Discovery of 3,9-diazabicyclo[4.2.1]nonanes as potent dual orexin receptor antagonists with sleep-promoting activity in the rat

Bioorg Med Chem Lett. 2010 Jul 15;20(14):4201-5. doi: 10.1016/j.bmcl.2010.05.047. Epub 2010 May 25.

Abstract

Orexins are excitatory neuropeptides that regulate arousal and sleep. Orexin receptor antagonists promote sleep and offer potential as a new therapy for the treatment of insomnia. In this Letter, we describe the synthesis of constrained diazepanes having a 3,9 diazabicyclo[4.2.1]nonane bicyclic core with good oral bioavailability and sleep-promoting activity in a rat EEG model.

MeSH terms

  • Alkanes / chemistry
  • Alkanes / pharmacokinetics
  • Alkanes / pharmacology*
  • Animals
  • Aza Compounds / chemistry
  • Aza Compounds / pharmacokinetics
  • Aza Compounds / pharmacology
  • Biological Availability
  • Bridged Bicyclo Compounds / chemistry
  • Bridged Bicyclo Compounds / pharmacokinetics
  • Bridged Bicyclo Compounds / pharmacology
  • Drug Discovery*
  • Electroencephalography
  • Hypnotics and Sedatives / chemistry
  • Hypnotics and Sedatives / pharmacokinetics
  • Hypnotics and Sedatives / pharmacology*
  • Orexin Receptors
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, G-Protein-Coupled / antagonists & inhibitors*
  • Receptors, Neuropeptide / antagonists & inhibitors*

Substances

  • Alkanes
  • Aza Compounds
  • Bridged Bicyclo Compounds
  • Hypnotics and Sedatives
  • Orexin Receptors
  • Receptors, G-Protein-Coupled
  • Receptors, Neuropeptide
  • nonane