WO2003068281A1 - Composition pour la preparation cutanee comprenant un hydrogel de chitosane - Google Patents
Composition pour la preparation cutanee comprenant un hydrogel de chitosane Download PDFInfo
- Publication number
- WO2003068281A1 WO2003068281A1 PCT/EP2003/001424 EP0301424W WO03068281A1 WO 2003068281 A1 WO2003068281 A1 WO 2003068281A1 EP 0301424 W EP0301424 W EP 0301424W WO 03068281 A1 WO03068281 A1 WO 03068281A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydrogel
- chitosan
- dressing
- plate
- acetylation
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/28—Polysaccharides or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
Definitions
- the present invention relates to a composition and also to a dressing intended for the repair and healing of lesions of the chronic skin wounds or acute wounds type. It relates more particularly to a composition or a dressing comprising a real physical hydrogel of chitosan.
- Lesions such as chronic skin wounds and acute wounds are deep lesions that affect both the epidermis and the dermis. These types of lesions include bedsores, venous or arterial ulcers and traumatic wounds as well as burns and acute radiodermatitis.
- We can cite here other dermatological conditions generating skin wounds such as necrotic angiodermitis, oily epidermolysis, and grafts.
- Chitin is the most widespread biopolymer in nature with cellulose. It can be extracted from the skeleton of certain animals, for example the exoskeleton of certain crustaceans, such as lobster, crab or shrimp or the endoskeleton of squid. Chitin and chitosan consist of the same two monomer units, N-acetyl-D-glucosamine and D-glucosamine. Chitin contains a large proportion of N-acetyl-D-glucosamine monomer units, greater than 60%. On the other hand, chitosan contains a proportion of N-acetyl-D-glucosamine monomer units of less than 60%. Chitosan is obtained in particular by total or partial deacetylation of chitin.
- Chitin and chitosan have bio-activity properties, such as activation of the healing process, bio-compatibility and also bio-degradability and bio-resorbability which have led to an important use of these polymers in the medical field.
- bio-activity properties such as activation of the healing process, bio-compatibility and also bio-degradability and bio-resorbability which have led to an important use of these polymers in the medical field.
- a dressing consisting of an acetylated chitin or chitosan gel with an acetylation degree of at least 60%, which corresponds to a chitin gel, according to the definition of chitin mentioned above .
- a physical gel is a three-dimensional network of polymer chains linked together by reversible (non-covalent) junctions. This definition is different from that which wrongly calls gel a very viscous solution.
- driydrogel when it is a mixture containing a polymer and more than 90% water.
- the dressing is in the form of a three-dimensional network consisting of a mixture of water and chitin, the structure of said network being a function of the operating conditions used. According to this document, when the dressing is applied to the lesion, cell development occurs which penetrates the gel, more precisely in the locations left free by the three-dimensional network of chitin.
- the aim set by the applicant is to propose a composition and also a dressing comprising said composition, which allows, not only the protection of the lesion from the external environment but also the cellular reconstruction of the dermis and the epidermis up to to complete healing, in optimal conditions.
- This object is perfectly achieved by the composition for repairing and healing of skin lesions of the chronic or acute wounds type, which, in a manner known in document FR2,736,835, consists of a hydrogel.
- it is a hydrogel of deacetylated chitosan with a degree of acetylation of at most 40%.
- composition and the dressing of the present invention have very slow biodegradability and bio-resorption properties.
- the degree of acetylation of the chitosan hydrogel is of the order or less than 30%.
- the lysozyme or N-acetyl- ⁇ -d-glucosaminidase hydrolytic systems recognize perfectly the natural structure of chitin, with its monomer units mainly of N-acetyl-D-glucosamine.
- these hydrolytic systems do not recognize a biopolymer comprising exclusively D-glucosamine monomer units.
- the more the chitosan will be deacetylated and the less it will be biodegradable and bioresorbable.
- the acetylation rate of chitosan is between 2 and 6%.
- this cell development occurs at the interface between the lesion and the hydrogel and that this cell development takes place under optimal conditions.
