Cytel Corporation

John J Gaudino

Federico C Gaeta

Zhongli Zheng

Masaji Hayashi

Shawn A DeFrees

Shawn De Frees

The present invention relates to analogues of sialyl Le.sup.x the inhibit cellular adhesion between a selectin and cell that express sialyl Le.sup.x on their surfaces, as well as methods and compositions using the same, intermediates and methods for the preparation of the celluar adhesion inhibitor compounds and their intermediates. A contemplated intermediate or inhibitor compound has a structure that corresponds to that of Formula A, ##STR1## wherein: Z is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 acyl and ##STR2##

Sialyl Le.sup.x analogues as inhibitors of cellular adhesion

The inventive compounds are analogues of sialyl Le.sup.x that inhibit cellular adhesion between a selectin and cells that express sialyl Le.sup.x on their surfaces, and their synthetic intermediates. An inventive compound has structure A, ##STR1## wherein Z is hydrogen, C.sub.1 -C.sub.6 acyl or ##STR2## Y is C(O), SO.sub.2, HNC(O), OC(O) or SC(O); R.sup.1 is an aryl, a substituted aryl or a phenyl C.sub.1 -C.sub.3 alkylene group, wherein an aryl group has one five- or six-membered aromatic ring, a fused five/six-membered aromatic ring, or two fused six-membered aromatic rings, which rings are hydrocarbyl, monooxahydrocarbyl, monothiahydrocarbyl, monoazahydrocarbyl or diazahydrocarbyl rings, and a substituted aryl group is an aryl group having a halo, trifluoromethyl, nitro, C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy, amino, mono-C.sub.1 -C.sub.18 alkylamino, di-C.sub.1 -C.sub.18 alkylamino, benzylamino, C.sub.1 -C.sub.18 alkylbenzylamino, C.sub.1 -C.sub.18 thioalkyl or C.sub.1 -C.sub.18 alkyl carboxamido substituent, or

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Westlake Village, CA, United States of America

John J Gaudino