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14-deoxy-14,15-didehydro andrographolide derivatives and medicine composition and application thereof

A technology of andrographolide, didehydrogenation, applied in the directions of pharmaceutical formulations, medical preparations containing active ingredients, organic active ingredients, etc.

Inactive Publication Date: 2014-04-23
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] At present, there is no report on the 14-deoxy-14,15-didehydroandrographolide derivative (I) provided by the present invention and its pharmaceutical composition as an active ingredient, and there is no application of the required derivative or its pharmaceutical composition Reports in the preparation or treatment of hepatitis B drugs

Method used

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  • 14-deoxy-14,15-didehydro andrographolide derivatives and medicine composition and application thereof
  • 14-deoxy-14,15-didehydro andrographolide derivatives and medicine composition and application thereof

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Experimental program
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Effect test

preparation Embodiment 1

[0022] Preparation of raw material andrographolide:

[0023] Take 10 kg of the whole plant of Andrographis paniculata and grind it, extract three times with 30 kg of 90% ethanol, each time for 3 hours, combine the ethanol extract, concentrate to a volume of 10 liters, extract the concentrated solution three times with ethyl acetate, each time 18 liters, combine acetic acid Ethyl extract, ethyl acetate was recovered to obtain 336 g of ethyl acetate extract.

[0024] 336 grams of ethyl acetate was dissolved in acetone, adsorbed on 600 grams of silica gel, evaporated to dryness at room temperature, passed through a 60-100 mesh sieve, and set aside. Take 3000 grams of column chromatography silica gel (200-300 mesh, Qingdao Meigao Company), and fill it in a glass chromatography column with a mixed solvent of ethyl acetate-petroleum ether (40:60) by wet method (column diameter 18cm, height of filled silica gel 28cm), after the sample was loaded, it was eluted with a mixed solvent o...

preparation Embodiment 2-3

[0036] According to Example 1, add 0.4mmol (200mg) andrographolide, 0.2mmol (34mg) 4-dimethylaminopyridine (DMAP) and 0.6mmol corresponding acid into a 10mL round bottom flask, then add 5ml of anhydrous N,N - Dimethylformamide, after stirring to dissolve, add 1.0mmol (206mg) N-dicyclohexylcarbodiimide (DCC) under ice-bath conditions and stir, and the reaction temperature rises to room temperature. After the reaction of andrographolide was detected by TLC, the reaction solution was filtered, washed three times with dilute hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated saline solution, and then dried over anhydrous sodium sulfate. The solvent was recovered under reduced pressure to obtain a crude product, which was passed through a silica gel column layer Analysis and eluting with ethyl acetate-petroleum ether (30:70-40:60) to prepare 14-deoxy-14,15-didehydroandrographolide derivatives (2-3) with the following structure:

[0037] Compound 2 and 3...

preparation Embodiment 1

[0075] According to the method of Preparation Example 1, 14-deoxy-14,15-didehydroandrographolide derivatives were first prepared, dissolved with a small amount of DMSO, added water for injection as usual, finely filtered, potted and sterilized to make injections .

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Abstract

The invention belongs to the technical field of medicines and relates to 14-deoxy-14,15-didehydro andrographolide derivatives (1-3) shown in a general formula (I), and a medicine composition of the derivatives, a preparation method and application of the derivatives and the medicine composition of the derivatives to preparation of medicines for resisting hepatitis B.

Description

technical field [0001] The present invention belongs to the technical field of medicines, in particular, it relates to 14-deoxy-14,15-didehydroandrographolide derivatives (1-3), a pharmaceutical composition containing it as an active ingredient, a preparation method thereof, and the Application of derivatives and pharmaceutical compositions thereof in the preparation of anti-hepatitis B drugs. Background technique [0002] Hepatitis B is an infectious disease caused by Hepatitis B virus (HBV), which mainly affects the liver and causes multiple organ damage. Hepatitis B virus infection is a global infectious disease. There are about 360 million chronically infected people in the world, and about 600,000 people die each year due to HBV infection. China is a high-endemic area of ​​hepatitis B virus. According to the serum epidemiological data of hepatitis B in 2006, the carrier rate of hepatitis B virus surface antigen in my country is 7.18%, that is, there are 93 million carr...

Claims

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Application Information

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IPC IPC(8): C07D405/12C07D307/68C07D409/12A61K31/443A61K31/365A61K31/381A61P31/20
CPCC07D307/68C07D405/12C07D409/12
Inventor 陈纪军陈浩耿长安马云保黄晓燕张雪梅
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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