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WO1998053815A1 - Dispositif d'administration transdermique de medicament destine a l'administration de tropisetron ou de granisetron - Google Patents

Dispositif d'administration transdermique de medicament destine a l'administration de tropisetron ou de granisetron Download PDF

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Publication number
WO1998053815A1
WO1998053815A1 PCT/EP1997/002842 EP9702842W WO9853815A1 WO 1998053815 A1 WO1998053815 A1 WO 1998053815A1 EP 9702842 W EP9702842 W EP 9702842W WO 9853815 A1 WO9853815 A1 WO 9853815A1
Authority
WO
WIPO (PCT)
Prior art keywords
monomers
macromer
group
delivery device
drug delivery
Prior art date
Application number
PCT/EP1997/002842
Other languages
English (en)
Inventor
Jochem Effing
Original Assignee
Minnesota Mining And Manufacturing Company
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 Minnesota Mining And Manufacturing Company filed Critical Minnesota Mining And Manufacturing Company
Priority to AU31706/97A priority Critical patent/AU3170697A/en
Priority to PCT/EP1997/002842 priority patent/WO1998053815A1/fr
Publication of WO1998053815A1 publication Critical patent/WO1998053815A1/fr

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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
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
    • 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

Definitions

  • the present invention relates to a transdermal drug delivery device for the delivery of tropisetron or granisetron.
  • Transdermal drug delivery devices are designed to deliver a therapeutically effective amount of drug across the skin of a patient.
  • Transdermal drug delivery devices typically involve a carrier (such as a liquid, gel, or solid matrix, or a pressure sensitive adhesive) into which the drug to be delivered is incorporated.
  • a carrier such as a liquid, gel, or solid matrix, or a pressure sensitive adhesive
  • Devices known to the art include reservoir type devices involving membranes that control the rate of drug release to the skin and devices involving a dispersion of the drug in a matrix such as a pressure sensitive adhesive.
  • the skin presents a substantial barrier to ingress of foreign substances into the body. It is therefore often desirable or necessary to incorporate certain materials that enhance the rate at which the drug passes through the skin.
  • Tropisetron endo-lH-Indole-3-carboxylic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
  • granisetron endo-l-Methyl-N-(9-methyl-9-aza-bicyclo[3.3.1]non-3-yl)-lH- indazole-3-carboxamide
  • drugs that are structurally very similar. Both are known to be specific serotonin (5-HT 3 ) receptor antagonists and both are known to be useful as anti-emetics and are of particular use to treat and prevent emesis during chemotherapy. In such therapy, they are typically administered by injection which is uncomfortable for a patient
  • Other known medical indications of these drugs include their use as anti-nausea treatments.
  • WO 96/8229 discloses transdermal drug delivery devices that comprise a macromer containing (meth)acrylate adhesive layer containing a drug.
  • ondansetron as an anti-emetic.
  • WO 94/07468 discloses a two-phase hydrophilic drug containing matrix for use in transdermal drug delivery patches in which one phase is a continuous hydrophobic polymer phase and the other phase is a dispersed particulate hydrated inorganic silicate in whose absorbed aqueous phase the drug is dissolved.
  • the drugs mentioned are the anti-emetics ondansetron and granisetron.
  • the present invention provides a transdermal drug delivery device comprising on a backing an adhesive layer, said adhesive layer comprising:
  • a monomers being selected from the group consisting of alkylacrylates containing 4 to 12 carbon atoms in the alkyl group and alkylmethacrylates containing 4 to 12 carbon atoms in the alkyl group and said B monomers being hydrophilic monomers copolymerizable with said A monomers, and
  • the present invention further provides a pressure sensitive skin adhesive comprising :
