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ID: ALA1142898

Journal: Bioorg Med Chem

Title: Synthesis and biological evaluation of benzoic acid derivatives as potent, orally active VLA-4 antagonists.

Authors: Chiba J, Iimura S, Yoneda Y, Watanabe T, Muro F, Tsubokawa M, Iigou Y, Satoh A, Takayama G, Yokoyama M, Takashi T, Nakayama A, Machinaga N.

Abstract: A series of benzoic acid derivatives was synthesized as VLA-4 antagonists. Introduction of chlorine or bromine into the 3-position on the central benzene of the diphenylurea portion as in lead compound 2 led to improvement in the pharmacokinetic properties. In particular, 12l demonstrated an acceptable plasma clearance and bioavailability in mice and rats as well as dogs (mice, CL=18.5 ml/min/kg,F=28%; rats, CL=5.2 ml/min/kg,F=36%; dogs, CL=3.6 ml/min/kg,F=55%). Additionally, 12l exhibited potent activity with an IC50 value of 0.51 nM and efficacy by oral administration at a dosage of 10 mg/kg in a rat pleurisy model.

CiteXplore: 17194595

DOI: 10.1016/j.bmc.2006.12.006