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Dihydrazide compound and its preparation method and application

一种化合物、肼解反应的技术，应用在化合物领域，能够解决不能满足材料新型化学改性和化学交联等问题

Active Publication Date: 2008-06-04
BIOREGEN BIOMEDICAL (CHANGZHOU) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, such dihydrazides only have the above-mentioned aliphatic disulfide bond-containing dihydrazides and a small amount of aromatic dihydrazides, which cannot meet the needs of new chemical modification and chemical crosslinking of materials.

Method used

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  • Dihydrazide compound and its preparation method and application
  • Dihydrazide compound and its preparation method and application
  • Dihydrazide compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of disuccinic acid diacylcystine dihydrazide (DSCDH for short):

[0040] (1) Synthesis of disuccinic acid dicystine (abbreviated as DSC):

[0041] Cystamine dihydrochloride (Aldrich, USA) 10 g was dissolved in 150 ml distilled water to obtain a clear and transparent solution. Add 4mol / L sodium hydroxide to the above solution until the pH value of the solution is 10. Then, 13.3 g of succinic anhydride (Aldrich, USA) was added under electromagnetic stirring, and at the same time, 4 mol / L sodium hydroxide was continuously added to keep the pH value of the solution at 7-10. After reacting at room temperature for 2 hours, 6 mol / L hydrochloric acid was added to the solution. The white precipitated product was collected by filtration and washed twice with 200 ml of distilled water. Then it was dried under reduced pressure in vacuo to obtain about 15 g of white product DSC as a solid product, and the yield was greater than 90%.

[0042] (2) Synthesis of disuccinic...

Embodiment 2

[0052] Preparation of disuccinic acid diacylcystine dihydrazide (DSCDH for short):

[0053] (1) Synthesis of disuccinic acid dicystine (abbreviated as DSC): same as Example 1.

[0054] (2) Synthesis of activated bisuccinic acid bisacylcystine biscarbonyldiimidazole ester (DSCDI for short):

[0055] Add 10g DSC, 60ml anhydrous DMF in the 500ml three-neck round bottom flask, after stirring and dissolving at room temperature, add 11.2g carbonyldiimidazole (Aldrich, the United States), at this moment, the solution produces a large amount of carbon dioxide bubbles and white precipitate, and the reaction under reduced pressure at room temperature is 3 hours; then add 200ml of anhydrous ethyl acetate to dilute, and collect the precipitated product by filtration. The precipitate was rinsed twice with 200 ml of anhydrous ethyl acetate, and then dried under reduced pressure in vacuo to obtain about 12 g of white solid product DSCDI, with a yield greater than 90%.

[0056] (3) Synthesi...

Embodiment 3

[0059] Preparation of Diglutaric Acid Diacylcystine Dihydrazide (abbreviated as DGCDH):

[0060] (1) Synthesis of double glutaric acid dicystine (abbreviated as DGC):

[0061] Cystamine dihydrochloride (Aldrich, USA) 10 g was dissolved in 150 ml distilled water to obtain a clear and transparent solution. Add 4mol / L sodium hydroxide to the above solution until the pH value of the solution is 10. Then, 15.2 g of glutaric anhydride (Aldrich, USA) was added under electromagnetic stirring, and at the same time, 4 mol / L of sodium hydroxide was continuously added to keep the pH value of the solution at 7-10. After reacting at room temperature for 2 hours, 6 mol / L hydrochloric acid was added to the solution. The white precipitated product was collected by filtration and washed twice with 200 ml of distilled water. Then it was dried under reduced pressure in vacuo to obtain about 15.5 g of white solid product DGC, and the yield was greater than 90%.

[0062] (2) Synthesis of diethy...

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Abstract

The invention discloses a dihydrazide compound of the general formula (I) or the general formula (II), wherein R1-R4 is respectively alkylene, substitute alkylene, aromatic group or polyphenyl. The invention also discloses a preparation method of the dihydrazide compound and application of the dihydrazide compound in preparation of medical hydrogel and a drug slow release carrier.

Description

technical field [0001] The present invention relates to compounds, in particular to a novel dihydrazide compound; in addition, the present invention also relates to a preparation method and application of the dihydrazide compound. Background technique [0002] Dihydrazides refer to compounds with two hydrazide functional groups, which are widely used as chemical modifiers and chemical crosslinking agents, and have important uses in the fields of biomedicine and new materials. Dihydrazides containing disulfide bonds are a new class of hydrazides developed in recent years, which can introduce disulfide bonds and make crosslinked products have special properties while chemically modifying and crosslinking materials. For example, Tesoro et al. used dithiodipropionyl hydrazide in US Pat. No. 4,882,399 to prepare an epoxy resin with reversible crosslinking. Shu et al. in Biomacromolecules, 3, 1304, 2002 reported the preparation of dithiodipropionyl hydrazide and dithiodibutanyl h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/60C07C319/22A61K47/20
CPCC07C323/41C07C323/60A61P3/02
Inventor 舒晓正
Owner BIOREGEN BIOMEDICAL (CHANGZHOU) CO LTD
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