4-OH-quinoline carboxylic acid amides having analgesic and anti-

Details 4-OH-quinoline carboxylic acid amides having analgesic and anti- 4-OH-quinoline carboxylic acid amides having analgesic and anti-

1987-03-24

1989-07-04

Sutto, Anton H.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514256, 544322, 544 92, 546156, 546 89, 548195, A61K 3147, C07D21556

Patent

active

048451053

ABSTRACT:
A compound selected from the group consisting of optical isomers and racemates of 4-hydroxy-3-quinoline carboxylates of the formula ##STR1## wherein X is in the 5-, 6-, 7- or 8-position and is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, --CF.sub.3, --SCF.sub.3 and --OCF.sub.3, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.2 is selected from the group consisting of thiazolyl, 4,5-dihydrothiazolyl, pyridinyl, oxazolyl, isoxazolyl, imidazolyl, pyrimidyl and tetrazolyl, all optionally substituted with alkyl of 1 to 4 carbon atoms and phenyl and phenyl substituted with at least one member of the group consisting of --OH, alkyl and alkoxy of 1 to 4 carbon atoms, --CF.sub.3, --NO.sub.2 and halogen, A is either ##STR2## in which R.sub.3 and R.sub.4 are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and aryl, R.sub.5 is selected from the group consisting of aryl of 6 to 14 carbon atoms, heteroaryl of 3 to 14 carbon atoms, alkyl of 1 to 14 carbon atoms, alkyl substituted with --NH.sub.2, --NHAlk or ##STR3## alkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms substituted with aryl of 6 to 14 carbon atoms, Alk and Alk' are alkyl of 1 to 6 carbon atoms or, when R.sub.1 is hydrogen, A is ##STR4## and R.sub.3a are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, aryl and ##STR5## or R.sub.2a and R.sub.3a together form acetonide, R.sub.4a is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and aryl, R.sub.5a is selected from the group consisting of alkyl of 1 to 4 carbon atoms and aryl with the proviso that when X is 8--CF.sub.3, R.sub.1 and R.sub.3 are hydrogen, R.sub.2 is 2-thiazolyl, R.sub.4 is methyl, R.sub.5 is not methyl and their non-toxic, pharmaceutically acceptable salts with acids or bases having analgesic and anti-inflammatory activity.

REFERENCES:
patent: 4486438 (1984-12-01), Clemence et al.
patent: 4636512 (1987-01-01), Clemence et al.
patent: 4735951 (1988-05-01), Clemence et al.
Clemence et al., J. Heterocycl. Chem., 21(5), pp. 1345-1353, (1984).

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