Chemische Verfahren und Produkte

摘要

1,234,626. 5-Phenyl-salicylic acid derivatives. MERCK & CO. Inc. 1 Oct., 1968 [6 Oct., 1967], No. 46605/68. Heading C2C. Novel compounds of Formula 1 in which X is a halogen or hydrogen atom; R 1 is a hydrogen atom or a C 1-5 alkyl radical; R 2 is a hydrogen atom or a C 1-6 acyl or C 1-5 alkyl radical; R 3 is a hydrogen atom or a halo alkyl, nitro, amino, dialkylamino, C 1-6 acyl, heterocyclic-substituted C 1-5 alkyl, dialkylaminoalkyl, amino alkyl, cyano, sulphonyl, sulphamoyl, hydroxy, acyloxy, mercapto or alkylthio radical; and R is a hydrogen atom or an alkyl, alkoxy, nitro, haloalkyl, amino, dialkylamino, acylamino, C 1-6 acyl, hydroxy, acyloxy, sulphonyl or sulphamoyl radical, with the provisos that when R 3 is OH one of X, R, R 1 and R 2 is other than H and that when X and R 3 are both hydrogen, R must be halogen, alkyl or alkoxy, are prepared by one of the following methods: (i) a compound of Formula II is reacted with CO 2 at elevated temperature and pressure; (ii) a compound of Formula I above wherein R 3 is H is nitrated and optionally reduced to give compounds where R 3 is nitro or amino; (iii) a compound of Formula I above wherein R 3 is H and R 2 is acyl is heated with AlCl 3 to give a compound where R 2 is H and R 3 is acyl; (iv) esterification of compounds in which R 1 and/or R 2 are H; or (v) where R 3 is heterocyclic substituted alkyl, by reaction of the compound R 3 =haloalkyl with the heterocyclic compound. 5-(41-Fluorophenyl)salicylic acid is prepared by action of CO 2 on 4-(41fluorophenyl)-phenol prepared by action of hot nitrous acid on 4-(41- fluorophenyl)-aniline. Pharmaceutical compositions in conventional forms for oral administration having antiinflammatory, anti-pyretic and analgesic activity comprise an above novel compound and an inert diluent carrier or coating.