ES381114A1 - Anilino salicylic acid derivatives - Google Patents

Abstract

A procedure for the preparation of new substituted anilinocarboxylic acids, of formula: **(See formula)** where R is hydrogen or lower alkyl, hydrogen being only when X is fluorine, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, R1 is hydroxy, Not me, lower alkoxy, lower alkyl amino, dialkyl (lower) amino, dialkyl (lower) aminoalkyl (lower) amino, dialkyl (lower) lower aminoalkoxy, lower hydroxyalkoxy, (lower) alkoxy lower alkoxy, lower phenylalkoxy, phenoxy, substituted phenoxy, (lower) alkanoyl lower aminoalkoxy, hydrazine, N-morpholino, aniline, hydroxyalkyl (lower) amino and a naturally occurring amino acid radical with bonding to the N atom, R2 is hydrogen, acyl, I rent, alkoxycarbonyl, the OR2 radical being in an ortho position with respect to the radical **(See formula)** R3 is hydrogen, halogen, haloalkyl, I rent, cycloalkyl, alkoxy and X is hydrogen, I rent, hydroxy, alkoxy, acyloxy, halogen, haloalkyl, nitro, Not me, alkylamino, dialkyl (lower) amino, acylamino, mercapto, alkyl mercapto, alkylsulfinyl, alkylsulfonyl, sulfonamido, sulfonylamide, alkylaminoalkyl, hydroxyalkyl, alkoxyalkyl, mercaptoalkyl, alkyl mercaptoalkyl, cyano, carboxy, carboalkoxy, carbamoyl, aryl, aralkyl, aryloxy or aralkoxy, the aniline portion of the substituted anilinocarboxylic acid being attached to the 4 or 5 position of the salicylic acid portion and the non-toxic and pharmaceutically acceptable salts thereof, the process of which consists of: 1) Carboxylate an appropriate salt of a compound of formula: **(See formula)** with gaseous carbon dioxide, at a temperature between 50 and 300ºC and under a pressure between atmospheric and about 150 Kg/cm2, to give a salicylic acid of the formula: **(See formula)** where X and R are those defined above; 2) React the compound formed in step 1 with an appropriate lower alkanol, in the presence of a strong acid, at room temperature for a long period of time or at elevated temperatures, to prepare the compounds of formula I in which the group is an ester and 3) React the compound formed in step 2 with an amine or a substituted amine to form a compound in which the group (see formula) is an amide. (Machine-translation by Google Translate, not legally binding)