Antiviral phosphonate compounds and methods therefor
First Claim
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1. A pharmaceutical composition comprising:
- a nucleotide analog having a structure according to Formula 1 or Formula 2, wherein the nucleotide analog is present in the composition effective to inhibit a viral polymerase of an HCV virus or to act as a substrate for the viral polymerase of the HCV virus;
wherein Z1 and Z2 are independently H, alkyl, halogen, OR5, SR5, NR5R6, CO-alkyl, CO-aryl, or CO-alkoxyalkyl, and wherein W is H, OR5, SR5, NR5R6, NH(NR5R6), N(alkyl)(NR5R6), CN, C(O)NR5R6, C(NH)NR5R6, or halogen;
wherein V is hydrogen, halogen, OR5, SR5, NR5R6, NH(NR5R6), N(alkyl)(NR5R6), CN, C(O)NR5R6, or C(NH)NR5R6, and wherein Y is H, alkyl, halogen, OR5, SR5, NR5R6, CO-alkyl, CO-aryl, or CO-alkoxyalkyl;
X is a covalent bond between the C4′
-atom of the sugar and the carbon atom in the phosphonate group, O, CH2, CHR5, CHHalogen, or C(Halogen)2;
D is CH2, CHHalogen, or C(Halogen)2;
R1 and R2 are independently H, phosphate, or a group that is preferentially removed in a hepatocyte to yield a corresponding OH group;
R1′
, R2′
, R3′
, and R4′
are independently H or alkyl;
R3 and R4 are H, or where at least one of R1′
, R2′
, R3′
, and R4′
is alkyl, R3 and R4 are independently H, phosphate, acyl, alkyl, or a group that is preferentially removed in the hepatocyte to a corresponding C2′
-OH group or C3′
-OH group;
R5 and R6 are independently H, alkyl, or acyl.
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Abstract
Pharmaceutical compositions comprise a nucleotide analog with a phosphonate group at a concentration effective to act as a substrate and/or inhibitor of a viral polymerase, and especially of the HCV RNA dependent RNA polymerase.
124 Citations
14 Claims
-
1. A pharmaceutical composition comprising:
-
a nucleotide analog having a structure according to Formula 1 or Formula 2, wherein the nucleotide analog is present in the composition effective to inhibit a viral polymerase of an HCV virus or to act as a substrate for the viral polymerase of the HCV virus;
wherein Z1 and Z2 are independently H, alkyl, halogen, OR5, SR5, NR5R6, CO-alkyl, CO-aryl, or CO-alkoxyalkyl, and wherein W is H, OR5, SR5, NR5R6, NH(NR5R6), N(alkyl)(NR5R6), CN, C(O)NR5R6, C(NH)NR5R6, or halogen;
wherein V is hydrogen, halogen, OR5, SR5, NR5R6, NH(NR5R6), N(alkyl)(NR5R6), CN, C(O)NR5R6, or C(NH)NR5R6, and wherein Y is H, alkyl, halogen, OR5, SR5, NR5R6, CO-alkyl, CO-aryl, or CO-alkoxyalkyl;
X is a covalent bond between the C4′
-atom of the sugar and the carbon atom in the phosphonate group, O, CH2, CHR5, CHHalogen, or C(Halogen)2;
D is CH2, CHHalogen, or C(Halogen)2;
R1 and R2 are independently H, phosphate, or a group that is preferentially removed in a hepatocyte to yield a corresponding OH group;
R1′
, R2′
, R3′
, and R4′
are independently H or alkyl;
R3 and R4 are H, or where at least one of R1′
, R2′
, R3′
, and R4′
is alkyl, R3 and R4 are independently H, phosphate, acyl, alkyl, or a group that is preferentially removed in the hepatocyte to a corresponding C2′
-OH group or C3′
-OH group;
R5 and R6 are independently H, alkyl, or acyl. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14)
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Specification