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Details for Patent: 8,278,435

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Details for Patent: 8,278,435

Title:N-pyrazole A2A receptor agonists
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 A.sub.2A adenosine receptor, compositions comprising these compounds, and methods for using these compounds to stimulate mammalian coronary vasodilation for imaging the heart. ##STR00001##
Inventor(s): Zablocki; Jeff A. (Mountain View, CA), Elzein; Elfatih O. (Fremont, CA), Palle; Venkata (Pune, IN), Belardinelli; Luiz (Palo Alto, CA)
Assignee: Gilead Sciences, Inc. (Foster City, CA)
Filing Date:Dec 14, 2010
Application Number:12/968,110
Claims:1. A method for the preparation of (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminop- urin-2-yl}pyrazol-4-yl)-N-methylcarboxamide: ##STR00021## comprising heating a compound of formula 10: ##STR00022## in excess methylamine to provide (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-- 6-aminopurin-2-yl}pyrazol-4-yl)-N-methylcarboxamide.

2. The method of claim 1, wherein the method comprises an aqueous solution of methylamine.

3. The method of claim 1, wherein the method comprises heating at a temperature of about 65.degree. C.

4. The method of claim 1, wherein the method comprises an aqueous solution of methylamine and heating at a temperature of about 65.degree. C.

5. The method of claim 1, wherein the method further comprises preparing the compound of formula 10: ##STR00023## by reacting a compound of formula 1: ##STR00024## with ethoxycarbonylmalondialdehyde.

6. The method of claim 5, wherein preparing the compound of formula 10 comprises a temperature of about 80.degree. C.

7. The method of claim 5, wherein preparing the compound of formula 10 comprises a mixture of CH.sub.3OH and CH.sub.3COOH as a solvent.

8. The method of claim 7, wherein the mixture of CH.sub.3OH and CH.sub.3COOH is in a 1:1 ratio.

9. The method of claim 5, wherein preparing the compound of formula 10 comprises a temperature of about 80.degree. C. and a 1:1 mixture of CH.sub.3OH and CH.sub.3COOH as a solvent.

10. The method of claim 5, wherein the method further comprises preparing the compound of formula 1: ##STR00025## by reacting a compound of formula 9: ##STR00026## with hydrazine hydrate.

11. The method of claim 10, wherein the method further comprises preparing the compound of formula 9: ##STR00027## by reacting a compound of formula 8: ##STR00028## with NH.sub.3.

12. The method of claim 11, wherein the method further comprises preparing the compound of formula 8: ##STR00029## by reacting a compound of formula 7: ##STR00030## with CH.sub.3(CH.sub.2).sub.4ONO and CH.sub.2I.sub.2.

13. The method of claim 12, wherein the method further comprises preparing the compound of formula 7: ##STR00031## by reacting a compound of formula 6: ##STR00032## with POCl.sub.3.

14. The method of claim 13, wherein the method further comprises preparing the compound of formula 6: ##STR00033## by reacting guanosine: ##STR00034## with acetic anhydride.
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