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A kind of preparation method of dehydroandrographolide and its amino acid ester derivatives

A technology for dehydroandrographolide and andrographolide, which is applied in the field of medicine, can solve the problems of large demand for dehydroandrographolide, complicated separation process, and long time-consuming, so as to avoid adverse reactions, stable and controllable process, and easy operation Effect

Active Publication Date: 2016-04-27
HEILONGJIANG ZBD PHARMA +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] Chinese patent application publication specification (publication number CN1810794A), its method is to carry out semi-synthesis with the catalysis of inorganic matter, but there is no test data such as yield in the embodiment
There are not many existing methods for semi-synthesizing dehydroandrographolide from andrographolide, and the yield is low, the purity is not high, and there are many impurities; it is difficult to obtain high-purity dehydroandrographolide with traditional Chinese medicine extraction and separation methods, and the separation process is complicated , long time-consuming, serious pollution, improper process control and easy to obtain esterification products, etc., the above reasons have caused the situation that dehydroandrographolide has a large demand in the existing market, is expensive, and is not easy to obtain

Method used

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  • A kind of preparation method of dehydroandrographolide and its amino acid ester derivatives
  • A kind of preparation method of dehydroandrographolide and its amino acid ester derivatives
  • A kind of preparation method of dehydroandrographolide and its amino acid ester derivatives

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Embodiment 1

[0058] Embodiment 1: the preparation method of dehydroandrographolide

[0059] Get andrographolide 35.0g (0.1mol), add 60ml pyridine (equivalent to 1.71 times volume of andrographolide weight) and 0.5g aluminum oxide (equivalent to 1.43% of andrographolide weight), stir slowly and heat up to 120 ℃ , reflux reaction for 4 hours, filter after the reaction is completed, then add the filtrate to 200ml water (equivalent to 5.71 times the weight of andrographolide), add and stir synchronously, after adding completely, let it stand for 5 hours, filter, and shower with water for many times The pyridine was washed off, (when the pyridine was detected by HPLC was less than 0.1%), and dried to obtain 32.3 g of dehydroandrographolide, which was off-white. After recrystallization in 100 ml of 60% ethanol, 30.9 g of white needle crystals of dehydroandrographolide were obtained, with a yield of 93.1% and a purity of 99.5%.

Embodiment 2

[0060] Embodiment 2: the preparation method of dehydroandrographolide

[0061] Get andrographolide 35.0g (0.1mol), add 60ml pyridine (equivalent to 1.71 times volume of andrographolide weight) and 0.3g sodium sulfite (equivalent to 0.86% of andrographolide weight), stir slowly and heat up to 115 ℃, Reflux for 5 hours. Filter after completion of the reaction, slowly add the filtrate to 200ml of water (equivalent to 5.71 times the weight of andrographolide), add and stir synchronously, after adding completely, leave standstill for 5 hours, filter, rinse with water several times to remove pyridine, After drying, 32.5 g of dehydroandrographolide was obtained, and the product was off-white. After recrystallization in 100 ml of 70% ethanol, 30.6 g of white needle crystals of dehydroandrographolide were obtained, with a yield of 92.2% and a purity of 99.6%.

Embodiment 3

[0062] Embodiment 3: the preparation method of dehydroandrographolide

[0063] Get andrographolide 35.0g (0.1mol), add 60ml pyridine (equivalent to 1.71 times volume of andrographolide weight) and 0.5g aluminum oxide (equivalent to 1.43% of andrographolide weight) and 0.3g sodium sulfite (equivalent to andrographolide weight 1.43%) 0.86% of the lactone weight), stirred and slowly heated to 125° C., and refluxed for 4 hours. Filter after completion of the reaction, add the filtrate to 200ml of water (equivalent to 5.71 times the weight of andrographolide), add and stir simultaneously, after adding completely, let it stand for 5 hours, filter, rinse with water several times to remove pyridine, and dry , to obtain dehydroandrographolide 32.6g, and the product is off-white. After recrystallization in 100 ml of 60% ethanol, 30.6 g of white needle crystals of dehydroandrographolide were obtained, with a yield of 92.2% and a purity of 99.6%.

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Abstract

The invention relates to a method for preparing an amino-acid ester derivative hydrochloride of dehydrated andrographolide, namely a compound represented by a structure (a formula III) shown in descriptions. The method comprises the steps of carrying out esterification reaction, and deprotecting to produce hydrochloride, thereby finally preparing the amino-acid ester derivative hydrochloride of dehydrated andrographolide. The method for preparing the amino-acid ester derivative of dehydrated andrographolide, disclosed by the invention, is stable and controllable in process, simple and convenient in operation and easy in industrialization; the prepared amino-acid ester derivative of dehydrated andrographolide is high in purity, high in yield and stable in ingredient, so that the occurrence of adverse reaction events can be greatly avoided.

Description

technical field [0001] The invention relates to the technical field of medicine, and relates to a preparation method of dehydroandrographolide and amino acid ester derivatives of dehydroandrographolide. Background technique [0002] Andrographis paniculata (Andrographis paniculata (Burm.f.) Nees) is the dry aerial part of the Acanthaceae plant Andrographis paniculata (Burm.f.) Nees. In India, it is mainly distributed in Guangdong, Fujian, Guangxi, Yunnan, Sichuan, Jiangxi, Jiangsu and other places in China. It is a commonly used traditional Chinese medicine and is included in the first part of the "Chinese Pharmacopoeia" 2010 edition, page 251. [0003] Andrographis paniculata has the functions of clearing away heat and detoxification, cooling blood and reducing swelling. Its main active ingredient is a diterpene lactone compound, such as andrographolide (as shown in formula I) and its derivative dehydroandrographolide and the like. Modern pharmacological studies have show...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/58
CPCC07D307/58
Inventor 方同华周广红贾文娟朱自力徐秀杰
Owner HEILONGJIANG ZBD PHARMA
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