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N-aryl-1,2-dihydro-4-substituted-1-alkyl-2-oxo-quinoline-3-carboxamides

  • US 4,738,971 A
  • Filed: 04/16/1985
  • Issued: 04/19/1988
  • Est. Priority Date: 03/03/1981
  • Status: Expired due to Term
First Claim
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1. 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;

    R1, R2 and R3 are independentlyselected 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 methylenedixoy 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;

    ##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 and organic 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 R5 is ##STR14## and R9, R10, and R11 are selected from the group consisting of lower alkyl, lower alkenyl and lower alkoxy; and

    addition salts with pharmaceutically-acceptable inorganic or organic acids;

    the term "lower" when used herein meaning in each case that the group referred to may be straight or branched and contains one to four carbon atoms, inclusive.

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