Substituted arylthioalkylthiopyridines

Details Substituted arylthioalkylthiopyridines Substituted arylthioalkylthiopyridines

1995-12-20

1998-06-30

Fan, Jane

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514269, 514274, 5462737, 5462721, 5462717, 5462711, 5462697, 5462724, 5462691, 5462687, 546256, 544315, 544319, C07D40112, A61K 3104

Patent

active

057734518

DESCRIPTION:

BRIEF SUMMARY
FIELD OF USE OF THE INVENTION

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


KNOWN TECHNICAL BACKGROUND

European Patent Application 150 586 discloses 2-(pyridylmethylthio- and -sulfinyl)benzimidazoles which can be substituted in the 4-position of the pyridine part of the molecule by, inter alia, alkylthio or arylthio radicals. A long-lasting inhibition of the secretion of gastric acid is reported for the compounds described. International Patent Application WO89/03830 states that the same compounds and other structurally similar compounds are suitable for treatment of osteoporosis. International Patent Application WO92/12976 describes 2-(pyridylmethylthio- and -sulfinyl)benzimidazoles which are substituted in a particular manner and are said to be active against Helicobacter bacteria and for which it is furthermore disclosed that they are said to be suitable for the prevention and treatment of a whole range of diseases of the stomach.


SUMMARY OF THE INVENTION

The invention relates to compounds of formula I (see FIG. 1A), in which 1-4C-alkoxy which is completely or predominantly substituted by fluorine, or chlorodifluoromethoxy or 2-chloro-1,1,2-trifluoroethoxy, or, together with R3, is 1-2C-alkylenedioxy which, if desired, is completely or partly substituted by fluorine, or chlorotrifluoroethylenedioxy, substituted by fluorine, or chlorodifluoromethoxy or 2-chloro-1,1,2-trifluoroethoxy or, together with R2, is 1-2C-alkylenedioxy which, if desired, is completely or partly substituted by fluorine, or chlorotrifluoroethylenedioxy, chosen from the group consisting of benzene, furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiazoline, isothiazole, imidazole, imidazoline, pyrazole, triazole, tetrazole, thiadiazole, oxadiazole, pyridine, pyridine N-oxide, pyrimidine and benzimidazole, carboxyl, 1-4C-alkoxycarbonyl, guanidino, 1-4C-alkyl which is substituted by R10, or --N(R11)R12, in which both bonded, are a piperidino or morpholino radical,


BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1A is the formula of final products, whereas FIG. 1B, FIG. 1C and FIG. 1D are formulae of intermediates for preparing that final product.


DETAILS

1-4C-alkyl is a straight-chain or branched alkyl radical 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 is a radical which contains one of the abovementioned 1-4C-alkyl radicals, in addition to the oxygen atom. Examples which may be mentioned are the methoxy and the ethoxy radicals.
Halogen in the context of the present invention is bromine, chlorine and fluorine.
Examples which may be mentioned of 1-4C-alkoxy which is completely 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, if desired, is completely or partly 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--CF.sub.2 --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 (--O--CF.sub.2 --CHF--O--) radicals.
If R2 and R3 together are 1-2C-alkylenedioxy which, if desired, is completely or partly substituted by fluorine, or chlorotrifluoroethylenedioxy, the substituents R2 and R3 are bonded to the benzo part of the benzimidazole ring in adjacent positions--preferably to positions 5 and 6.
The group --S(O)q-- is bonded to a carbon atom of the cyclic or bicyclic radical R6 in question, so that examples of radicals R6 which may be mentioned are the radicals: phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,

REFERENCES:
patent: 4560693 (1985-12-01), Rainer

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