Piperazinothiopyridines for the control of Helicobacter bacteria

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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514303, 514318, 544360, 544362, 544370, 546188, 546193, A01N 4360, C07D40100, C07D40300

Patent

active

059227206

DESCRIPTION:

BRIEF SUMMARY
FIELD OF APPLICATION OF THE INVENTION

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


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, inter alia, by alkylthio or arylthio radicals. A long-lasting inhibition of gastric acid secretion is indicated for the compounds described. --International Patent Application WO89/03830 describes that the same and also other compounds of similar structure ought to be suitable for the treatment of osteoporosis. --International Patent Application WO92/12976 describes 2-(pyridylmethylthio- or sulfinyl)benzimidazoles substituted in a certain manner, which ought to be active against Helicobacter bacteria and for which it is furthermore disclosed that they ought to be suitable for the prevention and treatment of a whole series of disorders of the stomach. --International Patent Application WO93/24480 describes other 2-(pyridylmethylthio- or -sulfinyl)benzimidazoles substituted in a certain manner, which ought to be active against Helicobacter bacteria.


DESCRIPTION OF THE INVENTION

The inventions relates to compounds of the formula I (see attached formula sheet I), in which 2-4C-alkenylcarbonyl, halogen-1-4C-alkylcarbonyl, N(R14)R15-1-4C-alkylcarbonyl, di-1-4C-alkylcarbamoyl or 1-4C-alkylsulfonyl, selected from the group consisting of benzene, furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiazoline, isothiazole, imidazole, imidazoline, pyrazole, triazole, tetrazole, thiadiazole, thiadiazole-1-oxide, oxadiazole, pyridine, pyridine-N-oxide, pyrimidine, triazine, pyridone, benzimidazole, imidazopyridine, benzothiazole and benzoxazole, guanidino, carboxyl, 1-4C-alkoxycarbonyl, R10-substituted 1-4C-alkyl or --N(R11)R12, trifluoromethyl, where bonded, are a piperidino or morpholino radical, bonded, are a piperidino or morpholino radical, v is the number 0, O, S or SO.sub.2, v is the number 1 and u is the number 0.
1-4C-Alkyl is 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 is a radical which, beside the oxygen atom, contains one of the abovementioned 1-4C-alkyl radicals. Examples which may be mentioned are the methoxy and the ethoxy radicals.
Halogen within the meaning of the present invention is bromine, chlorine and, in particular, fluorine.
1-4C-Alkylcarbonyl is a radical which, beside the carbonyl group, contains one of the abovementioned 1-4C-alkyl radicals. An example which may be mentioned is the acetyl radical.
2-4C-Alkenylcarbonyl is a radical which, beside the carbonyl group, contains a 2-4C-alkenyl radical, for example a propenyl radical or a butenyl radical. An example which may be mentioned is the acryloyl radical.
Halogen-1-4C-alkylcarbonyl is a radical which, beside the carbonyl group, contains a halogen-substituted 1-4C-alkyl radical. An example which may be mentioned is the .gamma.-chlorobutyryl radical.
N(R14)R15-1-4C-Alkylcarbonyl is a radical which, beside the carbonyl group, contains an --N(R14)R15-substituted 1-4C-alkyl radical. An example which may be mentioned is the 3-dimethylaminopropionyl radical.
Di-1-4C-alkylcarbamoyl is a radical which, beside the carbonyl group, contains a di-1-4C-alkylamino radical. The di-1-4C-alkylamino radical is an amino radical which is substituted by two of the above-mentioned 1-4C-alkyl radicals which are identical or different. Examples which may be mentioned are the dimethylamino, the diethylamino and the diisopropylamino radicals. Di-1-4C-alkylcarbamoyl radicals which may be mentioned are, for example, the dimethylcarbamoyl and the diethylcarbamoyl radicals.
1-4C-Alkylsulfonyl is a radical which, beside the sulfonyl group (--SO.sub.2 --) contains one of the above-mentioned 1-4C-alkyl radicals. A

REFERENCES:
patent: 5504082 (1996-04-01), Kawakita et al.

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