WO2006080199A1 - 貼付剤 - Google Patents
貼付剤 Download PDFInfo
- Publication number
- WO2006080199A1 WO2006080199A1 PCT/JP2006/300419 JP2006300419W WO2006080199A1 WO 2006080199 A1 WO2006080199 A1 WO 2006080199A1 JP 2006300419 W JP2006300419 W JP 2006300419W WO 2006080199 A1 WO2006080199 A1 WO 2006080199A1
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- WO
- WIPO (PCT)
- Prior art keywords
- pisoprolol
- patch
- skin
- acid
- present
- Prior art date
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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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Definitions
- the present invention relates to a patch containing pisoprolol which is a ⁇ -blocker.
- Pisoprolol is a j8 blocker with high ⁇ 1 receptor selectivity and no intrinsic sympathetic nerve stimulation and membrane stabilization.
- symptoms such as bradycardia, dizziness, and malaise may occur, and there are problems in terms of stabilizing blood concentrations and sustaining effects.
- percutaneous absorption preparations are expected to have advantages such as reduction in the number of administrations, improvement in compliance, ease of administration and discontinuation, and are known to be particularly useful for elderly and pediatric patients.
- a transdermal preparation containing pisoprolol as an active ingredient a (meth) acrylic acid alkyl ester is polymerized with a monomer that can be polymerized therewith and does not contain any deviation of carboxyl group and sulfo group.
- an adhesive layer comprising an acrylic pressure-sensitive adhesive and pisoprolol or a pharmacologically acceptable salt thereof is provided on one side of a support.
- Patent Document 1 Japanese Patent Application Laid-Open No. 2003-313122
- the present inventors have applied a patch containing pisoprolol and / or a pharmaceutically acceptable salt thereof to a preparation having a specific ratio between the 24-hour value of pisoprolol skin permeation rate and the maximum value. Then, in repeated administration (preferably once a day), the onset of drug effect is fast and the fluctuation range of blood concentration is small, so that stable drug effect is obtained with few side effects and skin irritation is unlikely to occur. It was found that a patch can be provided.
- the present invention relates to a pisoprolol patch, which is 15 to 60% of the maximum value of 24-hour value skin permeation rate of pisoprolol skin permeation rate.
- the present invention also relates to the pisoprolol patch, wherein the maximum value of pisoprolol skin permeation rate is obtained within 12 hours during the administration period.
- the present invention relates to the pisoprolol patch, wherein the skin diffusion coefficient force of pisoprolol is 10E-8 to 6 ⁇ 10E-8 cm 2 / sec.
- the present invention also relates to the pisoprolol patch, characterized in that pisoprolol and / or a pharmaceutically acceptable salt thereof is contained in an amount of 1 to 40% by mass of the entire patch base.
- the present invention is characterized in that the base of the patch is composed of one or more selected from styrene-isoprene-styrene block copolymer, polyisobutylene, acrylic polymer and silicone polymer force. And the pisoprolol patch.
- the present invention relates to the pisoprolol patch, wherein the base of the patch is a mixture of an acrylic polymer and a rubber polymer.
- the fluctuation range between the maximum value and the minimum value of the blood concentration is small even in the long-term repeated administration required for the treatment of essential hypertension. Therefore, it is difficult to cause side effects, and since the blood concentration is stabilized in a short time, a safe formulation can be provided in which rapid onset of medicinal effects and less skin irritation are unlikely to occur.
- the patch refers to a patch containing at least a support and an adhesive layer composition.
- V and generally include reservoir-type external patches and matrix-type external patches. Comparing reservoir-type external patches and matrix-type external patches, matrix-type external patches, which generally have a self-adhesive adhesive layer that adheres directly to the skin, have better adhesion. Since the permeability of the drug to the skin is also excellent, the patch of the present invention will be mainly described below by taking a matrix type patch as an example, but it is not limited thereto.
- the hydrophobic polymer refers to a polymer that uses an organic solvent or a mixture of organic solvents as the polymer solvent when the adhesive layer of the patch is produced.
