N 4-Hydroxy or benzyloxy-phenyl 2-oxazolidinone and pyrrolidinone(s) - substd. by hydroxymethyl (derivs.) are intermediates for antidepressants

摘要

3-(4-W-O-phenyl)-5-B- 2-oxazolidinone and 1-(4-W-O-phenyl)-4-B-2 pyrrolidinone dervis. of formula (I') are new (where W is H or benzyl and (a) Z is O; B is -CH2-OR' and R' is opt. branched 1-3C alkyl, cyclohexyl or methoxymethyl or (b) Z is -CH2 and B is hydroxymethyl or when W is benzyl may also be ethoxycarbonyl or carboxy). (I') are intermediates for psychotropics and antidepressants of formula (I) (where (a) X, A, R, is O, O, H; R2 is -CH2-OR5; R5 is opt. branched 1-3C alkyl or cyclohexyl and R is para position is cyanobutoxy, n-butyloxy, 3-methylbutyloxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohex-1-eneyl-methoxy, cyanoethoxy, 3-cyanopropyloxy or R6-substd.-benzyloxy and R6 is H, 3-chloro, 4-chloro, 3-fluoro, 4-fluoro, 3-cyano, 3-trifluoromethyl or 3 nitro; or R5 is ally, propargyl or methoxymethyl and R in para position is metanitrobenzyloxy; or (b) X, A, R1 is O, -CH2, H; R2 is hydroxymethyl and R is para-(metanitrobenzyloxy). Activity tests are described which show cpds. (I) to be more active than Toloxatone. (I) may be administered orally (50-500mg/day) or parenterally (5-50mg/day).