Preparing method of anti-influenza virus preparation

A technology for anti-influenza virus and preparations, which is applied in the field of preparation of anti-influenza virus preparations, can solve the problems of rimantadine synthesis steps, environmental protection, long time, etc., and achieve cold symptoms relief, less by-products, and mild reaction conditions Effect

Inactive Publication Date: 2019-02-26
赵旭萌
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthetic steps of this rimantadine are many, the time is long, and it is not environmentally friendly

Method used

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  • Preparing method of anti-influenza virus preparation
  • Preparing method of anti-influenza virus preparation

Examples

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Effect test

Embodiment 1

[0027] A preparation method of an anti-influenza virus preparation, comprising the preparation of 1-bromoadamantane, the preparation of adamantanecarboxylic acid, the preparation of adamantane carboxylic acid chloride, the preparation of adamantane methyl ketone, the preparation of 1-adamantane methyl ketone oxime, and the preparation of rimantadine hydrochloride Preparation, preparation of anti-influenza virus preparations, the specific steps include:

[0028] Preparation of 1-bromoadamantane: Add 30g of adamantane and 24mL of liquid bromine successively to the reaction flask, react at 85°C for 6h, then raise the temperature to 110°C, react in an oil bath for 3h, leave it overnight, recover the liquid bromine by distillation, and use 20 mL of saturated sodium bisulfite solution was used to reduce the remaining bromine, filtered, and the filter cake was washed with water until neutral, dried, and recrystallized from methanol to obtain 44 g of light yellow crystals with a yield ...

Embodiment 2

[0036] A preparation method of an anti-influenza virus preparation, comprising the preparation of 1-bromoadamantane, the preparation of adamantanecarboxylic acid, the preparation of adamantane carboxylic acid chloride, the preparation of adamantane methyl ketone, the preparation of 1-adamantane methyl ketone oxime, and the preparation of rimantadine hydrochloride Preparation, preparation of anti-influenza virus preparations, the specific steps include:

[0037] Preparation of 1-bromoadamantane: In the reaction flask, add adamantane and excess liquid bromine successively, react at 80°C for 6 hours, then raise the temperature to 120°C, react in an oil bath for 3 hours, leave it overnight, recover liquid bromine by distillation, and then use saturated Restore the remaining bromine with sodium bisulfate solution, filter, wash the filter cake with water until neutral, dry, and recrystallize from methanol to obtain light yellow crystals, which are 1-bromoadamantane;

[0038] Prepara...

Embodiment 3

[0045] A preparation method of an anti-influenza virus preparation, comprising the preparation of 1-bromoadamantane, the preparation of adamantanecarboxylic acid, the preparation of adamantane carboxylic acid chloride, the preparation of adamantane methyl ketone, the preparation of 1-adamantane methyl ketone oxime, and the preparation of rimantadine hydrochloride Preparation, preparation of anti-influenza virus preparations, the specific steps include:

[0046] Preparation of 1-bromoadamantane: In the reaction bottle, add adamantane and excess liquid bromine successively, react at 90°C for 7 hours, then raise the temperature to 120°C, react in an oil bath for 4 hours, leave it overnight, recover liquid bromine by distillation, and then use saturated Restore the remaining bromine with sodium bisulfate solution, filter, wash the filter cake with water until neutral, dry, and recrystallize from methanol to obtain light yellow crystals, which are 1-bromoadamantane;

[0047] Prepar...

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Abstract

A preparing method of an anti-influenza virus preparation is disclosed. The method includes preparing 1-bromo adamantane, preparing adamantane carboxylic acid, preparing adamantanecarbonyl chloride, preparing adamantyl methyl ketone, preparing 1-adamantyl methyl ketoxime, preparing rimantadine hydrochloride and preparing the anti-influenza virus preparation. The adamantyl methyl ketone is preparedby steps of adding trimethyl aluminum and cerium formate into a flask, adding dropwise a benzene solution of adamantanecarbonyl chloride so that the adamantanecarbonyl chloride reacts with the trimethyl aluminum to generate the adamantyl methyl ketone, pouring the reaction solution into ice water after the reaction is finished, and performing filtration and drying to obtain light yellow precipitate that is the adamantyl methyl ketone. Beneficial effects of the method are that the method has mild conditions, simple and feasible process and high product yield, and the anti-influenza virus preparation prepared by the method can effectively prevent and treat the influenza A/B virus infection, and can effectively alleviate symptoms of cold.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to a preparation method of an anti-influenza virus preparation. Background technique [0002] Influenza is an acute febrile respiratory infectious disease caused by influenza virus. It is transmitted through droplets. The typical clinical manifestations are chills, high fever, headache, body aches, weakness and other systemic poisoning symptoms, while the respiratory symptoms are mild. [0003] Riantadine hydrochloride is an amino derivative of saturated tricyclodecane, the chemical name is α-methyltricyclo[3,3,1,1]decane-1-methylamine hydrochloride, Bristol Myers Squibb Company, USA Research and development, first launched in France in 1987, in 1993 the US FDA approved for the prevention and treatment of influenza A virus infection, the clinical efficacy is better than amantadine. Such compounds have antiviral effects. The mechanism of action of rimantadine is to change the sur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/52C07C211/19A61K31/13A61K31/616A61K31/5415A61K31/137A61K36/78A61P31/16A61P29/00A61P11/14B01J31/38
CPCC07C17/10A61K31/13A61K31/137A61K31/5415A61K31/616A61K36/78A61P11/14A61P29/00A61P31/16B01J31/38B01J2231/643C07C45/455C07C51/353C07C51/60C07C209/52C07C249/08C07C2603/74C07C23/38C07C61/135C07C49/323C07C251/42C07C211/19A61K2300/00
Inventor 赵旭萌
Owner 赵旭萌
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