Azetidinone derivatives
Patent Information
- Application Number
- IL67090
- Authority / Receiving Office
- IL · IL
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 1980-02-20
- Filing Date
- 1980-02-20
- Publication Date
- 1983-02-23
- Estimated Expiration
- Not applicable · inactive patent
AI Technical Summary
Current methods for preparing penem-carboxylic acids and esters with antibacterial activity face challenges in stereochemistry and direct condensation of penicillanic acid S-oxide esters with acetylenic compounds, particularly with pyridinium ions, limiting their effectiveness and versatility.
The development of azetidinone derivatives through a process involving condensation of penicillanic acid S-oxide esters with acetylenic compounds, followed by isomerization, reduction, ozonolysis, and mild alkaline hydrolysis, which allows for the conversion of carbon-carbon double bonds to keto groups and removal of alkoxyoxaly groups, enabling the production of compounds with wide antibacterial and β-lactamase inhibiting activity.
This process ensures the production of azetidinone derivatives with consistent stereochemistry similar to naturally occurring penicillins and cephalosporins, enhancing their antibacterial spectrum and β-lactamase inhibiting capabilities, overcoming previous limitations in direct condensation and stereochemical challenges.