2′-C-methyl-ribofuranosyl cytidine prodrugs, pharmaceutical compositions and uses thereof
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.
1. A compound of structural Formula (I):
or a pharmaceutically acceptable salt thereof, wherein:
R 1 is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and
R 2 is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and
R 3 is selected from) —N═C(R 10 )(R 11 ) and —NHR 12 ;
R 4 and R 7 are independently selected from hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, arylalkyl, substituted arylalkyl, oxycarbonyl, and substituted oxycarbonyl;
R 5 and R 8 are independently selected from hydrogen, alkyl, substituted alkyl, arylalkyl, substituted arylalkyl, cycloalkyl, and substituted cycloalkyl;
R 6 and R 9 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 R 5 and R 6 together with the nitrogen atom to which they are bonded form a cycloheteroalkyl or substituted cycloheteroalkyl ring;
or R 8 and R 9 together with the nitrogen atom to which they are bonded form a cycloheteroalkyl or substituted cycloheteroalkyl ring;
R 10 and R 11 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;
R 12 is selected from acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and a moiety of structural Formula (II):
X is selected from O and CH 2 ;
q is selected from 1 and 2;
each R 13 and R 14 are independently selected from hydrogen, C 1-4 alkyl, phenyl, and substituted phenyl; or R 13 and R 14 together with the carbon atom to which they are both bonded form a C 3-7 cycloalkyl ring;
R 15 is selected from hydrogen, C 1-4 alkyl, and —CO 2 R 17 ;
W is selected from O and NR 18 ;
R 17 is selected from hydrogen, C 1-4 alkyl, phenyl, and substituted phenyl;
R 18 is selected from hydrogen and C 1-4 alkyl;
R 16 is selected from C 1-4 alkyl, —C(O)R 19 , —C(O)OR 20 ,
R 19 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;
R 20 is selected from C 1-6 alkyl, C 3-7 cycloalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, and substituted heteroaryl;
R 21 and R 22 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 R 21 and R 22 together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, or substituted cycloheteroalkyl ring;
R 23 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;
R 24 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
R 25 is selected from hydrogen and C 1-4 alkyl; or R 24 and R 25 together with the carbon to which they are bonded form a cycloalkyl or cycloheteroalkyl ring;
wherein “substituted” is a group, wherein one or more hydrogen atoms are independently replaced with halogen, —OH, —CN, —CF 3 , ═O, —NO 2 , C 1-3 alkoxy, C 1-3 alkyl, —COOR 64 wherein R 64 is selected from hydrogen and C 1-3 alkyl, and —NR 65 2 wherein each R 65 is independently selected from hydrogen and C 1-3 alkyl;
with the provisos that:
R 3 is not phenylcarbonylamino; and
when R 3 is —NHR 12 wherein R 12 is a moiety of structural Formula (II), X is CH 2 , and W is O; then R 16 is not C 1-4 alkyl.
2. The compound of claim 1 , wherein R 1 is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, and substituted oxycarbonyl.
3. The compound of claim 1 , wherein R 2 is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, and substituted oxycarbonyl.
4. The compound of claim 1 , wherein R 3 is —N═C(R 10 )(R 11 ), wherein R 10 and R 11 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 R 3 is —NHR 12 , and R 12 is selected from acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and a moiety of structural Formula (II).
6. The compound of claim 1 , wherein R 4 and R 7 are independently selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, and substituted oxycarbonyl.
7. The compound of claim 1 , wherein R 5 and R 8 are independently selected from hydrogen, alkyl, substituted alkyl, arylalkyl, substituted arylalkyl, cycloalkyl, and substituted cycloalkyl.
8. The compound of claim 1 , wherein R 6 and R 9 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 R 5 and R 6 , or R 8 and R 9 , together with the atoms to which they are bonded form a cycloheteroalkyl or substituted cycloheteroalkyl ring.
10. The compound of claim 1 , wherein R 1 is hydrogen; R 2 is hydrogen; R 3 is —N═C(R 10 )(R 11 ), wherein R 10 and R 11 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:
R 1 is
and R 2 is hydrogen; or
R 1 is hydrogen and R 2 is
and
R 3 is —N═C(R 10 (R 11 ), wherein:
R 10 and R 11 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 R 4 and R 5 is hydrogen;
R 6 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 5 and R 6 together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;
each of R 7 and R 8 is hydrogen; and
R 9 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 8 and R 9 together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine or piperidine ring.