  • a monomers being selected from the group consisting of alkylacrylates containing 4 to 12 carbon atoms in the alkyl group and alkylmethacrylates containing 4 to 12 carbon atoms in the alkyl group and said B monomers being hydrophilic monomers copolymerizable with said A monomers, and
  • the present invention provides a transdermal drug delivery device as defined above for the treatment of emesis and/or nausea or for the prevention of emesis and/or nausea and the use of the pressure sensitive skin adhesive in the manufacture of a transdermal drug delivery device for use in the treatment or prevention of emesis or for use in the treatment or prevention of nausea.
  • the adhesive layer should include an acrylate or methacryate polymer that also includes a hydrophilic comonomer. It is believed that the latter comonomer provides the necessary solubility of the drug in the adhesive layer.
  • Hydrophilic B monomers in connection with the present invention are typically monomers that have a tendency to bind or absorb water and are preferably monomers of which a homopolymer shows a tendency to swell or dissolve in water.
  • B monomers include N-vinyl-2-pyrrolidone, vinylimidazoles, 2-hydroxyethylacrylate, mono acrylates of poly( alkyl eneoxide) alkyl ether, mono methacrylates of poly(alkyleneoxide) alkyl ether, acrylamides, methacrylamides, N-vinyl valerolactam, N-vinyl caprolactam, vinyl acetate, tetra-alkylammonium containing monomers such as (meth)acryloxyethyl trimethylammonium chloride, (meth)acryloxyethyl triethylammonium chloride, (meth)acrylamido-ethyl trimethyl ammonium chloride and aminogroup containing monomers such as dimethyl
  • the B monomer is free of nucleophilic groups, in particular those that are capable of reaction with ester functions in the copolymer. While not intending to be bound by any theory, it is believed that such nucleophilic groups might react with ester functions in the copolymer leading to cross-linking of the adhesive layer and accordingly reducing the storage stability of the transdermal drug delivery device. Presumably, such reaction would be catalysed by the drugs which are fairly strong bases. For example, tropisetron has a pK * of about 9.5.
  • the B monomer is free of nucleophilic groups selected from the group consisting of hydroxy, thiol, primary amino groups, secondary amino groups and acid groups.
  • a monomers of the copolymer in the adhesive layer are alkylacrylate or alkylmethacrylate monomers containing 4 to 12 carbon atoms in the alkyl group.
  • Examples of A monomers include n-butyl, n-pentyl, n-hexyl, cyclohexyl, isoheptyl, n-nonyl, n-decyl, isohexyl, isobornyl, 2-ethyloctyl, isooctyl, n-octyl and 2-ethylhexyl acrylates and methacrylates.
  • the copolymer may further comprise units that are derived from monomers other than A and B monomers .
  • Such monomers are preferably also free of groups containing nucleophilic groups as described above.
  • Examples of other monomers that can be copolymerised with the A and B monomers include short chain alkyl acrylates and methacrylates such as ethyl(meth)acrylate and methyl(meth)acrylate and styrene.
  • the copolymer comprises units derived from a macromer that is copolymerizable with the A and B monomers .
  • the macromer preferably has a weight average molecular weight between 5000 and 500000 as measured by GPC relative to a polystyrene standard, more preferably between 2000 and 10000 and most preferably between 5000 and 30000.
  • suitable macromers include those described in WO96/8229 and in particular include polymethylmethacrylate macromer, polymethylacrylate macromer, polystyrene macromer and polystyrene-acrylonitrile macromer.
  • Polymethymethacrylate macromers for use in this invention are commercially available under the trade designation "ELNACITE" by ICI Acrylics (e.g., ELVACITE 1010, a polymethylmethacrylate macromonomer having an inherent viscosity of 0.070-0.080, a T g of 105°C, a GPC weight average molecular weight of 7,000-10,000, a GPC number average molecular weight of 2,500-4,000, and a polydispersity of 2.5-3.0, and ELVACITE 1020, a polymethylmethacrylate macromonomer having an inherent viscosity of 0.085-0. 10, a T g of 105°C, a GPC weight average molecular weight of 12,000-15,000, a GPC number average molecular weight of 4,600-6,000, and a polydispersity of 2.5-3.0).
  • ELVACITE 1010 a polymethylmethacrylate macromonomer having an inherent viscosity of 0.070-0.080,
