WO2005074883A1 - Aqueous compositions containing mixtures of synthetic polymers and biopolymers, useful in the treatment of skin and mucosal tissues dryness, and suitable as vehicles of active ingredients - Google Patents

Aqueous compositions containing mixtures of synthetic polymers and biopolymers, useful in the treatment of skin and mucosal tissues dryness, and suitable as vehicles of active ingredients Download PDF

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Publication number
WO2005074883A1
WO2005074883A1 PCT/EP2005/000856 EP2005000856W WO2005074883A1 WO 2005074883 A1 WO2005074883 A1 WO 2005074883A1 EP 2005000856 W EP2005000856 W EP 2005000856W WO 2005074883 A1 WO2005074883 A1 WO 2005074883A1
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Prior art keywords
carbopol
chitosan
compositions according
poloxamer
salts
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PCT/EP2005/000856
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French (fr)
Inventor
Adolfo Gasparetto
Giovanni Miniello
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Sinclair Pharmaceuticals Limited
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Publication of WO2005074883A1 publication Critical patent/WO2005074883A1/en

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    • 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
    • A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
    • 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
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers

Definitions

  • the present invention relates to aqueous compositions containing mixtures of synthetic polymers and biopolymers, useful in the treatment of skin and mucosal tissues dryness, and suitable as vehicles of active ingredients.
  • Bioadhesive formulations i.e. formulations which adhere to tissues, particularly to the mucosae, are object of extended research efforts in view of the advantages connected with their use in many therapeutical and cosmetic fields, particularly in the dermatological, ophthalmological, gynaecological and stomatological fields.
  • a bioadhesive formulation may in fact secure for a prolonged period the contact of the active ingredient with the mucosae, improving thereby the therapeutic effectiveness and allowing a reduction of the amount of the active ingredients.
  • Bioadhesive properties are usually imparted by synthetic or natural polymers.
  • natural bioadhesive polymers include polysaccharides from mammalian tissues (dermatan sulfate and chondroitin sulfate) as well as the polysaccharides of vegetable origin, mostly from algae, such as alginic acid, gellan and other related mucopolysaccharides, cellulose and derivatives thereof, chitosan and chitin.
  • bioadhesive polymers examples include polyethylene glycols, polyvinylpyrrolidone, polyvinylalcohol (PVA) and Caxbopols or Carbomers. The latter have particularly been used in the formulation of pharmaceutical compositions.
  • US 5.876.744 discloses bioadhesive compositions comprising a mixture of a specific Carbomer, Polycarbophil, and/or PVA with biopolymers such as hyal ⁇ ronic acid, alginic acid and dermatan sulphate.
  • bioadhesive and mucoadhesive aqueous composition are obtained by combining the following ingredients: (a) a polymer selected from Carbopol 974P NF, Carbopol 934 P, a poloxamer or mixtures thereof; (b) polyvinylalcohol or polyvinylpyrrolidone; (c) a biopolymer selected from Alginic acid, Chitosan, Chitin, Chitosan oligosaccharide ascorbic acid or salts thereof, said Chitosan having an average molecular weight ranging from about 50 to 20.000 kda; and (d) optionally one or more of the components selected from lecithins, wet grain extract, ascorbic or lactic acid and salts thereof.
  • compositions of the invention may be used for the rehydration of skin or mucous membranes and/or as vehicles of active principles suited for the topical administration.
  • the compositions of the invention preferably comprise: (a) Carbopol 974P NF or a mixture of Carbopol 974P NF with a Poloxamer; (b) Polyvinylalcohol or, when the component (a) includes a Poloxamer, polyvinylpyrrolidone; (c) Chitosan or chitosan oligosaccharide ascorbic acid (Chitoligo®).
  • Carbopol 974P NF is a cross-linked acrylic acid polymer.
  • This polymer is a high water absorbing power; it may be accordingly used in the form of calcium salt as a cathartic (Martindale, Extra Pharmacopeia, 29th Ed., Pharmaceutical Press, 1989).
