The discovery of asunaprevir (BMS-650032), an orally efficacious NS3 protease inhibitor for the treatment of hepatitis C virus infection

J Med Chem. 2014 Mar 13;57(5):1730-52. doi: 10.1021/jm500297k. Epub 2014 Mar 5.

Abstract

The discovery of asunaprevir (BMS-650032, 24) is described. This tripeptidic acylsulfonamide inhibitor of the NS3/4A enzyme is currently in phase III clinical trials for the treatment of hepatitis C virus infection. The discovery of 24 was enabled by employing an isolated rabbit heart model to screen for the cardiovascular (CV) liabilities (changes to HR and SNRT) that were responsible for the discontinuation of an earlier lead from this chemical series, BMS-605339 (1), from clinical trials. The structure-activity relationships (SARs) developed with respect to CV effects established that small structural changes to the P2* subsite of the molecule had a significant impact on the CV profile of a given compound. The antiviral activity, preclincial PK profile, and toxicology studies in rat and dog supported clinical development of BMS-650032 (24).

MeSH terms

  • Animals
  • Antiviral Agents / blood
  • Antiviral Agents / chemistry
  • Antiviral Agents / therapeutic use*
  • Dogs
  • Hepatitis C / drug therapy*
  • Humans
  • Isoquinolines / blood
  • Isoquinolines / chemistry
  • Isoquinolines / therapeutic use*
  • Models, Molecular
  • Protease Inhibitors / blood
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / therapeutic use*
  • Rabbits
  • Rats
  • Sulfonamides / blood
  • Sulfonamides / chemistry
  • Sulfonamides / therapeutic use*
  • Viral Nonstructural Proteins / antagonists & inhibitors*

Substances

  • Antiviral Agents
  • Isoquinolines
  • NS3 protein, hepatitis C virus
  • Protease Inhibitors
  • Sulfonamides
  • Viral Nonstructural Proteins
  • asunaprevir

Associated data

  • PDB/4NWK
  • PDB/4NWL