1,5-Bis substituted-1,4-pentadien-3-one substituted amidino hydrazone salts and method of preparing the same

Abstract

The preparation of 1,5-bis-substituted-1,4-pentadien-3-one, substituted amidinohydrazone salts are described. They are prepared by the reaction of a 1,5-bis(substituted)-1,4-pentadiene-3-one with a substituted aminoguanidine salt. These compounds are useful as anti-malarial and anti-tubercular agents in warm-blooded animals.

I claim: 
     
       1. A pentadiene of the formula: ##STR5## wherein R 1  and R 2  may be the same or different and are selected from the group consisting of phenyl, halophenyl, carboxyphenyl, lower alkoxy (C 1  -C 4 )phenyl, diloweralkoxy (C 1  -C 4 )phenyl, biphenylyl, alkyl (C 1  -C 4 ) phenyl, dialkyl (C 2  -C 8 )phenyl, nitrophenyl, trifluoromethylphenyl, lower alkyl (C 1  -C 4 )sulfonylphenyl, lower alkyl (C 1  -C 4 )thiophenyl, methylenedioxyphenyl, cyanophenyl, sulfamylphenyl, carboloweralkoxy (C 1  -C 4 )phenyl, naphthyl, lower alkoxy (C 1  -C 4 )naphthyl and halonaphthyl; R 3  and R 4  may be the same or different and are selected from the group consisting of hydrogen, lower alkyl C 1  -C.sub. 4, phenyl and halophenyl; R 5  and R 6  are lower alkyl C 1  -C 4  and when taken together an alkylene group of 2 to 9 carbon atoms, a methyl or a phenyl alkylene group of 2 to 4 carbon atoms, a dimethyl or a diphenyl alkylene group of 2 to 4 carbon atoms.Iadd., or a 1,2-cyclohexylene group, .Iaddend.and R 7  is hydrogen or lower alkyl C 1  -C 4 , and non-toxic acid salts thereof. 
     
     
       2. The pentadiene in accordance with claim 1, 1,5-bis(p-chlorophenyl)-1,4-pentadiene-3-one 4,5,6,7-tetrahydro-1H-1,3-diazepin-2-ylhydrazone hydrochloride. 
     
     
       3. The pentadiene in accordance with claim 1, 1,5-bis(p-chlorophenyl)-1,4-pentadien-3-one 1,4,5,6-tetrahydropyrimidin-2-ylhydrazone hydrochloride. 
     
     
       4. The pentadiene in accordance with claim 1, 1,5-bis(p-methoxyphenyl)-1,4-pentadien-3-one 2-imidazolin-2-ylhydrazone hydrobromide. 
     
     
       5. The pentadiene in accordance with claim 1, 1,5-bis(p-tolyl)-1,4 -pentadien-3-one 2-imidazolin-2-ylhydrazone hydrobromide. 
     
     
       6. The pentadiene in accordance with claim 1, 1,5-bis(p-chlorophenyl)-1,4-pentadien-3-one N-methylamidinohydrazone hydroiodide. 
     
     
       7. The pentadiene in accordance with claim 1, 1,5-bis(p-chlorophenyl)-1,4-pentadien-3-one 2-imidazolin-2-ylhydrazone hydrochloride. 
     
     
       8. The pentadiene in accordance with claim 1, 1,5-bis(4-chlorophenyl)-1,4-pentadien-3-one amidinohydrazone hydrochloride. 
     
     
       9. The pentadiene in accordance with claim 1, 1,5-bis(p-methylthiophenyl)-1,4-pentadien-3-one 2-imidazolin-2-ylhydrazone hydrobromide. 
     
     
       10. A pentadiene of the formula: ##STR6## wherein R 8  and R 9  are hydrogen or methyl; X is halo or hydrogen and Y is lower alkyl C 1  -C 4  or hydrogen or a non-toxic acid salt thereof. 
     
     
       11. The pentadiene in accordance with claim 10, 1,5-bis(m-tolyl)-1,4-pentadiene-3-one 1,4,5,6-tetrahydropyrimidin-2-ylhydrazone hydrochloride. 
     
     
       12. The pentadiene in accordance with claim 10, 1,5-bis(p-chlorophenyl)-1,4-pentadiene-3-one 5,5-dimethyl-1,4,5,6-tetrahydropyrimidin-2-ylhydrazone hydrobromide. .Iadd. 13. The pentadiene in accordance with claim 1, 1,5-bis(p-chlorophenyl)-1,4-pentadiene-3-one 3α ,4,5,6,7,7a-hexahydrobenzimidazol-2-yl-hydrazone hydrochloride. .Iaddend..Iadd. 14. The pentadiene in accordance with claim 1, 1,5-bis(p-chlorophenyl)-1,4-pentadien-3-one 3α ,4,5,6,7,7a-hexahydrobenzimidazol-2-yl-hydrazone hydrobromide. .Iaddend. .Iadd. 15. The pentadiene in accordance with claim 1, 1,5-bis(p-chlorophenyl)-1,4-pentadiene-3-one 3a,4,5,6,7,7a-hexahydrobenzimidazol-2-yl-hydrazone. .Iaddend.