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Kukoamine B salt, preparation method thereof and purpose thereof

A technology of chrysanthemum and its compounds, which are applied in the preparation of carboxylic acid amides, chemical instruments and methods, and the preparation of organic compounds, and can solve problems such as unsure curative effect, septic shock, adverse effects, etc.

Active Publication Date: 2012-05-23
THE FIRST AFFILIATED HOSPITAL OF THIRD MILITARY MEDICAL UNIVERSITY OF PLA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Drug treatment is usually based on the empiric use of non-specific drugs such as glucocorticoids, insulin, and immunomodulators, but the efficacy has not been confirmed
In the 1990s, the anti-lipid A monoclonal antibody HA-1A (Centoxin) was used in the treatment of sepsis after war wounds and burns in the US military during the Gulf War. The drug was also clinically used in some European countries and Japan, but Because it may have adverse effects on septic shock, it failed to obtain the approval of the US FDA in 1992, and then disappeared from the European market
So far, no patents or literature reports have been found on Kuchrysamine B salt and its total chemical synthesis method, nor has it been seen to treat sepsis, especially the treatment of sepsis by simultaneously antagonizing multiple PAMPs (LPS and CpG DNA) report

Method used

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  • Kukoamine B salt, preparation method thereof and purpose thereof
  • Kukoamine B salt, preparation method thereof and purpose thereof
  • Kukoamine B salt, preparation method thereof and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Embodiment 1: Synthesis of Kuchrysamine B malate

[0094]1.1 Experimental method: (1) Weigh 50g of compound f1 and dissolve it in 100ml of hydrobromic acid (concentration: 40%), and heat to 140°C for reaction. TLC monitoring showed that after the reaction was complete, yellow crystals could be precipitated by direct cooling, filtered by suction, and washed with a small amount of petroleum ether to obtain 40 g of compound f2 as a yellow solid. Dissolve 40g of compound f2 in 120ml of DMF, add 116g of potassium carbonate and 86ml of benyl chloride and raise the temperature to 80°C for reaction. TLC monitoring, after the reaction is complete, filter directly, extract with ethyl acetate, wash with water, wash with saturated brine, dry over anhydrous sodium sulfate, filter with suction, and concentrate to obtain compound f3. 14.4g of sodium hydroxide was dissolved in 80ml of water, 85g of compound f3 was added thereto, and 80ml of methanol was added, and the temperature was ...

Embodiment 2

[0118] Embodiment 2: Synthesis of Kuchrysamine B succinate

[0119] 2.1 Experimental method: steps (1) to (10) are the same as steps (1) to (10) in Example 1;

[0120] (11) Weigh 1 g of compound k and 0.71 g of succinic acid in an autoclave, add MeOH: THF: water 3: 1: 1 solution 30 ml to dissolve and clarify, add 0.2 g of Pd / C catalyst, ventilate, and react The system is under the hydrogen pressure of 10MPa, and the temperature is raised to 45°C to react, TLC thin layer monitoring, after the reaction is complete, filter with suction, concentrate until dry to obtain a dark green semi-solid, add 30ml of ethanol, ultrasonically shake, let stand to settle, pour Remove the supernatant, repeat several times, and finally filter with suction to obtain 365 mg of dark green solid powder. The chemical reaction equation is as follows:

[0121]

[0122] 2.2 Experimental results: 365 mg of dark green powdery solid was obtained. UV absorption spectrum: λ max nm=280 (methanol); mass sp...

Embodiment 3

[0124] Example 3: Synthesis of Kuchrysamine B Lactate

[0125] 3.1 Experimental method: steps (1) to (10) are the same as steps (1) to (10) in Example 1;

[0126] (11) Weigh 1g of compound k and 0.5ml of lactic acid in an autoclave, add 30ml of a solution of MeOH:THF:water 3:1:1 to dissolve and clarify, add 0.2g of Pd / C catalyst, ventilate, and make the reaction system Under the hydrogen pressure of 10MPa, heat up to 45°C to react, TLC thin-layer monitoring, after the reaction is complete, filter with suction, concentrate until dry to obtain a yellow semi-solid, add 30ml of ethanol, ultrasonically shake, let it settle, and pour off the upper layer The clear liquid was repeated several times, and finally suction filtered to obtain 340 mg of yellow solid powder. The chemical reaction equation is as follows:

[0127]

[0128] 3.2 Experimental results: 340 mg of yellow powdery solid was obtained. UV absorption spectrum: λ max nm=280 (methanol); mass spectrum: [M+H] + m / z 5...

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PUM

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Abstract

The invention relates to a kukoamine B salt, a preparation method thereof and a purpose of the kukoamine B salt in preparation of medicines for preventing and treating sepsis. Experiments show that the kukoamine B salt has a good inhibition effect on main pathogenic factors mediating the sepsis and can be used to prepare medicines for preventing and treating the sepsis. The kukoamine B salt and various pharmaceutically acceptable carriers and / or diluents can be prepared into various preparations, so an efficient control means is provided for such intractable diseases on condition that definite and effective sepsis treatment measures are clinically lacked at present.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a chrysamine B salt, a preparation method thereof, and an application of the chrysamine B salt in the preparation of medicines for preventing and treating sepsis. Background technique [0002] Sepsis is an infectious agent-mediated systemic inflammatory response syndrome (systemic inflammatory response syndrome, SIRS), which is a common complication in patients with burns, trauma, tumors and infectious diseases, and has become a globally recognized cause of intensive care unit disease. The leading cause of death in (ICU) patients. The existing clinical treatment methods for sepsis are mainly the early use of antibiotics and the correction of ischemic hypoxic damage, and the conventional treatment of organ failure and shock. There is no specific treatment. Drug treatment is usually based on empirical use of non-specific drugs such as glucocorticoids, insulin, and im...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/34C07C231/12A61K31/165A61P29/00
CPCC07C59/255C07C59/245C07C57/145C07C309/30C07C309/04C07C59/08C07C229/24C07C53/08C07C55/10C07C235/34C07C53/10C07C53/122C07C53/124C07C55/06C07C55/08C07C55/14C07C57/15C07C57/44C07C59/265C07C59/50C07C63/06C07C309/25A61P29/00A61P31/04
Inventor 郑江郑新川刘鑫周红王宁曹红卫李彦鲁永玲赵苛岑杨景程杨阳祝元锋卫国黄敏
Owner THE FIRST AFFILIATED HOSPITAL OF THIRD MILITARY MEDICAL UNIVERSITY OF PLA
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