Discovery of a new class of potent, selective, and orally bioavailable CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases

J Med Chem. 2008 Apr 10;51(7):2227-43. doi: 10.1021/jm701383e. Epub 2008 Mar 5.

Abstract

A novel chemical class of potent chemoattractant receptor-homologous expressed on Th2 lymphocytes (CRTH2 or DP2) antagonists is reported. An initial and moderately potent spiro-indolinone compound ( 5) was found during a high-throughput screening campaign. Structure-activity relationship (SAR) investigation around the carboxylic acid group revealed that changes in this part of the molecule could lead to a reversal of functional activity, yielding weakly potent agonists. SAR investigation of the succinimide functional group led to the discovery of several single-digit nanomolar antagonists. The potency of these compounds was confirmed in a human eosinophil chemotaxis assay. Moreover, compounds ( R)- 58 and ( R)- 71 were shown to possess pharmacokinetic properties suitable for development as an orally bioavailable drug.

MeSH terms

  • Animals
  • Binding Sites
  • Caco-2 Cells
  • Cell Membrane Permeability / drug effects
  • Crystallography, X-Ray
  • Cytochrome P-450 Enzyme Inhibitors
  • Dogs
  • Drug Design
  • Humans
  • Hypersensitivity / drug therapy*
  • Indoles / chemistry
  • Indoles / classification*
  • Indoles / pharmacology*
  • Inflammation / drug therapy
  • Male
  • Microsomes / drug effects
  • Microsomes / metabolism
  • Models, Molecular
  • Molecular Structure
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Immunologic / antagonists & inhibitors*
  • Receptors, Prostaglandin / antagonists & inhibitors*
  • Spiro Compounds / chemistry
  • Spiro Compounds / classification*
  • Spiro Compounds / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Cytochrome P-450 Enzyme Inhibitors
  • Indoles
  • Receptors, Immunologic
  • Receptors, Prostaglandin
  • Spiro Compounds
  • prostaglandin D2 receptor