  • the copolymer preferably comprises between 60 and 93% by weight of units derived from A monomers and between 7 and 40% by weight of units derived from B monomers . More preferably, the copolymer comprises between 70 and 90% by weight of units derived from A monomers and between 10 and 30% by weight of units derived from B monomers .
  • units derived from macromers are preferably present in an amount between 1 and 7% by weight and more preferably in an amount between 2 and 5%.
  • the copolymer of the pressure sensitive adhesive composition of this invention can be prepared by conventional free radical polymerization of A and B monomers and optional further monomers and/or macromers.
  • the polymerization can be a solution- or emulsion polymerization and can be a thermally or photochemically initiated polymerization.
  • Useful free radical initiators include azo compounds, such as azo- bisisobutyronitrile and 4,4'-azobis(-4-cyanovaleric acid), hydroperoxides such as cumene, t- butyl and t-amyl hydroperoxide, dialkyl peroxides such as di-t-butyl and dicumylperoxide, peroxyesters such as t-butylperbenzoate and di-t-butylperoxy phtalate, diacylperoxides such as benzoyl peroxide and lauroyl peroxide.
  • azo compounds such as azo- bisisobutyronitrile and 4,4'-azobis(-4-cyanovaleric acid
  • hydroperoxides such as cumene, t- butyl and t-amyl hydroperoxide
  • dialkyl peroxides such as di-t-butyl and dicumylperoxide
  • peroxyesters such as t-butyl
  • the copolymer obtained is soluble in ethyl acetate and has an inherent viscosity in the range 0.2 dl/g to about 1.8 dl/g, more preferably 0.6 dl/g to about 1.4 dl/g.
  • the drug is preferably present in the transdermal drug delivery device as free base and is present in a "therapeutically effective amount.”
  • concentration of the drug is such that in the composition it results in a therapeutic level of drug delivered over the term that the dosage form is to be used. Such delivery is dependent on a great number of variables including, for example, the particular drug, the time period for which the individual dosage unit is to be used, and the flux rate of the drug from the system.
  • the amount of drug needed can be experimentally determined.
  • the drug is present in a device of the invention in an amount by weight of about 1 to about 25 percent, preferably about 4 to 15 percent, by weight based on the total weight of the adhesive layer.
  • the adhesive layer is substantially free of solid undissolved drug.
  • the adhesive layer can also contain agents known to accelerate the delivery of the drug through the skin. These agents have been referred to as penetration enhancers, accelerants, adjuvants, and sorption promoters, and are collectively referred to herein as "enhancers".
  • enhancers are polyhydric alcohols such as dipropylene glycol, propylene glycol, and polyethylene glycol; oils such as olive oil, squalene, and lanolin; polyethylene glycol ethers and fatty ethers such as cetyl ether and oleyl ether; fatty acid esters such as isopropyl myristate; fatty alcohols such as oleyl alcohol; urea and urea derivatives such as allantoin-; polar solvents such as dimethyldecylphosphoxide, methyloctylsulfoxide, dimethyllaurylamide, dodecylpyrrolidone, isosorbitol, dimethylacetonide, dimethylsulfoxide, de
  • examples of some particular agents include caprylic acid, eucalyptol, propanediol monolaurate, N-octyl-pyrrolidone, tocopheryl acetate, tocopheryl linoleate, propyl oleate, ethyl oleate, isopropyl palmitate, oleamide, polyoxyethylene (4) lauryl ether, polyoxyethylene (2) oleyl ether and polyoxyethylene (10) oleyl ether sold under the trademarks Brij 30, 93 and 97 by ICI Americas, Inc., and polysorbate 20 sold under the trademark Tween 20 by ICI Americas, Inc.
  • enhancers such as a mixture of caprylic acid and isopropyl myristate or a mixture ofN- octyl-pyrrolidone and isopropyl myristate.
  • Isopropyl myristate is particularly preferred in connection with this invention.
  • the amount of enhancer used is between 5% by weight and 30% by weight and more preferably between 10% by weight and 25% by weight.
  • a plasticizer or tackifying agent can be incorporated into the adhesive composition to improve the adhesive characteristics of the adhesive composition.
