Discovery of 2,5-diarylnicotinamides as selective orexin-2 receptor antagonists (2-SORAs)

Bioorg Med Chem Lett. 2013 Dec 15;23(24):6620-4. doi: 10.1016/j.bmcl.2013.10.045. Epub 2013 Oct 30.

Abstract

The orexin (or hypocretin) system has been identified as a novel target for the treatment of insomnia due to the wealth of biological and genetic data discovered over the past decade. Recently, clinical proof-of-concept was achieved for the treatment of primary insomnia using dual (OX1R/OX2R) orexin receptor antagonists. However, elucidation of the pharmacology associated with selective orexin-2 receptor antagonists (2-SORAs) has been hampered by the lack of orally bioavailable, highly selective small molecule probes. Herein, the discovery and optimization of a novel series of 2,5-diarylnicotinamides as potent and orally bioavailable orexin-2 receptor selective antagonists is described. A compound from this series demonstrated potent sleep promotion when dosed orally to EEG telemetrized rats.

Keywords: Hypocretin; Insomnia; Orexin receptor antagonists; Rat sleep EEG; Selective orexin-2 receptor antagonists.

MeSH terms

  • Animals
  • Dogs
  • Drug Evaluation, Preclinical
  • Half-Life
  • Humans
  • Nicotinic Acids / chemical synthesis
  • Nicotinic Acids / chemistry*
  • Nicotinic Acids / pharmacokinetics
  • Nicotinic Acids / pharmacology*
  • Orexin Receptor Antagonists*
  • Orexin Receptors / metabolism
  • Protein Binding / drug effects
  • Rats
  • Structure-Activity Relationship

Substances

  • Nicotinic Acids
  • Orexin Receptor Antagonists
  • Orexin Receptors
  • nicotinanilide