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Hydrogel composition comprising a crosslinked polymer

A technology of cross-linked polymer and gel composition, applied in the field of oxidation products of hyaluronic acid, can solve problems such as difficulty in development

Pending Publication Date: 2021-02-05
CROMA PHARMA GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has proven difficult to develop hyaluronic acid-based soft tissue fillers that are both easy to inject through high-gauge needles (i.e., fine needles) and have prolonged duration in vivo

Method used

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  • Hydrogel composition comprising a crosslinked polymer
  • Hydrogel composition comprising a crosslinked polymer
  • Hydrogel composition comprising a crosslinked polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Example 1 - Determination of degree of modification

[0101] Quantification of sulfhydryl groups in thiol-modified hyaluronic acid (HA-SH) used as a raw material for the preparation of hydrogel compositions was based on a wet chemical method using 2,2'-dithiodipyridine (DTDP). The free thiol moiety covalently bonded to the polymer backbone undergoes a thiol-disulfide exchange reaction with DTDP, releasing one equivalent of a chromophoric thione. The absorbance of the resulting thione can be measured photometrically at 343 nm in buffered acidic medium (pH=4).

[0102] About 420 mg of thiol-modified hyaluronic acid was accurately weighed and dissolved in 30 g of 0.01N HCl under continuous magnetic stirring for 2-3 hours to prepare a stock solution. Then, about 310 mg of the stock solution was accurately weighed and mixed with 4200 mg of acetate buffer at pH 4 in an eppendorf tube to prepare a sample solution. Three sample solutions were prepared from each stock soluti...

Embodiment 2

[0103] Example 2 - Determination of residual sulfhydryl content

[0104] To determine the residual sulfhydryl content of the cross-linked polymer in the hydrogel composition (ie the HA-SH polymer after cross-linking and production of the composition), a method similar to that described above was used.

[0105] Approximately 50 mg of each sample hydrogel was accurately weighed and mixed with 1.3 mL of an acetate buffer (pH 4) solution containing 0.125 mg / mL DTDP. 25.0 mg of N-acetylcysteine ​​was accurately weighed and dissolved in 200.0 mL of acetate buffer (pH 4). This solution was then further diluted with acetate buffer (pH 4) to prepare a calibration curve. Acetate buffer was used as blank. 500 μL of acetate buffer (pH 4) solution containing 0.125 mg / mL DTDP was added to each 500 μL sample of the calibration curve and the blank. All samples were incubated for 120 min at room temperature with continuous agitation. After centrifugation of all samples, 500 μL of each su...

Embodiment 3

[0106] Example 3 - Method of Preparing Hydrogel Compositions

[0107] Method A

[0108] Dissolution: Dissolve thiol-modified hyaluronic acid, unmodified hyaluronic acid and lidocaine hydrochloride in an aqueous solution simultaneously.

[0109] Cross-linking: After adjusting the pH to about 6.8 to 7.6, the thiol-modified hyaluronic acid is cross-linked by oxygen oxidation of the sulfhydryl groups to disulfide bridges.

[0110] Sieving: Optionally, the hydrogel comprising cross-linked thiol-modified hyaluronic acid, unmodified hyaluronic acid and lidocaine hydrochloride is pressed through a filter plate with defined mesh size (one or more times).

[0111] Sterilization: Autoclave after filling the hydrogel into the syringe.

[0112] Method B

[0113] Dissolution: Dissolve thiol-modified hyaluronic acid, unmodified hyaluronic acid and lidocaine hydrochloride in acidic aqueous solution simultaneously.

[0114] Cross-linking: After adjusting the pH to about 6.8 to 7.6, the t...

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Abstract

A sterile hydrogel composition comprising a crosslinked polymer, wherein the crosslinked polymer is an oxidation product of a thiol-modified hyaluronan and wherein the thiol- modified hyaluronan has adegree of modification of hyaluronan with thiol moietiesof more than about 80 [mu]mol per gram polymer, wherein the thiol-modified hyaluronan has a degree of modification of hyaluronan with thiol moieties of less than about 280 [mu]mol per gram polymer, and wherein the thiol-modified hyaluronan has a mean molecular weight of at least 400 kDa.

Description

[0001] The present invention relates to sterile hydrogel compositions comprising a cross-linked polymer which is an oxidation product of sulfhydryl-modified hyaluronic acid, its use and a process for its preparation. Background technique [0002] Hyaluronic acid (Hyaluronan, abbreviated as HA, also known as hyaluronic acid) and its salts (such as sodium hyaluronate) are naturally occurring anionic non-sulfated glycosaminoglycans with repeating D-glucuronides A disaccharide of acid and N-acetyl-D-glucosamine. [0003] High molecular weight hyaluronic acid occurs naturally in the skin and is known for its viscoelasticity and very high water absorption. Its properties contribute to the elasticity of the skin to a large extent. Given its properties and its biocompatible, tolerable and non-toxic properties, the advantages of this compound have been exploited for more than 10 years in many applications in the medical and cosmetic fields, especially in cosmetic surgery. For example...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61L27/20A61L27/50A61L27/52A61L27/60A61K8/73A61Q19/08
CPCA61K8/735A61L27/20A61L27/50A61L27/52A61L27/60A61Q19/08A61K8/042C08L5/08A61K47/36A61K9/06A61L2430/34A61L2400/06A61L2300/402A61L2300/236A61K2800/91A61K31/167A61L27/26A61L27/54A61L2300/204A61M5/329A61M5/3295
Inventor 马丁·普林茨拉尔夫·霍劳斯罗伯特·萨赫森霍夫
Owner CROMA PHARMA GMBH
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