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Amantadine hapten and preparing method and application thereof

A technology of amantadine and hapten, which is applied in the preparation of cyanide reaction, chemical instruments and methods, and the preparation of organic compounds, to achieve the effects of optimizing reaction time, optimizing reaction temperature, and high product yield

Inactive Publication Date: 2019-08-09
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the illegal use of amantadine in poultry farming persists

Method used

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  • Amantadine hapten and preparing method and application thereof
  • Amantadine hapten and preparing method and application thereof
  • Amantadine hapten and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Preparation of 2-(adamantyl)aminoacetic acid:

[0046] a) Preparation of ethyl 2-(adamantyl)aminoacetate: Dissolve 3.04 g of amantadine in 20 mL of DMF, add 3.9 g of ethyl bromoacetate and 5.5 g of K 2 CO 3 , stirred and reacted at 60°C for 16 hours; then added 50mL of water to dilute, and then extracted with ethyl acetate (3×50mL); after the organic phase was combined, it was dried with sodium, and then the solid was filtered out, and the filtrate was concentrated in vacuo and purified by a silica gel column Can obtain ethyl 2-(adamantyl) aminoacetate;

[0047]b) Preparation of 2-(adamantyl)aminoacetic acid: Dissolve 2g of ethyl 2-(adamantyl)aminoacetate in aqueous ethanol (ethanol:water=20:15), add 0.7g NaOH, and stir for 1 hour ; After ethanol was distilled off under reduced pressure, the pH of the solution was adjusted to 5 with 3N HCl; the mixture was concentrated and purified in vacuo to finally obtain 2-(adamantyl)aminoacetic acid.

[0048] c) The synthesis pr...

Embodiment 2

[0052] Preparation of 4-(adamantyl)aminobutyric acid:

[0053] a) Preparation of ethyl 4-(adamantyl)aminobutyrate: Dissolve 5.6g ethyl 4-bromobutyrate in 15mL DMF, add 4.4g amantadine and 8.1g K 2 CO 3 , stirred and reacted at 60°C for 16 hours; then added 100mL of water to dilute, and then extracted with ethyl acetate (3×50mL); after the organic phase was combined, it was dried with sodium, and then the solid was filtered out, and the filtrate was concentrated and purified in vacuo. Obtain ethyl 4-(adamantyl) aminobutyrate;

[0054] b) Preparation of 4-(adamantyl)aminobutyric acid: Dissolve 3g ethyl 4-(adamantyl)aminobutyrate in aqueous ethanol (ethanol:water=20:15), add 0.9g NaOH, and stir for reaction 1 hour; after the ethanol was distilled off under reduced pressure, the pH of the solution was adjusted to 5 with 3N HCl; the mixture was concentrated and purified in vacuo to finally obtain 4-adamantanemethylaminobutyric acid.

[0055] c) The synthesis process steps are as...

Embodiment 3

[0059] Preparation of 8-(adamantyl)aminocaprylic acid:

[0060] a) Preparation of ethyl 8-(adamantyl)aminooctanoate: Dissolve 5.04g amantadine in 15mL DMF, add 9.1g ethyl bromooctanoate and 9.1g K 2 CO 3 , stirred and reacted at 60°C for 16 hours; then added 100mL of water to dilute, and then extracted with ethyl acetate (3×50mL); after the organic phase was combined, it was dried with sodium, and then the solid was filtered out, and the filtrate was concentrated and purified in vacuo. Obtain ethyl 8-(adamantyl)aminooctanoate;

[0061] b) Preparation of 8-(adamantyl)aminocaprylic acid: Dissolve 4g of ethyl 8-(adamantyl)aminocaprylic acid in aqueous ethanol (ethanol:water=1:1), add 0.9g NaOH, and stir for 1 hour ; After removing ethanol, the pH of the solution was adjusted to 5 with 3N HCl; the mixture was concentrated and purified in vacuo to finally obtain 8-(adamantyl)aminocaprylic acid.

[0062] c) The synthesis process steps are as follows:

[0063]

[0064] d) Resu...

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Abstract

The invention relates to the field of preparation of haptens, in particular to an amantadine hapten and a preparing method and application thereof. When the amantadine hapten is prepared, amantadine and bromine polyhydroxyalkanoate serve as raw materials, and through a nucleophilic substitution reaction, amidogen groups in amantadine molecules are connected with the bromine polyhydroxyalkanoate; then through a hydrolysis reaction, carboxyl groups are introduced to obtain a corresponding product. The amantadine hapten can be coupled with a carrier protein to prepare an artificial antigen, the artificial antigen is prepared into a monoclonal antibody or a polyclonal antibody through an immune animal, and then the monoclonal antibody or the polyclonal antibody can be used for quickly detecting residues of the amantadine in an animal product.

Description

technical field [0001] The invention relates to the field of hapten preparation, in particular to an amantadine hapten and its preparation method and application. Background technique [0002] The molecular formula of Amantadine is C 10 h 17 N, also known as tricyclodecanylamine, is the first antiviral drug approved by the US Food and Drug Administration (FDA). It was launched in the United States in 1966, and domestic production began in 1971. Amantadine plays an antiviral role by interrupting the early replication of the virus. This type of drug has been used clinically for many years. Due to its low economic cost, it is widely used in the prevention and treatment of influenza viruses in humans and even animals. With the widespread application of amantadine, side effects are gradually emerging, including drug resistance, promoting strain mutation, neurotoxicity, etc., posing a serious potential threat to people's health. U.S. FDA prohibited the use of amantadine drugs i...

Claims

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Application Information

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IPC IPC(8): C07C229/14C07C227/08C07C227/18C07K14/765C07K14/77C07K14/795C07K16/44
CPCC07C227/08C07C227/18C07C229/14C07K14/765C07K14/77C07K14/795C07K16/44C07K19/00C07C2603/74
Inventor 王战辉江海洋温凯沈建忠张西亚陈超超段长飞余文博于雪芝
Owner CHINA AGRI UNIV
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