Discovery of 2-[[2-Ethyl-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]-8-methylimidazo[1,2-a]pyridin-3-yl]methylamino]-4-(4-fluorophenyl)thiazole-5-carbonitrile (GLPG1690), a First-in-Class Autotaxin Inhibitor Undergoing Clinical Evaluation for the Treatment of Idiopathic Pulmonary Fibrosis

J Med Chem. 2017 May 11;60(9):3580-3590. doi: 10.1021/acs.jmedchem.7b00032. Epub 2017 May 1.

Abstract

Autotaxin is a circulating enzyme with a major role in the production of lysophosphatic acid (LPA) species in blood. A role for the autotaxin/LPA axis has been suggested in many disease areas including pulmonary fibrosis. Structural modifications of the known autotaxin inhibitor lead compound 1, to attenuate hERG inhibition, remove CYP3A4 time-dependent inhibition, and improve pharmacokinetic properties, led to the identification of clinical candidate GLPG1690 (11). Compound 11 was able to cause a sustained reduction of LPA levels in plasma in vivo and was shown to be efficacious in a bleomycin-induced pulmonary fibrosis model in mice and in reducing extracellular matrix deposition in the lung while also reducing LPA 18:2 content in bronchoalveolar lavage fluid. Compound 11 is currently being evaluated in an exploratory phase 2a study in idiopathic pulmonary fibrosis patients.

MeSH terms

  • Animals
  • Humans
  • Idiopathic Pulmonary Fibrosis / drug therapy*
  • Imidazoles / pharmacology
  • Imidazoles / therapeutic use*
  • Mice
  • Mice, Knockout
  • Phosphoric Diester Hydrolases / drug effects*
  • Phosphoric Diester Hydrolases / genetics
  • Pyrimidines / pharmacology
  • Pyrimidines / therapeutic use*
  • Rats

Substances

  • GLPG1690
  • Imidazoles
  • Pyrimidines
  • Phosphoric Diester Hydrolases
  • alkylglycerophosphoethanolamine phosphodiesterase