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Andrographolide derivatives and their preparation methods and uses

A technology of andrographolide and pharmaceutical preparations, applied in the field of medicine, can solve the problems of virus mutation, failure to meet clinical needs, limited number of drugs for viral respiratory tract infections, etc.

Active Publication Date: 2018-07-03
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] It can be found that the number of drugs currently used clinically for the treatment of viral respiratory tract infections is very limited, which is far from meeting the clinical needs
Moreover, due to the extensive clinical application of existing drugs, the virus has mutated, resulting in varying degrees of drug resistance to these drugs.

Method used

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  • Andrographolide derivatives and their preparation methods and uses
  • Andrographolide derivatives and their preparation methods and uses
  • Andrographolide derivatives and their preparation methods and uses

Examples

Experimental program
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Effect test

Embodiment 1

[0059] Embodiment 1: the preparation of compound of the present invention

[0060] Preparation of 3α,19-dihydroxy 8,9-didehydro-17-(3-thymidyl)-14-deoxyandrographolide (compound 1 for short):

[0061] Using andrographolide as a raw material, in the presence of 4g of anhydrous ZnCl2, andrographolide (10g, 28.55mmol) and 40ml of acetic anhydride were heated to reflux, and the reaction was continued until the reaction solution was clear. Pour the reaction solution into ice water, stir vigorously, filter with suction, wash the filter cake with water until neutral, and recrystallize the filter cake to obtain 12.5 g of fine 3α,14,19-triacetylandrographolide, with a yield of 91.8%. Dissolve it in 20ml methanol, add 0.4g NaBH at room temperature 4 , continue to react for 5 hours. The reaction solution was poured into ice water, stirred vigorously, filtered with suction, and the filter cake was vacuum-dried and recrystallized to obtain 6.5 g of 3α,19-diacetyl-14-deoxyandrographolide...

Embodiment 2

[0090] The anti-respiratory virus research of embodiment 2 product of the present invention

[0091] 1. Materials

[0092] Strain: Influenza A virus (A3 / Jingke / 30 / 95), provided by the Shanghai Municipal Health and Epidemic Prevention Station, and preserved by the Antiviral Laboratory of Fudan University in Shanghai.

[0093] Cell model: dog kidney cells MDCK cells (passage preserved by Antiviral Laboratory of Fudan University, Shanghai).

[0094] 2. Drug Cytotoxicity Test

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Abstract

The invention discloses an andrographolide derivative and a preparation method and application thereof, belongs to the technical field of medicines, and relates to a novel compound with respiratory virus activity resistance, an isomer of the compound or salt capable of being accepted pharmaceutically, a medicine composition containing the compound, a preparation method of the medicine composition and application of the compound in the medicine for treating and / or preventing infections caused by respiratory viruses. The compound and the isomer of the compound or the sat capable of being accepted pharmaceutically are shown in the general formula (I), wherein R1, R2 and R3 are specified in the patent claim and the specification.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a new compound with anti-respiratory virus activity, its isomer or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing the compound and a preparation method. As well as the application of these compounds in medicines for treating and / or preventing infections caused by respiratory viruses. Background technique [0002] Respiratory viruses are viruses that can invade the human respiratory tract and cause local lesions of the respiratory tract, or viruses that only use the respiratory tract as an invasion portal and mainly cause lesions of tissues and organs outside the respiratory tract. According to statistics, more than 90% of acute respiratory infections are caused by viruses, especially upper respiratory tract infections are clinically common and frequently-occurring diseases. Viral respiratory infection is easy to cause large-scale spread throug...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/08C07D307/58A61K31/513A61K31/4196A61K31/5377A61K31/365A61K31/4178A61P31/12A61P31/16
CPCC07D307/58C07D405/08
Inventor 陈丽霞袁雷刘清印孙洪信盛雷邱峰
Owner SHENYANG PHARMA UNIVERSITY
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