CA2237758A1 - Topical compositions containing a beta-cyclodextrin and an amino polysaccharide - Google Patents
Topical compositions containing a beta-cyclodextrin and an amino polysaccharide Download PDFInfo
- Publication number
- CA2237758A1 CA2237758A1 CA002237758A CA2237758A CA2237758A1 CA 2237758 A1 CA2237758 A1 CA 2237758A1 CA 002237758 A CA002237758 A CA 002237758A CA 2237758 A CA2237758 A CA 2237758A CA 2237758 A1 CA2237758 A1 CA 2237758A1
- Authority
- CA
- Canada
- Prior art keywords
- cyclodextrin
- composition
- beta
- polysaccharide
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/724—Cyclodextrins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Inorganic Chemistry (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A composition is disclosed for topical application for the relief of inflammation and pain. The composition is in the form of an inert powder, or a gel, cream or dispersion containing a clathrating agent which comprises a .beta.-cyclodextrin and an amino polysaccharide.
Description
CA 022377~8 1998-0~-14 TOPICAL COMPOSITIONS CONTAINING A BETA-CYCLODEXTRIN AND AN AMINO POLYSACCHARIDE
t ~ This invention relates to a treatment material applicable to wounds, injuries and a wide variety of diseases of the skin to reduce pain, inflammation and to increase the rate of healing of the affected area of the skin.
The chemistry of the inflammation processes of the skin has revealed the role of the enzyme phospholipase in the hydrolysis of lecithin and the release of free arachidonic acid.
Arachidonic acid is rapidly transformed to the leukotriene via lipoxygenase, thereby producing pain and inflammation.
According to the present invention this train of events can be halted by the topical application of clathrating agents in particular a composition for topical application for the relief of inflammation comprising an inert powder, or a gel, cream or dispersion or the like inert carrier, together with a ~-cyclodextrin and an amino saccharide or polysaccharide.
Combinations of amino saccharides or polysaccharides and cyclodextrins according to the invention have been shown to be beneficial in the treatment of skin disorders such as eczema and psoriasis, and have unexpectedly been found to be more effective than either component alone. By incorporating the amino polysaccharide and cyclodextrin with a cross linked acrylic polymer, in accordance with a preferred embodiment, a dry sterile dressing for the treatment wounds or injuries may be produced to which sterile water may be added immediately 1 prior to application.
B-cyclodextrin is a cyclic polymer containing seven D-glucose units and has a doughnut-shaped molecular structure including an interior cavity which receive other molecules and form clathrate compounds therewith. While the efficacy of the , CA 022377~8 1998-0~-14 invention does not depend on the correctness of the theory, it is believed that the cyclodextrin clathrates the arachidonic acid produced by the wound and thus effectively removes it and so prevents or reduces the pain and inflammation associated with it.
Preferably, the amino saccharides and polysaccharides employed include chitin and products derived from chitin, for example by hydrolysis, to produce n-acetyl glucosamine which can then be de-acylated to give glucosamine or glucosamine hydrochloride.
Such compounds have analgesic or or anti-inflammatory properties and the efficacy thereof has been unexpectedly found to be enhanced when used with cyclodextrin an accordance with the invention.
Further combinations of these ingredients have been employed to demonstrate the broad range of applications in creams, gels and dispersions in the treatment or prevention of a wide range of diseases or injuries.
The following examples will serve or illustrate the novelty and benefits of this invention.
ExamPle 50.0g of glucosamine hydrochloride 50.0g of dimethyl ~. cyclodextrin made up to l litre with sterile water.
The solution was then added to a mixture of l kg. coconut oil and 40g of an organo phosphate ester emulsifier maintained at 50~C. After agitation and cooling this produced a lotion t suitable for topical application to the skin to combat inflammation.
_ CA 022377~8 l998-0~-l4 ExamPle II
4.0g of Alcosorb polymers lO.Og glucosamine hydrochloride and 15.0g ~. cyclodextrin iodine clathrate The mixture was mixed thoroughly and placed within a sachet made from bonded synthetic polymers measuring 10 x 15 cms.
