Invention of MK-7845, a SARS-CoV-2 3CL Protease Inhibitor Employing a Novel Difluorinated Glutamine Mimic

J Med Chem. 2024 Mar 14;67(5):3935-3958. doi: 10.1021/acs.jmedchem.3c02248. Epub 2024 Feb 16.

Abstract

As SARS-CoV-2 continues to circulate, antiviral treatments are needed to complement vaccines. The virus's main protease, 3CLPro, is an attractive drug target in part because it recognizes a unique cleavage site, which features a glutamine residue at the P1 position and is not utilized by human proteases. Herein, we report the invention of MK-7845, a novel reversible covalent 3CLPro inhibitor. While most covalent inhibitors of SARS-CoV-2 3CLPro reported to date contain an amide as a Gln mimic at P1, MK-7845 bears a difluorobutyl substituent at this position. SAR analysis and X-ray crystallographic studies indicate that this group interacts with His163, the same residue that forms a hydrogen bond with the amide substituents typically found at P1. In addition to promising in vivo efficacy and an acceptable projected human dose with unboosted pharmacokinetics, MK-7845 exhibits favorable properties for both solubility and absorption that may be attributable to the unusual difluorobutyl substituent.

MeSH terms

  • Amides
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • COVID-19*
  • Cysteine Endopeptidases / chemistry
  • Glutamine* / chemistry
  • Humans
  • Inventions
  • Protease Inhibitors / pharmacology
  • SARS-CoV-2

Substances

  • Glutamine
  • Cysteine Endopeptidases
  • Protease Inhibitors
  • Amides
  • Antiviral Agents