- the patch of the present invention typically has a drug (pisoprolol and
- the adhesive layer preferably has an adhesive force sufficient to maintain an effective area on the skin surface for at least 12 hours or longer, but if this is difficult, the area is larger than the drug-containing layer. It is also possible to use a sheet-like cover having adhesive strength.
- the Bisobu mouth roll that can be used in the present invention may be free or salt! /.
- a salt it is not particularly limited as long as it is a pharmaceutically acceptable salt, but fumarate, hydrochloride, sulfate, mesylate, citrate, tartrate, maleate, acetate Is preferred. Of these, bisoprolol hemifomarate is particularly preferable.
- the bisoboral roll that can be used in the present invention is 1 to 40% by mass, preferably 5 to 30% by mass, and more preferably, from the viewpoint of skin permeability and physical properties of the preparation, based on the whole patch base. 10 to 15% by mass is contained.
- the maximum value of the pisoprolol skin permeation rate of the patch of the present invention is the blood concentration in a short time. In order to stabilize, it is obtained within 12 hours, preferably within 10 hours, and more preferably within 8 hours during the administration period.
- the 24-hour value of pisoprolol skin permeation rate of the patch of the present invention is determined from the viewpoint of stabilizing the blood concentration in a short time in which the fluctuation range between the maximum value and the minimum value of the blood concentration is small. It is 15 to 60% of the maximum value of the speed, preferably 20 to 40%, more preferably 20 to 30%.
- pisoprolol skin permeation rate (maximum value) is determined by a human skin permeation test.
- a specific test method is to use test human skin (abdomen) cut to a thickness of about 500 m from the stratum corneum side, affix each preparation to the stratum corneum side, and the dermis side to the receptor layer side. Installed in a flow-through diffusion cell.
- the receptor layer is circulated around the outer periphery with a pH 7.4 phosphate buffered saline so that the skin surface temperature is 32 ⁇ 1 ° C.
- the skin diffusion coefficient of pisoprolol in the patch of the present invention reaches a stable blood concentration in a relatively short time after the start of administration, and the fluctuation range between the maximum value and the minimum value of the blood concentration is small.
- a safe preparation that hardly causes force and skin irritation
- 2.5 X 10E-8 to 6 X 10E-8 cm 2 / sec preferably 3 X 10E-8 to 6 X 10E-8 cm 2 / sec More preferably, it is 3 ⁇ 10 E—8 to 5 ⁇ 10E-8 cm 2 / sec.
- the skin diffusion coefficient D can be obtained by the following equation (1), where L means skin thickness and Td means lag time.
- the skin thickness L is a value obtained by actually measuring the thickness of the human skin (abdomen) subjected to the test using a micrometer or the like.
- the lag time Td refers to the intersection when the straight line portion (steady state) in the cumulative permeation amount one hour curve is extrapolated to the time axis.
- Pisoprolol base of the patch of the present invention Z Interskin distribution coefficient is from the viewpoint of transmitting pisoprolol effective for treatment without causing skin irritation to the body through the skin. 0.8 to 2.0, preferably 1.0 to 2.0, and more preferably 1.0 to 1.5.
- the base Z distribution coefficient K between skin can be obtained by the following formula (2), where D means the skin diffusion coefficient, Cv means the drug concentration in the base, and L means the skin. Means thickness,
- J means steady state skin permeation rate
- the drug concentration Cv in the base refers to the concentration actually measured by concentrating the drug concentration contained in the preparation before the start of the test.
- steady state skin permeation rate refers to the slope of the straight line portion (steady state) in the cumulative permeation amount one hour curve.
- the patch containing pisoprolol of the present invention can use rubber-based, acrylic-based, and silicone-based high molecules in the adhesive layer composition, but hydrophobic polymers are more preferable.
- an acrylic polymer and / or a rubber polymer is preferably used.
- acrylic polymer examples include monomer units represented by 2-ethylhexyl acrylate, methyl acrylate, butyl acrylate, hydroxyethyl acrylate, 2-ethylhexyl methacrylate, and the like (meth). There is no particular limitation as long as it is a polymer or copolymer containing at least one acrylate ester.
