US3627871A - Therapeutic compositions for topical application - Google Patents

Therapeutic compositions for topical application Download PDF

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Publication number
US3627871A
US3627871A US723245A US3627871DA US3627871A US 3627871 A US3627871 A US 3627871A US 723245 A US723245 A US 723245A US 3627871D A US3627871D A US 3627871DA US 3627871 A US3627871 A US 3627871A
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United States
Prior art keywords
film
skin
compositions
topical application
forming
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.)
Expired - Lifetime
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US723245A
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English (en)
Inventor
Michael John Groves
John Neville Hague
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boots Co PLC
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Boots Pure Drug Co Ltd
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Assigned to BOOTS COMPANY PLC THE reassignment BOOTS COMPANY PLC THE CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE MARCH 15, 1982. Assignors: BOOTS COMPANY LIMITED THE
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0061—Use of materials characterised by their function or physical properties
    • A61L26/0076—Sprayable compositions
    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7015—Drug-containing film-forming compositions, e.g. spray-on
    • 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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
    • A61L26/0014—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0061—Use of materials characterised by their function or physical properties
    • A61L26/0066—Medicaments; Biocides
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/22—Lipids, fatty acids, e.g. prostaglandins, oils, fats, waxes
    • A61L2300/222—Steroids, e.g. corticosteroids
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/41—Anti-inflammatory agents, e.g. NSAIDs

