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Preparation method of ticagrelor key chiral intermediate isomer impurity TGAD2

A chiral intermediate, the technology of ticagrelor, is applied in the field of medicinal chemistry to achieve the effects of high refining yield and purity, simple reaction conditions and mild reaction conditions

Pending Publication Date: 2021-10-01
CHANGZHOU PHARMA FACTORY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0006] At present, there is no relevant report on the preparation of the isomer impurity TGAD2 using TGA as the starting material

Method used

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  • Preparation method of ticagrelor key chiral intermediate isomer impurity TGAD2
  • Preparation method of ticagrelor key chiral intermediate isomer impurity TGAD2
  • Preparation method of ticagrelor key chiral intermediate isomer impurity TGAD2

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Experimental program
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Embodiment 1

[0031] (1) Preparation of formula 11 compound

[0032] TGA (80 g, 0.4624 mol) was dissolved in 250 mL of tetrahydrofuran, 200 mL of water was added, and potassium carbonate (127.62 g, 0.9248 mol) was added. 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 sodium sulfate and concentrated to obtain 106 g of product (HPLC: 95%);

[0033]

[0034] (2) preparation of formula 18 compounds

[0035] The compound of formula 11 (100g, 0.3256mol) was dissolved in 600mL of dichloromethane, triethylamine (65.85g, 0.6508mol) was added, and acetic anhydride (39.86g, 0.3905mol) was added under stirring at room temperature, the addition was completed, and refluxed for 24h. As detected by TLC, the starting material was complete...

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Abstract

The invention relates to a method for preparing an isomer impurity TGAD2 from a key optically active intermediate TGA of ticagrelor. According to the method, the TGAD2 is prepared through the steps of Cbz protection, esterification reaction, deprotection reaction, oxidation reaction, reduction 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 TGAD2, a key chiral intermediate isomer impurity 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 du...

Claims

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Application Information

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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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