Antibacterial azetidinones with a carboxyalk(en)yl side chain - prepd. e.g. by acylation and cyclisation of imines

Azetidinones of formula (I) are new (R1 is opt. substd. amino, substd. OH, N3 or halo. R3 is H, hydroxymethyl, arylalkoxylminomethyl, aryl, aralkenyl, formyl, carboxy or a nucleophile residue. R3 is CHR4R5 or -CR5=CR6R7. R4 = aryl, aralkyl, arylthioalkyl or heterocyclyl, R5 = COOH or one of its derivs. R6 = alkyl, haloalkyl, heterocyclythioalkyl, or arylthio. R7 = H, haloalkyl or heterocyclylthioalkyl; provided that (A) when R1 = NH2 or acylamino derived from carboxylic or sulphonic acid, and R2 = H, then R3 is CHR4R5, CR5=CR6R7 or CR5=CHR8, with R4 = phenyl substd. by opt. N-substd. alkanesulphonamido or aroylalkoxy, naphthyl, aralkyl, arylthioalkyl or heterocyclyl. R6 = alkyl, haloalkyl or heterocyclyl thioalkyl. R7 = haloalkyl or heterocyclythioalkyl. R8 = arylthio. (B) when R1 is opt. substd. amino or N3, and R2 = aryl, halo or residue of an S-contg. nucleophile, then R6 = alkyl or heterocyclylic thioalkyl; R7 is heterocyclic thioalkyl; R8 is arylthio. Alkane, arene and heterocyclic gps. are opt. substd.). (I) are antibacterials useful for treating Gram positive and negative inections in animal including humans. The usual dose is 1-2g/day. A typical cpd., 0.2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(2-thienyl)acetate, was prepd. from 2-phthalimidoacetyl chloride and 1,3,5-tris D-1-(2-thienyl)-1-methoxycarbonylmethyl perhydro-1,3,5- -triazine.