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Novel processes for preparing torsemide intermediate

A technology of compound and general formula, which is applied in the new preparation of torasemide intermediate pyridine and the new preparation field of torasemide, which can solve the problem of unsuitable for large-scale manufacturing process, low yield and high yield of torasemide low level problem

Inactive Publication Date: 2005-05-25
TEVA PHARMA IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Under these conditions, torasemide is produced in low yield and is sequestered by a high percentage of impurities, necessitating additional purification steps
These methods suffer from low yields and high variability, making them unsuitable for large-scale manufacturing processes

Method used

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  • Novel processes for preparing torsemide intermediate
  • Novel processes for preparing torsemide intermediate
  • Novel processes for preparing torsemide intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Synthesis of (3-sulfamoyl-4-chloro)pyridine

[0059] In a 100-ml three-necked flask equipped with a magnetic stirrer, condenser, thermometer, and dropping funnel, (3-sulfonylchloro-4-chloro)pyridine (10 g, 1 equiv, 46.7 mmol) was suspended in MTBE at room temperature (30ml). 25% ammonium hydroxide solution (13.5 ml, 2.13 eq.) was added dropwise to the suspension at such a rate that the temperature rose to about 22°C to about 26°C and the temperature was maintained until all the ammonium hydroxide was added. The suspension was then cooled to room temperature and stirred for 1 hour. The pH of the suspension was adjusted to 8±0.1 by adding a few drops of 25% ammonium hydroxide solution. The suspension was filtered and washed with water (2 x 10ml) and the wet product (-8g) was dried at 40°C under 1 mm Hg vacuum. 6.7 g of (3-sulfamoyl-4-chloro)pyridine were isolated in a yield of 74.4%.

Embodiment 2

[0061] Synthesis of torasemide

[0062] Add acetonitrile (15ml), 3-sulfamoyl-4-(3'-methylphenyl)aminopyridine (5g) and triethylamine ( TEA) (5.3ml). 1.87 ml of isopropyl isocyanate was added dropwise within 10 minutes, and the whole mixture was stirred at 40±2°C to dissolve completely. The mixture was cooled to room temperature and stirred for another 2 hours. The pH of the mixture was adjusted to 4.3 while raising the temperature to about 35°C. The mixture was recooled to room temperature, filtered and rinsed with a mixture of acetonitrile:water (1:1) (10 ml). The wet crude product was triturated in acetonitrile:water mixture (5:1, 13ml) at 60°C for half an hour, filtered and rinsed with acetonitrile:water (5:1) mixture (2x7ml). The milled product was then dried at 50° C. under high vacuum (3 mmHg) for 6 hours to yield 5.4 g of crude torasemide (81.5% crude yield).

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Abstract

The present invention relates to a new method for synthesizing torasemide and a new method for synthesizing an intermediate (3-sulfonyl chloride-4-chloro)pyridine for synthesizing torasemide.

Description

[0001] Cross-referencing entries for related inventions [0002] This application claims the benefit of provisional application 60 / 190650, filed March 20, 2000, and provisional application 60 / 211510, filed June 14, 2000, both of which are incorporated herein by reference. field of invention [0003] The invention relates to a new preparation method of torasemide intermediate (3-sulfamoyl-4-chloro)pyridine. The present invention relates to a new preparation method of torasemide. Background of the invention [0004] 1-Isopropyl-3-[(4-m-tolylamino-3-pyridyl)sulfonyl]urea with the following chemical structure under the trademark DEMADEX® [0005] [0006] It is FDA-approved for the treatment of high blood pressure and edema associated with congestive heart failure, kidney disease, or liver disease. The U.S. Food and Drug Administration has approved the generic name of the compound as torsemide, but the compound is also known as "torasemide" in the prior art. Torsemide is a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/61C07D213/71A61K31/44A61P7/10A61P9/04A61P9/12C07D213/74
CPCC07D213/74A61P7/10A61P9/04A61P9/12C07D213/71C07D213/61A61K31/44
Inventor M·科尔多瓦
Owner TEVA PHARMA IND LTD
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