摘要 |
1,166,818. N-Hydroxyamides of phenylacetic acids. MADAN A.G. 25 Nov., 1966 [9 Dec., 1965; 7 Nov., 1966], No. 52909/66. Heading C2C. The invention comprises compounds of formula wherein R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or arylcycloalkyl, R 4 and R 5 are each hydrogen, halo, alkyl, cycloalkyl, dialkylaminoalkyl, or pyridyl, one of R 4 and R 5 alternatively being hydroxyl when the other is hydrogen, and R 2 and R 3 are either two halogens, or one halogen and one hydrogen, or one halogen and one alkyl, or, when at least one of R 4 and R 5 is not hydrogen, two hydrogens; and the alkali metal, alkaline earth metal and ammonium salts thereof. The compounds of Formula I are prepared by reacting a compound of formula (wherein R 6 is alkyl) with hydroxylamine. The alkali metal and ammonium salts are prepared by direct salification of the compounds of Formula I, or the alkali metal salts are obtained by performing the reaction of a compound of Formula II with hydroxylamine in the presence of an alkali metal base. The alkaline earth metal salts are obtained from the alkali metal or ammonium salts by reaction with an alkaline earth metal salt. Ethyl 3,5 - dibromo - 4 - butoxyphenylacetate is prepared from 3,5-dibromo-4-hydroxyacetophenone via 3,5 - dibromo - 4 - hutoxyacetophenone, 3,5 - dibromo - 4 - butoxyphenyl thioacetomorpholide and 3,5 - dibromo - 4 - butozyphenylacetic acid. Ethyl 3-(chloro or fluoro)-4- butoxyphenylacetate is prepared from o-(chloro or fluoro)-phenol via o-(chloro or fluoro)-butoxybenzene, 3 - (chloro or fluoro) - 4 - butoxyacetophenone and 3 - (chloro or fluoro) - 4- butoxyphenylacetic acid. Ethyl 3 - chloro - 4- allyloxyphenylacetate is prepared from ochlorophenol via o - allyloxy - chlorobenzene, 2- chloro - 4 - chloromethyl - allyloxybenzene and 4- allyloxy - 3 - chlorobenzyl cyanide. Ethylα- (p - butoxyphenyl) - propionate is prepared from p - butoxy - benzyl cyanide viaα- (pbutoxyphenyl) - propionitrile. Ethylα- (pbutoxyphenyl) - butyrate is prepared from pbutoxy - benzyl cyanide viaα- (p - butoxyphenyl) - butyronitrile. Methyl p - butoxymandelate is prepared from p-hydroxybenzaldehyde via p-butoxybenzaldehyde, the cyanohydrin thereof, and the iminoester hydrochloride obtained from the cyanohydrin by reaction with methanol and hydrogen chloride. Compounds of Formula I and their alkali metal, alkaline earth metal and ammonium salts are stated to possess anti-inflammatory, analgesic, antipyretic and antispasmodic activities and may be made up with suitable carriers into pharmaceutical compositions.
|