Novel, potent, selective and brain penetrant vasopressin 1b receptor antagonists

Bioorg Med Chem Lett. 2018 Oct 15;28(19):3260-3264. doi: 10.1016/j.bmcl.2018.07.043. Epub 2018 Jul 31.

Abstract

Herein we report the discovery of a novel oxindole-based series of vasopressin 1b (V1b) receptor antagonists. Introducing a substituted piperazine moiety and optimizing the southern and the northern aromatic rings resulted in potent, selective and brain penetrant V1b receptor antagonists. Compound 9c was found to be efficacious in a rat model of anti-depressant activity (3 mg/kg, ip). Interestingly, both moderate terminal half-life and moderate bioavailability could be achieved despite sub-optimal microsomal stability.

Keywords: Oxindole; SSR149415; V1b; Vasopressin 1b.

MeSH terms

  • Animals
  • Antidepressive Agents / pharmacokinetics
  • Antidepressive Agents / pharmacology
  • Antidiuretic Hormone Receptor Antagonists / pharmacokinetics*
  • Antidiuretic Hormone Receptor Antagonists / pharmacology*
  • Biological Availability
  • Brain / metabolism
  • Half-Life
  • Humans
  • Microsomes / metabolism
  • Models, Animal
  • Rats
  • Structure-Activity Relationship

Substances

  • Antidepressive Agents
  • Antidiuretic Hormone Receptor Antagonists