1-[(1-methyl-1H-imidazol-2-yl)methyl]-4-phenylpiperidines as mGluR2 positive allosteric modulators for the treatment of psychosis

J Med Chem. 2011 Mar 24;54(6):1724-39. doi: 10.1021/jm101414h. Epub 2011 Mar 2.

Abstract

A novel series of mGluR2 positive allosteric modulators (PAMs), 1-[(1-methyl-1H-imidazol-2-yl)methyl]-4-phenylpiperidines, is herein disclosed. Structure-activity relationship studies led to potent, selective mGluR2 PAMs with excellent pharmacokinetic profiles. A representative lead compound (+)-17e demonstrated dose-dependent inhibition of methamphetamine-induced hyperactivity and mescaline-induced scratching in mice, providing support for potential efficacy in treating psychosis.

MeSH terms

  • Allosteric Regulation
  • Animals
  • Antipsychotic Agents / chemical synthesis*
  • Antipsychotic Agents / pharmacokinetics
  • Antipsychotic Agents / pharmacology
  • Biological Availability
  • Brain / metabolism
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacokinetics
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology
  • Cell Line
  • Dogs
  • Humans
  • Hyperkinesis / chemically induced
  • Hyperkinesis / drug therapy
  • Imidazoles / chemical synthesis*
  • Imidazoles / pharmacokinetics
  • Imidazoles / pharmacology
  • In Vitro Techniques
  • Methamphetamine
  • Mice
  • Microsomes, Liver / metabolism
  • Models, Molecular
  • Piperidines / chemical synthesis*
  • Piperidines / pharmacokinetics
  • Piperidines / pharmacology
  • Protein Conformation
  • Radioligand Assay
  • Rats
  • Receptors, Metabotropic Glutamate / metabolism*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 1-methyl-2-((3-methyl-4-(4-trifluoromethyl-2-fluoro)phenyl)piperidin-1-ylmethyl)-1H-imidazo(4,5-b)pyridine
  • Antipsychotic Agents
  • Bridged Bicyclo Compounds, Heterocyclic
  • Imidazoles
  • Piperidines
  • Receptors, Metabotropic Glutamate
  • metabotropic glutamate receptor 2
  • Methamphetamine