1-Sulfonyl-4-acylpiperazines as selective cannabinoid-1 receptor (CB1R) inverse agonists for the treatment of obesity

J Med Chem. 2009 Apr 23;52(8):2550-8. doi: 10.1021/jm900063x.

Abstract

A novel series of 1-sulfonyl-4-acylpiperazines as selective cannabinoid-1 receptor (CB1R) inverse agonists was discovered through high throughput screening (HTS) and medicinal chemistry lead optimization. Potency and in vivo properties were systematically optimized to afford orally bioavailable, highly efficacious, and selective CB1R inverse agonists that caused food intake suppression and body weight reduction in diet-induced obese rats and dogs. It was found that the receptor binding assay predicted in vivo efficacy better than functional antagonist/inverse agonist activities. This observation expedited the structure-activity relationship (SAR) analysis and may have implications beyond the series of compounds presented herein.

MeSH terms

  • Animals
  • Anti-Obesity Agents / chemical synthesis*
  • Anti-Obesity Agents / chemistry
  • Anti-Obesity Agents / pharmacology
  • Biological Availability
  • Body Weight / drug effects
  • Dogs
  • Drug Inverse Agonism
  • Eating / drug effects
  • Hepatocytes / metabolism
  • Humans
  • In Vitro Techniques
  • Macaca mulatta
  • Microsomes, Liver / metabolism
  • Models, Molecular
  • Piperazines / chemical synthesis*
  • Piperazines / chemistry
  • Piperazines / pharmacology
  • Rats
  • Receptor, Cannabinoid, CB1 / antagonists & inhibitors*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology

Substances

  • Anti-Obesity Agents
  • Piperazines
  • Receptor, Cannabinoid, CB1
  • Sulfonamides