Discovery of the Soluble Guanylate Cyclase Stimulator Vericiguat (BAY 1021189) for the Treatment of Chronic Heart Failure

J Med Chem. 2017 Jun 22;60(12):5146-5161. doi: 10.1021/acs.jmedchem.7b00449. Epub 2017 Jun 12.

Abstract

The first-in-class soluble guanylate cyclase (sGC) stimulator riociguat was recently introduced as a novel treatment option for pulmonary hypertension. Despite its outstanding pharmacological profile, application of riociguat in other cardiovascular indications is limited by its short half-life, necessitating a three times daily dosing regimen. In our efforts to further optimize the compound class, we have uncovered interesting structure-activity relationships and were able to decrease oxidative metabolism significantly. These studies resulting in the discovery of once daily sGC stimulator vericiguat (compound 24, BAY 1021189), currently in phase 3 trials for chronic heart failure, are now reported.

MeSH terms

  • Administration, Intravenous
  • Administration, Oral
  • Animals
  • Blood Pressure / drug effects
  • Chemistry Techniques, Synthetic
  • Dogs
  • Heart Failure / drug therapy*
  • Hepatocytes / drug effects
  • Heterocyclic Compounds, 2-Ring / administration & dosage
  • Heterocyclic Compounds, 2-Ring / chemistry*
  • Heterocyclic Compounds, 2-Ring / pharmacology*
  • Humans
  • Male
  • NG-Nitroarginine Methyl Ester / adverse effects
  • Pyrimidines / administration & dosage
  • Pyrimidines / chemistry*
  • Pyrimidines / pharmacology*
  • Rats, Transgenic
  • Rats, Wistar
  • Soluble Guanylyl Cyclase / genetics
  • Soluble Guanylyl Cyclase / metabolism*
  • Structure-Activity Relationship*

Substances

  • Heterocyclic Compounds, 2-Ring
  • Pyrimidines
  • Soluble Guanylyl Cyclase
  • vericiguat
  • NG-Nitroarginine Methyl Ester