Discovery, Synthesis, and Preclinical Characterization of N-(3-Chloro-4-fluorophenyl)-1H-pyrazolo[4,3-b]pyridin-3-amine (VU0418506), a Novel Positive Allosteric Modulator of the Metabotropic Glutamate Receptor 4 (mGlu4)

ACS Chem Neurosci. 2016 Sep 21;7(9):1192-200. doi: 10.1021/acschemneuro.6b00035. Epub 2016 May 3.

Abstract

The efficacy of positive allosteric modulators (PAMs) of the metabotropic glutamate receptor 4 (mGlu4) in preclinical rodent models of Parkinson's disease has been established by a number of groups. Here, we report an advanced preclinically characterized mGlu4 PAM, N-(3-chloro-4-fluorophenyl)-1H-pyrazolo[4,3-b]pyridin-3-amine (VU0418506). We detail the discovery of VU0418506 starting from a common picolinamide core scaffold and evaluation of a number of amide bioisosteres leading to the novel pyrazolo[4,3-b]pyridine head group. VU0418506 has been characterized as a potent and selective mGlu4 PAM with suitable in vivo pharmacokinetic properties in three preclinical safety species.

Keywords: CYP induction; Metabotropic glutamate receptor 4; Parkinson’s disease; mGlu4; pyrazolo[4,3-b]pyridine.

MeSH terms

  • Allosteric Regulation / drug effects
  • Amides / chemistry
  • Amides / pharmacology
  • Animals
  • Chromatography, High Pressure Liquid
  • Excitatory Amino Acid Agents / chemical synthesis*
  • Excitatory Amino Acid Agents / chemistry
  • Excitatory Amino Acid Agents / pharmacology*
  • Humans
  • Picolinic Acids / chemistry
  • Picolinic Acids / pharmacology*
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Receptors, Metabotropic Glutamate / metabolism*
  • Structure-Activity Relationship

Substances

  • Amides
  • Excitatory Amino Acid Agents
  • Picolinic Acids
  • Pyrazoles
  • Pyridines
  • Receptors, Metabotropic Glutamate
  • Vu0418506
  • picolinamide
  • pyridine
  • metabotropic glutamate receptor 4