Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1999-01-08
2000-12-05
Morris, Patricia L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
540485, 5462684, 548250, 548251, 548254, C07D24904, C07D24906, C07D40304, C07D40704, C07D40904
Patent
active
061569070
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1-Substituted 1H-1,2,3-triazoles are widely used industrially. For example, the European Patent Applications with the publication nos. 114347 A2 (EP 114347) and 199262 A1 (EP 199262) describe appropriate triazoles having anticonvulsive action. Compounds of this type are prepared, for example, by reaction of an arylalkyl azide with an alkyne derivative followed, if desired, by subsequent chemical conversions. Actual embodiments can be seen, for example, from the working examples of EP 199262 and EP 114347.
It is the aim of a variety of efforts to develop for pharmaceutical active ingredients production processes which are easy to manipulate and economical, result in high yields and ecologically have as few objections as possible.
The invention relates to a novel process for the preparation of 1-substituted 1H-1,2,3-triazole-4-carbonitriles, to novel intermediates and to their use for the production, for example, of pharmaceutical active ingredients.
DESCRIPTION OF THE INVENTION
The invention relates on the one hand to a novel preparation of compounds of the formula (I) ##STR2## in which R.sub.1 is an aromatic or heteroaromatic radical, aromatic-aliphatic or heteroaromatic-aliphatic radical, a heterocyclic radical, a cycloaliphatic radical, a cycloaliphatic-aliphatic radical or an aliphatic radical, and on the other hand to novel compounds of the formula (I).
An aromatic radical is, for example, mono- or bicyclic carbocyclic aryl which is unsubstituted or mono- or polysubstituted, such as di- or trisubstituted, for example phenyl, naphthyl or biphenylyl.
A heteroaromatic radical is, for example, mono- bi- or tricyclic heteroaryl, for example a 5- or 6-membered and monocyclic radical, which contains up to and including four identical or different heteroatoms, such as oxygen, sulfur or nitrogen, preferably 1, 2, 3 or 4 nitrogen atoms, an oxygen or a sulfur atom.
Suitable 5-membered heteroaryl radicals are, for example, monoaza-, diaza-, triaza-, tetraaza-, monooxa- or monothiacyclic heteroaryl radicals, such as pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furyl and thienyl, while possible 6-membered radicals are, in particular, pyridyl radicals.
In an aromatic-aliphatic radical , the aromatic moiety, for example, has the meaning which is indicated above for aromatic radicals, while an aliphatic radical is, for example, lower alkyl, lower alkenyl or lower alkynyl. An aromatic-aliphatic radical is, for example, phenyl-lower alkyl, phenyl-lower alkenyl or phenyl-lower alkynyl, furthermore naphthyl-lower alkyl.
In a heteroaromatic-aliphatic radical, the heteroaromatic moiety, for example, h as the meaning which is indicated above for heteroaromatic radicals, while an aliphatic radical is, for example, lower alkyl, lower alkenyl or lower alkynyl. A heteroaromatic-aliphatic radical is, for example, pyridyl-lower alkyl.
A heterocyclic radical is, for example, a 5- or 6-membered monocyclic or a bi- or tricyclic radical which contains up to and including four identical or different heteroatoms, such as nitrogen, oxygen or sulfur, preferably one, two or three nitrogen atoms, a sulfur and an oxygen atom. It is also possible for one or two benzene rings to be fused to an appropriate heterocyclic radical. A heterocyclic radical of this type, for example, is a partially hydrogenated 2-oxobenzazepine, such as 2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine.
A cycloaliphatic radical is, for example, cycloalkyl or furthermore cycloalkenyl, which in each case are unsubstituted or mono- or polysubstituted, e.g. disubstituted, e.g. by lower alkyl, carboxyl or lower alkoxycarbonyl.
A cycloaliphatic-aliphatic radical is, for example, cycloalkyl-lower alkyl or furthermore cycloalkenyl-lower alkyl.
An aliphatic radical is, for example, lower alkyl, lower alkenyl or furthermore lower alkynyl, which are unsubstituted or in each case mono-or polysubstituted, e.g. disubstituted, e.g. by halogen, by free or esterified or amidated carboxyl, such as lower alkoxycarbonyl, carbamoyl or mono- or di-lower al
REFERENCES:
patent: 4789680 (1988-12-01), Meier
Database WPI Abstract XP002043428 (1981).
WPIDS Abstract 84-190298 (1984).
A. Derdour et al., Bull. De La Societe Chim. De France, pp. 69-78 (1990) *.
R.G.Micetich, Canadian Jour. of Chem., vol. 47, pp. 3753-3755 (1970) *.
Borovian Joseph J.
Morris Patricia L.
Novartis AG
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