WO2011010645A1 - フェンタニル含有外用貼付剤 - Google Patents
フェンタニル含有外用貼付剤 Download PDFInfo
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- WO2011010645A1 WO2011010645A1 PCT/JP2010/062201 JP2010062201W WO2011010645A1 WO 2011010645 A1 WO2011010645 A1 WO 2011010645A1 JP 2010062201 W JP2010062201 W JP 2010062201W WO 2011010645 A1 WO2011010645 A1 WO 2011010645A1
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- fentanyl
- weight
- adhesive layer
- resin
- patch
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—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
- A61K9/7076—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising ingredients of undetermined constitution or reaction products thereof, e.g. rosin or other plant resins
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4468—Non condensed piperidines, e.g. piperocaine having a nitrogen directly attached in position 4, e.g. clebopride, fentanyl
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
Definitions
- the external patch of the present invention relates to a fentanyl-containing external patch excellent in formulation stability, with excellent fentanyl skin permeability over a long period of time and without crystallization of active ingredients during storage.
- Fentanyl and fentanyl citrate are synthetic narcotic analgesics that have been confirmed to have an analgesic effect about 200 times that of morphine in animal experiments.
- a reservoir-type transdermal absorption-type sustained-release preparation containing fentanyl is commercially available, and the preparation can maintain a substantially effective blood concentration for 24 to 72 hours.
- the reservoir-type transdermal absorption-type sustained-release preparation has a fairly slow drug absorption after administration, and does not reach an effective blood concentration until 12 to 24 hours after the first administration, so it cannot obtain a rapid analgesic effect.
- Disadvantages the problem of leakage due to the reservoir-type preparation, and the disadvantage of extremely high irritation at the administration site due to containing ethanol.
- a fentanyl-containing patch (SIS preparation) using styrene / isoprene / styrene block copolymer (SIS) as a main base is also disclosed (Patent Document 2 and Patent Document 3), which precipitates crystals.
- SIS preparation styrene / isoprene / styrene block copolymer (SIS) as a main base is also disclosed (Patent Document 2 and Patent Document 3), which precipitates crystals.
- an object of the present invention is to provide a fentanyl-containing external patch that is excellent in skin permeability of fentanyl, can be stored for a long period of time without precipitating crystals, and satisfies the adhesive requirements.
- an adhesive base composed of a softener composed of styrene / isoprene / styrene block copolymer, tackifying resin, liquid paraffin and polybutene is active.
- an external patch containing the component fentanyl the present inventors have found that the above-mentioned problems can be solved by using a rosin resin and a terpene resin together as a tackifier resin, thereby completing the present invention.
- the present invention is a patch in which an adhesive layer is laminated on a support, and the adhesive layer comprises a styrene / isoprene / styrene block copolymer in an amount of 5 to 50% by weight based on the total amount of the adhesive layer.
- a fentanyl-containing external patch comprising 1 to 15% by weight of fentanyl as an active ingredient based on the total amount of the pressure-sensitive adhesive layer, 20 to 40% by weight of rosin resin as a tackifier resin
- the present invention relates to a fentanyl-containing external patch comprising 10 to 30% by weight of a terpene resin.
- the rosin resin is a hydrogenated rosin glycerin ester
- the blending ratio of liquid paraffin and polybutene as a softening agent in the range of 0.5: 1 to 3: 1, a balance between low irritation to the skin and solubility of the active ingredient in the preparation can be balanced.
- a patch for external use can be obtained.
- the patch for external use of the present invention adopts the above-described structure, so that the skin permeability of fentanyl is excellent, the active ingredient does not crystallize during storage, the preparation stability is excellent, and the adhesiveness requirement is satisfied. There are effects such as providing a satisfactory patch.
- Example 4 is a graph showing the results of a hairless mouse skin permeability test in in vitro in Test Example 1.
- 10 is a graph showing the results of a rabbit plasma concentration measurement test in Test Example 4.
- the blending amount of the styrene / isoprene / styrene block copolymer used in the adhesive layer of the external patch of the present invention is 5 to 50% by weight, preferably 10 to 30% by weight, based on the total amount of the adhesive layer.
