WO1998058685A1 - Dermal adhesive plaster suitable for treating localized cutaneous affections - Google Patents

Dermal adhesive plaster suitable for treating localized cutaneous affections Download PDF

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Publication number
WO1998058685A1
WO1998058685A1 PCT/EP1998/003796 EP9803796W WO9858685A1 WO 1998058685 A1 WO1998058685 A1 WO 1998058685A1 EP 9803796 W EP9803796 W EP 9803796W WO 9858685 A1 WO9858685 A1 WO 9858685A1
Authority
WO
WIPO (PCT)
Prior art keywords
plaster according
dermal
dermal plaster
backing layer
adhesive layer
Prior art date
Application number
PCT/EP1998/003796
Other languages
English (en)
French (fr)
Inventor
Bianca Maria Bocchialini
Pier Luigi Catellani
Paolo Colombo
Patrizia Santi
Giorgio Zagnoli
Original Assignee
Laboratorio Italiano Biochimico Farmaceutico Lisapharma S.P.A.
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 Laboratorio Italiano Biochimico Farmaceutico Lisapharma S.P.A. filed Critical Laboratorio Italiano Biochimico Farmaceutico Lisapharma S.P.A.
Priority to AU86289/98A priority Critical patent/AU8628998A/en
Publication of WO1998058685A1 publication Critical patent/WO1998058685A1/en

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Classifications

    • 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
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
    • A61K9/7061—Polyacrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/18—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing inorganic materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/44—Medicaments
    • 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
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
    • A61L2300/406—Antibiotics
    • 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

  • the present invention regards a dermal adhesive plaster having high mechanical strength, flexibility, transparency and electric conductivity, for releasing, in the area of application on the skin delimited by its surface, quantities of medicament capable of having locally a pharmacological effect in the treatment of localized cutaneous affections.
  • the characteristics of mechanical strength, flexibility, transparency and electric conductivity are essential for promoting transport of the medicament into the skin following a mechanical action, such as massaging or via the use of electrical or radiant energy.
  • STATE OF THE ART The most common skin affections are those caused by bacterial infections or by the local release of irritating substances, such as histamine.
  • lesions regarding the surface of the skin may often be subject to bacterial contamination of various nature, whilst the release of histamine is linked to the presence of a cellular injury of any cause, which may range from mechanical pressure exerted by a foreign body on a given area of the body to a mere insect sting.
  • the histamine released in the skin as a result of an insect sting induces a characteristic triad of phenomena known as Lewis' reaction or triple response.
  • This response comprises the rapid formation of a patch of reddening which extends for a few millimetres around the site of the lesion due to the vasodilator effect exerted directly by the histamine on small blood vessels. Subsequently there is the formation of an area of brighter flush or flare (erythema), with irregular boundaries, which extends beyond the initial red patch and is due to axon reflexes induced by the histamine, which are also able to cause vasodilatation. Finally, there is the formation of a weal, which occupies the same area as the initial red patch and is due to the increase in permeability of the capillaries, with consequent formation of oedema.
  • the quantity of medicament available for absorption is indeterminate and not very reproducible, in particular on account of the poor control of the dose deposited on the skin and of the surface over which this dose is spread out.
  • plasters that may be applied on the skin for topical administration of medicaments has been revalued. These plasters are more precisely named dermal systems and find use in the direct and localized treatment of cutaneous affections. For this activity a more or less high accumulation of the active principle is in fact required in a limited area of the epidermis, with the attempt to limit as much as possible the passage of the active principle into the systemic circulation.
  • the Japanese patent application JP60069016 describes a plaster in which the adhesive layer contains dexamethasone esterified in position 21 together with diphenhydramine for the treatment of insect stings.
  • the adhesive polymer is an ester of (meth)acrylic acid.
  • This plaster presents the drawback that the type of solvent used for the preparation of the adhesive layer is ethyl acetate.
  • the application of a plaster containing such a solvent creates by no means indifferent problems of irritation in the area of the skin which is already inflamed owing to the presence of the insect sting.
  • the international patent application WO 93110163 describes a hydrogel material comprising an aqueous mixture containing at least one water-soluble adhesive polymer that is able to crosslink, a humectant in a concentration such as to partially inhibit this reticulation, and a reticulation promoter in concentrations such as to inhibit the inhibitory effect of the moistening substance.
  • This gel which may possibly contain bactericidal additives, and pharmacological and antibiotic agents, may contain either an electrolyte or, alternatively a therapeutic agent, among which also an antihistaminic agent. When it contains the electrolyte, this material is used in combination with a substrate that is able to conduct electricity in the preparation of electrically conductive cicatrizing bandages.
  • this hydrogel contains the electrolyte, it is used for the preparation of electrically conductive bandages, whereas when it contains the active principle alone, it is used as an adhesive layer for transdermal plasters or apparatuses for iontophoresis.
  • the subject of the present invention is a dermal plaster having high mechanical strength, flexibility, transparency and electric conductivity, comprising: a) a backing layer containing:
  • both the backing layer and the adhesive layer contain an electrolyte.
  • the plaster may in particular be used in the treatment of localized cutaneous affections that require a prompt availability of the active principle, with permanence of the same in the site of action.
  • the characteristics of mechanical strength, flexibility, transparency and electric conductivity are essential for promoting transport of the medicament into the skin following on massaging or via the use of electrical or radiant energy.
  • the application of the dermal plaster which is the subject of the present invention represents a solution to the problem of topical administration of medicament in so far as it offers the following advantages: 1. a therapeutic intervention characterized by ease of application of the adhesive plaster on the wound;
  • the high gradient of concentration that is set up at the site of the lesion, due to a precise dose of medicament deposited in contact with the site involved in the therapeutic treatment, and its maintenance over a long period of time increase both the rate of absorption and the amount of active principle absorbed by the skin (bio-availability).
  • the partial occlusion of the affected area by favouring hydration of the keratinous layer, constitutes a further factor capable of increasing absorption of the medicament.
