NOVEL N-ARYL OXAZOLIDINONES,OXAZOLIDINETHIONES,PYRROLIDINONES,PYRROLIDININES AND THIAZOLIDINONES,PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION IN THERAPEUTICS

摘要

Azolidone derivs. of formulae (Ia)-(Ie) and intermediates for their prepn. are claimed. In (Ia) (i) R2 is CH2OCOR3, where R3 is 1-8C alkyl, cyclohexyl, Ph, CH2OMe or CH2OPh, and R is a p-substituent comprising n-BuO, 3-methylbutoxy, cyclopentylmethoxy, cyclohexylmethoxy, 2-cyanoethoxy, OCH2CN or OCH2Ar, where Ar is Ph, m-chlorophenyl, m- or p-fluorophenyl, m-cyanophenyl, m-nitrophenyl, 3-nitro-5-chlorophenyl or 3-nitro-5cyanophenyl; or (ii) R2 is CH2OR6, where R6 is 1-5C alkyl, cycloexhyl, allyl, propargyl or CH2OMe, and R is m-Me or a p-substituent comprising 4-6C alkoxy, (4-7C cycloalkyl)methoxy, 1-methyl-1-cyclopentylmethoxy, 1-cyclopentenylmethoxy, 1-cyclohexenylmethoxy, 2-butenyloxy, 3-methyl-2-butenyloxy, 4-chlorobytoxy, 2-cyanoethoxy, 3-cyanopropoxy, 4-cyanobutoxy, 2-oxopropoxy, 4-oxo 1-cyclohexylmethoxy, 2-morpholinoethoxy, NEt2, 4- or 3-tetrahydropyranyloxy, trans-styryl (opt. m-substd. by Cl, CN or NO2), cis-styryl (opt. m-substd. by NO2), PhC=C, phenethyl, phenyl or OCH2AR', where Ar' is Ph, 3- or 4-Cl-phenyl, 3- or 4-F-phenyl, 3-I-phenyl, 3-Br-phenyl, 3-CF3-phenyl, 3- or 4-NO2-phenyl, 3- or 4-CN-phenyl, 3-Cl-4-F-phenyl, 3-CN,4-F-phenyl, 3-NO2-4-F-phenyl, 3,4-di-Cl-phenyl, 3-Cl-4-NO2-phenyl, 3-Cl-5-NO2-phenyl, 3-CN-5-NO2-phenyl or 3 5-di-Cl-phenyl; or (iii) CH2NR12R13. where NR12R13 is NH2, NHMe, NHEt, NHCHMe2, NME2, pyrrolidino or morpholino, and R is a p-substituent comprising n-BuO, 3-methylbutoxy, cyclopentylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, OCH2CN, OCH2CH2CN or OCH2Ar", where Ar" is Ph, 3-Cl-phenyl, 4-F-phenyl, 3-CN-phenyl, 3-NO2-phenyl or 3-Cl-5-NO2-phenyl). In (Ib)-(Ie) (i) R'2 is CH2OH and R' is 2-5C alkoxy, cyclopentylmethoxy, cyclohexylmethoxy, 1-cyclohexenylmethoxy, 4-tetrahydropyranylmethoxy, O(CH2)nCN(n=1-4) or OCH2Ar1, where Ar1 is 3- or 4-Cl-phenyl, 3- or 4-F-phenyl, 3-NO2-phenyl, 3-CN-phenyl, 3-CF3-phenyl, 3-Cl-5-NO2-phenyl or 3-CN-4-F-phenyl; or (ii) R'2 is CH2OR16, where R16 is 1-3C alkyl, and R' is 3-methyl-n-butoxy, cyclopentylmethoxy, cyclohexylmethoxy, 4-cyanobutoxy or OCH2Ar2, where Ar2 is 3-CN-phenyl, 3-NO2-phenyl, 3-CN-5-NO2-phenyl or 3-pyridyl; or (iii) R'2 is CH2OCOR 18, where R18 is Me or Et, and R' is cyclohexylmethoxy m-CN-benzyloxy or m-NO2-benzyloxy). Cpds. (Ia)-(Ie) are psychotropic agents and potential antidepressants, e.g. with higher activity than toloxation against reserpine-induced ptosis.