2'-C-Methyl-Ribofuranosyl Cytidine Prodrugs, Pharmaceutical Compositions and Uses Thereof

• US 20070270374A1
• Filed: 05/22/2007
• Published: 11/22/2007
• Est. Priority Date: 05/22/2006
• Status: Active Grant

• Current Assignee: XenoPort, Inc. (Arbor Pharmaceuticals LLC)
• Original Assignee: XenoPort, Inc. (Arbor Pharmaceuticals LLC)
• Inventors: Gallop, Mark A.
• Granted Patent: US 8,058,260 B2
• Time in Patent Office: Days
• US Class Current: 514/49
• CPC Class Codes: A61P 31/14 for RNA viruses
• CPC Class Codes: C07H 19/06 Pyrimidine radicals

Abstract

The present disclosure provides 2′-C-methyl-ribofuranosyl cytidine prodrugs, methods of making 2′-C-methyl-ribofuranosyl cytidine prodrugs, pharmaceutical compositions of 2′-C-methyl-ribofuranosyl cytidine prodrugs, and methods of using 2′-C-methyl-ribofuranosyl cytidine prodrugs and pharmaceutical compositions thereof to treat viral diseases such as hepatitis C.

Claims

1. A compound of structural Formula (I):

a pharmaceutically acceptable salt of any of the foregoing, or a pharmaceutically acceptable solvate of any of the foregoing, wherein;

R¹ is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and

R² is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and

R³ is selected from —

N═

C(R¹⁰)(R¹¹) and —

NHR¹²;

R⁴ and R⁷ are independently selected from hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, arylalkyl, substituted arylalkyl, oxycarbonyl, and substituted oxycarbonyl;

R⁵ and R⁸ are independently selected from hydrogen, alkyl, substituted alkyl, arylalkyl, substituted arylalkyl, cycloalkyl, and substituted cycloalkyl;

R⁶ and R⁹ are independently selected from hydrogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, acyl, substituted acyl, alkoxycarbonyl, substituted alkoxycarbonyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, carbamoyl, substituted carbamoyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl;

or R⁵ and R⁶ together with the nitrogen atom to which they are bonded form a cycloheteroalkyl or substituted cycloheteroalkyl ring;

or R⁸ and R⁹ together with the nitrogen atom to which they are bonded form a cycloheteroalkyl or substituted cycloheteroalkyl ring;

R¹⁰ and R¹¹ are independently selected from hydrogen, acyl, substituted acyl, alkyl, substituted alkyl, alkoxy, substituted alkoxy, alkylamino, substituted alkylamino, amido, substituted amido, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, dialkylamino, substituted dialkylamino, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl;

R¹² is selected from acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and a moiety of structural Formula (II);

X is selected from O and CH₂;

q is selected from 1 and 2;

each R¹³ and R¹⁴ are independently selected from hydrogen, C_1-4 alkyl, phenyl, and substituted phenyl;

or R¹³ and R¹⁴ together with the carbon atom to which they are both bonded form a C_3-7 cycloalkyl ring;

R¹⁵ is selected from hydrogen, C_1-4 alkyl, and —

CO₂R¹⁷;

W is selected from O and NR¹⁸;

R¹⁷ is selected from hydrogen, C_1-4 alkyl, phenyl, and substituted phenyl;

R¹⁸ is selected from hydrogen and C_1-4 alkyl;

R¹⁶ is selected from C_1-4alkyl, —

C(O)R¹⁹, —

C(O)OR²⁰,

R¹⁹ is selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl;

R²⁰ is selected from C_1-6 alkyl, C_3-7 cycloalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, and substituted heteroaryl;

R²¹ and R²² are independently selected from hydrogen, alkyl, substituted alkyl, alkoxycarbonyl, substituted alkoxycarbonyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, carbamoyl, cycloalkyl, substituted cycloalkyl, cycloalkoxycarbonyl, substituted cycloalkoxycarbonyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl;

or R²¹ and R²² together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, or substituted cycloheteroalkyl ring;