  • the use of said polymer as moisturiser and humectant is disclosed in EP 0429156 Al and as a bioadhesive vehicle for the controlled release of active principles in US 4.615.697.
  • Poloxamers are block copolymers of ethylene oxide and propylene oxide (poly(oxypro ⁇ ylene-co-oxyethylene)glycols). They form thermoreversible gels in concentration range between 15% to 50%. This means they are liquids at cool temperature, but are gels at room or body temperature.
  • Poloxamers are commercially available under different trade-marks (Lutrol, Pluronic®); Poloxamer 407, having average molecular weight from 9.840 to 14.600, is particularly preferred according to the present invention.
  • a mixture of polyacrylic acid and poly (oxypropylene-co-oxyethylene) glycol is available under the trade-mark Smart Hydrogel®.
  • the amount of said synthetic polymers in the compositions of the invention are from 0.1 to 2% by weight, preferably from 0.2 to 1% for Carbopol 974P NF and 15% to 50% for poloxamers.
  • PVA or PVP is present in the compositions of the invention in amounts ranging from 0.1 to 3% by weight.
  • the chitosans can be obtained from chitin-containing organisms or from vegetables or algae (chitosan, alginic acid).
  • the chitosans are usually used in the form of sodium salt; however, they can be used also in the form of other commonly available salts, such as other alkali or alkaline-earth metal or ammonium salts.
  • Chitosan or derivatives thereof have preferably a molecular weight ranging from 50 to 20.000 kda.
  • the amount of chitosan in the compositions of the invention are from
  • compositions of the invention may also comprise ascorbic acid and/or lactic acid, preferably in an amount from 0.5 to 5% by weight.
  • the composition of the invention may also comprise an active ingredient suited for percutaneous or mucosal administration, for instance antimycotics, steroidal or non-steroidal anti-inflammatory agents, antibacterial agents, anti-histamines, antibiotics, antiglaucoma agents, vasoactive agents and disinfectants.
  • the compositions of the invention may be suitably applied to cutaneous, vaginal, gastroenteric, oral, eye and rectal tissues.
  • the compositions of the invention are prepared by adding a solution of PVA or PVP in water to a stirred emulsion of the synthetic polymer in water.
  • the addition is carried out preferably under reduced pressure.
  • the resulting mass is maintained under continuous stirring until a completely homogeneous phase is obtained.
  • the resulting mass is then cooled under vacuum to 30 ⁇ 2°C. At that temperature, the mass is maintained under stirring and in vacuo.
  • a 10% solution of chitosan in water is separately prepared stirring until a viscous, perfectly homogeneous and clear solution is obtained.
  • This solution is then added slowly and in a thin stream to the mass contained in the turboemulsifier, under continuous stirring and under constant vacuum. Agitation is continued until a perfectly homogeneous mass was obtained.
  • a gel of the desired density may be obtained by adding for example a 1% triethanolamine water solution. Stirring is continued until complete carbomers swelling and a perfectly homogeneous gel is obtained. Once the mass has gelled completely, stirring is stopped and the pressure inside the turboemulsif ⁇ er is slowly restored.
  • synthetic polymers such as CARBOPOL 974P NF and PVA, with alginic acid, chitosan or Chitin oligosaccharide ascorbic acid, yields compositions with a marked bioadhesive behaviour.
  • the invention is further detailed in the following Examples. EXAMPLE 1 Gynaecologic gel (by wt.
  • Gynaecologic solution (by wt. % composition)

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Gynecology & Obstetrics (AREA)
  • Reproductive Health (AREA)
  • Urology & Nephrology (AREA)
  • Dermatology (AREA)
  • Medicinal Preparation (AREA)

Abstract

The invention relates a bioadhesive and mucoadhesive aqueous composition comprising: (a) a polymer selected from Carbopol 974P NF, Carbopol 934 P, a poloxamer or mixtures thereof; (b) polyvinylalcohol or polyvinylpyrrolidone; (c) a biopolymer selected from Alginic acid, Chitosan, Chitin, Chitosan oligosaccharide ascorbic acid or salts thereof, said Chitosan having an average molecular weight ranging from about 50 to 20.000 kda; and (d) optionally one or more of the components selected from lecithins, wet grain extract, ascorbic or lactic acid and salts thereof.

