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Pyrrole ring containing hemifumarate as proton pump inhibitor as well as intermediate and pharmaceutical application thereof

A technology of hemi-fumarate and fumaric acid, applied in the field of medicine and biology, can solve problems such as ulcers, and achieve the effects of good stability, good gastric acid inhibition and excellent biological activity

Active Publication Date: 2015-03-25
连云港恒运药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when certain factors damage a link in the protective mechanism, gastric acid and protease may erode the self-mucosa and cause ulcer formation.

Method used

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  • Pyrrole ring containing hemifumarate as proton pump inhibitor as well as intermediate and pharmaceutical application thereof
  • Pyrrole ring containing hemifumarate as proton pump inhibitor as well as intermediate and pharmaceutical application thereof
  • Pyrrole ring containing hemifumarate as proton pump inhibitor as well as intermediate and pharmaceutical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-methyl Acetamide 10g was dissolved in a mixed solvent of isopropanol (80ml) and absolute ethanol (20ml), and 1.26g of fumaric acid was added with stirring, then heated to 50°C and refluxed for 30 minutes. Naturally cooled to room temperature, stirred for 2 hours, filtered, and dried to obtain 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl) Sulfonyl)phenoxy)-N-methylacetamide hemifumarate.

Embodiment 2

[0035] 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-methyl Acetamide 10g, dissolved in isopropanol (80ml), added fumaric acid ethanol solution (1.26g / 20ml), heated to reflux, all solids dissolved, naturally cooled to room temperature under stirring conditions, stirred for 2 hours, filtered, Drying gave 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-methyl Acetamide hemifumarate.

Embodiment 3

[0036] Example 3: 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N -Preparation of methylacetamide hemifumarate intermediate and free base

[0037]

[0038] first step

[0039] tert-Butyl((5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbonate (3.0g, 10mmol) and 3-(2-(methylamino)- Add 2-oxoethoxy)phenyl-1-sulfonyl chloride (2.64mg, 10mmol) into acetonitrile, add DIEA and stir for 2-5 hours. The temperature of the reaction solution was cooled, dilute hydrochloric acid was added to adjust the pH to 4-5, and purified water was added for crystallization to obtain compound III, 4.9 g, yield: 92.3%.

[0040] second step

[0041]Compound III (4.5 g) was dissolved in 15 mL of ethyl acetate, the temperature of the reaction liquid was cooled to 10° C. in an ice bath, hydrochloric acid gas was added, and the reaction was stirred for 1 hour. Use sodium bicarbonate to adjust pH to alkaline, wash with saturated sodium chloride solution, dry ov...

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PUM

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Abstract

The invention discloses a pyrrole ring containing hemifumarate which serves as a proton pump inhibitor as well as an intermediate and pharmaceutical application thereof, and particularly discloses a pyrrole ring containing 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-methylacetamide hemifumarate which serves as a proton pump inhibitor and has a formula (I) as shown in the specification, a method for synthesizing the same from 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-methylacetamide and fumaric acid and an preparation intermediate of the 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-methylacetamide hemifumarate. The pyrrole ring containing 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-methylacetamide hemifumarate disclosed by the invention has good stability, excellent biological activity and a good gastric acid inhibition effect.

Description

technical field [0001] The invention relates to the field of medical biology, in particular to 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)benzene Oxy)-N-methylacetamide hemifumarate and its preparation method, intermediate, pharmaceutical composition and medical application thereof. Background technique [0002] Peptic ulcer refers to the tissue damage of the gastrointestinal mucosa beyond the muscularis mucosa caused by the digestion of gastric digestive juice itself. It can occur in any part of the digestive tract, among which the stomach and duodenum are the most common, namely gastric ulcer and duodenum The etiology, clinical symptoms and treatment methods of digital ulcers are basically similar, and the definite diagnosis mainly depends on gastroscopy. Gastric ulcer is the most common type of peptic ulcer, which mainly refers to the tissue damage beyond the muscularis mucosa caused by the gastric mucosa being digested by the gastric diges...

Claims

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Application Information

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IPC IPC(8): C07D207/48A61K31/40A61P1/04
CPCC07D207/48
Inventor 余俊朱强杨宝海
Owner 连云港恒运药业有限公司
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