Heterocyclyl tetracyclines. 2. 7-Methoxy-8-pyrrolidinyltetracyclines: discovery of TP-2758, a potent, orally efficacious antimicrobial against Gram-negative pathogens

J Antibiot (Tokyo). 2018 Feb;71(2):287-297. doi: 10.1038/ja.2017.86. Epub 2017 Jul 26.

Abstract

A convergent total synthesis platform led to the discovery of TP-2758 from a series of novel 7-methoxy-8-heterocyclyl tetracycline analogs. TP-2758 demonstrated high in vitro potency against key Gram-negative pathogens including extended spectrum β-lactamases- and carbapenemase-producing Enterobacteriaceae and Acinetobacter spp. strains. This compound was efficacious when administered either intravenously or orally in multiple murine infection models and displayed a favorable preclinical pharmacological profile supporting its advancement into clinical development.

MeSH terms

  • Acinetobacter / drug effects
  • Administration, Intravenous
  • Administration, Oral
  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacokinetics
  • Anti-Bacterial Agents / pharmacology*
  • Bacterial Proteins / antagonists & inhibitors
  • Bacterial Proteins / genetics
  • Drug Discovery
  • Drug Resistance, Multiple, Bacterial / drug effects
  • Enterobacteriaceae / drug effects
  • Gram-Negative Bacteria / drug effects*
  • Gram-Negative Bacterial Infections / microbiology
  • Macaca fascicularis
  • Microbial Sensitivity Tests
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship
  • Tetracyclines / chemical synthesis*
  • Tetracyclines / pharmacokinetics
  • Tetracyclines / pharmacology*
  • beta-Lactamase Inhibitors / chemical synthesis
  • beta-Lactamase Inhibitors / pharmacology
  • beta-Lactamases / genetics

Substances

  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Tetracyclines
  • beta-Lactamase Inhibitors
  • beta-Lactamases
  • carbapenemase