Fluorine-substituted ganglioside gm3 derivative and...

C - Chemistry – Metallurgy – 07 – H

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C07H 15/10 (2006.01) A61K 31/70 (2006.01) C07H 13/02 (2006.01) C07H 13/04 (2006.01) C07H 23/00 (2006.01)

Patent

CA 2213256

A novel fluorine-substituted ganglioside GM3 derivative represented by the formula (I): (see formula I) wherein R is an aliphatic acyl group, R1 is a hydrogen atom or a lower alkyl group, R2, R3, R4 and R6 represent independently of one another a hydrogen atom, an aliphatic lower acyl group or an aromatic acyl group, R5 is an straight or branched, saturated or unsaturated aliphatic hydrocarbon group having 1 to 30 carbon atoms, and n is an integer of 0 to 20, provided that when R1 is a hydrogen atom, R2, R3, R4 and R6 are hydrogen atoms, or when R1 is a lower alkyl group, R2, R3, R4 and R6 are each an aliphatic lower acyl group or an aromatic acyl group.

L'invention porte sur de nouveaux analogues de gangliosides fluorés GM3 et leurs intermédiaires, représentés par la formule générale (I) dans laquelle R reprséente un acyle aliphatique, R<1> représente un hydrogène ou un alkyle de faible poids moléculaire, R<2>, R<3>, R<4> et R<6> sont identiques ou différents, chacun représentant un hydrogène, un acyle aliphatique de faible poids moléculaire ou un acyle aromatique, à la condition que lorsque R<1> représente un hydrogène, R<2>, R<3>, R<4> et R<6> représentent alors un hydrogène et que, lorsque R<1> représente un alkyle de faible poids moléculaire, R<2>, R<3>, R<4> et R<6> représentent alors chacun un acyle aliphatique ou aromatique. Dans cette même formule, R<5> représente un groupe carbure d'hydrogène aliphatique posséedant de 1 à 30 atomes de carbone, linéaire ou ramifié, saturé ou insaturé tandis que n est un nombre entier valant de 0 à 20.

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