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1-[(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl]methanamine derivatives and their pharmaceutical compositions and uses

A sulfonyl, methyl-substituted methyl-di-deuterium methylamine technology, applied in the field of medicine, can solve problems such as poor drug metabolism, side effects, toxicity to the human body, etc., and achieve excellent pharmacodynamic performance, low toxicity, and good gastric acid secretion inhibitory activity. Effect

Active Publication Date: 2021-07-16
JIANGSU JIBEIER PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many adverse drug metabolism problems may occur during the treatment with Vonorazan, and the active metabolites produced may cause toxicity or side effects on the human body

Method used

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  • 1-[(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl]methanamine derivatives and their pharmaceutical compositions and uses
  • 1-[(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl]methanamine derivatives and their pharmaceutical compositions and uses
  • 1-[(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl]methanamine derivatives and their pharmaceutical compositions and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Preparation of 1-[5-(2-fluorophenyl)-1-(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl]-N-methyldideuteromethylamine (I-1)

[0071] Step 1: Preparation of intermediate 5-(2-fluorophenyl)-1H-pyrrole-3-dideuteriomethanol (I-1-b)

[0072]Under the protection of argon, 5-(2-fluorophenyl)-1H-pyrrole-3-carboxylic acid ethyl ester (I-1-a) (1.0g, 5.71mmol ) was dissolved in tetrahydrofuran (20mL), cooled to -78°C, a solution of lithium aluminum deuteride (0.24g, 5.71mmol) in tetrahydrofuran (20mL) was added dropwise, stirred and reacted at -78°C for 2 hours, and then added with magnesium sulfate solution The reaction was quenched, and the mixture was stirred at room temperature for 0.5 hours. Ethyl acetate was added, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. Separation and purification by silica gel column chromatography (eluent: hexane: ethyl acetate = 7:3-1:1) to obtain intermediate 5-(2-fluorophenyl)-1H-py...

Embodiment 2

[0086] Preparation of 1-[5-(2-fluorophenyl)-1-(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl]-N-methyldideuteromethylamine fumarate ( I-1a)

[0087] 0.5g of 1-[5-(2-fluorophenyl)-1-(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl]-N-methyldideuteriomethylamine (I-a) , dissolved in a mixed solvent of isopropanol (5mL) and absolute ethanol (2mL), added 0.13g of fumaric acid while stirring, then heated to 50°C and refluxed for 30 minutes, naturally cooled to room temperature while stirring, and stirred for another 2 hours , filtered, and dried to give 1-[5-(2-fluorophenyl)-1-(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl]-N-methyldideuteromethylamine rich Maleate salt (I-1a) 0.45g.

[0088] LC-MS: 348.4 (M+1).

[0089] 1 H-NMR (DMSO-d 6 )δ2.46(s,3H),6.45(s,2H),6.52(s,1H),7.07-7.15(m,1H),7.21-7.23(m,2H),7.49-7.64(m,2H) ,7.78(d,J=1.8Hz,1H),7.82-7.90(m,1H),8.56-8.57(m,1H),8.88-8.89(m,1H).

Embodiment 3

[0091] Preparation of 1-[5-(2-fluorophenyl)-1-(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl]-N-trideuteromethyldideuteromethylamine (I -2)

[0092] According to the method of Example 1, the methylamine-N,N-d2 in Example 1 was replaced by methylamine-d5, thereby preparing 1-[5-(2-fluorophenyl)-1-(pyridine-3 -yl-sulfonyl)-1H-pyrrol-3-yl]-N-trideuteromethyldideuteromethylamine (I-2).

[0093] LC-MS: 351.4 (M+1).

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Abstract

The present invention provides a 1-[(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl]methylamine derivative with the structure shown in the following formula (I), its pharmaceutical composition and application. The 1-[(pyridin-3-yl-sulfonyl)-1H-pyrrole-3-yl]methylamine derivatives provided by the present invention have good gastric acid secretion inhibitory activity and excellent pharmacodynamic properties, and lower toxicity.

Description

technical field [0001] The invention belongs to the field of medicine and provides a 1-[(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl]methanamine derivative, a pharmaceutical composition or preparation containing the compound and its Use in the preparation of medicines for treating gastric acid-related diseases. Background technique [0002] Acid-related diseases (ARDs) are a group of upper gastrointestinal diseases in which gastric acid is closely related to pathogenesis. For example: gastroesophageal reflux disease (GERD), dyspepsia, gastrointestinal ulcer, gastritis, duodenitis, Zollinger-Ellison syndrome and gastrointestinal diseases caused by non-steroidal anti-inflammatory drugs. The incidence of gastric acid-related diseases is increasing year by year worldwide. Clinically, gastric acid-related diseases are one of the most common and frequently occurring digestive system diseases. [0003] Gastric proton pump enzyme (H + , K + -ATPase) is the main target of drugs for th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12A61K31/4439A61P1/04
CPCA61K31/4439A61P1/04C07D401/12A61K45/06
Inventor 耿仲毅陈兴海
Owner JIANGSU JIBEIER PHARMA
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