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17-hydrogen-9-dehydro-andrographolidume-19-sulfate, preparation method and purposes of medicine prepared by the same

A technology of andrographolide and sulfate ester, which is applied in drug combination, antipyretics, organic chemistry, etc., can solve the problems of large clinical side effects, poor solubility, and stability, and achieve small hemolysis and ensure pharmacological activity , good solubility

Active Publication Date: 2013-06-19
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 The solubility and stability are not particularly good, and the clinical side effects are large

Method used

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  • 17-hydrogen-9-dehydro-andrographolidume-19-sulfate, preparation method and purposes of medicine prepared by the same
  • 17-hydrogen-9-dehydro-andrographolidume-19-sulfate, preparation method and purposes of medicine prepared by the same
  • 17-hydrogen-9-dehydro-andrographolidume-19-sulfate, preparation method and purposes of medicine prepared by the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Get andrographolide, add 5.6 times the amount of acetic anhydride (60%) and glacial acetic acid (40%) to dissolve, and under stirring, slowly add 4.5 times the same amount of sulfuric acid dropwise at a rate of 2.0ml per minute for 1g of andrographolide Glacial acetic acid, mix well, adjust the temperature of the reaction kettle at 18°C, and let it stand for 100 minutes for sulfonation. Add an equal amount of purified water, stir well, adjust the pH to about 7.0 with 36% 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 fractions are collected, the same fractions are combined, and crystallized to obtain 17-hydrogen-9-dehydroandrographis paniculata Sodium lactone-19-sulfate, the molecular for...

Embodiment 2

[0075]Get andrographolide, add 5.8 times of amount of acetic anhydride (62%) and glacial acetic acid (38%) to dissolve, and under stirring, slowly add 4.4 times of sulfuric acid dropwise at a rate of 1.8ml per minute for 1g of andrographolide (52%) and glacial acetic acid (48%), mix evenly, adjust the temperature of the reactor at 21° C., and place it for 100 minutes for sulfonation. Add an equal amount of purified water, stir well, adjust the pH to about 7.0 with 36% 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-19-sulfate.

Embodiment 3

[0077] Get andrographolide, add 5.6 times the amount of acetic anhydride to dissolve, and under stirring, add 4.2 times the amount of sulfuric acid (51%) and glacial acetic acid (49%) by atomization at a rate of 2.6 ml per minute for 1 g of andrographolide , Mix well, adjust the temperature of the reactor at 18°C, and let it stand for 80 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-19-sulfate.

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PUM

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Abstract

The invention discloses 17-hydrogen-9-dehydro-andrographolidume-19-sulfate or salt thereof, a preparation method thereof, and antipyretic, anti-inflammatory and antiviral purposes of the 17-hydrogen-9-dehydro-andrographolidume-19-sulfate or the salt thereof. The 17-hydrogen-9-dehydro-andrographolidume-19-sulfate or the salt thereof formed by the preparation method does not change chemical properties of andrographolidume, the 17-hydrogen-9-dehydro-andrographolidume-19-sulfate 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-19-sodium sulfate in advance on the premise that related experiments are not conducted.

Description

technical field [0001] The invention relates to a 17-hydrogen-9-dehydroandrographolide-19-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 tabl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/60A61K31/365A61P29/00A61P31/04A61P31/12A61P31/16
Inventor 唐春山谢宁吕武清杨小玲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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