# US 8,569,260 B2 · N-pyrazole A2A receptor agonists

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- Number: US 8,569,260 B2
- Document ID: US8569260B2
- Status: Granted
- Kind: B2
- Application number: 13/598,451
- Filed: 2012-08-29
- Published: 2013-03-07
- Granted: 2013-10-29
- Earliest claimed: 1999-06-22
- Assignees: Gilead Sciences, Inc.
- Applicants: Jeff A. Zablocki; Elfatih O. Elzein; Venkata P. Palle; Luiz Belardinelli
- Inventors: Jeff A. Zablocki; Elfatih O. Elzein; Venkata P. Palle; Luiz Belardinelli
- Web page: https://patentgrep.com/patent/US8569260B2

## CPC

- C07H 19/16: Purine radicals
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/08: Vasodilators for multiple indications
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 473/34: attached in position 6, e.g. adenine
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present disclosure provides a process for the preparation of 2-adenosine N-pyrazole compounds exemplified by the structure shown below that are potent and selective agonists for A2A adenosine receptor, compositions comprising these compounds, and methods for using these compounds to stimulate mammalian coronary vasodilation for imaging the heart.

## Claims

### Claim 1

A compound of formula;
named (4S,2R,3R,5R)-2-{6-amino-2-[4-(4-methylphenyl)pyrazolyl]purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol.

### Claim 2 (depends on 1)

A pharmaceutical composition comprising the compound of claim 1 and one or more pharmaceutically acceptable excipients.

### Claim 3 (depends on 2)

The pharmaceutical composition of claim 2, wherein the pharmaceutical composition is in the form of a solution.

### Claim 4 (depends on 1)

A method for stimulating coronary vasodilation in a human in need thereof by administering to the human the compound of claim 1.

### Claim 5 (depends on 4)

The method of claim 4, wherein the method comprises administering the compound intravenously by bolus.

### Claim 6 (depends on 1, 4)

The method of claim 4, wherein the method comprises administering an amount of the compound of claim 1 ranging from 0.01 to 100 mg/kg weight of the human.

### Claim 7 (depends on 1)

A method of treating coronary artery disease mediated by A2A receptor in a human in need thereof, wherein the method comprises administering a therapeutically effective amount of the compound of claim 1 to the human.

### Claim 8 (depends on 1)

A method of coronary imaging of a human in need thereof, comprising administering a radioactive imaging agent and the compound of claim 1 to the human.

### Claim 9 (depends on 1)

A method of dilating the coronary vessels of a human in need thereof, as an adjunct to angioplasty, wherein the method comprises administering a therapeutically effective amount of the compound of claim 1 to the human.

### Claim 10 (depends on 1)

A method for inhibition of platelet aggregation in a human in need thereof comprising administering a therapeutically effective amount of the compound of claim 1 to the human.