Substituted lactose derivatives as cell adhesion inhibitors

C - Chemistry – Metallurgy – 07 – H

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C07H 15/18 (2006.01) C07H 3/04 (2006.01) C07H 3/06 (2006.01) C07H 11/00 (2006.01) C07H 23/00 (2006.01)

Patent

CA 2138645

Compounds and methods of making them having formula (1) are described which bind to selectin receptors and thus mod- ulate the course of inflammation, cancer and related diseases by modulating cell-cell adhesion events. In formula (1), R1 is inde- pendently H or lower alkyl(1-4C); R2 is H, OH or lower alkyl(1-4C), alkylaryl or one or more additional saccharide resi- dues; R3 is a negatively charged moiety including S04--, P04--, or related group; Y is H or lower alkyl(1-4C); and X is -CHR4(CHOR1)2CHR50R1 wherein R4 and R5 are each independently H, lower alkyl(1-4C), or taken together result in a five- or six-membered ring optionally containing a heteroatom selected from the group consisting of O, S, and NR1; said five- or six-membered ring optionally substituted with one substituent selected from the group consisting of Rl, CH20R1, OR1, OOCR1, NR12, NHCOR1, and SR1 with the proviso that if X represents a hexose substituent R3 and R4, taken togeth- er, cannot provide a hexose substituent.

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