- acrylic acid / octyl octyl ester copolymer acrylic acid 2-ethylhexyl / N-bul 2 Pyrrolidone'-dimethacrylic acid 1, 6 hexane glycol copolymer, acrylic acid-2-ethylhexyl / butyl acetate copolymer, 2-ethylhexyl acrylate / vinyl acetate / acrylic acid copolymer, acrylic Acid 2-ethylhexyl methacrylate 2-ethyl hexyl methacrylate dodecyl methacrylate copolymer, methyl acrylate Acid 2-ethyl hexyl copolymer Co-resin emulsion, Adhesives such as acrylic polymers contained in acrylic resin alkanolamine liquid, Duro-Tak acrylic adhesive series (National Starch and Chemical Co., Ltd.), GELVA acrylic Adhesive series (manufactured by Monsant).
- a copolymer containing 2-ethylhexyl acrylate as the monomer unit of acrylic polymer strength is preferred.
- the copolymer is an alkyl containing a carboxyl group in the molecule.
- a copolymer containing substantially no alcoholic hydroxyl group in the molecule is most preferred as the adhesive layer base of the patch of the present invention in order to further stabilize an active substance that preferably contains lauric acid. .
- a copolymer further containing acrylic acid containing a carboxyl group in the molecule is advantageous because it can improve the adhesive force or, if necessary, can be used as a reaction point for crosslinking.
- the formulation stability of pisoprolol (or its salt) can be further improved. Although there is no alcoholic hydroxyl group, it is expected that some interaction occurs between the alcoholic hydroxyl group and pisoprolol.
- Such an acrylic polymer is not particularly limited as long as it has substantially no alcoholic hydroxyl group and has a carboxy group.
- 2-ethylhexyl acrylate 'binoleate acetate 'Atalinoleic acid copolymer Duro-Tak87-2852, Duro-Tak87-2194, Duro-Tak87-2196, Duro-Tak87-2353, Duro-Tak87-2051, Duro-Tak87-2052, Duro-Tak87-20 54, Duro-Tak87-2825, Duro-Tak87-2677 (National Starch & Chemical Co., Ltd.)
- hydroxyl groups derived from impurities may be introduced into the polymer, but such acrylic polymers do not substantially have hydroxyl groups in the molecule as long as the properties of the patch of the present invention are not impaired.
- acryl-based polymers having a carboxyl group if a small amount of a monomer having a hydroxyl group is present as an impurity in the raw material monomer or a side reaction such as thermal degradation occurs during polymerization, hydroxyl groups derived from impurities may be introduced into the polymer, but such acrylic polymers do not substantially have hydroxyl groups in the molecule as long as the properties of the patch of the present invention are not impaired.
- acryl-based polymers having a carboxyl group a carboxyl group.
- the hydrophobic polymer according to the present invention preferably further contains a rubber polymer. This is because the adhesiveness of the preparation can be controlled by further including a rubber polymer in the adhesive layer.
- the rubber polymer of the present invention includes both natural and synthetic elastic polymers. Preferred examples of such rubber polymers include styrene-isoprene-styrene block copolymers, isoprene rubber, polyisobutylene, styrene-butadiene polystyrene. Examples include ren block copolymerization, styrene butadiene rubber, and polysiloxane. Among them, styrene isoprene, a styrene block copolymer and / or polyisobutylene is preferably used from the viewpoint of drug skin permeability.
- Such a hydrophobic polymer may be used alone or in combination of two or more.
- an acrylic polymer and a rubber polymer are mixed, the drug can penetrate the skin. It is more preferable because it is a formulation that satisfies both the physical properties of the drug and the formulation.
- the blending amount based on the weight of the entire composition of these polymers is 5 to 90% by mass, preferably 10 to 70% by mass, more preferably 30 in consideration of the formation of the pressure-sensitive adhesive layer and sufficient permeability. It can be in an amount of ⁇ 70% by weight.
- the active substance when the active substance is in the form of a pharmaceutically acceptable acid addition salt, it is desired to further contain an organic acid in the adhesive layer.
