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Compound of 17-hydrogen-9-dehydrogenation andrographolide-3-sulphate sodium (or potassium) and 17-hydrogen-9-dehydrogenation andrographolide-19-sulphate sodium (or potassium) and preparation drug purposes thereof

A technology of andrographolide and sodium sulfate, which is applied in the direction of drug combination, antipyretics, and pharmaceutical formulations, can solve the problems of poor solubility and stability, and achieve the effect of good solubility and high stability

Inactive Publication Date: 2013-06-19
JIANGZI QINGFENG PHARMACEUTICALS INC
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  • Summary
  • 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 very good

Method used

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  • Compound of 17-hydrogen-9-dehydrogenation andrographolide-3-sulphate sodium (or potassium) and 17-hydrogen-9-dehydrogenation andrographolide-19-sulphate sodium (or potassium) and preparation drug purposes thereof
  • Compound of 17-hydrogen-9-dehydrogenation andrographolide-3-sulphate sodium (or potassium) and 17-hydrogen-9-dehydrogenation andrographolide-19-sulphate sodium (or potassium) and preparation drug purposes thereof
  • Compound of 17-hydrogen-9-dehydrogenation andrographolide-3-sulphate sodium (or potassium) and 17-hydrogen-9-dehydrogenation andrographolide-19-sulphate sodium (or potassium) and preparation drug purposes thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Take andrographolide, add 5.5 times the amount of acetic anhydride (62%) and glacial acetic acid (38%) to dissolve, under stirring, slowly add 4.5 times the amount of sulfuric acid dropwise at a rate of 1 g andrographolide per minute 1.6ml (52%) and glacial acetic acid (48%), mix well, adjust the temperature of the reaction kettle 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 more than 82%, recover the ethanol under reduced pressure, and separate the aqueous solution by macroporous adsorption resin and ODS column chromatography, Elute with a gradient of water: ethanol, the ratio of water is 80-20%, and the ratio of ethanol is 20-80%, the eluate is collected in sections, the same fractions are combined, and crystallized to obtain 17-hydro-9-dehydroandrographis paniculata Sodium lactone-3-sulfate, its sodium salt molecular formula...

Embodiment 2

[0089] Get andrographolide, add 5.5 times the amount of acetic anhydride (60%) and glacial acetic acid (40) to dissolve, under stirring, at a speed of 1g andrographolide per minute 2.1ml, spray and add 3.5 times the amount of sulfuric acid (52%) Mix with glacial acetic acid (48%), adjust the temperature of the reaction kettle at 17°C, place it for 80 minutes to sulfonate, add an equal amount of purified water, pour it into saturated sodium chloride solution, and then pass through macroporous adsorption resin, Sephadex LH-20 column chromatography, eluted with water: methanol gradient, the ratio of water is 80-20%, and the ratio of methanol is 20-80%, the eluate is collected in sections, the same components are combined, and crystallized to obtain 17 - Sodium Hydro-9-dehydroandrographolide-3-sulfate.

Embodiment 3

[0091] Take andrographolide, add 4.5 times the amount of acetic anhydride to dissolve, under stirring, at the speed of 1g andrographolide 2.1ml per minute, atomize and spray add 3.2 times the amount of sulfuric acid (55%) and glacial acetic acid (45%) , Mix well, adjust the temperature of the reactor at 16 ° C, and place it for 90 minutes to sulfonate. The reactant was poured into saturated sodium chloride solution, the precipitate was washed with saturated sodium chloride solution and water respectively, the solid was refluxed with chloroform, the insoluble matter was dissolved in absolute ethanol, the alcohol insoluble matter was removed, the ethanol was recovered, and crystallized to obtain Sodium 17-hydro-9-dehydroandrographolide-3-sulfate.

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Abstract

The invention relates to a compound of 17-hydrogen-9-dehydrogenation andrographolide-3-sulphate sodium (or potassium) and 17-hydrogen-9-dehydrogenation andrographolide-19-sulphate sodium (or potassium), and discloses constitutes of the compound and a preparation method and an analytical method of the compound. The compound has the purposes of preparing drugs which are antipyretic, anti-inflammatory and antivirotic. The compound is used for preparing a dosage form which can be accepted in the field of pharmacy.

Description

technical field [0001] The invention relates to a 17-hydro-9-dehydroandrographolide-3-sulfate sodium (or potassium), 17-hydro-9-dehydroandrographolide-19-sulfate sodium (or potassium) composition and its use in the preparation of medicines. Background technique [0002] Andrographis paniculata is the dry aerial part of Andrographis paniculata (Burm.f.) Nees. The chemical composition and pharmacological experiments show that the active ingredients of Andrographis paniculata are mainly diterpenoids represented by andrographolide [National Traditional Chinese Medicine] Administration. 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 and ether, insoluble in water ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/365C07D307/60A61P29/00A61P31/12A61P31/16A61P43/00G01N30/02
Inventor 吕武清唐春山谢宁杨小玲刘地发李志勇程帆
Owner JIANGZI QINGFENG PHARMACEUTICALS INC
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