Azetidine derivatives
AssigneeGist-Brocades N.V.
InventorsJan Verwey, Hong Sheng Tan
Life of this patent
Estimating the term…
Loading patent…
AssigneeGist-Brocades N.V.
InventorsJan Verwey, Hong Sheng Tan
Estimating the term…
New azetidine derivatives of the formula: ##EQU1## wherein R.sub.1 represents a penicillin- or cephalosporin-amido group, R.sub.2 represents one of the groups of the following formulae: ##EQU2## wherein R.sub.4, R.sub.5 and R.sub.6 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, R.sub.3 represents an amino group of the formula ##EQU3## wherein R.sub.7 represents a hydrogen atom or a lower alkyl group and R.sub.8 represents a lower alkyl group, or R.sub.3 represents a N,N'-disubstituted hydrazino group wherein the substituents are lower alkyl groups, e.g. the N,N'-diisopropylhydrazino group, or R.sub.3 represents the group -OR.sub.9, wherein R.sub.9 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 R.sub.9 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.
Acetidine derivatives of the formula ##EQU21## wherein R.sub.1 represents a conventional penicillin- or cephalosporin acylamido group, R.sub.2 is ##EQU22## wherein R.sub.4 and R.sub.5 are individually selected from the group consisting of a hydrogen atom, lower alkyl and alkenyl and n represents 2 or 3 R.sub.3 represents an amino group of the formula ##EQU23## wherein R.sub.7 represents a hydrogen atom or a lower alkyl and R.sub.8 represents a lower alkyl, or R.sub.3 represents a N,N'-disubstituted hydrazine group wherein the substituents are lower alkyl, or R.sub.3 represents the group -OR.sub.9, wherein R.sub.9 represents a hydrogen atom, a lower alkyl optionally substituted by 1 to 3 halogen atoms or by 1 or 2 phenyl groups, wherein te phenyl groups may be substituted by a methoxy or a nitro, or R.sub.9 represents a phenacyl or an alkali metal or alkaline earth metal ions and and corresponding azetidine derivatives of formula I wherein the double bond in the propenyl side chain has been shifted from the 2- to the 1-position.
Dependencies are inferred from the claim text.