Practical and cost-effective manufacturing route for the synthesis of a β-lactamase inhibitor

Org Lett. 2014 Jan 3;16(1):174-7. doi: 10.1021/ol4031606. Epub 2013 Dec 13.

Abstract

Compound 1, a potent and irreversible inhibitor of β-lactamases, is in clinical trials with β-lactam antibiotics for the treatment of serious and antibiotic-resistant bacterial infections. A short, scalable, and cost-effective route for the production of this densely functionalized polycyclic molecule is described.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Azabicyclo Compounds / chemical synthesis
  • Azabicyclo Compounds / chemistry
  • Azabicyclo Compounds / pharmacology*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Molecular Structure
  • Polycyclic Compounds / chemical synthesis
  • Polycyclic Compounds / chemistry
  • Polycyclic Compounds / pharmacology*
  • Structure-Activity Relationship
  • beta-Lactamase Inhibitors*
  • beta-Lactamases / metabolism

Substances

  • Anti-Bacterial Agents
  • Azabicyclo Compounds
  • Enzyme Inhibitors
  • Polycyclic Compounds
  • beta-Lactamase Inhibitors
  • beta-Lactamases
  • relebactam