Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1989-12-05
1992-11-10
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544 9, A61K 3154, C07D28520
Patent
active
051623170
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INDUSTRIAL APPLICATION
This invention relates to a pyridinium salt having an antiulcer effect.
BACKGROUND OF THE INVENTION
It is believed that peptic ulcers such as gastric and duodenal ulcers are formed when aggressive factors such as acid and pepsin and protective factors such as mucosa-resistance, mucus, blood and duodenal control are out of balance and thus autolysis is induced.
Peptic ulcers are to be medically treated as a rule. Therefore medicinal treatments therefor have been attempted so far. Examples of the antiulcer drugs which are commonly used today include cimetidine and ranitidine, each based on the histamine H.sub.2 receptor antagonism. However it has been reported that these drugs are accompanied by some side effects, for example, an antiandrogenic effect or an inhibitive effect on hepatic metabolic enzyme activity.
Under these circumstances, it is recently suggested that an inhibitor for H.sup.+ --K.sup.+ ATPase, which specifically occurs in gastric wall cells, would serve as an excellent inhibitor for acid secretion.
SUMMARY OF THE INVENTION
The invention provides a new pyridiniuim salt having the formula (I): ##STR2## in which R3 and R4 each are hydrogen or a lower alkyl, m is an integer of 2 to 10, Z is --OR5 or --0--(CH2)n--OR6, R5 is hydrogen, a lower alkyl, an aryl or an aryl alkyl, R6 is hydrogen, a lower alkyl, an aryl or an arylalkyl, n is an integer of 1 to 3, X is a pharmacologically acceptable anion, K is (1) --S--or (2) --S--S--R, R is an organic group which may have a substituent, J is a benzoimidazole ring which may have a substituent(s), --shows a bond thereby to connect with the nitrogen of the benzimidazole or no bond, provided that (1) when K is --S--, J is a group having the formula: ##STR3## in which R1 and R2 each are hydrogen, a lower alkyl, a lower alkoxy, a halogenated lower alkyl, a lower alkoxycarbonyl, carboxyl or a halogen, (2) when K is --S--S--R, J is a group having the formula: ##STR4## and X does not exist.
The pyridinium salt as defined above includes two embodiments. One is a sulphenamide derivative having the formula (I a) and the other is a pyridinium salt having the formula (I-b): ##STR5##
It is preferred that in the formula (I), (I-a) and (I-b), R3 is methyl and R4 is hydrogen. Moreover Z is preferably --OR5. m is preferably 3. R5 is preferably methyl.
The invention provides a pharmacological composition which comprises a pharmacologically effective amount of the pyridinium salt having the formula (I) and a pharmacologically acceptable carrier.
The invention will be explained in view of the embodiments (I-a) and (I-b).
Compound (I-a)
The target compound of the present invention is a sulphenamide derivative represented by the following general formula (I): ##STR6## wherein R.sup.1 and R.sup.2 may be the same or different from each other and each represents a hydrogen atom, a lower alkyl, a lower alkoxy, a halogenated lower alkyl, a lower alkoxycarbonyl or a carboxyl group or a halogen atom; represents a hydrogen atom or a lower alkyl, an aryl or an arylalkyl group, or a group represented by the formula --O--(CH.sub.2).sub.n --O--R.sup.6, wherein n is an integer of 1 to 3 and R.sup.6 represents a hydrogen atom or a lower alkyl, an aryl or an arylalkyl group; and
Accordingly, it is an object of the present invention to provide a novel sulphenamide derivative which is effective as an antiulcer drug, a process for the preparation of the same and a novel antiulcer drug containing the same.
Examples of the lower alkyl groups R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 of the compound (I) of the present invention which is defined above include straight-chain and branched alkyl groups carrying one to six carbon atoms, such as methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, 1-methylpropyl, ter-butyl, n-pentyl, 1-ethylpropyl, isoamyl and n-hexyl groups. Among these groups, methyl and ethyl groups are the most preferable.
The terms "lower alkoxy group", "halogenated lower alkyl group" and "lower alkoxycarbonyl group" use
REFERENCES:
patent: 4636499 (1987-01-01), Brandstrom et al.
patent: 4769456 (1988-09-01), Nohara et al.
Fujimoto Masatoshi
Fujisaki Hideaki
Kaneko Toshihiko
Miyazawa Shuhei
Murakami Manabu
Esai Co., Ltd.
Grumbling Matthew V.
Shah Mukund J.
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