The present invention provides 6-modified bicyclic nucleoside analogs and oligomeric compounds comprising these nucleoside analogs. In preferred embodiments the nucleoside analogs have either (R) or (S)-chirality at the 6-position. These bicyclicnucleoside analogs are useful for enhancing properties
The present invention provides 6-modified bicyclic nucleoside analogs and oligomeric compounds comprising these nucleoside analogs. In preferred embodiments the nucleoside analogs have either (R) or (S)-chirality at the 6-position. These bicyclicnucleoside analogs are useful for enhancing properties of oligomeric compounds including nuclease resistance.
대표청구항▼
What is claimed is: 1. An oligomeric compound having at least one monomer of formula: or of formula: or of formula: wherein independently for each of said at least one monomer of formula I, II or III: Bx is a heterocyclic base moiety; T3 and T4 are each, independently, an internucleosid
What is claimed is: 1. An oligomeric compound having at least one monomer of formula: or of formula: or of formula: wherein independently for each of said at least one monomer of formula I, II or III: Bx is a heterocyclic base moiety; T3 and T4 are each, independently, an internucleoside linking group linking the monomer to the oligomeric compound or one of T3 and T4 is an internucleoside linking group linking the monomer to the oligomeric compound and the other of T3 and T4 is H, a hydroxyl protecting group or a linked conjugate group; Z is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, substituted C1-C6 alkyl, substituted C2-C6 alkenyl, substituted C2-C6 alkynyl, acyl, substituted acyl, substituted amide, thiol or substituted thiol; each substituted group is, independently, mono or poly substituted with optionally protected substituent groups independently selected from halogen, oxo, hydroxyl, OJ1, NJ1J2, SJ1, N3, OC(═X)J1, OC(═X)NJ1J2, NJ3C(═X)NJ1J2 and CN, wherein each J1, J2 and J3 is, independently, H or C1-C6 alkyl, and X is O, S or NJ1; wherein said oligomeric compound further comprises at least one monomeric subunit selected from a β-D-2′-deoxyribonucleoside, a β-D-ribonucleoside and a nucleoside having a modified sugar moiety wherein each of said modified sugar moieties is, independently, selected from a modified sugar moiety that is substituted with a substituent group, substituted at the 4′-O with a 4′-S, 4′-amino or C1-C6 aminoalkyl, or bridged to form a bicyclic nucleic acid (BNA); wherein said oligomeric compound comprises from 8 to 40 nucleosides and/or modified nucleosides or mimetics in length. 2. The oligomeric compound of claim 1 wherein each of said modified sugar moieties is, independently, selected from a 2′-F modified sugar moiety, a 2′-OCH3 modified sugar moiety, a 2′-O—(CH2)2—OCH3 modified sugar moiety, a 2′-O—CH2-4′ bicyclic modified sugar moiety or a 4′-S modified sugar moiety. 3. The oligomeric compound of claim 1 wherein each Z is, independently, C1-C6 alkyl or substituted C1-C6 alkyl. 4. The oligomeric compound of claim 3 wherein each Z is methyl. 5. The oligomeric compound of claim 3 wherein each Z is substituted C1-C6 alkyl. 6. The oligomeric compound of claim 5 wherein each of said substituent groups is C1-C6 alkoxy. 7. The oligomeric compound of claim 6 wherein each Z is CH3OCH2—. 8. The oligomeric compound of claim 1 wherein the Z group of each monomer of said formula has the configuration represented by formula: or the formula: or the formula: 9. The oligomeric compound of claim 1 wherein the Z group of each monomer of said formula has the configuration represented by formula: or the formula: or the formula: 10. The oligomeric compound of claim 1 wherein each internucleoside linking group is selected from phosphodiester or phosphorothioate. 11. The oligomeric compound of claim 1 wherein each internucleoside linking group is a phosphorothioate. 12. An oligomeric compound having the formula: [T-L]j-[R-L]1-R-[L-T]r wherein: each T is a monomer of formula I: wherein: Bx is a heterocyclic base moiety; Z is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, substituted C1-C6 alkyl, substituted C2-C6 alkenyl, substituted C2-C6 alkynyl, acyl, substituted acyl, substituted amide, thiol or substituted thiol; each L is an internucleoside linking group; each R is a β-D-2′-deoxyribonucleoside; j is 0 or from 1 to about 3; q is from 8 to about 14; r is 0 or from 1 to about 3; the sum of j and r is greater than 1; the sum of j, q and r is from 7 to 39; and each T and R located at a 5′ or 3′ terminus further comprises an optionally protected 5′ or 3′ hydroxyl group or a 5′ or 3′ linked conjugate group; and wherein each of the substituted groups, is, independently, mono or poly substituted with optionally protected substituent groups independently selected from halogen, oxo, hydroxyl, OJ1, NJ1J2, SJ1, N3, OC(═X)J1, OC(═X)NJ1J2, NJ3C(═X)NJ1J2 and CN, wherein each J1, J2 and J3 is, independently, H or C1-C6 alkyl, and X is O, S or NJ1. 13. The oligomeric compound of claim 12 wherein each Z is, independently, C1-C6 alkyl or substituted C1-C6 alkyl. 14. The oligomeric compound of claim 13 wherein each Z is methyl. 15. The oligomeric compound of claim 13 wherein each Z is substituted C1-C6 alkyl. 16. The oligomeric compound of claim 15 wherein each of said substituent groups is C1-C6 alkoxy. 17. The oligomeric compound of claim 16 wherein each Z is CH3OCH2—. 18. The oligomeric compound of claim 12 wherein the Z group of each monomer of said formula has the configuration represented by formula: or the formula: or the formula: 19. The oligomeric compound of claim 12 wherein the Z group of each monomer of said formula has the configuration represented by formula: or the formula: or the formula: 20. The oligomeric compound of claim 12 wherein each internucleoside linking group is selected from phosphodiester or phosphorothioate. 21. The oligomeric compound of claim 12 wherein each internucleoside linking group is a phosphorothioate. 22. The oligomeric compound of claim 12 wherein j is 0. 23. The oligomeric compound of claim 12 wherein r is 0. 24. The oligomeric compound of claim 12 wherein j and r are each other than 0.
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