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Ticagrelor impurity, preparation method and application thereof

A technology of ticagrelor and impurities, applied in the field of drug synthesis

Pending Publication Date: 2018-03-09
ZEIN BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are no relevant reports on impurity 7, impurity 8 and their directional synthesis methods

Method used

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  • Ticagrelor impurity, preparation method and application thereof
  • Ticagrelor impurity, preparation method and application thereof
  • Ticagrelor impurity, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Example 1 Preparation of ticagrelor impurity 7

[0061]

[0062] 1. Preparation of Impurity 7 Intermediate 1

[0063] 4.70g (12.79mmol) 2-[[(3aR,4S,6R,6aS)-6aminotetrahydro-2,2-dimethyl-4Hcyclopenta1,3-dioxolane- 4-yl]oxy]-ethanol-L-tartrate (SM1), 5.0 g (11.63 mmol) 2-({(3aR,4S,6R,6aS)-6-[7-chloro-5-(propylmercapto )-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyltetrahydro-3aH-cyclopentadieno[d][1 ,3] Dioxolane-4-yl}oxy)ethanol (B) was sequentially added to a 100ml three-necked flask, followed by 43ml of dichloromethane and 7.7ml of N,N-diisopropylethylamine (46.52mmol ), reacted in a 30°C water bath for 24h. After the reaction is over, add 30ml of ice water to the reaction system, separate the liquids, and use the organic phase for later use, extract the water phase twice with 15ml of dichloromethane each time, combine the organic phases; add 30ml of 10% saline solution for washing, and separate the organic phase to 100ml There-necked flask; add 8.0 g of...

Embodiment 2

[0066] The preparation of embodiment 2 ticagrelor impurity 8

[0067]

[0068] 1. Preparation of Impurity 8 Intermediate 1

[0069] 5.85g (13.96mmol) 2-[((3aR,4S,6R,6aS)-6-{[5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl]amino}-2, 2-Dimethyltetrahydro-3aH-cyclopentadieno[d][1,3]dioxolan-4-yl)oxy]ethanol (A), 5.0 g (11.63 mmol) 2- ({(3aR,4S,6R,6aS)-6-[7-Chloro-5-(propylmercapto)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl ] -2,2-Dimethyltetrahydro-3aH-cyclopentadieno[d][1,3]dioxolan-4-yl}oxy)ethanol (B) was added to a 100ml three-necked flask in sequence 50ml of acetonitrile and 11.37g (34.89mmol) of cesium carbonate were added, and the temperature was raised to 50~60°C for 24h. Cool down to 40~45°C with tap water, add 100ml of purified water, extract 3 times with 70ml of dichloromethane / time, combine the organic phase into a 250ml three-neck flask, add 20g of anhydrous sodium sulfate and stir for 2h, filter, collect the filtrate, and store at 40°C Concentration under reduced...

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Abstract

The invention discloses ticagrelor impurity, namely ticagrelor impurity 7 and ticagrelor impurity 8; in addition, the invention also discloses a preparation method and application thereof. According to the ticagrelor impurity and the preparation method thereof provided by the invention, foundation is laid for the quality researches on a ticagrelor intermediate, raw medicinal materials and a composition thereof.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and more specifically relates to ticagrelor-related impurities and a preparation process thereof. Background technique [0002] Platelets have long been considered essential for hemostasis. Hemostasis is the body's protective process of stopping bleeding from damaged blood vessels. But abnormal hemostasis in blood vessels can produce clots. Platelets are an important cause of clot formation and growth in blood vessels. Platelets are released by irregular blood flow conditions in blood vessels with disease or from damaged vascular endothelial cells or other circulating cells. In the event of activation of the mediator, it may increase the size of the clot, making the clot seal off the arterial vessel in the area of ​​the damaged vessel. Venous clots can partially and easily detach as emboli, which migrate through circulatory organs and can cause obstruction of other vessels. Arterial clo...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D239/48G01N1/28G01N24/08
CPCC07B2200/07C07D239/48C07D487/04G01N1/28G01N24/087
Inventor 邓祥林李大明黄超民黄明会余佳李宏伟杨永茂张竞
Owner ZEIN BIOTECHNOLOGY CO LTD
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