Description

AQUEOUS COMPOSITIONS CONTAINING MIXTURES OF SYNTHETIC POLYMERS AND BIOPOLYMERS, USEFUL IN THE TREATMENT OF SKIN AND MUCOSAL TISSUES DRYNESS. AND SUITABLE AS VEHICLES OF ACTIVE INGREDIENTS
FIELD OF THE INVENTION The present invention relates to aqueous compositions containing mixtures of synthetic polymers and biopolymers, useful in the treatment of skin and mucosal tissues dryness, and suitable as vehicles of active ingredients. BACKGROUND OF THE INVENTION Bioadhesive formulations, i.e. formulations which adhere to tissues, particularly to the mucosae, are object of extended research efforts in view of the advantages connected with their use in many therapeutical and cosmetic fields, particularly in the dermatological, ophthalmological, gynaecological and stomatological fields. A bioadhesive formulation may in fact secure for a prolonged period the contact of the active ingredient with the mucosae, improving thereby the therapeutic effectiveness and allowing a reduction of the amount of the active ingredients. Bioadhesive properties are usually imparted by synthetic or natural polymers. Examples of natural bioadhesive polymers include polysaccharides from mammalian tissues (dermatan sulfate and chondroitin sulfate) as well as the polysaccharides of vegetable origin, mostly from algae, such as alginic acid, gellan and other related mucopolysaccharides, cellulose and derivatives thereof, chitosan and chitin. Examples of synthetic bioadhesive polymers include polyethylene glycols, polyvinylpyrrolidone, polyvinylalcohol (PVA) and Caxbopols or Carbomers. The latter have particularly been used in the formulation of pharmaceutical compositions. US 5.876.744 discloses bioadhesive compositions comprising a mixture of a specific Carbomer, Polycarbophil, and/or PVA with biopolymers such as hyalυronic acid, alginic acid and dermatan sulphate. Similar bioadhesive formulations, always comprising Carbopols or carbomers as an essential component for the bioadhesive properties are disclosed, for example, in WO 97/24109, WO 98/5303, WO 00/47144, WO 95/5163, EP 581581. SUMMARY OF THE INVENTION It has now been found that particularly advantageous and effective bioadhesive and mucoadhesive aqueous composition are obtained by combining the following ingredients: (a) a polymer selected from Carbopol 974P NF, Carbopol 934 P, a poloxamer or mixtures thereof; (b) polyvinylalcohol or polyvinylpyrrolidone; (c) a biopolymer selected from Alginic acid, Chitosan, Chitin, Chitosan oligosaccharide ascorbic acid or salts thereof, said Chitosan having an average molecular weight ranging from about 50 to 20.000 kda; and (d) optionally one or more of the components selected from lecithins, wet grain extract, ascorbic or lactic acid and salts thereof. Said compositions may be used for the rehydration of skin or mucous membranes and/or as vehicles of active principles suited for the topical administration. DETAILED DESCRIPTION OF THE INVENTION The compositions of the invention preferably comprise: (a) Carbopol 974P NF or a mixture of Carbopol 974P NF with a Poloxamer; (b) Polyvinylalcohol or, when the component (a) includes a Poloxamer, polyvinylpyrrolidone; (c) Chitosan or chitosan oligosaccharide ascorbic acid (Chitoligo®). Carbopol 974P NF is a cross-linked acrylic acid polymer. The main characteristic of this polymer is a high water absorbing power; it may be accordingly used in the form of calcium salt as a cathartic (Martindale, Extra Pharmacopeia, 29th Ed., Pharmaceutical Press, 1989). The use of said polymer as moisturiser and humectant is disclosed in EP 0429156 Al and as a bioadhesive vehicle for the controlled release of active principles in US 4.615.697. Poloxamers are block copolymers of ethylene oxide and propylene oxide (poly(oxyproρylene-co-oxyethylene)glycols). They form thermoreversible gels in concentration range between 15% to 50%. This means they are liquids at cool temperature, but are gels at room or body temperature. Poloxamers are commercially available under different trade-marks (Lutrol, Pluronic®); Poloxamer 407, having average molecular weight from 9.840 to 14.600, is particularly preferred according to the present invention. A mixture of polyacrylic acid and poly (oxypropylene-co-oxyethylene) glycol is available under the trade-mark Smart Hydrogel®. The amount of said synthetic polymers in the compositions of the invention are from 0.1 to 2% by weight, preferably from 0.2 to 1% for Carbopol 974P NF and 15% to 50% for poloxamers. PVA or PVP is present in the compositions of the invention in amounts ranging from 0.1 to 3% by weight. The chitosans can be obtained from chitin-containing organisms or from vegetables or algae (chitosan, alginic acid). The chitosans are usually used in the form of sodium salt; however, they can be used also in the form of other commonly available salts, such as other alkali or alkaline-earth metal or ammonium salts. Chitosan or derivatives thereof have preferably a molecular weight ranging from 50 to 20.000 kda. The amount of chitosan in the compositions of the invention are from