- organic acid examples include aliphatic ( Mono, di, tri) carboxylic acids (eg acetic acid, propionic acid, isobutyric acid, caproic acid, capric acid, lactic acid, maleic acid, pyruvic acid, oxalic acid, succinic acid, tartaric acid, etc.), aromatic carboxylic acids ( For example, phthalic acid, salicylic acid, benzoic acid, acetyl salicylic acid, etc.), alkyl sulfonic acid (eg, methane sulfonic acid, ethane sulfonic acid, propyl sulfonic acid, butane sulfonic acid, polyoxyethylene alkyl ether sulfonic acid, etc.), alkyl sulfone Acid derivatives (eg, N-2-hydroxyethylpipe
- the absorption enhancer that can be used in the adhesive layer of the patch of the present invention may be any compound that has been conventionally recognized to promote absorption in the skin.
- fatty acids, fatty alcohols, fatty acid esters, amides, or ethers having 6 to 20 carbon chains aromatic organic acids, aromatic alcohols, aromatic organic acid esters or ethers (above saturated or unsaturated It may be either cyclic or linear branched), and also lactic acid esters, acetate esters, monoterpene compounds, sesquiterpene compounds, Azone, Azone ( Azone) derivatives, pyrothiodecane, glycerin fatty acid esters, propylene glycol fatty acid esters, sorbitan fatty acid esters (Span system) polysorbate system (Tween system), Riechiren glycol fatty acid esters, polyoxyethylene hardened castor oils (HCO type), polio Examples include xylethylene alkyl ethers, sucrose fatty acid esters, sucrose fatty
- strength prillic acid strength purine acid, caproic acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, linolenic acid, lauryl alcoholone, myristyl alcohol, Rail alcohol, isostearyl alcohol, cetyl alcohol, methyl laurate, hexyl laurate, jetyl sebacate, diethanolamide laurate, isopropyl myristate, myristyl myristate, octyldodecyl myristate, cetyl palmitate, salicylic acid, Methyl salicylate, ethylene glycol salicylate, cinnamate, methyl cinnamate, cresol, cetyl lactate, lauryl lactate, ethyl acetate, propyl acetate, gera-ol, thymol, eu
- Such an absorption promoter may be used in combination of two or more types, and the adhesive layer may be used in consideration of sufficient transparency as a patch and irritation to the skin such as redness and edema. based on the weight of the overall composition of, preferably a gesture et preferred that a 0.01 to 40 wt%, 0.05 to 3 0 mass 0/0, particularly preferably 0.1 to 20 mass 0 / 0 can be blended in an amount.
- the adhesive layer of the patch of the present invention may contain a plasticizer.
- Plasticizers that can be used include petroleum oils (eg, paraffinic process oil, naphthenic process oil, aromatic process oil, etc.), squalene, squalene, vegetable oils (eg, olive oil).
- the compounding amount based on the entire composition of the adhesive layer of such a plasticizer has sufficient permeability as a patch and sufficient cohesive strength.
- the total amount may be 1 to 70% by mass, preferably 3 to 50% by mass, and more preferably 5 to 40% by mass.
- the tackifier resin of the present invention may be used as a tackifier resin that can be desirably used to contain a tackifier resin when the adhesive force applicable for at least 12 hours is insufficient.
- rosin, glycerin ester of rosin, hydrogenated rosin, glycerin ester of hydrogenated rosin, pentaerythritol ester of rosin alicyclic saturated hydrocarbon resin (eg Alcon P-100, Arakawa Chemical Industries), Aliphatic hydrocarbon resin (for example, Quinton B170, Nippon Zeon), terpene resin (for example, Clearon P125, Yasuno Chemical), resin maleate and the like.
- glycerin ester of hydrogenated rosin, alicyclic saturated hydrocarbon resin, and terpene resin are preferable.
- the amount of such a tackifying resin based on the entire composition of the adhesive layer is preferably 1 to 70% by mass in consideration of sufficient adhesive strength as a patch and irritation to the skin upon peeling. May be 5-60% by weight, more preferably 10-50% by weight.
- an antioxidant e.g. aluminum silicate, Magnesium oxide, etc.
- caustic acid barium sulfate, calcium sulfate, calcium zincate, zinc oxide, titanium oxide and the like are desirable.
