GB1278739A - Anilino salicylic acid derivatives - Google Patents

Abstract

1278739 Anilino-salicylic acid derivatives MERCK & CO Inc 18 June 1970 [25 June 1969 20 April 1970] 29541/70 Heading C2C Novel compounds of Formula I in which R is hydrogen and X is fluorine, alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylamino or alkylamino, or R is alkyl and X is hydrogen, alkyl, hydroxy, alkoxy, acyloxy, halogen, haloalkyl, nitro, amino, alkylamino, dialkylamino, acylamino, mercapto, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, aminoalkyl, alkylaminoalkyl, hydroxyalkyl, alkoxyalkyl, mercaptoalkyl alkylmercaptoalkyl, cyano, carboxy, carboalkoxy, carbamoyl, aryl, aralkyl, aryloxy or aralkoxy; R 1 is hydroxy, amino, alkoxy, alkylamino, dialkylamino, dialkylaminoalkylamino, dialkylaminoalkoxy, hydroxyalkoxy, polyhydroxyalkoxy, alkoxyalkoxy, phenylalkoxy, phenoxy, alkoxyphenoxy, dialkylaminophenoxy, halophenoxy, alkanoylaminophenoxy, anilino, alkanoylaminoalkoxy, hydrazino, hydroxylamino, N- morpholino, hydroxyalkylamino or a radical derived from a naturally occurring amino acid and attached at the N atom; R 2 is hydrogen, acyl, alkyl or alkoxy carbonyl; and R 3 is hydrogen, halogen, haloalkyl, alkyl, cycloalkyl or alkoxy, the anilino portion of the substituted anilino carboxylic acid is connected to the 4 or 5 position of the salicylic acid residue the said alkyl and alkoxy radicals and residues contain not more than five carbon atoms and the said alkanoyl radicals and residues contain not more than six carbon atoms; or a non-toxic pharmaceutically acceptable salt thereof, are prepared by carboxylating a compound of Formula IIa for example, with an alkali metal carbonate and carbon dioxide, and optionally introducing R 1 and R 2 where there are other than OH or H and/or converting one X group into another and/or salt formation. Amino-phenols of Formula VI are prepared by demethylation of the corresponding methyl ether obtained by introduction of R into a compound of formula IV prepared by reaction of a substituted aniline and a halophenol methyl ether. Pharmaceutical compositions in conventional forms for oral, parenteral, rectal or topical administration having anti - inflammatory activity comprise an above novel compound and a carrier or diluent therefor.