Definitions

  • compositions suitable for topical application which contain medicaments and which ,dry when applied to the skin to give a flexible, nontacky adherent, substantially water-vapor impermeable film capable of releasing said medicaments to the underlying skin.
  • the preferred film-forming composition comprises an aqueous emulsion of a polyvinylidene chloride and a medicament such as an anti-inflammatory steroid.
  • This invention relates to improvements in therapeutic compositions for topical application. More particularly it relates to novel, occlusive film-forming cream bases and topical spray compositions.
  • Medicaments may be applied to the surface of the skin in solution or suspended in liquid vehicles, as emulsions in the form of lotions or water-miscible creams, as solutions or suspensions in fatty materials in the form of ointments and as dusting powders.
  • Such formulations are widely used for application of topical medicaments and are generally satisfactory.
  • certain topical medicaments which are even more efiective in their action on certain skin conditions if the site of application is covered by an occlusive'dressing immediately after application of the medicament. Occlusive dressings of this nature are thought to operate because there is no loss of water from the site of the application and the skin is made more permeable to the medicament.
  • Anti-inflammatory steroids are particularly active when applied under an occlusive dressing in this way.
  • the usual occlusive dressings which have been used hitherto include polyethylene film or Saran film (Trade Name), a commercially available occlusive film, the use of which is described by McKenzie and Stoughton, Arch. Derm. 1962, 86, 608. Although the use of such film is reported to give a hundredfold increase in the absorption of the drug, the dressing is cumbersome and areas of skin are unnecessarily covered by the large film wraps.
  • topical film-forming compositions which may contain medicaments and which rapidly dry when applied to the skin to give nonsensitizing, hard-wearing, flexible, substantially water-vapor impermeable films which release medicaments contained therein to the underlying skin.
  • compositions according to the invention comprise a fluid pharmaceutically acceptable carrier and a polymer that will form, on spreading the composition at a temperature below 35 or 40 C., a flexible nontacky adherent film that is substantially water-vapor impermeable, and a medicament, the polymer being present as an aqueous emulslon.
  • the viscosity of the compositions may vary from a thick paste to a low viscous liquid that can be sprayed.
  • the more fluid compositions may be dispensed from conventional containers such as plastic deformable bottles and mechanical sprays; preferred formulations are in the form of selfpropelled, aerosol sprays using compatible propellants.
  • the compositions are generally applied so as to form a thin film and this film must not only be substantially water-vapor impermeable but it must also be adherent and flexible, that is to say it must not crack away from the skin quickly after application.
  • plasticizer Most polymeric materials require the inclusion of a plasticizer in order that their films shall be sufficiently flexible. Some polymers can, however, be used without a plasticizer being included. Such polymers are generally copolymers, some grades of the copolymer formed from ethylene and vinyl chloride being an example. When a plasticizer is included in compositions according to the invention it may either be an internal plasticizer or it may be an external plasticizer. lntemally plasticized polymers are copolymers containing a small amount of a copolymerized monomer that plasticizes the remainder of the polymer.
  • the polymers used in compositions according to the invention are generally hydrophobic, and thus do not contain large numbers of hydrophilic groups, such as acetate groups.
  • a suitable polymeric film-forming agent is polyethylene, which is commercially available in the form of emulsions or self-emulsifying, spray-dried powder. Many grades of polyvinylidene chloride are also suitable and we have obtained the best results with this polymer when it has been internally plasticized especially with a small proportion of acrylamide. Externally plasticized polyvinylidene chloride can also be used.
  • Other polymeric film-forming agents suitable for use in the topical formulations include polyvinyl chloride, polystyrene, acrylic acid polymers and butadiene polymers.
  • Some film-forming polymers will only form films at relatively high temperatures; for example, the polyvinylidene chloride polymer emulsion available under the Trade Name Polidene 941 will not form satisfactory films below a temperature of about C.
  • the lowest temperature at which the polymer emulsion will form a film when thinly applied to a surface is defined as the minimum film-fonning temperature.”
  • the polymer emulsions which are suitable for preparing the compositions according to the invention have a minimum filmforming temperature which is not appreciably more than, and is preferably less than, the temperature of the body surface. For practical purposes, a minimum film-forming temperature of below 40 and usually below 35 C., is desirable.
  • compositions according to the invention may be included in the compositions according to the invention.
  • additives such as pharmaceutically acceptable viscolizers.
  • Other pharmaceutically acceptable ingredients of topical compositions such as buffering agents, opacifying agents and preservatives may be included in the compositions according to the invention.
  • composition When the composition is to be a spray it will generally also contain components such as aerosol propellants and suspending agents.
  • the carrier need be liquid, but some at least of them must be liquid in order that the carrier as a whole has fluid properties and that a skin shall be formed on spreading.
  • the polymer is mixed with the other components of the composition while the polymer is in the form of an aqueous emulsion, in which event the majority of the liquid carrier is generally made up of the aqueous medium of the emulsion.
  • compositions according to the invention are nontacky and adherent to the skin and are substantially impermeable to water vapor, but release drugs incorporated therein to the underlying surface. This is surprising since no one has previously been able to incorporate steroids into compositions which could be sprayed on to the skin surface to provide an impermeable film and yet from which the steroid will be released.
  • Additional ingredients may be included to modify the consistency of the ointments such as polyvinylpyrrolidone or to control the drying time of the ointments after application such as glycerol.
