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Branched Polyethylene Glycol Epoxy Derivatives Crosslinked Sodium Hyaluronate Gel and Its Preparation and Application

An alcohol-epoxy, branched technology, applied in medical preparations containing active ingredients, medical preparations without active ingredients, tissue regeneration, etc., can solve the problems of difficult removal, hidden dangers of toxicity and cancer, etc.

Active Publication Date: 2020-09-04
JENKEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is worth noting that the above-mentioned cross-linking agents are toxic or potentially carcinogenic, and the spatial network structure after cross-linking has a wrapping effect on the unreacted cross-linking agent, making it difficult to remove

Method used

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  • Branched Polyethylene Glycol Epoxy Derivatives Crosslinked Sodium Hyaluronate Gel and Its Preparation and Application
  • Branched Polyethylene Glycol Epoxy Derivatives Crosslinked Sodium Hyaluronate Gel and Its Preparation and Application
  • Branched Polyethylene Glycol Epoxy Derivatives Crosslinked Sodium Hyaluronate Gel and Its Preparation and Application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0151] Embodiment 1: Synthetic four-arm dodecaethylene glycol tetraglycidyl ether (Ia)

[0152] The four-arm dodecaethylene glycol tetraglycidyl ether of the following structure is synthesized:

[0153]

[0154] Add four-arm dodecaethylene glycol ( 0.1mol), tetrahydrofuran (THF, 100mL) and potassium hydroxide (0.8mol), stirred in a water bath, then dripped epichlorohydrin (ECH, 1.2mol) into the reaction system, controlled the reaction temperature not to exceed 35°C, and reacted at room temperature overnight. After the reaction, the reaction solution was filtered, and the filter residue was washed with dichloromethane, then the filtrate was collected, and the dichloromethane was removed by rotary evaporation to obtain a crude product. The crude product was separated by a silica gel column to obtain pure tetraethylene glycol diglycidyl ether.

[0155] 1 H-NMR (DMSO-d 6 ): 2.26-2.30(m, 8H), 2.54-2.55(m, 4H), 2.72-2.73(m, 4H), 3.09-3.10(m, 4H), 3.17-3.28(m, 20H), 3.35-3.6...

Embodiment 2

[0157] Embodiment 2: Synthetic four-arm tetraglycidyl glycol tetraglycidyl ether (Ib)

[0158] Synthesize four-arm tetraglycidyl glycol tetraglycidyl ether with the following structure:

[0159]

[0160]To the three-neck flask, add four-arm tetracosanthylene glycol ( 0.1mol), tetrahydrofuran (THF, 100mL) and potassium hydroxide (0.8mol), stirred in a water bath, and then dripped epichlorohydrin (ECH, 1.2mol) into the reaction system, controlling the reaction temperature not to exceed 35°C, and reacting at room temperature overnight. After the reaction, the reaction solution was filtered, and the filter residue was washed with dichloromethane, then the filtrate was collected, and the dichloromethane was removed by rotary evaporation to obtain a crude product. The crude product was separated by a silica gel column to obtain pure tetraglycidyl ether.

[0161] 1 H-NMR (DMSO-d 6 ): 2.26-2.30(m, 8H), 2.54-2.55(m, 4H), 2.72-2.73(m, 4H), 3.09-3.10(m, 4H), 3.17-3.28(m, 20H), 3...

Embodiment 3

[0163] Embodiment 3: Synthesis of eight-arm tetraethylene glycol octaglycidyl ether (Ic)

[0164] Synthesize eight-arm tetraethylene glycol octaglycidyl ether of the following structure:

[0165]

[0166] Add octaarm tetraethylene glycol ( 0.1mol), tetrahydrofuran (THF, 100mL) and potassium hydroxide (1.6mol), stirred in a water bath, and then dripped epichlorohydrin (ECH, 2.4mol) into the reaction system, controlling the reaction temperature not to exceed 35°C, and reacting at room temperature overnight. After the reaction, the reaction solution was filtered, and the filter residue was washed with dichloromethane, then the filtrate was collected, and the dichloromethane was removed by rotary evaporation to obtain a crude product. The crude product was separated by silica gel column to obtain pure eight-arm tetraethylene glycol octaglycidyl ether.

[0167] 1 H-NMR (DMSO-d 6 ): 2.27-2.33(m, 16H), 2.54-2.55(m, 8H), 2.72-2.73(m, 8H), 3.09-3.10(m, 8H), 3.16-3.26(m, 24H), ...

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Abstract

The invention discloses a branched polyglycol epoxy derivative cross-linked sodium hyaluronate gel and its preparation and application. The cross-linking agent used in the cross-linked sodium hyaluronate gel prepared by the present invention is a polyglycol epoxy derivative. Due to the presence of multiple ether bonds in its molecule, there are more hydrogen bonds in the gel system, making the gel The stability of the gel is enhanced; at the same time, due to the particularity of the spatial structure of the branched polyglycol epoxy derivatives, the intertwined structure of the gel space is more complicated, and the gel is more stable. In addition, since the branched polyglycol epoxy derivative involved in the present invention is a single molecular weight compound, the gel product produced by it has better batch stability.

Description

technical field [0001] The invention relates to the technical field of sodium hyaluronate gel, in particular to a branched polyglycol epoxy derivative cross-linked sodium hyaluronate gel and its preparation and application. Background technique [0002] Hyaluronic acid (HA) is a linear polymer viscous polysaccharide composed of repeating disaccharide units of glucuronic acid and acetylglucosamine. Hyaluronic acid is an endogenous substance in the human body and has good biocompatibility; it has high viscoelasticity and non-Newtonian rheological properties; it is non-toxic, non-immunogenic, non-irritating, and has a high It is widely used as a soft tissue filler in cosmetology because of its safety and its ability to be degraded and eliminated by injecting hyaluronidase. That is to inject hyaluronic acid into the skin to increase the volume of soft tissue, which can achieve the purpose of wrinkle removal or shaping. However, because hyaluronic acid itself exists in liquid f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/28C08J3/24C08J3/075A61K8/39A61K8/73A61K8/86A61K9/06A61K47/22A61K47/36A61L27/26A61L31/04A61Q19/00C08L5/08C08L71/02
CPCA61K47/22A61K47/36A61L27/26A61L31/041A61Q19/00A61K8/39A61K8/735A61K8/86A61K9/06C08G65/2609C08J3/075C08J3/246C08J2471/02C08J2305/08A61K2800/10A61L2430/34C08L5/08C08L71/02C08B37/0072A61L27/20A61L27/52C08G59/32C08G65/331C07D303/30C08K5/0025C08K5/1515C08G59/3236C08G59/3263C08J3/24A61L27/50A61K31/728
Inventor 魏真林美娜赵宣
Owner JENKEM TECH
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