(Substituted-phenyl)-1,2,4-triazolo[4,3-a]-pyrimidines and (substituted-phenyl)-1,2,4-triazolo[1,5-a]pyrimidines

• US 4,209,621 A
• Filed: 04/27/1979
• Issued: 06/24/1980
• Est. Priority Date: 04/27/1979
• Status: Expired due to Term

• Current Assignee: American Cyanamid Co (Pfizer Inc.)
• Original Assignee: American Cyanamid Co (Pfizer Inc.)
• Inventors: Dusza, John P., Albright, Jay D., Hardy, Robert A. Jr.
• Primary Examiner(s): Daus, Donald G.
• Assistant Examiner(s): Turnipseed, James H.
• Application Number:
  US06/034,060
• Time in Patent Office: 424 Days
• Field of Search: 544/263
• US Class Current: 544/263
• CPC Class Codes: C07C 45/68 by increase in the number of carbon atoms
• CPC Class Codes: C07C 49/80 containing halogen
• CPC Class Codes: C07D 231/38 Nitrogen atoms nitro radicals C07D231/16
• CPC Class Codes: C07D 239/30 Halogen atoms or nitro radicals
• CPC Class Codes: C07D 239/36 as doubly bound oxygen atom or as unsubstituted hydroxy radical
• CPC Class Codes: C07D 239/38 One sulfur atom
• CPC Class Codes: C07D 239/40 as doubly bound sulfur atom or as unsubstituted mercapto radical
• CPC Class Codes: C07D 239/42 One nitrogen atom nitro radicals C07D239/30
• CPC Class Codes: C07D 487/04 Ortho-condensed systems

Abstract

This disclosure describes substituted 1,2,4-triazolo[1,5-a]pyrimidines and substituted 1,2,4-triazolo[4,3-a]pyrimidines which possess anxiolytic activity.

Claims

1. A compound consisting of the formula:

##STR15## wherein --A═

B-- is selected from the group consisting of ##STR16## R₁ selected from the group consisting of chloro, fluoro, trifluoromethyl, lower alkoxy (C₁ -C₃) and R₂ is selected from the group consisting of hydrogen and lower alkyl (C₁ -C₃).

2. The compound in accordance with claim 1, 7-(m-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine.

3. The compound in accordance with claim 1, 2-methyl-7-(m-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine.

4. The compound in accordance with claim 1, 6-(p-fluorophenyl)-2-methyl-1,2,4-triazolo[1,5-a]pyrimidine.

5. The compound in accordance with claim 1, 6-(p-fluorophenyl)-3-methyl-1,2,4-triazolo[4,3-a]pyrimidine.

6. The compound in accordance with claim 1, 6-(o-chlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine.

7. The compound in accordance with claim 1, 7-(o-fluorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine.

8. The compound in accordance with claim 1, 6-(p-chlorophenyl)-2-methyl-1,2,4-triazolo[1,5-a]pyrimidine.

9. The compound in accordance with claim 1, 2-methyl-6-(m-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine.

10. The compound in accordance with claim 1, 3-methyl-6-(m-trifluoromethylphenyl)-1,2,4-triazolo[4,3-a]pyrimidine.

11. The compound in accordance with claim 1, 7-(m-methoxyphenyl)-1,2,4-triazolo[1,5-a]pyrimidine.

12. The compound in accordance with claim 1, 6-(m-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine.

13. The compound in accordance with claim 1, 6-(m-fluorophenyl)-2-methyl-1,2,4-triazolo[1,5-a]pyrimidine.

14. The compound in accordance with claim 1, 6-(m-chlorophenyl)-2-methyl-1,2,4-triazolo[1,5-a]pyrimidine.

15. The compound in accordance with claim 1, 6-(m-trifluoromethylphenyl)-1,2,4-triazolo[4,3-a]pyrimidine.

16. The compound in accordance with claim 1, 6-(m-chlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine.