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Preparation method of mycophenolate mofetil impurity A

A technology of mycophenolate mofetil and impurities, applied in the field of preparation of mycophenolate mofetil impurity A, to achieve the effects of good reaction selectivity, high reaction yield and high purity

Pending Publication Date: 2021-10-26
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the existing literature has also reported the detection and analysis methods of related impurities, which provides a certain basis for the study of the content of impurities in active ingredients, etc., but there is no efficient and feasible preparation method for related impurities, especially impurity A, reported in the literature.

Method used

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  • Preparation method of mycophenolate mofetil impurity A
  • Preparation method of mycophenolate mofetil impurity A
  • Preparation method of mycophenolate mofetil impurity A

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Under nitrogen protection, add 43.35g of mycophenolate mofetil and 5.56g of magnesium iodide into a three-necked flask, add 433.5ml of dichloromethane, stir and cool down to -15~-10°C, and dropwise add 100.20g of tribromo 200ml of dichloromethane solution of boron chloride (mass-to-mass ratio 1:2), after the dropwise addition is completed, the temperature is slowly raised to 30-35°C, and the reaction is kept for 3-4 hours. After the reaction was completed, under stirring, the reaction mixture was added to 1500ml of ice-water mixture, and the layers were separated. The organic layer was washed with 200ml of 5% aqueous sodium bicarbonate solution, 200ml of saturated brine, dried over anhydrous sodium sulfate for 4 hours, and evaporated under reduced pressure. Dry, obtain the crude product of 37.8g mycophenolate mofetil impurity A.

[0032] Under nitrogen protection, add 37.8g of mycophenolate mofetil impurity A crude product into a three-necked flask, add 380ml of a mixtu...

Embodiment 2

[0034] Under the protection of nitrogen, add 43.35g of mycophenolate mofetil and 2.78g of magnesium iodide into a three-necked flask, add 520ml of dichloromethane, stir and cool down to -15~-10°C, and dropwise add 75.15g of tribromide Boron dichloromethane solution 150ml (mass-to-mass ratio 1:2), after the dropwise addition, slowly raise the temperature to 30-35°C, and keep it warm for 3-4 hours. After the reaction was completed, under stirring, the reaction mixture was added to 1500ml of ice-water mixture, and the layers were separated. The organic layer was washed with 200ml of 5% aqueous sodium bicarbonate solution, 200ml of saturated brine, dried over anhydrous sodium sulfate for 4 hours, and evaporated under reduced pressure. Dry, obtain the crude product of 35.7g mycophenolate mofetil impurity A.

[0035]Under nitrogen protection, add 35.7g of mycophenolate mofetil impurity A crude product into a three-necked flask, add 360ml of a mixture of butyl acetate and ethanol (vo...

Embodiment 3

[0037] Under nitrogen protection, add 43.35g of mycophenolate mofetil and 8.34g of magnesium iodide into a three-necked flask, add 650ml of dichloromethane, stir and cool down to -15~-10°C, and dropwise add 125.26g of tribromide Boron dichloromethane solution 250ml (mass-to-mass ratio 1:2), after the dropwise addition, slowly raise the temperature to 30-35°C, and keep it warm for 3-4 hours. After the reaction was completed, under stirring, the reaction mixture was added to 1500ml of ice-water mixture, and the layers were separated. The organic layer was washed with 200ml of 5% aqueous sodium bicarbonate solution, 200ml of saturated brine, dried over anhydrous sodium sulfate for 4 hours, and evaporated under reduced pressure. Dry, obtain the crude product of 35.9g mycophenolate mofetil impurity A.

[0038] Under nitrogen protection, add 35.9g of mycophenolate mofetil impurity A crude product into a three-necked flask, add 360ml of a mixture of butyl acetate and ethanol (volume ...

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Abstract

The invention provides a preparation method of a high-purity mycophenolate mofetil impurity A. Compared with the prior art, the method provided by the invention has the advantages of high reaction yield, good reaction selectivity, few byproducts and high target product purity.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a preparation method and application of mycophenolate mofetil impurity A. Background technique [0002] Mycophenolate mofetil (E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuryl)-4- Methyl-4-hexenoic acid-2-morpholino ethyl ester), its structure is as shown in formula I, is the 2-ethyl morpholino ester of mycophenolic acid (Mycophenolic acid, MPA) as shown in formula II derivative. [0003] [0004] Mycophenolate mofetil, also known as mycophenolate mofetil (MMF), trade name Cellcept, was developed by Syntex Corporation of the United States. thing. Mycophenolate mofetil is a reversible cytostatic agent that has been clinically used for many years, mainly for the treatment of psoriasis. In the late 1980s, organ transplant animal experiments confirmed that it can significantly prolong the survival time of rodent and dog allograft kidn...

Claims

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Application Information

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IPC IPC(8): C07D307/88
CPCC07D307/88
Inventor 白文钦朱学环刘忠
Owner LUNAN PHARMA GROUP CORPORATION
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