Anti-inflammatory 2-substituted-4-hydroxy-3-quinoline carboxamid

Details Anti-inflammatory 2-substituted-4-hydroxy-3-quinoline carboxamid Anti-inflammatory 2-substituted-4-hydroxy-3-quinoline carboxamid

1985-06-25

1987-01-13

Warden, Robert J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514275, 546156, 544322, A61K 3147, C07D21522

Patent

active

046365125

ABSTRACT:
Novel racemates or optically active forms of 2-amino-4-hydroxy-3-quinoline carboxylic acid derivatives 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 --, CF.sub.3 S-- and CF.sub.3 O--, 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 (a) thiazolyl, 4,5-dihydrothiazolyl, pyridinyl, oxazolyl, isoxazolyl, imidazolyl, pyrimidyl and tetrazolyl, each optionally substituted with alkyl of 1 to 4 carbon atoms and (b) phenyl optionally substituted with at least one member of the group consisting of hydroxy, alkyl and alkoxy of 1 to 4 carbon atoms, CF.sub.3 --, --NO.sub.2 and halogen, R.sub.3 is selected from the group consisting of 2-pyrrolidinyl of the formula ##STR2## R.sub.4 is selected from the group consisting of hydrogen, an amino protective group and ##STR3## R'4 is selected from the group consisting of alkyl 1 to 5 carbon atoms optionally substituted with amino or protected amino, aryl and aralkyl, R.sub.5 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, aryl, aralkyl, p-hydroxy-benzyl, lH-indol-3-yl methyl of the formula and --CH.sub.2 SH, the last three being optionally protected by a blocking group and their non-toxic, pharmaceutically acceptable acid addition salts having analgesic and anti-inflammatory activity and novel intermediates.

REFERENCES:
patent: 3992540 (1976-11-01), Clemence
patent: 4107310 (1978-08-01), Allais
patent: 4299831 (1981-11-01), Clemence
patent: 4450166 (1984-05-01), Clemence
patent: 4523942 (1985-06-01), Hamprecht
Clemence Chemical Abstracts 100:138971g (12/8/83).

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