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US 4,789,680 AGranted
Aralkyltriazole compounds
AssigneeCiba-Geigy Corporation
InventorRene Meier
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AssigneeCiba-Geigy Corporation
InventorRene Meier
Estimating the term…
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 R.sub.1 represents hydrogen, lower alkyl, lower alkoxy, amino, N-lower alkylamino, N,N-di-lower alkylamino, N-lower alkanoylamino, carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl and R.sub.2 represents carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl or R.sub.1 represents carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl and R.sub.2 represents hydrogen or lower alkyl, have anti-convulsive properties and can be used as medicaments.
A 1-phenyl-lower alkyl-1H-1,2,3-triazole compound of the formula ##STR11## 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
A method of treating a convulsive disorder in a warm blooded animal comprising administering to said animal an anticonvulsive effective amount of a compound of formula I ##STR12## wherein Ph represents phenyl substituted by up to and including three substituents selected from lower alkyl halogen and trifluoromethyl, alk represents lower alkylidene, and wherein either R.sub.1 represents hydrogen, lower alkyl, lower alkoxy, amino, N-lower alkyl or N,N-di-lower alkylamino, N-lower alkanoylamino, carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl and R.sub.2 denotes carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl or R.sub.1 represents carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl and R.sub.2 denotes hydrogen or lower alkyl, and wherein lower alkyl lower alkyl in N-lower-amino or -carbamoyl and N,N-di-lower alkylamino or -carbamoyl, lower alkoxy and lower alkylidene have up to and including 7 carbon atoms.
Dependencies are inferred from the claim text.
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Compounds containing azido groups
Halogenated unsaturated alcohols: containing only six-membered aromatic rings as cyclic parts
Not condensed with other rings: 1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
Acyclic or carbocyclic compounds
Term ended 6 Dec 2005 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
The invention relates to novel 1-phenyl-lower alkyl-1H-1,2,3-triazole compounds of the formula ##STR2## in which
Ph represents phenyl substituted by up to and including 3 substituents selected from lower alkyl, halogen and trifluormethyl, alk represents lower alkylidene,
R.sub.1 represents hydrogen, lower alkyl, lower alkoxy, amino, N-lower alkylamino, N,N-di-lower alkylamino, N-lower alkanoylamino, carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl and
The following Examples serve to illustrate the invention; temperatures are given in degrees Centigrade.
23 g (1 mol) of sodium are dissolved in 1 litre of ethyl alcohol and 101 g (1.2 mol) of cyanoacetamide are added thereto. 167.5 g (1 mol) of o-chlorobenzyl azide are added to this suspension at 40.degree.-45.degree. and the whole is heated for 2 hours under reflux. After cooling to 30.degree., 1000 ml of water are added, the precipitated product is filtered off with suction and then washed several times with warm water. After recrystallisation from dioxan and toluene, 5-amino-1-(o-chlorobenzyl)-1H-1,2,3-triazole-4-carboxamide is obtained in the form of colourless crystals having a melting point of 206.degree.-207.degree..
In analogous manner, starting from 2,6-dichlorobenzyl azide, there is obtained 5-amino-1-(2,6-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxamide having a melting point of 243.degree.-245.degree. (after crystallisation from methanol).