2-Substituted piperazine-derived imidazole carboxamides as potent and selective CCK1R agonists for the treatment of obesity

Bioorg Med Chem Lett. 2008 Sep 1;18(17):4833-7. doi: 10.1016/j.bmcl.2008.07.083. Epub 2008 Jul 24.

Abstract

The discovery and structure-activity relationship of 1,2-diarylimidazole piperazine carboxamides bearing polar side chains as potent and selective cholecystokinin 1 receptor (CCK1R) agonists are described. Optimization of this series resulted in the discovery of isopropyl carboxamide 40, a CCK1R agonist with sub-nanomolar functional and binding activity as well as excellent potency in a mouse overnight food intake reduction assay.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Anti-Obesity Agents / chemical synthesis
  • Anti-Obesity Agents / chemistry
  • Anti-Obesity Agents / pharmacology*
  • Benzodiazepines / chemical synthesis
  • Benzodiazepines / chemistry
  • Benzodiazepines / pharmacology*
  • Chemokines, CC
  • Humans
  • Indoles / chemical synthesis
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Methylamines / chemical synthesis
  • Methylamines / chemistry
  • Methylamines / pharmacology
  • Mice
  • Obesity / drug therapy*
  • Piperazine
  • Piperazines / chemistry
  • Receptor, Cholecystokinin A / agonists*
  • Receptors, Cholecystokinin / agonists
  • Receptors, Cholecystokinin / chemistry
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / pharmacology*

Substances

  • Anti-Obesity Agents
  • Ccl28 protein, mouse
  • Chemokines, CC
  • GI 181771X
  • Indoles
  • Methylamines
  • Piperazines
  • Receptor, Cholecystokinin A
  • Receptors, Cholecystokinin
  • SR 146131
  • Thiazoles
  • Benzodiazepines
  • Piperazine