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Method for refining high-purity tedizolid phosphate

A technology of tedizolid phosphate and a refining method, applied in the field of medicine, can solve the problems of less tedizolid phosphate, large amount of solvent, large product impurity content, etc., and achieves the effects of good stability, stable process and mild conditions

Active Publication Date: 2016-11-23
YANGTZE RIVER PHARM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] There are few refining methods for tedizolid phosphate. Chinese patent application CN102177156A discloses a method for purifying tedizolid phosphate, but the impurity content of the obtained product is still relatively large, especially the removal effect of impurity I is relatively poor.
[0011] Although the Chinese patent application CN105085570A discloses a refining method of tedizolid phosphate, which is recrystallized with water and methanol, the inventors found that the solubility of tedizolid phosphate in water and methanol is relatively small during the research and development process. The amount of solvent required is large, and the impurity removal effect on impurity I and impurity II is extremely unsatisfactory, which limits the application of this method
[0012] Because there are few refining methods for tedizolid phosphate, and there are many problems and deficiencies in the prior art, it is necessary to invent a kind of refining method with mild conditions, high purification efficiency and suitable for industrial production to improve the quality of raw materials

Method used

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  • Method for refining high-purity tedizolid phosphate
  • Method for refining high-purity tedizolid phosphate
  • Method for refining high-purity tedizolid phosphate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] (1) Add 10g of crude tedizolid phosphate and 100ml of dimethyl sulfoxide into the reaction flask, stir, heat to about 50°C, dissolve and clarify, add a mixed solvent of 10ml of purified water and 100ml of methanol to it, and heat up to 70°C , stirred for 9 hours, cooled to 10°C, stirred for 0.5 hours, and filtered to obtain a filter cake;

[0054] (2) Transfer the filter cake obtained in step (1) into the reaction flask, add 50ml of purified water, stir, slowly add 3.85wt% sodium hydroxide aqueous solution, adjust the pH of the solution to 7.8, then slowly add the above solution to 300ml In acetone, crystallize for 0.5 hours, filter with suction, add the obtained filter cake into a mixed solvent of 120ml of purified water and 120ml of tetrahydrofuran, stir and dissolve, quickly adjust the pH to 1.5 with 2N hydrochloric acid aqueous solution, stir for 1 hour, and filter with suction to obtain the filter cake ;

[0055] (3) Dissolve the filter cake finally obtained in st...

Embodiment 2

[0058] (1) Add 10g of crude tedizolid phosphate and 100ml of dimethyl sulfoxide into the reaction flask, stir, heat to about 50°C, dissolve and clarify, add a mixed solvent of 10ml of purified water and 100ml of ethanol to it, and heat up to 70°C , stirred for 12 hours, cooled to 10°C, stirred for 0.5 hours, and filtered to obtain a filter cake;

[0059] (2) Transfer the filter cake obtained in step (1) into the reaction flask, add 50ml of purified water, stir, slowly add 3.85wt% sodium hydroxide aqueous solution, adjust the pH of the solution to 8.0, then slowly add the above solution to 350ml In acetone, crystallize for 0.5 hours, and filter with suction, add the obtained filter cake into a mixed solvent of 120ml of purified water and 120ml of tetrahydrofuran, stir and dissolve, quickly adjust the pH to 1.2 with 2N hydrochloric acid aqueous solution, stir for 1 hour, filter, and filter with suction to obtain filter cake;

[0060] (3) Dissolve the filter cake finally obtaine...

Embodiment 3

[0063] (1) Add 10g of crude tedizolid phosphate and 100ml of dimethyl sulfoxide into the reaction flask, stir, heat to about 50°C, dissolve and clarify, add a mixed solvent of 10ml of purified water and 100ml of methanol to it, and heat up to 70°C , stirred for 8 hours, cooled to 10°C, stirred for 0.5 hours, and filtered to obtain a filter cake;

[0064] (2) Transfer the filter cake obtained in step (1) into the reaction flask, add 50ml of purified water, stir, slowly add 3.85wt% sodium hydroxide aqueous solution, adjust the pH of the solution to 7.7, then slowly add the above solution to 350ml In tetrahydrofuran, crystallize for 0.5 hours, and filter with suction, add the obtained filter cake into a mixed solvent of 120ml of purified water and 120ml of tetrahydrofuran, stir and dissolve, quickly adjust the pH to 1.0 with 2N hydrochloric acid aqueous solution, stir for 1 hour, filter, and filter with suction to obtain filter cake;

[0065] (3) Dissolve the filter cake finally...

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Abstract

The invention discloses a method for refining high-purity tedizolid phosphate. The method comprises the steps of 1, heating and dissolving a tedizolid phosphate crude product with dimethylsulfoxide, adding a polar proton solvent after clarification, and conducting stirring, cooling crystallization and suction filtration; 2, adding a filter cake obtained in step 1 to water, adjusting the pH value of the solution to be alkaline with sodium hydroxide or potassium hydroxide aqueous solution, then adding the solution to a water-soluble non-proton organic solvent for crystallization and suction filtration, adding an obtained filter cake to a water and tetrahydrofuran mixed solvent, adjusting pH to be 1-2 with hydrochloric acid aqueous solution, and conducting stirring crystallization and suction filtration; 3, dissolving a filter cake finally obtained from step 2 with dimethylsulfoxide, then adding the obtained solution to a water and ethyl alcohol mixed solvent, and conducting cooling crystallization, suction filtration and drying to obtain the high-purity tedizolid phosphate. The obtained product is high in purity and stable in quality, the condition for refining is mild, operation is easy, and the method is suitable for industrial application.

Description

technical field [0001] The application belongs to the technical field of medicine, and in particular relates to a method for refining high-purity tedizolid phosphate. Background technique [0002] Tedizolid phosphate, chemical name: (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl) -5-Hydroxymethyloxazolidin-2-one dihydrogen phosphate, the structural formula is: [0003] [0004] Tedizolid phosphate is a prodrug, which can be rapidly converted into biologically active tedizolid under the action of phosphatase in the body, which can bind to the 50s subunit of ribosomal bacteria, thereby inhibiting protein synthesis. [0005] Tedizolid Phosphate was developed by Dong-A Pharmaceutical in Korea. It is the first second-generation oxazolidinone antibiotic approved by the FDA. It is clinically used to treat skin and skin tissue infections, and its efficacy is not inferior to that of Linezolid. Compared with linezolid, the safety of tedizolid phosphate is improve...

Claims

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Application Information

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IPC IPC(8): C07F9/6558
CPCC07F9/65583
Inventor 梁慧兴徐伟李浩黄猛张利军张海波陈令武柳惠赵鹏
Owner YANGTZE RIVER PHARM GRP CO LTD
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