N-heteroaryl-2-phenyl-3-(benzyloxy)piperidines: a novel class of potent orally active human NK1 antagonists

J Med Chem. 1996 Jul 19;39(15):2907-14. doi: 10.1021/jm9506534.

Abstract

The preparation of a series of N-heteroarylpiperidine ether-based human NK1 antagonists is described. Two of the compounds 3-[-(2S,3S)-3-(((3,5-bis(trifluoromethyl)phenyl)methyl)oxy)- 2-phenylpiperidino}methyl]-1,2,4-triazole (11) and 5-[¿(2S,3S)-3-(((3,5-bis(trifluoromethyl)-phenyl)methyl)oxy)-2- phenylpiperidino}methyl]-3-oxo-1,2,4-triazolone (12)), in particular, are orally bioavailable and exhibited significant improvements in potency, both in vitro and in vivo, over the lead (carboxamidomethyl)piperidine ether 1. Rat liver microsome studies on a selected number of compounds from this series show the triazolone heterocycle to be considerably more stable than the others. Furthermore, both 11 and 12 have been profiled in a number of assays that may be predictive of the clinical utility of substance P antagonists.

MeSH terms

  • Animals
  • Biological Availability
  • Drug Stability
  • Ferrets
  • Guinea Pigs
  • Humans
  • Inflammation / drug therapy
  • Macaca mulatta
  • Male
  • Microsomes, Liver / metabolism
  • Migraine Disorders / drug therapy
  • Neurokinin-1 Receptor Antagonists*
  • Piperidines / chemical synthesis*
  • Piperidines / metabolism
  • Piperidines / therapeutic use
  • Rats
  • Receptors, Neurokinin-1 / metabolism
  • Triazoles / chemical synthesis*
  • Triazoles / metabolism
  • Triazoles / therapeutic use
  • Vomiting / drug therapy

Substances

  • 3-((3-(((3,5-bis(trifluoromethyl)phenyl)methyl)oxy)-2-phenylpiperidino)methyl)-1,2,4-triazole
  • 5-((3-(((3,5-bis(trifluoromethyl)phenyl)methyl)oxy)-2-phenylpiperidino)methyl)-3-oxo-1,2,4-triazolone
  • Neurokinin-1 Receptor Antagonists
  • Piperidines
  • Receptors, Neurokinin-1
  • Triazoles