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A compound and its preparation method and application

A kind of technology of compound and pharmaceutical preparation, applied in the field of compound and preparation thereof

Active Publication Date: 2016-05-18
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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  • A compound and its preparation method and application
  • A compound and its preparation method and application
  • A compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: Preparation of 4-((3,5,6-trimethylpyrazin-2-yl)methoxy)benzyl alcohol

[0050] a. Preparation of intermediate 2-hydroxymethyl-3,5,6-trimethylpyrazine

[0051] The reference (Liu Xinyong. Synthesis of Ligustrazine metabolites in vivo. Journal of Shandong Medical University. 1997, 35(1)) method can easily prepare the compound 2-hydroxymethyl-3,5,6-trimethylpyrazine . The synthetic route is shown in the figure below:

[0052]

[0053] The product is a yellow solid, 1 H-NMR (500MHz, CDCl 3 , δppm): δ4.66 (s, 2H), δ4.31 (s, 1H), δ2.50 (s, 6H), δ2.38 (s, 3H).

[0054] b. Preparation of intermediate 4-((3,5,6-trimethylpyrazin-2-yl)methoxy)benzaldehyde

[0055] In the reaction flask, add 2-hydroxymethyl-3,5,6-trimethylpyrazine (3g, 0.02mol), dissolve in 20mL dichloromethane, add thionyl chloride (3mL, 0.04mol), stirred for 1.5h. After TLC monitors that the reaction is complete, evaporate the solvent and the remaining thionyl chloride to dryness under reduce...

Embodiment 2

[0059] Example 2: Preparation of 4-(3,5,6-trimethylpyrazine-2-yloxy)benzyl alcohol

[0060] a. Preparation of intermediate 2-carboxy-3,5,6-trimethylpyrazine

[0061] The reference (Liu Xinyong. Synthesis of metabolites of ligustrazine in vivo. Journal of Shandong Medical University. 1997, 35 (1)) method, the compound 2-carboxy-3,5,6-trimethylpyrazine can be easily prepared. The synthetic route is shown in the figure below:

[0062]

[0063] The product is a white solid, 1 H-NMR (500MHz, CDCl 3 , δppm): δ10.18 (s, 1H), δ2.89 (s, 3H), δ2.61 (s, 3H), δ2.56 (s, 3H).

[0064] b. Preparation of intermediate 4-(3,5,6-trimethylpyrazine-2-yloxy)benzaldehyde

[0065] In the reaction flask, add 3,5,6-trimethylpyrazine-2-carboxylic acid (13.8g, 0.08mol), DCC (dicyclohexylcarbodiimide, 26g, 0.126mol), DMAP (4-dimethyl Aminopyridine, 0.5g, 0.004mol), p-Hydroxybenzaldehyde (8g, 0.06mol), 100mL of dichloromethane, stirred at room temperature for 24h, after the reaction was complete as...

Embodiment 3

[0068] Example 3: Preparation of 4-nicotinoyloxybenzyl alcohol

[0069] a. Preparation of intermediate 4-nicotinyloxybenzaldehyde

[0070] In the reaction bottle, add nicotinic acid (2.5g, 0.02mol), 20mL of acetone, dropwise add thionyl chloride (4mL, 0.05mol) under ice bath stirring, heat and reflux for 2 hours, evaporate the solvent and oxychloride under reduced pressure Sulfone to obtain 2.7g of nicotinoyl chloride, add 20mL of acetone for later use.

[0071] In another reaction flask, add p-hydroxybenzaldehyde (2.4g, 0.02mol), 20mL acetone, triethylamine (3mL, 0.02mol), and add the above-prepared nicotinoyl chloride (2.7g, 0.02mol) dropwise under stirring in an ice bath ) in acetone solution. The mixture was heated to 60° C. and reacted for 2 h. After the reaction was completed as monitored by TLC, the reaction solution was cooled to room temperature, filtered, and the filter cake was washed three times with acetone. The filtrate was concentrated under reduced pressure ...

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Abstract

The present invention relates to the field of drug synthesis, and discloses a compound, a preparation method and applications thereof. According to the present invention, the compound has the structure represented by a formula I or formula II, wherein RB is a compound residue having biological activity; the preparation method of the compound represented by the formula I or formula II has characteristics of easy performing, good reproducibility and low environmental pollution, and can be used for large scale preparation of the compound represented by the formula I or formula II; and the compound represented by the formula I or formula II is the compound having the completely-new structure, has effects of significant vasodilatation, anticoagulation and anti-ischemia-reperfusion injury, and can be used for preparation of drugs for prevention or treatment of cardiovascular and cerebrovascular diseases and anticoagulation drugs. The formula I and the formula II are defined in the instruction.

Description

technical field [0001] The present invention relates to the field of drug synthesis, in particular to a compound and its preparation method 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 "silent evil spirits" of people's ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/12C07D241/24C07D213/80C07D213/803C07C69/86C07C67/29C07C203/04C07C201/02A61K31/4965A61K31/4406A61K31/235A61P7/02A61P9/00A61P9/08A61P9/10
CPCC07C67/29C07C69/86C07C201/02C07C203/04C07D213/80C07D213/803C07D241/12C07D241/24
Inventor 宋立明白飞杨兆祥
Owner KPC PHARM INC