- Such antioxidants, fillers, crosslinking agents, preservatives, and ultraviolet absorbers are preferably 10% by mass or less, more preferably based on the total weight of the adhesive layer composition of the patch. Can be blended in an amount of 5% by weight or less, particularly preferably 2% by weight or less.
- the drug-containing adhesive layer having the composition as described above can also be produced by a deviation method.
- a base composition containing a drug is melted by heat, applied to a release paper or support, and then bonded to the support or release paper to obtain this agent.
- the base component containing the drug is dissolved in a solvent such as toluene, hexane, ethyl acetate, etc., spread on a release paper or support, and the solvent is removed by drying.
- the plaster thickness of the adhesive layer of the present invention is 10 to 300 m, preferably 25 to 200 m, more preferably 50 to 150 in consideration of sufficient permeability and sufficient adhesive strength as a patch. m.
- the patch of the present invention is typically a patch as shown in Fig. 6, but a stretchable or non-stretchable support can be used as the support.
- a stretchable or non-stretchable support can be used as the support.
- woven fabric, knitted fabric, non-woven fabric, polyurethane, polyester, polyvinyl acetate, polyvinyl chloride, polyethylene, polyethylene terephthalate, aluminum sheet, etc., or their composite material strength is also selected.
- the liner is not particularly limited as long as it can protect the adhesive layer until the patch is applied to the skin, and specifically, polyesters such as polyethylene terephthalate, polychlorinated butyl, polysalt vinylidene, etc. Film, laminate of fine paper and polyolefin A film etc. are mentioned. In these liners, it is preferable to apply a silicone treatment to the surface in contact with the pressure-sensitive adhesive layer, since the workability at the time of peeling off the preparation force liner is enhanced.
- the preparation area in the patch of the present invention is 1 to 60 cm 2 , preferably 1 to 40 cm 2 , more preferably 1 to 20 cm 2 in consideration of the amount of drug absorbed.
- Pisoprolol fumarate, sodium acetate, liquid paraffin, and decyl sebacate were placed in a mortar and mixed thoroughly. This mixture was mixed with 2-ethyl hexyl acrylate, “butyl acetate” acrylic acid copolymer, styrene isoprene, styrene block copolymer, and alicyclic saturated hydrocarbon resin (Arcon P-100, manufactured by Arakawa Chemical Industries). A coating solution was obtained by mixing with toluene and ethyl acetate. The mixing ratio of each component was as described above.
- Pisoprolol fumarate, sodium acetate and isopropyl myristate were placed in a mortar and mixed thoroughly. This mixture was mixed with 2-ethylhexyl acrylate “vinyl acetate” acrylic acid copolymer dissolved in heptane and ethyl acetate to obtain a coating solution. In addition, the compounding ratio of each component was as the said prescription.
- the obtained coating solution was applied onto a polyethylene terephthalate release film, and then heptane and ethyl acetate as solvents were removed by drying to form an adhesive layer having a predetermined plaster thickness. Furthermore, this adhesive layer was laminated with a support made of polyethylene terephthalate to obtain a patch of the present invention.
- Test 1 Human skin permeation test
- the preparation (5 cm 2 ) obtained in the Example or Comparative Example was applied to the stratum corneum side, and the dermis side was the receptor layer. At the side, attach to the flow-through diffusion cell.
- the receptor layer is circulated in the outer periphery using phosphate buffered saline at pH 7.4 so that the skin surface temperature is 32 ⁇ 1 ° C.
- the flow rate was 5 mL / hour, sampling was performed every 2 hours, and the receptor solution obtained at each time was accurately measured for the flow rate, and the drug concentration was measured by high performance liquid chromatography (the patch of the present invention). (See Fig.
- Comparative Example 3 rapidly decayed after the maximum skin permeation rate, and became a state where the drug hardly permeated.
