N-Glycine-sulfonamides as potent dual orexin 1/orexin 2 receptor antagonists

Bioorg Med Chem Lett. 2008 Nov 1;18(21):5729-33. doi: 10.1016/j.bmcl.2008.09.079. Epub 2008 Sep 26.

Abstract

A series of dual OX(1)R/OX(2)R orexin antagonists was prepared based on a N-glycine-sulfonamide core. SAR studies of a screening hit led to compounds with low nanomolar affinity for both receptors and good oral bioavailability. One of these compounds, 47, has demonstrated in vivo activity in rats following oral administration.

MeSH terms

  • Animals
  • Biological Availability
  • Blood-Brain Barrier
  • Glycine / chemistry
  • Glycine / pharmacokinetics
  • Glycine / pharmacology*
  • Male
  • Orexin Receptors
  • Rats
  • Rats, Wistar
  • Receptors, G-Protein-Coupled / antagonists & inhibitors*
  • Receptors, Neuropeptide / antagonists & inhibitors*
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacokinetics
  • Sulfonamides / pharmacology*

Substances

  • Orexin Receptors
  • Receptors, G-Protein-Coupled
  • Receptors, Neuropeptide
  • Sulfonamides
  • Glycine