Alkanoic acid 2-quinoline derivatives
AssigneeImperial Chemical Industries PLC
InventorsDavid Robert Brittain, Edward Douglas Brown, Walter Hepworth, Gilbert Joseph Stacey
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Abstract
Novel 1,2-dihydro-2-oxoquinol-4-ylalkanoic acid derivatives bearing a variety of substituents on the quinoline nucleus but including, at position 1, an aromatic radical linked directly or through a C.sub.1-4 -alkylene or a C.sub.2-4 -alkenylene radical. Representative compounds of the invention are 1-(3,4-dichlorobenzyl)-3-methyl-1,2-dihydro-2-oxoquinol-4-ylacetic acid and .alpha.-(1-benzyl-1,2-dihydro-2-oxoquinol-4-yl)propionic acid. The compounds possess anti-inflammatory or analgesic properties, or are inhibitors of the enzyme aldose reductase.
Claims5
A compound selected from the group consisting of .alpha.-[1(4-ethylbenzyl)-1,2-dihydro-2-oxoquinol-4-yl]propionic acid, .alpha.-[1-(4-trifluoromethylbenzyl)-1,2-dihydro-2-oxoquinol-4-yl]propioni c acid, .alpha.-(1-benzyl-7-methyl-1,2-dihydro-2-oxoquinol-4-yl)propionic acid, .alpha.-(1-benzyl-6-methyl-1,2-dihydro-2-oxoquinol-4-yl)propionic acid, .alpha.-[1-(-4-trifluoromethylbenzyl)-6-methyl-1,2-dihydro-2-oxoquinol-4-y l]propionic acid, .alpha.-[1-(4-chlorobenzyl)-6-methyl-1,2-dihydro-2-oxoquinol-4-yl]propioni c acid, .alpha.-(1-benzyl-1,2-dihydro-2-oxoquinol-4-yl)propionic acid, .alpha.-[1-(4-methylbenzyl)-1,2-dihydro-2-oxoquinol-4-yl]propionic acid, .alpha.[1-(4-methylbenzyl)-6-methyl-1,2-dihydro-2-oxoquinol-4-yl]-propioni c acid, and the pharmaceutically acceptable base addition salts thereof.
A quinolone alkanoic acid derivative of the formula:
- ##STR21## wherein A is a methylene, ethylene or propenylene radical;
- R.sup.1 is hydrogen;
- R.sup.2 is methyl;
- R.sup.3 is hydroxy, amino, hydroxylamino, C.sub.1-6 alkoxy or phenoxy;
- and wherein the benzene ring X is unsubstituted or bears either a single substituent selected from the group consisting of halogen atoms, methyl, methoxy, nitro and amino or two methyl substituents;
- and wherein the ring Y is phenyl which may optionally bear a single substituent selected from the group consisting of halogen, methyl, methoxy, methylthio and trifluoromethyl;
- or a pharmaceutically-acceptable salt thereof.
Dependencies are inferred from the claim text.