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Novel benzimidazoles compounds

A technology of benzimidazoles and compounds, applied in the field of bisbenzimidazoles

Inactive Publication Date: 2009-06-10
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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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0172] Example 1: 5,5'-bis-[2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylthio]-1H-benzimidazole] (Compound 1 ) preparation

[0173]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, the obtained oil was added with water to precipitate a solid, 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, 3H), 2.30(s, 3H), 2....

Embodiment 2

[0174] Example 2: Preparation of 5,5'-bis-[2-[(3,4-dimethoxypyridin-2-yl)methylthio]-1H-benzimidazole] (compound 2)

[0175] 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

[0176] Example 3: 5,5'-bis-[2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-1H- The preparation of benzimidazole] (compound 3)

[0177] 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%. 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

The invention relates to benzimidazole compounds capable of suppressing gastric acid secretion, resisting helicobacter pylori and exerting targeted inhibition of activity gastric cancer cells of the formula on the right. Structurally, the compounds have two benzimidazole active functional groups which can be combined with two cysteine residues in a H<+>, K<+>-adenosine triphosphatase (ATP) monomer or two cysteine residues in an oligomer after being activated by the gastric acid in vivo to inhibit the activity of the H<+>, K<+>-ATP. The compounds can selectively inhibit the activity of Hp. A, B, L, R1 and n are defined in the claim 1.

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 Applications(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
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