R²³ is selected from acyl, substituted acyl, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl;

R²⁴ is selected from hydrogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, acyl, substituted acyl, alkoxycarbonyl, substituted alkoxycarbonyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, carbamoyl, substituted carbamoyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl; and

R²⁵ is selected from hydrogen and C_1-4 alkyl;

or R²⁴ and R²⁵ together with the carbon to which they are bonded form a cycloalkyl or cycloheteroalkyl ring;

with the provisos that;

R³ is not phenylcarbonylamino;

when R³ is —

N═

C(R¹⁰)(R¹¹), and each of R¹, R², and R¹¹ is hydrogen;

then R¹² is not dimethylamino;

or

when R³ is —

NHR¹² wherein R¹² is a moiety of structural Formula (II), X is CH₂, and W is O;

then R¹⁶ is not C_1-4 alkyl.

2. The compound of claim 1, wherein R¹ is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, and substituted oxycarbonyl.

3. The compound of claim 1, wherein R² is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, and substituted oxycarbonyl.

4. The compound of claim 1, wherein R³ is —

N═

C(R¹⁰)(R¹¹), wherein R¹⁰ and R¹¹ are independently selected from hydrogen, alkoxy, substituted alkoxy, alkyl, substituted alkyl, alkylamino, substituted alkylamino, amido, substituted amido, aryl, substituted aryl, arylalkyl, substituted arylalkyl, dialkylamino, substituted dialkylamino, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl.

5. The compound of claim 1, wherein R³ is —

NHR¹², and R¹² is selected from acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and a moiety of structural Formula (II).

6. The compound of claim 1, wherein R⁴ and R⁷ are independently selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, and substituted oxycarbonyl.

7. The compound of claim 1, wherein R⁵ and R⁸ are independently selected from hydrogen, alkyl, substituted alkyl, arylalkyl, substituted arylalkyl, cycloalkyl, and substituted cycloalkyl.

8. The compound of claim 1, wherein R⁶ and R⁹ are independently selected from hydrogen, alkanyl, substituted alkanyl, aryl, substituted aryl, arylalkanyl, substituted arylalkanyl, cycloalkanyl, heteroarylalkyl, and substituted heteroarylalkanyl.

9. The compound of claim 1, wherein R⁵ and R⁶, or R⁸ and R⁹, together with the atoms to which they are bonded form a cycloheteroalkyl or substituted cycloheteroalkyl ring.

10. The compound of claim 1, wherein R¹ is hydrogen;

R² is hydrogen; and

R³ is —

N═

C(R¹⁰)(R¹¹), wherein R¹⁰ and R¹¹ are independently selected from hydrogen, alkoxy, substituted alkoxy, alkyl, substituted alkyl, alkylamino, substituted alkylamino, amido, substituted amido, aryl, substituted aryl, arylalkyl, substituted arylalkyl, dialkylamino, substituted dialkylamino, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl.

11. The compound of claim 1, wherein:

and R² is hydrogen;

or R¹ is hydrogen and

R³ is —

N═

C(R¹⁰)(R¹¹), wherein;

R¹⁰ and R¹¹ are independently selected from hydrogen, alkoxy, substituted alkoxy, alkyl, substituted alkyl, alkylamino, substituted alkylamino, amido, substituted amido, aryl, substituted aryl, arylalkyl, substituted arylalkyl, dialkylamino, substituted dialkylamino, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl.

12. The compound of claim 11, wherein:

each of R⁴ and R⁵ is hydrogen;

R⁶ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁵ and R⁶ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;

each of R⁷ and R⁸ is hydrogen; and

R⁹ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁸ and R⁹ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine or piperidine ring.

13. The compound of claim 1, wherein:

R¹ is hydrogen;

R² is hydrogen; and

R³ is —

NHR², wherein R¹² is selected from acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and a moiety of structural Formula (II).