  • a tackifying agent is particularly useful in those embodiments in which the drug does not plasticize the polymer.
  • Suitable tackifying agents are those known in the art including : (1) aliphatic hydrocarbons; (2) mixed aliphatic and aromatic hydrocarbons; (3) aromatic hydrocarbons; (4) substituted aromatic hydrocarbons; (5) hydrogenated esters; (6) polyterpenes; and (7) hydrogenated wood resins or rosins.
  • a transdermal delivery device in accordance with the invention can be prepared by dissolving the copolymer, optionally an enhancer such as isopropyl myristate and the drug in an organic solvent (e.g., ethyl acetate) to afford a coating formulation.
  • the coating formulation can be coated using conventional methods onto a suitable release liner to provide a predetermined uniform thickness of the coating formulation.
  • Suitable release liners include conventional release liners comprising a known sheet material such as a polyester web, polyethylene web, or a polystyrene web, or a polyethylene-coated paper coated with a suitable fluoropolymer or silicone based coating.
  • a preferred release liner is SCOTCHPAKTM 1022 film (3M).
  • the adhesive coated release liner is then dried and laminated onto a backing using conventional methods.
  • the backing can be occlusive, non-occlusive or a breathable film as desired.
  • the backing is flexible such that it conforms to the skin. It can be any of the conventional materials for pressure sensitive adhesive tapes, such as polyethylene, particularly low density polyethylene, linear low density polyethylene, high density polyethylene, randomly-oriented nylon fibers, polypropylene, ethylene-vinylacetate copolymer, polyurethane, rayon and the like.
  • Backings that are layered, such as polyethylene-aluminum-polyethylene composites are also suitable.
  • the backing should be substantially non-reactive with the ingredients of the formulation. Particularly preferred backings are SCOTCHPAKTM 1 109 available from 3M and COTRANTM 9722 available
  • the transdermal delivery devices can be made in the form of an article such as a tape, a patch, a sheet, a dressing or any other form known to those skilled in the art.
  • the device will be in the form of a patch of a size suitable to deliver a preselected amount of the drug through the skin.
  • the device will have a surface area of about 10 cm 2 to about 100 cm 2 and preferably between 15 and 60 cm 2 .
  • a transdermal delivery device in accordance with this invention containing as the drug tropisetron or granisetron can be used to treat any condition capable of treatment with these drugs and in particular the treatment of emesis and nausea and/or the prevention thereof.
  • the device can be placed on the skin and allowed to remain for a time sufficient to achieve or maintain the intended therapeutic effect.
  • the time that constitutes a sufficient time can be selected by those skilled in the art with consideration of the flux rate of the device of the invention and upon the condition being treated.
  • the skin penetration data given in the examples below was obtained using the following test method.
  • a static diffusion cell (Franz-cell type) is used.
  • Hairless mouse skin female hairless mice, 3-4 weeks old) or human skin (obtained from surgery) is used.
  • the skin is mounted epidermal side up between the upper and the lower portion of the cell, which are held together by means of a ball joint clamp.
  • the portion of the cell below the mounted skin is completely filled with receptor fluid "HEPES” (N-[2-hydroxyethyl]piperazine-N'-[2-ethanesulfonic acid]) buffered Hanks balanced salt solution, pH 7.2, supplemented with 4ml of anti-biotics ( A 7292 obtained from Sigma) per liter such that the receptor fluid is in contact with the skin.
  • the receptor fluid is stirred using a magnetic stir bar.
  • the sampling port is covered except when in use.
  • the release liner is removed from a 1.55 cm 2 patch and the patch is applied to the skin and pressed to cause uniform contact with the skin and then the skin is placed across the orifice of the lower portion of the diffusion cell.
  • the diffusion cell is assembled and the lower portion is filled with receptor fluid.
