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Synthetic method of ozagrel

A technology of ethyl rathate and ethyl cinnamate, applied in the field of medicine, can solve problems such as low yield of the synthesis method

Active Publication Date: 2014-06-18
北京易明康元医药科技有限公司
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are several synthetic routes of ozagrel, but the most commonly used method is to brominate p-methyl cinnamate to obtain p-bromomethyl cinnamate, and react p-bromomethyl cinnamate with imidazole to obtain ozagrel ester Ozagrel is obtained after hydrolysis. This method is relatively mature and suitable for industrial production, but there are defects such as low yield in this synthetic method. Therefore, researching a synthetic method with high yield will be able to reduce production costs and reduce production costs. patient burden

Method used

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  • Synthetic method of ozagrel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Take 380g of ethyl p-methylcinnamate, 708g of NBS, 6.56g of azobisisobutyronitrile, and 1000ml of acetonitrile, heat to reflux for 5h, filter, and concentrate the filtrate to obtain an oil, which is recrystallized with 800ml of 95% ethanol and dried. Obtained 461.3 g of ethyl p-bromomethyl cinnamate with a melting point of 43-45°C. Yield 85.5%.

[0065] Get 461.3g of ethyl p-bromomethyl cinnamate, 122g of imidazole, 373g of anhydrous potassium carbonate, 3.0g of potassium iodide and 1450ml of acetone and mix completely, the mixture is heated to reflux for 15 hours, filtered, and the filtrate is concentrated to recycle the organic solvent to the utmost, and the residue Dissolve in 2600ml of ethyl acetate, wash with water 3 times, 900ml each time, dry the organic phase with MgSO4, filter, concentrate the filtrate until the organic solvent is exhausted, dry to obtain a solid, and use a volume ratio of 1:1 ethyl acetate-petroleum ether Recrystallized, concentrated, and dri...

Embodiment 2

[0068] Take 1900g of ethyl p-methyl cinnamate, 3540g of NBS, 32.8g of azobisisobutyronitrile, and 5L of acetonitrile, heat to reflux for 6h, filter, and concentrate the filtrate to obtain an oil, which is recrystallized with 5L of 95% ethanol and dried. 2290 g of ethyl p-bromomethyl cinnamate was obtained, with a melting point of 43-45°C. Yield 85.1%.

[0069] Get 2290g of ethyl p-bromomethyl cinnamate, 609.3g of imidazole, 1855g of anhydrous potassium carbonate, 14.9g of potassium iodide and 7.2L of acetone and mix completely, the mixture is heated to reflux for 16 hours, filtered, and the filtrate is concentrated to recycle the organic solvent to the utmost, and the remaining The product was dissolved in 13.5L of ethyl acetate, washed with water 3 times, 4L each time, the organic phase was dried with MgSO4, filtered, the filtrate was concentrated to the organic solvent, dried to obtain a solid, and the volume ratio was 1: 1 ethyl acetate- Petroleum ether was recrystallized,...

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Abstract

The invention belongs to the technical field of medicine and discloses a preparing method of ozagrel. The method includes the following steps: the 4-bromomethyl ethyl cinnamate is obtained via the reaction of 4-methyl ethyl cinnamate and NBS; ozagrel ethyl is obtained via the reaction of 4-bromomethyl ethyl cinnamate and imidazole; then the crude ozagrel is obtained via hydrolyzing the ozagrel ethyl; and the ozagrel is obtained by refining compound solvent. The method provided by the invention has the advantages of high yield and little environmental pollution, and is more suitable for industrial production; a stability experiment on the ozagrel produced via the preparing method shows that the ozagrel is stable in property, is convenient for transportation and storage, and can be used as an injection material.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a method for synthesizing ozagrel. Background technique [0002] Thrombosis is a disease caused by abnormal blood clots forming in blood vessels during human and animal life. The formation of thrombus includes many related factors, such as vessel wall, platelets, coagulation and hemolysis, blood flow and blood viscosity, etc. Thrombosis is a group of complications caused by many different diseases with different causes. Due to the differences in various underlying diseases and the different sites of thromboembolism, the clinical manifestations of thrombosis are also different. 1. Arterial thrombosis is seen in: (1) coronary arteriosclerotic heart disease: when coronary artery branch or trunk thrombus causes myocardial ischemia, angina pectoris or myocardial infarction may occur; (2) cerebral artery thrombosis: can lead to a transient (4) Peripheral arterial occlus...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/56
Inventor 曹捷高帆周战尚磊
Owner 北京易明康元医药科技有限公司
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