0.05 to 10% by weight. The compositions of the invention may also comprise ascorbic acid and/or lactic acid, preferably in an amount from 0.5 to 5% by weight. If desired, the composition of the invention may also comprise an active ingredient suited for percutaneous or mucosal administration, for instance antimycotics, steroidal or non-steroidal anti-inflammatory agents, antibacterial agents, anti-histamines, antibiotics, antiglaucoma agents, vasoactive agents and disinfectants. The compositions of the invention may be suitably applied to cutaneous, vaginal, gastroenteric, oral, eye and rectal tissues. The compositions of the invention are prepared by adding a solution of PVA or PVP in water to a stirred emulsion of the synthetic polymer in water. The addition is carried out preferably under reduced pressure. The resulting mass is maintained under continuous stirring until a completely homogeneous phase is obtained. The resulting mass is then cooled under vacuum to 30 ± 2°C. At that temperature, the mass is maintained under stirring and in vacuo. A 10% solution of chitosan in water is separately prepared stirring until a viscous, perfectly homogeneous and clear solution is obtained. This solution is then added slowly and in a thin stream to the mass contained in the turboemulsifier, under continuous stirring and under constant vacuum. Agitation is continued until a perfectly homogeneous mass was obtained. O 2005/074883
A gel of the desired density may be obtained by adding for example a 1% triethanolamine water solution. Stirring is continued until complete carbomers swelling and a perfectly homogeneous gel is obtained. Once the mass has gelled completely, stirring is stopped and the pressure inside the turboemulsifϊer is slowly restored. The combination of synthetic polymers, such as CARBOPOL 974P NF and PVA, with alginic acid, chitosan or Chitin oligosaccharide ascorbic acid, yields compositions with a marked bioadhesive behaviour. The invention is further detailed in the following Examples. EXAMPLE 1 Gynaecologic gel (by wt. % composition) PVP/PVA 1.50 Triethanolamine 1.50 Carbopol 974P NF® 1.00 Poloxamer (407 - Pluronic) 20.00 Chitoligo® 1.00 Triclosan 0.20 Chlorhexidine 0.005 Propylene glycol 15.00 Demineralized water q.s. to 100.00 EXAMPLE 2 Dermatologic gel (by wt. % composition) PVP/PVA 1.50 Triethanolamine 1.50 Carbopol 974P NF® 1.00 Poloxamer (407 - Pluronic) 15.0 Chitoligo® 2.00 Triclosan 0.30 Cetrimide 0.50
Propylene glycol 15.00
Demineralized water q.s. to 100.00 EXAMPLE 3 Gynaecologic gel (by wt. % composition)
Chi orhexi dine 0.05
Propylene glycol 15.00
Ethyl p-hydroxybenzoate 0.10
*Eumulgin HRE 40® 1.00 Triethanolamine 0.20
Carbopol 974P NF® 1.00
PVP/PVA 1.50
Poloxamer (407 - Pluronic) 15.0
Policresulene 0.10 Miconazole nitrate 0.20
Chitosan 0.06
D eminer alized water q . s . to 100.00 * Eumulgin HRE 40 : polyoxyethylenated castor oil EXAMPLE 4 Dermatologic gel (by wt. % composition) Cetrimide 0.50 Triclosan 0.30 Propylene glycol 15.00 ♦Eumulgin HRE 40® 1.00 Triethanolamine 0.275 Carbopol 974P NF® 1.00 Poloxamer (407 - Pluronic) 15.0 PVP 1.00 Miconazole nitrate 0.20 Chitosan 0.06 Meclocicline 0.05 Demineralized water q.s. to 100.00 EXAMPLE 5
Gynaecologic solution (by wt. % composition)
2-Phenylethanol 0.30
Triclosan 0.20
Propylene glycol 15.00
Eumulgin HRE 40® 1.00
Hy droxy ethy lc ellul o s e 0.50
Lactic acid (80%) 2.00
Triethanolamine 2.30
Carbopol 974P NF® 0.20
Poloxamer (407 - Pluronic) 15.0
PVP 0.30
Fluocinolone cetonide 0.15 Miconazole nitrate 0.20 Chitosan 0.20 Demineralized water q.s. to 100.00 EXAMPLE 6 Dermatologic gel (by wt. % composition) 2-Phenylethanol 0.30 Triclosan 0.20 Propylene glycol 15.00 Eumulgin HRE 40® 1.00 Carbopol 974P NF® 1.00 Poloxamer (407 - Pluronic) 15.0 PVP/PVA 1.50 Cloramphenicol 0.15 Miconazole nitrate 0.20 Chitoligo 1.00 Triethanolamine 0.25 Demineralized water q.s. to 100.00 EXAMPLE 7 Gynaecologic gel (by wt. % composition) PVP/PVA 1.50 Carbopol 974P NF® 1.00 Poloxamer (407 - Pluronic) 15.0 OR) Chitoligo 1.00 Cloramphenicol 0.10 N,N'-bis-(2-hydroxyethyl)-nonandiamide 0.20 Glycerin 10.00 Sodium Dodecylsulfate 1.00 Hydrogenate castor oil (40)OE* 1.00 Tocopheryl acetate 0.50 Phenylethy alcohol 0.15 Triclosan 0.20 Sodium hydroxide (30% by wt. solution) 0.20 Demineralized water q.s. to 100.00 *Hydrogenate castor oil (40) is polyxyethylenated with 40 moles ethyl ene oxide/mole.