  • emulsions of polyvinylidene chloride and its copolymers we find emulsions of polyvinylidene chloride and its copolymers to be very satisfactory. However, these are generally too free flowing to be used as ointment bases and sprays and so we generally prefer to include in the carrier a pharmaceutically acceptable viscolizer when such an emulsion is used.
  • the emulsions suitable for preparing the ointment bases according to the invention have been selected by use of the Payne permeability test, the use of which is described in the Paint Research Memorandum No. 234, 1956, l 1, 92.
  • Material under test is cast or spread on to a supporting medium, usually filter paper, dried and clamped on to a cup containing a desiccant.
  • the assembly is placed in an atmosphere saturated with water vapor and the gain in weight is followed as a function of time.
  • the permeability of the film is given by the expression weight of cup in grams in T hours and F thickness of film in cm. after drying.
  • Emulsion (Trade Name) Permeability x lo g. days/cm.
  • Polidene 905 emulsions have been found to be pharmaceutically acceptable and the dried films release drugs contained therein to underlying skin. These emulsions contain 0.3 percent of acrylamide as copolymer. Polidene 9ll emulsions which contain no internal plasticizer have also been used.
  • Suitable viscolizers include finely divided silica, colloidal aluminum magnesium silicate, bentonite, attapulgite, agar, acacia, tragacanth, pectin, gum gatto, gelatin, hydroxyethylcellulose, sodium carboxyethylcellulose, methylcellulose, natural gums of bacterial origin, polyvinyl alcohol, polyvinylpyrrolidone, carboxypolymethylenes; polyethoxy homopolymers and methylvinylether/maleic anhydride copolymers.
  • viscolizers we prefer to add viscolizers to give a product having a viscosity range of 10-50 poises and especially -35 poises at a shear rate of 125 sec.l; we particularly prefer to use hydroxyethylcellulose.
  • concentration of hydroxyethylcellulose in the ointment base may vary within the range of 0.25-l .5 percent w/w.
  • Aerosol compositions according to the invention may be propelled by conventional gaseous propellants such as nitrous oxide, nitrogen and carbon dioxide which are compatible with the polymeric base and the active ingredients.
  • gaseous propellants such as nitrous oxide, nitrogen and carbon dioxide which are compatible with the polymeric base and the active ingredients.
  • the spray compositions contain one or more viscolizers of the types already described but at a lower concentration than used in the creams.
  • the ointment bases and topical spray bases according to the invention may be used for applying topically any drug which is compatible with the bases and which has an improved activity when the skin is in a very moist condition.
  • the bases are especially advantageous for the topical application of anti-inflammatory steroids such as hydrocortisone, prednisolone, triamcinolone, triamcinolone acetonide, fluocinolone acetonide, betamethasone, dexamethasone, flurandrenolone, flumethasone, 6a-methylprednisolone, fiuperolone, beclomethasone, fluocortolone and 2l-desoxyprednisolone.
  • anti-inflammatory steroids such as hydrocortisone, prednisolone, triamcinolone, triamcinolone acetonide, fluocinolone acetonide, betamethasone, dexamethasone, flurandrenolone, flumethasone, 6a-methyl
  • Organic and inorganic esters of the above compounds which may also be used as active ingredients include hydrocortisone 2l-acetate prednisolone 2l-pivalate, prednisolone 2!- phosphate, betamethasone l7a-valerate, flumethasone 2lpivalate, fluperolone 21-acetate, 6a-methylprednisolone 2lacetate, beclomethasone l7a,21-dipropionate, fluocortolone 2l-caproate and l7a-esters of 2l-desoxyprednisolone, especially 2 l -desoxyprednisolone l 7a-propionate.
  • topical compositions may include other compatible, active ingredients including antibiotics such as gramicidin, neomycin, kanamycin, the tetracyclines, chloramphenicol, polymixin, amphomycin, framycetin, gentamycin, bacitracin and nystatin.
  • antibiotics such as gramicidin, neomycin, kanamycin, the tetracyclines, chloramphenicol, polymixin, amphomycin, framycetin, gentamycin, bacitracin and nystatin.
  • antibacterial and antifungal agents may be included such as iodochlorhydroxyquinoline, coal tar fractions, di-iodohydroxyquinoline, phenylmercuric dinaphthylmethane disulphonate, chlorphenesin, salicylic acid, buclosamide, halquinol, hexachlorophane, clemizole, chlorquinaldol, cetrimide, cetylpyridinium chloride, benzalkonium chloride and domiphen bromide.
  • Local anesthetic agents such as dibucaine hydrochloride, amethocaine and amylocaine may also be included in the compositions according to the invention.
  • External plasticizers for use with aqueous polyvinylidene chloride emulsions include dimethyl phthalate, diethyl phthalate, dibutyl phthalate, di-isopropyl adipate, diethyl sebacate, isopropyl palmitate, hexylene glycol, benzyl alcohol and hexadecyl alcohol but these are not to be construed as limiting.
  • compositions according to the invention may be included in the compositions according to the invention.
  • Citric acid and its salts are particularly valuable as buffering agents as they have the advantage of being antioxidants and may stabilize the compositions by two distinct mechanisms.
  • Additional ingredients may be included to modify the consistency of the ointments such as polyvinylpyrrolidone or to control the drying time of the ointments after application such as glycerol.
  • the topical sprays according to the invention may be applied to the skin surface by conventional methods, e.g., from squeeze-bottles, mechanical sprays or by self-propelled aerosol sprays. It is important that in the case of aerosol sprays the propellant should have no solvent effect on the film-forming polymer or the characteristics of the formulation may be adversely affected. For this reason it is preferred that compatible gaseous propellants such as nitrous oxide, nitrogen and carbon dioxide be used.
  • gaseous propellants such as nitrous oxide, nitrogen and carbon dioxide be used.
  • the ointments according to the present invention are not applied to the skin in the same way as are conventional ointments or creams.
  • Conventional formulations are either massaged into the skin when no dressing is to be used, or are spread on the skin and covered by a dressing in order to prevent the soiling of clothes or removal of the ointment by contact with external objects.
  • the compositions of the present invention are spread or sprayed thinly on the surface of the skin and allowed to dry to give a thin film.
  • the film is nontacky, flexible and will stay on the skin for 2-5 days if not washed. Washing with soap and water easily removes the film when required. lf too thick a layer of film-forming cream or spray is applied to the skin the resultant film will crack and tend to peel off.
  • a pharmaceutical composition for topical application to the skin comprising an anti-inflammatory steroid and a fluid pharmaceutically acceptable carrier therefor, which carrier comprises an aqueous emulsion of a polyvinyltdine chloride