14. The compound of claim 13, wherein

R¹² is —

C(O)OR²⁶;

R²⁶ is selected from C_1-6 alkyl, C_3-7 cycloalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, substituted heteroaryl, and CH₂R²⁷;

wherein

R²⁷ is selected from trifluoromethyl, cyano, C_1-4 alkanesulfonyl, benzenesulfonyl, and substituted benzenesulfonyl.

15. The compound of claim 1, wherein:

R¹ is

and R² is hydrogen;

or

R¹ is hydrogen and R²is

R³is —

NHR¹²;

wherein

R¹² is selected from acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and a moiety of structural Formula (II).

16. The compound of claim 15, wherein:

each of R⁴ and R⁵ is hydrogen;

R⁶ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁵ and R⁶ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;

each of R⁷ and R⁸ is hydrogen; and

R⁹ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁸ and R⁹ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring.

17. The compound of claim 1, wherein:

R¹ is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and

R² is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and

R³ is —

NHR¹²;

wherein R¹² is

R²¹ and R²² are independently selected from hydrogen, alkyl, substituted alkyl, alkoxycarbonyl, substituted alkoxycarbonyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, carbamoyl, cycloalkyl, substituted cycloalkyl, cycloalkoxycarbonyl, substituted cycloalkoxycarbonyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl;

or R²¹ and R²² together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, or substituted cycloheteroalkyl ring; and

R²³ is selected from acyl, substituted acyl, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl.

18. The compound of claim 17, wherein:

R²¹ and R²² are independently selected from hydrogen, C_1-4 alkyl, substituted C_1-4 alkyl, C_1-4 alkoxycarbonyl, C_3-6 cycloalkyl, C_3-6 cycloalkoxycarbonyl, phenyl, substituted phenyl, C_7-9 phenylalkyl, and pyridyl;

or R²¹ and R²² together with the carbon atom to which they are bonded form a C_3-6 cycloalkyl ring; and

R²³ is selected from C_1-6 alkyl, substituted C_1-6 alkyl, C_3-6 cycloalkyl, phenyl, substituted phenyl, C_7-9 phenylalkyl, pyridyl, and substituted pyridyl.

19. The compound of claim 17, wherein:

R²¹ is selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenethyl, and 3-pyridyl;

R²² is hydrogen; and

R²³ is selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pent-1-yl, pent-2-yl, pent-3-yl, 2-methylbut-1-yl, 3-methylbut-1-yl, 1,1-dimethoxyethyl, 1,1-diethoxyethyl, phenyl, 2-methylphenyl, 2,6-dimethylphenyl, 2-methoxyphenyl, 4-methoxyphenyl, 2,6-dimethoxyphenyl, benzyl, phenethyl, styryl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and 3-pyridyl.

20. The compound of claim 19, wherein each of R¹ and R² is hydrogen.

21. The compound of claim 20, wherein R²¹ is selected from hydrogen, methyl, propyl, isopropyl, and tert-butyl.

22. The compound of claim 19, wherein:

R¹ is

and R² is hydrogen;

or

R¹ is hydrogen and R² is

23. The compound of claim 22, wherein:

each of R⁴ and R⁵ is hydrogen;

R⁶ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁵ and R⁶ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;

each of R⁷ and R⁸ is hydrogen; and

R⁹ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁸ and R⁹ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring.