Claims

1. A bioadhesive and mucoadhesive aqueous composition comprising: (a) a polymer selected from Carbopol 974P NF, Carbopol 934 P, a poloxamer or mixtures thereof; (b) polyvinylalcohol or polyvinylpyrrolidone; (c) a biopolymer selected from Alginic acid, Chitosan, Chitin, Chitosan oligosaccharide ascorbic acid or salts thereof, said Chitosan having an average molecular weight ranging from about 50 to 20.000 kda; and (d) optionally one or more of the components selected from lecithins, wet grain extract, ascorbic or lactic acid and salts thereof.
2. Compositions according to claim 1 comprising: (a) Carbopol 974P NF or a mixture of Carbopol 974P NF with a Poloxamer; (b) Polyvinylalcohol or, when the component (a) includes a Poloxamer, polyvinylpyrrolidone; (c) Chitosan or chitosan oligosaccharide ascorbic acid (Chitoligo®).
3. Compositions according to claims 1 or 2 wherein Carbopol 974P NF is present in an amount ranging from 0.1 to 2% by weight.
4. Compositions according to claims 1, 2 or 3 wherein Poloxamer is present in an amount ranging from 15%» to 50%>.
5. Compositions according to any one of claims 1 to 4 wherein PVA is present in an amount ranging from 0.1 to 3% by weight.
6. Compositions according to one or more of claims 1-5 wherein the biopolymer is present in an amount ranging from 0.05%> to 10%> by weight.
7. Compositions according to one or more of claims 1-6, further comprising lecithin or wet grain extract.
8. Compositions according to one or more of claims 1-7, further comprising an active ingredient suited for percutaneous absorption.
9. Compositions according to claim 8 wherein the active ingredient is selected from antimycotics, steroid or non-steroid anti-inflammatory agents, antibacterial agents, anti-histamines, antibiotics, antiglaucoma agents, vasoactive agents and disinfectants.
PCT/EP2005/000856 2004-01-29 2005-01-28 Aqueous compositions containing mixtures of synthetic polymers and biopolymers, useful in the treatment of skin and mucosal tissues dryness, and suitable as vehicles of active ingredients WO2005074883A1 (en)

