2-AZETIDINONE DERIVATIVES

摘要

2-AZETIDINONE DERIVATIVE A 2-azetidinone derivative selected from the group consisting of compounds of formulae (I) and (I') as follows, and their pharmaceutically acceptable salts: (I) wherein: R1 is selected from the group consisting of aralkoxy, acetyloxy, carbobenzoxy, methanesulphonyloxy and p-toluerasulphonyloxy, any one of which groups may be mono-substituted with halogen, C1 to C5 alkyl, C1 to C5 alkoxy and nitro group, amino, phthalylimino, carbobenzoxyamino, benzylamino, hydrogen, hydroxy, C1 to C5 alkoxy and azido group; R2 is selected from the group consisting of C1 to C5 alkyl and aralkyl, either of which groups may be mono-substituted with halogen, C1 to C5 alkyl, C1 to C5 alkoxy and nitro group; and hydrogen; R3 is selected from the group consisting of C1 to C5 alkyl, phenyl, naphthyl, aralkyl, C2 to C5 alkenyl, aralkenyl, C2 to C5 alkynyl, aralkynyl and acyl, any of which groups may be mono-substituted with halogen, C1 to C5 alkyl, C1 to C5 alkoxy, C1 to C5 acyloxy, hydroxy, amino, phthylimino, carbobenzoxyamino benzylamino and nitro group; 2- or 3-furyl, 2- or 3-thienyl, 2- or 3-pyrrolyl, 2- or 4-imidazolyl, 3-pyrazoyl, 4-isoxazolyl, 2-, 3-, 4-, 5-, 6- or 7-indolyl or 2- or 3-benzo (b) furanyl, and R4 is selected from the group consisting of C1 to C5 alkyl, C2 to C5 alkenyl, phenyl, naphthyl and aralkyl, any one of which groups may be mono-substituted with halogen, C1 to C5 alkyl, C1 to C5 alkoxy, C1 to C5 acyloxy, hydroxy, amino, phthalyimino, carbobenzoxyamino, benzylamino, and nitro group, wherein: R1, is selected from the group consisting of aralkoxy, acetyloxy, carbobenzoxy, methanesulphonyloxy and p-toluene-sulphonyloxy, any one of which groups may be monosubstituted with halogen, C1 to C5 alkyl, C1 to C5 alkoxy, and nitro amino, phthalylimino, carbobenzoxyamino, benzylamino group; hydrogen, hydroxy, C1 to C5 alkoxy and azido group; R2, is selected from the group consisting of C1 to C5 alkyl, aralkyl and t-butyldimethylsilyl and trimethylsilyl, any one of which groups may be mono-substituted with i halogen, C1 to C5 alkyl, C1 to C5 alkoxy and nitro groups and hydrogen; R3, is selected from the group consisting of C1 to C5 alkyl, phenyl, naphtyl, aralkyl, C2 to C5 alkenyl, aralkynyl, C2 to C5 alkynyl, aralkenyl, and acyl, any one of which groups may be mono-substituted with halogen, C1 to C5 alkyl, C1 to C5 alkoxy, C1 to C5 acyloxy, hydroxy, amino, phthalylimino, carbobenzoxyamino, benzylamlno, and nitro groups 2- or 3- furyl, 2- or 30thienyl, 2- or 3-pyrrolyl, 2- or 4-imidazolyl, 3-pyrazolyl, 4-isoxazolyl, 2-, 3-, 4-, 5-, 6- or 7-indolyl or 2 or 3-benzo (b) furanyl; and R4, is selected from the group consisting of C1 to C5 alkyl, aralykyl and trialkylsily any one of which groups may be mono-substituted with halogen, C1 to C5 alkyl, C1 to C5 alkoxy and nitro group; and hydrogen; provided however when R1, represents N3 or NH2, and R2 is hydrogen and R4, is CH2-, then R3, is other than and . The derivatives exhibit .beta.-lacatamse inhibiting activity and are thus of interest as anti-bacterial agents. For example, they may be used alone or together with known antibiotic substances, such as cephalosporins and penicillins, for treating various infectious diseases.