Discovery of N-[(1S,2S)-3-(4-Chlorophenyl)-2- (3-cyanophenyl)-1-methylpropyl]-2-methyl-2- {[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide (MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity

J Med Chem. 2006 Dec 28;49(26):7584-7. doi: 10.1021/jm060996+.

Abstract

The discovery of novel acyclic amide cannabinoid-1 receptor inverse agonists is described. They are potent, selective, orally bioavailable, and active in rodent models of food intake and body weight reduction. A major focus of the optimization process was to increase in vivo efficacy and to reduce the potential for formation of reactive metabolites. These efforts led to the identification of compound 48 for development as a clinical candidate for the treatment of obesity.

MeSH terms

  • Animals
  • Anti-Obesity Agents / chemical synthesis
  • Anti-Obesity Agents / chemistry
  • Anti-Obesity Agents / pharmacology*
  • Body Weight / drug effects
  • Cannabinoids / chemical synthesis
  • Cannabinoids / chemistry
  • Cannabinoids / pharmacology*
  • Cyclic AMP / metabolism
  • Eating / drug effects
  • Humans
  • Liver / drug effects
  • Liver / metabolism
  • Microsomes / drug effects
  • Microsomes / metabolism
  • Obesity / drug therapy*
  • Rats
  • Receptor, Cannabinoid, CB1 / agonists*
  • Receptor, Cannabinoid, CB1 / antagonists & inhibitors
  • Receptor, Cannabinoid, CB1 / metabolism
  • Receptor, Cannabinoid, CB2 / agonists*
  • Receptor, Cannabinoid, CB2 / antagonists & inhibitors
  • Receptor, Cannabinoid, CB2 / metabolism

Substances

  • Anti-Obesity Agents
  • Cannabinoids
  • Receptor, Cannabinoid, CB1
  • Receptor, Cannabinoid, CB2
  • Cyclic AMP