Ciba-geigy Corporation

Rene Meier

Roland Heckendorn

Andre Gagneux

Tbe invention relates to 3H-1,2,3-triazolo[4,5-d]pyrimidine derivatives, especially substituted 3-benzyl-3H-1,2,3-triazolo[4,5-d]-pyrimidines of the general formula ##STR1## in which Ph represents a phenyl radical substituted by halogen, lower alkyl, trifluoromethyl and/or by cyano, R.sub.1 represents a free amino group or an amino group that is substituted aliphatically, cycloaliphatically, cycloaliphatically-aliphatically and/or by acyl, and R.sub.2 represents hydrogen, lower alkyl, a free amino group, or an amino group that is substituted aliphatically, cycloaliphaically, cycloaliphatically-aliphatically and/or by acyl, in free form or in form of a salt, with the proviso, that in a compound of formula I in free form, wherein R.sub.1 represents N,N-di-C.sub.1 -C.sub.6 -alkylamino in which the two N-C.sub.1 -C.sub.6 -alkyl groups may be the same or different, N-mono-C.sub.1 -C.sub.6 -alkylamino or amino, R.sub.2 is other than hydrogen and other than C.sub.1 - C.sub.6 -alkyl, if Ph represents a phenyl radical which is monosubstituted by halogen or by trifluoromethyl, and to compounds of formula I in free form wherein either Ph is o-fluorophenyl, R.sub.1 is N-mono-methylamino or amino, and R.sub.2 is hydrogen or methyl or wherein Ph is o-fluorophenyl, o-chlorophenyl or m-trifluoromethylphenyl, R.sub.1 is N,N-di-methylamino, and R.sub.2 is hydrogen or wherein Ph is m-fluorophenyl, p-fluorophenyl, o-chlorophenyl, o-trifluoromehylphenyl, m-trifluoromethylphenyl or p-trifluoromethylphenyl, R.sub.1 is N-mono-methylamino, and R.sub.2 is hydrogen. These compounds and salts can be used as pharmaceutical active ingredients and can be produced in a manner known per se.

3-benzyl-3H-1,2,3-triazolo[4,5-d]pyrimidines, compositions thereof, and

1-phenyl-lower alkyl-1H-1,2,3-triazole compounds of the formula ##STR1## in which Ph represents phenyl substituted by up to and including 3 substituents selected from lower alkyl, halogen and trifluoromethyl, alk represents lower alkylidene, and wherein either

Aralkyltriazole compounds

The present invention relates to new triazole derivatives of the formula ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, optionally esterified or etherified hydroxymethyl, formyl, optionally functionally modified carboxy, or optionally mono- or disubstituted aminomethyl, R.sub.2 represents lower alkyl, and R.sub.3 represents hydrogen or lower alkyl, whereby R.sub.2 and R.sub.3 as lower alkyl can be bound directly, or in .beta.- or .gamma.-position also by way of oxygen, sulphur or the imino radical or a lower alkylimino radical, and the rings A and B independently of each other can be unsubstituted or substituted, and to their addition salts with inorganic and organic acids, in particular the pharmaceutically acceptable acid addition salts. These new compounds possess valuable pharmacological properties. In particular they have an anticonvulsive activity and are useful for the treatment of epilepsy and of conditions of tension and of agitation. Specific embodiments are the 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(morpholinomethyl)-1H-1,2,4-triaz ole-3-carboxamide and the N,N-dimethyl-1-[2-(o-fluorobenzoyl)-4-chlorophenyl]-5-[(dimethylamino)-met hyl]-1H-1,2,4-triazole-3-carboxamide.

Triazole derivatives

The present invention relates to new triazole derivatives of the formula ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, optionally esterified or etherified hydroxymethyl, formyl, optionally functionally modified carboxy, or optionally mono- or disubstituted aminomethyl,

Compounds of the class of 6-phenyl-4H-s-triazolo[1,5-a][1,4]benzodiazepine-2-carboxamides, their 5-oxides and their pharmaceutically acceptable acid addition salts have valuable pharmacological properties and are active ingredients for therapeutic compositions. In particular, these new compounds have an anti-convulsive and anti-aggressive action and inhibit somatic reflexes. Specific embodiments are N,N-dimethyl-6-phenyl-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodiazepine-2-c arboxamide, 6-(o-fluorophenyl)-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodiazepine-2-carb oxamide, N,N-dimethyl-6-(o-fluorophenyl)-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodia zepine-2-carboxamide and N,N-dimethyl-6-(o-chlorophenyl)-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodia zepine-2-carboxamide.

Triazolyl benzophenones

Diazepine derivatives

Compounds of the class of 6-phenyl-4H-v-triazolo[1,5-a][1,4] benzodiazepines, which in the 3-position are unsubstituted or substituted, particularly by a carbamoyl group or a substituted carbamoyl group, their 5-oxides and their pharmaceutically acceptable acid addition salts have valuable pharmacological properties and are active ingredients for therapeutic compositions. In particular, these new compounds have an anticonvulsive and anti-aggressive action. Specific embodiments are N,N-dimethyl-6-phenyl-8-chloro-4H-v-triazolo [1,5-a][1,4]benzodiazepine-3-carboxamide and N,N-dimethyl-6-(o-fluorophenyl)-8-chloro-4H-v-triazolo [1,5-a][1,4]benzodiazepine-3-carboxamide.

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Buus, Switzerland

Rene Meier