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A kind of purification method of regadeson

A technology of regardson and purification method, applied in the direction of organic chemistry, etc., can solve the problems of poor quality, unavailability, high content of impurity A, and achieve the effect of good product quality

Active Publication Date: 2020-03-27
CHINA NAT MEDICINES GUORUI PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The technical problem to be solved by the present invention is to overcome the existing method for purifying the crude product of Regadeson with impurity A as the main impurity. , defects such as regadeson products that meet the quality requirements of pharmaceuticals, and provide a purification method for regadeson

Method used

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  • A kind of purification method of regadeson
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  • A kind of purification method of regadeson

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Take 1 g of Regadeson crude product (HPLC purity 99.58%, impurity A content 0.35%), add 6 mL of DMSO to dissolve, heat to about 80 ° C, dropwise add 9 mL of aqueous sodium hydroxide solution with a concentration of 0.1 mol / L, and gradually precipitate during the dropping process The white solid was naturally cooled to room temperature after the dropwise addition, then stirred for 2 hours, filtered, and the filter cake was washed with 10 mL of pure water and 10 mL of ethanol in turn, and vacuum-dried at 50°C to obtain 0.97 g of Regadeson product. The HPLC results showed that the content of regadeson was 99.89%, and the content of impurity A was 0.05%.

Embodiment 2

[0040] Take 1 g of Regadeson crude product (HPLC purity 98.0%, impurity A content 1.0%), add 20 mL of DMSO to dissolve, heat to about 70 ° C, add dropwise 3 mL of potassium carbonate aqueous solution with a concentration of 0.5 mol / L, and gradually precipitate solid during the dropping process After the dropwise addition, it was naturally cooled to room temperature, stirred for another 3 hours, filtered, and the filter cake was washed with 10 mL of pure water and 10 mL of ethanol in turn, and vacuum-dried at 55°C to obtain 0.85 g of the Regadeson product. HPLC results showed that the content of regadeson was 99.87%, and the content of impurity A was 0.03%.

Embodiment 3

[0042] Take 1 g of Regadeson crude product (HPLC purity 99.50%, impurity A content 0.45%), add 10 mL of DMF to dissolve, heat to about 70 ° C, add dropwise 6 mL of sodium carbonate aqueous solution with a concentration of 0.1 mol / L, and gradually precipitate solid during the dropwise addition After the dropwise addition, it was naturally cooled to room temperature, stirred for another 2 hours, filtered, and the filter cake was washed with 10 mL of pure water and 10 mL of ethanol in turn, and vacuum-dried at 50°C to obtain 0.95 g of Regadeson product. The HPLC results showed that the content of regadeson was 99.89%, and the content of impurity A was 0.04%.

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Abstract

The present invention discloses a regadenoson purification method, which comprises: under the effect of an alkali water solution, mixing an impurity A-containing regadenoson crude product and a polar organic solvent, and crystallizing, wherein the impurity A content in the regadenoson crude product is 0.1-1.0%. According to the present invention, with the purification method, the impurity A in the regadenoson crude product can be effectively removed, the impurity A content in the obtained regadenoson product is less than 0.10%, and the lowest content is less than 0.04%, such that the HPLC purity of the regadenoson product is further improved, the HPLC purity of the finally-obtained regadenoson product is more than 99.80%, the product quality is good, and impurity limit standard of ICH Q3a is completely met. The formula of the impurity A is represented in the specification.

Description

technical field [0001] The invention provides a method for purifying regadeson. Background technique [0002] Regadeson, English common name Regadenoson, chemical name 1-(6-amino-9-β-D-ribofuranosyl-9H-purin-2-yl)-N-methyl-1H-pyrazole-4- Formamide, formula C 15 h 18 N 8 o 5 , molecular weight 390.35, CAS registration number 875148-45-1, adenosine A jointly developed by CV Therapeutics and Astellas Pharma in the United States 2A Agonists, by activating adenosine A 2A Coronary arterial vasodilation and increased coronary blood flow to assist in the diagnosis of coronary artery disease. It was launched in the United States in April 2008 and is used for radionuclide myocardial perfusion imaging. Its structure is as follows: [0003] [0004] Patent CN102260311A reports that the synthetic method of Regadeson is as follows: 2-chloroadenosine 2 is used as the starting material, and 2-hydrazinoadenosine 3 is obtained by substituting hydrazine hydrate, and then combined with...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/34
CPCC07D473/34
Inventor 张福利吴立前裘鹏程焦慧荣蒋敏陈梦柯陈辉柯彬王磊
Owner CHINA NAT MEDICINES GUORUI PHARMA
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