A preparation method of an anticoagulant drug fondaparinux sodium monosaccharide fragment intermediate

A technology for fondaparinux sodium and intermediates, which is applied in the field of preparation of anticoagulant drug fondaparinux sodium monosaccharide fragment A intermediates, and can solve problems such as difficult industrial production, high-efficiency separation, and low overall synthesis efficiency , to achieve the effect of solving technical bottlenecks

Active Publication Date: 2017-12-01
CHONGQING UNIV
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Problems solved by technology

For the preparation of its A fragment, the current technical bottleneck is mainly reflected in the difficulty in efficiently separating its α and β-isomers during the process of introducing the 1-methoxy group, usually by recrystallization or multi-step Chemical transformation to achieve the above purpose (US4818816, US 20050080042; CN103122012; Hung, S.-C.Angew.Chem.Int.Ed.2014,53,9876; Shen, J.; Zhao, W.; Wang, P.et a l.Chem.Med.Chem.2014,9,1071), but the existing methods have the defects of low overall synthesis efficiency and difficulty in realizing industrial production to varying degrees

Method used

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  • A preparation method of an anticoagulant drug fondaparinux sodium monosaccharide fragment intermediate
  • A preparation method of an anticoagulant drug fondaparinux sodium monosaccharide fragment intermediate
  • A preparation method of an anticoagulant drug fondaparinux sodium monosaccharide fragment intermediate

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Embodiment 1

[0030] The preparation of the compound shown in embodiment 1 formula I

[0031]

[0032] The preparation method reference of the compound shown in formula II (Shen, J.; Zhao, W.; Wang, P.etal.Chem.Med.Chem.2014,9,1071) method, with D-glucosamine hydrochloride as The raw material is prepared through 6 steps of reaction. The compound represented by formula II is a crude product containing a mixture of α, β-isomers. The compound represented by formula II (300mg, 0.726mmol, α:β=77:22), triphenylphosphine (287mg, 1.5eq), 300mg silica gel were dissolved in THF:H 2 O=9:1 (5 mL), react at room temperature. After reacting for 24h, TLC monitored that the reaction raw materials disappeared completely, and directly added benzyl chloroformate (0.094mL, 1.5eq) and sodium bicarbonate (122mg, 2eq) to the reaction solution under an ice bath, and reacted at 0°C for 3h, followed by TLC monitoring. It shows that the reaction of raw materials is complete. Ethyl acetate and water were added ...

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Abstract

The invention provides a method for preparing a monosaccharide intermediate, which can be used for the preparation of anticoagulant drug fondaparinux sodium. The method of the present invention is simple to operate, can realize the kilogram-level preparation of Fondaparinux sodium monosaccharide fragment A intermediate with single optical activity, solves the existing technical bottleneck in the synthesis of Fondaparinux sodium A fragment, and is suitable for Industrial production.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a preparation method of an anticoagulant drug fondaparinux sodium monosaccharide fragment A intermediate. Background technique [0002] Thrombotic disease is one of the major diseases with the highest incidence rate in modern society. Among them, venous thrombosis induced by surgery, trauma (such as large-scale or lower extremity trauma), acute medical diseases (such as myocardial infarction, stroke), cancer treatment (such as hormone therapy, chemotherapy, radiotherapy), etc. Cardiopulmonary syndrome and the third major cardiovascular disease after stroke, which seriously threaten human health. At present, the prevention and treatment of venous thrombosis mainly focus on anticoagulation. Traditional anticoagulant drugs represented by unfractionated heparin and warfarin have been gradually replaced by a new generation of anticoagulant drugs due to various degrees o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/04C07H1/00
Inventor 秦勇唐培杨超戴翔王树青
Owner CHONGQING UNIV
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