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Method for preparing antivirus andrographolide derivative

A technology of andrographolide and andrographolide is applied in the field of medicine to achieve the effects of stable drug quality and simple preparation process

Inactive Publication Date: 2013-08-14
福州璐珈医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there is no report on the use of the andrographolide rimantidine salt for the treatment of upper respiratory tract infection, pneumonia, bronchitis, influenza, etc.

Method used

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  • Method for preparing antivirus andrographolide derivative
  • Method for preparing antivirus andrographolide derivative
  • Method for preparing antivirus andrographolide derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0016] Yanhuning rimantadine synthesis process:

[0017] 1) Riantadine:

[0018] The structural formula is as follows: CAS1501-84-4

[0019]

[0020] Physical and chemical properties: slightly soluble in water, soluble in chloroform, MP300℃. Hydrochloride was dissolved in 5 times ethanol, 18 times chloroform, 2.5 times water. PH3.5-5, 1.87g rimantadine hydrochloride (0.01mol) + 5ml distilled water dissolved, 25% NaOH (1.6ml, theoretical amount) to adjust the pH3-5, a large amount of solid precipitated, washed with water, and dried. MP225~235℃

[0021] 2) Yanhuning:

[0022] The structural formula is as follows:

[0023]

[0024] Andrographolide disuccinic acid half ester C28H36O10MW532.5 measured value MP102~110℃ (literature value 137~140℃).

example 1

[0026] Add 2.67 g (0.005 mol) of andrographolide disuccinic acid half ester into 40 ml of chloroform, and slightly heat (35° C.) to dissolve. Add 1.51 g (0.01 mol) of rimantadine into 30 ml of chloroform and dissolve. Under stirring at room temperature, the rimantadine / chloroform solution was slowly added to the andrographolide disuccinate half ester / chloroform solution. Stirring was continued, and a large number of slightly yellow crystals were precipitated. After standing for 1 hour, it was filtered, dried and pulverized. 3.9 g of light yellow powder was obtained, yield 82%, MP 215-220°C, namely 14-dehydroxy-11,12-didehydroandrographolide-3,19-disuccinic acid half ester rimantadine salt.

example 2

[0028] Add 2.67g (0.005mol) of andrographolide disuccinic acid half ester into 30ml of ethanol, and heat (40°C) to dissolve. Add 1.51 g (0.01 mol) of rimantadine into 20 ml of ethanol to dissolve. Under stirring at room temperature, slowly add the rimantadine / ethanol solution to the andrographolide disuccinate half ester / ethanol solution. Stirring was continued, and a large number of slightly yellow crystals were precipitated. After standing for 1 hour, it was filtered, dried and pulverized. Obtain 4 grams of light yellow powder, yield 83%, HPLC content 98%, MP 215~220 ℃, namely 14-dehydroxyl-11,12-didehydroandrographolide-3,19-disuccinic half ester adamantine Ethylamine salt.

[0029] The salt composed of 14-dehydroxy-11,12-didehydroandrographolide-3,19-disuccinic acid half ester and rimantadine is 14-dehydroxy-11,12-didehydroandrographolide- 3,19-disuccinic acid half ester rimantadine salt, its reaction equation is as follows:

[0030]

[0031] Analysis by proton nuc...

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Abstract

The invention discloses an antivirus andrographolidume derivative and the preparation thereof. The derivative is a 14-deshydroxy-11, 12-didehydrogenation andrographolidume-3, 19-disuccinic acid half-ester rimantadine salt which consists of 14-deshydroxy-11, 12-didehydrogenation andrographolidume-3, 19-disuccinic acid half-ester and rimantadine. The combination ratio of the 14-deshydroxy-11, 12-didehydrogenation andrographolidume-3, 19-disuccinic acid half-ester and the rimantadine is 1:2 or 1:1. The dosage form can be any one of the existing medical dosage forms which are injection solution, transfusion, powder injection, dropping pills, tablets, dispersible tablets, sustained-release tablets, fast disintegrating oral tablets, capsule, soft capsule, granules, emulsion and targeting preparation. The preparation is used for treating upper respiratory tract infection, pneumonia, bronchitis, influenza, and the like, and has obvious effect of improving respiratory state, antibiosis, antipyretic action, antiviral effect and the like. The preparing process is simple and the medicine quality is steady.

Description

Technical field: [0001] The invention belongs to the technical field of medicine. In particular, it relates to a salt composed of 14-dehydroxy-11,12-didehydroandrographolide-3,19-disuccinic acid half esters and rimantadine for anti-infection, anti-virus, antipyretic and analgesic Compounds, methods of preparation and uses thereof. Background technique: [0002] Andrographis paniculata is the dry aerial part of Andrographis Paniculata (Burm.f.) Nees, a plant of the Acanthaceae family. It has the functions of clearing heat and detoxifying, cooling blood, and reducing swelling. Its main active ingredient is andrographis lactone. Its derivatives after esterification, dehydration, and salt formation can inhibit early capillary permeability increase, inflammatory exudation, and edema, and can specifically stimulate the pituitary-adrenal cortex function, promote the release of ACTH, and increase the anterior pituitary gland. The biosynthesis of ACTH in the middle; it has the func...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/58A61K31/365A61P31/00A61P29/00
Inventor 谢开智谢开书罗振福李玲王浩
Owner 福州璐珈医药科技有限公司
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