# US 5,703,097 A · 5-pyrrolyl-2-pyridylmethylsulfinyl benzimidazole derivatives

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- Number: US 5,703,097 A
- Document ID: US5703097A
- Status: Granted
- Kind: A
- Application number: 08/537,846
- Filed: 1995-10-20
- Granted: 1997-12-30
- Earliest claimed: 1994-02-28
- Assignees: Il-Yang Pharm. Co., Ltd
- Inventors: Su Ung Kim; Dong Yeon Kim; Gi ju Chung; Sung Kol Hong; Sung Jun Park; Sang Hoon Nam; Yong Suk Lee
- Web page: https://patentgrep.com/patent/US5703097A

## CPC

- C07D 401/14: containing three or more hetero rings
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to a novel compound 5-pyrrolyl-2-pyridylmethylsulfinylbenzimidazole derivative having general formula (I) and its salt, ##STR1## wherein all variables are as defined in the specification. The present invention also relates to a process for preparation of the compound of formula (I), as defined above, and its use as an anti-ulcer agent.

## Claims

### Claim 1

A compound having the following formula (I), ##STR19## or a salt thereof, in which X represents S, SO or SO.sub.2,
R.sub.1 and R.sub.2 independently from each other represent hydrogen or alkyl,
R.sub.3 represents hydrogen, C.sub.1 -C.sub.8 alkyl, --SR.sub.6, --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
R.sub.6 represents C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.2 -C.sub.5 fluoroalkyl, or phenyl or benzyl, each of which independently is substituted with one or more halogen or C.sub.1 -C.sub.4 alkyl or alkoxy optionally substituted with halogen,
R.sub.7 represents hydrogen or C.sub.1 -C.sub.5 alkyl,
Z represents a group --O(CH.sub.2).sub.p --OR.sub.8, --O(CH.sub.2).sub.q --R.sub.9 or --O(CH.sub.2).sub.r O(CH.sub.2).sub.s --OR.sub.10, wherein
p and q independently from each other denote an integer of 1 to 3,
r and s independently from each other denote an integer of 1 to 5,
R.sub.8 represents hydrogen, lower alkyl, aryl or aralkyl,
R.sub.9 represents hydrogen alkoxycarbonyl, or aryl, and
R10 represents hydrogen or lower alkyl,
m represents an integer of 2 to 10, and
R.sub.4 and R.sub.5 independently from each other represent hydrogen or C.sub.1 -C.sub.5 alkyl.

### Claim 2 (depends on 1)

The compound of formula (I) as defined in claim 1, wherein
X represents S, SO or SO.sub.2,
R.sub.1 and R.sub.2 independently from each other represent hydrogen or methyl,
R.sub.3 represents hydrogen, C.sub.1 -C.sub.8 alkyl, --SR.sub.6, --N(R.sub.7).sub.2, 1-piperidinyl, 4-morpholinyl, 4-methylpiperzain-1-yl, 1-pyrrolidinyl, --OR.sub.6, or --O(CH.sub.2).sub.m --Z, wherein
R.sub.6 represents C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.10 cycloalkyl optionally substituted with C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 fluoroalkyl having 3 to 8 fluorine atoms, or phenyl or benzyl, each of which independently is substituted with one or more halogen or C.sub.1 -C.sub.4 alkyl or alkoxy optionally substituted with halogen,
R.sub.7 represents hydrogen or C.sub.1 -C.sub.4 alkyl,
Z represents a group --O(CH.sub.2).sub.p --OR.sub.8, --O(CH.sub.2).sub.q --R.sub.9 or --O(CH.sub.2).sub.r O(CH.sub.2).sub.s --OR.sub.10, wherein
p and q independently from each other denote an integer of 1 to 3,
r and s independently from each other denote an integer of 1 to 5,
R.sub.8 represents hydrogen, lower alkyl, aryl or aralkyl,
R.sub.9 represents hydrogen alkoxycarbonyl, or aryl, and
R.sub.10 represents hydrogen or lower alkyl,
m represents an integer of 2 to 10, and R.sub.4 and R.sub.5 independently from each other represent hydrogen or C.sub.1 -C.sub.5 alkyl.

### Claim 3 (depends on 2)

The compound of formula (I) as defined in claim 2, wherein
X represents S, SO or SO.sub.2,
R.sub.1 and R.sub.2 independently from each other represent hydrogen or methyl,
R.sub.3 represents hydrogen, methyl, methoxy, ethoxy, 2,2,2-trifluoroethoxy or 3,3,3,2,2-pentafluoropropoxy,
R.sub.4 represents hydrogen or methyl, and
R.sub.5 represents hydrogen, methyl or ethyl.

### Claim 4 (depends on 1)

The compound of formula (I) as defined in claim 1, wherein
X represents SO,
R.sub.1 and R.sub.2 independently from each other represent hydrogen,
R.sub.3 represents methoxy or ethoxy, and
R.sub.4 and R.sub.5 independently from each other represent hydrogen, methyl or ethyl.

### Claim 5 (depends on 1)

An anti-ulcer composition comprising an effective amount of a compound having the following formula (I) as an active ingredient: ##STR20## in which X, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are defined as described in claim 1 for the compound of formula (I), together with a pharmaceutically acceptable carrier, adjuvant or excipient therefor.