Back to results
US 4,791,114 AGranted
2-Benzimidazolylalkylthio (or -sulfinyl or -sulfonyl) derivatives, their preparation and their application as medicinal products
Assignee501 Laboratorios Del, Dr. Esteve
InventorsJordi F. Constansa, Augusto C. Pinol, Juan P. Corominas
Life of this patent
Estimating the term…
Abstract
The present invention relates to new benzimidazole derivatives, to the process for preparing them and also to their application as medicinal products. The 2-alkylbenzimidazole derivatives according to the present invention correspond to the general formula I ##STR1## and also their therapeutically acceptable salts, in which the substituents are as defined in the specification.
Claims6
2-Alkylbenzimidazole derivatives corresponding to the formula:
- ##STR24## and their pharmaceutically acceptable salts in which formula:
- X denotes a nitrogen atom (N), or a carbon atom linked to another radical R.sub.8 (C-R.sub.8);
- Y denotes a nitrogen atom (N) or an N-oxide group (N.fwdarw.O);
- Z denotes a sulfur atom (S), a sulfinyl group (S.fwdarw.O) or a sulfonyl group (O.rarw.S.fwdarw.O);
- R.sub.1 and R.sub.2, which may be identical or different, denote a hydrogen atom, a halogen, a linear or branched C.sub.1 to C.sub.4 lower alkyl radical, a nitro group (NO.sub.2), a trifluoromethyl group (CF.sub.3), a C.sub.1 to C.sub.4 alkoxy or alkylthio radical, a carboxyl radical (COOH), a C.sub.1 to C.sub.4 carboxyalkyl radical or a C.sub.1 to C.sub.4 alkanoyl or aryloyl radical ##STR25## R.sub.3 denotes a hydrogen atom, a C.sub.1 to C.sub.4 lower alkyl radical or a carbonyl radical linked to another radical R.sub.10 ##STR26## R.sub.4 denotes a hydrogen atom or a C.sub.1 to C.sub.4 lower alkyl radical;
- R.sub.5 denotes a hydrogen atom, a methyl radical, a hydroxy radical or a C.sub.1 to C.sub.4 alkoxy radical;
- R.sub.6 denotes a hydrogen atom, a methyl radical, a nitro radical (NO.sub.2) or a C.sub.1 to C.sub.4 alkoxy radical;
- R.sub.7 denotes a hydrogen atom, a C.sub.1 to C.sub.4 lower alkyl radical or a C.sub.1 to C.sub.4 alkoxy radical;
- R.sub.8 denotes a hydrogen atom or a methyl radical;
- R.sub.9 denotes a C.sub.1 to C.sub.4 lower alkyl radical, a C.sub.3 to C.sub.6 cycloalkyl radical or an aryl radical, and
- R.sub.10 denotes a C.sub.1 to C.sub.4 lower alkyl radical or a C.sub.1 to C.sub.4 alkoxy or aryloxy or arylalkoxy radical,
- wherein said aryl groups are single ring hydrocarbons;
- with the exception, however, of the compound of formula I in which:
- X denotes CH,
- Y denotes N,
- Z denotes S, and
- R.sub.1 to R.sub.7 denote H.
14 more elements
A 2-Alkylbenzimidazole derivative selected from the group consisting of:
- 2-(2-benzimidazolylmethylthio)pyrimidine;
- 2-(2-benzimidazolylmethylthio)-4-hydroxy-6-(n-propyl)pyrimidine;
- 2-(benzimidazolymethylthio)-4,6-dimethylpyrimidine;
- 2-(5-nitro-2-pyridylthiomethyl)benzimidazole;
- 5-methyl-2-(2-pyridylthiomethyl)benzimidazole;
- 5,6-dimethyl-2-(2-pyridylthiomethyl)benzimidazole;
- 2-(1-oxido-2-pyridylthiomethyl)benzimidazole;
- 5-chloro-2-(2-pyridylthiomethyl)benzimidazole;
- 5-trifluoromethyl-2-(2-pyridylthiomethyl)benzimidazole;
