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US 5,665,709 AGranted
Polysubstituted benzimidazole nucleosides as antiviral agents
AssigneeThe Regents of the University of Michigan
InventorsLeroy B. Townsend, John C. Drach
Life of this patent
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Abstract
Polysubstituted benzimidazole nucleosides, pharmaceutical compositions thereof, and their use in the treatment of herpes viral infections.
Claims36
An antiviral compound selected from the group consisting of compounds having the following formula, and pharmaceutically acceptable salts thereof:
- ##STR6## wherein:
- R.sub.1 is H, R.sub.2 is B, R.sub.3 is Br, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 57 in the text);
- R.sub.1 is H, R.sub.2 is F, R.sub.3 is F, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl) denoted compound 65 in the text);
- R.sub.1 is H, R.sub.2 is Cl, R.sub.3 is F, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 65a in the text);
- R.sub.1 is H, R.sub.2 is H, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 67 in the text);
- R.sub.1 is Cl, R.sub.2 is H, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is CF.sub.3 and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 81b in the text);
- R.sub.1 is Cl, R.sub.2 is H, R.sub.3 is CF.sub.3, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 81c in the text);
- R.sub.1 is H, R.sub.2 is Br, R.sub.3 is H, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 87 in the text);
- R.sub.1 is H, R.sub.2 is H, R.sub.3 is Br, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 90 in the text);
- R.sub.1 is Cl, R.sub.2 is Cl, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 92 in the text);
- and
- R.sub.1 is Br, R.sub.2 is Br, R.sub.3 is Br, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 103 in the text).
9 more elements
An antiviral composition comprising a pharmaceutically acceptable carrier and a compound selected from the group consisting of compounds having the following formula, and pharmaceutically acceptable salts thereof:
- ##STR7## wherein:
- R.sub.1 is H, R.sub.2 is Br, R.sub.3 is Br, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 57 in the text);
- R.sub.1 is H, R.sub.2 is F, R.sub.3 is F, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 65 in the text);
- R.sub.1 is H, R.sub.2 is Cl, R.sub.3 is F, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 65a in the text);
- R.sub.1 is H, R.sub.2 is H, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 67 in the text);
- R.sub.1 is Cl, R.sub.2 is H, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is CF.sub.3 and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 81b in the text);
- R.sub.1 is Cl, R.sub.2 is H, R.sub.3 is CF.sub.3, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 81c in the text);
- R.sub.1 is H, R.sub.2 is Br, R.sub.3 is H, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 87 in the text);
- R.sub.1 is H, R.sub.2 is H, R.sub.3 is Br, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 90 in the text);
- R.sub.1 is Cl, R.sub.2 is Cl, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 92 in the text);
- and
- R.sub.1 is Br, R.sub.2 is Br, R.sub.3 is Br, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 103 in the text).
9 more elements
A method for treating a herpes viral infection comprising administering to the infected host a therapeutically effective amount a compound, or pharmaceutically acceptable salts or formulation thereof, selected from the group consisting of compounds having the following formula:
- ##STR8## wherein:
- R.sub.1 is H, R.sub.2 is Cl, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is NH.sub.2 and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 44 in the text);
- R.sub.1 is H, R.sub.2 is Cl, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is SCH.sub.2 C.sub.6 H.sub.5 and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 54 in the text);
- R.sub.1 is H, R.sub.2 is Br, R.sub.3 is Br, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 57 in the text);
- R.sub.1 is H, R.sub.2 is F, R.sub.3 is F, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 65 in the text);
- R.sub.1 is H, R.sub.2 is Cl, R.sub.3 is F, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 65a in the text);
- R.sub.1 is H, R.sub.2 is H, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 67 in the text);
- R.sub.1 is Cl, R.sub.2 is H, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is CF.sub.3 and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 81b in the text);
- R.sub.1 is Cl, R.sub.2 is H, R.sub.3 is CF.sub.3, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 81c in the text);
- R.sub.1 is H, R.sub.2 is Br, R.sub.3 is H, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 87 in the text);
- R.sub.1 is H, R.sub.2 is H, R.sub.3 is Br, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 90 in the text);
- R.sub.1 is Cl, R.sub.2 is Cl, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 92 in the text);
- and
- R.sub.1 is Br, R.sub.2 is Br, R.sub.3 is Br, R.sub.4 is H, R.sub.5 is Cl and R.sub.6 is .beta.-D-ribofuranosyl (denoted compound 103 in the text).
11 more elements
Dependencies are inferred from the claim text.