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Materials Engineering (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US723245A 1967-04-27 1968-04-22 Therapeutic compositions for topical application Expired - Lifetime US3627871A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB7494/68A GB1213295A (en) 1967-04-27 1967-04-27 Improvements in therapeutic compositions for topical application
GB1948067 1967-04-27

Publications (1)

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US3627871A true US3627871A (en) 1971-12-14

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US723245A Expired - Lifetime US3627871A (en) 1967-04-27 1968-04-22 Therapeutic compositions for topical application

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US (1) US3627871A (enrdf_load_stackoverflow)
CH (1) CH497897A (enrdf_load_stackoverflow)
DE (1) DE1767326A1 (enrdf_load_stackoverflow)
DK (1) DK120859B (enrdf_load_stackoverflow)
FR (1) FR7919M (enrdf_load_stackoverflow)
GB (1) GB1213295A (enrdf_load_stackoverflow)
NL (1) NL6805856A (enrdf_load_stackoverflow)
NO (1) NO124623B (enrdf_load_stackoverflow)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4102995A (en) * 1976-05-13 1978-07-25 Westwood Pharmaceuticals Inc. Tar gel formulation
US4113854A (en) * 1977-01-10 1978-09-12 Minnesota Mining And Manufacturing Company Prophylactic treatment of mastitis
WO1982000099A1 (en) * 1980-07-09 1982-01-21 Key Pharma Polymeric diffusion matrix for administration of drugs
US4321252A (en) * 1979-08-14 1982-03-23 Key Pharmaceuticals, Inc. Polymeric diffusion matrix containing ester derivatives of estradiol
US4482533A (en) * 1982-01-11 1984-11-13 Key Pharmaceuticals, Inc. Polymeric diffusion matrix containing propranolol
US4758426A (en) * 1987-06-11 1988-07-19 Ramsdell Bruce V Therapeutic toilet solution and method of dispersion
US4923893A (en) * 1987-12-08 1990-05-08 Shionogi & Co., Ltd. External preparation of vitamin-E
EP0533641A3 (en) * 1991-08-19 1993-06-16 Novis W. Smith Jr. Coating composition for parts
US5658559A (en) * 1992-12-16 1997-08-19 Creative Products Resource Associates, Ltd. Occlusive/semi-occlusive lotion for treatment of a skin disease or disorder
US20020099113A1 (en) * 2000-09-06 2002-07-25 Rabasco John Joseph Polymer emulsion preservation using cationic compounds
US20030180341A1 (en) * 2002-03-04 2003-09-25 Gooch Jan W. Biocompatible hydrophilic films from polymeric mini-emulsions for application to skin

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5437837A (en) * 1977-08-26 1979-03-20 Shiseido Co Ltd Makeup cosmetics
SE7713617L (sv) * 1977-12-01 1979-06-02 Astra Laekemedel Ab Antitranspirationsmedel
US4310509A (en) 1979-07-31 1982-01-12 Minnesota Mining And Manufacturing Company Pressure-sensitive adhesive having a broad spectrum antimicrobial therein
US4323557A (en) 1979-07-31 1982-04-06 Minnesota Mining & Manufacturing Company Pressure-sensitive adhesive containing iodine
FR2518404A1 (fr) * 1981-12-23 1983-06-24 Thermogene Composition analgesique comprenant au moins un phtalate acide d'alcool neutralise par une base et des extraits de tourbe
GB2133284A (en) * 1983-01-07 1984-07-25 English Grains Limited Resilient pharmaceutical unit for treating mouth ulcers
GB2134781B (en) * 1983-02-15 1986-02-12 Diomed Dev Ltd Composition for the treatment of stasis leg ulcers
US4563184A (en) * 1983-10-17 1986-01-07 Bernard Korol Synthetic resin wound dressing and method of treatment using same

