Quinolyloxazole-2-ones useful as proteinkinase c inhibitors

Details Quinolyloxazole-2-ones useful as proteinkinase c inhibitors Quinolyloxazole-2-ones useful as proteinkinase c inhibitors

C - Chemistry, Metallurgy

07

D

167/226, 260/277

C07D 215/14 (2006.01) A61K 31/47 (2006.01) C07D 413/04 (2006.01)

Patent

CA 2000804

This invention relates to novel quinolyloxazole-2-ones of the formula: (see fig. I) wherein R and R1 are each independently selected from the group consisting of hydrogen, C1-C6 alkyl, and C1-C3 alkylphenyl wherein the phenyl ring is optionally substituted with one, two or three of the substituents selected from the group consisting of fluorine, chlorine, bromine, C1-C4 alkyl, and C1-C4 alkoxy; and R2 is a 2-, 3-, or 4-quinolyl group, optionally substituted with one, two or three of the substituents selected from the group consisting of fluorine, chlorine, bromine, C1-C4 alkyl, C1-C4 alkoxy, nitro and trifluoromethyl, or R2 is a 5-, 6-, 7-, or 8-quinolyl group; which are useful as protein kinase C inhibitors, effective in the treatment of hypertension and asthma. This invention also includes a novel procedure for producing an intermediate ketone compound involving the reaction of a bromo-quinoline compound with butyl lithium and further reacting the lithiated compound with N-methyl-N-methoxyalkanamide.

Cette invention porte sur de nouvelles quinolyloxazol-2-ones de formule (voir fig. I), où : R et R1 sont choisis chacun indépendamment parmi un hydrogène, un alkyle C1-C6 et un alkyle C1-C3 phényle, le phényle étant facultativement avec substitution par un, deux ou trois substituants choisis parmi le fluor, le chlore, le brome, un alkyle C1-C4 et un alcoxy C1-C4; R2 est un groupe 2-, 3- ou 4-quinolyle, facultativement avec substitution par un, deux ou trois substituants choisis parmi le fluor, le chlore, le brome, un alkyle C1-C4, un alcoxy C1-C4, un nitro et un trifluorométhyle; ou bien R2 est un groupe 5-, 6-, 7- ou 8-quinolyle. Elles sont utiles comme inhibiteurs de la protéine-kinase C, efficaces pour le traitement de l'hypertension et de l'asthme. Cette invention concerne également une nouvelle méthode pour produire une cétone intermédiaire, consistant à faire réagir une bromo-quinoléine avec du butyllithium, puis à faire réagir le composé lithié avec un N-méthyl-N-méthoxyalcanamide.

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