Discovery of pyrazine carboxamide CB1 antagonists: the introduction of a hydroxyl group improves the pharmaceutical properties and in vivo efficacy of the series

Bioorg Med Chem Lett. 2007 Jul 15;17(14):3978-82. doi: 10.1016/j.bmcl.2007.04.087. Epub 2007 Apr 29.

Abstract

Structure-activity relationships for a series of pyrazine carboxamide CB1 antagonists are reported. Pharmaceutical properties of the series are improved via inclusion of hydroxyl-containing sidechains. This structural modification sufficiently improved ADME properties of an orally inactive series such that food intake reduction was achieved in rat feeding models. Compound 35 elicits a 46% reduction in food intake in ad libidum fed rats 4-h post-dose.

MeSH terms

  • Amides / chemistry
  • Amides / pharmacology*
  • Animals
  • Pyrazinamide / analogs & derivatives*
  • Pyrazinamide / chemistry
  • Pyrazinamide / pharmacology
  • Rats
  • Receptor, Cannabinoid, CB1 / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Amides
  • Receptor, Cannabinoid, CB1
  • Pyrazinamide
  • pyrazinoic acid