- This interface is particularly complex and the latter evolves during the healing process.
- this interface is made up of many elements, in particular blood products such as fibrin or fibrinogen, von Willebrand factor, as well as products released by activated platelets such as fibronectin, growths, PDGF, bFGF, TGF and TGF ⁇ .
- This interface could also play a predominant role during the inflammatory phase by trapping the neutrophils, monocytes and the factors released by these circulating cells such as TNF ⁇ , TGF ⁇ and VEGF.
- this interface still plays an important role during the phase of formation of the granulation tissue comprising angiogenesis since similar growth factors are involved here (EGF, TNF ⁇ , TGF ⁇ and PDGF).
- EGF epithelial growth factor
- the carboxyl and amino groups of the collagen bind respectively to the amino functions of chitosan and to the groups sulfate and carboxylate of chondroitins 4 and 6 sulfate.
- the acid and sulfate groups of chondroitins 4 and 6 sulfate can ionically bind to the amino functions of chitosan.
- the biomaterial of document EP.296.078 which does not correspond to a hydrogel but to a lyophilized product of the sponge type, is entirely biodegradable in particular by collagenase, even if the rate of enzymatic degradation is reduced up to 50% due to the presence of chitosan and glycosaminoglycans in the ion network.
- the composition for repairing and healing skin lesions must be left in constant contact with said lesion. There is therefore, as is customary practice, renewal of the dressing resulting in the loss of all cellular products in the broad sense actively participating in wound healing. Indeed, since cell development occurs at the interface between the lesion and the composition of the invention, the withdrawal of said composition would risk locally destroying the beneficial action provided by the highly deacetylated chitosan hydrogel.
- the dressing formed from the composition of the invention is in the form of a plate having a reduced thickness, from 1 to 10 mm.
- This plate is then transparent or at least translucent, which makes it possible to carry out a visual examination of the development of the wound, at least at the start of the treatment, before certain constituents of the exudates may possibly interfere with this visual examination.
- the cell reconstruction induced by the highly deacetylated chitosan hydrogel gives a perfectly oriented neo-tissue both for collagen fibers and for vascularization.
- This neo-tissue has a remarkable appearance, without hyper-budding.
- the healing does not only occur by the banks of the lesion and that moreover it prevents the formation of a crust. It is assumed by the applicant that this quite remarkable cellular reconstruction is due to the trapping of growth factors by the highly deacetylated chitosan hydrogel.
- the application of the composition of the invention facilitates cell development from the reserves of stem cells which are found at the base of the hair follicles.
- composition of the invention in the form of a plate is intended to produce a surface contact. It is particularly suitable when the lesion appears as a shallow and widely accessible cavity.
- the plate is handled by the practitioner. It is therefore desirable that it has good mechanical strength, to prevent it from deforming or degrading during this manipulation.
- a plate formed exclusively by a chitosan hydrogel having an acetylation degree of at most 40% it is preferable that its molar mass be at least 400,000 g / mol.
- the mechanical strength of the gel depends in particular on this molar mass and, from this threshold, it is considered that the plate of 1 to 10 mm has sufficient strength to be handled.
- the value of the molar mass is measured according to the light scattering technique and not by the viscosity measurement considered today as giving erroneous results.
- the weight average molar mass (Mw) of the polymer is determined from light scattering measurements at 18 different angles, using the Dawn DSP-EOS spectrometer (Wyatt). The average molar mass is then reduced by using a Zimm diagram, thanks to the values calculated from the Rayleigh-Debye equation.
- This method requires knowledge of the increment of refractive index of the polymer (dn / dc) in the solvent used for the previous experiment. This parameter is measured using an interferometer operating at the same wavelength as the light scattering device.
- a dressing is proposed in the form of a chitosan hydrogel plate, as above, of reduced thickness, for example from 1 to 3 mm, this plate being supported by a sheet.
- support preferably based on cellulose, especially paper.
- the mechanical strength of the dressing is mainly provided by the support sheet, which, moreover, prevents deformation of the plate in the event of tensioning of the dressing.
