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AssigneeCytel Corporation
InventorsShawn A. DeFrees, Federico C. A. Gaeta, John J. Gaudino, Zhongli Zheng, Masaji Hayashi
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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 R.sup.1 Y is allyloxycarbonyl or chloroacetyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.18 straight chain, branched chain or cyclic hydrocarbyl, C.sub.1 -C.sub.6 alkyl C.sub.1 -C.sub.5 alkylene .omega.-carboxylate, .omega.-tri(C.sub.1 -C.sub.4 alkyl/phenyl)silyl C.sub.2 -C.sub.4 alkylene, monosaccharide or disaccharide, or OR.sup.2 together form a C.sub.1 -C.sub.18 straight chain, branched chain or cyclic hydrocarbyl carbamate; R.sup.3 is hydrogen or C.sub.1 -C.sub.6 acyl; R.sup.4 is hydrogen, C.sub.1 -C.sub.6 alkyl or benzyl; R.sup.5 is hydrogen, benzyl, methoxybenzyl, dimethoxybenzyl or C.sub.1 -C.sub.6 acyl; R.sup.7 is methyl or hydroxymethyl; and X is C.sub.1 -C.sub.6 acyloxy, C.sub.2 -C.sub.6 hydroxylacyloxy, hydroxy, halo or azido.
A compound of the formula ##STR43## wherein Z is hydrogen, C.sub.1 -C.sub.6 acyl or ##STR44## Y is selected from the group consisting of C(O), SO.sub.2, HNC(O), OC(O) and SC(O);
A compound of the formula ##STR46## Y is selected from the group consisting of C(O), SO.sub.2, HNC(O), OC(O) and SO(O);
A compound of the formula ##STR47## wherein Z is hydrogen, C.sub.1 -C.sub.6 acyl or ##STR48## Y is selected from the group consisting of C(O), SO.sub.2, HNC(O), OC(O) and SC(O);
A compound of the formula ##STR50## Y is selected from the group consisting of C(O), SO.sub.2, HNC(O), OC(O) and SO(O);
A pharmaceutical composition comprising a pharmaceutically acceptable diluent having dissolved or dispersed therein a cellular adhesion-inhibiting amount of a compound of the formula ##STR70## Y is selected from the group consisting of C(O), SO.sub.2, HNC(O), OC(O) and SC(O);
Dependencies are inferred from the claim text.