Sugar modified nucleosides and their use for synthesis of...

Details Sugar modified nucleosides and their use for synthesis of... Sugar modified nucleosides and their use for synthesis of...

C - Chemistry, Metallurgy

07

H

C07H 19/04 (2006.01) C07D 239/47 (2006.01) C07D 239/54 (2006.01) C07D 403/04 (2006.01) C07D 405/04 (2006.01) C07D 409/04 (2006.01) C07D 473/18 (2006.01) C07D 473/34 (2006.01) C07H 21/00 (2006.01)

Patent

CA 2202280

A number of modified nucleosides are disclosed composed of modified sugar moieties which contain substituents at C1 and C4 positions, or branched substituents at C3 and C5 positions of deoxyribose or ribose. Each nucleoside is converted to or properly protected and them converted to the corresponding phosphoramidites. These phosphoramidites are used to assemble oligonucleotides in which there is at least one of the forenoted nucleosides. These sugar modified oligonucleotides have the potential to be used as antisense therapies since they are expected to enhance nuclease resistance and cellular uptake while they maintain sequence-specificity and affinity to nucleic acid targets in vitro or in vivo.

On décrit un certain nombre de nucléosides modifiés ayant des groupes sucre modifiés, avec des substituants dans les positions C1 et C4 ou des substituants ramifiés dans les positions C3 et C5 du désoxyribose ou du ribose. Chaque nucléoside est converti ou d'abord protégé de manière appropriée et ensuite converti en phosphoramidite correspondant. Ces phosphoramidites sont utilisés pour réaliser par assemblage des oligonucléotides contenant au moins un des nucléosides en question. Ces oligonucléotides modifiés au niveau du groupe sucre peuvent être utilisés dans des thérapies antisens car on peut prévoir qu'ils vont augmenter la résistance aux nucléases et que leur absorption par les cellules sera améliorée, alors qu'ils vont conserver leur spécificité et leur affinité pour les acides nucléiques cibles in vitro ou in vivo.

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