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Diketopiperazine compound and application thereof

A technology of diketopiperazine and compounds, which is applied in the field of diketopiperazine compounds, can solve the problem of single diketopiperazine derivatives, and achieve the effect of effective transmission

Pending Publication Date: 2021-10-22
SHANGHAI WHITTLONG PHARMA INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The technical problem to be solved by the present invention is to provide a novel structural diketopiperazine compound and its application in order to overcome the single defect of diketopiperazine derivatives in the prior art

Method used

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  • Diketopiperazine compound and application thereof
  • Diketopiperazine compound and application thereof
  • Diketopiperazine compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0221]

[0222] 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 process 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 intermediate (2S,5S)-2,5-bis[4-(N-benzyloxycarbonyl)aminobutyl]-3,6-dione was obtained after filtration The crude product of piperazine was 20.6 g. The obtained crude product was heated (100° C.) in 100 ml of glacial acetic acid solution, then 30 ml of pure water was added to cool, and then the crystal was washed with 50 ml of glacial acetic acid solution to obtain the intermediate (2S, 5S)- 11.2 grams of refined product of 2,5-bis[4-(N-benzyloxycarbonyl)aminobutyl]-3,6-diketopiperazine.

[0223] Step 2: Hydrogenation reaction: Disso...

Embodiment 2

[0232] Step 1: Dehydration ring closure reaction: add 36 grams of ε-benzyloxycarbonyl-L-lysine and 59 grams of m-cresol, and 6 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 36 ml of ethanol, the intermediate (2S,5S)-2,5-bis[4-(N-benzyloxycarbonyl)aminobutyl]-3,6-dione was obtained after filtration The crude product of piperazine was 24.8 g. The obtained crude product was heated (100° C.) in 120 ml of glacial acetic acid solution, then 36 ml of pure water was added to cool, and then the crystal was washed with 60 ml of glacial acetic acid solution to obtain the intermediate (2S, 5S)- 13.5 grams of refined product of 2,5-bis[4-(N-benzyloxycarbonyl)aminobutyl]-3,6-diketopiperazine.

[0233] Step 2: Hydrogenation reaction: Dissolve 13.5 g of the pr...

Embodiment 3

[0245] Step 1: Dehydration ring closure reaction: add 25 grams of ε-benzyloxycarbonyl-L-lysine and 42 grams of m-cresol, and 4.2 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. The precipitate was separated and washed with 25 ml of ethanol, then filtered to obtain the intermediate (2S,5S)-2,5-bis[4-(N-benzyloxycarbonyl)aminobutyl]-3,6-dione Crude product of piperazine 17.2 g. The obtained crude product was heated (100° C.) in 83 ml of glacial acetic acid solution, then 25 ml of pure water was added to cool, and then the crystal was washed with 42 ml of glacial acetic acid solution to obtain the intermediate (2S, 5S)- 9.3 grams of refined product of 2,5-bis[4-(N-benzyloxycarbonyl)aminobutyl]-3,6-diketopiperazine.

[0246] Step 2: Hydrogenation reaction: Dissolve 9.3 grams of the product from the pr...

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Abstract

The invention discloses a diketopiperazine compound and an application thereof. The invention provides a diketopiperazine compound shown as a formula I or pharmaceutically acceptable salt thereof. The diketopiperazine compound or pharmaceutically acceptable salt thereof can be used as a self-assembled drug-loading microsphere to realize effective delivery of drugs.

Description

technical field [0001] The invention relates to a diketopiperazine compound and its application. Background technique [0002] Drug delivery system has always been an important direction of preparation research. Traditional methods are affected by the pH environment of the digestive tract and various enzymes, which lead to some biologically active substances, such as calcitonin, insulin, mucopolysaccharides, etc., in the gastrointestinal tract. Destruction or inactivation; at the same time, due to the physical and chemical properties of the drug itself, some sensitive drugs are prone to degradation, and the bioavailability of insoluble drugs is low. The development of efficient delivery systems can enhance drug efficacy and reduce toxic side effects. [0003] Diketopiperazine derivatives are a new type of material, which can be precipitated and self-assembled into microspheres in acidic solution. The microspheres have large surface area, high drug loading capacity, and sim...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/08C07D403/14A61K31/495A61K47/22A61K9/16
CPCC07D241/08C07D403/14
Inventor 刘娜王浩赵晓东
Owner SHANGHAI WHITTLONG PHARMA INST
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