Identification of 4-[1-[3-chloro-4-[N'-(5-fluoro-2-methylphenyl)ureido]phenylacetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]benzoic acid as a potent, orally active VLA-4 antagonist

Bioorg Med Chem. 2008 Dec 1;16(23):9991-10000. doi: 10.1016/j.bmc.2008.10.020. Epub 2008 Oct 12.

Abstract

Optimization of benzoic acid derivatives by introducing substituents into the diphenyl urea moiety led to the identification of compound 20l as a potent VLA-4 antagonist. Compound 20l inhibited eosinophil infiltration into bronchial alveolar lavage fluid in a murine asthma model by oral dosing and its efficacy was comparable to anti-mouse alpha4 antibody (R1-2). Furthermore, this compound significantly blocked bronchial hyper-responsiveness in the model.

MeSH terms

  • Administration, Oral
  • Animals
  • Anti-Inflammatory Agents / pharmacology
  • Asthma / drug therapy
  • Benzoates / administration & dosage
  • Benzoates / chemical synthesis
  • Benzoates / pharmacology*
  • Cells, Cultured
  • Disease Models, Animal
  • Dogs
  • Female
  • Inhibitory Concentration 50
  • Integrin alpha4beta1 / antagonists & inhibitors*
  • Mice
  • Mice, Inbred BALB C
  • Permeability
  • Pyrroles / administration & dosage
  • Pyrroles / chemical synthesis
  • Pyrroles / pharmacology*
  • Rats

Substances

  • 4-(1-(3-chloro-4-(N'-(5-fluoro-2-methylphenyl)ureido)phenylacetyl)-(4S)-fluoro-(2S)-pyrrolidinylmethoxy)benzoic acid
  • Anti-Inflammatory Agents
  • Benzoates
  • Integrin alpha4beta1
  • Pyrroles