Discovery and characterization of AZD9272 and AZD6538-Two novel mGluR5 negative allosteric modulators selected for clinical development

Bioorg Med Chem Lett. 2012 Nov 15;22(22):6974-9. doi: 10.1016/j.bmcl.2012.08.100. Epub 2012 Sep 21.

Abstract

AZD9272 and AZD6538 are two novel mGluR5 negative allosteric modulators selected for further clinical development. An initial high-throughput screening revealed leads with promising profiles, which were further optimized by minor, yet indispensable, structural modifications to bring forth these drug candidates. Advantageously, both compounds may be synthesized in as little as one step. Both are highly potent and selective for the human as well as the rat mGluR5 where they interact at the same binding site than MPEP. They are orally available, allow for long interval administration due to a high metabolic stability and long half-lives in rats and permeate the blood brain barrier to a high extent. AZD9272 has progressed into phase I clinical studies.

MeSH terms

  • Allosteric Regulation
  • Animals
  • Binding Sites
  • Central Nervous System / diagnostic imaging
  • Drug Evaluation, Preclinical
  • HEK293 Cells
  • Half-Life
  • Humans
  • Isotope Labeling
  • Male
  • Microsomes / metabolism
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / chemistry*
  • Oxadiazoles / pharmacokinetics
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*
  • Pyridines / pharmacokinetics
  • Radionuclide Imaging
  • Rats
  • Receptor, Metabotropic Glutamate 5
  • Receptors, Metabotropic Glutamate / chemistry*
  • Receptors, Metabotropic Glutamate / metabolism
  • Structure-Activity Relationship

Substances

  • AZD6538
  • AZD9272
  • GRM5 protein, human
  • Grm5 protein, rat
  • Oxadiazoles
  • Pyridines
  • Receptor, Metabotropic Glutamate 5
  • Receptors, Metabotropic Glutamate