  • passage of the medicament through the skin which under normal conditions takes place by passive transportation after a more or less prolonged period of latency, may be increased by means of an action of massaging carried out directly on the affected area but with the interposition of the plaster.
  • massaging produces relief in the case of itching, at the same time favouring a greater penetration of the medicament in conditions of protection for the lesion itself.
  • energy sources such as laser beams or electric potential on the plaster applied on the lesion enables the action of promotion of permeation to increase. For this reason, the plaster possesses characteristics of electric conductivity (electric current) and transparency (laser beams).
  • Figure 1 shows the pattern of pruritus as a function of time after application of the plaster containing 4 mg ( — ⁇ — ), 10 mg ( — • — ) of promethazine hydrochloride and placebo ( — D — ).
  • Figure 2 gives the area of the weals as a function of time after application of the plaster containing 4 mg ( ⁇ ) 10 mg (D) of promethazine hydrochloride and placebo
  • Figure 3 shows the pattern of pruritus as a function of time after application of the plaster containing 4 mg ( — A. — ), 10 mg ( — • — ) of promethazine hydrochloride, and placebo ( — D — ) following on 1 minute of ionophoresis (density of current:
  • the electrolyte used both in the adhesive layer and in the backing layer is preferably a halide of an alkaline or alkaline-earth metal; according to a particularly preferred embodiment, this halide is chosen from among sodium chloride, potassium chloride, and magnesium chloride.
  • the water-insoluble polymer that is present in the backing layer is preferably chosen from polyethylene, polypropylene, polyurethane, polyacrylate, polyethylene terephthalate, polypropylene terephthalate, and polymethacrylate.
  • the thickening agent used in the backing layer is preferably chosen from between xanthan gum and cellulose and derivatives thereof.
  • the humectant namely the substance that is able to maintain a certain degree of humidity, which is contained both in the backing layer and in the adhesive layer of the dermal plaster that is the subject of the present invention is preferably chosen from among glycerine, sorbitol, propylene glycoi, and polyethylene glycol.
  • the composition used for the preparation of the backing layer contains between 50 wt% and 99 wt%, more preferably between 80 wt% and 99 wt%, of a suspension or aqueous dispersion containing the water-insoluble polymer.
  • this aqueous suspension contains 40% of esters of polymethacrylic acid and is available on the market under the trade name Eudragit ® NE 40 D.
  • the composition used to prepare the backing layer preferably contains the electrolyte in a concentration of between 0.001 % and 5 %, by weight calculated on the total weight of the said composition.
  • the electrolyte is NaCI.
  • the thickening agent is preferably present in a concentration of between 0.005% and 5%; according to a particularly preferred embodiment, the said thickening agent is hydroxypropyl cellulose.
  • the humectant, nemely the substance that is able to maintain a certain degree of humidity is preferably contained both in the backing layer and in the adhesive layer in concentrations of between 0.01 % and 5%. According to a particularly preferred embodiment, this substance is glycerine.
  • the backing layer is obtained by spreading evenly a certain amount of the above- mentioned composition on a thermo-resistant glass plate and drying the layer obtained in an air-circulation oven for 3 hours at a temperature of 40°C. After drying, a flexible, transparent, gas-permeable and electrically conductive backing is obtained having a thickness of between 0.01 mm and 0.8 mm.
  • the second layer which performs the role of depot for the medicament and at the same time that of an adhesive, may be obtained by using a polymer chosen from among polyaminomethacrylate, polyisobutylene, silicone, polyvinyl alcohol, arabic gum, rosin, and abietic acid.
  • the composition used for the adhesive layer comprises between 5 wt% and 90 wt% of an aqueous dispersion containing in turn one of the above-mentioned adhesive polymers.
  • this aqueous dispersion contains between 20 wt% and 40 wt% of polyaminomethacrylate.
  • Such aqueous dispersions are available on the market under the trade mark PLASTOID ® E35.
  • the concentration of the electrolyte in the adhesive composition ranges from ⁇ .001 and 5% by weight calculated on the total weight of said composition.
  • the humectant namely the substance capable of maintaining a certain degree of humidity is preferably contained in the adhesive composition in concentration of between 0.01 wt% and 5 wt%, and according to a particularly preferred embodiment this substance is sorbitol.
  • a given quantity of the above-mentioned composition used for preparing the adhesive layer is spread out on the film making up the backing layer.
  • the ensemble of backing layer and adhesive layer thus obtained is put in an air- circulation oven for 1 hour at a temperature of 90°C. After being cooled to room temperature, it is removed from the glass plate and adhered to a protective liner; in this way, a sheet consisting of a protective liner, adhesive layer and backing layer is obtained, from which round plasters are cut having an area of between 0.1 cm 2 and 500 cm 2 .
  • This plaster which has thickness of between 0.03 mm and 1 mm (liner excluded) has proved to be strong, flexible, transparent and electrically conductive, where the characteristics of transparency and conductivity are indispensable for the use of physical promoters of absorption, such as laser beams and electric current.
