Respiratory syncytial virus fusion inhibitors. Part 4: optimization for oral bioavailability

Bioorg Med Chem Lett. 2007 Feb 15;17(4):895-901. doi: 10.1016/j.bmcl.2006.11.063. Epub 2006 Dec 1.

Abstract

A series of benzimidazole-based inhibitors of respiratory syncytial virus (RSV) fusion were optimized for antiviral potency, membrane permeability and metabolic stability in human liver microsomes. 1-Cyclopropyl-1,3-dihydro-3-[[1-(4-hydroxybutyl)-1H-benzimidazol-2-yl]methyl]-2H-imidazo[4,5-c]pyridin-2-one (6m, BMS-433771) was identified as a potent RSV inhibitor demonstrating good bioavailability in the mouse, rat, dog and cynomolgus monkey that demonstrated antiviral activity in the BALB/c and cotton rat models of infection following oral administration.

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacokinetics
  • Antiviral Agents / pharmacology*
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / pharmacokinetics
  • Benzimidazoles / pharmacology*
  • Biological Availability
  • Caco-2 Cells
  • Chemical Phenomena
  • Chemistry, Physical
  • Cytopathogenic Effect, Viral / drug effects
  • Dogs
  • Half-Life
  • Humans
  • In Vitro Techniques
  • Macaca fascicularis
  • Mice
  • Mice, Inbred BALB C
  • Microsomes, Liver / drug effects
  • Rats
  • Respiratory Syncytial Virus Infections / drug therapy
  • Respiratory Syncytial Virus Infections / virology
  • Respiratory Syncytial Virus, Human / drug effects*
  • Sigmodontinae
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • BMS 433771
  • Benzimidazoles