The sealed sachet was maintained in a dry, sterile condition prior to use.
Exam~le III
40g Alcosorb polymers lOOg glucosamine hydrochloride 150g dimethyl ~. cyclodextrin The mixture was mixed thoroughly prior to the addition of 1800ml of sterile water, added with constant agitation for a period of five (5) minutes.
The resultant gel was then preserved in sterile containers.
Example IV
lOOg chitin Poly-(1-4) ~-D-N-acetylglucosamine 50g ~. cyclodextrin 50g Alcosorb The ingredients were admixed and ground to a particle size of 50 microns. The resultant powder was suitable for inclusion with synthetic polymers of incorporation with fabricated polymers.
J
The preparations illustrated but not limited by Examples I to V were then subjected to a series of tests as demonstrated by the following examples.
CA 022377~8 1998-0~-14 Exam~le VI
The lotion prepared as in Example I was applied to the affected tissue on patients suffering from psoriasis or eczema. All reported relief from pruritis within lO minutes after application and regeneration of dermal tissue was observed on the fourth day.
~xamPle VI
A sachet, produced as in Example II, was immersed in 0.5 litres of sterile water for five (S~ minutes and applied to a second degree burn on a patients forearm. The dressing was bandaged in place for twenty four hours. Relief from pain occurred within minutes and when the dressing was removed the healing process had commenced.
ExamPle VII
Gel, produced as in Example II, was applied to insect bites, minor scalds and burns in a variety of patients.
The response obtained in all cases was the rapid relief from pain and promotion of healing.
Example VIII
The powder produced as in Example IV was incorporated in the layer of fabric used to produce sanitary wear. In the case of infants the incidence of infection caused by the micro organism Candida albicans, known as nappy rash, was significantly reduced. Other applications for the reduction of infection by this organism are related to age and sex.
In each of the Examples I to IV the dimethyl ~. cyclodextrin and ~. cyclodextrin may be exchanged without detracting from the principle of the invention.
CA 022377~8 l998-0~-l4 Similarly the amino polysaccharides as a group display similar characteristics from a therapeutic standpoint although the chemical and or physical properties may differ.
-ExamPle IX
A colloidal suspension was prepared from a combination ofchitin, chitosan and glucosamine having a particle size of less than 5 microns in an aqueous solution of ~-cyclodextrin in the following manner:
40g chitin (poly(1-4)~-N-acetyl-D-glucosamine) 40g chitosan (poly(1-4)-3-glucosamine) 20g glucosamine The above ingredients were introduced with agitation into an aqueous solution containing ~-cyclodextrin and the whole made up to a total volume of l litre.
A non-woven polyester fabric was wetted with this suspension by short term immersion ~1-2 seconds, nip rollers) then dried prior to forming into lOcm squares for use in surgical dressings as the contact surface with the perturbed tissue.
When applied to lacerated tissue, relief from pain occured within minutes and the healing process was accelerated.
Analysis of the treated fabric showed that the level of the combined ingredients was 1.7% w/w. It is believed that a combination of saccharides and polysaccharides as in this Example is particularly effective.
t ~ This invention relates to a treatment material applicable to wounds, injuries and a wide variety of diseases of the skin to reduce pain, inflammation and to increase the rate of healing of the affected area of the skin.
The chemistry of the inflammation processes of the skin has revealed the role of the enzyme phospholipase in the hydrolysis of lecithin and the release of free arachidonic acid.
Arachidonic acid is rapidly transformed to the leukotriene via lipoxygenase, thereby producing pain and inflammation.
According to the present invention this train of events can be halted by the topical application of clathrating agents in particular a composition for topical application for the relief of inflammation comprising an inert powder, or a gel, cream or dispersion or the like inert carrier, together with a ~-cyclodextrin and an amino saccharide or polysaccharide.
Combinations of amino saccharides or polysaccharides and cyclodextrins according to the invention have been shown to be beneficial in the treatment of skin disorders such as eczema and psoriasis, and have unexpectedly been found to be more effective than either component alone. By incorporating the amino polysaccharide and cyclodextrin with a cross linked acrylic polymer, in accordance with a preferred embodiment, a dry sterile dressing for the treatment wounds or injuries may be produced to which sterile water may be added immediately 1 prior to application.
