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Details for Patent: 4,521,422

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Details for Patent: 4,521,422

Title: Aryl and heteroaryl[7-(aryl and heteroaryl)pyrazolo[1,5-a]pyrimidin-3-yl]methanones
Abstract:Aryl and heteroaryl[7-(aryl and heteroaryl)pyrazolo[1,5-a]pyrimidin-3-yl]methanones which are new compounds active as anxiolytic, anticonvulsant, sedative-hypnotic and skeletal muscle relaxant agents in mammals and the novel process of making these compounds.
Inventor(s): Dusza; John P. (Nanuet, NY), Tomcufcik; Andrew S. (Old Tappan, NJ), Albright; Jay D. (Nanuet, NY)
Assignee: American Cyanamid Company (Stamford, CT)
Filing Date:May 24, 1984
Application Number:06/612,812
Claims:1. A compound selected from those of the formula: ##STR12## wherein R.sub.1 is selected from the group consisting of unsubstituted phenyl; phenyl mono- or di-substituted by halogen, alkoxy(C.sub.1 -C.sub.3) or alkyl(C.sub.1 -C.sub.3); phenyl mono-substituted by trifluoromethyl, alkylthio(C.sub.1 -C.sub.3), alkylamino(C.sub.1 -C.sub.3), dialkylamino(C.sub.1 -C.sub.3), methylenedioxy, alkylsulfonyl(C.sub.1 -C.sub.3) or alkanoylamino(C.sub.1 -C.sub.3); naphthalenyl; thiazolyl; biphenyl; thienyl; furanyl; pyridinyl; substituted thiazolyl; substituted biphenyl; substituted thienyl; and substituted pyridinyl wherein the substituents are selected from one or two of the group consisting of halogen, alkoxy(C.sub.1 -C.sub.3) and alkyl(C.sub.1 -C.sub.3); R.sub.2, R.sub.4 and R.sub.5 are each selected from the group consisting of hydrogen and alkyl(C.sub.1 -C.sub.3); and R.sub.3 is selected from the group consisting of unsubstituted phenyl, phenyl mono-substituted by halogen, trifluoromethyl, alkoxy(C.sub.1 -C.sub.3), amino, alkyl(C.sub.1 -C.sub.3), alkylamino(C.sub.1 -C.sub.6), dialkylamino(C.sub.1 -C.sub.3), alkanoylamino(C.sub.1 -C.sub.6), N-alkyl(C.sub.1 -C.sub.6)alkanoylamino(C.sub.1 -C.sub.6), cyano or alkylthio(C.sub.1 -C.sub.3); furanyl; thienyl; pyridinyl; and pyridine-1-oxide.

2. A compound according to claim 1, wherein R.sub.1 is 2-furanyl; R.sub.2, R.sub.4 and R.sub.5 are each hydrogen; and R.sub.3 is selected from the group consisting of 3-(trifluoromethyl)phenyl; 3-pyridinyl; and 4-pyridinyl.

3. A compound according to claim 1, wherein R.sub.1 is selected from the group consisting of unsubstituted phenyl; phenyl substituted by 4-methyl, 4-ethyl, 4-methoxy, 3,4-dimethoxy or 4-dimethylamino; 2-furanyl; 2-thienyl; 2-pyridinyl; and 4-pyridinyl; R.sub.2, R.sub.4 and R.sub.5 are each hydrogen; and R.sub.3 is selected from the group consisting of 3-(trifluoromethyl)phenyl; 3-pyridinyl; 4-pyridinyl; 3-[N-alkyl(C.sub.1 -C.sub.6)alkanoylamino(C.sub.1 -C.sub.6)]phenyl; and 3-[alkylamino(C.sub.1 -C.sub.6)].

4. The compound according to claim 1, phenyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.

5. The compound according to claim 1, (4-fluorophenyl)[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]-methanone.

6. The compound according to claim 1, phenyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.

7. The compound according to claim 1, phenyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanon e.

8. The compound according to claim 1, (4-methoxyphenyl)[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.

9. The compound according to claim 1, (3-fluorophenyl)[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.

10. The compound according to claim 1, [7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl][3-(trifluoromethyl)phenyl]m ethanone.

11. The compound according to claim 1, 2-thienyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]metha none.

12. The compound according to claim 1, 2-furanyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]metha none.

13. The compound according to claim 1, 2-furanyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.

14. The compound according to claim 1, [2-methyl-7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]phenylmethanone.

15. The compound according to claim 1, (4-methylphenyl)[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.

16. The compound according to claim 1, phenyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone, pyridine-1-oxide.

17. The compound according to claim 1, 2-pyridinyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.

18. The compound according to claim 1, 2-pyridinyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]met hanone.

19. The compound according to claim 1, 2-pyridinyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.

20. The compound according to claim 1, [7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]-2-thiazolyl-methanone.

21. The compound according to claim 1, 4-pyridinyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.

22. The compound according to claim 1, 4-pyridinyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]met hanone.

23. The compound according to claim 1, (2-fluorophenyl)[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.

24. The compound according to claim 1, (2-fluorophenyl)[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-y l]methanone.

25. The compound according to claim 1, [7-[3-(ethylamino)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-2-furanylmethanone

26. The compound according to claim 1, [7-[3-(ethylamino)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]phenylmethanone.

27. A method of meliorating anxiety in a mammal suffering from anxiety which comprises administering to said mammal an effective anxiolytic amount of a compound of claim 1.

28. A method of treating epilepsy in a mammal suffering from epilepsy which comprises administering to said mammal an effective anticonvulsant amount of a compound of claim 1.

29. A method of inducing sedation or hypnosis in a mammal which comprises administering to said mammal an effective sedative or hypnotic amount of a compound of claim 1.

30. A method of inducing skeletal muscle relaxation in a mammal which comprises administering to said mammal an effective skeletal muscle relaxant amount of a compound of claim 1.

31. A composition of matter in dosage unit form comprising from 2-750 mg of a compound of claim 1 in association with a pharmaceutically acceptable carrier.
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