GB1288647A - - Google Patents

Abstract

1288647 Benzylideneamino-hydroxyalkanoic acid derivatives PHILIPS GLOEILAMPENFABRIEKEN NV 12 Dec 1969 [17 Dec 1968] 60748/69 Heading C2C Novel benzylideneamino - hydroxyalkanoic acid derivatives of the general formula wherein R 1 is a halogen atom, R 2 is a hydrogen or halogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom or methyl group, with the proviso that when R 4 is a hydrogen atom, then R 5 is a C 1-8 alkoxy group, R 5 is a C 1-3 alkylene group and R 6 is a hydroxyl, C 1-8 alkoxy, amino, mono-C 1-3 alkyl-amino, benzyloxy or OR, group, where R 7 is a metal atom or an ammonium, 2-hydroxyethyldimethylammonium or 2- hydroxyethyldiethylammonium group, are prepared (a) when R 6 is a hydroxyl, amino, mono- C 1-3 alkyl-amino, C 1-8 alkoxy or benzyloxy group, by reaction of an oxime salt of the general formula wherein M is a metal atom, with a compound of the general formula Hal-R 5 -CO-R 6 , wherein Hal is a halogen atom; (b) by reaction of an aldehyde or ketone of the general formula with a compound of the general formula (c) when R 6 is a hydroxyl group or a group of the formula OR 7 wherein R 7 is a metal atom and R 5 is a C 2-3 alkylene group, by reaction of an oxime salt of the second general formula above with a lactone of the general formula wherein R 5 <SP>1</SP> is a C 2-3 alkylene group; (d) when R 5 is a C 2-3 alkylene group, by reaction of an oxime salt of the second general formula above with a compound of the general formula R 5 <SP>11</SP>-CO-R 6 , wherein R 5 <SP>11</SP> is an ethenyl or propen-1-yl 1, 2 or 3 group; (e) when R 6 is as in (c), by saponification of a nitrile of the general formula with a base; (f) when R 6 is a C 1-8 alkoxy or benzyloxy group, by reaction of a nitrile as defined in (e) with a C 1-8 alkanol or benzyl alcohol in the presence of an acid and decomposing the product with water; and (g) by interconversion of acids, esters, salts and amides of the first general formula above using known methods. Methyl [(α - methyl - 4 - chlorobenzylideneamino) - oxy] - acetimidate hydrochloride is prepared by reaction of the sodium salt of 4<SP>1</SP>- chloroacetophenone oxime with chloroacetonitrile and reaction of the resulting [(α-methyl-4- chlorobenzylideneamino)oxy]acetonitrile with hydrogen chloride and methanol. Pharmaceutical compositions having antiinflammatory and analgetic activity comprise, as active ingredient, a benzylideneaminohydroxyalkanoic acid derivative of the first general formula above, together with a solid or liquid carrier, and may be administered orally, rectally or parenterally.