- the fact that the support sheet is based on cellulose avoids any allergenic phenomenon.
- Cellulose is a natural polymer which presents no biological contraindication.
- the support sheet has a dimension greater than that of the plate, possibly in proportions allowing its winding around a member.
- the support sheet may be in the areas external to the plate, provided with fixing means allowing it to be held in place after winding around a member, means which may in particular be adhesive or self-gripping.
- the assembly of the plate and the support sheet is carried out by impregnation of the support sheet with the chitosan solution, during the formation of the gel. It may be a surface impregnation, with partial or total diffusion of the gel on either side of the support.
- the paper Since the paper is naturally hydrophilic, during the aforementioned impregnation, it absorbs water from the chitosan solution, which tends to concentrate - at least locally - the hydrogel in chitosan. This can be avoided by moistening the paper during said impregnation or by choosing as a support sheet a parchment paper or a sheet of a hydrophobic material or made hydrophobic. In the case of parchment paper, its pores are blocked and it retains a certain hydrophilic character, which allows better control of the hydration of the wound.
- the highly deacetylated chitosan hydrogel can be in the form of particles of more or less reduced sizes, for example obtained by grinding a preformed plate.
- these particles are in the form of a paste, packaged in a suitable container, for example a tube or a syringe.
- a chitosan hydrogel plate (as described above) is ground in water, then the water is partially removed by centrifugation until said paste is obtained.
- the dough can be introduced into a cavity and remain there until it heals. In this case, if the cavity is open towards the outside, there is no bio-resorption of the hydrogel and it is pushed back gradually towards the outside, as the reconstruction of the neo- tissue.
- the description which follows relates to a preferred example of preparation of a real physical gel of chitosan, having a degree of acetylation of between 2 and 6%, in the form of a plate usable as a dressing for the repair and the healing of lesions skin type chronic or acute wounds, whether these lesions are in humans or animals.
- This is obtained by deacetylation steps controlled from purified chitin of squid endo-skeletons. Each deacetylation step takes place in a caustic bath with a high concentration of sodium hydroxide.
- a low viscosity solution is prepared (0.5% by weight of chitosan in an acid solution).
- Three stages of filtration using membranes with decreasing porosities (1.2; 0.8 and 0.45 ⁇ m) under a maximum pressure of 3 bars are applied to the polymer.
- the polymer solution thus filtered is then precipitated by adding a concentrated ammonia solution. This precipitate is then washed several times to remove the excess ammonia.
- the product thus obtained is lyophilized, thus making it possible to obtain the chitosan in solid form.
- 1.2 propanediol is added dropwise. The whole is quickly degassed under vacuum for a period of approximately one hour.
- the formation of the real physical chitosan gel according to the present invention corresponds to the transition from a state of solution (previous situation) to a state of physical gel or hydrogel for which physical cross-links between chains have formed from hydrophobic interactions and hydrogen bonds.
- the solution sets as a gel and therefore a chitosan gel is obtained having an acetylation degree of between 2 and 6% and a concentration of chitosan between 0.2 and 5%.
- the hydrogel thus formed is neutralized by transfer to a basic medium. This step prevents the hydrogel from dissolving in water at physiological pH or when the hydrogel is in contact with physiological solutions or media. Finally, the hydrogel is subjected to successive rinses in order to remove the di-alcohol and obtain a pH close to 7.
- a dressing 1 comprising a plate 2 formed of a chitosan gel having an acetylation degree of at most 40% and a support paper 3 based on cellulose, supporting said plate 2.
- Plate 2 has reduced dimensions (for example of 3 cm x 3 cm) compared to those of paper 3 (for example 20 cm x 5 cm) and is placed in the middle towards an end zone 4 of said paper 3.
- On the face 5 supporting the plate 2, towards the other end zone 6 is provided an adhesive coating 7, sensitive to pressure, protected by a 8 non-stick protective strip.
- the practitioner positions the dressing 1 with the plate 2 covering the lesion on the arm, surrounds the arm with the support paper 3 until the two end zones 4,6 are covered after removing the protective strip 8.
