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US 8,022,193 B2Granted
6-modified bicyclic nucleic acid analogs
AssigneeIsis Pharmaceuticals, Inc.
InventorsPunit P. Seth, Eric E. Swayze
Life of this patent
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Abstract
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.
Claims19
An oligomeric compound comprising at least one monomer having Formula IX:
- wherein independently for each of said monomers having Formula IX:
- 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 or substituted C1-C6 alkyl;
- each substituted group is, independently, mono or poly substituted with optionally protected substituent groups independently selected from fluoro, OJ1, NJ1J2, SJ1 and CN, wherein each J1 and J2 is, independently, H, C1-C6 alkyl or a protecting group;
- and
- wherein said oligomeric compound comprises from about 8 to about 40 nucleosides and/or modified nucleosides or mimetics in length.
4 more elements
An oligomeric compound having the formula:
- G-[T-L]j-[R-L]q-R-[L-T]r-E III
- wherein:
- each R is a β-D-2′-deoxyribonucleoside;
- each L is, independently, a phosphodiester or phosphorothioate internucleoside linking group;
- G and E are each, independently, H, a hydroxyl protecting group or a linked conjugate group;
- each T is a monomer of the Formula VIII:
- wherein independently for each monomer having Formula VIII:
- Bx is a heterocyclic base moiety;
- Z is C1-C6 alkyl or substituted C1-C6 alkyl;
- each substituted group is, independently, mono or poly substituted with optionally protected substituent groups independently selected from fluoro, OJ1, NJ1J2, SJ1 and CN, wherein each J1 and J2 is, independently, H, C1-C6 alkyl or a protecting group;
- q is from 8 to about 14;
- j is 0 or from 1 to 5;
- r is 0 or from 1 to 5;
- and
- the sum of j and r is at least 1.
12 more elements
Dependencies are inferred from the claim text.