  • the dermal plaster which is the subject of the present invention is in fact even more effective in reducing the formation of the weal and in counteracting the sensation of itching when, after it has been applied on the insect sting, a slight massaging is performed on it, or else when a direct current is applied having a density preferably of between 0.01 and 0.8 mA/cm 2 .
  • the dermal plaster which is the subject of the present invention is able to reduce the sensation of pruritus when an electric current is applied on it having a density preferably of between 0.01 and 0.8 mA/cm 2 .
  • a further object of the present invention is the transdermal plaster, which does not contain the active principle, as well as its use in reducing the sensation of pruritus in the case where electric current is applied to it.
  • the composition for the adhesive layer is water-soluble renders elimination of any residue left by the piaster easier, by facilitating its removal in areas that are particularly hairy (rinsing away instead of pulling off).
  • Such affections may include local inflammation and minor allergic reactions, such as insect stings, and infected cutaneous ulcerations.
  • a suitable medicament belonging to the classes of non-steroidal anti-inflammatory agents, such as ibuprofen, naproxen, piroxicam, ketoprofen, and acetyl salicylic acid; steroidal anti-inflammatory agents for topical use, chosen from among dexamethasone, hydrocortisone, flucinolone, clobetasol, methylprednisolone, and betamethasone; antihistaminic agents, such as promethazine, terfenadine, cetirizine, ketotifen, astemizole, loratadine, azelastine, levocabastine, fenbenzamine, tripelennamine, chloropyramine, methaphenilene, thenyldiamine, bromopyrilene, chloropyrilene, methafurilene, me
  • Example 1 The percentage composition of the backing layer, which constitutes the first layer, is the following:
  • Polymethacrylate (40% aqueous dispersion) (Eudragit NE 40 D - Rofarma S.r.l., Italy) 94.8%
  • 10 g of the dispersion according to the formula given above are spread out over 200 cm 2 of a glass plate slightly smeared with silicone oil to facilitate detachment of the film at the end of the preparation, and dried in an air- circulation oven for 1 hour at a temperature of 40°C.
  • composition of the second layer which acts as a depot for the medicament and at the same time as an adhesive, is given below according to the quantity of active principle present: 4 mg of PROMETHAZINE HYDROCHLORIDE for plaster having a surface of 4 cm 2
  • PROMETHAZINE HYDROCHLORIDE 10 mo of PROMETHAZINE HYDROCHLORIDE for plaster having a surface of 4 cm 2 Polyaminomethacrylate (Plastoid E 35 L - Rofarma S.r.l., Italy) 70%
  • Double-blind tests were carried out on 10 healthy volunteers of both sexes and aged between 25 and 30 years.
  • a small allergic reaction similar to that caused by the bite of a mosquito, was caused by using a 1% histamine solution.
  • the depositing of a given quantity of the said solution (20 microlitres) on the inner part of the forearm and the subsequent puncture using a special disposable intradermic needle caused penetration of the histamine into the more superficial layers of the dermis, giving rise to the triple response referred to previously.
  • the pictures of the weal taken by a telecamera mounted on a stereoscopic microscope, were recorded and processed using an appropriate image-processing program, in order to obtain the dimensions of the weal at preset time intervals.
  • the assessment requested from each volunteer as regarded the sensation of itching during formation of the weal revealed that the treatment with the plaster, whether the one containing 4 mg or the one containing 10 mg of promethazine, was able to cause faster disappearance of the symptom after the peak value was reached, as compared with the lesion to which the placebo had been applied.
  • Figure 1 shows the curves of the pattern of pruritus as a function of time, both after application of the plaster containing promethazine hydrochloride (4 mg and 10 mg) and after application of a plaster without any pharmacological treatment (plaster without active principle, i.e., placebo).
  • the area under the curve which represents the total amount of pruritus, was found to be 45.9 in the case of the plaster with the lower dose, 42.4 in the case of the plaster containing 10 mg, and 65.8 in the case of application of the placebo.
  • the same type of in vivo experiment was conducted massaging the skin for 1 minute after application both of the plaster containing 4 mg and of the plaster containing 10 mg of promethazine hydrochloride.
  • the results obtained ( Figure 2) revealed that the weals, after reaching an area of approximately 16 mm 2 in 15 minutes, decreased rapidly: the percentage reduction of the weal was found to be 35% in the case of the plaster containing 4 mg of medicament, whereas in the case of the plaster containing 10 mg, it was approximately 50%.
  • the assessment of the pruritus during formation of the weal revealed that treatment with the plaster, whether the one containing 4 mg of promethazine hydrochloride or the one containing 10 mg of promethazine hydrochloride, was able to cause faster disappearance of pruritus than when the skin was not massaged.
  • the area under the pruritus values-versus-time curve was 28.8 in the case of the plaster with 4 mg of promethazine, 24.1 in the case of the plaster containing 10 mg, and 39.2 in the case of application of the placebo.
  • the results obtained show that, after application of either type of medicated plaster, the amount of pruritus was reduced by approximately one half with respect to the case where no massaging was applied, this reduction being present also in the case of the placebo.