24. The compound of claim 22, wherein R²¹ is selected from hydrogen, methyl, propyl, isopropyl, and tert-butyl.

25. The compound of claim 1, wherein:

R¹ is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and

R² is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and

R³ is —

NHR¹², wherein R¹² is a moiety of structural Formula (II);

X is selected from O and CH₂;

q is selected from 1 and 2;

each R¹³ and R¹⁴ is independently selected from hydrogen, C_1-4 alkyl, phenyl, and substituted phenyl;

or R¹³ and R¹⁴ together with the carbon atom to which they are both bonded form a C_3-7 cycloalkyl ring;

R¹⁵ is selected from hydrogen, C_1-4 alkyl, and —

CO₂R¹⁷;

W is selected from O and NR¹⁸;

R¹⁷ is selected from hydrogen, C_1-4 alkyl, phenyl, and substituted phenyl;

R¹⁸ is selected from hydrogen and C_1-4 alkyl; and

R¹⁶ is selected from C_1-4alkyl, —

C(O)R¹⁹, —

C(O)OR²⁰,

R¹⁹ is selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl;

R²⁰ is selected from C_1-6 alkyl, C_3-7 cycloalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, and substituted heteroaryl;

R²¹ and R²² are independently selected from hydrogen, alkyl, substituted alkyl, alkoxycarbonyl, substituted alkoxycarbonyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, carbamoyl, cycloalkyl, substituted cycloalkyl, cycloalkoxycarbonyl, substituted cycloalkoxycarbonyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl;

or R²¹ and R²² together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, or substituted cycloheteroalkyl ring;

R²³ is selected from acyl, substituted acyl, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl;

R²⁴ is selected from hydrogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, acyl, substituted acyl, alkoxycarbonyl, substituted alkoxycarbonyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, carbamoyl, substituted carbamoyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl; and

R²⁵ is selected from hydrogen and C_1-4 alkyl;

or R²⁴ and R²⁵ together with the carbon to which they are bonded form a cycloalkyl or cycloheteroalkyl ring;

with the proviso that;

when X is CH₂ and W is O;

then R¹⁶ is not C_1-4 alkyl.

26. The compound of claim 25, wherein R²¹ is selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenethyl, and 3-pyridyl;

and R²² is hydrogen.

27. The compound of claim 25, wherein R²³ is selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pent-1-yl, pent-2-yl, pent-3-yl, 2-methylbut-1-yl, 3-methylbut-1-yl, 1,1-dimethoxyethyl, 1,1-diethoxyethyl, phenyl, 2-methylphenyl, 2,6-dimethylphenyl, 2-methoxyphenyl, 4-methoxyphenyl, 2,6-dimethoxyphenyl, benzyl, phenethyl, styryl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and 3-pyridyl.

28. The compound of claim 25, wherein R²⁴ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl.

29. The compound of claim 28, wherein R²⁵ is hydrogen.

30. The compound of claim 25, wherein:

X is O;

q is 1;

each of R¹³ and R¹⁴ is hydrogen;

R¹⁵ is hydrogen;

W is NR¹⁸, wherein R¹⁸ is hydrogen; and

R¹⁶ is

31. The compound of claim 30, wherein:

R²⁴ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; and

R²⁵ is hydrogen.

32. The compound of claim 31, wherein each of R¹ and R² is hydrogen.

33. The compound of claim 31, wherein:

R¹ is

and R² is hydrogen;

or

R¹ is hydrogen and

R² is

34. The compound of claim 33, wherein:

each of R⁴ and R⁵ is hydrogen;

R⁶ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁵ and R⁶ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;

each of R⁷ and R⁸ is hydrogen; and

R⁹ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁸ and R⁹ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine or piperidine ring.

35. The compound of claim 25, wherein:

X is O;

q is 1;

each of R¹³ and R¹⁴ is hydrogen;

R¹⁵ is selected from hydrogen and —

CO₂H;

W is selected from O and NR¹⁸ wherein R¹⁸ is selected from hydrogen and methyl; and

R¹⁶ is selected from

methyl, —

C(O)R¹⁹, and —

C(O)OR²⁰.

36. The compound of claim 35, wherein:

R¹ is hydrogen;

R² is hydrogen;

R²⁴ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; and

R²⁵ is hydrogen.

