Preparation method of related substance B of fondaparinux sodium injection

A technology for fondaparinux sodium and related substances, applied in the field of medicine, can solve the problems such as no literature report in the synthesis method of substance B, and achieve the effects of easy to scale-up preparation, high yield and simple operation

Inactive Publication Date: 2019-05-10
HUAIBEI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, there is no literature report on the synthesis method of substance B.

Method used

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  • Preparation method of related substance B of fondaparinux sodium injection
  • Preparation method of related substance B of fondaparinux sodium injection
  • Preparation method of related substance B of fondaparinux sodium injection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041]

[0042]Dissolve 25g of compound II, 15mL of pyridine, and 0.2g of 4-dimethylaminopyridine in 400mL of dichloromethane, add 11mL of benzoyl chloride dropwise in an ice-water bath, raise the temperature to room temperature for 10 hours, and add an appropriate amount of water to quench the reaction. Washed with 0.1M hydrochloric acid, water and saturated saline solution successively, dried over anhydrous sodium sulfate, filtered, spin-dried the solvent under reduced pressure, separated and purified by column to obtain 27 g of compound III as a white solid, with a yield of 95%.

Embodiment 2

[0044]

[0045] Dissolve 25g of compound III in a mixed solution of 25mL of dichloromethane and 250mL of 0.5M HCl / MeOH, stir at room temperature for 10h, filter under reduced pressure, wash the filter cake with water until neutral, and dry it with air at 50°C to obtain 18g of compound IV as a white solid , yield 80%.

Embodiment 3

[0047]

[0048] Take 15g compound IV, 38g SO 3 · NMe 3 , 15mL DMF and 150mL acetonitrile in a single-necked bottle, reacted at 50°C for 15h under nitrogen protection, cooled to 0°C, quenched by adding 40mL of methanol dropwise, and washed with saturated NaHCO 3 The pH of the aqueous solution was adjusted to 8, filtered, and concentrated under reduced pressure to remove the organic solvent to obtain an aqueous solution of the crude compound V, which was separated and purified on a C18 column to obtain 16 g of compound IV as a white solid, with a yield of 85%.

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PUM

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Abstract

The invention discloses a preparation method of a related substance B of fondaparinux sodium injection. A compound II is taken as a starting raw material, and the target product related substance B isobtained through benzoylation, deacetylation protection, hydroxysulfonation, benzyl removing through hydrogenation and hydrolysis. A synthesis method of the related substance B of the fondaparinux sodium injection has the advantages that the operation is simple, the yield is high, and scale enlarging preparation is easy, and a better foundation is laid for the quality studying and controlling offondaparinux sodium injection.

Description

technical field [0001] The invention relates to a method for preparing related substance B of fondaparinux sodium injection, belonging to the technical field of medicine. Background technique [0002] Fondaparinux sodium injection (Fondaparinux sodium injection) is the first targeted anti-factor Xa inhibitor developed and produced by Sanofi Company in France. Thrombosis and pulmonary embolism, is a fully synthetic pentose sugar compound, its chemical name is: oxy-[2-deoxy-6-oxo-sulfonic acid-2-(sulfonyl)-α-D-glucopyranosyl ]-(1→4)-oxygen-(β-D-glucopyranose)-(1→4)-oxygen-[2-deoxy-3,6-di-oxo-sulfonic acid-2-( Sulfonyl)-α-D-glucopyranose]-(1→4)-oxy-(2-oxo-sulfonic acid-α-L-iduronic acid)-(1→4)-oxygen -[2-Deoxy-1-oxo-methyl-6-oxo-sulfonic acid-2-(sulfonyl)-α-D-glucopyranoside] decasodium salt, the structural formula is as follows: [0003] [0004] Fondaparinux sodium is a new type of highly selective factor Xa inhibitor, which is a methyl derivative of pure chemically syn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18C07H1/00
CPCY02P20/55
Inventor 张顺吉
Owner HUAIBEI NORMAL UNIVERSITY
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