Disubstituted piperidines as potent orexin (hypocretin) receptor antagonists

Bioorg Med Chem Lett. 2012 Jun 15;22(12):3890-4. doi: 10.1016/j.bmcl.2012.04.122. Epub 2012 May 4.

Abstract

A series of orexin receptor antagonists was synthesized based on a substituted piperidine scaffold. Through traditional medicinal chemistry structure-activity relationships (SAR), installation of various groups at the 3-6-positions of the piperidine led to modest enhancement in receptor selectivity. Compounds were profiled in vivo for plasma and brain levels in order to identify candidates suitable for efficacy in a model of drug addiction.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Antipsychotic Agents / chemical synthesis*
  • Antipsychotic Agents / pharmacokinetics
  • Brain / drug effects
  • Brain / metabolism
  • Humans
  • Liver / drug effects
  • Liver / metabolism
  • Mice
  • Microsomes, Liver / drug effects
  • Microsomes, Liver / metabolism
  • Molecular Structure
  • Orexin Receptors
  • Piperidines / chemical synthesis*
  • Piperidines / pharmacokinetics
  • Rats
  • Receptors, G-Protein-Coupled / antagonists & inhibitors*
  • Receptors, G-Protein-Coupled / metabolism
  • Receptors, Neuropeptide / antagonists & inhibitors*
  • Receptors, Neuropeptide / metabolism
  • Structure-Activity Relationship
  • Substance-Related Disorders / drug therapy

Substances

  • Antipsychotic Agents
  • Orexin Receptors
  • Piperidines
  • Receptors, G-Protein-Coupled
  • Receptors, Neuropeptide