37. The compound of claim 35, wherein each of R¹ and R² is hydrogen.

38. The compound of claim 35, wherein:

R¹ is

and R² is hydrogen;

or

R¹ is hydrogen and

R² is

39. The compound of claim 38, wherein:

each of R⁴ and R⁵ is hydrogen;

R⁶ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁵ and R⁶ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;

each of R⁷ and R⁸ is hydrogen; and

R⁹ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁸ and R⁹ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring.

40. The compound of claim 25, wherein:

X is CH₂;

q is 1;

each of R¹³ and R¹⁴ is hydrogen;

R¹⁵ is hydrogen;

W is selected from O and NR¹⁸ wherein R¹⁸ is hydrogen; and

R¹⁶ is selected from —

C(O)R¹⁹ and —

C(O)OR²⁰.

41. The compound of claim 40, wherein R¹⁹ is selected from C_1-6 alkyl, substituted C_1-6 alkyl, C_3-6 cycloalkyl, phenyl, substituted phenyl, C_7-9 phenylalkyl, pyridyl, and substituted pyridyl.

42. The compound of claim 40, wherein each of R¹ and R² is hydrogen.

43. The compound of claim 40, wherein:

R¹ is

and R² is hydrogen;

or

R¹ is hydrogen and

R² is

44. The compound of claim 43, wherein:

each of R⁴ and R⁵ is hydrogen;

R⁶ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁵ and R⁶ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;

each of R⁷ and R⁸ is hydrogen; and

R⁹ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁵ and R⁹ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring.

45. The compound of claim 40, wherein R²⁰ is selected from C_1-6 alkanyl, C_2-6 alk-1-en-2-yl, 2-C_3-7 cycloalkyl-eth-1-en-2-yl, 2-phenyleth-1-en-2-yl, substituted 2-phenyleth-1-en-2-yl, C_3-7 cycloalkanyl, C_5-7 cycloalk-1-en-1-yl, phenyl, naphthyl, halophenyl, methoxyphenyl, cyanophenyl, carboxyphenyl, C_1-4 alkoxycarbonylphenyl, aminophenyl, halobenzyl, methoxybenzyl, cyanobenzyl, carboxybenzyl, C_1-4 alkoxycarbonylbenzyl, aminobenzyl, furyl, thienyl, pyrrolyl, imidazoyl, oxazolyl, pyridyl, pyrimidyl, pyraziny, and triazinyl.

46. The compound of claim 45, wherein each of R¹ and R² is hydrogen.

47. The compound of claim 25, wherein:

X is O;

q is 1;

each of R¹³ and R¹⁴ is hydrogen;

R¹⁵ is hydrogen;

W is NR¹⁸, wherein R¹⁸ is selected from hydrogen and methyl; and

R¹⁶ is

wherein R²¹ is selected from hydrogen, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, and phenyl;

R²² is hydrogen; and

R²³ is selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pent-1-yl, pent-2-yl, pent-3-yl, 2-methylbut-1-yl, 3-methylbut-1-yl, 1,1-dimethoxyethyl, 1,1-diethoxyethyl, phenyl, 2-methylphenyl, 2,6-dimethylphenyl, 2-methoxyphenyl, 4-methoxyphenyl, 2,6-dimethoxyphenyl, benzyl, phenethyl, styryl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and 3-pyridyl.

48. The compound of claim 47, wherein each of R¹ and R² is hydrogen.

49. The compound of claim 47, wherein:

R¹ is

and R² is hydrogen;

or

R¹ is hydrogen and

R² is

50. The compound of claim 49, wherein:

each of R⁴ and R⁵ is hydrogen;

R⁶ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁵ and R⁶ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;

each of R⁷ and R⁸ is hydrogen; and

R⁹ is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —

CH₂OH, —

CH(OH)CH₃, —

CH₂CO₂H, —

CH₂CH₂CO₂H, —

CH₂CONH₂, —

CH₂CH₂CONH₂, —

CH₂CH₂SCH₃, —

CH₂SH, —

CH₂(CH₂)₃NH₂, —

CH₂CH₂CH₂NHC(NH)NH₂, phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl;

or R⁸ and R⁹ together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring.

