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Claims for Patent: 6,642,210

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Claims for Patent: 6,642,210

Title: 2-(N-pyrazolo)adenosines with application as adenosine A2A receptor agonists
Abstract:N-pyrazole substituted 2-adenosine compounds and methods for using the compounds as A.sub.2 A-adenosine receptor agonists useful to stimulate mammalian coronary vasodilation for therapeutic purposes and as adjuncts in cardiological imaging.
Inventor(s): Zablocki; Jeff A. (Mountain View, CA), Elzein; Elfatih O. (Freemont, CA), Palle; Venkata P. (Sunnyvale, CA)
Assignee: CV Therapeutics, Inc. (Palo Alto, CA)
Application Number:10/018,446
Patent Claims: 1. A compound having the formula: ##STR20## wherein R.sup.1 =CH.sub.2 OH; R.sup.3 is selected from the group consisting of CO.sub.2 R.sup.20, --CONR.sup.7 R.sup.8, and aryl, wherein the aryl substituent is optionally substituted with from 1 to 3 substituents independently selected from the group consisting of halo, alkyl, and OR.sup.20 ; R.sup.7 is selected from the group consisting of hydrogen, straight or branched C.sub.1-15 alkyl and C.sub.3-8 cycloalkyl, wherein the alkyl substituent is optionally substituted with from 1 to 3 substituents independently selected from the group consisting of aryl and CO.sub.2 R.sup.20, and wherein the optional aryl substituent is optionally substituted with halo; R.sup.8 is selected from the group consisting of hydrogen, straight or branched C.sub.1.sub.15 alkyl and C.sub.3-8 cycloalkyl; R.sup.20 is selected from the group consisting of hydrogen and C.sub.1-15 alkyl; and wherein R.sup.2 and R.sup.4 are hydrogen.

2. The compound of claim 1 wherein R.sup.3 is CO.sub.2 R.sup.20 ; and R.sup.20 is selected from the group consisting of hydrogen and C.sub.1-4 alkyl.

3. The compound of claim 1 wherein R.sup.3 is CONR.sup.7 R.sup.8 ; R.sup.7 is selected from the group consisting of hydrogen, straight or branched C.sup.1-10 alkyl and C.sub.3-5 cycloalkyl, wherein the alkyl substituent is optionally substituted with from 1 to 2 substituents independently selected from the group consisting of aryl and CO.sub.2 R.sup.20 ; R.sup.8 is selected from the group consisting of hydrogen, straight and branched C.sub.1-3 alkyl and C.sub.3-5 cycloalkyl; and R.sup.20 is selected from the group consisting of C.sub.1-4 alkyl.

4. The compound of claim 1 wherein R.sup.3 is aryl, wherein the aryl substituent is optionally substituted with from 1 to 3 substituents independently selected from the group consisting of halo, alkyl and OR.sup.20 ; and R.sup.20 is selected from and the group consisting of C.sup.1-4 alkyl.

5. The compound of claim 2 wherein R.sup.3 is CO.sub.2 R.sup.20 ; and R.sup.20 is selected from the group consisting of hydrogen and C.sup.1-4 alkyl.

6. The compound of claim 3 wherein R 7 is selected from the group consisting of hydrogen, C.sub.1-3 alkyl and cyclopentyl, wherein the alkyl substituent is optionally substituted with from 1 to 2 substituents, independently selected from the group consisting of phenyl and CO.sub.2 R.sup.20 and wherein each optional phenyl substituent is optionally substituted with halo; R.sup.8 is selected from hydrogen and methyl; and R.sup.20 is selected from hydrogen and ethyl.

7. The compound of claim 4 wherein R.sup.3 is aryl, wherein the aryl substituent is phenyl optionally substituted with from 1 to 2 substituents independently selected from the group consisting of chloro, methyl and OR.sup.20 ; and R.sup.20 is methyl.

8. The compound of claim 1 selected from the group consisting of ethyl 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopur in-2-yl}pyrazole-4-carboxylate; (4S,2R,3R,5R)-2-{6-amino-2-[4-(4-chlorophenyl)-pyrazolyl]purin-9-yl}-5-(hyd roxymethyl)oxolane-3,4-diol; (4S,2R,3R,5R)-2-{6-amino-2-[4-(4-methoxyphenyl)pyrazolyl]purin-9-yl}-5-(hyd roxymethyl)oxolane-3,4-diol; (4S,2R,3R,5R)-2-{6-amino-2-[4-(4-methylphenyl)pyrazolyl]purin-9-yl}-5-(hydr oxymethyl)-oxolane-3,4-diol; (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopur in-2-yl}pyrazol-4-yl)-N-methylcarboxamide; 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxyrethyl)oxolan-2-yl]-6-aminopuri n-2-yl}pyrazole-4-carboxylic acid; (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopur in-2-yl}pyrazol-4-yl)-N,N-dimethylcarboxamide; (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopur in-2-yl}pyrazol-4-yl)-N-ethylcarboxamide; 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopuri n-2-yl}pyrazole-4-carboxamide; 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopuri n-2-yl}pyrazol-.sup.4 -yl)-N-(cyclopentyl)carboxamide; (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopur in-2-yl}pyrazol-4-yl)-N-[(4-chlorophenyl)methyl]carboxamide, and ethyl 2-[(1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-amin opurin-2-yl}pyrazol-4-yl)carbonylamino]acetate.

9. A method for stimulating coronary vasodilation in a mammal comprissing administering by intravenous bolus injection an amount of a compound of claim 1 that is sufficient to stress the heart and induce a coronary steal situation for the purposes of imaging the heart.

10. The method of claim 9 wherein the mammal is a human.

11. A pharmaceutical composition comprising a compound of claim 1 and one or mode pharmaceutical excipients.

12. The pharmaceutical composition of claim 11 wherein the pharmaceutical composition is in the form of a solution.

13. The compound of claim 8 wherein the compound is (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopu rin-2-yl}pyrazol-4-yl)-N-methylcarboxamide.

14. The compound of claim 8 wherein the compound is 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopur in-2-yl}pyrazol-4-yl)-N-(cyclopentyl)carboxamide.

15. The compound of claim 1 wherein the compound is (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5(hydroxymethyl)oxolan-2-yl]-6-aminopur in-2-yl}pyrazol-4-yl)-N-ethylcarboxamide.

16. A method of dilating the coronary vessels of a mammal, as an adjunct to angioplasty, with the pharmaceutical composition of claim 11.

17. A method for adjunctive therapy in conjunction with angioplasty in a mammal comprising administering to the mammal a therapeutically effective amount of a compound of claim 1.

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