Synthesis and SAR development of novel mGluR1 antagonists for the treatment of chronic pain

Bioorg Med Chem Lett. 2012 Dec 1;22(23):7223-6. doi: 10.1016/j.bmcl.2012.09.048. Epub 2012 Oct 2.

Abstract

High throughput screening identified the pyridothienopyrimidinone 1 as a ligand for the metabotropic glutamate receptor 1 (mGluR1=10 nM). Compound 1 has an excellent in vivo profile; however, it displays unfavorable pharmacokinetic issues and metabolic stability. Therefore, using 1 as a template, novel analogues (10i) were prepared. These analogues displayed improved oral exposure and activity in the Spinal Nerve Ligation (SNL) pain model.

MeSH terms

  • Administration, Oral
  • Animals
  • Chronic Pain / drug therapy
  • Disease Models, Animal
  • Heterocyclic Compounds, 3-Ring / chemical synthesis
  • Heterocyclic Compounds, 3-Ring / chemistry*
  • Heterocyclic Compounds, 3-Ring / therapeutic use
  • Humans
  • Pyrimidinones / chemical synthesis
  • Pyrimidinones / chemistry*
  • Pyrimidinones / therapeutic use
  • Rats
  • Receptors, Metabotropic Glutamate / antagonists & inhibitors*
  • Receptors, Metabotropic Glutamate / metabolism
  • Structure-Activity Relationship
  • Thiophenes / chemical synthesis
  • Thiophenes / chemistry*
  • Thiophenes / therapeutic use

Substances

  • Heterocyclic Compounds, 3-Ring
  • Pyrimidinones
  • Receptors, Metabotropic Glutamate
  • Thiophenes
  • metabotropic glutamate receptor type 1