Preparation method of ectoin-hyaluronic acid composite gel and obtained product

A technology of hyaluronic acid and ectoine, applied in the fields of pharmaceutical formulation, pharmaceutical science, organic chemistry, etc., can solve the problems of complex cross-linked gel components, mixed types of cross-linked products, and difficult to control impurity content, etc. Improve immune protection, less impurities, mild conditions

Active Publication Date: 2021-03-12
BLOOMAGE BIOTECHNOLOGY CORP LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this method mixes hyaluronic acid, ectoine and BDDE cross-linking agent to carry out cross-linking, and the two ends of BDDE are the structure of propylene oxide group, and reactivity is big, and the kind of cross-linking product is comparatively mixed, not only have experience BDDE cross-linked cross-linked hyaluronic acid, there are also BDDE cross-linked products with ectoine on both

Method used

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  • Preparation method of ectoin-hyaluronic acid composite gel and obtained product
  • Preparation method of ectoin-hyaluronic acid composite gel and obtained product
  • Preparation method of ectoin-hyaluronic acid composite gel and obtained product

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0041] Example 1

[0042] The preparation of the crosslinking agent EBD is as follows:

[0043] (1) EtOAc EtOAc (EtOAc) EtOAc, 10 ° C, raised to 50 ° C, raised to 50 ° C, tap 9.2 g of epoxy chloropropane, dripping for 4 hours, cooling to room temperature, add 100 ml Toluene, stirred, then 10 ml of sodium hydroxide (AQ, 40%), and continued to react at 45 ° C for 1 hour. After the end, 100 mL of water was added, ethyl acetate extraction, concentrated, and the yellow oily product, that is, 1,4 butanediol monocly withglycerol ether.

[0044] (2) 14.6 g of 1,4 butanediol monoclum ether and 17.1 g of ICD were dissolved in 100 ml of toluene, and 0.34 g of tert-butylfiferic acid chromium was added, stirred at 115 ° C for 6 h, and 50 ml of water was added after the reaction was completed. Ethyl acetate extraction, concentration, column chromatography, product B.

[0045] (3) 14.4 g of product B is dissolved in toluene, add 0.072 g of trifluoride ether, warmed to 60 ° C, add 7.1 g of epoxy ...

Example Embodiment

[0046] Example 2

[0047] The preparation of the crosslinking agent EBD is as follows:

[0048] (1) EtOAc EtOAc EtOAc EtOAc EtOAc EtOAc EtOAc EtOAc EtOAc EtOAc EtOAc. Toluene, stirred, then 10 ml of sodium hydroxide (AQ, 40%), and continued to react at 45 ° C for 1 hour. After the end, 100 mL of water was added, ethyl acetate extraction, concentrated, and the yellow oily product, that is, 1,4 butanediol monocly withglycerol ether.

[0049] (2) 14.6 g of 1,4 butanediol monoclumol ether and 14.2 g of ICD were dissolved in 100 mL of acetone, and 0.071 g of t-butylfiferic acid chromium was added, 60 ° C was stirred for 2 h, and 50 ml of water was added after the reaction was completed. Ethyl acetate extraction, concentration, column chromatography, product B.

[0050] (3) 14.4 g of product B is dissolved in acetone, add 0.028 g of trifluoride ether, warmed to 40 ° C, add 7.1 g of epoxy chloropropane, and continue to react after 2 hours, cool to room temperature, add 100 ml of acetone....

Example Embodiment

[0051] Example 3

[0052] The preparation of the crosslinking agent EBD is as follows:

[0053] (1) 1,4-butanediol and 2.7 g of trifluoride diethyl ether were added to the flask, warmed to 80 ° C, add 10.8 g of epoxypropylene chloropropane, and continued to react after 12 hours, cooled to room temperature. 100 mL toluene, stirred, then 10 ml of sodium hydroxide (AQ, 40%), and continued to react at 45 ° C for 1 hour. After the end, 100 mL of water was added, ethyl acetate extraction, concentrated, and the yellow oily product, that is, 1,4 butanediol monocly withglycerol ether.

[0054] (2) 14.6 g 1, 4 butanediol monoclum ether and 28.4 g of Ikectorin were dissolved in 100 ml of n-hexane, and 1.46 g of tert-butylfiferic acid chromium was added, stirred at 80 ° C for 12 h, and 50 ml of water was added after the reaction was completed. Ethyl acetate extraction, concentration, column chromatography, product B.

[0055] (3) 14.4 g of product B is dissolved in n-hexane, and 1.44 g of tri...

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Abstract

The invention discloses a preparation method of ectoin-hyaluronic acid composite gel and an obtained product. The preparation method comprises the following steps: firstly, preparing a cross-linking agent EBD by a step-by-step method; then, subjecting the EBD and BDDE, used as mixed cross-linking agents, to a cross-linking reaction with hyaluronic acid or salt thereof to prepare cross-linked hyaluronic acid gel, adding free epsilon-polyine to the cross-linked hyaluronic acid gel again, and mixing the components to prepare the ectoin-hyaluronic acid composite gel. The composite gel provided bythe invention contains free and cross-linked ectoin, not only has a filling effect, but also can achieve anti-aging and skin repair and regeneration effects in the whole hyaluronic acid gel filling period through the matching of the two forms of ectoin; in addition, the product, as a viscoelastic agent for adjuvant therapy in glaucoma surgery, lacrimal passage occlusion surgery, vitrectomy and other surgeries, has higher potential and effect.

Description

technical field [0001] The present invention relates to a preparation method of ectoine-hyaluronic acid composite gel, and also relates to the composite gel prepared according to the method and the application of the composite gel in injection products, belonging to biomedical material technology field. Background technique [0002] Ecdoine (2-methyl-1,4,5,6,-tetrahydropyrimidine-4-carboxylic acid) is derived from high halophilic bacteria (Halomonas Elongata), and can be used in extreme conditions of high salt, high temperature, and high ultraviolet radiation Next, ectoine can protect halophilic bacteria from harm. Studies have shown that ectoine can promote cell proliferation and differentiation, and at the same time curb the expression of aging genes, fundamentally change the composition of skin cells, delay skin aging; effectively improve the immune protection ability of skin cells, increase cell repair ability, and effectively resist Invasion of microorganisms and alle...

Claims

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Application Information

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IPC IPC(8): C08L5/08C08K5/3462C08K5/1515C08J3/24C08J3/075C08B37/08C07D405/12A61L27/20A61L27/52A61L27/54A61L27/50A61L31/04A61L31/14
CPCC08J3/075C08J3/24C08K5/3462C08B37/0072C07D405/12A61L27/20A61L27/52A61L27/54A61L27/50A61L31/042A61L31/145A61L31/14C08J2305/08C08K5/1515A61L2300/216A61L2300/412A61L2400/06A61L2430/34C08L5/08
Inventor 李敏李超庞萌萌王静刘建建郭学平
Owner BLOOMAGE BIOTECHNOLOGY CORP LTD
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