13. The compound of claim 1 , wherein:
R 1 is hydrogen;
R 2 is hydrogen; and
R 3 is —NHR 12 , wherein R 12 is selected from acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and a moiety of structural Formula (II).
14. The compound of claim 13 , wherein
R 12 is —C(O)OR 26 ;
R 26 is selected from C 1-6 alkyl, C 3-7 cycloalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, substituted heteroaryl, and CH 2 R 27 ; wherein
R 27 is selected from trifluoromethyl, cyano, C 1-4 alkanesulfonyl, benzenesulfonyl, and substituted benzenesulfonyl.
15. The compound of claim 1 , wherein:
R 1 is
and R 2 is hydrogen; or
R 1 is hydrogen and R 2 is
and
R 3 is —NHR 12 ; wherein
R 12 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 R 4 and R 5 is hydrogen;
R 6 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 5 and R 6 together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;
each of R 7 and R 8 is hydrogen; and
R 9 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 8 and R 9 together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring.
17. The compound of claim 1 , wherein:
R 1 is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and
R 2 is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and
R 3 is —NHR 12 ; wherein R 12 is
wherein:
R 21 and R 22 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 R 21 and R 22 together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, or substituted cycloheteroalkyl ring; and
R 23 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:
R 21 and R 22 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 R 21 and R 22 together with the carbon atom to which they are bonded form a C 3-6 cycloalkyl ring; and
R 23 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:
R 21 is selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenethyl, and 3-pyridyl;
R 22 is hydrogen; and
R 23 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 R 1 and R 2 is hydrogen.
21. The compound of claim 20 , wherein R 21 is selected from hydrogen, methyl, propyl, isopropyl, and tert-butyl.
22. The compound of claim 19 , wherein:
R 1 is
and R 2 is hydrogen; or
R 1 is hydrogen and R 2 is
23. The compound of claim 22 , wherein:
each of R 4 and R 5 is hydrogen;
R 6 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 5 and R 6 together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;
each of R 7 and R 8 is hydrogen; and
R 9 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 8 and R 9 together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring.
24. The compound of claim 22 , wherein R 21 is selected from hydrogen, methyl, propyl, isopropyl, and tert-butyl.
25. The compound of claim 1 , wherein:
R 1 is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and
R 2 is selected from hydrogen, acyl, substituted acyl, acyloxyalkylcarbonyl, substituted acyloxyalkylcarbonyl, oxycarbonyl, substituted oxycarbonyl, and
R 3 is —NHR 12 , wherein R 12 is a moiety of structural Formula (II):
X is selected from O and CH 2 ;
q is selected from 1 and 2;
each R 13 and R 14 is independently selected from hydrogen, C 1-4 alkyl, phenyl, and substituted phenyl; or R 13 and R 14 together with the carbon atom to which they are both bonded form a C 3-7 cycloalkyl ring;
R 15 is selected from hydrogen, C 1-4 alkyl, and —CO 2 R 17 ;
W is selected from O and NR 18 ;
R 17 is selected from hydrogen, C 1-4 alkyl, phenyl, and substituted phenyl;
R 18 is selected from hydrogen and C 1-4 alkyl; and
R 16 is selected from C 1-4 alkyl, —C(O)R 19 , —C(O)OR 20 ,
wherein:
R 19 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;
R 20 is selected from C 1-6 alkyl, C 3-7 cycloalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, and substituted heteroaryl;
R 21 and R 22 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 R 21 and R 22 together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, or substituted cycloheteroalkyl ring;
R 23 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;
R 24 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
R 25 is selected from hydrogen and C 1-4 alkyl; or R 24 and R 25 together with the carbon to which they are bonded form a cycloalkyl or cycloheteroalkyl ring;
with the proviso that:
when X is CH 2 and W is O; then R 16 is not C 1-4 alkyl.
26. The compound of claim 25 , wherein R 21 is selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenethyl, and 3-pyridyl; and R 22 is hydrogen.
27. The compound of claim 25 , wherein R 23 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 R 24 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl.
29. The compound of claim 28 , wherein R 25 is hydrogen.
30. The compound of claim 25 , wherein:
X is O;
q is 1;
each of R 13 and R 14 is hydrogen;
R 15 is hydrogen;
W is NR 18 , wherein R 18 is hydrogen; and
R 16 is
31. The compound of claim 30 , wherein:
R 24 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; and
R 25 is hydrogen.
