Stable c-glycoside sugar and c-glycoconjugate mimetics,...

C - Chemistry – Metallurgy – 07 – H

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C07H 7/00 (2006.01) C07D 307/20 (2006.01) C07D 307/32 (2006.01) C07D 309/10 (2006.01) C07D 309/30 (2006.01)

Patent

CA 2650942

The invention concerns a C-glycoside compound of formula (I); wherein: n is equal to 1 or 2; Y represents H or halogen; X is an alkyl chain bearing at least one amino, amide, acid, ester, carbonyl, alcohol, aryl function or a carbonyl, ester amide, amino, alcohol group; the R's, identical or different, represent a OH or OR' group where R' is an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl, tertiobutyldiphenylsilyl group or one or more sugars; R1 represents OR', NR"R'", N3, or a phthalamide with R'' and R''', identical or different, represent H or an alkyl, aryl, benzyl, benzoyl, acetyl, alkoxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl group; R2 represents H or halogen or a OH, OR, NR"R"'or N3 group, as well as derivatives thereof in physiologically or pharmaceutically acceptable base, mineral or organic acid-addition salt, hydrate or solvate form. The invention is useful for preparing C-glycoside compounds or C-glycoconjugates applicable in particular in cosmetology, medical imagery, immunology for treating cancer, diabetes, hypertension.

L'invention concerne un composé C-glycoside de formule I : où n est égal à 1 ou 2, Y représente H ou un halogène, X est une chaîne alkyle possédant au moins une fonction aminé, amide, acide, ester, carbonyle, alcool, aryle ou un groupe carbonyle, ester amide, aminé, alcool, R identiques ou différents, représentent un groupement OH ou OR' où R' est un groupement alkyle, benzyle, benzoyle, acétyle, pivaloyle, trialkylsilyle, tertiobutyldiphénylsilyle ou un ou plusieurs sucres, R1 représente OR', NR"R'", N3, ou un phtalimide avec R"et R'", identiques ou différents, représentent H ou un groupe alkyle, aryle, benzyle, benzoyle, acétyle, alkyloxycarbonyle, allyloxycarbonyle, benzyloxycarbonyle, R2 représente H ou un halogène ou un groupement OH, OR, NR"R"'ou N3, ainsi que ses dérivés à l'état de base, de sel d'addition à un acide minéral ou organique, d'hydrate ou de solvat physiologiquement ou pharmaceutiquement acceptable. Elle s'applique à la préparation de composés C-glycosides ou C-glycoconjugués possédant des applications notamment en cosmétologie, imagerie médicale, immunologie, pour le traitement du cancer, du diabète, de l'hypertension.

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