Novel 4-hydroxy-3-quinoline-carboxylates having analgesic and an

Details Novel 4-hydroxy-3-quinoline-carboxylates having analgesic and an Novel 4-hydroxy-3-quinoline-carboxylates having analgesic and an

1985-10-22

1988-04-05

Daus, Donald G.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514256, 546 89, 546309, 546156, 548195, A61K 3147, C07D21556

Patent

active

047359510

ABSTRACT:
Novel 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 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, 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 ##STR2## 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 and their non-toxic, pharmaceutically acceptable acid addition salts 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 having analgesic and anti-inflammatory activity.

REFERENCES:
patent: 4486438 (1984-12-01), Clemence et al.

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