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Novel benzimidazoles compounds

A kind of technology of benzimidazole and benzimidazole ring, applied in the field of medicine

Inactive Publication Date: 2013-06-19
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The objective response rate of traditional chemotherapy drugs is only 24%-40%

Method used

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  • Novel benzimidazoles compounds
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  • Novel benzimidazoles compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0173] Example 1: 5,5'-bis-[2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylthio]-1H-benzimidazole] (Compound 1 ) preparation

[0174]Add 5,5'-bis-(2-mercapto-1H-benzimidazole) (1.0 g), absolute ethanol (15 ml), sodium hydroxide (0.84 g) in water (20 ml) to the reaction flask in sequence , stirred at room temperature for 30 minutes, and the solids were completely dissolved. 2-Chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride (1.5 g) was added, and the mixture was refluxed for 2 hours. The solvent was distilled off under reduced pressure, and the resulting oily product was added with water to precipitate a solid, and the pH was adjusted to 6 with glacial acetic acid, the solid was filtered off, dried, and purified by column chromatography (chloroform:methanol=90:1) to obtain 1.6 g of compound 1, with a yield of 80 %. 1 H-NMR (300MHz, DMSO-d 6 , ppm): 12.68 (br s, 1H), 8.19 (s, 1H), 7.67 (s, 1H), 7.50 (d, J=8.3, 1H), 7.42 (dd, J=8.3, J=1.5, 1H ), 4.71(s, 2H), 3.72(s, 3...

Embodiment 2

[0175] Example 2: Preparation of 5,5'-bis-[2-[(3,4-dimethoxypyridin-2-yl)methylthio]-1H-benzimidazole] (compound 2)

[0176] Using the method of Example 1, 5,5'-bis-(2-mercapto-1H-benzimidazole) (1.0 g) and 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (1.5 g) reaction to obtain 1.8 g of compound 2, 89%. 1 H-NMR (300MHz, DMSO-d 6 , ppm): 12.68 (s, 1H), 8.17 (d, J=5.7, 1H), 7.40-7.70 (m, 3H), 7.09 (d, J=5.7, 1H), 4.69 (s, 2H), 3.89 (s,3H), 3.82(s,3H).

Embodiment 3

[0177] Example 3: 5,5'-bis-[2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-1H- The preparation of benzimidazole] (compound 3)

[0178] Using the method of Example 1, 5,5'-bis-(2-mercapto-1H-benzimidazole) (1.0 g) and 2-chloromethyl-3-methyl-4-(2,2,2- Trifluoroethoxy)pyridine hydrochloride (1.9 g) was reacted to obtain 1.9 g of compound 3, 80%.

[0179] 1 H-NMR (300MHz, DMSO-d 6 , ppm): 12.68 (s, 1H), 8.31 (d, J=5.7, 1H), 7.40-7.80 (m, 3H), 7.09 (d, J=5.7, 1H), 4.90 (q, J=8.7, 2H), 4.75(s, 2H), 2.26(s, 3H).

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Abstract

New benzimidazole compounds of the following formula (I) which have activities of inhibiting gastric acid secretion, resistingHelicobacter pylori (Hp) and treating gastric cancer, wherein A, B, L, R1 and n are defined as claim 1. The compounds have two functional groups of benzimidazole,which may combine with the cysteine residues in the H+, K+-ATP enzyme monomer or oligomer to inhibit the activity of H+, K+-ATP enzyme after being activated by gastric acid in vivo. The compounds are selective inhibitor of Hp.

Description

Field of invention: [0001] The invention belongs to the technical field of medicine, and in particular relates to a bisbenzimidazole compound with activities of inhibiting gastric acid secretion, anti-helicobacter pylori and inhibiting gastric cancer. Background technique: [0002] Proton pump inhibitors have the ability to inhibit gastric H + , K + -ATPase activity, can effectively inhibit gastric acid secretion, has been widely used in the treatment of peptic ulcer and related diseases caused by excessive gastric acid secretion, mainly including: gastric and duodenal ulcer, heartburn, reflux esophagitis , erosive esophagitis, non-ulcer dyspepsia, Helicobacter pylori infection, laryngitis, etc. [0003] At present, many patent documents have reported benzimidazole derivatives that can inhibit gastric acid secretion, mainly US4045563, 4255431, 4628098, 4686230, 4758579, 4965269, 5021433, 5430042, 5708017, 6093734, 6559167, 6897227 and so on. Studies have shown that benzim...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14A61K31/4439A61P1/04A61P35/00
CPCC07D401/14A61P1/04A61P35/00
Inventor 程卯生王庆河杨彦辉聂翰李云巍
Owner SHENYANG PHARMA UNIVERSITY