51. The compound of claim 1, wherein the compound is selected from:

β

-1-(4-allyloxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-benzyloxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-ethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-ethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-5-O-(tert-butyldimethylsilyl)-2-C-methyl-ribofuranose;

β

-1-(4-ethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-3-O-(N-tert-butyloxycarbonyl-L-valinyl)-5-O-(tert-butyldimethylsilyl)-2-C-methyl-ribofuranose;

β

-1-(4-ethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-3-O-(L-valinyl)-2-C-methyl-ribofuranose;

β

-1-(4-ethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-3-O-(tetrahydropyranyl)-5-O-(tert-butyldimethylsilyl)-2-C-methyl-ribofuranose;

β

-1-(4-ethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-3-O-(tetrahydropyranyl)-2-C-methyl-ribofuranose;

β

-1-(4-ethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-3-O-(tetrahydropyranyl)-5-O-(N-tert-butoxycarbonyl-L-valinyl)-2-C-methyl-ribofuranose;

β

-1-(4-ethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-5-O-(L-valinyl)-2-C-methyl-ribofuranose;

β

-1-(4-allyloxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-5-O-(tert-butyldimethylsilyl)-2-C-methyl-ribofuranose;

β

-1-(4-Pentyloxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-Amino-2-oxo-1H-pyrimidin-1-yl)-5-O-(pentyloxycarbonyl)-2-C-methyl-ribofuranose;

β

-1-(4-Amino-2-oxo-1H-pyrimidin-1-yl)-3-O-(pentyloxycarbonyl)-2-C-methyl-ribofuranose;

β

-1-(4-Pentyloxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-3-O-(pentyloxycarbonyl)-2-C-methyl-ribofuranose;

β

-1-(4-Pentyloxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-5-O-(pentyloxycarbonyl)-2-C-methyl-ribofuranose;

β

-1-(4-Amino-2-oxo-1H-pyrimidin-1-yl)-3-O-(pentyloxycarbonyl)-5-O-(pentyloxycarbonyl)-2-C-methyl-ribofuranose;

β

-1-(4-Pentyloxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-3-O-(pentyloxycarbonyl)-5-O-(pentyloxycarbonyl)-2-C-methyl-ribofuranose;

β

-1-(4-amino-2-oxo-1H-pyrimidin-1-yl)-3,5-O-di-(tert-butyldimethylsilyl)-2-C-methyl-ribofuranose;

β

-1-(4-Phenyloxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-(4-Methoxyphenyl)oxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-(1,1,1-Trifluoroethyl)oxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-(4-Methoxybenzyl)oxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-(Propen-2-yl)oxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-(2-Carboxy-2-methyl)ethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-Pentyloxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-5-O-acetyl-2-C-methyl-ribofuranose;

β

-1-(4-Pentyloxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-3-O-acetyl-2-C-methyl-ribofuranose;

β

-1-(4-Acetoxymethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-(1-Isobutanoyloxyethoxy)carbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-(2,6-Dimethylbenzoyl)oxymethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-(2-Methylbenzoyl)oxymethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-Acetoxymethoxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-5-O-(L-valinyl)-2-C-methyl-ribofuranose;

β

-1-{[4-((2S)-((2S)-Aminopropionylamino)-2-carboxy)ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-((2S)-((2S)-Amino-3,3-dimethylbutyroylamino)-2-carboxy)ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-((2S)-(Aminoacetylamino)-2-carboxy)ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-((2S)-((2S)-Aminophenacetylamino)-2-carboxy)ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-((2S)-(2-Amino-2-methylpropionylamino)-2-carboxy)ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-((2S)-(1-Amino-cyclohexanecarbonylamino)-2-carboxy)ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-(4-(2-Acetoxyethoxy)carbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-(2-Pivaloyloxyethoxy)carbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-(4-(2-Cyclohexanecarboxyethoxy)carbonylamino-2-oxo-1H-pyrimidin-1-yl)-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((2S)-Amino-3-methylbutyroylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((2S)-Amino-3-phenylpropionylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-(Phenyloxycarbonylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(3-(Benzyloxycarbonylamino)-propoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-[4-(2-Dimethylamino-ethoxycarbonylamino)-2-oxo-1H-pyrimidin-1-yl]-2-C-methyl-ribofuranose;

