2-Substituted phenyl-s-triazolo[5,1-a] isoquinoline compounds

Abstract

A new process for preparing s-triazolo[5,1-a]-isoquinoline derivatives of the formula ##STR1## wherein A represents the group --CH 2 --CH 2 -- or --CH═CH--; R is selected from hydrogen, amino, lower alkylamino, di-lower alkylamino, acylamino, diacylamino, ureido, thioureido, carbethoxythioureido, benzoylthioureido, sulfhydryl, lower alkyl, trifluoromethyl, phenyl, substituted phenyl, pyridyl, methylpyridyl and dimethylpyridyl; and R 1 and R 2 each independently represents hydrogen or lower alkoxy, by condensation of a 2-amino-3,4-dihydro-1(2H)-isoquinolinone with an imidolyl, cyanamide, cyanic or thiocyanic derivative. New compounds of the formula I wherein A represents the group --CH 2 --CH 2 -- or --CH═CH--, R has the same meaning as above with the exclusion of hydrogen, methyl, phenyl, and trifluoromethyl, R 1 and R 2 have the same meaning as above, with the proviso that when A represents the group --CH═CH--, R cannot be tolyl or pyridyl. The new compounds and some of the intermediates of the process are active as antiinflammatories, CNS depressants and anti-fertility agents.

What is claimed is: 
     
       1. A compound of the formula ##STR7## wherein A represents the group --CH 2  --CH 2  -- or --CH═CH--; and wherein R is substituted phenyl of the formula ##STR8## wherein one of the substituents R 3  and R 4  is located in the 3- or 4-position of the phenyl ring, and represents a lower alkoxy, lower alkenyloxy, lower alkynyloxy, fluoro, chloro, bromo, trifluoromethyl, hydroxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, benzyloxy, nitro or dimethylamino group and the other represents hydrogen, methoxy, fluoro, chloro or bromo; or R 3  and R 4  taken together represent a methylenedioxy group.   
     
     
       2. A compound as claimed in claim 1 wherein R is substituted phenyl of the formula ##STR9## wherein one of R 3  and R 4  is located in the 3- or 4-position of the phenyl ring and represents methoxy, ethoxy, propoxy, isopropoxy, allyloxy, propargyloxy, fluoro, chloro or bromo and the other represents hydrogen. 
     
     
       3. The compound of claim 1 which is 2-(m-methoxyphenyl)-s-triazolo[5,1-a]isoquinoline. 
     
     
       4. The compound of claim 1 which is 2-(m-methoxyphenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline. 
     
     
       5. The compound of claim 1 which is 2-(m-ethoxyphenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline. 
     
     
       6. The compound of claim 1 which is 2-(m-propoxyphenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline. 
     
     
       7. The compound of claim 1 which is 2-(p-chlorophenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline. 
     
     
       8. The compound of claim 1 which is 2-(m-allyloxyphenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline. 
     
     
       9. The compound of claim 1 which is 2-(m-propargyloxyphenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline. 
     
     
       10. The compound of claim 1 which is 2-(m-chlorophenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline. 
     
     
       11. The compound of claim 1 which is 2-(m-isopropoxyphenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline. 
     
     
       12. The compound of claim 1 which is 2-(p-fluorophenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline. 
     
     
       13. A method for preventing littering in an impregnated female animal which comprises administering to said animal an effective amount of a compound of the following formula ##STR10## wherein R is substituted phenyl of the formula ##STR11## wherein one of the substituents R 3  and R 4  is located in the 3- or 4-position of the phenyl ring, and represents a lower alkoxy, lower alkenyloxy, lower alkynyloxy, fluoro, chloro, bromo, trifluoromethyl, hydroxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, benzyloxy, nitro or dimethylamino group and the other represents hydrogen, methoxy, fluoro, chloro or bromo; or R 3  and R 4  taken together represent a methylenedioxy group; and the symbol A represents the group --CH 2  --CH 2  -- or --CH═CH--. 
     
     
       14. A pharmaceutical composition for preventing littering in impregnated female animals comprising a pharmaceutical carrier and as the active ingredient an effective amount of a compound of the following formula ##STR12## wherein R is substituted phenyl of the formula ##STR13## wherein one of the substituents R 3  and R 4  is located in the 3- or 4-position of the phenyl ring, and represents a lower alkoxy, lower alkenyloxy, lower alkynyloxy, fluoro, chloro, bromo, trifluoromethyl, hydroxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, benzyloxy, nitro or dimethylamino group and the other represents hydrogen methoxy, fluoro, chloro or bromo; or R 3  and R 4  taken together represent a methylenedioxy group; and the symbol A represents the group --CH 2  --CH 2  -- or --CH═CH--.