Discovery of (1R,2R)-N-(4-(6-isopropylpyridin-2-yl)-3-(2-methyl-2H-indazol-5-yl)isothiazol-5-yl)-2-methylcyclopropanecarboxamide, a potent and orally efficacious mGlu5 receptor negative allosteric modulator

Bioorg Med Chem Lett. 2013 Mar 1;23(5):1249-52. doi: 10.1016/j.bmcl.2013.01.009. Epub 2013 Jan 12.

Abstract

A novel series of selective negative allosteric modulators (NAMs) for metabotropic glutamate receptor 5 (mGlu5) was discovered from an isothiazole scaffold. One compound of this series, (1R,2R)-N-(4-(6-isopropylpyridin-2-yl)-3-(2-methyl-2H-indazol-5-yl)isothiazol-5-yl)-2-methylcyclopropanecarboxamide (24), demonstrated satisfactory pharmacokinetic properties and, following oral dosing in rats, produced dose-dependent and long-lasting mGlu5 receptor occupancy. Consistent with the hypothesis that blockade of mGlu5 receptors will produce analgesic effects in mammals, compound 24 produced a dose-dependent reduction in paw licking responses in the formalin model of persistent pain.

MeSH terms

  • Allosteric Regulation / drug effects
  • Amides / chemistry*
  • Amides / pharmacokinetics
  • Amides / pharmacology*
  • Animals
  • Behavior, Animal / drug effects
  • Cyclopropanes / chemistry*
  • Cyclopropanes / pharmacokinetics
  • Cyclopropanes / pharmacology*
  • Glutamic Acid / chemistry
  • Glutamic Acid / metabolism
  • Indazoles / chemistry
  • Indazoles / pharmacokinetics
  • Indazoles / pharmacology
  • Male
  • Rats
  • Rats, Sprague-Dawley
  • Receptor, Metabotropic Glutamate 5 / chemistry
  • Receptor, Metabotropic Glutamate 5 / metabolism*
  • Thiazoles / chemistry
  • Thiazoles / pharmacokinetics
  • Thiazoles / pharmacology

Substances

  • Amides
  • Cyclopropanes
  • Grm5 protein, rat
  • Indazoles
  • Receptor, Metabotropic Glutamate 5
  • Thiazoles
  • Glutamic Acid
  • cyclopropanecarboxamide