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Cis-2-[(4-heteroaryl-1-piperazinyl)alkyl] hexahydro-1H-isoindole-1,3 (2H)-diones and related compounds and their therapeutic utility

  • US 5,556,858 A
  • Filed: 06/06/1995
  • Issued: 09/17/1996
  • Est. Priority Date: 05/19/1989
  • Status: Expired due to Fees
First Claim
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1. A compound of the formula:

  • ##STR132## X is --O--, --S--, --NH--, or --N(R2);

    R2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (3 -C10) cycloalkyl, aroyl, (C2 -C18) alkanoyl, (C1 -C18) alkoxycarbonyl, and phenylsulfonyl groups;

    aryl is as defined hereinafter;

    p is 1 or 2;

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

    R1 is --CR24 R27 --(CR23 R27)n --, where n is 0,1,2 or 4;

    or--CHR24 CH═

    CH--CHR24 --,--CHR24 --C.tbd.C--CHR24 --,--CHR24 --CH═

    CH--CR23 R24 --CHR24 --,--CHR24 --CR23 R24 --CH.tbd.CH--CHR24 --,--CHR24 --C.tbd.C--CR23 R24 --CHR24 --, or--CHR24 --CR23 R24 --C.tbd.C--CHR24,the --CH═

    CH-- bond being cis or trans;

    R23 is hydrogen, (C1 -C18) linear alkyl, phenyl, hydroxy, (C1 -C18)alkoxy, aryloxy, aryl (C1 -C18)alkyloxy, (C1 -C18)alkanoyloxy, hydroxy (C1 -C6)alkyl, (C1 -C18)alkoxy(C1 -C6) alkyl, phenyl (C1 -C6)alkyloxy, aryl (C1 -C18) alkyloxy (C1 -C6)alkyl or (C1 -C18)alkanoyloxy (C1 -C6) alkyl or ##STR133## where Z1 is lower alkyl, --OH, lower alkoxy, --CF3, --NO2, --NH2, or halogen, and p is as previously defined;

    R24 is hydrogen, (C1 -C18) linear alkyl, phenyl, hydroxy (C1 -C6)alkyl, (C1 -C18)alkoxy(C1 -C6)alkyl, phenyl (C1 -C6)alkyloxy, aryl (C1 -C18) alkyoxy(C1 -C6) alkyl, (C1 -C18) alkanoyloxy (C1 -C6)alkyl or ##STR134## where Z1 and p are as previously defined;

    R27 is hydrogen or R24 and R27 taken together with the carbon to which they are attached form C═

    O or C═

    S;

    and aryl is phenyl or ##STR135## where R5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, or trifluoromethoxy; and

    , any hydroxyl group attached to an aliphatic or aromatic carbon atom, or any primary or secondary nitrogen atom may be acylated with a (C4 -C18)carboxylic group, in addition, any nitrogen atom may alternatively be acylated with a (C4 -C18)alkoxycarbonyl group;

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

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