Drug – bio-affecting and body treating compositions – In vivo diagnosis or in vivo testing
Patent
1995-06-06
1997-10-21
Hutzell, Paula K.
Drug, bio-affecting and body treating compositions
In vivo diagnosis or in vivo testing
424 92, 424 96, 514 54, A61K 4900, A61K 31715, G01N 3100, G01N 3348
Patent
active
056793219
ABSTRACT:
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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Dasgupta Falguni
Musser John Henry
Glycomed Incorporated
Hutzell Paula K.
Minnifield N. M.
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