Sulfonated derivative of andrographolide and combination of medication

A technology of andrographolide and its derivatives, which is applied in the direction of drug combination, active ingredients of heterocyclic compounds, drug delivery, etc., can solve problems affecting product quality control, difficult to formulate quality standards, and wrong structure identification of andrographolide sulfonated derivatives, etc. To achieve the effect of stable preparation, controllable quality and good water solubility

Active Publication Date: 2005-10-26
JIANGZI QINGFENG PHARMACEUTICALS INC
View PDF2 Cites 42 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The inventor of the present application once applied for "Water-Soluble Andrographolide Sulfonation Process" (Patent No. ZL01131382.x.), in which the identification of the structure of andrographolide sulfonated derivatives was wrong. In fact, after the sulfonation of andrographolide The total sulfonate generated is a mixture, so it is difficult to formulate quality standards and affect the quality control of products

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Sulfonated derivative of andrographolide and combination of medication
  • Sulfonated derivative of andrographolide and combination of medication
  • Sulfonated derivative of andrographolide and combination of medication

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The total sulfonate of andrographolide was prepared by the sulfonation process of andrographolide (see ZL0131382.x.):.

[0045] Extraction of andrographolide:

[0046] Take 1000g of Andrographis paniculata, add 5000ml of ethanol with a concentration of more than 90%, cold soak, the first time is 72 hours, the second time is 24 hours, the cold soaking liquid is pumped into the reflux tank, calculated according to the amount of Andrographis paniculata leaves, add 15-18% Activated carbon, reflux for 2 hours; filter the decolorized liquid after reflux, release the filtrate when it is concentrated to about 10% ethanol, let it stand still for 24 hours to crystallize, soak the crude crystals in ethanol twice continuously, each time not less than 6 hours, filter , adding 8 times the amount of ethanol to the crystals, heating and dissolving, and filtering for 24 hours to obtain white crystals, and vacuum-drying the crystals to obtain andrographolide.

[0047] Sulfonation of and...

Embodiment 2

[0050] Separation and purification of compound 1 and compound 2

[0051] (High-efficiency silica gel plate and silica gel H are produced by Qingdao Ocean Chemical Factory; C18 (ODS column) is a product of Merck; all reagents are of analytical grade. The same below.)

[0052] Take 50g of total sulfonated andrographolide and add 50ml of water to dissolve, filter and put on a pre-treated D101 macroporous resin column, followed by water, 10%, 20%, 30%, 40%, 50%, 80%, 90% ethanol Perform gradient elution.

[0053] Take the 10% ethanol eluate from the D101 macroporous resin column, concentrate it and put it on the ODS column, first elute with 20% methanol, and then elute with 25% methanol.

[0054] Concentrate the 20% methanol eluate, recrystallize with methanol, filter, and dry the crystals in vacuum (60°C) to obtain compound 1. Concentrate the 25% methanol eluate, recrystallize methanol, filter, and dry the crystals in vacuum (60°C) to obtain compound 2 .

[0055] Physicochemic...

Embodiment 3

[0070] Separation and purification of compound 3 and compound 5

[0071] Take the 20% ethanol eluate from the D101 macroporous resin column in Example 2, concentrate it, and put it on the ODS column, first elute with 30% methanol, and then elute with 35-40% methanol. The 30% methanol eluate was concentrated, then recrystallized with methanol, filtered, and the crystals were vacuum-dried (60° C.) to obtain compound 3.

[0072] After concentration of the 35-40% methanol eluate, the methanol was recrystallized, filtered, and the crystals were vacuum-dried (60° C.) to obtain compound 5.

[0073] Physicochemical properties and spectral data of compound 3

[0074] Chemical Chinese name: 3, 14, 19-trihydroxy-8(9), 12(13)-lysine-15, 16-lactone-19-sulfate.

[0075] Colorless needle crystal (methanol), easily soluble in methanol and water, slightly soluble in acetone, insoluble in chloroform, ether and petroleum ether.

[0076] Molecular formula: C 20 h 30 o 11 S 2 , molecular we...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The present invention discloses II kinds of andrographolide sulfonated derivatives with the actions of resisting bacteria, relieving inflammation and reducing fever and medicine composition containing them. They can be used for preparing freeze-dried powder, injection or oral preparation, and can be used for curing the diseases of pneumonia, bronchitis, tonsillitis and bacillary dysentery, etc.

Description

technical field [0001] The invention relates to andrographolide sulfonated derivatives with antibacterial, anti-inflammatory and antipyretic effects and pharmaceutical compositions containing them. Background technique [0002] Andrographis paniculata (Burm.f.) Nees is a plant of the genus Andrographis in the family Asteraceae, also known as Yijianxi, Snake Grass, Bitter Grass, and Olive Lotus. It is native to India and is also widely cultivated in Guangdong, Fujian and other regions of my country. Chemical and pharmacological experiments show that the active ingredients of andrographolide are diterpenoids and glucoside derivatives represented by andrographolide, and the structure of andrographolide is: [0003] [0004] Molecular formula: C 20 h m o 5 , is a colorless square or rectangular crystal, m.p.230-232℃, [α] D 20 -126°(c0.2, H 2 O). Very bitter taste, soluble in methanol, ethanol, propanol, pyridine, slightly soluble in chloroform, ether, hardly soluble in...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/92
CPCY02A50/30
Inventor 唐春山叶文才胡永美杨小玲
Owner JIANGZI QINGFENG PHARMACEUTICALS INC
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap