Development of an in vivo active, dual EP1 and EP3 selective antagonist based on a novel acyl sulfonamide bioisostere

Bioorg Med Chem Lett. 2013 Jan 1;23(1):37-41. doi: 10.1016/j.bmcl.2012.11.046. Epub 2012 Nov 24.

Abstract

Recent preclinical studies demonstrate a role for the prostaglandin E(2) (PGE(2)) subtype 1 (EP1) receptor in mediating, at least in part, the pathophysiology of hypertension and diabetes mellitus. A series of amide and N-acylsulfonamide analogs of a previously described picolinic acid-based human EP1 receptor antagonist (7) were prepared. Each analog had improved selectivity at the mouse EP1 receptor over the mouse thromboxane receptor (TP). A subset of analogs gained affinity for the mouse PGE(2) subtype 3 (EP3) receptor, another potential therapeutic target. One analog (17) possessed equal selectivity for EP1 and EP3, displayed a sufficient in vivo residence time in mice, and lacked the potential for acyl glucuronide formation common to compound 7. Treatment of mice with 17 significantly attenuated the vasopressor activity resulting from an acute infusion of EP1 and EP3 receptor agonists. Compound 17 represents a potentially novel therapeutic in the treatment of hypertension and diabetes mellitus.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Diabetes Mellitus / drug therapy
  • Half-Life
  • Humans
  • Hypertension / drug therapy
  • Mice
  • Microsomes, Liver / metabolism
  • Pyridines / chemistry*
  • Pyridines / pharmacokinetics
  • Pyridines / therapeutic use
  • Receptors, Prostaglandin E, EP1 Subtype / antagonists & inhibitors*
  • Receptors, Prostaglandin E, EP1 Subtype / metabolism
  • Receptors, Prostaglandin E, EP3 Subtype / antagonists & inhibitors*
  • Receptors, Prostaglandin E, EP3 Subtype / metabolism
  • Receptors, Thromboxane / antagonists & inhibitors
  • Receptors, Thromboxane / metabolism
  • Structure-Activity Relationship
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacokinetics
  • Sulfonamides / therapeutic use

Substances

  • Pyridines
  • Receptors, Prostaglandin E, EP1 Subtype
  • Receptors, Prostaglandin E, EP3 Subtype
  • Receptors, Thromboxane
  • Sulfonamides