B-cyclodextrin is a cyclic polymer containing seven D-glucose units and has a doughnut-shaped molecular structure including an interior cavity which receive other molecules and form clathrate compounds therewith. While the efficacy of the , CA 022377~8 1998-0~-14 invention does not depend on the correctness of the theory, it is believed that the cyclodextrin clathrates the arachidonic acid produced by the wound and thus effectively removes it and so prevents or reduces the pain and inflammation associated with it.
Preferably, the amino saccharides and polysaccharides employed include chitin and products derived from chitin, for example by hydrolysis, to produce n-acetyl glucosamine which can then be de-acylated to give glucosamine or glucosamine hydrochloride.
Such compounds have analgesic or or anti-inflammatory properties and the efficacy thereof has been unexpectedly found to be enhanced when used with cyclodextrin an accordance with the invention.
Further combinations of these ingredients have been employed to demonstrate the broad range of applications in creams, gels and dispersions in the treatment or prevention of a wide range of diseases or injuries.
The following examples will serve or illustrate the novelty and benefits of this invention.
ExamPle 50.0g of glucosamine hydrochloride 50.0g of dimethyl ~. cyclodextrin made up to l litre with sterile water.
The solution was then added to a mixture of l kg. coconut oil and 40g of an organo phosphate ester emulsifier maintained at 50~C. After agitation and cooling this produced a lotion t suitable for topical application to the skin to combat inflammation.
_ CA 022377~8 l998-0~-l4 ExamPle II
4.0g of Alcosorb polymers lO.Og glucosamine hydrochloride and 15.0g ~. cyclodextrin iodine clathrate The mixture was mixed thoroughly and placed within a sachet made from bonded synthetic polymers measuring 10 x 15 cms.
The sealed sachet was maintained in a dry, sterile condition prior to use.
Exam~le III
40g Alcosorb polymers lOOg glucosamine hydrochloride 150g dimethyl ~. cyclodextrin The mixture was mixed thoroughly prior to the addition of 1800ml of sterile water, added with constant agitation for a period of five (5) minutes.
The resultant gel was then preserved in sterile containers.
Example IV
lOOg chitin Poly-(1-4) ~-D-N-acetylglucosamine 50g ~. cyclodextrin 50g Alcosorb The ingredients were admixed and ground to a particle size of 50 microns. The resultant powder was suitable for inclusion with synthetic polymers of incorporation with fabricated polymers.
J
The preparations illustrated but not limited by Examples I to V were then subjected to a series of tests as demonstrated by the following examples.
CA 022377~8 1998-0~-14 Exam~le VI
The lotion prepared as in Example I was applied to the affected tissue on patients suffering from psoriasis or eczema. All reported relief from pruritis within lO minutes after application and regeneration of dermal tissue was observed on the fourth day.
~xamPle VI
A sachet, produced as in Example II, was immersed in 0.5 litres of sterile water for five (S~ minutes and applied to a second degree burn on a patients forearm. The dressing was bandaged in place for twenty four hours. Relief from pain occurred within minutes and when the dressing was removed the healing process had commenced.
ExamPle VII
Gel, produced as in Example II, was applied to insect bites, minor scalds and burns in a variety of patients.
The response obtained in all cases was the rapid relief from pain and promotion of healing.
Example VIII
The powder produced as in Example IV was incorporated in the layer of fabric used to produce sanitary wear. In the case of infants the incidence of infection caused by the micro organism Candida albicans, known as nappy rash, was significantly reduced. Other applications for the reduction of infection by this organism are related to age and sex.
In each of the Examples I to IV the dimethyl ~. cyclodextrin and ~. cyclodextrin may be exchanged without detracting from the principle of the invention.
CA 022377~8 l998-0~-l4 Similarly the amino polysaccharides as a group display similar characteristics from a therapeutic standpoint although the chemical and or physical properties may differ.
