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Details for Patent: 4,654,347

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Details for Patent: 4,654,347

Title: Aryl and heteroaryl[[7-(3-disubstituted amino)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanones
Abstract:Novel aryl and heteroaryl[7-(3-substituted amino phenyl)-pyrazolo[1,5-a]pyrimidin-3-yl]methanones useful as anxiolytic, antiepileptic and sedative-hypnotic agents and as skeletal muscle relaxants, methods of using the novel compounds, compositions containing them and processes for this production.
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 13, 1985
Application Number:06/732,985
Claims:1. A compound selected from those of the formula: ##STR5## wherein R.sub.1 is selected from the group consisting of unsubstituted phenyl; phenyl mono- or disubstituted by halogen, alkyl(C.sub.1 -C.sub.3) or alkoxy(C.sub.1 -C.sub.3); phenyl monosubstituted 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 groups consisting of halogen, alkyl(C.sub.1 -C.sub.3) and alkoxy(C.sub.1 -C.sub.3);

R.sub.2 is selected from the group consisting of hydrogen and alkyl(C.sub.1 -C.sub.3);

R.sub.3 is ##STR6## R.sub.4 is selected from the group consisting of hydrogen, alkenyl(C.sub.2 -C.sub.6), --CH.sub.2 C.tbd.CH, cycloalkyl(C.sub.3 -C.sub.6)methyl, --CH.sub.2 OCH.sub.3 and --CH.sub.2 CH.sub.2 OCH.sub.3 ; and

R.sub.5 is selected from the group consisting of hydrogen, cycloalkyl(C.sub.3 -C.sub.6), --O--alkyl(C.sub.1 -C.sub.6), --NH--alkyl(C.sub.1 -C.sub.3), --N--dialkyl(C.sub.1 -C.sub.3), --(CH.sub.2).sub.n --O--alkyl(C.sub.1 -C.sub.3), --(CH.sub.2).sub.n --NH--alkyl(C.sub.1 -C.sub.3), --(CH.sub.2).sub.n --N--dialkyl(C.sub.1 -C.sub.3), where n is an integer 1-3 inclusive, and R.sub.5 may be alkyl(C.sub.1 -C.sub.6), when R.sub.4 is not hydrogen.

2. A compound according to claim 1, wherein R.sub.1 is selected from the group consisting of unsubstituted phenyl; phenyl mono-substituted by halogen, alkyl(C.sub.1 -C.sub.3), alkoxy(C.sub.1 -C.sub.3) or trifluoromethyl; thienyl; furanyl; and pyridinl; R.sub.2 is hydrogen; R.sub.4 is selected from the group consisting of alkenyl(C.sub.2 -C.sub.6) and --CH.sub.2 --C.tbd.CH; and R.sub.5 is selected from the group consisting of cycloalkyl(C.sub.3 -C.sub.6); --O--alkyl(C.sub.1 -C.sub.6); --N--dialkyl(C.sub.1 -C.sub.3); and, when R.sub.4 is not hydrogen, alkyl(C.sub.1 -C.sub.6).

3. The compound according to claim 2, N-[3-(3-benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-methylcyclobutaneca rboxamide.

4. The compound according to claim 2, N-[3-(3-benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-methylcyclopropanec arboxamide.

5. The compound according to claim 2, [3-(3-benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]methylcarbamic acid, methyl ester.

6. The compound according to claim 2, [3-(3-benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]ethylcarbamic acid, methyl ester.

7. The compound according to claim 2, N-methyl-N-[3-[3-(2-thienylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]c yclopropanecarboxamide.

8. The compound according to claim 2, [3-(3-benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]methylcarbamic acid, methyl ester.

9. The compound according to claim 2, [3-(3-benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]ethylcarbamic acid, ethyl ester.

10. The compound according to claim 2, N-2-propenyl-N-[3-[3-(2-thienylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phen yl]acetamide.

11. The compound according to claim 2, ethyl[3-[3-(2-thienylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]carbami c acid, ethyl ester.

12. The compound according to claim 2, N-[3-(3-benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-2-propenylacetamide

13. The compound according to claim 2, N-[3-(3-benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-2-propynylacetamide .

14. A method of ameliorating anxiety in a mammal which comprises administering an amount of a compound of claim 1 sufficient to relieve anxiety.

15. 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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