- the pharmacokinetic parameters for human oral administration of pisoprolol fumarate were determined by the pharmacokinetic analysis software, WinNonlin (Scientific Consulting Inc.), using published oral data (5 mg). Using these parameters and the results of human skin permeation tests obtained in Examples 1 and 2 (Fig. 1), the transdermal absorption prediction system, SKIN-CADTM Proffe The concentration in human plasma after single administration and continuous administration was calculated using sional Edition ver. 3.0 (E-Hive Communication Co., Ltd.). The results are shown in Figs. Incidentally, formulations area, Example 1 to your, the Te 15cm 2, Example 2 in contact! /, 13cm 2 is Te, Comparative Example 1 to your! /, The Te 7 cm 2, 8 cm 2 in Comparative Example 2 In Comparative Example 3, it was 33 cm 2 . For comparison, the plasma concentration of 5 mg oral preparation was also shown.
- Comparative Examples 1 and 2 had the maximum and minimum ranges of plasma pisoprolol concentration, it took about 3 to 4 days to reach a steady state. These preparations are pisoprolol patches that require little time to develop a stable medicinal effect, although side effects are few.
- Comparative Example 3 and Comparative Example 4 oral preparation
- stable preparations with a maximum and minimum plasma pisoprolol concentration were not obtained. These preparations are not effective in the time zone around the minimum value, and are concerned about the occurrence of side effects such as bradycardia and dizziness due to excessive hypotension around the maximum value.
- Test 3 Skin irritation test
- a skin irritation test was conducted as one of the indices for evaluating the safety of the pisoprolol patch of the present invention.
- the skin pH value and the skin primary irritation index were determined by the following test methods. The results are shown below.
- the preparations (3 cm 2 ) of Examples 1 and 2 above, Comparative Example 1 and Reference Example 1 were used for the test.
- the erythema score at 1 hour and 48 hours after the application of the preparation to the back skin of Japanese white rabbits (female, 6 mice per group) after 24 hours, and peeling according to the following Draize method.
- the primary skin irritation index (Primary Irritation Index: PII) was calculated from the average value obtained by adding the edema score.
- FIG. 1 is a graph showing the human skin permeation rate when the patch of the present invention is applied.
- FIG. 2 is a graph showing changes in plasma concentration of pisoprolol when the patch of the present invention is continuously administered.
- FIG. 3 is a graph showing changes in plasma concentration of pisoprolol when the patch of the present invention is continuously administered.
- FIG. 4 is a graph showing changes in plasma concentration of pisoprolol when the patch of the present invention is continuously administered.
- FIG. 5 is a graph showing a cumulative permeation time curve for pisoprolol when the patch of the present invention is continuously administered.
- FIG. 6 is a diagram showing the structure of the patch of the present invention. Explanation of symbols
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06711700.2A EP1847264B1 (en) | 2005-01-31 | 2006-01-16 | Bisoprolol patch |
US11/814,840 US20090012181A1 (en) | 2005-01-31 | 2006-01-16 | Patch |
JP2007500459A JP5632577B2 (ja) | 2005-01-31 | 2006-01-16 | 貼付剤 |
