Synthetic methods of 3,6-bis(4-bisfumaroyl aminobutyl)-2,5-diketopiperazine and salt substitute thereof

A bisfumaryl aminobutyl, diketopiperazine technology, applied in 3 fields

Inactive Publication Date: 2010-10-06
于清
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] But so far, there is no report about 3,6-bis(4-bis...

Method used

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  • Synthetic methods of 3,6-bis(4-bisfumaroyl aminobutyl)-2,5-diketopiperazine and salt substitute thereof
  • Synthetic methods of 3,6-bis(4-bisfumaroyl aminobutyl)-2,5-diketopiperazine and salt substitute thereof
  • Synthetic methods of 3,6-bis(4-bisfumaroyl aminobutyl)-2,5-diketopiperazine and salt substitute thereof

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Embodiment 1

[0020] Embodiment 1: an instance of method 1;

[0021] Step 1, dehydration ring closure reaction: add 30 grams of ε-benzyloxycarbonyl-L-lysine and 50 grams of m-cresol, and 5 grams of phosphorus pentoxide in a conical flask, heat to 200 ° C, during the reaction The water was distilled off, and then the reactant was cooled in a mixed solution of water and sodium hydroxide (10:1) to form a precipitate. After the precipitate was separated and washed with 30 ml of ethanol, the crude product of the intermediate 3,6-bis[4-(N-tert-butoxycarbonyl)aminobutyl]-2,5-diketopiperazine was obtained after filtration 20.6 grams. The obtained crude product was heated (100° C.) in 100 ml of glacial acetic acid solution, then added with 30 ml of pure water to cool, and then washed with 50 ml of glacial acetic acid solution to obtain the intermediate 3,6-bis[ 11.2 g of the refined product of 4-(N-tert-butoxycarbonyl)aminobutyl]-2,5-diketopiperazine. Step 2, hydrogenation reaction: 11.2 g of the...

Embodiment 2

[0025] Embodiment 2: an example of method 2;

[0026]Step 1, dehydration ring closure reaction: add 30 grams of N-6-trifluoroacetyl-L-lysine, 30 grams of bis(2-methoxyethyl ether) and 5 grams of dioxypentoxide in an Erlenmeyer flask Phosphorus, mixed and stirred and then heated to 180°C. During the reaction, the water was removed by means of distillation, and then the reactant was cooled to room temperature in a mixed solution of water and sodium hydroxide (10:1) to form a precipitate. After the precipitate was separated and washed with 30 ml of ethanol, 18.5 g of crude intermediate 3,6-bis(trifluoroacetyl-1-aminobutyl)-2,5-diketopiperazine was obtained. Heat the obtained crude product to 130°C in 100 ml of glacial acetic acid solution, then add 20 ml of pure water to cool, then wash the crystals with 60 ml of glacial acetic acid solution, and then rinse with 60 ml of pure water to obtain the intermediate 12.8 g of the refined product of 3,6-bis(trifluoroacetyl-1-aminobutyl)-...

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Abstract

The invention relates to two synthetic methods of 3,6-bis(4-bisfumaroyl aminobutyl)-2,5-diketopiperazine and a salt substitute thereof. The first synthetic method comprises the following steps of: obtaining a final product through the steps of cyclodehydration, hydrogenation, coupling, saponification, recrystallization and the like by using epsilon-benzoyloxycarbonyl-L-lysine and p-nitryl monoethyl fumarate as starting materials. The second synthetic method comprises the following steps of: obtaining the final product through the steps of cyclodehydration, coupling, saponification, recrystallization and the like by using N-6-trifluoroacetyl-L-lysine and the p-nitryl monoethyl fumarate (or p-nitryl monoethyl fumarate acyl chloride) as the starting materials. Meanwhile, the salt substitute of the 3,6-bis(4-bisfumaroyl aminobutyl)-2,5-diketopiperazine can also be generated by directly carrying out substitution reaction on the 3,6-bis(4-bisfumaroyl aminobutyl)-2,5-diketopiperazine as a reaction product and corresponding salt.

Description

technical field [0001] The present invention relates to the synthetic method of diketopiperazine organic compound and its salt substitute, especially relate to 3,6-bis(4-bisfumarylaminobutyl)-2,5-diketopiperazine and The synthesis method of its salt substitute. Background technique [0002] Effective drug delivery has been a long-standing technical problem. In practical applications, many active ingredients of multi-drugs are decomposed before being delivered to the designated parts of the patient's body, and the expected drug delivery effect cannot be achieved. An effective way to solve this problem is to select an appropriate chemical that is stable at a certain pH value and temperature, and can quickly dissolve, be absorbed by the human body, and quickly deliver to the designated site at another specific pH value and temperature environment. Substances, which are made into drug carrier particles with suitable properties (such as particle size, shape, structural strength,...

Claims

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Application Information

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IPC IPC(8): C07D241/08
Inventor 于清
Owner 于清
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