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US 8,030,467 B2Granted
5′-modified bicyclic nucleic acid analogs
AssigneeIsis Pharmaceuticals, Inc.
InventorsPunit P. Seth, Eric E. Swayze, Balkrishen Bhat
Life of this patent
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Abstract
The present invention provides 5′-modified bicyclic nucleoside analogs and oligomeric compounds comprising at least one of these nucleoside analogs. In preferred embodiments the nucleoside analogs have either (R) or (S)-chirality at the 5′-carbon. These bicyclic nucleoside analogs are useful for enhancing properties of oligomeric compounds including for example enhanced nuclease resistance.
Claims26
An oligomeric compound having Formula II:
- G-[T-L]j-[R-L]q-R-[L-T]r-E II
- wherein:
- each R is a β-D-2′-deoxyribonucleoside;
- each L is, independently, a phosphodiester or phosphorothioate internucleoside linking group;
- each T is a monomer of Formula III:
- wherein independently for each monomer having Formula III:
- Bx is a heterocyclic base moiety;
- Z is C1-C6 alkyl or C1-C6 alkyl substituted with C2-C6 alkenyl, C1-C6 alkoxy or one or more fluoro atoms;
- G and E are each, independently, H, a hydroxyl protecting group or a linked conjugate group;
- q is from 7 to about 15;
- j is 0 or from 1 to about 5;
- r is 0 or from 1 to about 5;
- and
- the sum of j and r is at least 1.
11 more elements
An oligomeric compound comprising at least one monomer having Formula IV:
- wherein independently for each monomer having Formula IV:
- Bx is a heterocyclic base moiety;
- one of T3 and T4 is an internucleoside linking group attaching the monomer having Formula IV to the oligomeric compound and the other of T3 and T4 is H, a hydroxyl protecting group, a linked conjugate group or an internucleoside linking group attaching the monomer having Formula IV to the oligomeric compound;
- Z is C1-C6 alkyl or C1-C6 alkyl substituted with C2-C6 alkenyl, C1-C6 alkoxy or one or more fluoro atoms;
- said oligomeric compound comprising at least one monomeric subunit that is other than a monomer having formula IV, selected from a β-D-ribonucleoside, a β-D-2′-deoxyribonucleoside and a modified nucleoside wherein said modified nucleoside comprises at least a sugar substituent group, a 4′-S group or a bicyclic modified sugar;
- and
- wherein said oligomeric compound comprises from 8 to 40 nucleosides and/or modified nucleosides or mimetics in length.
4 more elements
Dependencies are inferred from the claim text.