Gem-difluoride c-glycopeptide compounds, their preparation...

C - Chemistry – Metallurgy – 07 – D

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C07D 309/10 (2006.01) A61K 8/49 (2006.01) A61K 31/351 (2006.01) A61P 29/00 (2006.01) A61Q 5/00 (2006.01) A61Q 17/04 (2006.01) A61Q 19/00 (2006.01) C07H 7/00 (2006.01) C07K 5/068 (2006.01)

Patent

CA 2649993

The invention relates to a gem-difluoride C-glycopeptide compound with formula I where n is an integer equal to 3 or 4, R represents a hydrogen atom, an alkyl, benzyl, acetyl, trimethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl group, R´ represents OR, NR'R'', N3, or a phthalimide, R' and R'' represent a hydrogen atom or an alkyl, aryl, benzyl, benzoyl, acetyl, alkyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl group, R1 represents a hydrogen atom or an alkyl, benzyl, alkylcarbamate, allylcarbamate, benzylcarbamate, acetyl group, R1 may consist of an amino acid if R2 represents only OR, R2 includes an amino acid if R1 represents a hydrogen atom or an alkyl, benzyl, alkylcarbamate, allylcarbamate, benzylcarbamate, acetyl group, R2 represents OR when R1 represents an amino acid, R3 represents a hydrogen atom or a free or protected alcohol function. It is applicable to the preparation of compounds or compositions to be used for preservation of biological materials such as cells, tissues and organs at various temperatures.

L'invention concerne un composé C-glycopeptide gem-difluoré de formule I où n est un nombre entier égal à 3 ou 4, R représente un atome d'hydrogène, un groupe alkyle, benzyle, acétyle, triméthylsilyle, tert-butyldiméthylsilyle, tert-butyldiphénylsilyle, R´ représente OR, NR"R'", N3, ou un phtalimide, R" et R'" représentent un atome d'hydrogène ou un groupe alkyle, aryle, benzyle, benzoyle, acétyle, alkyloxycarbonyle, allyloxycarbonyle, benzyloxycarbonyle, R1 représente un atome d'hydrogène ou un groupe alkyle, benzyle, alkylcarbamate, allylcarbamate, benzylcarbamate, acétyle, R1 peut consister en un acide aminé dans le cas où R2 représente uniquement OR, R2 comprend un acide aminé dans le cas où R1 représente un atome d'hydrogène ou un groupe alkyle, benzyle, alkylcarbamate, allylcarbamate, benzylcarbamate, acétyle, R2 représente OR quand R1 représente un acide aminé, R3 représente un atome d'hydrogène ou une fonction alcool libre ou protégé. Elle s'applique à la préparation de composés ou compositions utilisables pour la préservation de matériaux biologiques tels que des cellules, tissus et organes à différentes températures.

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