Discovery of (3S,3aR)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid (PF-3882845), an orally efficacious mineralocorticoid receptor (MR) antagonist for hypertension and nephropathy

J Med Chem. 2010 Aug 26;53(16):5979-6002. doi: 10.1021/jm100505n.

Abstract

We have discovered a novel class of nonsteroidal pyrazoline antagonists of the mineralocorticoid receptor (MR) that show excellent potency and selectivity against other nuclear receptors. Early analogues were poorly soluble and had a propensity to inhibit the hERG channel. Remarkably, both of these challenges were overcome by incorporation of a single carboxylate moiety. Structural modification of carboxylate-containing lead R-4g with a wide range of substituents at each position of the pyrazoline ring resulted in R-12o, which shows excellent activity against MR and reasonable pharmacokinetic profile. Introduction of conformational restriction led to a novel series characterized by exquisite potency and favorable steroid receptor selectivity and pharmacokinetic profile. Oral dosing of 3S,3aR-27d (PF-3882845) in the Dahl salt sensitive preclinical model of salt-induced hypertension and nephropathy showed blood pressure attenuation significantly greater than that with eplerenone, reduction in urinary albumin, and renal protection. As a result of these findings, 3S,3aR-27d was advanced to clinical studies.

MeSH terms

  • Animals
  • Antihypertensive Agents / chemical synthesis*
  • Antihypertensive Agents / pharmacokinetics
  • Antihypertensive Agents / pharmacology
  • Blood Pressure / drug effects
  • Cell Line, Tumor
  • Chlorobenzenes
  • Crystallography, X-Ray
  • Humans
  • Hypertension / drug therapy*
  • Indazoles / chemical synthesis*
  • Indazoles / pharmacokinetics
  • Indazoles / pharmacology
  • Indenes
  • Kidney Diseases / drug therapy*
  • Male
  • Mineralocorticoid Receptor Antagonists*
  • Models, Molecular
  • Molecular Conformation
  • Nitriles / chemical synthesis*
  • Nitriles / pharmacokinetics
  • Nitriles / pharmacology
  • Radioligand Assay
  • Rats
  • Rats, Inbred Dahl
  • Rats, Sprague-Dawley
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antihypertensive Agents
  • Chlorobenzenes
  • Indazoles
  • Indenes
  • Mineralocorticoid Receptor Antagonists
  • Nitriles
  • (3S,3aR)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo(g)indazole-7-carboxylic acid