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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
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  • 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

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  • 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 ...

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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

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Application Information

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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
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