Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Preparation of pyrrole sulfonic acid compound salt type

A technology of pyrrole and inorganic acid salts, which is applied in the field of chemical compounds and can solve problems such as rebound and affecting the therapeutic effect

Active Publication Date: 2018-03-20
JIANGSU CAREFREE PHARM CO LTD
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the phenomenon of acid rebound at night in PPI, it affects the therapeutic effect

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation of pyrrole sulfonic acid compound salt type

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxy)benzenesulfonyl chloride)-1H-pyrrol-3-yl)-N-methylamine fumarate

[0026] In a 100 mL one-necked bottle, add 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxy)benzenesulfonyl chloride)-1H-pyrrol-3-yl)-N- Methylamine (5.0 g, 11.6 mmol) and ethyl acetate (25 mL) were stirred and dissolved at room temperature (25°C), and fumaric acid (1.6 g, 15.20 mmol) was added to the reaction system, stirred and heated to 50 ℃, and stirred at this temperature for 2h, a solid precipitated out, the solid was filtered out, and washed with ethyl acetate (10 mL*2 times), and the obtained solid was dried in a vacuum oven (35°C) for 4 hours to obtain The white solid was 4.8 g, and the yield was 73%.

[0027] 1 HNMR (DMSO- d 6; 500 MHZ) δ (ppm) 7.6 (s, 1H), 7.48 (m, 2H), 7.28 (m, 1H), 7.20 (m, 2H), 7.09 (m, 2H), 6.83 (s, 1H) , 6.58 (s, 2H), 6.38 (s, 1H), 3.96 (m, 2H), 3.76 (s, 2H), 3.45 (m, 2H), 3.26 (s, 3H), 2.39 (s, 3H), 1.92 (m,2H).

Embodiment 2

[0029] 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxy)benzenesulfonyl chloride)-1H-pyrrol-3-yl)-N-methylamine methanesulfonate

[0030] In a 100 mL one-necked bottle, add 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxy)benzenesulfonyl chloride)-1H-pyrrol-3-yl)-N- Methylamine (5.0 g, 11.6 mmol) and ethyl acetate (25 mL) were stirred and dissolved at room temperature (25°C), methanesulfonic acid (1.3 g, 13.9 mml) was added dropwise to the reaction system, and at this temperature After stirring for 2 hours, a solid precipitated out, and the solid was filtered out and washed with ethyl acetate (8 mL*2 times), and the obtained solid was dried in a vacuum oven (35°C) for 4 hours to obtain 2.8 g of off-white solid. The rate is 45.9%.

[0031] 1 HNMR (DMSO- d 6; 500 MHZ) δ (ppm) 7.60 (s, 1H), 7.43 (m, 2H), 7.24 (m, 1H), 7.21 (m, 2H), 7.05 (m, 2H), 6.81 (s, 1H) , 6.35 (s, 1H), 3.86 (m, 2H), 3.70 (s, 2H), 3.45 (m, 2H), 3.23 (s, 3H), 2.82 (s, 3H), 2.38 (s, 3H), 1.91 (m,2H).

Embodiment 3

[0033] 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxy)benzenesulfonyl chloride)-1H-pyrrol-3-yl)-N-methylamine hydrochloride

[0034] In a 100 mL one-necked bottle, add 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxy)benzenesulfonyl chloride)-1H-pyrrol-3-yl)-N- Methylamine (5.0 g, 11.6 mmol) and ethyl acetate (30 mL) were stirred and dissolved at room temperature (25°C), and about 7 ml of ethyl acetate solution (2M) of hydrochloric acid was added dropwise to the reaction system. Stir at high temperature for 2h, no solid precipitates, dry under reduced pressure to remove the solvent to obtain a solid, disperse the resulting object in ethyl acetate (10ml), stir at room temperature for 1h, filter with suction, and wash with ethyl acetate (4ml*2). The obtained solid was dried in a vacuum oven (35°C) for 4 hours to obtain 4.8 g of off-white solid with a yield of 89.1%.

[0035] 1 HNMR (DMSO- d6; 500 MHZ) δ (ppm) 7.63 (s, 1H), 7.58 (m, 2H), 7.38 (m, 1H), 7.32 (m, 2H), 7.19 (m, 2H), 6.93 ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxy)benzenesulfonyl chloride)-1H-pyrrol-3-yl)-N-methylamine salt type. The salt type contains organic acid salt and inorganic acid salt. By mainly screening various organic acids and inorganic acids, 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxy)benzenesulfonyl chloride)-1H-pyrrol-3-yl)-N-methylamine hydrochloride and 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxy)benzenesulfonyl chloride)-1H-pyrrol-3-yl)-N-methylamine fumarate which have relatively high purities and relatively good stabilities can be obtained and can be used for treating erosive esophagitis, gastric ulcer, duodenal ulcer and helicobacter pylori, eradicating adaptation diseases and treating relevant diseases caused by hyperacidity.

Description

technical field [0001] The present invention belongs to the field of compounds, in particular to 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxy)benzenesulfonyl chloride)-1H-pyrrol-3-yl)-N - Methylamine salt forms and methods for their preparation. Background technique [0002] Gastric acid-related disease is the most common type of disease in the digestive system. It refers to a general term for a type of digestive tract disease caused by excessive gastric acid secretion or being particularly sensitive to gastric acid. The common one is gastroesophageal reflux disease. , peptic ulcer, Zollinger-Ellison syndrome and digestive system diseases caused by non-steroidal anti-inflammatory drugs. [0003] Since 1988, proton pump inhibitors represented by omeprazole have been widely used clinically to treat peptic ulcer, reflux esophagitis and Zoller-Ellison syndrome by inhibiting gastric acid secretion. Long-term clinical application has found that existing proton pump inhibitors sti...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D207/48A61P1/04A61P1/00
CPCC07D207/48A61K31/40A61P1/00A61P1/04C07C51/412C07C55/07C07C55/10C07C59/08C07C303/32C07C309/04C07C59/245C07C59/265
Inventor 苏梅金秋王伟
Owner JIANGSU CAREFREE PHARM CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com