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Materials Engineering (AREA)
  • Hematology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Materials For Medical Uses (AREA)
  • Elimination Of Static Electricity (AREA)
PCT/EP1998/003796 1997-06-23 1998-06-22 Dermal adhesive plaster suitable for treating localized cutaneous affections WO1998058685A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU86289/98A AU8628998A (en) 1997-06-23 1998-06-22 Dermal adhesive plaster suitable for treating localized cutaneous affections

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT97MI001475A IT1292396B1 (it) 1997-06-23 1997-06-23 Cerotto dermico avente elevata resistenza meccanica,flessibilita' trasparenza e conducibilita' elettrica nel trattamento di affezioni
ITMI97A001475 1997-06-23

Publications (1)

Publication Number Publication Date
WO1998058685A1 true WO1998058685A1 (en) 1998-12-30

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PCT/EP1998/003796 WO1998058685A1 (en) 1997-06-23 1998-06-22 Dermal adhesive plaster suitable for treating localized cutaneous affections

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AU (1) AU8628998A (enrdf_load_stackoverflow)
IT (1) IT1292396B1 (enrdf_load_stackoverflow)
WO (1) WO1998058685A1 (enrdf_load_stackoverflow)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19918473A1 (de) * 1999-04-23 2000-11-02 Lohmann Therapie Syst Lts Verfahren und Vorrichtung zum Beschriften eines flächigen klebenden Systems aus einem Polymer, insbesondere eines transdermalen therapeutischen Systems
US6538030B2 (en) * 2000-09-20 2003-03-25 Yih-Lin Chung Treating radiation fibrosis
WO2005011797A1 (de) * 2003-08-01 2005-02-10 Lts Lohmann Therapie-Systeme Ag Verfahren und vorrichtung zur verbesserung der durchlässigkeit der menschlichen haut
WO2009006701A1 (en) * 2007-07-12 2009-01-15 Peter O'gorman Topical medicament
ITBO20100454A1 (it) * 2010-07-15 2012-01-16 Maurizio Cirulli Composto a base siliconica, particolarmente per implantologia dentale
US10010612B2 (en) 2007-05-25 2018-07-03 Indivior Uk Limited Sustained delivery formulations of risperidone compounds
US10022367B2 (en) 2014-03-10 2018-07-17 Indivior Uk Limited Sustained-release buprenorphine solutions
US10058554B2 (en) 2005-09-30 2018-08-28 Indivior Uk Limited Sustained release small molecule drug formulation
US10172849B2 (en) 2010-06-08 2019-01-08 Indivior Uk Limited Compositions comprising buprenorphine
US10198218B2 (en) 2010-06-08 2019-02-05 Indivior Uk Limited Injectable flowable composition comprising buprenorphine

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6069016A (ja) * 1983-09-27 1985-04-19 Nitto Electric Ind Co Ltd 粘着貼付製剤
EP0269246A2 (en) * 1986-10-20 1988-06-01 Yamanouchi Pharmaceutical Co. Ltd. Novel plaster structure for iontophoresis
WO1993010201A1 (en) * 1991-11-15 1993-05-27 Minnesota Mining And Manufacturing Company Pressure-sensitive poly(n-vinyl lactam) adhesive composition and method for producing and using same
WO1997006847A1 (fr) * 1994-07-02 1997-02-27 Hisamitsu Pharmaceutical Co., Inc. Structure de pansement adhesif pour iontophorese

