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Gastrodin derivatives, their preparation methods, their applications and pharmaceutical preparations

A pharmaceutical preparation, gastrodin technology, applied in the field of gastrodin, to achieve obvious anticoagulant effect

Active Publication Date: 2018-11-27
KPC PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Gastrodin derivatives, their preparation methods, their applications and pharmaceutical preparations
  • Gastrodin derivatives, their preparation methods, their applications and pharmaceutical preparations
  • Gastrodin derivatives, their preparation methods, their applications and pharmaceutical preparations

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preparation example Construction

[0045] The present invention also provides a preparation method of gastrodin derivatives, comprising:

[0046] Under the action of a catalyst, the compound having the structure of formula (XI) is reacted with the compound having the structure of formula (XII) in a solvent to obtain a gastrodin derivative having the structure of formula (II);

[0047]

[0048] R-OH (Ⅻ);

[0049]

[0050] Wherein, R is a substituted naphthalene ring.

[0051] In the process of preparing gastrodin derivatives, the compound of formula (XI) is tetraacetylglucose trichloroacetimidate, which can be prepared according to the preparation methods well known to those skilled in the art, and this application has no special limits. The molar ratio of the tetraacetylglucose trichloroacetimidate to the compound having the structure of formula (XII) is preferably 2 to 3:1, the reaction temperature is preferably 20 to 30°C, and the reaction time is Preferably it is 1-3h. The reaction process of gastr...

Embodiment 1

[0066] Embodiment 1: Preparation of KPC-4000012

[0067]

[0068] Add compound 1 (492.7mg, 1.23mmol, 2.0eq) in a single-necked flask of 25ml, compound 2 (162.2mg, 0.62mmol, 1.0eq) and molecular sieve (2.0g, 4A), adopt the vacuum oil pump to remove the reaction device inside The air was replaced with nitrogen, dichloromethane (4.0ml) was added to the flask, the device was placed in an ice bath, stirred for 10 minutes, and boron trifluoride diethyl ether (83.7mml, 0.68mmol, 1.1eq ), continue to stir for 10 minutes after the dropwise addition, remove the ice bath, allow the reaction solution to naturally warm up to room temperature (20°C), and use TLC to detect the reaction process until the raw materials disappear (2 hours); slowly pour the reaction solution into a container Quench in a beaker with a saturated solution of sodium bicarbonate (20ml), extract the aqueous phase of the mixed solution with dichloromethane (20ml×3), combine the organic phases, wash with water (20ml)...

Embodiment 2

[0070] Embodiment 2: Preparation of KPC-4000013

[0071]

[0072] Add compound 3 (100.0mg, 0.20mmol, 1.0eq) and anhydrous methanol (1.0ml) to a 25ml one-necked flask, place the device in an ice bath, stir for 10 minutes, and add sodium borohydride (7.7mg , 0.20mmol, 1.0eq), continue to stir for 10 minutes, remove the ice bath, allow the reaction solution to naturally warm up to room temperature (20 ° C), monitor the reaction process with TLC, until the raw material point disappears (1 minute), spin on a rotary evaporator Remove the solvent from methanol, pour into sodium hydroxide solution (1mol / L, 20ml), extract with ethyl acetate (20ml×3), combine the organic phases, wash the organic phase with water (20ml), and saturated sodium chloride (20ml) Wash the organic phase, dry with anhydrous sodium sulfate, filter the mixture, remove the solvent on a rotary evaporator, and purify the crude product with a silica gel column, eluent ratio: ethyl acetate / petroleum ether=40%, to ob...

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Abstract

The invention provides a gastrodin derivative and a preparation method thereof. The gastrodin derivative contains a substituted naphthalene ring. The invention also provides the preparation method of the gastrodin derivative, The platelet aggregation rate is determined through adopting a turbidimetric technology, and is used to evaluate the inhibition rate of the gastrodin derivative on platelet aggregation. An experiment result shows that the gastrodin derivative has an obvious anticoagulation effect, and can be applied to the preparation of medicines for treating thrombus, cardiovascular and cerebrovascular diseases, stroke and other blood aggregation related diseases as a potential lead compound.

Description

technical field [0001] The invention relates to the technical field of gastrodin, in particular to gastrodin derivatives, their preparation methods, their applications and pharmaceutical preparations. Background technique [0002] Cardiovascular and cerebrovascular diseases are a common disease that seriously threatens human beings, especially the health of 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 a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/203C07H1/00A61K31/704A61P7/02A61P9/10
CPCC07H1/00C07H15/203
Inventor 李剑峰周思雨王贤坝德伟杨兆祥张建文黄茜宋立明
Owner KPC PHARM INC
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