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Details for Patent: 6,448,253

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Details for Patent: 6,448,253

Title: Adenosine A3 receptor modulators
Abstract:The compounds of formula I wherein R, R.sup.1, R.sup.2 R.sup.3 and A have the meanings given in the specification, are endowed with selective A.sub.3 adenosine receptor agonist activity. These compounds can be used in a pharmaceutical composition to treat disorders caused by excessive activation of the A.sub.3 receptor, or can be used in a diagnostic application to determine the relative binding of other compounds to the A.sub.3 receptor.
Inventor(s): Baraldi; Pier Giovanni (Ferrara, IT)
Assignee: King Pharmaceuticals Research and Development, Inc. (Cary, NC)
Filing Date:Sep 16, 1998
Application Number:09/154,435
Claims:1. A compound of the following formula: ##STR17##

wherein: A is imidazole, pyrazole, or triazole; R is --C(X)R.sup.1, --C(X)--N(R.sup.1).sub.2, --C(X)OR.sup.1, --C(X)SR.sup.1, --SO.sub.n --R.sup.1, --SO.sub.n OR.sup.1, --SO.sub.n --SR.sup.1, or SO.sub.n --N(R.sup.1).sub.2 ; R.sup.1 is hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, heteroaryl, heterocyclic, lower alkenyl, lower alkanoyl, or, if linked to a nitrogen atom, then taken together with the nitrogen atom, forms an azetidine ring or a 5-6 membered heterocyclic ring containing one or more heteroatoms; R.sup.2 is hydrogen, alkyl, substituted alkyl, aralkyl, substituted aralkyl, heteroaryl, substituted heteroaryl or aryl; R.sup.3 is furan, pyrrole, thiophene, benzofuran, benzopyrrole, benzothiophene, optionally substituted with one or more substituents selected from the group consisting of hydroxy, acyl, alkyl, alkoxy, alkenyl, alkynyl, substituted alkyl, substituted alkoxy, substituted alkenyl, substituted alkynyl, amino, substituted amino, aminoacyl, acyloxy, acylamino, alkaryl, aryl, aryloxy, azido, carboxyl, carboxylalkyl, cyano, halo, nitro, heteroaryl, heteroaryloxy, heterocyclic, heterocyclooxy, aminoacyloxy, thioalkoxy, substituted thioalkoxy, thioaryloxy, thioheteroaryloxy, --SO-alkyl, --SO-substituted alkyl, --SO-aryl, --SO-heteroaryl, --SO.sub.2 -alkyl, --SO.sub.2 -substituted alkyl, --SO.sub.2 -aryl, --SO.sub.2 -heteroaryl, and trihalomethyl; X is O, S, or NR.sup.1 ; n is 1 or 2; and pharmaceutically acceptable salts thereof.

2. The compound of claim 1 wherein R is --C(X)R.sup.1, --C(X)--N(R.sup.1).sub.2, --SO.sub.n R.sup.1 or --SO.sub.n --N(R.sup.1).sub.2 wherein X is O or S.

3. The compound of claim 1 wherein R.sup.1 is selected from the group consisting of hydrogen, alkyl, alkenyl and aryl.

4. The compound of claim 1 wherein R.sup.2 is selected from the group consisting of hydrogen, alkyl and aryl.

5. The compound of claim 1 wherein R.sup.3 is furan.

6. The compound of claim 1 wherein X is O.

7. The compound of claim 1 wherein A is a triazolo ring.

8. The compound of claim 1 wherein A is a pyrazolo ring.

9. A method of treating hypertension, inflammation, allergic reactions, mast cell degranulation, and cardiac hypoxia, and protecting against cerebral ischemia, comprising administering to a patient in need of treatment thereof an effective amount of a compound of claim 1.

10. The method of claim 9 wherein R is --C(X)R.sup.1, --C(X)--N(R.sup.1).sub.2, --SO.sub.n R.sup.1 or --SO.sub.n --N(R.sup.1).sub.2 wherein X is O or S.