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6069016A (ja) * 1983-09-27 1985-04-19 Nitto Electric Ind Co Ltd 粘着貼付製剤
EP0269246A2 (en) * 1986-10-20 1988-06-01 Yamanouchi Pharmaceutical Co. Ltd. Novel plaster structure for iontophoresis
WO1993010201A1 (en) * 1991-11-15 1993-05-27 Minnesota Mining And Manufacturing Company Pressure-sensitive poly(n-vinyl lactam) adhesive composition and method for producing and using same
WO1997006847A1 (fr) * 1994-07-02 1997-02-27 Hisamitsu Pharmaceutical Co., Inc. Structure de pansement adhesif pour iontophorese
EP0846473A1 (en) * 1994-07-02 1998-06-10 Hisamitsu Pharmaceutical Co. Inc. Plaster structure for iontophoresis

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 009, no. 200 (C - 298) 16 August 1985 (1985-08-16) *

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19918473A1 (de) * 1999-04-23 2000-11-02 Lohmann Therapie Syst Lts Verfahren und Vorrichtung zum Beschriften eines flächigen klebenden Systems aus einem Polymer, insbesondere eines transdermalen therapeutischen Systems
DE19918473C2 (de) * 1999-04-23 2003-10-02 Lohmann Therapie Syst Lts Verfahren und Vorrichtung zum Beschriften eines flächigen klebenden Systems aus einem dünnwandigen Polymer, in Form eines wirkstoffhaltigen Pflasters, insbesondere eines transdermalen therapeutischen Systems
US6853395B1 (en) 1999-04-23 2005-02-08 Lts Lohmann Therapie-Systeme Ag Process and device for inscription of a sheet-like adhesive system of a polymer, especially of a transdermal therapeutic system
US6538030B2 (en) * 2000-09-20 2003-03-25 Yih-Lin Chung Treating radiation fibrosis
WO2005011797A1 (de) * 2003-08-01 2005-02-10 Lts Lohmann Therapie-Systeme Ag Verfahren und vorrichtung zur verbesserung der durchlässigkeit der menschlichen haut
US7858113B2 (en) * 2003-08-01 2010-12-28 Lts Lohmann Therapie-Systeme Ag Method and device for improving the permeability of the human skin
US10058554B2 (en) 2005-09-30 2018-08-28 Indivior Uk Limited Sustained release small molecule drug formulation
US10010612B2 (en) 2007-05-25 2018-07-03 Indivior Uk Limited Sustained delivery formulations of risperidone compounds
US10376590B2 (en) 2007-05-25 2019-08-13 Indivior Uk Limited Sustained delivery formulations of risperidone compound
US11013809B2 (en) 2007-05-25 2021-05-25 Indivior Uk Limited Sustained delivery formulations of risperidone compound
US11712475B2 (en) 2007-05-25 2023-08-01 Indivior Uk Limited Sustained delivery formulations of risperidone compound
WO2009006701A1 (en) * 2007-07-12 2009-01-15 Peter O'gorman Topical medicament
US10172849B2 (en) 2010-06-08 2019-01-08 Indivior Uk Limited Compositions comprising buprenorphine
US10198218B2 (en) 2010-06-08 2019-02-05 Indivior Uk Limited Injectable flowable composition comprising buprenorphine
US10558394B2 (en) 2010-06-08 2020-02-11 Indivior Uk Limited Injectable flowable composition comprising buprenorphine
US10592168B1 (en) 2010-06-08 2020-03-17 Indivior Uk Limited Injectable flowable composition comprising buprenorphine
ITBO20100454A1 (it) * 2010-07-15 2012-01-16 Maurizio Cirulli Composto a base siliconica, particolarmente per implantologia dentale
US10022367B2 (en) 2014-03-10 2018-07-17 Indivior Uk Limited Sustained-release buprenorphine solutions
US10517864B2 (en) 2014-03-10 2019-12-31 Indivior Uk Limited Sustained-release buprenorphine solutions

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Publication number Publication date
AU8628998A (en) 1999-01-04
ITMI971475A1 (it) 1998-12-23
IT1292396B1 (it) 1999-02-08
ITMI971475A0 (enrdf_load_stackoverflow) 1997-06-23

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