Substituted heteroarylaklylthiopyridines for controlling helicob

Details Substituted heteroarylaklylthiopyridines for controlling helicob Substituted heteroarylaklylthiopyridines for controlling helicob

1995-08-15

1996-12-24

Ivy, C. Warren

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514333, 5462734, A61K 31415, A61K 3144, C07D21370, C07D23342

Patent

active

055873898

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP94/00393, filed 11 Feb., 1996.


FIELD OF THE INVENTION

The invention relates to compounds which are to be used in the pharmaceutical industry as active ingredients for the preparation of drug products.


KNOWN TECHNICAL BACKGROUND

European Patent Application 150,586 discloses 2-(pyridylmethylthio- or sulfinyl)benzimidazoles which can be substituted in the pyridine moiety of the molecule in the 4-position by, inter alia, alkylthio or arylthio radicals. It is mentioned that the above-described compounds have a sustained inhibitory action on the secretion of gastric acid. International Patent Application WO 89/03830 describes that the same compounds, and others having a similar structure, are suitable for treating osteoporosis. International Patent Application WO 92/12976 describes 2-(pyridylmethylthio- or sulfinyl)benzimidazoles which are substituted in a certain manner, which are active against Helicobacter bacteria and which are furthermore disclosed as being suitable for preventing and treating a wide range of stomach disorders.


DESCRIPTION OF THE INVENTION

The invention relates to compounds of the formula I (see appended formula sheet) in which predominantly fluorine-substituted 1-4C-alkoxy, chlorodifluoromethoxy, 2-chloro-1,1,2-trifluoroethoxy, or, if desired, together with R3 1-2C-alkylenedioxy which is fully or partially substituted by fluorine, or chlorotrifluoroethylenedioxy, fluorine, or is chlorodifluoromethoxy, 2-chloro-1,1,2-trifluoroethoxy, or, if desired, together with R2 1-2C-alkylenedioxy which is fully or partially substituted by fluorine, or chlorotrifluoroethylenedioxy, pyrrole, oxazole, isoxazole, thiazole, isothiazole, imidazole, pyrazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, 1,3,4-thiadiazole, 1,2,4-thiadiazole, pyrimidine and pyridine, each o#which is substituted by R8 and R9, R7 is hydrogen, 1-4C-alkyl or 1-4C-alkoxy, which is substituted by R10, or --N(R11)R12, bonded represent a piperidino or morpholino radical,
1-4C-Alkyl represents straight-chain or branched alkyl radicals having 1 to 4 carbon atoms. Examples which may be mentioned are the butyl, isobutyl, sec-butyl, tert-butyl, propyl, isopropyl, ethyl and methyl radicals.
1-4C-Alkoxy represents a radical which, in addition to the oxygen atom, contains one of the above-mentioned 1-4C-alkyl radicals. Examples which may be mentioned are the methoxy and ethoxy radicals.
Halogen for the purposes of the invention is bromine, chlorine and fluorine.
Examples which may be mentioned of 1-4C-alkoxy which is fully or predominantly substituted by fluorine are the 1,2,2-trifluoroethoxy, the 2,2,3,3,3-pentafluoropropoxy, the perfluoroethoxy and, in particular, the 1,1,2,2-tetrafluoroethoxy, the trifluoromethoxy, the 2,2,2-trifluoroethoxy and the difluoromethoxy radicals.
Examples which may be mentioned of 1-2C-alkylenedioxy which is optionally fully or partially substituted by fluorine are the methylenedioxy(--O--CH.sub.2 --O--), the ethylenedioxy(--O--CH.sub.2 --CH.sub.2 --O--), the 1,1-difluoroethylenedioxy(--O--CF2--CH.sub.2 --O--), the 1,1,2,2-tetrafluoroethylenedioxy(--O--CF.sub.2 --CF.sub.2 --O--) and, in particular, the difluoromethylenedioxy(--O--CF.sub.2 --O--) and the 1,1,2-trifluoroethylenedioxy radicals (--O--CF.sub.2 -CHF--O--).
If R2 and R3 together are 1-2C-alkylenedioxy which is optionally fully or partially substituted by fluorine, or are chlorotrifluoroethylenedioxy, then the substituents R2 and R3 are bonded on the benzo moiety of the benzimidaizole ring in adjacent positions, preferably in the 5- and 6- positions.
The heterocycles R6 can be bonded to the radical --C.sub.m H.sub.2m --via any conceivable position, so that examples of radicals R6 which may be mentioned are the following: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1-pyrazolyl, 3

REFERENCES:
patent: 4628098 (1986-12-01), Nohara
patent: 5045552 (1991-09-01), Souda
patent: 5504082 (1996-04-01), Kawakita

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