Design and synthesis of orally-active and selective azaindane 5HT2c agonist for the treatment of obesity

Bioorg Med Chem Lett. 2010 Jan 1;20(1):266-71. doi: 10.1016/j.bmcl.2009.10.112. Epub 2009 Oct 30.

Abstract

Based on our original pyrazine hit, CP-0809101, novel conformationally-restricted 5HT2c receptor agonists with 2-piperazin-azaindane scaffold were designed. Synthesis and structure-activity relationship (SAR) studies are described with emphasis on optimization of the selectivity against 5HT2a and 5HT2b receptors with excellent 2c potency. Orally-active and selective compounds were identified with dose-responsive in vivo efficacy in our pre-clinical food intake model.

MeSH terms

  • Administration, Oral
  • Animals
  • Anti-Obesity Agents / chemical synthesis*
  • Anti-Obesity Agents / chemistry
  • Anti-Obesity Agents / pharmacology
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry
  • Aza Compounds / pharmacology
  • Dogs
  • Drug Design
  • Haplorhini
  • Humans
  • Obesity / drug therapy
  • Rats
  • Receptor, Serotonin, 5-HT2C / metabolism
  • Serotonin 5-HT2 Receptor Agonists*
  • Serotonin Receptor Agonists / chemical synthesis*
  • Serotonin Receptor Agonists / chemistry
  • Serotonin Receptor Agonists / pharmacology

Substances

  • Anti-Obesity Agents
  • Aza Compounds
  • Receptor, Serotonin, 5-HT2C
  • Serotonin 5-HT2 Receptor Agonists
  • Serotonin Receptor Agonists