Biaryls as potent, tunable dual neurokinin 1 receptor antagonists and serotonin transporter inhibitors

Bioorg Med Chem Lett. 2015 Aug 1;25(15):3039-43. doi: 10.1016/j.bmcl.2015.04.098. Epub 2015 Jun 2.

Abstract

Depression is a serious illness that affects millions of patients. Current treatments are associated with a number of undesirable side effects. Neurokinin 1 receptor (NK1R) antagonists have recently been shown to potentiate the antidepressant effects of serotonin-selective reuptake inhibitors (SSRIs) in a number of animal models. Herein we describe the optimization of a biaryl chemotype to provide a series of potent dual NK1R antagonists/serotonin transporter (SERT) inhibitors. Through the choice of appropriate substituents, the SERT/NK1R ratio could be tuned to afford a range of target selectivity profiles. This effort culminated in the identification of an analog that demonstrated oral bioavailability, favorable brain uptake, and efficacy in the gerbil foot tap model. Ex vivo occupancy studies with compound 58 demonstrated the ability to maintain NK1 receptor saturation (>88% occupancy) while titrating the desired level of SERT occupancy (11-84%) via dose selection.

Keywords: NK(1); Neurokin 1; Neuroscience discovery; SERT; SSRI; Serotonin transport inhibitors.

MeSH terms

  • Animals
  • Antidepressive Agents / chemistry
  • Antidepressive Agents / pharmacokinetics
  • Antidepressive Agents / pharmacology
  • Biphenyl Compounds / chemistry*
  • Biphenyl Compounds / pharmacokinetics
  • Biphenyl Compounds / pharmacology*
  • Brain / drug effects
  • Brain / metabolism
  • Depression / drug therapy
  • Depression / metabolism
  • Gerbillinae
  • Humans
  • Neurokinin-1 Receptor Antagonists / chemistry*
  • Neurokinin-1 Receptor Antagonists / pharmacokinetics
  • Neurokinin-1 Receptor Antagonists / pharmacology*
  • Selective Serotonin Reuptake Inhibitors / chemistry*
  • Selective Serotonin Reuptake Inhibitors / pharmacokinetics
  • Selective Serotonin Reuptake Inhibitors / pharmacology*
  • Serotonin / metabolism
  • Serotonin Plasma Membrane Transport Proteins / metabolism

Substances

  • Antidepressive Agents
  • Biphenyl Compounds
  • Neurokinin-1 Receptor Antagonists
  • Serotonin Plasma Membrane Transport Proteins
  • Serotonin Uptake Inhibitors
  • Serotonin