Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-10-20
1997-12-30
Fan, Jane
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5462737, 546194, 544124, 544131, 544364, C07D40112, A61K 3144
Patent
active
057030979
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/KR94/00098 now WO 95/23140.
TECHNICAL FIELD
The present invention relates to a novel 5-pyrrolyl-2-pyridylmethylsulfinylbenzimidazole derivative. More specifically, the present invention relates to a novel 5-pyrrolyl-2-pyridylmethylsulfinylbenzimidazole derivative represented by the following general formula (I): ##STR2## and a salt thereof, in which X represents S, SO or SO.sub.2, alkyl, --N(R.sub.7).sub.2, 1-piperidinyl, 4-morpholinyl, 4-methylpiperazin-1-yl, 1-pyrrolidinyl, --OR.sub.6, or --O(CH.sub.2).sub.m --Z, wherein C.sub.3 -C.sub.10 cycloalkyl, C.sub.2 -C.sub.5 fluoroalkyl, or phenyl or benzyl, each of which independently substituted with one or more halogen or C.sub.1 -C.sub.4 alkyl or alkoxy optionally substituted with halogen, --R.sub.9 or O(CH.sub.2).sub.r O(CH.sub.2).sub.s --OR.sub.10, wherein C.sub.1 -C.sub.5 alkyl, or when R.sub.4 and R.sub.5 together with the carbon atoms adjacent to pyridine ring form a ring, R.sub.4 and R.sub.3 or R.sub.3 and R.sub.5 represent --CH.dbd.CH--CH.dbd.CH--, --O(CH.sub.2).sub.n --, --O(CH.sub.2).sub.n O--, --CH.sub.2 (CH.sub.2).sub.n -- or --OCH.dbd.CH--, wherein n denotes an integer of 1 to 4.
The present invention also relates to a process for preparation of the compound of formula (I), as defined above, and use of the compound of formula (I) as an agent for prophylaxis and treatment of gastric and duodenal ulcers.
BACKGROUND ART
Gastric and duodenal ulcers are a gastrointestinal disease caused by various factors such as mental stress, dietary habit, intake of irritable food, and the like. The direct cause of peptic ulcers is damage to the gastric membrane due to excessive secretion of gastric acid. Accordingly, therapeutic agents which have been commonly used for treatment of the peptic ulcers includes, for example, antacids for neutralizing gastric acid, anti-pepsin agents, agents for protecting the gastric mucous membrane, anti-cholinergic agents for inhibiting gastric secretion, para-sympatholytic agents, H.sub.2 -receptor antagonists, and the like. At the present time, since it has been disclosed that antacids and CNS-acting antiulcerants provide only a unsatisfactory therapeutic effect and may cause adverse effects when they are administered for a long period, the use of H.sub.2 -receptor antagonists as agents for treating gastric and duodenal ulcers has increased.
In addition, recently imidazole (Generic name: Omeprazole) has been developed and demonstrated as a good anti-ulcer agent having a superior effect over conventional H.sub.2 -receptor antagonists such a cimetidine, famotidine, ranitidine and the like (see, U.S. Pat. Nos. 4,255,431, 4,337,257, 4,508,905, 4,758,579, British Patent No. 2,134,523, European Patent No. 0,005,129 and 0,268,956). Accordingly, Omeprazole is widely used in various types of formulations.
In view of the acting mechanism, contrary to conventional H.sub.2 -receptor antagonists, Omeprazole blocks the proton pump of H.sup.+,K.sup.+ -ATPase present in the gastric membrane to inhibit the gastric secretion. In addition, Omeprazole has also an advantage of prolonged duration in comparison with conventional antiulcerants.
Thus, the present inventors have studied for a long time to develop novel anti-ulcer agents. As a result, we have synthesized a novel compound having the general formula (I), as defined above, and then identified that the compound of formula (I) as having a superior anti-ulcer effect in comparison with Omeprazole. Thus, now we have completed the present invention.
DISCLOSURE OF INVENTION
It is an object of the present invention to provide a novel 5-pyrrolyl-2-pyridylmethylsulfinylbenzimidazole derivatives having the following general formula (I): ##STR3## and a salt thereof, in which X represents S, SO or SO.sub.2, alkyl, --N(R.sub.7).sub.2, 1-piperidinyl, 4-morpholinyl, 4-methylpiperazin-1-yl, 1-pyrrolidinyl, --OR.sub.6, or --O(CH.sub.2).sub.m --Z, wherein C.sub.3 -C.sub.10 cycloalkyl, C.sub.2 -C.sub.5 fluoroalkyl, or phenyl or benzyl, each of which independently substituted with on
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Chung Gi ju
Hong Sung Kol
Kim Dong Yeon
Kim Su Ung
Lee Yong Suk
Fan Jane
Il-Yang Pharm. Co., Ltd.
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