Discovery of potent, selective, orally active benzoxazepine-based Orexin-2 receptor antagonists

Bioorg Med Chem Lett. 2011 Nov 1;21(21):6414-6. doi: 10.1016/j.bmcl.2011.08.093. Epub 2011 Aug 30.

Abstract

During our efforts to identify a series of potent, selective, orally active human Orexin-2 Receptor (OX2R) antagonists, we elucidated structure-activity relationship (SAR) on the 7-position of a benzoxazepine scaffold by utilizing Hammett σ(p) and Hansch-Fujita π value as aromatic substituent constants. The attempts led to the discovery of compound 1m, possessing good in vitro potency with over 100-fold selectivity against OX1R, good metabolic stability in human and rat liver microsome, good oral bioavailability in rats, and in vivo antagonistic activity in rats by oral administration.

MeSH terms

  • Administration, Oral
  • Animals
  • Azepines / chemistry
  • Azepines / pharmacology*
  • Drug Discovery*
  • Humans
  • Microsomes, Liver / drug effects
  • Microsomes, Liver / metabolism
  • Orexin Receptors
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, G-Protein-Coupled / antagonists & inhibitors*
  • Receptors, Neuropeptide / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Azepines
  • HCRTR2 protein, human
  • Hcrtr1 protein, rat
  • Orexin Receptors
  • Receptors, G-Protein-Coupled
  • Receptors, Neuropeptide