New gem-difluoride c-glycoside compounds derived from...

C - Chemistry – Metallurgy – 07 – H

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C07H 7/00 (2006.01) A61K 31/70 (2006.01)

Patent

CA 2650384

The invention relates to a gem-difluoride glycoconjugated compound with formula (I): where R represents H or a benzyl, acetyl, benzoyl alkyl group, R1 and R2 may be identical or different and represent H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl, tertiobutyl- diphenylsilyl protective group or an acetal group of the CR'R' type, where R' and R' may be identical or different and represent H or an alkyl, aryl, benzyl or thiophene group, R3 represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, R4 represents OR'', NGR'GR', N3, or a phthalimide, where R'' represents H or an alkyl, benzyl, benzoyle, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, GR' and GR' may be identical or different and represent H or an alkyl, benzyl, benzoyl, acetyl, alkyloxycarbonyl, allyloxycarbonyl or benzyloxycarbonyl group, R5 represents a free or protected hydroxyl group or a halogen, R6 represents H or an alkyl, acetyl, benzyl, PO3H or PO3Na group. It is applicable to the preparation of compounds that can be used particularly for the treatment of cancer.

L'invention concerne un composé glycoconjugué gem-difluoré de formule (I): où R représente H ou un groupe alkyle, benzyle, acétyle, benzoyle, R1 et R2, identiques ou différents, représentent H ou un groupe protecteur alkyle, benzyle, benzoyle, acétyle, pivaloyle, trialkylsilyle, tertiobutyl- diphénylsilyle ou un groupe acétal, du type CR'R", avec R'et R", identiques ou différents, représentent H ou un groupe alkyle, aryle, benzyle, thiophène, R3 représente H ou un groupe protecteur alkyle, benzyle, benzoyle, acétyle, pivaloyle, trialkylsilyle, tertiobutyldiphénylsilyle, R4 représente OR'", NGR'GR", N3, ou un phtalimide, avec R'" représente un H ou un groupe protecteur alkyle, benzyle, benzoyle, acétyle, pivaloyle, trialkylsilyle, tertiobutyldiphénylsilyle, GR' et GR", identiques ou différents, représentent H ou un groupe alkyle, benzyle, benzoyle, acétyle, alkyloxycarbonyle, allyloxycarbonyle, benzyloxycarbonyle, R5 représente un groupe hydroxyle libre ou protégé ou un halogène, R6 représente H ou un groupe alkyle, acétyle, benzyle, PO3H, PO3Na. Elle s'applique à la préparation de composés utilisables notamment pour le traitement du cancer.

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