Novel pyridine derivative having anti-helicobacter pylori activity

An anti-Helicobacter pylori and derivative technology, applied in antibacterial drugs, medical preparations with non-active ingredients, medical preparations containing active ingredients, etc. The record and enlightenment of bacterial action, etc., to achieve the effect of excellent antibacterial action

Inactive Publication Date: 2009-04-01
LINK GENOMICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the compounds 2-[{4-(2-hydroxyethoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (comparative compound 1) and 2- [{4-(3-Hydroxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (comparative compound 2) is described in Patent Document 9 and Example 26 and the compounds useful as anti-ulcer agents in Example 34, but there is no record of experimental data about their anti-ulcer effect, and in addition, there is no record or revelation about the effect on Helicobacter pylori

Method used

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  • Novel pyridine derivative having anti-helicobacter pylori activity
  • Novel pyridine derivative having anti-helicobacter pylori activity
  • Novel pyridine derivative having anti-helicobacter pylori activity

Examples

Experimental program
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Embodiment

[0076] Hereinafter, methods for producing raw material compounds used in the present invention, comparative compounds, and compounds of the present invention will be specifically described by way of Synthesis Examples and Examples. In addition, HPLC analysis was performed under the following conditions.

[0077] Column Inertsil ODS-3 150mm×4.6mmID

[0078] Eluent 0.05M KH 2 PO 4 / acetonitrile=50 / 50(v / v)

[0079] Flow rate 1.0ml / min

[0080] Column temperature 40°C

[0081] Injection volume 2μL

[0082] Detection wavelength 254nm

Synthetic example 1

[0083] Synthesis example 1: 4-(5-hydroxypentyloxy)-2,3-lutidine-N-oxide

[0084] Under nitrogen flow, 140 ml of 1,5-pentanediol was added on a silicone oil bath, and 4.6 g (0.2 mol, 2.0 equivalents) of sodium metal was added while stirring. Next, the silicone oil bath was heated and reacted at 100° C. for 1 hour. After adding 15.8 g (1.0 mol, 1.0 equivalent) of 4-chloro-2,3-lutidine-N-oxide to the obtained reaction liquid, the temperature was raised to 120° C. and reacted for 2 hours. After cooling the reaction solution, it was concentrated and dried under reduced pressure to obtain 53.3 g of a concentrated residue, which was purified through a silica gel column to obtain 25.0 g of 4-(5-hydroxypentyloxy)-2,3-lutidine-N-oxide things.

Synthetic example 2

[0085] Synthesis Example 2: 4-(5-Hydroxypentyloxy)-2-acetoxymethyl-3-methylpyridine

[0086] Add 153.1g (1.5mol, 15 equivalents) of acetic anhydride to 24.5g (0.1mol, 1.0 equivalents) of 4-(5-hydroxypentyloxy)-2,3-lutidine-N-oxide, at 100 °C for 5 hours. Acetic anhydride was distilled off to obtain a concentrated residue, which was purified through a silica gel column to obtain 12.1 g of 4-(5-hydroxypentyloxy)-2-acetoxymethyl-3-picoline (yield 39.2%).

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Abstract

The object is to provide an excellent pharmaceutical having an anti-Helicobacter pylori activity. Disclosed is a novel pyridine derivative represented by the general formula (I) or a pharmaceutically acceptable salt thereof, which has a potent antibacterial activity against H. pyroli (Helicobacter pyroli): (I) wherein R represents a linear or branched hydroxyalkyl group having 5 to 10 carbon atoms. Examples of the disease which can be prevented / treated by administration of a pharmaceutical agent comprising the compound include gastritis, gastric ulcer, duodenal ulcer, gastric MALT lymphoma, gastric hyperplastic polyp, development of gastric cancer after endoscopic resection of the early stage of gastric cancer and the like.

Description

technical field [0001] The present invention relates to a novel pyridine derivative having an excellent anti-Helicobacter pylori effect, a method for producing the same, and a pharmaceutical composition containing the compound. Background technique [0002] Gastritis, gastric ulcer, and duodenal ulcer are diseases that are complicated and intertwined with factors such as stress, genetic factors, and living habits. In recent years, Helicobacter pylori (H. pylori) has attracted attention as one of the pathogenic factors. Since Warren and Marshall successfully isolated and cultured spiral-shaped bacteria from gastric biopsy specimens in 1983, the relationship between gastritis, gastric ulcer, duodenal ulcer and gastric cancer and the bacteria has been actively studied. As a result, the infection rate of Helicobacter pylori was about 83% in chronic gastritis, about 69% in gastric ulcer, and about 92% in duodenal ulcer, compared with the positive rate of about 4% in healthy stom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12A61P1/18A61K31/4439A61P31/04A61K45/00A61P35/00A61K47/36A61P43/00A61P1/04
CPCA61K9/0019C07D401/12A61K9/4858A61K9/0095A61K9/2018A61K9/1623A61K47/36A61K31/4439A61K45/06A61P1/00A61P1/04A61P1/18A61P31/00A61P31/04A61P35/00A61P43/00A61K45/00
Inventor 伊藤正春山本雅一
Owner LINK GENOMICS
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