-ExamPle IX
A colloidal suspension was prepared from a combination ofchitin, chitosan and glucosamine having a particle size of less than 5 microns in an aqueous solution of ~-cyclodextrin in the following manner:
40g chitin (poly(1-4)~-N-acetyl-D-glucosamine) 40g chitosan (poly(1-4)-3-glucosamine) 20g glucosamine The above ingredients were introduced with agitation into an aqueous solution containing ~-cyclodextrin and the whole made up to a total volume of l litre.
A non-woven polyester fabric was wetted with this suspension by short term immersion ~1-2 seconds, nip rollers) then dried prior to forming into lOcm squares for use in surgical dressings as the contact surface with the perturbed tissue.
When applied to lacerated tissue, relief from pain occured within minutes and the healing process was accelerated.
Analysis of the treated fabric showed that the level of the combined ingredients was 1.7% w/w. It is believed that a combination of saccharides and polysaccharides as in this Example is particularly effective.
Claims (8)
1. A composition for topical application for the relief of inflammation comprising an inert powder, or a gel, cream or dispersion or the like inert carrier, together with a cyclodextrin and an amino saccharide or polysaccharide.
2. A composition as claimed in claim 1 in which the amino polysaccharide and cyclodextrin are incorporated with a cross-linked acrylic polymer to form a dry sterile dressing for the treatment of wounds or injuries.
3. A composition as claimed in either of claims 1 or 2 in which the cyclodextrin is .beta.-cyclodextrin or dimethyl .beta.-cyclodextrin.
4. A composition as claimed in any of claims 1 to 3 wherein both a saccharide and a polysaccharide is present.
5. A composition as claimed in any of claims 1 to 4 made into a cream with water and coconut oil by virtue of an organo-phosphate ester emulsifier.
6. A composition as claimed in any of claims 1 to 4 made into a gel with water and alcosorb polymers.
7. A composition as claimed in any of claims 1 to 4 in powder form mixed with alcosorb polymers for mixing with water prior to use.
8. A composition substantially as hereinbefore particularly described with reference to the foregoing examples.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9523335.9 | 1995-11-15 | ||
| GB9523335A GB2307176A (en) | 1995-11-15 | 1995-11-15 | Anti-inflammatory clathrating agents for topical use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2237758A1 true CA2237758A1 (en) | 1997-05-22 |
Family
ID=10783900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002237758A Abandoned CA2237758A1 (en) | 1995-11-15 | 1996-11-13 | Topical compositions containing a beta-cyclodextrin and an amino polysaccharide |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0863761A1 (en) |
| AU (1) | AU719360B2 (en) |
| CA (1) | CA2237758A1 (en) |
| GB (1) | GB2307176A (en) |
| NZ (1) | NZ322119A (en) |
| WO (1) | WO1997017977A1 (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4443689A1 (en) * | 1994-12-08 | 1996-06-13 | Krauss Maffei Ag | Closing unit for an injection molding machine |
| GB9626963D0 (en) * | 1996-12-27 | 1997-02-12 | Everest Todd Res & Dev | Improved surgical dressings and method of preparation |
| TWI242015B (en) * | 1999-11-29 | 2005-10-21 | Akzo Nobel Nv | 6-mercapto-cyclodextrin derivatives: reversal agents for drug-induced neuromuscular block |
| EP1127574A1 (en) * | 2000-02-22 | 2001-08-29 | Food Industry Research and Development Institute | Use of chitinous materials for inhibiting cellular nitric oxide production |
