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Preparation method of ticagrelor key chiral intermediate isomer impurity TGAD1

The technology of a chiral intermediate, ticagrelor, is applied in the field of medicinal chemistry to achieve the effects of mild reaction conditions, high refining yield and purity, and convenient post-processing

Pending Publication Date: 2021-10-01
CHANGZHOU PHARMA FACTORY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there is no report on the preparation of the isomer impurity TGAD1 using TGA as the starting material

Method used

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  • Preparation method of ticagrelor key chiral intermediate isomer impurity TGAD1
  • Preparation method of ticagrelor key chiral intermediate isomer impurity TGAD1
  • Preparation method of ticagrelor key chiral intermediate isomer impurity TGAD1

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Experimental program
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Effect test

Embodiment 1

[0034] (1) Dissolve TGA (80 g, 0.4624 mol) in 250 mL of tetrahydrofuran, add 200 mL of water, and add potassium carbonate (127.62 g, 0.9248 mol). Stir to dissolve, lower the temperature to 0°C, add benzyl chloroformate (118.33g, 0.6936mol) dropwise, and stir at room temperature for 5min after dropping, the raw materials are completely converted, separate layers, add 150mL ethyl acetate to extract the aqueous layer, and combine the organic layers. Dried over anhydrous sodium sulfate, concentrated to obtain 110 g of product (HPLC: 95%);

[0035]

[0036] (2) Add the compound of formula 11 (100g, 0.3256mol), sodium bromide (16.75g, 0.1628mol), sodium bicarbonate (32.8g, 0.3905mol), TEMPO (763mg, 4.884mmol), into a 5000mL three-necked flask, Add 1L of dichloromethane and 1L of water, stir to dissolve. Cool down to 0°C, slowly add sodium hypochlorite solution (8%w, 800mL) dropwise, and control the temperature not to exceed 10°C. After dripping, keep warm for 10 minutes. TLC d...

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Abstract

The invention relates to a method for preparing an isomer impurity TGAD1 by using a key optically active intermediate TGA of ticagrelor. According to the method, the TGAD1 is prepared through the steps of Cbz protection, oxidation reaction, reduction reaction, esterification reaction, deprotection reaction and the like. The method has the advantages of simple and mild reaction conditions, convenient post-treatment, and high refining yield and purity. The obtained sample can be further used as an impurity reference substance of a ticagrelor intermediate, and quality control of ticagrelor can be improved.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of the key chiral intermediate isomer impurity TGAD1 of ticagrelor. Background technique [0002] Impurities in drugs are the main factors affecting the purity of drugs. If the impurities contained in drugs exceed the limit requirements specified in the quality standards, it is very likely to cause changes in the appearance, properties, and physical and chemical parameters of the drug, and even affect the stability of the drug, making the drug active. Reduce and increase toxic and side effects, seriously endangering the product quality of medicines and the medication safety of patients. [0003] Ticagrelor is a new type of selective small molecule anticoagulant drug developed by AstraZeneca. The structure of its key chiral intermediate TGA is as follows: [0004] [0005] TGA has four chiral centers, and a variety of isomer impurities will be produced d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/44
CPCC07D317/44C07B2200/07
Inventor 金生华金晓峰曹鹏
Owner CHANGZHOU PHARMA FACTORY
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