Use of rimantadine Schiff base

A technology of rimantadine Schiff base and rimantadine is applied in the directions of antiviral agents, antibacterial drugs, drug combinations, etc., to achieve the effects of less by-products, mild reaction conditions, and high product yields

Inactive Publication Date: 2019-01-18
赵旭萌
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, using rimantadine and cinnamaldehyde as raw materials to synthesize rimantadine Schiff base has not been reported yet.

Method used

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  • Use of rimantadine Schiff base
  • Use of rimantadine Schiff base
  • Use of rimantadine Schiff base

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A kind of purposes of rimantadine Schiff base, the prepared rimantadine Schiff base is rimantadine cinnamaldehyde Schiff base, its stereoisomer or pharmaceutically accessible salt, the chemical structural formula is:

[0026]

[0027] A kind of purposes of rimantadine Schiff base, the synthetic method of prepared rimantadine Schiff base comprises the steps:

[0028] Preparation of adamantanecarboxylic acid chloride: Add 1.8g of adamantanecarboxylic acid and 3.6mL of thionyl chloride into a three-necked flask, heat to 80°C, reflux for 2 hours, recover thionyl chloride by vacuum distillation, and then add 5mL×2 of benzene for extraction. Gained extract is directly used for next step reaction;

[0029] Preparation of adamantanemethyl ketone: Add 0.10g trimethylaluminum and 0.01g cerium formate to a three-necked flask, then add a benzene solution of adamantanecarbonyl chloride dropwise at 0.25mL / min to make adamantanecarbonyl chloride and trimethylaluminum The reaction ...

Embodiment 2

[0034] A kind of purposes of rimantadine Schiff base, the prepared rimantadine Schiff base is rimantadine cinnamaldehyde Schiff base, its stereoisomer or pharmaceutically accessible salt, the chemical structural formula is:

[0035]

[0036] A kind of purposes of rimantadine Schiff base, the synthetic method of prepared rimantadine Schiff base comprises the steps:

[0037] Preparation of adamantanecarboxylic acid chloride: Add adamantanecarboxylic acid and thionyl chloride into a three-necked flask, heat to 80°C, reflux for 2 hours, recover thionyl chloride by vacuum distillation, then add benzene for extraction, and the obtained extract is directly used in the following one step reaction;

[0038]Preparation of adamantane methyl ketone: Add trimethylaluminum and cerium formate to a three-necked flask, and then drop a benzene solution of adamantanecarbonyl chloride at 0.1mL / min to react adamantanecarbonyl chloride and trimethylaluminum to form adamantane Methyl ketone, aft...

Embodiment 3

[0043] A kind of purposes of rimantadine Schiff base, the prepared rimantadine Schiff base is rimantadine cinnamaldehyde Schiff base, its stereoisomer or pharmaceutically accessible salt, the chemical structural formula is:

[0044]

[0045] A kind of purposes of rimantadine Schiff base, the synthetic method of prepared rimantadine Schiff base comprises the steps:

[0046] Preparation of adamantanecarboxylic acid chloride: Add adamantanecarboxylic acid and thionyl chloride into a three-necked flask, heat to 80°C, reflux for 2 hours, recover thionyl chloride by vacuum distillation, then add benzene for extraction, and the obtained extract is directly used in the following one step reaction;

[0047] Preparation of adamantane methyl ketone: Add trimethylaluminum and cerium formate to a three-necked flask, and then drop a benzene solution of adamantanecarbonyl chloride at 0.5mL / min to react adamantanecarbonyl chloride and trimethylaluminum to form adamantane Methyl ketone, af...

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Abstract

The invention discloses a use of rimantadine Schiff base. Rimantadine ethylamine Schiff base was prepared by chlorination of adamantane formic acid with thionyl chloride, alkylation in the presence oftrimethyl aluminum and cerium formate, oximation to ketoxime, reduction with palladium-carbon and aldehyde-amine condensation reaction with cinnamaldehyde to obtain adamantane ethylamine cinnamaldehyde Schiff base. The reaction route of the invention changes the route of synthesizing adamantane methyl ketone, and cerium formate is used for assisting the reaction of trimethyl aluminum, so that thereaction conditions are mild and the by-products are few. The synthesis method has the advantages of simple and feasible process, low catalyst consumption, environmental protection and high product yield. The adamantine Schiff base prepared by the invention has antibacterial activity, antiviral activity and antitumor activity, and can be used in the fields of medicine, daily chemistry, food and the like, and has the potential to be used as an antibacterial agent, an antiviral agent and an antineoplastic agent.

Description

technical field [0001] The invention relates to the field of medicines, in particular to the use of rimantadine Schiff base in antibacterial, antiviral and antitumor preparations. Background technique [0002] Rimantadine, an amino derivative of saturated tricyclodecane, chemically named α-methyltricyclo[3,3,1,1]decane-1-methylamine, has antiviral and sedative effects, and is used in clinical It is also used to treat sudden severe pain and measles, and it is characterized by fast absorption and small side effects. Amantadine was developed by Bristol Myers Squibb Company of the United States, and was first launched in France in 1987. In 1993, the US FDA approved it for the prevention and treatment of influenza A virus infection, and its clinical efficacy is better than that of amantadine. The mechanism of action of rimantadine is to change the surface charge of the host cell, inhibit the process of the virus penetrating into sensitive cells and releasing nucleic acid, and in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/135A61K31/137A61P31/04A61P31/12A61P35/00
CPCA61K31/135A61K31/137A61P31/04A61P31/12A61P35/00
Inventor 赵旭萌
Owner 赵旭萌
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