Discovery of a potent, CNS-penetrant orexin receptor antagonist based on an n,n-disubstituted-1,4-diazepane scaffold that promotes sleep in rats

ChemMedChem. 2009 Jul;4(7):1069-74. doi: 10.1002/cmdc.200900069.

Abstract

Silent Night: Antagonism of the orexin (or hypocretin) system has recently been identified as a novel mechanism for the treatment of insomnia. Herein, we describe discovery of a dual (OX(1)R/OX(2)R) orexin receptor antagonist featuring a 1,4-diazepane central constraint that blocks orexin signaling in vivo. In telemetry-implanted rats, oral administration of this antagonist produced a decrease in wakefulness, while increasing REM and non-REM sleep.

MeSH terms

  • Animals
  • Azepines / chemistry*
  • Azepines / pharmacokinetics
  • Azepines / therapeutic use
  • Central Nervous System / drug effects
  • Orexin Receptors
  • Rats
  • Receptors, G-Protein-Coupled / antagonists & inhibitors*
  • Receptors, G-Protein-Coupled / metabolism
  • Receptors, Neuropeptide / antagonists & inhibitors*
  • Receptors, Neuropeptide / metabolism
  • Sleep Wake Disorders / drug therapy*
  • Structure-Activity Relationship

Substances

  • Azepines
  • Orexin Receptors
  • Receptors, G-Protein-Coupled
  • Receptors, Neuropeptide