# US 6,294,540 B1 · Carbocyclic nucleoside hemisulfate and its use in treating viral infections

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- Number: US 6,294,540 B1
- Document ID: US6294540B1
- Status: Granted
- Kind: B1
- Application number: 09/423,982
- Filed: 1999-12-01
- Granted: 2001-09-25
- Earliest claimed: 1997-05-17
- Assignees: Glaxo Wellcome Inc.
- Inventors: Alastair Couper Brodie; Martin Francis Jones; John Frederick Seager; Christopher John Wallis
- Web page: https://patentgrep.com/patent/US6294540B1

## CPC

- C07D 473/00: Heterocyclic compounds containing purine ring systems
- A61K 31/52: Purines, e.g. adenine
- A61K 31/535: having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K 31/55: having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61P 31/12: Antivirals
- A61P 31/18: for HIV
- A61P 31/20: for DNA viruses
- A61P 31/22: for herpes viruses
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The hemisulfate salt of (1S,4R)-cis-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol or a solvate of it is used in the treatment of viral infections.

## Claims

### Claim 1

The hemisufate salt of (1S,4R)-cis-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol or a solvate thereof.

### Claim 2 (depends on 1)

The compound as claimed in claim 1 in the form of a hydrate.

### Claim 3 (depends on 1)

A method for the treatment of an HIV or HBV infection in a human host which comprises administering to said host an effective amount of a compound as claimed in claim 1.

### Claim 4 (depends on 1)

A pharmaceutical formulation comprising a compound as claimed in claim 1 and a pharmaeutically acceptable carrier therefor.

### Claim 5 (depends on 4)

A pharmaceutical formulation as claimed in claim 4 in the form of a tablet, a capsule, or liquid formulation.

### Claim 6 (depends on 4)

A pharmaceutical formulation as claimed in claim 4 adapted for parenteral administration.

### Claim 7

A dicarboxylate salt of (1S,4R)-cis-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol wherein said dicarboxylate is selected from the group consisting of glutarate, hemisuberate, adipate, fumarate, hemisebacate and pimelate.

### Claim 8

The glutarate salt of (1S,4R)-cis-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol.

### Claim 9 (depends on 1)

A process for the preparation-of the compound claimed in claim 1 which process comprises:
adding sulfuric acid to (1S,4R)-cis-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol in a stoichiometric ratio of approximately 1:2.

### Claim 10 (depends on 1)

A process for the preparation of the compound claimed in claim 1 which process comprises:
adding to (1S,4R)-cis-4-2-cyclopentene-1-methanol sulfate (1:1 salt) to (1S,4R)-cis-4-2-cyclopentene-1-methanol in a substantially 1:1 molar ratio in solution.

### Claim 11

The benzoate or salicylate salt of (1S,4R)-cis-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene- 1 -methanol.

### Claim 12 (depends on 1)

A process for the preparation of the compound claimed in claim 1 which process comprises adding (1) sulfuric acid to (2) a salt of (1S,4R)-cis-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol selected from the group consisting of succinate, glutarate, hemisuberate, adipate, fumarate, hemisebacate and pimelate salts and any mixtures thereof, or from the group consisting of benzoate and salicylate salts and any mixtures thereof, wherein said sulfuric acid (1) and said salt (2) are present in the stoichiometric ratio of 2:1 if said salt (2) is a 1:1 salt, and 1:1 if said salt (2) is a 2:1 salt.

### Claim 13 (depends on 4, 5)

A pharmaceutical formulation as claimed in claim 4, 5, or 6 additionally comprising one or more therapeutic agents selected from the group consisting of nucleoside HIV reverse transcriptase inhibitors, non-nucleoside HIV reverse transcriptase inhibitors, HIV protease inhibitors, immune modulators selected from the group consisting of interleukin II, erythyropoetin and tucaresol, and α-interferon.