Oxazolidinone derivatives

摘要

The invention comprises compounds of the formula (wherein R1, R2, R3 and R4 are hydrogen, C1-4 alkyl, aralkyl, cycloalkyl which may be C1-4 alkyl substituted phenyl, alkylenedioxyphenyl or thienyl, or two of them may be a C2-6 alkylene chain; X is -O- or -NH-; A is C2-5 alkylene; and Z is a secondary or tertiary amino group in which two alkyl substituents may be joined either directly or through a further hetero atom or group) and acid-addition salts thereof; and their preparation by reacting the compound HO-AZ or H2N-AZ with an acid chloride of the formula Examples are given. Acid chlorides of the above general formula are prepared from phosgene and the sodium salts of the corresponding N-unsubstituted-oxazolidinones, themselves prepared by cyclizing reaction of substituted hydroxyamines with ethyl carbonate or phosgene or by Curtius degradation of substituted b-hydroxy-propionic acid hydrazides (prepared from esters of the acids and hydrazine). Alpha-(31, 41-methylenedioxyphenyl)-b-amino-ethanol is prepared by reduction of the appropriate nitrile. The hydrochloride is described. The oxazolidinone derivatives of the invention, which are stated to possess analgesic, antipyretic and anti-inflammatory activity, and some of which also have anti-tussive and anti-convulsive activity, may be made up into pharmaceutical compositions with suitable carriers. Tablets, suppositories and injection solutions are referred to.