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Bioorg Med Chem Lett. 2003 Feb 10;13(3):561-6.

Design, synthesis and structure-activity relationships of benzoxazinone-based factor Xa inhibitors.

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1
Millennium Pharmaceuticals, Inc., 256 E. Grand Avenue, South San Francisco, CA 94080, USA.

Abstract

A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds 1 and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively.

PMID:
12565972
DOI:
10.1016/s0960-894x(02)00927-7
[Indexed for MEDLINE]

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