  • the cell is then placed in a constant temperature (32 ⁇ 1.5°C) and humidity (45 ⁇ 10% relative humidity) chamber.
  • the receptor fluid is stirred by means of a magnetic stirrer throughout the experiment to assure a uniform sample and a reduced diffusion barrier on the dermal side of the skin.
  • the entire volume of receptor fluid is withdrawn at specified time intervals (3, 6, 12, 24, 36 and 48 hours) and immediately replaced with fresh receptor fluid.
  • the withdrawn receptor fluid is analyzed for drug content using conventional high performance liquid chromatography. The cumulative amount of drug penetrating the skin is calculated. Stability test method
  • the patches were checked for their drug content before storage and after 2 and 4 weeks storage time.
  • the drug content was determined by removing the liner from the patches and placing the remaining patch in ajar with a methanol/ethyl acetate mixture. Upon stirring over night the adhesive coating dissolved in the solvent mixture. After filtration of the solution an aliquot was taken and analysed for the drug content.
  • NVP N-vinyl-2-pyrrolidone
  • ELVACITETM polymethylmethacrylate macromer available from ICI Acrylics
  • Ethyl acetate (1.5 g) is added to the polymer solution every 30 minutes until the conversion of isooctyl acrylate to polymer reaches a minimum of 95%, typically 20-30 hours.
  • An additional charge of 2,2'-azobis-(2-methyl- butyronitrile) (0.1 g) premixed with ethyl acetate is added after 5 hours and 9 hours reaction time.
  • the inherent viscosity in ethylacetate is measured by conventional means using a Canon-Fenske #50 viscosimeter in a water bath controlled at 27°C to measure the flow time of 10 millimeters of the polymer solution. The test procedure and apparatus are described in detail in rougeTextbook of Polymer Science", F.W. Billmeyer, Wiley Interscience, Second Edition, 1971, pages 84 and 85.
  • the inherent viscosity was 1.62 dl/g.
  • a flask equipped with an agitator, condensor, nitrogen inlet tube and an addition funnel is charged with isooctyl acrylate (134.75 g), N-vinylpyrrolidone (35.0 g) and ElvaciteTM 1020 (5.25 g) premixed in a mixture of ethylacetate (236.25 g) and methanol (26.25 g).
  • the mixture is heated to 60°C with medium agitation and purged with nitrogen to remove oxygen.
  • 2,2 ' -Azobis-(2-methyl-butyronitrile) (0.26 g, WakoTM V-59) is added to initiate reaction.
  • the reaction temperature is maintained at 57°C and the reaction is run for about 24 hours. After termination of the reaction additional ethyl acetate (90 g) and methanol (10 g) are added.
  • the inherent viscosity in ethyl acetate is measured by conventional means using a Canon- Fenske #50 viscosimeter in a water bath controlled at 27°C to measure the flow time of 10 millimeters of the polymer solution.
  • the test procedure and apparatus are described in detail in rougeTextbook of Polymer Science", F.W. Billmeyer, Wiley Interscience, Second Edition, 1971, pages 84 and 85.
  • the inherent viscosity was 1.4 dl/g.
  • Samples of this device with a size of 1.55 cm 2 were tested with respect to the drug release/penetration characteristics through hairless mouse skin (HMS) and human cadaver skin (HCS).
  • the cumulative amounts released after 24 hours were 303 ⁇ g/cm 2 via HMS and 308 ⁇ g/cm 2 via HCS. This corresponds to 57.2% and 58.1%) of the initial drug loading, respectively.
  • Stability testing of the formulations revealed chemical stability at 25 and 40°C for at least 4 weeks.
  • the coating solution was coated onto a release liner (SCOTCHPAKTM 1022) at a wet thickness of 600 ⁇ m and oven dried for 20 minutes at 60°C. The dried coating was then laminated with a backing (SCOTCHPAKTM 1109).
  • the resulting device had a drug loading of 6.3 mg tropisetron per 10 cm 2 . Samples of this device with a size of 1.55 cm 2 were tested with respect to the drug release/penetration characteristics through hairless mouse skin (HMS) . The cumulative amount released after 24 hours was 373.57 ⁇ g/cm 2 via HMS. This corresponds to 59.3% of the initial drug loading.
  • Stability testing of this formulation revealed a crosslinking of the drug-in-adhesive matrix and a decrease in the drug content of more than 10% within 4 weeks of storage.

