Carbohydrate mimetics having antiadhesive properties

Details Carbohydrate mimetics having antiadhesive properties Carbohydrate mimetics having antiadhesive properties

C - Chemistry, Metallurgy

07

H

C07H 15/207 (2006.01) A61K 31/70 (2006.01) C07H 3/04 (2006.01) C07H 3/06 (2006.01) C07H 15/04 (2006.01) C07H 17/04 (2006.01) C08G 73/06 (2006.01)

Patent

CA 2144388

The invention relates to carbohydrate mimetics having antiadhesive properties, and in particular a compound of the formula I Image I, in which R1 and R2 independently of one another are H, CH2X or CH2O(CH2)mX1 or together form a six-membered carbo- or hetero- cycle having at least one of the substituents R7, R8 and R9 and R3 is O, S, H or -CH2OX2 and R4 and R5 independently of one another are O-.alpha.-NANA, O-.beta.-NANA, O(CR10R11)nCOOH, OCX32(CR10R11)nCOOH, OSO3H or another monobasic acid and R6 is H, -OH or C1-C25-alkyl or with R3 forms a six-membered carbo- or heterocycle having at least one substituent X4 and Y is O-.alpha.-NANA, O-.beta.-NANA, O(CR10R11)pCOOH, OCX32(CR10R11)pCOOH, OSO3H or another monobasic acid and Z is a pyranose, a furanose or an open-chain polyalcohol and m, n, p and q independently of one another are a number from 1 to 20 and R7, R8, R9 X, X1, X2 and X4 independently of one another H, -NH2, -COOH, -OH, -CH2OH, -CH2NH, C1-C25-alkyl, aryl or -CH2O(CH2)qX, X3 is H, C1-C25-alkyl or aryl or alternatively X32 is =O or =S and R10 and R11 independently of one another are X or -CH2X or together form a six-mem- bered carbo- or heterocycle having at least one substituent X4, excluding the compounds sialyl-Lewis-X and -A and their derivatives which, instead of an N-acetyl group, carry the substituents N3, NH2 or OH or which, instead of fucose, carry glycerol, and also a process for the preparation of this compound, its use and pharmaceuticals and diagnostics prepared from it.

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