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Scopoletin derivative as well as preparation method and application thereof

A technology of scopolide and derivatives is applied in the field of scopolide derivatives and their preparation, which can solve the problems such as inability to take orally and achieve the effects of small dosage, easy control and prolonging in vitro coagulation time.

Active Publication Date: 2014-08-06
GUANGZHOU CONSUN MEDICINE R & D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Heparin and low-molecular-weight heparin are acute and short-term medications, which can only be used for intravenous injection and cannot be taken orally

Method used

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  • Scopoletin derivative as well as preparation method and application thereof
  • Scopoletin derivative as well as preparation method and application thereof
  • Scopoletin derivative as well as preparation method and application thereof

Examples

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Comparison scheme
Effect test

preparation example Construction

[0042] The preparation method of above-mentioned scopoletin derivative or pharmaceutically acceptable salt, comprises the following steps:

[0043] Scopoletin, XRX and anhydrous potassium carbonate were dissolved in an organic solvent, stirred and reacted at 50° C. for 12 hours to obtain a scopoletin derivative. The molar ratio of scopoletin, XRX and anhydrous potassium carbonate is 1:1:1-5. Wherein, the organic solvent is used to dissolve scopoletin and XRX, and in this embodiment, the organic solvent is acetonitrile. In one embodiment, after the reaction is completed, there is a post-processing step. The specific operation is: cooling the mixed solution to room temperature, filtering, recovering the filtrate under reduced pressure, dissolving the residue with ethyl acetate, and adding an appropriate amount of KOH under stirring to react After 2 hours to remove unreacted raw materials, filter, and recover the filtrate under reduced pressure to obtain the target mixed product...

Embodiment 1

[0050] The preparation of embodiment 1 scopoletin

[0051] The synthetic route is as follows:

[0052]

[0053] Add 2,4,5-trimethoxybenzaldehyde a (24.53 g, 0.125 mol) dropwise to a stirred suspension of aluminum trichloride (67 g, 0.5 mol) in dry dichloromethane (350 mL) at room temperature The dichloromethane (125 mL) solution was dried. After the dropwise addition, the stirring reaction was continued at room temperature for 4 hours, and then another dispersion of aluminum trichloride (67 g, 0.5 mol) in dry dichloromethane (150 mL) was added. The mixed solution was stirred and reacted for 19 hours, then poured into 1 kg of ice added with 45 mL of concentrated hydrochloric acid, and the organic layer was separated, and the aqueous layer was washed twice with 200 mL of dichloromethane respectively, and the organic layers were combined, filtered through silica gel, evaporated to dryness, and weighed in ethyl acetate. The crystallized compound b was 2,4-dihydroxy-5-methoxyb...

Embodiment 2

[0058] The preparation of embodiment 2 scopoletin derivatives

[0059] The synthetic route is as follows:

[0060]

[0061] Take scopoletin 576mg (3mM), XRX 3mM and an appropriate amount of anhydrous potassium carbonate, dissolve in 9mL acetonitrile, stir and react at 20-50°C (under reflux) for 6-24h, cool the mixture to room temperature, filter, and depressurize the filtrate Recovery, the residue was dissolved with 3 mL of ethyl acetate, and an appropriate amount of KOH was added to react for 2 h under stirring to remove unreacted raw materials, filtered, and the filtrate was recovered under reduced pressure to obtain the target mixed product. The mixture mainly had two spots,

[0062] Use 200-300 mesh silica gel for column chromatography separation, respectively, petroleum ether-ethyl acetate gradient elution, LH-20 purification, TLC detection, after 1 H-NMR confirmed that it was the corresponding scopoletin derivative. Compound number, XRX and the yield of correspondin...

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Abstract

The invention discloses a scopoletin derivative as well as a preparation method and an application thereof. The general formula of the scopoletin derivative is formula (I), wherein R is selected from C1-4 alkyl and X is selected from a halo substituent. The scopoletin derivative has a remarkable anticoagulation effect and can remarkably prolong the in vitro blood coagulation time. The scopoletin derivative orally taken can quickly enter into blood to have the anticoagulation effect. The onset time and the curative effect of the scopoletin derivative for treating venous thromboembolic diseases are equivalent to those of warfarin and the scopoletin derivative is smaller in dosage and easy to control. The scopoletin derivative has novel medical use of preventing and treating venous thromboembolic diseases and meanwhile provides a novel treatment candidate medicine for patients with venous thromboembolic diseases. The invention further discloses the preparation method of the scopoletin derivative and the application of the scopoletin derivative in preparing anticoagulation medicines.

Description

technical field [0001] The invention relates to the field of medicine preparation, in particular to scopoletin derivatives and their preparation methods and applications. Background technique [0002] Thromboembolism is not only the basis of many heart diseases, but also an important complication of many heart diseases. As early as the 1970s, researchers proposed that most acute transmural myocardial infarctions were mainly caused by thrombotic occlusion of epicardial coronary arteries. Today, thrombotic disease caused by thrombus has become a common and frequent disease that seriously affects human health and life, and is called the "number one killer" by the world medical community. [0003] According to the location, condition and nature of thrombus formation, thrombotic diseases are mainly divided into arterial thrombosis and venous thrombosis. Arterial thrombosis begins with atherosclerotic lesions on the arterial wall and platelet activation. The severe clinical mani...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16A61K31/352A61P7/02
CPCC07D311/16
Inventor 郑兆广何宝朱荃石兴华王汝上段婷婷赵俊义程慧荃顾斐
Owner GUANGZHOU CONSUN MEDICINE R & D CO LTD
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