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Abstract

L'invention concerne un dispositif d'administration transdermique de médicament comprenant sur le revers une couche adhésive contenant: (a) un copolymère d'un ou de plusieurs monomères A et d'un ou de plusieurs monomères B, les monomères A étant sélectionnés dans le groupe formé par des alkylacrylates contenant 4 à 12 atomes de carbone dans le groupe alkyle et des alkylméthacrylates contenant 4 à 12 atomes de carbone dans le groupe alkyle, et les monomères B étant des monomères hydrophiles pouvant être copolymérisés avec les monomères A, et (b) une quantité efficace sur le plan thérapeutique d'un médicament sélectionné dans le groupe formé par le Tropisetron et le Granisetron. Le dispositif d'administration transdermique de médicament est indiqué pour le traitement de vomissements et/ou de nausées ou la prévention de vomissements et/ou de nausées. L'invention concerne également des adhésifs cutanés autocollants, contenant du Tropisetron ou du Granisetron.
PCT/EP1997/002842 1997-05-30 1997-05-30 Dispositif d'administration transdermique de medicament destine a l'administration de tropisetron ou de granisetron WO1998053815A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU31706/97A AU3170697A (en) 1997-05-30 1997-05-30 Transdermal drug delivery device for the delivery of tropisetron or granisetron
PCT/EP1997/002842 WO1998053815A1 (fr) 1997-05-30 1997-05-30 Dispositif d'administration transdermique de medicament destine a l'administration de tropisetron ou de granisetron

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP1997/002842 WO1998053815A1 (fr) 1997-05-30 1997-05-30 Dispositif d'administration transdermique de medicament destine a l'administration de tropisetron ou de granisetron

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WO1998053815A1 true WO1998053815A1 (fr) 1998-12-03

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000047208A1 (fr) * 1999-02-09 2000-08-17 Samyang Corporation Composition transdermique d'un agent antiemetique et preparation contenant cette composition
WO2003013482A1 (fr) * 2001-08-03 2003-02-20 Strakan Group Limited Administration transdermique d'antagonistes de 5-ht3
WO2003100091A1 (fr) * 2002-05-24 2003-12-04 Epidauros Biotechnologie Ag Moyens et methodes de traitement ameliores utilisant des 'setrones'
WO2004069141A3 (fr) * 2003-02-05 2004-10-07 Strakan Ltd Granisetron transdermique
WO2006037116A2 (fr) 2004-09-28 2006-04-06 A.P. Pharma, Inc. Vehicule d'administration semi-solide et compositions pharmaceutiques
JP2008511663A (ja) * 2004-09-01 2008-04-17 ネクスメツド・ホールデイングス・インコーポレイテツド 経皮制吐送達系、そのための方法および組成物
US7395111B2 (en) 2002-10-31 2008-07-01 Transpharma Medical Ltd. Transdermal delivery system for water insoluble drugs
US7393857B2 (en) * 1999-02-18 2008-07-01 Novasearch Ag Use of 5-HT3 receptor antagonists for treating musculoskeletal diseases
US7415306B2 (en) 2002-10-31 2008-08-19 Transpharma Medical Ltd. Transdermal delivery system for anti-emetic medication
WO2009088142A1 (fr) * 2008-01-09 2009-07-16 Echo Pacific Ltd. Système d'administration transdermique de médicament contenant du granisétron
US8246981B2 (en) 2005-05-18 2012-08-21 Abeille Pharamaceuticals, Inc. Transdermal method and patch for emesis
CN101180018B (zh) * 2005-05-18 2014-02-26 亚贝丽制药公司 用于治疗恶心的经皮的方法和贴片

Citations (4)