32. The compound of claim 31 , wherein each of R 1 and R 2 is hydrogen.
33. The compound of claim 31 , wherein:
R 1 is
and R 2 is hydrogen; or
R 1 is hydrogen and R 2 is
34. The compound of claim 33 , wherein:
each of R 4 and R 5 is hydrogen;
R 6 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 5 and R 6 together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;
each of R 7 and R 8 is hydrogen; and
R 9 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NY)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 8 and R 9 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 R 13 and R 14 is hydrogen;
R 15 is selected from hydrogen and —CO 2 H;
W is selected from O and NR 18 wherein R 18 is selected from hydrogen and methyl; and
R 16 is selected from
methyl, —C(O)R 19 , and —C(O)OR 20 .
36. The compound of claim 35 , wherein:
R 1 is hydrogen;
R 2 is hydrogen;
R 24 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; and
R 25 is hydrogen.
37. The compound of claim 35 , wherein each of R 1 and R 2 is hydrogen.
38. The compound of claim 35 , wherein:
R 1 is
and R 2 is hydrogen; or
R 1 is hydrogen and R 2 is
39. The compound of claim 38 , wherein:
each of R 4 and R 5 is hydrogen;
R 6 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 5 and R 6 together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;
each of R 7 and R 8 is hydrogen; and
R 9 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 8 and R 9 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 CH 2 ;
q is 1;
each of R 13 and R 14 is hydrogen;
R 15 is hydrogen;
W is selected from O and NR 18 wherein R 18 is hydrogen; and
R 16 is selected from —C(O)R 19 and —C(O)OR 20 .
41. The compound of claim 40 , wherein R 19 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 R 1 and R 2 is hydrogen.
43. The compound of claim 40 , wherein:
R 1 is
and R 2 is hydrogen; or
R 1 is hydrogen and R 2 is.
44. The compound of claim 43 , wherein:
each of R 4 and R 5 is hydrogen;
R 6 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 5 and R 6 together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;
each of R 7 and R 8 is hydrogen; and
R 9 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 8 and R 9 together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring.
45. The compound of claim 40 , wherein R 20 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 R 1 and R 2 is hydrogen.
47. The compound of claim 25 , wherein:
X is O;
q is 1;
each of R 13 and R 14 is hydrogen;
R 15 is hydrogen;
W is NR 18 , wherein R 18 is selected from hydrogen and methyl; and
R 16 is
wherein R 21 is selected from hydrogen, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, and phenyl;
R 22 K is hydrogen; and
R 23 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 R 1 and R 2 is hydrogen.
49. The compound of claim 47 , wherein:
R 1 is
and R 2 is hydrogen; or
R 1 is hydrogen and R 2 is
50. The compound of claim 49 , wherein:
each of R 4 and R 5 is hydrogen;
R 6 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 5 and R 6 together with the nitrogen atom to which they are bonded form an azetidine, pyrrolidine, or piperidine ring;
each of R 7 and R 8 is hydrogen; and
R 9 is selected from hydrogen, methyl, isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, —CH 2 OH, —CH(OH)CH 3 , —CH 2 CO 2 H, —CH 2 CH 2 CO 2 H, —CH 2 CONH 2 , —CH 2 CH 2 CONH 2 , —CH 2 CH 2 SCH 3 , —CH 2 SH, —CH 2 (CH 2 ) 3 NH 2 , —CH 2 CH 2 CH 2 NHC(NH)NH 2 , phenyl, benzyl, 4-hydroxybenzyl, 4-imidazolylmethyl, and 3-indolylmethyl; or R 8 and R 9 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-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-Pentyloxycarbonylamino-2-oxo-1H-pyrimidin-1-yl)-3-O-(pentyloxycarbonyl)-5-O-(pentyloxycarbonyl)-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)-ethoxycarbonylam ino]-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-((Acetoxymethypoxycarbonylamino)-ethoxycarbonylamino]-2-oxo-1H-pyrimidin-1-yl}-2-C-methyl-ribofuranose;
β-1-{[4-(2-((1-Isobutanoyloxyethypoxycarbonylamino)-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-Pivaloylloxy-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; and
a pharmaceutically acceptable salt of any of the foregoing.
52. A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable vehicle.
53. A method of treating a patient infected with hepatitis C comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of claim 1 .
54. A method of treating a patient infected with hepatitis C comprising administering to a patient in need of such treatment a therapeutically effective amount of a pharmaceutical composition of claim 52 .