11. The method of claim 9 wherein R.sup.1 is selected from the group consisting of hydrogen, alkyl, alkenyl and aryl.

12. The method of claim 9 wherein R.sup.2 is selected from the group consisting of hydrogen, alkyl and aryl.

13. The method of claim 9 wherein X is O.

14. The method of claim 9 wherein A is a pyrazolo ring.

15. The method of claim 9 wherein A is a triazolo ring.

16. The method of claim 9 wherein the disorder to be treated is selected from the group consisting of cardiac hypoxia and cerebral ischemia.

17. A compound selected from the group of compounds consisting of: 5-[[(3-Chlorophenyl)amino]carbonyl]amino-8-methyl-2-(2-furyl)-pyrazolo[4,3- e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(4-Methoxyphenyl)amino]carbonyl]amino-8-methyl-2-(2-furyl)-pyrazolo[4,3 -e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(3-Chlorophenyl)amino]carbonyl]amino-8-ethyl-2-(2-furyl)-pyrazolo[4,3-e ]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(4-Methoxyphenyl)amino]carbonyl]amino-8-ethyl-2-(2-furyl)-pyrazolo[4,3- e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(3-Chlorophenyl)amino]carbonyl]amino-8-propyl-2-(2-furyl)-pyrazolo[4,3- e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(4-Methoxyphenyl)amino]carbonyl]amino-8-propyl-2-(2-furyl)-pyrazolo[4,3 -e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(3-Chlorophenyl)amino]carbonyl]amino-8-butyl-2-(2-furyl)-pyrazolo[4,3-e ]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(4-Methoxyphenyl)amino]carbonyl]amino-8-butyl-2-(2-furyl)-pyrazolo[4,3- e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(3-Chlorophenyl)amino]carbonyl]amino-8-isopentyl-2-(2-furyl)-pyrazolo[4 ,3-e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(4-Methoxyphenyl)amino]carbonyl]amino-8-isopentyl-2-(2-furyl)-pyrazolo[ 4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(3-Chlorophenyl)amino]]carbonyl]amino-8-(2-isopentenyl)-2-(2-furyl)pyra zolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(4-Methoxyphenyl)amino]carbonyl]amino-8-(2-isopentenyl)-2-(2-furyl)-pyr azolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(3-Chlorophenyl)amino]carbonyl]amino-8-(2-phenylethyl)-2 (2-furyl)-pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(4-Methoxyphenyl)amino]carbonylamino-8-(2-phenylethyl)-2-(2-furyl)-pyra zolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(3-Chlorophenyl)amino]carbonyl]amino-8-(3-phenylpropyl)-2-(2-furyl)-pyr azolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[[(4-Methoxyphenyl)amino]carbonyl]amino-8-(3-phenylpropyl)-2-(2-furyl)-py razolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine, 5-[(Benzyl)carbony]amino-8-isopentyl-2-(2-furyl)-pyrazolo[4,3-e]-1,2,4-tria zolo[1,5-c]pyrimidine, and 5-[(Benzyl)carbonyl]amino-8-(3-phenylpropyl)-2-(2-furyl)-pyrazolo[4,3-e]-1, 2,4-triazolo[1,5-c]pyrimidine.

18. A method of treating hypertension, inflammation, allergic reactions, mast cell degranulation and cardiac hypoxia, and protecting against cerebral ischemia, comprising administering to a patient in need of treatment thereof an effective amount of a compound of claim 17.

19. A compound selected from the group of compounds consisting of: 5-[[(3-Chlorophenyl)amino]]carbonyl]amino-8-(2-isopentenyl)-2-(2-furyl)pyra zolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine, and 5-[[(4-Methoxyphenyl)amino]carbonyl]amino-8-(2-isopentenyl)-2-(2-furyl)-pyr azolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine.
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