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US 7,094,768 B2Granted
Nucleoside derivatives for treating hepatitis C virus infection
AssigneeGenelabs Technologies, Inc.
InventorsChristopher D. Roberts, Jesse Keicher, Natalia B. Dyatkina
Life of this patent
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Abstract
Disclosed are 6-hydroxyamino- or a 6-alkoxyamino-7-deazapurine-ribofuranose derivatives, salts, pharmaceutical compositions, and methods of use thereof for treating viral infections caused by a flaviviridae family virus, such as hepatitis C virus.
Claims7
A compound of Formula I below:
- wherein:
- W is selected from the group consisting of hydrogen, monophosphate, diphosphate, and triphosphate;
- W1 and W2 are hydrogen;
- R is selected from the group consisting of hydrogen or (C1–C3)alkyl;
- R1 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl and substituted alkynyl;
- Y is a bond, —CH2— or —O—;
- Y′ is selected from the group consisting of hydrogen, halo, hydroxyl, thioalkyl, amino and substituted amino;
- Z is selected from the group consisting of formyl, halo, —B(OH)2, nitro, alkenyl, substituted alkenyl, acetylenyl and substituted acetylenyl of the formula —C≡C—R4;
- R4 is selected from the group consisting of hydrogen, phenyl, substituted phenyl, heteroaryl, substituted heteroaryl, —Si(R8)3, carboxyl, carboxyl esters, and —C(O)NR6R7 where R6 and R7 are independently hydrogen, alkyl or R6 and R7 together with the nitrogen atom pendent thereto are joined to form a heterocyclic, substituted heterocyclic, heteroaryl or substituted heteroaryl group;
- and
- each R8 is independently (C1–C4)alkyl or phenyl;
- or pharmaceutically acceptable salts thereof.
9 more elements
A compound of Formula II
- wherein:
- W is selected from the group consisting of hydrogen, monophosphate, diphosphate, and triphosphate;
- R is selected from the group consisting of hydrogen or (C1–C3)alkyl;
- Z is selected from the group consisting of formyl, halo, —B(OH)2, nitro, alkenyl, substituted alkenyl, acetylenyl and substituted acetylenyl of the formula —C≡C—R4;
- R4 is selected from the group consisting of hydrogen, phenyl, substituted phenyl, heteroaryl, substituted heteroaryl, —Si(R8)3, carboxyl, carboxyl esters, and —C(O)NR6R7 where R6 and R7 are independently hydrogen, alkyl or R6 and R7 together with the nitrogen atom pendent thereto are joined to form a heterocyclic, substituted heterocyclic, heteroaryl or substituted heteroaryl group;
- and
- each R8 is independently (C1–C4)alkyl or phenyl;
- or pharmaceutically acceptable salts thereof.
5 more elements
A compound selected from the group consisting of:
- 1-(6-hydroxylamino-7-ethynyl-7-deazapurin-9-yl)-2-methyl-β-D-ribofuranose (1);
- 1-(6-hydroxylamino-7-(2-phenylethyn-1-yl)-7-deazapurin-9-yl)-2-methyl-β-D-ribofuranose (2);
- 1-(6-hydroxylamino-7-(2-(pyridin-2-yl)-ethyn-1-yl)-7-deazapurin-9-yl)-2-methyl-β-D-ribofuranose (3);
- 1-(6-hydroxylamino-7-(2-(4-fluorophenyl)ethyn-1-yl)-7-deazapurin-9-yl)-2-methyl-β-D-ribofuranose (4);
- 1-(6-hydroxylamino-7-(2-(4-methylphenyl)ethyn-1-yl)-7-deaza-purin-9-yl)-2-methyl-β-D-ribofuranose (5);
- 1-(6-hydroxylamino-7-(2-carboxylethyn-1-yl)-7-deazapurin-9-yl)-2-methyl-β-D-ribofuranose (6);
- 1-(6-hydroxylamino-7-(2-ethylcarboxylethyn-1-yl)-7-deazapurin-9-yl)-2-methyl-β-D-ribofuranose (7);
- 1-(6-hydroxylamino-7-(2-carboxamidoethyn-1-yl)-7-deazapurin-9-yl)-2-methyl-β-D-ribofuranose (8);
- 1-(6-hydroxylamino-7-(2-trimethylsilylethyn-1-yl)-7-deazapurin-9-yl)-2-methyl-β-D-ribofuranose (9);
- 1-(6-hydroxylamino-7-ethenyl-7-deaza-purin-9-yl)-2-methyl-β-D-ribofuranose (10);
- 1-(6-hydroxylamino-7-formyl-7-deaza-purin-9-yl)-2-methyl-β-D-ribofuranose (11);
- 1-(6-hydroxylamino-7-(boronic acid)-7-deazapurin-9-yl)-2-methyl-β-D-ribofuranose (13);
- 1-(6-hydroxylamino-7-(2,2-difluorovinyl)-7-deazapurin-9-yl)-2-methyl-β-D-ribofuranose (14);
- 1-(6-hydroxylamino-7-(2-cis-methoxyvinyl)-7-deazapurin-9-yl)-2-methy-β-D-ribofuranose (15);
- 1-(6-hydroxylamino-7-nitro-7-deaza-purin-9-yl)-2-methyl-β-D-ribofuranose (16);
- 1-(6-methoxyamino-7-ethynyl-7-deazapurin-9-yl)-2-methyl-β-D-ribofuranose (18);
- 1-(6-methoxyamino-7-nitro-7-deaza-purin-9-yl)-2-methyl-β-D-ribofuranose (19);
- 1-(6-methoxyamino-7-formyl-7-deaza-purin-9-yl)-2-methyl-β-D-ribofuranose (20);
- and pharmaceutically acceptable salts thereof.
16 more elements
Dependencies are inferred from the claim text.