Discovery of Molidustat (BAY 85-3934): A Small-Molecule Oral HIF-Prolyl Hydroxylase (HIF-PH) Inhibitor for the Treatment of Renal Anemia

ChemMedChem. 2018 May 23;13(10):988-1003. doi: 10.1002/cmdc.201700783. Epub 2018 Apr 14.

Abstract

Small-molecule inhibitors of hypoxia-inducible factor prolyl hydroxylases (HIF-PHs) are currently under clinical development as novel treatment options for chronic kidney disease (CKD) associated anemia. Inhibition of HIF-PH mimics hypoxia and leads to increased erythropoietin (EPO) expression and subsequently increased erythropoiesis. Herein we describe the discovery, synthesis, structure-activity relationship (SAR), and proposed binding mode of novel 2,4-diheteroaryl-1,2-dihydro-3H-pyrazol-3-ones as orally bioavailable HIF-PH inhibitors for the treatment of anemia. High-throughput screening of our corporate compound library identified BAY-908 as a promising hit. The lead optimization program then resulted in the identification of molidustat (BAY 85-3934), a novel small-molecule oral HIF-PH inhibitor. Molidustat is currently being investigated in clinical phase III trials as molidustat sodium for the treatment of anemia in patients with CKD.

Keywords: BAY 85-3934; HIF-PH; inhibitors; metalloenzymes; molidustat.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anemia / drug therapy*
  • Anemia / etiology
  • Animals
  • Binding Sites
  • Cell Line, Tumor
  • Drug Discovery
  • Humans
  • Hypoxia-Inducible Factor-Proline Dioxygenases / antagonists & inhibitors*
  • Kidney Diseases / complications*
  • Mice
  • Molecular Structure
  • Protein Binding
  • Protein Conformation
  • Pyrazoles / pharmacology*
  • Pyrazoles / therapeutic use
  • Structure-Activity Relationship
  • Triazoles / pharmacology*
  • Triazoles / therapeutic use

Substances

  • Pyrazoles
  • Triazoles
  • molidustat
  • Hypoxia-Inducible Factor-Proline Dioxygenases