Pyrazolopyrimidinones for the treatment of impotence

CAFC
  • US 6,469,012 B1
  • Filed: 03/04/1996
  • Issued: 10/22/2002
  • Est. Priority Date: 06/09/1993
  • Status: Expired due to Term
First Claim
Patent Images

1. A method of treating erectile dysfunction in a male animal, comprising administering to a male animal in need of such treatment an effective amount of a compound of formula (I):

  • embedded imagewherein;

    R1 is H;

    C1-C3 alkyl;

    C1-C3 perfluoroalkyl;

    or C3-C5 cycloalkyl;

    R2 is H;

    C1-C6 alkyl optionally substituted with C3-C6 cycloalkyl;

    C1-C3 perfluoroalkyl;

    or C3-C6 cycloalkyl;

    R3 is C1-C6 alkyl optionally substituted with C3-C6 cycloalkyl;

    C1-C6 perfluoroalkyl;

    C3-C5 cycloalkyl;

    C3-C6 alkenyl;

    or C3-C6 alkynyl;

    R4 is C1-C4 alkyl optionally substituted with OH, NR5R6, CN, CONR5R6 or CO2R7;

    C2-C4 alkenyl optionally substituted with CN, CONR5R6 or CO2R7;

    C2-C4 alkanoyl optionally substituted with NR5R6;

    (hydroxy)C2-C4 alkyl optionally substituted with NR5R6;

    (C2-C3 alkoxy)C1-C2 alkyl optionally substituted with OH or NR5R6;

    CONR5R6;

    CO2R7;

    halo;

    NR5R6;

    NHSO2NR5R6;

    NHSO2R8;

    SO2NR9R10;

    or phenyl pyridyl, pyrimidinyl, imidazolyl, oxazolyl, thiazolyl, thienyl or triazolyl any of which is optionally substituted with methyl;

    R5 and R6 are each independently H or C1-C4 alkyl, or together with the nitrogen atom to which they are attached form a pyrrolidinyl, piperidino, morpholino, 4-N(R11)-piperazinyl or imidazolyl group wherein said group is optionally substituted with methyl or OH;

    R7 is H or C1-C4 alkyl;

    R8 is C1-C3 alkyl optionally substituted with NR5R6;

    R9 and R10 together with the nitrogen atom to which they are attached form a pyrrolidinyl, piperidino, morpholino or 4-N(R12)-piperazinyl group wherein said group is optionally substituted with C1-C4 alkyl, C1-C3 alkoxy, NR13R14 or CONR13R14;

    R11 is H;

    C1-C3 alkyl optionally substituted with phenyl;

    (hydroxy)C2-C3 alkyl;

    or C1-C4 alkanoyl;

    R12 is H;

    C1-C6 alkyl;

    (C1-C3 alkoxy)C2-C6 alkyl;

    (hydroxy)C2-C6 alkyl;

    (R13R14N)C2-C6 alkyl;

    (R13R14NOC)C1-C6 alkyl;

    CONR13R14;

    CSNR13R14;

    or C(NH)NR13R14; and

    R13 and R14 are each independently H;

    C1-C4 alkyl;

    (C1-C3 alkoxy)C2-C4 alkyl;

    or (hydroxy)C2-C4 alkyl;

    or a pharmaceutically acceptable salt thereof;

    or a pharmaceutically acceptable composition containing either entity.

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