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Muscarinic antagonists

  • US 5,935,958 A
  • Filed: 06/26/1997
  • Issued: 08/10/1999
  • Est. Priority Date: 07/01/1996
  • Status: Expired due to Fees
First Claim
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1. A compound having the structural formula ##STR41## or a stereoisomer thereof, or a pharmaceutically acceptable salt, or solvate thereof,wherein:

  • Z is N;

    X is --O--, --S--, --SO--, --SO2 --, --CO--, --CH2 --, --CONR20 --, --NR20 --SO2 --, --NR20 CO--, or --SO2 --NR20 --;

    Q is --O--, --S--, --SO--, --SO2 --, or --CH2 --;

    R is ##STR42## R1 and R21 are independently selected from the group consisting of hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, phenylalkyl, and hydroxyalkyl;

    R2 is cycloalkyl, cycloalkyl substituted with 1 to 3 independently selected R3 groups, cycloalkenyl, cycloalkylalkyl, ##STR43## (wherein Ry is H, alkyl, alkenyl, SO2 Rz or CORz wherein Rz is alkyl, aryl or cycloalkyl);

    R3, R4, R5, R6, R22, R24, and R25 are independently selected from the group consisting of H, alkyl, halo, alkoxy, benzyloxy, benzyloxy substituted by nitro or aminoalkyl, polyhaloalkyl, nitro, hydroxy, amino, alkylamino, formyl, alkylthio, acyloxy, alkylsulfonyl, arylsulfonyl, acyl, alkoxycarbonyl, alkylsulfinyl, --OCONH2, --OCONH-- alkyl, --OCON(alkyl)2, --NHCOO-- alkyl, --NHCO-- alkyl, phenyl, hydroxyalkyl, and 1-morpholinyl;

    R8 is hydrogen, lower alkyl or cyclopropyl;

    R20 is H, phenyl or alkyl; and

    R27 and R28 are independently selected from the group consisting of H, alkyl, hydroxyalkyl, alkoxyalkyl, arylalkyl, mercaptoalkyl, alkylthioalkyl, and carboxyalkyl, and additionally R27 and R28 may be joined to form an alkylene group; and

    n is 0 or an integer from 1 to 3.

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