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WO1992019226A1 (fr) * 1991-05-07 1992-11-12 Dynagen, Inc. Systeme d'administration de medicaments a liberation prolongee et controllee pour le traitement des toxicomanies
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US9913910B2 (en) 2000-05-11 2018-03-13 Heron Therapeutics, Inc. Methods of treating nausea utilizing semi-solid delivery vehicle compositions comprising granisetron
WO2003013482A1 (fr) * 2001-08-03 2003-02-20 Strakan Group Limited Administration transdermique d'antagonistes de 5-ht3
WO2003100091A1 (fr) * 2002-05-24 2003-12-04 Epidauros Biotechnologie Ag Moyens et methodes de traitement ameliores utilisant des 'setrones'
US7415306B2 (en) 2002-10-31 2008-08-19 Transpharma Medical Ltd. Transdermal delivery system for anti-emetic medication
EP1556135A4 (fr) * 2002-10-31 2011-03-30 Transpharma Medical Ltd Systeme d'administration transdermique pour medication antiemetique
US7395111B2 (en) 2002-10-31 2008-07-01 Transpharma Medical Ltd. Transdermal delivery system for water insoluble drugs
US20100008974A1 (en) * 2003-02-05 2010-01-14 Strakan International Limited Transdermal granisetron
NO331441B1 (no) * 2003-02-05 2012-01-02 Strakan Int Ltd Transdermal granistetron
RU2355387C2 (ru) * 2003-02-05 2009-05-20 Стрэкэн Интернэшнл Лимитед Трансдермальный гранисетрон
WO2004069141A3 (fr) * 2003-02-05 2004-10-07 Strakan Ltd Granisetron transdermique
US7608282B2 (en) 2003-02-05 2009-10-27 Strakan International Limited Transdermal granisetron
AU2004210181B2 (en) * 2003-02-05 2009-11-19 Kyowa Kirin Services Ltd Transdermal granisetron
HRP20050695B1 (hr) * 2003-02-05 2013-11-08 Strakan International Limited Transdermalni granisetron
US20120258164A1 (en) * 2003-02-05 2012-10-11 Strakan International Limited Transdermal granisetron
CN102526043A (zh) * 2003-02-05 2012-07-04 思特肯国际有限公司 透皮格拉司琼
KR100893158B1 (ko) * 2003-02-05 2009-04-16 스트라칸 인터네셔널 리미티드 경피성 그라니세트론
EP1784150A4 (fr) * 2004-09-01 2011-05-11 Nexmed Holdings Inc Systeme d'administration transdermique d'une composition antiemetique
JP2008511663A (ja) * 2004-09-01 2008-04-17 ネクスメツド・ホールデイングス・インコーポレイテツド 経皮制吐送達系、そのための方法および組成物
WO2006037116A2 (fr) 2004-09-28 2006-04-06 A.P. Pharma, Inc. Vehicule d'administration semi-solide et compositions pharmaceutiques
US8715710B2 (en) 2004-09-28 2014-05-06 Heron Therapeutics, Inc. Semi-solid delivery vehicle and pharmaceutical compositions for delivery of granisetron
EP1796629B1 (fr) * 2004-09-28 2014-11-12 Heron Therapeutics, Inc. Vehicule d'administration semi-solide et compositions pharmaceutiques
US10357570B2 (en) 2004-09-28 2019-07-23 Heron Therapeutics, Inc. Methods of treating nausea utilizing semi-solid delivery vehicle compositions comprising granisetron
US8246981B2 (en) 2005-05-18 2012-08-21 Abeille Pharamaceuticals, Inc. Transdermal method and patch for emesis
CN101180018B (zh) * 2005-05-18 2014-02-26 亚贝丽制药公司 用于治疗恶心的经皮的方法和贴片
US9066886B2 (en) 2008-01-09 2015-06-30 Taho Pharmaceuticals, Ltd. Transdermal drug delivery system containing granisetron
WO2009088142A1 (fr) * 2008-01-09 2009-07-16 Echo Pacific Ltd. Système d'administration transdermique de médicament contenant du granisétron

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