Oligonucleotide analogues

Details Oligonucleotide analogues Oligonucleotide analogues

C - Chemistry, Metallurgy

07

H

C07H 21/00 (2006.01) A61K 31/70 (2006.01) C07H 23/00 (2006.01)

Patent

CA 2247480

An oligonucleotide analogue having 10 to 200 natural and/or synthetic nucleoside units, linked by internucleoside linkages, at least one of the internucleoside linkages being of formula (I), where the indicated methylene group is attached to a 3' carbon atom of a nucleoside, the indicated oxygen atom is attached to a 5' carbon atom of an adjacent nucleoside, R1 is hydrogen, hydroxy, O-, thiol, S-, -NH2 or a group of formula R1a, -OR1a, - SR1a, -NHR1b or -NR1bR1c where R1a is an unsubstituted or substituted C1 to C10 alkyl, C2 to C10 alkenyl, C3 to C8 cycloalkyl, C6 to C10 aryl or C7 to C13 aralkyl group and R1b and R1c are each independently an unsubstituted or substituted C1 to C10 alkyl, C2 to C10 alkenyl, C3 to C8 cycloalkyl, C6 to C10 aryl or C7 to C13 aralkyl group or R1b and R1c together with the nitrogen atom to which they are attached denote a five- or six-membered heterocyclic ring, and X is oxygen or sulphur.

La présente invention concerne un analogue d'oligonucléotide comportant de 10 à 200 unités nucléosides naturelles et/ou synthétiques, reliées par des liaisons internucléosides, l'une au moins des liaisons internucléosides étant représentée par la formule générale (I). Lorsque le groupe méthylène considéré se rattache à un atome de carbone en 3' d'un nucléoside, l'atome d'oxygène considéré se rattache à un atome de carbone en 5' d'un nucléoside adjacent. R?1¿ est hydrogène, hydroxy, O?-¿, thiol, -NH¿2? ou un groupe de formule R?1¿¿a?, -OR?1¿¿a?, -SR?1¿¿a?, -NHR?1¿¿b? ou -NR?1¿¿b?R?1¿¿c?; R?1¿¿a? est un groupe C¿1?-C¿10? alkyl, C¿2?-C¿10? alcényl, C¿3?-C¿8? cycloalkyle, C¿6?-C¿10? aryl ou C¿7?-C¿13? aralkyl substitué ou non substitué; R?1¿¿b? et R?1¿¿c? sont indépendamment chacun un groupe C¿1?-C¿10? alkyl, C¿2?-C¿10? alcényl, C¿3?-C¿8? cycloalkyle, C¿6?-C¿10? aryl ou C¿7?-C¿13? aralkyl substitué ou non substitué ou bien R?1¿¿b? et R?1¿¿c? forment ensemble avec l'atome d'azote auquel ils se rattachent un cycle hétérocyclique à cinq ou six segments. X est oxygène ou soufre.

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