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US 5,847,106 AGranted
Monomeric and dimeric nucleosides with silyl-containing diamino phosphorous linkages
AssigneeIsis Pharmaceuticals, Inc.
InventorsVasulinga Ravikumar, Dennis Mulvey, Douglas L. Cole, Phillip Dan Cook
Life of this patent
Estimating the term…
Abstract
Synthetic processes are provided wherein substituted silylalkyl phosphoramidites serve as coupling reagents for preparing phosphate, phosphorothioate, and other phosphorous-containing covalent linkages. Also provided are synthetic intermediates useful in such processes. h processes.
Claims21
A compound having formula II:
- ##STR9## wherein:
- Q is O, S, CH.sub.2, CHF or CF.sub.2 ;
- B.sub.X is a nucleosidic base;
- X is H, OH, alkyl, substituted alkyl, alkaryl or aralkyl, F, Cl, Br, CN, CF.sub.3, OCF.sub.3, OCN, O-alkyl, S-alkyl, N-alkyl, O-alkenyl, S-alkenyl, N-alkenyl, SOCH.sub.3, SO.sub.2 CH.sub.3, ONO.sub.2, NO.sub.2, N.sub.3, NH.sub.2, heterocycloalkyl, heterocycloalkaryl, aminoalkylamino, or substituted silyl;
- R.sub.HP is a hydroxyl protecting group;
- each R.sub.N is, independently, alkyl having 1 to about 10 carbon atoms;
- each R.sub.S is, independently, alkyl having 1 to about 10 carbon atoms or aryl having 6 to about 10 carbon atoms;
- and
- x is 1 to about 7.
6 more elements
A compound having formula IV:
- ##STR10## wherein:
- each Q is, independently, O, S, CH.sub.2, CHF or CF.sub.2 ;
- each B.sub.x is, independently, a nucleosidic base;
- each X is, independently, H, OH, alkyl, substituted alkyl, alkaryl or aralkyl, F, Cl, Br, CN, CF.sub.3, OCF.sub.3, OCN, O-alkyl, S-alkyl, N-alkyl, O-alkenyl, S-alkenyl, N-alkenyl, SOCH.sub.3, SO.sub.2 CH.sub.3, ONO.sub.2, NO.sub.2, N.sub.3, NH.sub.2, heterocycloalkyl, heterocycloalkaryl, aminoalkylamino, substituted silyl;
- R.sub.HP is a hydroxyl protecting group;
- each R.sub.S is, independently, alkyl having 1 to about 10 carbon atoms or aryl having 6 to about 10 carbon atoms;
- (P) is H, a hydroxyl protecting group or a solid support;
- and
- x is 1 to about 7.
6 more elements
A compound having formula V:
- ##STR11## wherein:
- each Q is, independently, O, S, CH.sub.2, CHF or CF.sub.2 ;
- each B.sub.X is, independently, a nucleosidic base;
- each X is, independently, H, OH, alkyl, substituted alkyl, alkaryl or aralkyl, F, Cl, Br, CN, CF.sub.3, OCF.sub.3, OCN, O-alkyl, S-alkyl, N-alkyl, O-alkenyl, S-alkenyl, N-alkenyl, SOCH.sub.3, SO.sub.2 CH.sub.3 ONO.sub.2, NO.sub.2, N.sub.3, NH.sub.2, heterocycloalkyl, heterocycloalkaryl, aminoalkylamino, substituted silyl;
- R.sub.HP is a hydroxyl protecting group;
- each R.sub.S is, independently, alkyl having 1 to about 10 carbon atoms or aryl having 6 to about 10 carbon atoms;
- (P) is H, a hydroxyl protecting group or a solid support;
- Z is O or S;
- and
- x is 1 to about 7.
7 more elements
Dependencies are inferred from the claim text.