FORFARANDE FOR FRAMSTELLNING AV OXAZOLO-(5,4-B)-PYRIDINER

1421619 Oxazolo- and thiazolo-pyridines MERCK & CO Inc 11 June 1973 [14 June 1972] 27632/73 Heading C2C The invention comprises novel compounds (I) in which the six membered ring is a pyridine with the N at one of the unsubstituted positions, or an N-oxide or quaternary pyridinium salt thereof, in which Y is O or S, R is (a) where n is 0, 1, 2, 3, 4 or 5 and, when n is 2 or more, the X substituents are similar or dissimilar, X is a halogen atom or a C 1-3 alkoxy, C 1-5 alkyl, nitro, phenyl, C 1-3 alkylsulphonyl, C 1-3 trihaloalkyl, cyano, C 1-3 alkylthio, carbamoyl, symmetrical or asymmetrical di- (C 1-3 alkyl)amino, C 1-3 alkylamino, C 1-3 alkylsulphinyl, mercapto, trifluoromethoxy, C 2-5 alkanoyloxy, hydroxy, C 2-5 alkanoylamino, amino, benzoylamine, halobenzoylamino, (C 1-3 alkyl) benzoylamine or (C 1-3 alkoxy)- benzoylamino radical, or a radical of formula -COOR2, -(CH 2 ) w COOR2 or -(CH 2 ) w CN, in which w is 1, 2 or 3 and each R2, which may be the same as or different from any other R2, is hydrogen or C 1-3 alkyl; or two X radicals on adjacent carbons are linked together to form a methylenedioxy group; or (b) (c) a 5-6 membered heterocycle containing up to 2 heteroatoms selected from O, N and S; (d) naphthyl or (e) adamantanyl; R1 is a halogen atom or a C 1-5 alkyl, nitro, C 1-3 trihaloalkyl, amino, benzoylamine, C 1-3 alkoxy, symmetrical or asymmetrical di(C 1-3 alkyl)amino, C 1-3 alkylamine, phenyl, (C 1-3 alkoxy)-carbonylamine, or cyano group; and m is 0, 1 or 2 with the proviso that R is not phenyl, 4-halophenyl, 4-(C 1-3 alkoxy)phenyl, 4-(C 1-5 alkyl)phenyl, 4-nitrophenyl or 4-aminophenyl. They are made by standard methods by cyclization of corresponding amino-hydroxy-pyridines or mercaptoaminopyridines; intermediate amides can be isolated and subsequently either ring closed to give the oxazolo-pyridines, or treated with P 2 S 5 to give the thiazolo-pyridines. Pharmaceutical preparations having antiinflammatory, antipyretic and analgesic actions contain (I) as above defined, but without the proviso, and/or (I) where R can also be (where A is C 1-3 alkylene or C 2-5 alkenylene), C 1-5 alkyl or C 3-7 cycloalkyl, as active ingredient. Standard forms of administration are described.