- 5-benzoyl-2-(2-pyridylthiomethyl)benzimidazole;
- 5-methoxy-2-(2-pyridylthiomethyl)benzimidazole;
- 2-[2-pyridylthio-(methyl)-methyl]benzimidazole;
- 5-benzoyl-2-(3,5-dimethyl-2-pyridylthiomethyl)benzimidazole;
- 5-benzoyl-2-(3-methyl-2-pyridylthiomethyl)benzimidazole;
- 2-(3-methyl-2-pyridylthiomethyl)benzimidazole;
- 2-(4-methyl-2-pyridylthiomethyl)benzimidazole;
- 5-trifluoromethyl-2-(4-methyl-2-pyridylthiomethyl)benzimidazole;
- 5-carboxymethyl-2-(4-methyl-2-pyridylthiomethyl)benzimidazole;
- 5-carboxymethyl-2-(2-pyridylthiomethyl)benzimidazole;
- 5-benzoyl-2-(4-methyl-2-pyridylthiomethyl)benzimidazole;
- 5-methoxy-2-(4-methyl-2-pyridylthiomethyl)bezimidazole;
- 5-acetyl-2-(4-methyl-2-pyridylthiomethyl)benzimidazole;
- 5-methyl-2-(4-methyl-2-pyridylthiomethyl)benzimidazole;
- 5,6-dimethyl-2-(4-methyl-2-pyridylthiomethyl)benzimidazole;
- 5-chloro-2-(4-methyl-2-pyridylthiomethyl)benzimidazole;
- 5-benzoyl-2-(2-pyridylsulfinylmethyl)benzimidazole;
- 2-(2-pyridylsulfinylmethyl)benzimidazole;
- 2-(5-nitro-2-pyridylsulfinylmethyl)benzimidazole;
- 5-methyl-2-(pyridylsulfinylmethyl)benzimidazole;
- 5,6-dimethyl-2-(2-pyridylsulfinylmethyl)benzimidazole;
- 5-chloro-2-(2-pyridylsulfinylmethyl)benzimidazole;
- 2-(2-benzimidazolylmethylsulfinyl)-4,6-dimethylpyrimidine;
- 5-trifluoromethyl-2-(2-pyridylsulfinylmethyl)benzimidazole;
- 5-methoxy-2-(2-pyridylsulfinylmethyl)benzimidazole;
- erythro-2-[2-pyridylsulfinyl(methyl)methyl]benzimidazole;
- threo-2-[2-pyridylsulfinyl(methyl)methyl]benzimidazole;
- 2-(1-oxido-2-pyridylsulfinylmethyl)benzimidazole;
- 2-(2-benzimidazolylmethylsulfinyl)pyrimidine;
- 5-benzoyl-2-(3,5-dimethyl-2-pyridylsulfinylmethyl)benzimidazole;
- 5-benzoyl-2-(3-methyl-2-pyridylsulfinylmethyl)benzimidazole;
- 2-(3-methyl-2-pyridylsulfinylmethyl)benzimidazole;
- 5-benzoyl-2-(4-methyl-2-pyridylsulfinylmethyl)benzimidazole;
- 5-carboxymethyl-2-(2-pyridylsulfinylmethyl)benzimidazole;
- 2-(4-methyl-2-pyridylsulfinylmethyl)benzimidazole;
- 5-trifluoromethyl-2-(4-methyl-2-pyridylsulfinylmethyl)benzimidazole;
- 5-carboxymethyl-2-(4-methyl-2-pyridylsulfinylmethyl)benzimidazole;
- 5-methoxy-2-(4-methyl-2-pyridylsulfinylmethyl)benzimidazole;
- 5-acetyl-2-(4-methyl-2-pyridylsulfinylmethyl)benzimidazole;
- 5-methyl-2-(4-methyl-2-pyridylsulfinylmethyl)benzimidazole;
- 5,6-dimethyl-2-(4-methyl-2-pyridylsulfinylmethyl)benzimidazole;
- 5-chloro-2-(4-methyl-2-pyridylsulfinylmethyl)benzimidazole;
- 5-chloro-2-(2-pyridylsulfonylmethyl)benzimidazole;
- 2-(2-pyridylsulfonylmethyl)benzimidazole;
- 5-methyl-2-(2-pyridylsulfonylmethyl)benzimidazole;
- 5,6-dimethyl-2-(2-pyridylsulfonylmethyl)benzimidazole;
- 2-[2-pyridylsulfonyl(methyl)methyl]benzimidazole;
- 5-nitro-2-(2-pyridylsulfinylmethyl)benzimidazole;
- 5-benzoyl-1-methyl-2-(2-pyridylsulfinylmethyl)benzimidazole;
- 6-benzoyl-1-methyl-2-(2-pyridylsulfinylmethyl)benzimidazole;
- 5-benzoyl-1-carboxyethyl-2-(2-pyridylsulfinylmethyl)benzimidazole;
- 6-benzoyl-1-carboxyethyl-2-(2-pyridylsulfinylmethyl)benzimidazole;
- 1-ethyl-2-(2-pyridylsulfinylmethyl)benzimidazole;
- and pharmaceutically acceptable salts thereof.
60 more elements
Dependencies are inferred from the claim text.