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Compound as well as preparation method, preparation and application thereof

A technology of compound and target compound, which is applied in the field of compound and its preparation, achieves less environmental pollution, simple and easy preparation method, and obvious anticoagulant effect

Active Publication Date: 2017-06-13
KPC PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, currently there are few reports on the structural modification of gastrodin aglycon and the development of drugs with cardiovascular and cerebrovascular applications.

Method used

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  • Compound as well as preparation method, preparation and application thereof
  • Compound as well as preparation method, preparation and application thereof
  • Compound as well as preparation method, preparation and application thereof

Examples

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preparation example Construction

[0028] The preparation method of the compound described in the present invention is to take 2-chloro-4 hydroxybenzaldehyde or 2-bromo-4 hydroxybenzaldehyde as raw material and tetraacetylglucose trichloroacetimidate generation Schmidt reaction, then with NaBH4 or DAST The reaction is carried out to obtain the target compound.

[0029] The reaction formula for this reaction is:

[0030] In an embodiment, the reaction is specifically 2-chloro-4-hydroxybenzaldehyde, 2-bromo-4-hydroxybenzaldehyde etc. and tetraacetylglucose trichloroacetimide ester under the condition of organic solvent and catalyst Schmidt reaction and then with NaBH 4, DAST, etc. to react to obtain the compound.

[0031] Organic solvents refer to a class of organic compounds that contain carbon atoms and can dissolve water-insoluble substances, including alkanes, alkenes, alcohols, aldehydes, amines, esters, ethers, ketones, aromatic hydrocarbons, hydrogenated hydrocarbons, terpene hydrocarbons, Halogenated h...

Embodiment 1

[0045] Preparation of KPC-4000020:

[0046]

[0047] Add compound 1 (400 mg, 1.99 mmol, 1.0 eq), compound 2 (1.76 g, 3.58 mmol, 1.8 eq) and molecular sieves (3.0 g, 4A) in a 25 ml two-necked flask. Replace nitrogen. Dichloromethane (5 mL) was successively added to the flask, and the flask was placed in an ice bath and stirred for 30 minutes. Add boron trifluoride diethyl ether (0.28 mL, 2.19 mmol, 1.1 eq) slowly dropwise with a syringe. Stirring was continued for 30 minutes after the dropwise addition was complete. Then the ice bath was removed, and the reaction solution was naturally warmed to room temperature (20°C). The reaction proceeded 8 times by TLC until the starting material disappeared (2 hours). Slowly pour the reaction solution into a beaker filled with crushed ice (20 g) to quench. After the ice was completely melted, the aqueous phase of the resulting mixture was extracted with ethyl acetate (20 mL × 3). The organic phases were combined and dried over an...

Embodiment 2

[0050] Preparation of KPC-4000021:

[0051]

[0052] Compound KPC-4000020 (300 mg, 0.56 mmol, 1.0 eq) was dissolved in 2.0 mL of methanol, cooled to 0 °C under nitrogen protection, and sodium borohydride (21 mg, 0.56 mmol, 1.0 eq) was added in portions. Then the ice bath was removed, and the reaction solution was naturally warmed to room temperature (20°C). The progress of the reaction was monitored by TLC until the starting material disappeared (1 hour). The reaction solution was slowly poured into a saturated solution of NH4Cl (20 mL). The aqueous phase of the resulting mixture was extracted with ethyl acetate (10 mL × 3). The organic phases were combined and dried over anhydrous sodium sulfate. The mixture was filtered. The solvent was removed on a rotary evaporator. The crude product was purified with a silica gel column. Eluent ratio: ethyl acetate / petroleum ether = 60%. Obtained white solid 221 mg, yield: 73%.

[0053] 1H NMR (400 MHz, CDCl3) δ 7.57 (s, 1H), 7...

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Abstract

The invention discloses a compound as well as a preparation method, a preparation and application thereof. The compound has the following structure shown in the specification, wherein X is hydrogen; R is other compound residues. The preparation method comprises the following steps: taking 2-chloro-4-hydroxybenzaldehyde or 2-bromo-4-hydroxybenzaldehyde as raw materials, performing Schmidt reaction with tetraacetylglucose trichloroacetimidate and then reacting with NaBH4 or DAST to obtain a target compound. The preparation is a tablet, a capsule, an injection or a freeze-dried powder injection prepared by adding pharmaceutically-acceptable excipients in the compound. The application is application of the compound to the preparation of an anticoagulant drug. The compound disclosed by the invention has an obvious anticoagulant effect and can be taken as a potential lead compound to be applied to the preparation of the drug for treating deep vein thrombus, pulmonary thromboembolism, cardiovascular and cerebrovascular diseases, stroke and other diseases related to blood coagulation; the preparation method is simple and easy to implement, good in repeatability and less in environmental pollution, and can be used for the preparation of a large amount of compounds.

Description

technical field [0001] The invention belongs to the technical field of medicine preparation, and specifically relates to a compound and its preparation method, preparation and application. Background technique [0002] Cardiovascular and cerebrovascular disease is a common disease that seriously threatens the health of human beings, especially middle-aged and elderly people. The number of people who die from cardiovascular and cerebrovascular diseases in the world is as high as 15 million every year, ranking first among various causes of death. At present, there are more than 270 million patients with cardiovascular and cerebrovascular diseases in my country, and nearly 3 million people die from cardiovascular and cerebrovascular diseases in China every year, accounting for 51% of the total annual death causes in my country. Cardiovascular and cerebrovascular diseases have become the number one killer with the highest cause of death for human beings, and they are also the "s...

Claims

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Application Information

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IPC IPC(8): C07H15/203C07H1/00A61K31/7034A61P9/00A61P9/10
Inventor 李剑峰坝德伟周思雨黄茜杨兆祥张建文
Owner KPC PHARM INC
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