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WO1997017977A1 - Topical compositions containing a beta-cyclodextrin and an amino polysaccharide - Google Patents

Topical compositions containing a beta-cyclodextrin and an amino polysaccharide Download PDF

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Publication number
WO1997017977A1
WO1997017977A1 PCT/GB1996/002768 GB9602768W WO9717977A1 WO 1997017977 A1 WO1997017977 A1 WO 1997017977A1 GB 9602768 W GB9602768 W GB 9602768W WO 9717977 A1 WO9717977 A1 WO 9717977A1
Authority
WO
WIPO (PCT)
Prior art keywords
cyclodextrin
composition
polysaccharide
amino
gel
Prior art date
Application number
PCT/GB1996/002768
Other languages
French (fr)
Inventor
Selwyn Everest-Todd
Original Assignee
Everest-Todd Research & Development Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Everest-Todd Research & Development Limited filed Critical Everest-Todd Research & Development Limited
Priority to EP96938324A priority Critical patent/EP0863761A1/en
Priority to AU75787/96A priority patent/AU719360B2/en
Priority to NZ322119A priority patent/NZ322119A/en
Publication of WO1997017977A1 publication Critical patent/WO1997017977A1/en

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

Definitions

  • 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.
  • 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.
  • 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.
  • 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 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 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.
  • 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.
  • glucosamine hydrochloride 50 Og of glucosamine hydrochloride 50. Og of dimethyl ⁇ . cyclodextrin made up to 1 litre with sterile water.
  • 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.
  • 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.
  • 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.
  • Example I_ 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 10 minutes after application and regeneration of dermal tissue was observed on the fourth day.
  • 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 IV The powder produced as in Example IV was incorporated in the layer of fabric used to produce sanitary wear.
  • Candida albicans known as nappy rash
  • Other applications for the reduction of infection by this organism are related to age and sex.
  • the dimethyl ⁇ . cyclodextrin and ⁇ . cyclodextrin may be exchanged without detracting from the principle of the invention.
  • the amino polysaccharides as a group display similar characteristics from a therapeutic standpoint although the chemical and or physical properties may differ.
  • a colloidal suspension was prepared from a combination of chitin, chitosan and glucosamine having a particle size of less than 5 microns in an aqueous solution of /3-cyclodextrin in the following manner:
  • 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 10cm 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.

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  • 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 β-cyclodextrin and an amino polysaccharide.

Description

TOPICAL COMPOSITIONS CONTAINING A BETA-CYCLODEXTRIN AND AN AMINO POLYSACCHARIDE
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 β- 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 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 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 I
50. Og of glucosamine hydrochloride 50. Og of dimethyl β . cyclodextrin made up to 1 litre with sterile water.
The solution was then added to a mixture of 1 kg. coconut oil and 40g of an organo phosphate ester emulsifier maintained at 50°C. After agitation and cooling this produced a lotion suitable for topical application to the skin to combat inflammation. Examp le I I
4. Og of Alcosorb polymers
10. Og glucosamine hydrochloride and
15. Og β . 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.
Example III
40g Alcosorb polymers lOOg glucosamine hydrochloride
150g dimethyl β. 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-(l-4) β-D-N-acetylglucosamine 50g β . 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.
The preparations illustrated but not limited by Examples I to IV were then subjected to a series of tests as demonstrated by the following examples. Exa ple 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 10 minutes after application and regeneration of dermal tissue was observed on the fourth day.
Example VI
A sachet, produced as in Example I_I, was immersed in 0.5 litres of sterile water for five (5) 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 III , 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 β . cyclodextrin and β . cyclodextrin may be exchanged without detracting from the principle of the invention. 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 of chitin, chitosan and glucosamine having a particle size of less than 5 microns in an aqueous solution of /3-cyclodextrin in the following manner:
40g chitin (poly(1-4) -N-acetyl-D-glucosamine)
40g chitosan (poly(1-4) -D-glucosamine)
20g glucosamine
The above ingredients were introduced with agitation into an aqueous solution containing β-cyclodextrin and the whole made up to a total volume of 1 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 10cm 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

CLAI S
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 β-cyclodextrin or dimethyl β- 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.
PCT/GB1996/002768 1995-11-15 1996-11-13 Topical compositions containing a beta-cyclodextrin and an amino polysaccharide WO1997017977A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP96938324A EP0863761A1 (en) 1995-11-15 1996-11-13 Topical compositions containing a beta-cyclodextrin and an amino polysaccharide
AU75787/96A AU719360B2 (en) 1995-11-15 1996-11-13 Topical compositions containing a beta-cyclodextrin and an amino polysaccharide
NZ322119A NZ322119A (en) 1995-11-15 1996-11-13 Topical emulsion based upon a polysaccharide containing amino groups for treatment of skin

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
WO1997017977A1 true WO1997017977A1 (en) 1997-05-22

Family

ID=10783900

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1996/002768 WO1997017977A1 (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)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5736169A (en) * 1994-12-08 1998-04-07 Krauss-Maffei Ag Closing apparatus for multiple-mold injection-molding system
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
USRE44733E1 (en) * 1999-11-29 2014-01-28 Merck Sharp & Dohme B.V. 6-mercapto-cyclodextrin derivatives:reversal agents for drug-induced neuromuscular block
EP2907518A1 (en) * 2014-02-14 2015-08-19 SapioTec GmbH Analgesic
EP2913366A1 (en) * 2014-02-28 2015-09-02 SapioTec GmbH Anthocyanidin complex
US9925274B2 (en) 2012-11-15 2018-03-27 Sapiotec Gmbh Delphinidin complex as an antiphlogistic or immunosuppressive active ingredient
US9949947B2 (en) 2012-12-11 2018-04-24 Sapiotec Gmbh Delphinidin for combating melanoma cells
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

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9626963D0 (en) * 1996-12-27 1997-02-12 Everest Todd Res & Dev Improved surgical dressings and method of preparation
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
US10835584B2 (en) 2016-06-17 2020-11-17 Nuvothera, Inc. Systems for treating dermal inflammatory conditions
US11279774B2 (en) 2019-01-03 2022-03-22 Underdog Pharmaceuticals, Inc. Cyclodextrin dimers, compositions thereof, and uses thereof

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FR2647015A1 (en) * 1989-05-17 1990-11-23 Cird RETINOIC ACID-BASED AQUEOUS GEL AND USE THEREOF IN HUMAN MEDICINE AND COSMETICS

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5736169A (en) * 1994-12-08 1998-04-07 Krauss-Maffei Ag Closing apparatus for multiple-mold injection-molding system
USRE44733E1 (en) * 1999-11-29 2014-01-28 Merck Sharp & Dohme B.V. 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
US9925274B2 (en) 2012-11-15 2018-03-27 Sapiotec Gmbh Delphinidin complex as an antiphlogistic or immunosuppressive active ingredient
US9949947B2 (en) 2012-12-11 2018-04-24 Sapiotec Gmbh Delphinidin for combating melanoma cells
EP2907518A1 (en) * 2014-02-14 2015-08-19 SapioTec GmbH Analgesic
WO2015121419A1 (en) * 2014-02-14 2015-08-20 Sapiotec Gmbh Analgesic
EP2913366A1 (en) * 2014-02-28 2015-09-02 SapioTec GmbH Anthocyanidin complex
WO2015128437A1 (en) * 2014-02-28 2015-09-03 Sapiotec Gmbh Anthocyanidin complex
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

Also Published As

Publication number Publication date
NZ322119A (en) 1998-09-24
AU7578796A (en) 1997-06-05
AU719360B2 (en) 2000-05-04
CA2237758A1 (en) 1997-05-22
EP0863761A1 (en) 1998-09-16
GB9523335D0 (en) 1996-01-17
GB2307176A (en) 1997-05-21

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