- the dressing 1 is then held in place around the arm, the adhesive coating 7 adhering to the other face 9 of the support paper 3.
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2003206889A AU2003206889A1 (en) | 2002-02-15 | 2003-02-13 | Composition for skin healing comprising a chitosan hydrogel |
CA002476131A CA2476131A1 (fr) | 2002-02-15 | 2003-02-13 | Composition pour la preparation cutanee comprenant un hydrogel de chitosane |
EP03704607A EP1474182A1 (fr) | 2002-02-15 | 2003-02-13 | Composition pour la reparation cutanee comprenant un hydrogel de chitosane |
JP2003567461A JP2005517043A (ja) | 2002-02-15 | 2003-02-13 | キトサンヒドロゲルを含有する皮膚修復用組成物 |
US10/915,621 US20050042265A1 (en) | 2002-02-15 | 2004-08-10 | Composition for cutaneous repair and cicatrization comprising exclusively a true physical hydrogel of chitosan |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR02/01955 | 2002-02-15 | ||
FR0201955A FR2836044A1 (fr) | 2002-02-15 | 2002-02-15 | Composition pour la reparation et la cicatrisation cutanee comprenant exclusivement un vrai hydrogel physique de chitosane |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/915,621 Continuation US20050042265A1 (en) | 2002-02-15 | 2004-08-10 | Composition for cutaneous repair and cicatrization comprising exclusively a true physical hydrogel of chitosan |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003068281A1 true WO2003068281A1 (fr) | 2003-08-21 |
Family
ID=27636228
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2003/001424 WO2003068281A1 (fr) | 2002-02-15 | 2003-02-13 | Composition pour la preparation cutanee comprenant un hydrogel de chitosane |
Country Status (7)
Country | Link |
---|---|
US (1) | US20050042265A1 (fr) |
EP (1) | EP1474182A1 (fr) |
JP (1) | JP2005517043A (fr) |
AU (1) | AU2003206889A1 (fr) |
CA (1) | CA2476131A1 (fr) |
FR (1) | FR2836044A1 (fr) |
WO (1) | WO2003068281A1 (fr) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005097871A1 (fr) * | 2004-03-22 | 2005-10-20 | Universite De Geneve | Composition de chitosane neutralisee pseudo-thermodurcissable formant un hydrogel et procede de production de celle-ci |
JP2006347999A (ja) * | 2005-06-20 | 2006-12-28 | Hoshi Seiyaku Kk | 創傷被覆材およびその製造方法 |
WO2009007635A1 (fr) * | 2007-07-12 | 2009-01-15 | Biopharmex Holding S.A. | Hydrogel de carboxyalkylamide de chitosan, sa preparation et son utilisation cosmetique et dermatologique |
US10328096B2 (en) * | 2016-07-07 | 2019-06-25 | Universita' Degli Studi Di Torino | Composition comprising chitosan for use in the prevention and/or in the treatment of incontinence and/or impotence in a subject undergoing prostatectomy |
US11058712B2 (en) | 2017-07-19 | 2021-07-13 | Universidade Da Beira Interior | Film for topical application in the treatment of skin lesions and method of obtaining and applying same |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CL2008000156A1 (es) * | 2008-01-18 | 2008-08-01 | Igloo Zone Chile S A | Gel estable hidrofilo en base a un polimero para aplicacion topica porque comprende quitosano disuelto en un solvente; proceso para obtener el gel para uso topico antes mencionado; uso del gel. |
US9855372B2 (en) * | 2008-10-17 | 2018-01-02 | Sofradim Production | Auto-sealant matrix for tissue repair |
WO2011004399A2 (fr) * | 2009-07-09 | 2011-01-13 | Manoj Vinoy Mojamdar | Peau en chitosane filmogène liquide pour la guérison des plaies et procédé d'élaboration |
