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Generated: June 23, 2018

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Claims for Patent: 4,626,538

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Summary for Patent: 4,626,538
Title: [7-(3-disubstituted amino)phenyl]pyrazolo[1,5-a]pyrimidines
Abstract:Novel [7-(3-disubstituted amino)phenyl]pyrazolo[1,5-a]pyrimidines useful as anxiolytic, antiepileptic and sedative-hypnotic agents as well as skeletal muscle relaxants, methods of using these compounds, compositions of matter containing them and processes for their 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)
Application Number:06/732,986
Patent Litigation and PTAB cases: See patent lawsuits and PTAB cases for patent 4,626,538
Patent Claims: 1. A compound of the formula: ##STR7## wherein R.sub.1 is selected from the group consisting of hydrogen, halogen, cyano and ##STR8## R.sub.2 is selected from the group consisting of hydrogen and alkyl (C.sub.1 -C.sub.3); R.sub.3 is ##STR9## R.sub.4 is selected from the group consisting of hydrogen, alkyl(C.sub.1 -C.sub.6) and alkoxy(C.sub.1 -C.sub.6); R.sub.5 is selected from the group consisting of hydrogen, alkyl(C.sub.1 -C.sub.6), 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.6 is selected from the group consisting of alkyl(C.sub.1 -C.sub.6), 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) and --(CH.sub.2).sub.n --N-dialkyl(C.sub.1 -C.sub.3), where n is an integer 1 to 3 inclusive.

2. A compound according to claim 1, wherein R.sub.1 is cyano or ##STR10## R.sub.2 is hydrogen; R.sub.4 is alkyl(C.sub.1 -C.sub.6), alkenyl(C.sub.2-C.sub.6) or --CH.sub.2 .tbd.CH; and R.sub.6 is alkyl (C.sub.1 -C.sub.6), cycloalkyl(C.sub.3 -C.sub.6) or --O-alkyl(C.sub.1 -C.sub.6).

3. The compound according to claim 2, which is N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylpropanamide.

4. The compound according to claim 2, which is N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide.

5. The compound according to claim 2, which is N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-propylacetamide.

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

7. The compound according to claim 2, which is 7-[3-[(methoxycarbonyl)methylamino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carb oxylic acid, ethyl ester.

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

9. The compound according to claim 2, which is ethyl(3-pyrazolo[1,5-a]pyrimidin-7-ylphenyl)carbamic acid, ethyl ester.

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

11. The compound according to claim 2, which is N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-2-propenylacetamide.

12. The compound according to claim 2, which is N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-2-propynylacetamide.

13. The compound according to claim 2, which is N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-methylacetamide.

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