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8-epi-12-epi-isoandrographolidume-19-sulfate, preparation method and purposes of prepared medicine

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, achieves the guarantee of pharmacological activity, the preparation method is simple and convenient, and the stability high effect

Active Publication Date: 2014-12-31
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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  • 8-epi-12-epi-isoandrographolidume-19-sulfate, preparation method and purposes of prepared medicine
  • 8-epi-12-epi-isoandrographolidume-19-sulfate, preparation method and purposes of prepared medicine
  • 8-epi-12-epi-isoandrographolidume-19-sulfate, preparation method and purposes of prepared medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Get andrographolide, add 5 times of amount of acetic anhydride (62%) and glacial acetic acid (38%) to dissolve, and under stirring, add 3.2 times of sulfuric acid in equal proportions by spraying at a rate of 2.2ml per minute for 1g of andrographolide Glacial acetic acid, mix well, adjust the temperature of the reaction kettle at 14°C, place it for 90 minutes for sulfonation, add an equal amount of purified water, then pour it into saturated sodium chloride solution, and then pass through the macroporous adsorption resin, Sephadex LH-20 column layer Analysis and separation, gradient elution with water: methanol, the proportion of water is 80-20%, the proportion of methanol is 20-80%, the eluate is collected in sections, the same components are combined, crystallized, and 8-Table-12- Table - Sodium isoandrographolide-19-sulfate, its sodium salt Molecular formula: C 20 h 29 NaO 8 S, molecular weight: 452.

[0069] Reaction example:

[0070]

[0071] 8-table-12-tabl...

Embodiment 2

[0076] Get andrographolide, add 4.8 times the amount of acetic anhydride (60%) and glacial acetic acid (40%) to dissolve, and under stirring, slowly add 4.2 times the amount of sulfuric acid at a rate of 1.7ml per minute for 1g andrographolide (54%) and glacial acetic acid (46%), mix evenly, adjust the temperature of the reactor at 18°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 40% 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 ratio of water is 80-20%, the ratio of ethanol is 20-80%, the eluate is collected in sections, the same components are combined, crystallized, and 8-table-12-table-iso Sodium andrographolide-19-sulfate.

Embodiment 3

[0078] Get andrographolide, add 4.6 times the amount of acetic anhydride to dissolve, and under stirring, add 3.6 times the amount of sulfuric acid (51%) and glacial acetic acid (49%) by atomization at a rate of 2.4 ml per minute for 1 g of andrographolide , Mix well, adjust the temperature of the reactor at 20°C, and place it 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 8-epi-12-epi-sodium isoandrographolide-19-sulfate.

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Abstract

The invention discloses 8-epi-12-epi-isoandrographolidume-19-sulfate or salt thereof, a preparation method thereof, and antipyretic, anti-inflammatory and antiviral purposes of the 8-epi-12-epi-isoandrographolidume-19-sulfate or the salt thereof. The 8-epi-12-epi-isoandrographolidume-19-sulfate or the salt thereof formed by the preparation method does not change chemical properties of andrographolidume, the 8-epi-12-epi-isoandrographolidume-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 8-epi-12-epi-isoandrographolidume-19-sodium disulfate in advance on the premise that related experiments are not conducted.

Description

technical field [0001] The invention relates to an 8-epi-12-epi-isoandrographolide-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 tablets,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/92A61K31/365A61P29/00A61P31/04A61P31/12A61P31/16G01N30/02
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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