US12/721,814 US20100227932A1 (en) | 2005-01-31 | 2010-03-11 | Patch |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005-024049 | 2005-01-31 | ||
JP2005024049 | 2005-01-31 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US81484007A Continuation | 2005-01-31 | 2007-07-26 |
Publications (1)
Publication Number | Publication Date |
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WO2006080199A1 true WO2006080199A1 (ja) | 2006-08-03 |
Family
ID=36740233
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2006/300419 WO2006080199A1 (ja) | 2005-01-31 | 2006-01-16 | 貼付剤 |
Country Status (4)
Country | Link |
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US (2) | US20090012181A1 (ja) |
EP (1) | EP1847264B1 (ja) |
JP (1) | JP5632577B2 (ja) |
WO (1) | WO2006080199A1 (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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EP1961417A1 (en) * | 2005-12-13 | 2008-08-27 | Nitto Denko Corporation | Bisoprolol-containing adhesive patch |
WO2008108424A1 (ja) | 2007-03-08 | 2008-09-12 | Nitto Denko Corporation | ビソプロロール経皮投与デバイス |
WO2009026133A2 (en) * | 2007-08-17 | 2009-02-26 | Alza Corporation | Transdermal bisoprolol delivery system |
US8808731B2 (en) | 2005-09-09 | 2014-08-19 | Nitto Denko Corporation | Adhesive pharmaceutical preparation containing bisoprolol |
JP2014527537A (ja) * | 2011-08-31 | 2014-10-16 | エルテーエス ローマン テラピー−ジステーメ アーゲー | 5−アミノレブリン酸塩酸塩用の経皮治療システム |
Families Citing this family (5)
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CA2719605C (en) * | 2008-03-25 | 2016-07-12 | Teikoku Seiyaku Co., Ltd. | Transdermally absorbable preparation |
JP5776079B2 (ja) * | 2010-02-26 | 2015-09-09 | 日東電工株式会社 | ビソプロロール含有貼付製剤 |
CN105213351B (zh) * | 2013-09-25 | 2018-03-13 | 南阳市汇博生物技术有限公司 | 用于增生性疤痕修复的贴膜 |
CN116036049A (zh) * | 2015-06-17 | 2023-05-02 | 东亚荣养株式会社 | 含有比索洛尔的贴剂 |
US9804046B2 (en) * | 2015-10-27 | 2017-10-31 | DunAn Sensing, LLC | Pressure sensor with support structure for non-silicon diaphragm |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995018603A1 (en) | 1994-01-07 | 1995-07-13 | Noven Pharmaceuticals, Inc. | Transdermal device containing polyvinylpyrrolidone as solubility enhancer |
JPH11302161A (ja) * | 1998-04-17 | 1999-11-02 | Hisamitsu Pharmaceut Co Inc | 貼付製剤 |
WO2000061120A1 (fr) * | 1999-04-13 | 2000-10-19 | Hisamitsu Pharmaceutical Co., Inc. | Préparations destinées à être absorbées par voie percutanée |
WO2002069942A1 (fr) * | 2001-03-07 | 2002-09-12 | Hisamitsu Pharmaceutical Co., Inc. | Timbre adhesif |
JP2003313122A (ja) * | 2002-04-19 | 2003-11-06 | Nitto Denko Corp | ビソプロロール含有貼付剤 |
JP2004010525A (ja) * | 2002-06-05 | 2004-01-15 | Nitto Denko Corp | 経皮吸収型製剤およびその製造方法 |
JP2004083523A (ja) | 2002-08-28 | 2004-03-18 | Hisamitsu Pharmaceut Co Inc | 貼付剤 |
EP1462121A1 (en) | 2001-10-31 | 2004-09-29 | Hisamitsu Pharmaceutical Co., Inc. | Plaster having laminated support |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60174716A (ja) * | 1984-02-21 | 1985-09-09 | Yamanouchi Pharmaceut Co Ltd | パツチ剤 |
US20040142024A1 (en) * | 1999-07-27 | 2004-07-22 | Hisamitsu Pharmaceutical Co., Inc. | Patch formulation for external use |
US20030091633A1 (en) * | 2001-11-15 | 2003-05-15 | John Kelly | Methods and compositions for use of (S)-bisoprolol |
JP4945228B2 (ja) * | 2005-12-13 | 2012-06-06 | 日東電工株式会社 | ビソプロロール含有貼付製剤 |
-
2006
- 2006-01-16 US US11/814,840 patent/US20090012181A1/en not_active Abandoned
- 2006-01-16 WO PCT/JP2006/300419 patent/WO2006080199A1/ja active Application Filing
