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17-Hydro-9-dehydroandrographolide-3-sulfate compound, preparation method and pharmaceutical use thereof

A technology of andrographolide, sulfate ester, applied in the directions of drug combination, antipyretic, organic chemistry, etc., can solve the problems such as solubility and stability are not particularly good, and achieve the guarantee of pharmacological activity, good water solubility and high productivity. Effect

Active Publication Date: 2015-08-05
JIANGZI QINGFENG PHARMACEUTICALS INC
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally, after extracting andrographolide, it is prepared into injections of various water-soluble derivatives, such as adding sulfuric acid with sodium sulfite or adding reaction with sodium bisulfite, to obtain water-soluble sulfonate, sodium bisulfite andrographolide (Lianbizhi Injection), monopotassium succinate half ester, refined from andrographolide through esterification, dehydration, and salt formation 14-dehydroxy-11,12-didehydroandrographolide-3,19- Potassium disuccinate half ester sodium salt (Yanhuning injection) or 14-dehydroxy-11,12-didehydroandrographolide-3,19-disuccinate half ester monopotassium salt, but the above salts are in water Solubility and stability are not particularly good

Method used

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  • 17-Hydro-9-dehydroandrographolide-3-sulfate compound, preparation method and pharmaceutical use thereof
  • 17-Hydro-9-dehydroandrographolide-3-sulfate compound, preparation method and pharmaceutical use thereof
  • 17-Hydro-9-dehydroandrographolide-3-sulfate compound, preparation method and pharmaceutical use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0068] Get andrographolide, add 5.5 times the amount of acetic anhydride (62%) and glacial acetic acid (38%) to dissolve, and under stirring, slowly add 4.5 times the amount of sulfuric acid dropwise at a rate of 1.6ml per minute for 1g andrographolide (52%) and glacial acetic acid (48%), mix evenly, adjust the temperature of the reactor at 16° C., and place it for 90 minutes for sulfonation. Add an equal amount of purified water, stir well, adjust the pH to about 7.0 with 33% NaOH, add 95% ethanol to make the alcohol content reach more than 82%, recover ethanol under reduced pressure, and separate the aqueous solution through macroporous adsorption resin and ODS column chromatography. Gradient elution with water: ethanol, the proportion of water is 80-20%, the proportion of ethanol is 20-80%, the eluate is collected in sections, the same components are combined, and crystallized to obtain 17-hydrogen-9-dehydroandrographis paniculata Sodium lactone-3-sulfate, its sodium salt f...

Embodiment 2

[0076] Get andrographolide, add 5.5 times the amount of acetic anhydride (60%) and glacial acetic acid (40) to dissolve, and under stirring, add 3.5 times the amount of sulfuric acid (52%) by spraying at a speed of 2.1ml per minute with 1g andrographolide Mix with glacial acetic acid (48%), adjust the temperature of the reaction kettle at 17°C, place it for 80 minutes for sulfonation, add an equal amount of purified water, pour it into saturated sodium chloride solution, and pass through macroporous adsorption resin, Sephadex LH-20 column chromatography separation, gradient elution with water: methanol, the ratio of water is 80-20%, the ratio of methanol is 20-80%, the eluate is collected in sections, the same components are combined, crystallized, and 17 - Sodium Hydrogen-9-Dehydroandrographolide-3-sulfate.

Embodiment 3

[0078] Get andrographolide, add 4.5 times the amount of acetic anhydride to dissolve, and under stirring, add 3.2 times the amount of sulfuric acid (55%) and glacial acetic acid (45%) by atomization at a rate of 2.1 ml per minute for 1 g of andrographolide , Mix well, adjust the temperature of the reactor at 16°C, and place it for 90 minutes for sulfonation. The reactant was poured into a saturated sodium chloride solution, the precipitate was washed with a saturated sodium chloride solution and water respectively, the solid was refluxed with chloroform, the insoluble was dissolved by adding absolute ethanol, the alcohol insoluble was removed, the ethanol was recovered, and crystallized to obtain Sodium 17-hydro-9-dehydroandrographolide-3-sulfate.

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PUM

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Abstract

The invention discloses 17-hydrogen-9-dehydro-andrographolidume-3-disulfate or salt thereof, a preparation method thereof, and antipyretic, anti-inflammatory and antiviral purposes of the 17-hydrogen-9-dehydro-andrographolidume-3-disulfate or the salt thereof. The 17-hydrogen-9-dehydro-andrographolidume-3-disulfate or the salt thereof formed by the preparation method does not change chemical properties of andrographolidume, the 17-hydrogen-9-dehydro-andrographolidume-3-disulfate or the salt thereof has the advantages of being good in water-solubility, high in heat stability, small in hemoclasis, and the like, and pharmacoactive effects of andrographolidume pure natural medicine are guaranteed to the greatest extent. In addition, medicine and pharmaceutical research workers cannot know the good purposes of 17-hydrogen-9-dehydro-andrographolidume-3-sodium disulfate in advance on the premise that related experiments are not conducted.

Description

technical field [0001] The invention relates to a 17-hydrogen-9-dehydroandrographolide-3-sulfate compound, a preparation method and a medicinal use thereof. Background technique [0002] Andrographis paniculata is the dry aerial part of Andrographis paniculata (Burm.f.) Nees of the Acanthaceae plant. Chemical composition and pharmacological experiments show that the active ingredients of Andrographis paniculata are mainly diterpenoids represented by andrographolide [National Traditional Chinese Medicine Authority. Chinese Materia Medica Volume 7. Shanghai: Shanghai Science and Technology Press, 1999: 439], the structure of andrographolide is: [0003] [0004] Molecular formula: C 20 h 30 o 5 , is a colorless square crystal, m.p.230-232℃, [α] 0 20 -126°(c0.2, H 2 O). Very bitter taste, soluble in methanol, ethanol, propanol, pyridine, slightly soluble in chloroform, ether, hardly soluble in water and petroleum ether. Therefore, oral preparations usually make table...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/60A61K31/365A61P29/00A61P31/04A61P31/12A61P31/16G01N30/02
Inventor 杨小玲吕武清谢宁唐春山刘地发程帆李志勇刘荛琦廖祝元刘艳红
Owner JIANGZI QINGFENG PHARMACEUTICALS INC
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