Discovery of methylsulfonyl indazoles as potent and orally active respiratory syncytial Virus(RSV) fusion inhibitors

Eur J Med Chem. 2017 Sep 29:138:1147-1157. doi: 10.1016/j.ejmech.2017.07.032. Epub 2017 Jul 20.

Abstract

Recently we described a novel class of imidazopyridine compounds that showed exceptional anti-RSV potency in cell culture. However, unfavorable pharmacokinetic (PK) properties and glutathione (GSH) adduct liabilities impeded their further development. In a bid to address the PK and early safety concerns, a small compound library consisting of dozens of scaffold-hopping analogues was designed and synthesized for RSV CPE assay screening, which led to the identification of a new chemical starting point: methylsulfonyl indole compound 8. In this paper, we report the discovery and optimization of a series of methylsulfonyl indazoles as potent RSV fusion inhibitors. In particular, compound 47 was orally efficacious in a RSV mouse model, with 1.6 log unit viral load reduction at 25 mg/kg BID upon oral dosing. The results may have broad implications for the design of new RSV fusion inhibitors, and demonstrate the potential for developing novel therapies for RSV infection.

Keywords: Antiviral; Fusion inhibitors; Heterocycle; Indazole; Respiratory syncytial virus (RSV).

MeSH terms

  • Administration, Oral
  • Animals
  • Antiviral Agents / administration & dosage
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Dose-Response Relationship, Drug
  • Drug Discovery*
  • Humans
  • Indazoles / administration & dosage
  • Indazoles / chemistry
  • Indazoles / pharmacology*
  • Mice
  • Mice, Inbred BALB C
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Rats
  • Respiratory Syncytial Virus Infections / drug therapy*
  • Respiratory Syncytial Virus, Human / drug effects*
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Indazoles