Triazolopyridines as selective JAK1 inhibitors: from hit identification to GLPG0634

J Med Chem. 2014 Nov 26;57(22):9323-42. doi: 10.1021/jm501262q. Epub 2014 Nov 17.

Abstract

Janus kinases (JAK1, JAK2, JAK3, and TYK2) are involved in the signaling of multiple cytokines important in cellular function. Blockade of the JAK-STAT pathway with a small molecule has been shown to provide therapeutic immunomodulation. Having identified JAK1 as a possible new target for arthritis at Galapagos, the compound library was screened against JAK1, resulting in the identification of a triazolopyridine-based series of inhibitors represented by 3. Optimization within this chemical series led to identification of GLPG0634 (65, filgotinib), a selective JAK1 inhibitor currently in phase 2B development for RA and phase 2A development for Crohn's disease (CD).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Triphosphate / chemistry
  • Animals
  • Arthritis / drug therapy
  • Chemistry, Pharmaceutical / methods*
  • Collagen / chemistry
  • Crohn Disease / drug therapy
  • Crystallography, X-Ray
  • Cytokines / metabolism
  • Dimerization
  • Disease Models, Animal
  • Drug Design
  • Drug Evaluation, Preclinical
  • Humans
  • Inhibitory Concentration 50
  • Janus Kinase 1 / antagonists & inhibitors*
  • Kinetics
  • Phosphorylation
  • Protein Kinase Inhibitors / chemistry*
  • Pyridines / chemistry*
  • Rats
  • Recombinant Proteins / chemistry
  • Structure-Activity Relationship
  • Triazoles / chemistry*

Substances

  • Cytokines
  • GLPG0634
  • Protein Kinase Inhibitors
  • Pyridines
  • Recombinant Proteins
  • Triazoles
  • Adenosine Triphosphate
  • Collagen
  • Janus Kinase 1