Synthesis and structure-activity relationships of 8-(pyrid-3-yl)pyrazolo[1,5-a]-1,3,5-triazines: potent, orally bioavailable corticotropin releasing factor receptor-1 (CRF1) antagonists

J Med Chem. 2009 May 14;52(9):3084-92. doi: 10.1021/jm900025h.

Abstract

This report describes the syntheses and structure-activity relationships of 8-(substituted pyridyl)pyrazolo[1,5-a]-1,3,5-triazine corticotropin releasing factor receptor-1 (CRF(1)) receptor antagonists. These CRF(1) receptor antagonists may be potential anxiolytic or antidepressant drugs. This research resulted in the discovery of compound 13-15, which is a potent, selective CRF(1) antagonist (hCRF(1) IC(50) = 6.1 +/- 0.6 nM) with weak affinity for the CRF-binding protein and biogenic amine receptors. This compound also has a good pharmacokinetic profile in dogs. Analogue 13-15 is orally effective in two rat models of anxiety: the defensive withdrawal (situational anxiety) model and the elevated plus maze test. Analogue 13-15 has been advanced to clinical trials.

MeSH terms

  • Administration, Oral
  • Animals
  • Behavior, Animal / drug effects
  • Biological Availability
  • Clinical Trials as Topic
  • Dogs
  • Inhibitory Concentration 50
  • Rats
  • Receptors, Corticotropin-Releasing Hormone / antagonists & inhibitors*
  • Solubility
  • Structure-Activity Relationship
  • Triazines / administration & dosage
  • Triazines / chemical synthesis*
  • Triazines / pharmacokinetics
  • Triazines / pharmacology*
  • Water / chemistry

Substances

  • Receptors, Corticotropin-Releasing Hormone
  • Triazines
  • Water
  • CRF receptor type 1