Sialic acid/fucose based medicaments

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United States of America Patent

PATENT NO 5679321
SERIAL NO

08468788

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Abstract

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Compounds that are synthetically inexpensive to make relative to the naturally occurring selectin ligands and that retain selectin binding activity are described that have a three-dimensionally stable configuration for sialic acid and fucose, or analogs or derivatives of these groups, such that sialic acid and fucose are separated by a non-carbohydrate linker that permits binding between those groups and the selectins, such compounds being represented by the following general structural formula I(a): ##STR1## wherein m and n are independently an integer of from 1 to 5, Y and Z are independently a connecting moiety selected from the group consisting of --CH.sub.2 --, --O--, --S--, --NR' and --NR'R'-- (wherein R' and R' are independently H or an alkyl containing 1 to 4 carbon atoms); X is a connecting moiety which is selected from the group consisting of --O--, --S-- and --N--; and --R'' may be --R' or any moiety which does not interfere with the three-dimensional configuration of A or B so as to interfere with selectin binding and is preferably a moiety selected from the group consisting of --OR', --SR', --I, --N.sub.3, and --NR'R', and A is selected from the group consisting of .alpha. and .beta. forms of sialic acid, Kemp's acid, Quinic acid, Glyceric acid, Lactic acid and acetic acid, and esters thereof and B is selected from the group consisting of .alpha. and .beta. forms of L-Fucose and esters and substituted forms thereof wherein one or more of the --OH groups is independently --F, or --NR.sup.IV, R.sup.V wherein R.sup.IV and R.sup.V are independently an alkyl contain 1 to 5 carbons.

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Patent Owner(s)

  • GLYCOMED INCORPORATED

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Inventor(s)

Inventor Name Address # of filed Patents Total Citations
Dasgupta, Falguni Alameda, CA 14 349
Musser, John Henry San Carlos, CA 9 214

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