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100758636B1 (en) 2006-12-19 2007-09-13 고려대학교 산학협력단 Bioadhesive conjugate polymers and process for preparation thereof
WO2010119387A2 (en) * 2009-04-13 2010-10-21 Sulur Subramaniam Vanangamudi A medicinal cream made using miconazole nitrate, fluticasone propionate, and chitosan, and a process to make the same
WO2010119368A2 (en) * 2009-04-13 2010-10-21 Sulur Subramaniam Vanangamudi A medicinal cream made using miconazole nitrate and chitosan, and a process to make the same
WO2011027246A1 (en) * 2009-09-03 2011-03-10 Sulur Subramaniam Vanangamudi A cream comprising miconazole nitrate and a biopolymer for the treatment of diaper rash
CN101623251B (en) * 2009-08-11 2011-06-22 湖北穆兰同大科技有限公司 Gynecological antibacterial gel bionic propellant
EP2742932A1 (en) * 2012-12-17 2014-06-18 Laboratorios Ojer Pharma S.L. Gel compositions
CN107080733A (en) * 2017-04-17 2017-08-22 滨州医学院附属医院 A kind of miconazole nitrate chitosan vagina slowly-releasing gel and preparation method thereof
IT201800003872A1 (en) * 2018-03-22 2019-09-22 Dtech Soc A Responsabilita Limitata PRODUCT FOR THERAPEUTIC TREATMENT FOR THE PREVENTION AND TREATMENT OF PATHOLOGIES OF THE ORAL CAVITY, TEETH AND DENTAL IMPLANTS
US10576043B2 (en) * 2017-08-10 2020-03-03 Avro Life Sciences, Inc. Transdermal drug delivery system
CN111437394A (en) * 2020-04-07 2020-07-24 长春吉原生物科技有限公司 Bionic excrement and preparation method and application thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991006289A1 (en) * 1989-10-31 1991-05-16 Watson Laboratories, Inc. Mucoadhesive carrier for delivery of therapeutical agent
EP0663212A2 (en) * 1994-01-13 1995-07-19 Hydromer, Inc. Gels formed by the interaction of polyvinylpyrrolidone with chitosan derivatives
US5876744A (en) * 1994-08-01 1999-03-02 Lifegroup S.P.A. Highly bioadhesive and mucoadhesive compositions containing polyvinyl alcohol, polycarbophil and biopolymer for the treatment of skin conditions and as vehicles for active ingredients
US20030060486A1 (en) * 2001-02-15 2003-03-27 Access Pharmaceuticals, Inc. Liquid formulations for the prevention and treatment of mucosal diseases and disorders
US20030133884A1 (en) * 2000-03-17 2003-07-17 Sug-Youn Chang Patches for teeth whitening

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991006289A1 (en) * 1989-10-31 1991-05-16 Watson Laboratories, Inc. Mucoadhesive carrier for delivery of therapeutical agent
EP0663212A2 (en) * 1994-01-13 1995-07-19 Hydromer, Inc. Gels formed by the interaction of polyvinylpyrrolidone with chitosan derivatives
US5876744A (en) * 1994-08-01 1999-03-02 Lifegroup S.P.A. Highly bioadhesive and mucoadhesive compositions containing polyvinyl alcohol, polycarbophil and biopolymer for the treatment of skin conditions and as vehicles for active ingredients
US20030133884A1 (en) * 2000-03-17 2003-07-17 Sug-Youn Chang Patches for teeth whitening
US20030060486A1 (en) * 2001-02-15 2003-03-27 Access Pharmaceuticals, Inc. Liquid formulations for the prevention and treatment of mucosal diseases and disorders

