N-aryl-1,2-dihydro-4-substituted-1-alkyl-2-oxo-quinoline-3-carboxamides
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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Abstract
This invention relates to novel heterocyclic carboxamides which increase the activity of the immune system and to the preparation thereof. The invention is also concerned with pharmaceutical compositions containing the said compounds and methods of treatment therewith.
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Citations
11 Claims
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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. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10)
- ##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;
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11. N-phenyl-N-methyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide.
Specification