[3-Substituted-5-[(di-methylamino)methyl]-4H-1,2,4-triazol- 4-yl

Details [3-Substituted-5-[(di-methylamino)methyl]-4H-1,2,4-triazol- 4-yl [3-Substituted-5-[(di-methylamino)methyl]-4H-1,2,4-triazol- 4-yl

1975-06-06

1977-03-01

Rollins, Alton D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602471M, 2602471E, 2602472R, 26029369, 42424856, 424267, 424269, C07D24908, C07D40106, C07D40306, C07D41306

Patent

active

040101770

ABSTRACT:
Compounds of the formula I: ##STR1## wherein R.sub.1 is hydroxymethyl, or -CH.sub.2 NR.sub.6 R.sub.7, in which R.sub.6 is -CH.sub.2 -C.tbd.CH, -CH.sub.2 -CH=CH.sub.2, ##STR2## or alkyl of 1 to 3 carbon atoms, inclusive; R.sub.7 is hydrogen or alkyl of 1 to 3 carbon atoms, or together ##STR3## is pyrrolidino, piperidino or morpholino; wherein R.sub.2 is hydrogen, chlorine or fluorine; wherein R.sub.3 is hydrogen, or fluorine if R.sub.2 is fluorine; wherein R.sub.4 is hydrogen, fluorine, chlorine, bromine, nitro, or trifluoromethyl; and wherein R.sub.5 is hydrogen, methyl or ethyl. These compounds, except those in which R.sub.7 is hydrogen, are produced by heating a compound of formula II: ##STR4## wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are defined as hereinabove, and wherein R'.sub.1 is the same as R.sub.1 except that in defining R'.sub.1,R.sub.7 may not be hydrogen, with aqueous formaldehyde in formic acid solution at reflux temperature (about 100.degree. C.).
Compounds in which R.sub.7 are hydrogen require steps further shown in the specification.
The compounds of formula I and their pharmacologically acceptable acid addition salts thereof have tranquilizing, anti-anxiety and anti-convulsant activity useful for the treatment of animals and man.

REFERENCES:
patent: 3856792 (1974-12-01), Hester
patent: 3879413 (1975-04-01), Hester
patent: 3907821 (1975-09-01), Gall

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