EP2473201B1 (fr) * | 2009-09-01 | 2016-08-10 | Medovent GmbH | Pansement tissulaire à base de chitosane |
US11311644B2 (en) | 2010-09-01 | 2022-04-26 | Medoderm Gmbh | Antimicrobial and/or epithelial cell growth stimulating substance and composition and tissue dressing material |
CN102764447B (zh) * | 2012-07-27 | 2014-02-05 | 武汉人福医疗用品有限公司 | 水凝胶敷料及其制备工艺 |
US9192692B2 (en) | 2013-10-24 | 2015-11-24 | Medtronic Xomed, Inc. | Chitosan stenting paste |
US9192574B2 (en) | 2013-10-24 | 2015-11-24 | Medtronic Xomed, Inc. | Chitosan paste wound dressing |
FR3016882A1 (fr) | 2014-01-30 | 2015-07-31 | Sofradim Production | Procede de preparation de chitosane a haut degre d’acetylation |
JP6776245B2 (ja) * | 2015-01-09 | 2020-10-28 | トリコル バイオメディカル, インコーポレイテッド | 経皮的脈管傷害治療システムおよび方法 |
WO2020040704A1 (fr) * | 2018-08-22 | 2020-02-27 | Novamedic Company Limited | Pansement |
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US4356236A (en) * | 1979-06-15 | 1982-10-26 | Kureha Kagaku Kogyo Kabushiki Kaisha | Spherically shaped material comprising acylated product of de-N-acetylated chitin |
EP0296078A1 (fr) * | 1987-06-15 | 1988-12-21 | Centre National De La Recherche Scientifique (Cnrs) | Nouveaux biomatériaux à base de mélanges de collagène, de chitosan et de glycosaminoglycanes, leur procédé de préparation ainsi que leurs applications en médecine humaine |
FR2736552A1 (fr) * | 1995-07-12 | 1997-01-17 | Textile Hi Tec Sa Soc | Procede pour prolonger la duree de bioresorption d'un materiau implantable dans l'organisme a base de chitine ou de chitosane et materiau obtenu |
FR2736835A1 (fr) * | 1995-07-17 | 1997-01-24 | Aber Technologies | Pansement pour plaies chroniques, notamment escarres, en gel de chitine |
Family Cites Families (1)
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GB1604323A (en) * | 1977-05-20 | 1981-12-09 | Nippon Kogaku Kk | Display circuit |
-
2002
- 2002-02-15 FR FR0201955A patent/FR2836044A1/fr not_active Withdrawn
-
2003
- 2003-02-13 EP EP03704607A patent/EP1474182A1/fr not_active Withdrawn
- 2003-02-13 WO PCT/EP2003/001424 patent/WO2003068281A1/fr active Application Filing
- 2003-02-13 JP JP2003567461A patent/JP2005517043A/ja active Pending
- 2003-02-13 CA CA002476131A patent/CA2476131A1/fr not_active Abandoned
- 2003-02-13 AU AU2003206889A patent/AU2003206889A1/en not_active Abandoned
-
2004
- 2004-08-10 US US10/915,621 patent/US20050042265A1/en not_active Abandoned
Patent Citations (5)
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US4356236A (en) * | 1979-06-15 | 1982-10-26 | Kureha Kagaku Kogyo Kabushiki Kaisha | Spherically shaped material comprising acylated product of de-N-acetylated chitin |
EP0296078A1 (fr) * | 1987-06-15 | 1988-12-21 | Centre National De La Recherche Scientifique (Cnrs) | Nouveaux biomatériaux à base de mélanges de collagène, de chitosan et de glycosaminoglycanes, leur procédé de préparation ainsi que leurs applications en médecine humaine |
US5166187A (en) * | 1987-06-15 | 1992-11-24 | Centre National De La Recherche | Biomaterials with a base of mixtures of collagen, chitosan and glycosaminoglycans, process for preparing them and their application in human medicine |
FR2736552A1 (fr) * | 1995-07-12 | 1997-01-17 | Textile Hi Tec Sa Soc | Procede pour prolonger la duree de bioresorption d'un materiau implantable dans l'organisme a base de chitine ou de chitosane et materiau obtenu |
