Discovery of a potent and selective ROMK inhibitor with improved pharmacokinetic properties based on an octahydropyrazino[2,1-c][1,4]oxazine scaffold

Bioorg Med Chem Lett. 2016 Dec 1;26(23):5695-5702. doi: 10.1016/j.bmcl.2016.10.064. Epub 2016 Oct 24.

Abstract

Following the discovery of small molecule acyl piperazine ROMK inhibitors, the acyl octahydropyrazino[2,1-c][1,4]oxazine series was identified. This series displays improved ROMK/hERG selectivity, and as a consequence, the resulting ROMK inhibitors do not evoke QTc prolongation in an in vivo cardiovascular dog model. Further efforts in this series led to the discovery of analogs with improved pharmacokinetic profiles. This new series also retained comparable ROMK potency compared to earlier leads.

Keywords: Diuresis; Heart failure; Hypertension; Natriuresis; ROMK; hERG.

MeSH terms

  • Animals
  • Diuresis / drug effects
  • Dogs
  • Heart Failure / drug therapy
  • Humans
  • Hypertension / drug therapy
  • Macaca mulatta
  • Oxazines / chemistry*
  • Oxazines / pharmacokinetics
  • Oxazines / pharmacology*
  • Potassium Channels, Inwardly Rectifying / antagonists & inhibitors*
  • Potassium Channels, Inwardly Rectifying / metabolism
  • Rats, Sprague-Dawley
  • Transcriptional Regulator ERG / antagonists & inhibitors
  • Transcriptional Regulator ERG / metabolism

Substances

  • ERG protein, human
  • KCNJ1 protein, human
  • Oxazines
  • Potassium Channels, Inwardly Rectifying
  • Transcriptional Regulator ERG