Therapeutically active benzoic acid derivatives and a process fo

Details Therapeutically active benzoic acid derivatives and a process fo Therapeutically active benzoic acid derivatives and a process fo

1976-06-17

1978-06-06

Helfin, Bernard

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260558P, 260559S, 424309, 424324, C07C 6508, A01N 924

Patent

active

040936481

ABSTRACT:
Therapeutically active 2- and 3-substituted benzoic acid derivatives having the general formula ##STR1## wherein X is OH, NH.sub.2 or an anilino group having the phenyl ring unsubstituted or substituted by chlorine or by a 4-ethoxy group; or ##STR2## wherein X is NH.sub.2 or an anilino group having the phenyl ring unsubstituted or substituted by chlorine or by a 4-ethoxy group; pharmacologically acceptable mineral or organic acid addition salts including quaternary ammonium salts of those compounds having a basic nitrogen atom and alkaline or alkaline earth metal salts of those compounds wherein X is OH.
Compounds of the formula wherein X is amino or anilino are prepared by reacting 3-propionylsalicyclic acid or a functional derivative thereof with ammonia or an amine in an anhydrous solvent. Compounds of the formula wherein X is OH are prepared by etherifying the ethylester of 3-propionylsalicyclic acid with diethylaminoethylchloride in the presence of an acid binding agent in a ketonic solvent and thereafter hydrolyzing the ester group with a mineral acid or an alkaline earth metal hydroxide.

REFERENCES:
patent: 2847344 (1958-08-01), Clinton et al.
patent: 2872476 (1959-02-01), Melkonian et al.
patent: 2914552 (1959-11-01), Hiltmann et al.
Moore et al., J.A.C.S., vol. 78, pp. 5633-5636 (1956).

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