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Acetagastrodin derivative, preparation method, preparation, and applications thereof

A technology for acetylgastrodin and its derivatives, which is applied in the field of acetylgastrodin derivatives and its preparation, can solve the problems of delayed bleeding risk and high requirements for purification technology, and achieve simple and easy preparation methods, good reproducibility, and selectivity high effect

Active Publication Date: 2015-07-29
KPC PHARM INC
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

The first-line treatment varieties of these types of drugs mainly have deficiencies such as delayed bleeding risk and high purification technology requirements. In order to overcome the above-mentioned deficiencies of the drugs, research and development of new, high-efficiency, and low-toxic drugs for the treatment of cardiovascular and cerebrovascular diseases is still a hot spot in drug research

Method used

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  • Acetagastrodin derivative, preparation method, preparation, and applications thereof
  • Acetagastrodin derivative, preparation method, preparation, and applications thereof
  • Acetagastrodin derivative, preparation method, preparation, and applications thereof

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preparation example Construction

[0032] The preparation method of the acetylgastrodin derivatives of the present invention is based on ethyl p-hydroxybenzoate, p-hydroxybenzaldehyde, vanillin, nicotinic acid, triacetyl gallic acid, cinnamic acid, acetylsalicylic acid, butanediol Acid anhydride or potassium 4-hydroxybutyrate is used as the raw material to undergo condensation reaction with acetylgastrodin to obtain the target product.

[0033]

[0034]

[0035] Among them, R - for

[0036] , , , , , , , or

[0037] Described condensation reaction specifically comprises:

[0038] the first sort:

[0039] Step 1, dissolve the compound shown in formula II in an organic solvent, add thionyl chloride dropwise under stirring in an ice bath, stir and react to obtain the compound shown in formula III, add an organic solvent for later use;

[0040] Step 2, ethyl p-hydroxybenzoate, p-hydroxybenzaldehyde, potassium 4-hydroxybutyrate, and vanillin are heated with the compound shown in formula...

Embodiment 1

[0069] Preparation of acetylgastrodin p-hydroxybenzaldehyde etherate:

[0070] a. Preparation of intermediate acetylgastrodin benzyl chloride

[0071] In the reaction flask, add acetylgastrodin (4.55g, 0.01mol), dichloromethane 20ml, and add thionyl chloride (2ml, 0.028mol) dropwise under stirring in an ice bath. React at 0-25°C for 2 hours, distill off the solvent and the remaining thionyl chloride under reduced pressure to obtain 4.8 g of white solid with a yield of 98%.

[0072] b. Preparation of acetylgastrodin p-hydroxybenzaldehyde etherate

[0073] In the reaction flask, add p-hydroxybenzaldehyde (1.22g, 0.01mol), 20ml of acetone, and potassium carbonate (3g, 0.02mol). Stir at 50°C for 30min, add dropwise an acetone solution of acetylgastrodin benzyl chloride (4.8g, 0.01mol), and react at 70°C for 5h. Potassium carbonate was removed by filtration, and the filtrate was concentrated under reduced pressure. Add 50 ml of dichloromethane, wash with water and saturated bri...

Embodiment 2

[0077] Preparation of acetylgastrodin ethyl paraben etherate:

[0078] Preparation of the compound acetylgastrodin ethylparaben etherate of the present invention Referring to Example 1, 4 g of acetylgastrodin ethylparaben etherate was prepared as a white solid with a yield of 66%.

[0079] The compound NMR identification is as follows:

[0080] 1 H-NMR (500MHz, CDCl 3 , δppm): δ7.99 (d, 2H), δ7.36 (d, 2H), δ7.01 (d, 2H), δ6.96 (d, 2H), δ5.29 (m, 2H), δ5 .17(t, 1H), δ5.09(d, 1H), δ5.05(s, 2H), δ4.31(m, 3H), δ4.16(d, 1H), δ3.86(m, 1H), δ2.05 (m, 12H), δ1.37 (t, 3H). The structural formula is shown in Table 1.

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Abstract

The present invention discloses an acetagastrodin derivative, a preparation method, a preparation, and applications thereof, wherein the acetagastrodin derivative is a derivative having a general formula I, and R represents an alkyl or carbonyl compound. The preparation method comprises that: ethylparaben, p-hydroxybenzaldehyde, vanillin, nicotinic acid, triacetyl gallic acid, cinnamic acid, acetylsalicylic acid, succinic anhydride or potassium 4-hydroxybulyrate is adopted as raw material and is subjected to a condensation reaction with acetagastrodin to obtain the target product. The preparation is tablets, capsules, injections or lyophilized powder prepared by adding a pharmaceutically acceptable auxiliary agent to the acetagastrodin derivative. The applications comprise the application of the acetagastrodin derivative in preparation of anticoagulation drugs and the application of the acetagastrodin derivative in preparation of drugs for prevention and / or treatment of cardiovascular and cerebrovascular diseases. The acetagastrodin derivative preparation method of the present invention has characteristics of simpleness, easy performing, good reproducibility, and low environmental pollution, and can be used for mass preparation of the compound represented by the following formula.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to an acetylgastrodin derivative 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 25 million every year, ranking first among various causes of death. At present, there are more than 340 million patients with cardiovascular and cerebrovascular diseases in my country, and nearly 4 million people die from cardiovascular and cerebrovascular diseases in China every year, accounting for 48% 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 Applications(China)
IPC IPC(8): C07H15/203C07H15/26C07H1/00A61K31/7034A61K31/706A61P7/02A61P9/00A61P9/10A61P9/08
CPCC07H1/00C07H15/203C07H15/26
Inventor 宋立明白飞杨兆祥张伟张建文刘一丹
Owner KPC PHARM INC
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