FR2736835A1 (fr) * | 1995-07-17 | 1997-01-24 | Aber Technologies | Pansement pour plaies chroniques, notamment escarres, en gel de chitine |
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Title |
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CHATELET C ET AL: "Influence of the degree of acetylation on some biological properties of chitosan films", BIOMATERIALS, ELSEVIER SCIENCE PUBLISHERS BV., BARKING, GB, vol. 22, no. 3, February 2001 (2001-02-01), pages 261 - 268, XP004221084, ISSN: 0142-9612 * |
TARAVEL M N ET AL: "Collagen and its interactions with chitosan - III. Some biological and mechanical properties", BIOMATERIALS, ELSEVIER SCIENCE PUBLISHERS BV., BARKING, GB, vol. 17, no. 4, 1996, pages 451 - 455, XP004032786, ISSN: 0142-9612 * |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007529559A (ja) * | 2004-03-22 | 2007-10-25 | ユニベルシテ ドゥ ジュネーブ | ヒドロゲルを形成する、偽熱硬化性の中和されたキトサン組成物、および、この組成物を製造するためのプロセス |
WO2005097871A1 (fr) * | 2004-03-22 | 2005-10-20 | Universite De Geneve | Composition de chitosane neutralisee pseudo-thermodurcissable formant un hydrogel et procede de production de celle-ci |
US8835514B2 (en) | 2004-03-22 | 2014-09-16 | Laboratoire Medidom S.A. | Pseudo-thermosetting neutralized chitosan composition forming a hydrogel and a process for producing the same |
US8507563B2 (en) | 2004-03-22 | 2013-08-13 | Laboratoire Medidom S.A. | Pseudo-thermosetting neutralized chitosan composition forming a hydrogel and a process for producing the same |
US8303980B2 (en) | 2005-06-20 | 2012-11-06 | Hoshi Pharmaceutical Co., Ltd. | Wound-dressing material and method for manufacturing the same |
JP2006347999A (ja) * | 2005-06-20 | 2006-12-28 | Hoshi Seiyaku Kk | 創傷被覆材およびその製造方法 |
JP4703283B2 (ja) * | 2005-06-20 | 2011-06-15 | 星製薬株式会社 | 創傷被覆材およびその製造方法 |
WO2009007635A1 (fr) * | 2007-07-12 | 2009-01-15 | Biopharmex Holding S.A. | Hydrogel de carboxyalkylamide de chitosan, sa preparation et son utilisation cosmetique et dermatologique |
RU2476201C2 (ru) * | 2007-07-12 | 2013-02-27 | Байофармекс Холдинг Лимитед | Гидрогель карбоксиалкиламида хитозана, его приготовление и применение в косметологии и дерматологии |
US8236781B2 (en) | 2007-07-12 | 2012-08-07 | Elisabeth Laugier | Hydrogel of chitosan carboxyalkylamide, preparation thereof and cosmetic and dermatological use thereof |
FR2918565A1 (fr) * | 2007-07-12 | 2009-01-16 | Biopharmex Holding Sa | Hydrogel de carboxyalkylamide de chitosan, sa preparation et son utilisation cosmetique et dermatologique |
US10328096B2 (en) * | 2016-07-07 | 2019-06-25 | Universita' Degli Studi Di Torino | Composition comprising chitosan for use in the prevention and/or in the treatment of incontinence and/or impotence in a subject undergoing prostatectomy |
US11058712B2 (en) | 2017-07-19 | 2021-07-13 | Universidade Da Beira Interior | Film for topical application in the treatment of skin lesions and method of obtaining and applying same |
Also Published As
Publication number | Publication date |
---|---|
AU2003206889A1 (en) | 2003-09-04 |
EP1474182A1 (fr) | 2004-11-10 |
US20050042265A1 (en) | 2005-02-24 |
CA2476131A1 (fr) | 2003-08-21 |
FR2836044A1 (fr) | 2003-08-22 |
JP2005517043A (ja) | 2005-06-09 |
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