Discovery of the S1P2 Antagonist GLPG2938 (1-[2-Ethoxy-6-(trifluoromethyl)-4-pyridyl]-3-[[5-methyl-6-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]pyridazin-3-yl]methyl]urea), a Preclinical Candidate for the Treatment of Idiopathic Pulmonary Fibrosis

J Med Chem. 2021 May 13;64(9):6037-6058. doi: 10.1021/acs.jmedchem.1c00138. Epub 2021 May 3.

Abstract

Mounting evidence from the literature suggests that blocking S1P2 receptor (S1PR2) signaling could be effective for the treatment of idiopathic pulmonary fibrosis (IPF). However, only a few antagonists have been so far disclosed. A chemical enablement strategy led to the discovery of a pyridine series with good antagonist activity. A pyridazine series with improved lipophilic efficiency and with no CYP inhibition liability was identified by scaffold hopping. Further optimization led to the discovery of 40 (GLPG2938), a compound with exquisite potency on a phenotypic IL8 release assay, good pharmacokinetics, and good activity in a bleomycin-induced model of pulmonary fibrosis.

MeSH terms

  • Animals
  • CHO Cells
  • Cricetulus
  • Drug Design*
  • Humans
  • Idiopathic Pulmonary Fibrosis / drug therapy*
  • Idiopathic Pulmonary Fibrosis / metabolism
  • Interleukin-8 / metabolism
  • Male
  • Mice
  • Pyridazines / chemistry*
  • Pyridazines / pharmacokinetics
  • Pyridazines / pharmacology*
  • Pyridazines / therapeutic use
  • Sphingosine-1-Phosphate Receptors / antagonists & inhibitors*
  • Structure-Activity Relationship
  • Tissue Distribution

Substances

  • Interleukin-8
  • Pyridazines
  • Sphingosine-1-Phosphate Receptors
  • pyridazine