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

CAFC
  • US RE39,198 E1
  • Filed: 11/15/2000
  • Issued: 07/18/2006
  • Est. Priority Date: 05/19/1989
  • Status: Expired due to Term
First Claim
Patent Images

1. A compound of the formula:

  • embedded imagewhereinX 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, pheny group or embedded imagewhere 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, —

    C(═

    O)-alkyl, —

    C(═

    O)—

    O-alkyl, —

    C(═

    O)-aryl, —

    C(═

    O)-heteroaryl, —

    CH(OR7)-alkyl, —

    C(═

    W)-alkyl, —

    C(═

    W)-aryl, and —

    C(═

    W)-heteroaryl;

    or —

    CH(OR7)-alkyl;

    wherein alkyl is lower alkyl;

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

    heteroaryl is embedded imagewherein Q3 is —

    O—

    , —

    S—

    , —

    NH—

    , or —

    CH═

    N—

    ;

    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, —

    C(═

    )-aryl or —

    C(═

    O)-heteroaryl, where aryl and heteroaryl are as defined above;

    andm is 1, 2, or 3;

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

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