| US6653294B2 (en) | 2000-02-29 | 2003-11-25 | Food Industry Research & Development Institute | Use of chitinous materials for inhibiting cellular nitric oxide production |
| US6440465B1 (en) * | 2000-05-01 | 2002-08-27 | Bioderm, Inc. | Topical composition for the treatment of psoriasis and related skin disorders |
| DE10126396A1 (en) * | 2001-05-31 | 2002-12-05 | Beiersdorf Ag | Cosmetic or dermatological preparations containing glucosamine, useful e.g. for treatment, care and prophylaxis of sensitive skin and treatment of inflammatory conditions such as eczema or psoriasis |
| LU91353B1 (en) * | 2007-08-08 | 2009-02-09 | Recipe Holding S A | Glucosamine 1200mg, sachet |
| CN104870001B (en) | 2012-11-15 | 2019-01-18 | 赛博尔泰克股份公司 | Delphinidin complex compound as anti-inflammatory or immunosupress effective component |
| US9511047B2 (en) | 2012-12-11 | 2016-12-06 | Sapiotec Gmbh | Delphinidin for combating melanoma cells |
| EP2907518A1 (en) * | 2014-02-14 | 2015-08-19 | SapioTec GmbH | Analgesic |
| EP2913366A1 (en) * | 2014-02-28 | 2015-09-02 | SapioTec GmbH | Anthocyanidin complex |
| US10835584B2 (en) * | 2016-06-17 | 2020-11-17 | Nuvothera, Inc. | Systems for treating dermal inflammatory conditions |
| CN113490691A (en) | 2019-01-03 | 2021-10-08 | 劣势者药物有限公司 | Cyclodextrin dimers, compositions thereof, and uses thereof |
| WO2021100044A1 (en) | 2019-11-20 | 2021-05-27 | Avgol Ltd. | Methods of merging cyclodextrin hosts with nonwoven finishing to form smart fabrics containing various beneficial agents and products made from the methods |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5423966B2 (en) * | 1972-11-11 | 1979-08-17 | ||
| JPS5788123A (en) * | 1980-11-20 | 1982-06-01 | Kotsukusu Jiyaagen | Beta-cyclodextrin as antiacne |
| JPS58126810A (en) * | 1981-12-24 | 1983-07-28 | Kaken Pharmaceut Co Ltd | Ophthalmic anti-inflammatory solution and preparation thereof |
| US4383992A (en) * | 1982-02-08 | 1983-05-17 | Lipari John M | Water-soluble steroid compounds |
| JPS61221120A (en) * | 1985-03-28 | 1986-10-01 | Nitto Electric Ind Co Ltd | Medical material for external use |
| JPH0613448B2 (en) * | 1985-07-02 | 1994-02-23 | 三省製薬株式会社 | Cutaneous elastic fibrosis preventive agent |
| JPH0249711A (en) * | 1988-08-11 | 1990-02-20 | Nikkei New Bijinesu Kk | Novel cream for foundation cosmetic |
| GB8910069D0 (en) * | 1989-05-03 | 1989-06-21 | Janssen Pharmaceutica Nv | Method of topically treating acne vulgaris |
| FR2647015B1 (en) * | 1989-05-17 | 1994-05-06 | Cird | AQUEOUS GEL BASED ON RETINOIC ACID AND ITS USE IN HUMAN MEDICINE AND COSMETICS |
| JPH04334321A (en) * | 1991-05-09 | 1992-11-20 | Unitika Ltd | Preventive for dermatic inflammation |
| DE4220736A1 (en) * | 1992-06-25 | 1994-01-05 | Puetter Medice Chem Pharm | Inclusion complexes of polymerized cyclodextrins with pharmaceutically active substances |
-
1995
- 1995-11-15 GB GB9523335A patent/GB2307176A/en not_active Withdrawn
-
1996
- 1996-11-13 CA CA002237758A patent/CA2237758A1/en not_active Abandoned
- 1996-11-13 NZ NZ322119A patent/NZ322119A/en unknown
- 1996-11-13 EP EP96938324A patent/EP0863761A1/en not_active Withdrawn
- 1996-11-13 WO PCT/GB1996/002768 patent/WO1997017977A1/en not_active Application Discontinuation
- 1996-11-13 AU AU75787/96A patent/AU719360B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU7578796A (en) | 1997-06-05 |
| GB9523335D0 (en) | 1996-01-17 |
| EP0863761A1 (en) | 1998-09-16 |
| AU719360B2 (en) | 2000-05-04 |
| GB2307176A (en) | 1997-05-21 |
| WO1997017977A1 (en) | 1997-05-22 |
| NZ322119A (en) | 1998-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |