Discovery and biological characterization of (2R,4S)-1'-acetyl-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4,4'-bipiperidine-1-carboxamide as a new potent and selective neurokinin 1 (NK1) receptor antagonist clinical candidate

J Med Chem. 2011 Feb 24;54(4):1071-9. doi: 10.1021/jm1013264. Epub 2011 Jan 13.

Abstract

A large body of compelling preclinical evidence supports the clinical use of neurokinin (NK) receptor antagonists in a plethora of CNS and non-CNS therapeutic areas. The significant investment made in this area over the past 2 decades culminated with the observation that NK(1) receptor antagonists elicited clinical efficacy in major depression disorders. In addition, aprepitant (Merck) was launched as a new drug able to prevent chemotherapy-induced nausea and vomiting (CINV). After the discovery by GlaxoSmithKline of vestipitant, a wide drug discovery program was launched aimed at identifying additional clinical candidates. New compounds were designed to maximize affinity at the NK(1) receptor binding site while retaining suitable physicochemical characteristics to ensure excellent pharmacokinetic and pharmacodynamic properties in vivo. Herein we describe the discovery process of a new NK(1) receptor antagonist (casopitant) selected as clinical candidate and progressed into clinical studies to treat major depression disorders.

MeSH terms

  • Animals
  • Behavior, Animal / drug effects
  • Brain / drug effects*
  • Brain / metabolism*
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • Depressive Disorder / drug therapy*
  • Depressive Disorder / metabolism
  • Drug Discovery
  • Gerbillinae
  • Half-Life
  • Humans
  • Magnetic Resonance Spectroscopy
  • Neurokinin-1 Receptor Antagonists*
  • Piperazines / chemical synthesis*
  • Piperazines / chemistry
  • Piperazines / pharmacokinetics
  • Piperazines / pharmacology*
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Piperidines / pharmacokinetics
  • Piperidines / pharmacology*
  • Regression Analysis
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Stereoisomerism

Substances

  • Neurokinin-1 Receptor Antagonists
  • Piperazines
  • Piperidines
  • casopitant