Discovery of novel and potent leukotriene B4 receptor antagonists. Part 1

J Med Chem. 2010 May 13;53(9):3502-16. doi: 10.1021/jm1001919.

Abstract

The inhibition of LTB(4) binding to and activation of G-protein-coupled receptors BLT1 and BLT2 is the premise of a treatment for several inflammatory diseases. In a lead optimization effort starting with the leukotriene B(4) (LTB(4)) receptor antagonist (2), members of a series of 3,5-diarylphenyl ethers were found to be highly potent inhibitors of LTB(4) binding to BLT1 and BLT2 receptors, with varying levels of selectivity depending on the substitution. In addition, compounds 33 and 38 from this series have good in vitro ADME properties, good oral bioavailability, and efficacy after oral delivery in guinea pig LTB(4) and nonhuman primate allergen challenge models. Further profiling in a rat non-GLP toxicity experiment provided the rationale for differentiation and selection of one compound (33) for clinical development.

MeSH terms

  • Animals
  • Drug Discovery*
  • Drug Evaluation, Preclinical
  • Guinea Pigs
  • HL-60 Cells
  • Humans
  • Leukotriene Antagonists / chemistry*
  • Leukotriene Antagonists / pharmacology
  • Phenyl Ethers / chemistry
  • Phenyl Ethers / pharmacology*
  • Primates
  • Protein Binding
  • Rats
  • Receptors, G-Protein-Coupled / metabolism
  • Receptors, Leukotriene B4 / antagonists & inhibitors*
  • Receptors, Leukotriene B4 / metabolism
  • Structure-Activity Relationship

Substances

  • LTB4R protein, human
  • LTB4R2 protein, human
  • Leukotriene Antagonists
  • Phenyl Ethers
  • Receptors, G-Protein-Coupled
  • Receptors, Leukotriene B4