Naphthalene/quinoline amides and sulfonylureas as potent and selective antagonists of the EP4 receptor

Bioorg Med Chem Lett. 2011 Feb 1;21(3):1041-6. doi: 10.1016/j.bmcl.2010.12.014. Epub 2010 Dec 8.

Abstract

Two new series of EP(4) antagonists based on naphthalene/quinoline scaffolds have been identified as part of our on-going efforts to develop treatments for inflammatory pain. One series contains an acidic sulfonylurea pharmacophore, whereas the other is a neutral amide. Both series show subnanomolar intrinsic binding potency towards the EP(4) receptor, and excellent selectivity towards other prostanoid receptors. While the amide series generally displays poor pharmacokinetic parameters, the sulfonylureas exhibit greatly improved profile. MF-592, the optimal compound from the sulfonylurea series, has a desirable overall preclinical profile that suggests it is suitable for further development.

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Amides / pharmacokinetics
  • Animals
  • Dogs
  • Drug Evaluation, Preclinical
  • Humans
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Indoles / pharmacokinetics
  • Naphthalenes / chemistry*
  • Quinolines / chemistry*
  • Rats
  • Receptors, Prostaglandin E, EP4 Subtype / antagonists & inhibitors*
  • Receptors, Prostaglandin E, EP4 Subtype / metabolism
  • Structure-Activity Relationship
  • Sulfonylurea Compounds / chemical synthesis
  • Sulfonylurea Compounds / chemistry*
  • Sulfonylurea Compounds / pharmacokinetics

Substances

  • Amides
  • Indoles
  • MF 592
  • Naphthalenes
  • Quinolines
  • Receptors, Prostaglandin E, EP4 Subtype
  • Sulfonylurea Compounds
  • naphthalene
  • quinoline