21 are substituted by at least one C1 -C6 linear alkyl group, phenyl group or ##STR164## where Z1 is lower alkyl, --OH, lower alkoxy, --CF3, --NO2, --NH2 or halogen;

    R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, formyl, ##STR165## alkyl is lower alkyl;

    aryl is phenyl or ##STR166## where R5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy;

    heteroaryl is ##STR167## Q3 is --O--, ##STR168## --CH═


    W is CH2 or CHR8 or N--R9 ;

    R7 is hydrogen, lower alkyl, or acyl;

    R8 is lower alkyl;

    R9 is hydroxy, lower alkoxy, or --NHR10 ; and

    R10 is hydrogen, lower alkyl, C1 -C3 acyl, aryl, ##STR169## where aryl and heteroaryl are as defined above; and

    m is 1, 2, or 3;

    all geometric, optical and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof.

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