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A kind of hydroxy-substituted benzene sulfonate of dabigatran etexilate and its preparation method and use

A technology of hydroxybenzenesulfonate and amino, which is applied in the field of medicine, can solve the problems of not clearly providing examples, etc., and achieve the effect of simple and easy preparation method, good stability and high yield

Inactive Publication Date: 2016-12-21
SICHUAN HAISCO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned patent also protects the physiologically acceptable salt of dabigatran etexilate, but does not clearly provide relevant examples

Method used

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  • A kind of hydroxy-substituted benzene sulfonate of dabigatran etexilate and its preparation method and use
  • A kind of hydroxy-substituted benzene sulfonate of dabigatran etexilate and its preparation method and use
  • A kind of hydroxy-substituted benzene sulfonate of dabigatran etexilate and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1: the synthesis of dabigatran etexilate 2,5-dihydroxybenzenesulfonate

[0056] Add dabigatran etexilate (tetrahydrate) (28.5g, 0.045mol) and 2,5-dihydroxybenzenesulfonic acid (10.3g, 0.054mol) into a reaction flask containing ethyl acetate (300ml), respectively, Control the temperature at 30°C, stir to dissolve, and obtain a clear solution. Concentrate the reaction solution to 1 / 2 volume, let it stand, cool, and crystals are precipitated, which is 2,5-dihydroxybenzenesulfonate of dabigatran etexilate. The crystals were suspended in water (300ml) and stirred at 30°C for 4 hours. Filter and dry the filter cake under vacuum at 40°C. Weight: 33.8g, yield: 92%. The crystal form corresponding to the product is named Form A.

[0057] The following is the structural characterization data of dabigatran etexilate 2,5-dihydroxybenzenesulfonate:

[0058] m.p.163.5-164.5℃.

[0059] IR(KBr) v :3280(N-H),3174(O-H),2980(-CH 3 ), 2933 (-CH 2 -),2856(-CH 3 ), 1759, ...

Embodiment 2

[0064] Embodiment 2: the synthesis of dabigatran etexilate 2,5-dihydroxybenzenesulfonate

[0065] Add dabigatran etexilate (tetrahydrate) (28.5g, 0.045mol) and 2,5-dihydroxybenzenesulfonic acid (10.3g, 0.054mol) into a reaction flask containing ethyl acetate (500ml), respectively, Control the temperature at 10°C, stir to dissolve, and obtain a clear solution. Concentrate the reaction solution to 1 / 2 volume, let it stand, cool, and crystals are precipitated, which is 2,5-dihydroxybenzenesulfonate of dabigatran etexilate. The crystals were suspended in water (300ml) and stirred at 30°C for 4 hours. Filter and dry the filter cake under vacuum at 40°C. Weight: 30.1 g, yield: 82%.

[0066] The characterization results of the product are the same as in Example 1.

Embodiment 3

[0067] Embodiment 3: the synthesis of dabigatran etexilate 2,5-dihydroxybenzenesulfonate

[0068] Add dabigatran etexilate (tetrahydrate) (28.5g, 0.045mol) and 2,5-dihydroxybenzenesulfonic acid (10.3g, 0.054mol) into the reaction flask containing ethyl acetate (200ml) respectively , heated to 60°C, stirred to dissolve, and a clear solution was obtained. Concentrate the reaction solution to 1 / 2 volume, let it stand, cool, and crystals are precipitated, which is 2,5-dihydroxybenzenesulfonate of dabigatran etexilate. The crystals were suspended in water (300ml) and stirred at 30°C for 4 hours. Filter and dry the filter cake under vacuum at 40°C. Weight: 31.3 g, yield: 85%.

[0069] The characterization results of the product are the same as in Example 1.

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Abstract

The invention discloses a hydroxyl substituted benzene sulfonate of dabigatran etexilate and a preparation method and a usage thereof. The preparation method comprises: respectively adding dabigatran etexilate and hydroxyl substituted benzenesulfonic acid into an organic solvent, stirring and dissolving to obtain a clear solution; and reacting under a certain temperature, concentrating, stewing, separating out crystals, and filtering to obtain the hydroxyl substituted benzene sulfonate of dabigatran etexilate. The hydroxyl substituted benzene sulfonate of dabigatran etexilate provided by the invention has good stability; the provided preparation method is simple, convenient, feasible, stable and reliable, and a crystal form suitable for medicinal can be obtained; and the obtained product is good in quality and high in yield.

Description

technical field [0001] The present invention relates to the field of medicine, in particular to a hydroxy-substituted benzenesulfonate of dabigatran etexilate (dabigatranetexilate) with anticoagulant effect, its preparation method and pharmaceutical composition with the compound as an active ingredient, and their use in The preparation is used in the prevention or treatment of diseases caused by thrombus or embolism. Background technique [0002] In recent years, the incidence of cardiovascular and cerebrovascular diseases has been on the rise, which has seriously endangered human health. Among them, related diseases caused by thrombus or embolism are the primary factors leading to disability and death. The prevention and treatment of thrombosis and its complications has become an important issue faced by the world medical community. Anticoagulant drugs can effectively improve and prevent cardiovascular and cerebrovascular diseases caused by thrombus, and reduce mortality. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12A61K31/4439A61P7/02
CPCC07D401/12
Inventor 邹永陈洪陈大峰杜全胜袁道义李岳晏菊芳袁辛娅
Owner SICHUAN HAISCO PHARMA CO LTD