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Heterocyclic carboxamides, compositions containing such compounds, processes for their preparation and methods of treatment therewith

  • US 4,547,511 A
  • Filed: 02/22/1982
  • Issued: 10/15/1985
  • Est. Priority Date: 03/03/1981
  • Status: Expired due to Term
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First Claim
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1. A method of treating a living animal body in order to enhance cell-mediated immunity comprising administering to said animal body a compound having the formula:

  • ##STR11## or a tautomer thereof, wherein the groups A1 and A2 are interchanged and there is a 2,3- rather than a 3,4-double bond;

    where R1, R2 and R3 are the same or different and selected from the group consisting of;

    hydrogen;

    lower alkyl;

    lower alkoxy;

    halogen;

    OH;

    OCOR8 ;

    NR6 R7 ; and

    NR6 COR8 ; and

    where R1 and R2 or R2 and R3 together may also be in the form of a methylenedioxy group;

    and where only one of R1, R2, and R3 may be NO2 ;

    where R4 is selected from the group consisting of;

    lower alkyl;

    lower alkenyl;

    cycloalkyl optionally mono- or disubstituted with a substituent selected from the group consisting of lower alkyl, lower alkoxy, OH and OCOR8 ; and

    phenyl optionally mono- or disubstituted with a substituent selected from the group consisting of lower alkyl, lower alkoxy and halogen, and wherein R5 is selected from the group consisting of a five- or six-membered heterocyclic ring containing at most two heteroatoms selected from the group consisting of S and N, and being optionally mono- or disubstituted with substituents selected from the group consisting of lower alkyl, lower alkoxy and halogen, and R5 is further selected from the group;

    ##STR12## wherein R9, R10 and R11 are the same or different and selected from the group consisting of;

    hydrogen;

    lower alkyl;

    lower alkenyl;

    lower alkoxy;

    lower alkylthio;

    halogen;

    CN;

    SO2 CH3 ;

    OH;

    OCOR8 ;

    NR6 R7 ;

    NR6 COR8 ;

    COOR12 ;

    OCH2 COOR12 ;

    CH2 COOR12 ;

    COR8 ; and

    ##STR13## wherein m is four or five; and

    where R9 and R10 or R10 and R11 together also may be in the form of a methylenedioxy group;

    wherein A1 is selected from the group consisting of OR12, OCOR8, NR6 R7 and NR6 COR8 and A2 is selected from the group consisting of O and NR6 ;

    wherein R6 and R7 are selected from the group consisting of hydrogen and lower alkyl;

    wherein R8 is lower alkyl;

    wherein R12 is selected from the group consisting of lower alkyl and M; and

    wherein M is selected from the group consisting of hydrogen and pharmaceutically-acceptable inorganic cations; and

    wherein R13 is selected from the group consisting of hydrogen, lower alkyl optionally substituted with a substituent selected from the group consisting of OH, OR8 and OCOR8, and lower alkenyl;

    provided that R13 is selected from the group consisting of lower alkyl optionally substituted with a substituent selected from the group consisting of OH, OR8 and OCOR8, and lower alkenyl when ##STR14## and R9, R10 and R11 are selected from the group consisting or lower alkyl, lower alkenyl and lower alkoxy; and

    addition salts with pharmaceutically acceptable inorganic or organic acid;

    the term "lower" when used herein meaning in each case that the group referred to may be straight or branched and contains 1 to 4 carbon atoms, inclusive, to said animal body in an amount effective for said purpose.

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