method for the preparation of 2 - (4 - acylaminothio - 3 - amino - 2 - oxoazetidine - 1-yl) - 2 - isopropenylazijnzuur derivative, method for preparation of 7 - amino - 3 - methyl - 3 - cefem - 4 - carboxylic acid derivativesand method for preparation of 6 - amino - - - - 2beta acetoxymethyl 2alfa methylpenam 3 carboxylic acid derivatives.

摘要

New azetidine derivatives of the formula: O PARALLEL C S-N ANGLE ANGLE R2 ¦C R1-CH-CH PARALLEL ¦¦O C-N PARALLEL ¦CH2 OCH-C ANGLE ¦OCH3 C ANGLE R3 wherein R1 represents a penicillin- or cephalosporin-amido group, R2 represents one of the groups of the following formulae: R4 C R4R6 R4OR6 ¦ ANGLE ¦¦ ¦ PARALLEL ¦ ¦ -CC ¦¦ ¦ PARALLEL ¦ -C- ¦ PARALLEL -C-N- -C-C-N- ¦ -CC ¦ ¦ ¦ ANGLE ¦ ¦ R5 C R5 R5 n IIA IIB IIC IID wherein R4, R5 and R6 are the same or different and each represents a hydrogen atom or a lower alkyl or alkenyl group, n represents 2 or 3 and - in case formula IIB represents a phenyl group - this group may carry one to four further substituents selected from the group consisting of halogen atoms and lower alkyl, lower alkenyl and phenyl groups, R3 represents an amino group of the formula R7 -N ANGLE R8 wherein R7 represents a hydrogen atom or a lower alkyl group and R8 represents a lower alkyl group, or R3 represents a N,N'-disubstituted hydrazino group wherein the substituents are lower alkyl groups, e.g. the N,N'-diisopropylhydrazino group, or R3 represents the group -OR9, wherein R9 represents a hydrogen atom, a lower alkyl group, which group may be substituted by 1 to 3 halogen atoms or by 1 or 2 phenyl groups, wherein the phenyl groups may be substituted by a methoxy or a nitro group, or R9 represents a phenacyl group or a salt-forming cation, and corresponding azetidine derivatives of formula 1 wherein the double bond in the propenyl side chain has been shifted from the 2- to the 1-position, which are versatile intermediates in the process of preparing cephalosporanic and penicillanic derivatives.