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Environment-friendly preparation method of ozagrel impurity II

An environmentally friendly, impurity technology, applied in the field of pharmaceutical impurity standard preparation, to achieve the effects of improving accuracy and sensitivity, convenient operation, and wide linear range

Inactive Publication Date: 2020-06-12
深圳市祥根生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no relevant literature reporting the preparation method of Ozagrel impurity II, especially the environment-friendly preparation method of high-purity Ozagrel impurity II

Method used

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  • Environment-friendly preparation method of ozagrel impurity II
  • Environment-friendly preparation method of ozagrel impurity II
  • Environment-friendly preparation method of ozagrel impurity II

Examples

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Comparison scheme
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preparation example Construction

[0030] An environment-friendly preparation method of ozagrel impurity II, comprising the following synthetic route:

[0031]

[0032] The steps are as follows:

[0033] 4-iodotoluene and ethyl propiolate on Cu 2 Ozagrel impurity II was obtained by the reaction under the catalysis of O.

[0034] The preparation method of the invention has simple steps, cheap and easy-to-obtain raw materials, mild reaction conditions, stable process, good reproducibility, emission reduction and environmental protection, high product yield, high purity of the obtained ozagrel impurity II, good stability performance, and can be used as The standard is used to identify the impurity Ⅱ produced in the synthesis of ozagrel, effectively detect the residual amount of the impurity Ⅱ of ozagrel in the synthesis product of ozagrel, which is a necessity for the quality control of ozagrel, and to carry out qualitative and quantitative analysis of related substances detection and control.

[0035] In so...

Embodiment 1

[0053] An environment-friendly preparation method of ozagrel impurity II, specifically comprising the following steps:

[0054] (1) Add 25 mL of dry dimethylformamide to 2.00 mL of ethyl propiolate, then add 2.18 g of 4-iodotoluene and mix well, then add Cu 2 O 2.86g, the system was subjected to vacuum / nitrogen circulation degassing operation 3 times, and then the system was stirred and reacted at 100°C for 16h in a nitrogen protection environment;

[0055] (2) The mixture system that completes the reaction is cooled to room temperature, then vacuumizes to remove solvent, then adds 30ml saturated NaCl solution to wash, and adopts 50ml dichloromethane to extract, gained organic matter is washed with NaCl 2 SO 4 Dry, filter, and concentrate in vacuo to obtain a crude product, which is purified by thin-layer chromatography. The developer ratio for chromatography is petroleum ether:ethyl acetate=10:1, and 760.00 mg of a yellow liquid product-Ozagrel impurity II is obtained. The ...

Embodiment 2

[0057] An environment-friendly preparation method of ozagrel impurity II, which differs from Example 1 only in that:

[0058] In step (1): Cu 2 The amount of O added is 3.00g, and the system is subjected to vacuum / nitrogen cycle degassing operation twice, and then the system is stirred and reacted at 105°C for 15h in a nitrogen protection environment;

[0059] In step (2): the crude product is purified by thin-layer chromatography, and the ratio of developing solvent for chromatography is petroleum ether:ethyl acetate=12:1, and 769.41mg of yellow liquid product-Ozagrel impurity II is obtained, and the yield of the product is was 40.9%.

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Abstract

The invention provides an environment-friendly preparation method of an ozagrel impurity II, and belongs to the technical field of preparation of drug impurity standard substances. The preparation method comprises the following steps: reacting 4-iodotoluene with ethyl propiolate under the catalytic action of Cu2O to prepare the ozagrel impurity II. The preparation method has the advantages of simple steps, cheap and easily available raw materials, mild reaction conditions, stable process, good reproducibility, emission reduction, environmental protection and high product yield; the purity of the prepared ozagrel impurity II is high; the ozagrel impurity II prepared by the method has good stability and can be used as a standard substance for identifying the impurity II generated in ozagrelbulk drug synthesis and can effectively detect the residual amount of the ozagrel impurity II in the ozagrel bulk drug and is a necessity for ozagrel quality control and can qualitatively and quantitatively detect and control related substances. The method is used for detecting the ozagrel impurity II and can effectively improve the accuracy and the sensitivity of the detection result and shows awide linear range and is beneficial to improving the drug purity of ozagrel.

Description

technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical impurity standard products, and in particular relates to an environment-friendly preparation method of ozagrel impurity II. Background technique [0002] Ozagrel, whose chemical formula is trans-3-[4-(1H-imidazole-1-methyl)phenyl]-2-acrylic acid, is a selective thromboxane (TX) synthase inhibitor, which can inhibit the activity of TXA2 It is mainly used to treat various acute thrombotic cerebral infarctions. Ozagrel prevents prostaglandin H2 (PGH2) from producing thromboxane A2 (TXA2), and promotes the transfer of platelet-derived PGH2 to endothelial cells, which are used to synthesize PGI2, thereby improving the abnormal balance between TXA2 and prostaglandin PGI2. Ozagrel inhibits platelet aggregation and dilates blood vessels. Ozagrel Sodium for Injection and Ozagrel Sodium Injection are its preparations, clinically mainly applicable to acute thrombotic cerebral infarcti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/343C07C67/58C07C67/56C07C69/618G01N30/02G01N30/06G01N30/54G01N30/74G01N27/62G01N24/08
CPCC07C67/343C07C67/56C07C67/58C07C69/618G01N24/08G01N27/62G01N30/02G01N30/06G01N30/54G01N30/74G01N2030/027G01N2030/062
Inventor 周佳
Owner 深圳市祥根生物科技有限公司
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