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2-(N-pyrazolo)adenosines with application as adenosine A2A receptor agonists

a technology of adenosine receptor and adenosine a, which is applied in the field of npyrazole substituting 2adenosine compounds to achieve the effect of convenient coronary imaging and convenient us

Inactive Publication Date: 2019-04-16
GILEAD SCI INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent relates to certain compounds that can be used with radioactive imaging agents to help with coronary imaging. This makes it easier to get accurate images of the heart's blood vessels.

Problems solved by technology

However, there is a high incidence of drug-related adverse side effects during pharmacological stress imaging with these drugs, such as headache and nausea, that could be improved with new therapeutic agents.

Method used

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  • 2-(N-pyrazolo)adenosines with application as adenosine A<sub>2A </sub>receptor agonists
  • 2-(N-pyrazolo)adenosines with application as adenosine A<sub>2A </sub>receptor agonists
  • 2-(N-pyrazolo)adenosines with application as adenosine A<sub>2A </sub>receptor agonists

Examples

Experimental program
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Effect test

example 1

[0081]

Ethyl 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazole-4-carboxylate (12)

[0082]To a suspension of 2-hydrazinoadenosine (0.025 g, 0.08 mmol) in a 1:1 mixture of MeOH / AcOH was added (ethoxycarbonyl)malondialdehyde (0.019 g, 0.12 mmol) and the mixture was heated at 80° C. for 3 h. The precipitate formed was collected by filtration and washed with EtOH and ether to afford 12. 1HNMR (DMSO-d6) δ1.25 (t, 3H), 3.5 (m, 1H), 3.6 (m, 1H), 3.8 (d, 1H), 4.15 (d, 1H), 4.55 (m, 1H), 5.0 (t, 1H), 5.2 (d, 1H), 5.5 (d, 1H), 5.5 (d, 1H), 5.9 (d, 1H), 7.15-7.3 (m, 5H), 7.8 (br s, 2H), 8.1 (s, 1H), 8.4 (s, 1H), 8,9 (s, 1H).

example 2

[0083]

(4S,2R,3R,5R)-2-{6-Amino-2-[4-(4-chlorophenyl)pyrazolyl]purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol (13)

[0084]To a suspension of 2-hydrazinoadenosine (0.025 g, 0.08 mmol) in a 1:1 mixture of MeOH / AcOH was added 2-(4-chloro)phenylmalondialdehyde (0.022 g, 0.12 mmol) and the mixture was heated at 80° C. for 3 h. The precipitate formed was collected by filtration and washed with EtOH and Ether to afford 13. 1HNMR (DMSO-d6) δ3.5 (m, 1H), 3.6 (m, 1H), 3.8 (d, 1H), 4.15 (d, 1H), 4.2 (q, 2H), 4.55 (m, 1H), 5.9 (d, 1H), 7.45 (d, 2H), 7.75 (d, 2H), 8.25 (s, 1H), 8.35 (s, 1H), 8.9 (s, 1H).

example 3

[0085]

(4S,2R,3R,5R)-2-{6-Amino-2-[4-(4-metboxyphenyl)pyrazolyl]purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol (14)

[0086]To a suspension of 2-hydrazinoadenosine (0.025 g, 0.08 mmol) in a 1:1 mixture of MeOH / AcOH was added 2-(4-methoxy)phenylmalondialdehyde (0.022 g, 0.12 mmol) and the mixture was heated at 80° C. for 3 h. The precipitate formed was collected by filtration and washed with EtOH and Ether to afford 14. 1HNMR (DMSO-d6) δ3.55 (m, 1H), 3.65 (m, 1H), 3.75 (s, 3H), 3.9 (d, 1H), 4.15 (d, 1H), 4.6 (m, 1H), 5.9 (d, 1H), 6.75 (d, 2H), 7.6 (d, 2H), 8.15 (s, 1H), 8.35 (s, 1H), 8.8 (s, 1H).

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Abstract

N-pyrazole substituted 2-adenosine compounds and methods for using the compounds as A2A-adenosine receptor agonists useful to stimulate mammalian coronary vasodilation for therapeutic purposes and as adjuncts in cardiological imaging.

Description

[0001]This application is a 371 of PCT / US00 / 40281 filed Jun 21, 2000 which is a continuation in part of Ser. No. 09 / 338,185, filed Jun. 22, 1999 now U.S. Pat. No. 6,403,567.BACKGROUND OF THE INVENTION[0002]1. Field of Invention[0003]This invention includes N-pyrazole substituted 2-adenosine compounds that are useful as A2A receptor agonists. The compounds of this invention are vasodilating agents that are useful as heart imaging aids that aid in the identification of mammals, and especially humans who are suffering from coronary disorders such as poor coronary perfusion which is indicative of coronary artery disease (CAD). The compounds of this invention can also be used as therapeutics for coronary artery disease as well as any other disorders mediated by the A2A receptor.[0004]2. Description of the Art[0005]Pharmacological stress is frequently induced with adenosine or dipyridamole in patients with suspected CAD before imaging with T1 scintigraphy or echocardiography. Both drugs e...

Claims

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Application Information

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IPC IPC(8): C07H19/16C07D473/34C07H19/00
CPCC07H19/00C07H19/16C07D473/16C07D473/34
Inventor ZABLOCKI, JEFF A.ELZEIN, ELFATIH O.PALLE, VENKATA P.BELARDINELLI, LUIZ
Owner GILEAD SCI INC
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