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Fondaparinux sodium disaccharide intermediate preparation method

A technology for fondaparinux sodium and intermediates, applied in the field of preparation of fondaparinux sodium disaccharide intermediates

Inactive Publication Date: 2014-10-15
李正海
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The clinical performance of fondaparinux sodium is very good, and the sales are also increasing year by year, but its structure is complex, the synthesis steps are long and difficult, and the production cost has always been high , limiting its application

Method used

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Examples

Experimental program
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Effect test

preparation example Construction

[0018] A preparation method of fondaparinux sodium disaccharide intermediate, comprising the following steps:

[0019] Step 1) preparing the compound of formula IV by using the compound of formula II and the compound of formula III;

[0020] Step 2) reusing the prepared compound of formula IV to prepare the compound of formula I;

[0021] The reaction scheme of described step (1) and (2) is .

[0022] Further, the reaction in step (1) is carried out in a solvent, the solvent is preferably a high-boiling aprotic solvent, more preferably halogenated benzene, most preferably chlorobenzene; the reaction temperature is preferably 30-180 o C, more preferably 100-150 o C, most preferably 140 o C; the reaction catalyst is preferably a pyridine inorganic salt complex, most preferably 2,4-lutidine perchlorate.

[0023] Further, the reaction in step (2) is carried out in a solvent, the solvent is preferably an organic solvent, more preferably an organic base / alcohol mixture, most p...

Embodiment 1

[0026] 1. Synthesis of Compound IV

[0027] 30 g of compound I and 25 g of II were dissolved in 1 L of chlorobenzene and heated to boiling (140 o C) Add 400 mL of freshly prepared chlorobenzene solution (0.006 mmol) of 2,4-lutidine perchlorate after evaporating 900 mL of solvent, evaporate 400 mL of solvent while adding, and continue to react for 1 hour , then added 500 mL of solvent, distilled, and kept the volume of the reaction solution at about 150 mL. After the reaction was completed, dichloromethane was added, washed with saturated sodium bicarbonate and water, and the target compound 11 was purified by column chromatography after the organic phase was concentrated. g.

[0028] 2. Synthesis of compound I

[0029] 50 g compound IV and 6.5 g thiourea were dissolved in 250 mL pyridine / 50 mL ethanol and heated to 100 o C for 30 min. After the reaction was completed, it was cooled and concentrated in vacuo. The residue was dissolved in water and dichloromethane. ...

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Abstract

The invention discloses a fondaparinux sodium disaccharide intermediate preparation method which comprises the following steps: firstly, using a formula (II) compound and a formula (III) compound for preparation of a formula (IV) compound; then using the prepared formula (IV) compound for the preparation of a formula (I) compound. The technical scheme of the fondaparinux sodium disaccharide intermediate preparation method is low in cost and high in yield, raw materials are easy to prepare, and by use of the intermediate as a raw material for preparation of fondaparinux, the cost can be greatly reduced.

Description

technical field [0001] The invention relates to a preparation method of fondaparinux sodium disaccharide intermediate. Background technique [0002] Fondaparinux sodium (Fondaparinux sodium; Arixrta) is a new type of highly selective factor Xa inhibitor. It is a methyl derivative of purely chemically synthesized pentosan sodium. Its original manufacturer is Sanofi, France, and later transferred For GlaxoSmithKline, it was listed in Europe in 2001, in the United States in 2002, and in China in 2008. Its effect is mainly through the special inhibition of Xa by antithrombin (ATⅢ). Arixtra contains 5 sugar units, and its sulfate group can bind firmly and specifically to ATⅢ (its dissociation constant is 50nM), and is the main endogenous regulator of the blood coagulation process. Arixrta has the characteristics of high bioavailability, rapid onset of action, long half-life, less adverse reactions, etc., and is more convenient for clinical application. It is more effective and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18C07H1/00
Inventor 李正海
Owner 李正海
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