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100758636B1 (en) 2006-12-19 2007-09-13 고려대학교 산학협력단 Bioadhesive conjugate polymers and process for preparation thereof
WO2010119387A2 (en) * 2009-04-13 2010-10-21 Sulur Subramaniam Vanangamudi A medicinal cream made using miconazole nitrate, fluticasone propionate, and chitosan, and a process to make the same
WO2010119368A2 (en) * 2009-04-13 2010-10-21 Sulur Subramaniam Vanangamudi A medicinal cream made using miconazole nitrate and chitosan, and a process to make the same
WO2010119387A3 (en) * 2009-04-13 2011-05-26 Sulur Subramaniam Vanangamudi A medicinal cream made using miconazole nitrate, fluticasone propionate, and chitosan, and a process to make the same
WO2010119368A3 (en) * 2009-04-13 2011-05-26 Sulur Subramaniam Vanangamudi A medicinal cream made using miconazole nitrate and chitosan, and a process to make the same
US20120035233A1 (en) * 2009-04-13 2012-02-09 Apex Laboratories Private Limited Medicinal cream made using miconazole nitrate and chitosan and a process to make the same
CN101623251B (en) * 2009-08-11 2011-06-22 湖北穆兰同大科技有限公司 Gynecological antibacterial gel bionic propellant
WO2011027246A1 (en) * 2009-09-03 2011-03-10 Sulur Subramaniam Vanangamudi A cream comprising miconazole nitrate and a biopolymer for the treatment of diaper rash
JP2016502993A (en) * 2012-12-17 2016-02-01 ラボラトリオス オヘール ファルマ エセ．エレ． Gel composition
KR102207658B1 (en) 2012-12-17 2021-01-26 라보라토리오스 오제르 파르마, 에스.엘. Gel compositions
KR20150095898A (en) * 2012-12-17 2015-08-21 라보라토리오스 오제르 파르마, 에스.엘. Gel compositions
CN104918605A (en) * 2012-12-17 2015-09-16 欧洁尔药物实验室有限公司 Gel compositions
EP2742932A1 (en) * 2012-12-17 2014-06-18 Laboratorios Ojer Pharma S.L. Gel compositions
AU2013363788B2 (en) * 2012-12-17 2016-06-23 Laboratorios Ojer Pharma S.L. Gel compositions
US9486403B2 (en) 2012-12-17 2016-11-08 Laboratorios Ojer Pharma, S.L. Gel compositions
WO2014095705A1 (en) * 2012-12-17 2014-06-26 Laboratorios Ojer Pharma, S.L. Gel compositions
CN104918605B (en) * 2012-12-17 2017-09-15 欧洁尔药物实验室有限公司 Gel combination
CN107080733A (en) * 2017-04-17 2017-08-22 滨州医学院附属医院 A kind of miconazole nitrate chitosan vagina slowly-releasing gel and preparation method thereof
US10576043B2 (en) * 2017-08-10 2020-03-03 Avro Life Sciences, Inc. Transdermal drug delivery system
CN111315438A (en) * 2017-08-10 2020-06-19 爱肤柔生命科学公司 Transdermal drug delivery system
US11324705B2 (en) 2017-08-10 2022-05-10 Avro Life Sciences, Inc. Transdermal drug delivery system
WO2019180530A1 (en) * 2018-03-22 2019-09-26 Dtech - Società A Responsabilità Limitata Antiseptic and/or anti-inflammatory gel for treatment of oral cavity diseases comprising polyvinyl alcohol and polyacids
IT201800003872A1 (en) * 2018-03-22 2019-09-22 Dtech Soc A Responsabilita Limitata PRODUCT FOR THERAPEUTIC TREATMENT FOR THE PREVENTION AND TREATMENT OF PATHOLOGIES OF THE ORAL CAVITY, TEETH AND DENTAL IMPLANTS
CN111437394A (en) * 2020-04-07 2020-07-24 长春吉原生物科技有限公司 Bionic excrement and preparation method and application thereof

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