- 2006-01-16 EP EP06711700.2A patent/EP1847264B1/en active Active
- 2006-01-16 JP JP2007500459A patent/JP5632577B2/ja active Active
-
2010
- 2010-03-11 US US12/721,814 patent/US20100227932A1/en not_active Abandoned
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995018603A1 (en) | 1994-01-07 | 1995-07-13 | Noven Pharmaceuticals, Inc. | Transdermal device containing polyvinylpyrrolidone as solubility enhancer |
JPH11302161A (ja) * | 1998-04-17 | 1999-11-02 | Hisamitsu Pharmaceut Co Inc | 貼付製剤 |
WO2000061120A1 (fr) * | 1999-04-13 | 2000-10-19 | Hisamitsu Pharmaceutical Co., Inc. | Préparations destinées à être absorbées par voie percutanée |
WO2002069942A1 (fr) * | 2001-03-07 | 2002-09-12 | Hisamitsu Pharmaceutical Co., Inc. | Timbre adhesif |
EP1462121A1 (en) | 2001-10-31 | 2004-09-29 | Hisamitsu Pharmaceutical Co., Inc. | Plaster having laminated support |
JP2003313122A (ja) * | 2002-04-19 | 2003-11-06 | Nitto Denko Corp | ビソプロロール含有貼付剤 |
JP2004010525A (ja) * | 2002-06-05 | 2004-01-15 | Nitto Denko Corp | 経皮吸収型製剤およびその製造方法 |
JP2004083523A (ja) | 2002-08-28 | 2004-03-18 | Hisamitsu Pharmaceut Co Inc | 貼付剤 |
Non-Patent Citations (1)
Title |
---|
See also references of EP1847264A4 |
Cited By (17)
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US8808731B2 (en) | 2005-09-09 | 2014-08-19 | Nitto Denko Corporation | Adhesive pharmaceutical preparation containing bisoprolol |
EP1961417A4 (en) * | 2005-12-13 | 2012-07-18 | Nitto Denko Corp | ADHESIVE STAMP CONTAINING BISOPROPOL |
EP1961417A1 (en) * | 2005-12-13 | 2008-08-27 | Nitto Denko Corporation | Bisoprolol-containing adhesive patch |
US8298572B2 (en) | 2005-12-13 | 2012-10-30 | Nitto Denko Corporation | Adhesive pharmaceutical preparation containing bisoprolol |
JP2013199486A (ja) * | 2007-03-08 | 2013-10-03 | Nitto Denko Corp | ビソプロロール経皮投与デバイス |
US20100098747A1 (en) * | 2007-03-08 | 2010-04-22 | Nitto Denko Corporation | Percutaneous administration device of bisoprolol |
JP2008247899A (ja) * | 2007-03-08 | 2008-10-16 | Nitto Denko Corp | ビソプロロール経皮投与デバイス |
TWI415636B (zh) * | 2007-03-08 | 2013-11-21 | Nitto Denko Corp | Bisoprolol transdermal device |
US8703178B2 (en) | 2007-03-08 | 2014-04-22 | Nitto Denko Corporation | Percutaneous administration device of bisoprolol |
CN103784425A (zh) * | 2007-03-08 | 2014-05-14 | 日东电工株式会社 | 比索洛尔的经皮给药装置 |
WO2008108424A1 (ja) | 2007-03-08 | 2008-09-12 | Nitto Denko Corporation | ビソプロロール経皮投与デバイス |
CN103784425B (zh) * | 2007-03-08 | 2016-08-17 | 日东电工株式会社 | 比索洛尔的经皮给药装置 |
WO2009026133A3 (en) * | 2007-08-17 | 2010-04-01 | Alza Corporation | Transdermal bisoprolol delivery system |
WO2009026133A2 (en) * | 2007-08-17 | 2009-02-26 | Alza Corporation | Transdermal bisoprolol delivery system |
JP2014527537A (ja) * | 2011-08-31 | 2014-10-16 | エルテーエス ローマン テラピー−ジステーメ アーゲー | 5−アミノレブリン酸塩酸塩用の経皮治療システム |
JP2017061489A (ja) * | 2011-08-31 | 2017-03-30 | エルテーエス ローマン テラピー−ジステーメ アーゲー | 5−アミノレブリン酸塩酸塩用の経皮治療システム |
US10307382B2 (en) | 2011-08-31 | 2019-06-04 | Photonamic Gmbh & Co. Kg | Transdermal therapeutic system for 5-aminolevulinic acid hydrochloride |
Also Published As
Publication number | Publication date |
---|---|
JPWO2006080199A1 (ja) | 2008-06-19 |
JP5632577B2 (ja) | 2014-11-26 |
EP1847264B1 (en) | 2017-05-03 |
US20090012181A1 (en) | 2009-01-08 |
EP1847264A1 (en) | 2007-10-24 |
EP1847264A4 (en) | 2012-12-12 |
US20100227932A1 (en) | 2010-09-09 |
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