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2628205A (en) * 1950-10-21 1953-02-10 Res Prod Corp Viscous hydrophilic composition and method of making the same
US2693438A (en) * 1951-02-21 1954-11-02 Norwich Pharma Co Preformed, nonadherent films for application to open lesions
US3079299A (en) * 1959-11-16 1963-02-26 Gen Aerosol Corp Self-propelling medicinal ointment composition containing polyethylene and method ofapplication
US3215599A (en) * 1963-07-02 1965-11-02 Warner Lambert Pharmaceutical Process for preparing polymer waxmodified petroleum oil unctuous base
US3485915A (en) * 1966-04-22 1969-12-23 Revlon Thickened hydroxypropyl cellulose compositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2628205A (en) * 1950-10-21 1953-02-10 Res Prod Corp Viscous hydrophilic composition and method of making the same
US2693438A (en) * 1951-02-21 1954-11-02 Norwich Pharma Co Preformed, nonadherent films for application to open lesions
US3079299A (en) * 1959-11-16 1963-02-26 Gen Aerosol Corp Self-propelling medicinal ointment composition containing polyethylene and method ofapplication
US3215599A (en) * 1963-07-02 1965-11-02 Warner Lambert Pharmaceutical Process for preparing polymer waxmodified petroleum oil unctuous base
US3485915A (en) * 1966-04-22 1969-12-23 Revlon Thickened hydroxypropyl cellulose compositions

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4102995A (en) * 1976-05-13 1978-07-25 Westwood Pharmaceuticals Inc. Tar gel formulation
US4113854A (en) * 1977-01-10 1978-09-12 Minnesota Mining And Manufacturing Company Prophylactic treatment of mastitis
US4492685A (en) * 1979-08-14 1985-01-08 Key Pharmaceuticals, Inc. Protective skin matrix
US4321252A (en) * 1979-08-14 1982-03-23 Key Pharmaceuticals, Inc. Polymeric diffusion matrix containing ester derivatives of estradiol
US4470962A (en) * 1979-08-14 1984-09-11 Key Pharmaceuticals, Inc. Polymeric diffusion matrix
WO1982000099A1 (en) * 1980-07-09 1982-01-21 Key Pharma Polymeric diffusion matrix for administration of drugs
US4482533A (en) * 1982-01-11 1984-11-13 Key Pharmaceuticals, Inc. Polymeric diffusion matrix containing propranolol
US4758426A (en) * 1987-06-11 1988-07-19 Ramsdell Bruce V Therapeutic toilet solution and method of dispersion
US4923893A (en) * 1987-12-08 1990-05-08 Shionogi & Co., Ltd. External preparation of vitamin-E
EP0533641A3 (en) * 1991-08-19 1993-06-16 Novis W. Smith Jr. Coating composition for parts
US5658559A (en) * 1992-12-16 1997-08-19 Creative Products Resource Associates, Ltd. Occlusive/semi-occlusive lotion for treatment of a skin disease or disorder
US20020099113A1 (en) * 2000-09-06 2002-07-25 Rabasco John Joseph Polymer emulsion preservation using cationic compounds
US6890969B2 (en) * 2000-09-06 2005-05-10 Air Products Polymers, L.P. Polymer emulsion preservation using cationic compounds
US20030180341A1 (en) * 2002-03-04 2003-09-25 Gooch Jan W. Biocompatible hydrophilic films from polymeric mini-emulsions for application to skin

Also Published As

Publication number Publication date
CH497897A (fr) 1970-10-31
NL6805856A (enrdf_load_stackoverflow) 1968-10-28
FR7919M (enrdf_load_stackoverflow) 1970-05-19
DE1767326A1 (de) 1971-09-02
GB1213295A (en) 1970-11-25
DK120859B (da) 1971-07-26
NO124623B (enrdf_load_stackoverflow) 1972-05-15

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Effective date: 19830124