Sulfated .beta.-glycolipid derivatives as cell adhesion inhibito

Details Sulfated .beta.-glycolipid derivatives as cell adhesion inhibito Sulfated .beta.-glycolipid derivatives as cell adhesion inhibito

1996-02-12

1996-10-15

Kunz, Gary L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

536 175, 536 176, 536 179, A61K 3170, C07H 1100

Patent

active

055654339

ABSTRACT:
There is provided novel sulfated p-glycolipid compounds of the formula ##STR1## wherein R is an acyl residue of a fatty acid;
R.sup.1 is --(CH.dbd.CH).sub.m --(CH.sub.2).sub.n --CH.sub.3 ;
R.sup.2, R.sup.3, R.sup.4 and R.sup.6 each are independently --SO.sub.3 H, hydrogen, unsubstituted or substituted alkanoyl, arylalkyl or arylcarbonyl wherein said substituent is selected from the group consisting of halogen, C.sub.1-4 alkyl, trifluoromethyl, hydroxy and C.sub.1-4 alkoxy; or R.sub.4 and R.sub.6, taken together are isopropylidene; provided at least two of R.sup.2, R.sup.3, R.sup.4 and R.sup.6 are --SO.sub.3 H;
R.sup.5 is hydrogen, unsubstituted or substituted alkanoyl, arylalkyl or arylcarbonyl wherein said substituent is selected from the group consisting of halogen, C.sub.1-4 alkyl, trifluoromethyl, hydroxy and C.sub.1-4 alkoxy;
m is an integer of 0 or 1;
n is an integer of from 5 to 14, inclusive;
or a non-toxic pharmaceutically acceptable salt, solvate or hydrate thereof which are inhibitors of selectin-mediated cellular adhesion and are useful in the treatment or prevention of inflammatory diseases and other pathological conditions in mammals.

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