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Process for preparing Torasemide intermediate and its analogue

A compound and reaction technology, which is applied in the field of preparation of torasemide intermediates and their analogues, can solve the problems of low overall yield, high energy consumption of distillation, time-consuming and laborious, etc., and achieve simple operation, high yield and high product quality. good purity effect

Active Publication Date: 2009-11-04
南京海辰药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Steam distillation consumes a lot of energy and is time-consuming
The resulting product often contains a small amount of copper ions, which requires repeated acid-base purification to obtain the desired product, and the total yield is low, about 30% to 60%.

Method used

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  • Process for preparing Torasemide intermediate and its analogue
  • Process for preparing Torasemide intermediate and its analogue
  • Process for preparing Torasemide intermediate and its analogue

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis of 3-sulfamoyl-4-(3'-methylphenyl)aminopyridine

[0023] In a 1000mL three-necked flask equipped with a mechanical stirrer, a condenser, and a thermometer, add (3-sulfamoyl-4-chloro)pyridine 20g (0.104mol), m-aminotoluene 27.8g (0.26mol) and n-butanol 400g, stir, heat and control the inner temperature to 95-105°C for 5h. The solvent was recovered under reduced pressure. While stirring, add water while hot. Cool down to 30°C and add 8% sodium hydroxide to dissolve it (pH12). Cool down to 20°C and extract the layers with 120g of isopropyl ether, and then extract the water layer with 60g x 2 times. The water layer was decolorized with activated carbon for 15 minutes and filtered, the filter cake was washed with a small amount of water, and the washed filtrates were combined, cooled to 5-10°C, adjusted to pH 7 with 10% hydrochloric acid solution, and stirred for 30 minutes. After filtering, the filter cake was washed three times with ice water, and dried at 80...

Embodiment 2

[0025] Synthesis of 3-sulfamoyl-4-(3'-methylphenyl)aminopyridine

[0026] In a 1000mL three-necked flask equipped with a mechanical stirrer, a condenser, and a thermometer, add (3-sulfamoyl-4-chloro)pyridine 20g (0.104mol), m-aminotoluene 27.8g (0.26mol) and N, 400 g of N-dimethylformamide was stirred, heated and controlled at an internal temperature of 95-105°C for 5 hours. The solvent was recovered under reduced pressure. While stirring, add water while hot. Cool down to 30°C and add 8% sodium hydroxide to dissolve it (pH12). Cool down to 20°C and extract the layers with 120g of isopropyl ether, and then extract the water layer with 60g x 2 times. The water layer was decolorized with activated carbon for 15 minutes and filtered, the filter cake was washed with a small amount of water, and the washed filtrates were combined, cooled to 5-10°C, adjusted to pH 7 with 10% hydrochloric acid solution, and stirred for 30 minutes. After filtering, the filter cake was washed three...

Embodiment 3

[0028] Synthesis of 3-sulfamoyl-4-(3'-trifluoromethylphenyl)aminopyridine

[0029] In a 1000mL three-neck flask equipped with a mechanical stirrer, a condenser, and a thermometer, add (3-sulfamoyl-4-chloro)pyridine 20g (0.104mol), m-aminotrifluorotoluene 41.9g (0.26mol) and DMSO 400g, stirred, heated and controlled internal temperature 95-105°C for 7h. The solvent was recovered under reduced pressure. While stirring, add water while hot. Cool down to 30°C and add 8% sodium hydroxide to dissolve it (pH12). Cool down to 20°C and extract the layers with 120g of isopropyl ether, and then extract the water layer with 60g x 2 times. The water layer was decolorized with activated carbon for 15 minutes and filtered, the filter cake was washed with a small amount of water, and the washed filtrates were combined, cooled to 5-10°C, adjusted to pH 7 with 10% hydrochloric acid solution, and stirred for 30 minutes. After filtering, the filter cake was washed three times with ice water, ...

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Abstract

The invention relates to the field of medicinal chemistry, in particular to a preparation method of a torasemide intermediate and analogues thereof. By selecting an appropriate solvent, reacting at a relatively mild temperature, without using copper powder, avoiding difficulty in purification, and obtaining a high-yield and high-purity product, the preparation method of the invention is suitable for large-scale production processes.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of a torasemide intermediate and analogues thereof. Background technique [0002] Torsemide is a new fast-acting, potent, long-acting loop diuretic, and is disclosed as 1-isopropyl-3-[(m-tolylamino-3-pyridyl) in DE2516025 (Example 71) Sulfonyl]urea. In addition to its diuretic properties, it also has antihypertensive properties. [0003] The synthesis of torasemide, torasemide intermediates and torasemide derivatives is described in the following references: DE2516025; Delarge, J. Ann Pharm. Fr. 31, 467-474 (1973); Delarge, Mem .Acad.R.Med.Belg.47(3), 131-210(1974); Delarge, J.Ann Pharm.Fr.36, 369-380(1978); Iyakuhin Kenkyu, 25(9), 734-750 (1994); EP618209; US2516025; US6674794; US4244950 are all reported. The preparation method generally adopted is as follows: [0004] [0005] CN01806834.0 discloses a method for preparing IV from III; CN2004100787...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/74
Inventor 曹于平蒋金元冯明声郑文艳
Owner 南京海辰药业股份有限公司
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