β

-1-[4-(4-Acetoxybutyroylamino)-2-oxo-1H-pyrimidin-1-yl]-2-C-methyl-ribofuranose;

β

-1-[4-(4-Pivaloyloxybutyroylamino)-2-oxo-1H-pyrimidin-1-yl]-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Pivaloyloxy-2,2-dimethylpropyl)oxycarbonylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((Isobutanoyloxymethyl)oxycarbonylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((Acetoxymethyl)oxycarbonylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Isobutanoyloxyethyl)oxycarbonylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Acetoxy-2-methylpropyl)oxycarbonylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Isobutanoyloxy-2-methylpropyl)oxycarbonylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Pivaloyloxy-2-methylpropyl)oxycarbonylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Pivaloyloxyethyl)oxycarbonylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Acetoxyethyl)oxycarbonylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((Acetoxymethyl)oxycarbonylmethylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Isobutanoyloxyethyl)oxycarbonylmethylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Acetoxy-2-methylpropyl)oxycarbonylmethylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Isobutanoyloxy-2-methylpropyl)oxycarbonylmethylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Pivaloyloxy-2-methylpropyl)oxycarbonylmethylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Pivaloyloxyethyl)oxycarbonylmethylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-Acetoxyethyl)oxycarbonylmethylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-(2,6-Dimethylbenzoyl)oxymethyl)oxycarbonylmethylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-(2,6-Dimethylbenzoyl)oxy-2-methylpropyl)oxycarbonylmethylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

β

-1-{[4-(2-((1-(2-Methylbenzoyl)oxy-2-methylpropyl)oxycarbonylmethylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;

a pharmaceutically acceptable salt of any of the foregoing, and a pharmaceutically acceptable solvate of any of the foregoing.

52. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable vehicle.

53. A method of treating a patient infected with a Flaviviridae virus comprising administering to a patient in need of such treatment a therapeutically effective amount of the compound of claim 1.

54. The method of claim 53, wherein the Flaviviridae virus is hepatitis C.

55. A method of treating a patient infected with a Flaviviridae virus comprising administering to a patient in need of such treatment a therapeutically effective amount of the pharmaceutical composition of claim 52.

56. The method of claim 55, wherein the Flaviviridae virus is hepatitis C.

57. The method of claim 53 further comprising administering to the patient a therapeutically effective amount of a second anti-viral agent, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvante of any of the foregoing, or a pharmaceutical composition comprising the second anti-viral agent, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate of any of the foregoing, and a pharmaceutically acceptable vehicle.

58. The method of claim 55 further comprising administering to the patient a therapeutically effective amount of a second anti-viral agent, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate of any of the foregoing, or a pharmaceutical composition comprising the second anti-viral agent, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate of any of the foregoing, and a pharmaceutically acceptable vehicle.

59. The method according to any one of claims 57 and 58, wherein the second antiviral agent is selected from an interferon, ribavirin, interleukin, an NS3 protease inhibitor, cysteine protease inhibitor, thiazolidine derivative, thiazolidine, benzanilide, phenanthrenequinone, a helicase inhibitor, a polymerase inhibitor, a nucleotide analogue, gliotoxin, cerulenin, antisense phosphorothioate oligodeoxynucleotides, inhibitor of IRES-dependent translation, and a ribozyme.

60. The method according to any one of claims 57 and 58, wherein the second antiviral agent is an interferon.