# US 5,705,490 A · Polysubstituted benzimidazoles as antiviral agents

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- Number: US 5,705,490 A
- Document ID: US5705490A
- Status: Granted
- Kind: A
- Application number: 08/471,059
- Filed: 1995-06-06
- Granted: 1998-01-06
- Earliest claimed: 1990-11-01
- Assignees: The Regents of the University of Michigan
- Inventors: Leroy B. Townsend; John C. Drach
- Web page: https://patentgrep.com/patent/US5705490A

## CPC

- A61K 31/70: Carbohydrates; Sugars; Derivatives thereof (sorbitol A61K31/047)
- A61K 31/415: 1,2-Diazoles
- A61K 31/4184: condensed with carbocyclic rings, e.g. benzimidazoles
- A61K 31/52: Purines, e.g. adenine
- A61K 31/7056: containing five-membered rings with nitrogen as a ring hetero atom
- C07D 235/24: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D 235/26: Oxygen atoms
- C07D 235/30: Nitrogen atoms not forming part of a nitro radical
- C07H 19/052: Imidazole radicals
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

This invention relates to novel polysubstituted benzimidazoles and compositions and their use in the treatment of viral infections. The polysubstituted benzimidazoles and compositions of the present invention exhibit antiviral properties against viruses of the herpes family, particularly human cytomegalovirus (HCMV) and herpes simplex viruses (HSV).

## Claims

### Claim 1

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 Cl, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is NH.sub.2 and R.sub.6 is 2'-deoxy-.beta.-D-erythropentofuranosyl (denoted compound 113 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 Cl and R.sub.6 is .beta.-D-arabinofuranosyl (denoted compound 134 in the text); and
R.sub.1 is H, 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 5'-O-acetyl-.beta.-D-ribofuranosyl (denoted compound 42a in the text).

### Claim 2 (depends on 1)

The antiviral compound of claim 1, 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 2'-deoxy-.beta.-D-erythro-pentofuranosyl (denoted compound 113 in the text).

### Claim 3 (depends on 1)

The antiviral compound of claim 1, 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 Cl and R.sub.6 is .beta.-D-arabinofuranosyl (denoted compound 134 in the text).

### Claim 4 (depends on 1)

The antiviral compound of claim 1, 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 Cl and R.sub.6 is 5'-O-acetyl-.beta.-D-ribofuranosyl (denoted compound 42a in the text).

### Claim 5

An antiviral composition comprising a pharmaceutically acceptable carrier and an 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 Cl, R.sub.3 is Cl, R.sub.4 is H, R.sub.5 is NH.sub.2 and R.sub.6 is 2'-deoxy-.beta.-D-erythropentofuranosyl (denoted compound 113 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 Cl and R.sub.6 is .beta.-D-arabinofuranosyl (denoted compound 134 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 Cl and R.sub.6 is 5'-O-acetyl-.beta.-D-ribofuranosyl (denoted compound 42a in the text).

### Claim 6 (depends on 5)

The antiviral composition of claim 5, 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 2'-deoxy-.beta.-D-erythro-pentofuranosyl (denoted compound 113 in the text).

### Claim 7 (depends on 5)

The antiviral composition of claim 5, 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 Cl and R.sub.6 is .beta.-D-arabinofuranosyl (denoted compound 134 in the text).

### Claim 8 (depends on 5)

The antiviral composition of claim 5, 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 Cl and R.sub.6 is 5'-O-acetyl-.beta.-D-ribofuranosyl (denoted compound 42a in the text).

### Claim 9 (depends on 5)

The antiviral composition of claim 5, further comprising ganciclovir.

### Claim 10

A method for treating a herpes viral infection comprising administering to the infected host a therapeutically effective amount of a compound, or a pharmaceutically acceptable salt 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 2'-deoxy-.beta.-D-erythropentofuranosyl (denoted compound 113 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 Cl and R.sub.6 is .beta.-D-arabinofuranosyl (denoted compound 134 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 Cl and R.sub.6 is 5'-O-acetyl-.beta.-D-ribofuranosyl (denoted compound 42a in the text); and
R.sub.1 is H, 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 2',3',5'-tri-O-acetyl-.beta.-D-ribofuranosyl (denoted compound 42 in the text).

### Claim 11 (depends on 10)

The method of claim 10, 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 2'-deoxy-.beta.-D-erythro-pentofuranosyl (denoted compound 113 in the text).

### Claim 12 (depends on 10)

The method of claim 10, 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 Cl and R.sub.6 is .beta.-D-arabinofuranosyl (denoted compound 134 in the text).

### Claim 13 (depends on 10)

The method of claim 10, 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 Cl and R.sub.6 is 5'-O-acetyl-.beta.-D-ribofuranosyl (denoted compound 42a in the text).

### Claim 14 (depends on 10)

The method of claim 10, 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 Cl and R.sub.6 is 2',3',5'-tri-O-acetyl-.beta.-D-ribofuranosyl (denoted compound 42 in the text).