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Anionically charged chitosan

A technology of chitosan and polysaccharide, applied in the field of carboxyalkyl chitosan, can solve problems such as difficult implementation on an industrial scale, difficulty in implementation, and expensive energy

Active Publication Date: 2020-07-17
KIOMED PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is difficult to implement, and especially difficult to implement on an industrial scale
On the other hand, this substitution method based on crustacean-derived chitin is energetically expensive, with low reproducibility, and the polymer is prone to degradation and the acetyl group of the N-acetyl-glucosamine unit is prone to occur to a large extent hydrolysis, but also difficult to control

Method used

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preparation example Construction

[0129] The invention also relates to a preparation method for preparing carboxyalkyl chitosan.

[0130] According to a variant, the production process for the preparation of carboxyalkyl chitosan according to the invention comprises the preparation of chitosan of fungal origin, reacetylation of the chitosan and carboxyalkylation of the reacetylated chitosan. Accordingly, the present invention relates to a reacetylated chitosan or reacetylated carboxyalkyl chitosan.

[0131] Thus, according to one embodiment, chitosan may be dissolved in an aqueous medium, preferably in a slightly acidic (eg pH 6) aqueous medium. Acetic anhydride can be added to the chitosan solution one or more times. An alkaline agent such as sodium hydroxide and / or urea is then added. An alkylating agent, such as sodium monochloroacetate (ie sodium chloroacetate) or chloroacetic acid, is then added. Subsequently, the substituted chitosan is purified, recovered and dried.

[0132] According to a variant, ...

Embodiment 1

[0237] Example 1 N-succinyl-chitosan

[0238] N with different molecular weights and molecular structures (degree of acetylation (DA) and degree of succinyl substitution (DS)) were prepared and characterized according to the general method described in patent application WO 2016 / 016463 or WO 2016 / 016464 (patent EP 3016663). - Succinochitosan. Except for polymer CSS-1 (Table 1a), the first acetylation step was performed by adding acetic anhydride to increase the degree of acetylation.

[0239] Formulations were prepared with these N-succinyl chitosan (CSS) at a concentration of 2% at physiological pH and osmolarity and packaged in glass syringes. Syringes were sterilized by autoclaving with a standard cycle (15 minutes at 121°C). According to the EP2.9.20 method, the formulations are checked visually to confirm that they are free of any insoluble matter or turbidity over a broad pH range around physiological pH (pH 6.5 to 7.5). Check that the level of bacterial endotoxin in ...

Embodiment 2

[0247] Example 2 - carboxymethyl chitosan of animal origin

[0248] Two carboxymethyl chitosans of animal origin (CC-1 and CC-2 in Table 2a) are available for implantable or injectable pharmaceutical or medical use.

[0249] Two other carboxymethyl chitosans were tested:

[0250] A CC (CC-3) obtained by carboxymethylation of chitin of animal origin,

[0251] A CC (CC-4) obtained by carboxymethylation of chitosan of animal origin prepared by deacetylation of chitin of animal origin.

[0252] Carboxymethyl chitosan (CC) was characterized by carbon 13 NMR to determine it and the values ​​of DA (degree of acetylation) and DS (degree of substitution of carboxymethyl groups) were measured with an error range estimated to be about ±10 % (Table 2a). The electrostatic charge of the polymer was characterized by measuring the zeta potential at a concentration of 0.05% (m / m) in the range from pH 8 to pH 4, and the zeta potential value was recorded at a pH of 7.5 (Table 2a). It was obs...

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Abstract

The present invention relates to a carboxyalkyl chitosan having a maximum zeta potential, measured at pH 7.5, of -10 mV, compositions comprising same, a manufacturing process therefor and various applications thereof, in particular in the field of therapy, rheumatology, ophthalmology, esthetic medicine, plastic surgery, internal surgery, dermatology or cosmetics.

Description

technical field [0001] The present invention relates to carboxyalkyl chitosan, compositions comprising the carboxyalkyl chitosan, a process for its preparation and various uses thereof, especially in the fields of therapy, rheumatology, ophthalmology, cosmetic medicine, plastic surgery, internal surgery , use in the field of dermatology or cosmetics. Background technique [0002] Chitosan derivatives are known, inter alia, in patent applications published by Kiomed Pharma under publication numbers WO 2016 / 016463 and WO 2016 / 016464 and corresponding patents. These patent applications focus on the physical, chemical or physicochemical properties of chitosan derivatives. However, there is still a need to improve these compositions, especially in the case of therapeutic treatments, in order to provide optimal therapeutic benefit to patients who may have to use these compositions, and especially to increase the benefit / risk ratio. [0003] Soluble chitosan can be obtained by re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A61K31/722C08L5/08
CPCC08B37/003A61K31/722A61K9/0019A61K47/36A61P19/02A61P19/04A61L27/20A61K8/736A61Q19/00A61L2400/06A61L2430/24A61L2430/06A61K2800/91A61K9/08C08L5/08C08J3/122A61K31/728
Inventor 迈克尔·肖松皮埃尔·杜埃特桑德琳·埃米莉亚·戈蒂埃菲利普·瓦森欧塔·初曼吉列尔莫·罗卡萨巴斯
Owner KIOMED PHARMA
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