- the tackifying resin is one that gives adhesiveness to the skin by mixing with a styrene / isoprene / styrene block copolymer, and its blending amount is 30 to 60% by weight, more preferably 40% by weight based on the total amount of the pressure-sensitive adhesive layer. ⁇ 55% by weight. If the blending amount of the tackifying resin is less than 30% by weight, the adhesive physical properties as an external patch are deteriorated, and if it exceeds 60% by weight, the tackiness becomes too strong and it causes physical skin irritation when peeled off from the skin. Absent. Furthermore, the tackifying resin used in the external patch of the present invention is to blend two kinds of rosin resin and terpene resin.
- rosin resin As one rosin resin, rosin ester, hydrogenated rosin, glycerin rosin ester, hydrogenated Examples thereof include rosin glycerin ester, rosin acid, and polymerized rosin, and hydrogenated rosin glycerin ester is particularly preferable.
- the rosin resin is blended in an amount of 20 to 40% by weight, more preferably 25 to 35% by weight, based on the weight of the entire pressure-sensitive adhesive layer. When the blending amount of the rosin resin is 20% by weight or less, the drug solubility is lowered, and unfavorable influence on the physical properties of the preparation such as crystallization of the main ingredient is exerted.
- the terpene resin is blended in an amount of 10 to 30% by weight, more preferably 10 to 25% by weight of the whole pressure-sensitive adhesive layer.
- the blending amount of the terpene resin is 10% by weight or less, the skin permeability of the drug is lowered.
- the amount of rosin resin is more than 4: 1, the skin permeability of the drug is lowered.
- the amount is less than 1: 1, adverse effects on the physical properties of the preparation such as crystallization of the main ingredient are exerted.
- the softening agent softens the pressure-sensitive adhesive, thereby improving the followability to the skin, adjusting the adhesive force, and reducing physical skin irritation.
- the softening agent is selected in consideration of fentanyl solubility and effects on the physical properties of the preparation, but liquid paraffin and polybutene are particularly preferable.
- the blending amount is 5 to 40% by weight, more preferably 10 to 30% by weight. If it is less than 5% by weight, the pressure-sensitive adhesive becomes hard and the adhesive strength itself increases dramatically, causing skin irritation, while the followability to the skin is deteriorated, and on the contrary, it is easily peeled off.
- the blending amount of the softener exceeds 40% by weight, the main ingredient is crystallized due to a relative decrease in the blending amount of the rosin resin, or the cohesive force of the adhesive is reduced, resulting in a decrease in the adhesive strength. This is not preferable because an adhesive residue may be generated at the application site.
- the fentanyl solubility of liquid paraffin and polybutene is polybutene> liquid paraffin, and the solubility of the active ingredient in the preparation can also be adjusted.
- the blending amount of liquid paraffin is more than 3: 1, the solubility of fentanyl in the preparation is lowered, unfavorable effects such as crystallization of the active ingredient, and the adhesion of the preparation to the skin are further lowered.
- it is less than 0.5: 1, the adhesive strength becomes too strong and the skin irritation becomes strong.
- transdermal absorption enhancers include higher fatty acid esters such as isopropyl myristate and diisopropyl adipate, higher fatty acids such as isostearic acid, oleic acid and myristic acid, sorbitan monooleate, polyoxyethylene lauryl ether, and monolauric acid.
- Surfactants such as polyethylene glycol are listed.
- An antioxidant may be added to the adhesive layer of the external patch of the present invention in order to adjust the stability of the main ingredient component.
- the antioxidant include dibutylhydroxytoluene (BHT) and ascorbic acid, but BHT is preferred.
- the blending amount of BHT blended in the present invention is 0.1 to 5% by weight, preferably 0.5 to 2% by weight.
- the components usually used when controlling the patch are appropriately selected and added to the adhesive layer of the external patch of the present invention as necessary.
- water-absorbing polymers such as polyvinyl pyrrolidone and polyvinyl pyrrolidone / vinyl acetate copolymer
- inorganic fillers such as titanium dioxide and silica can be appropriately contained.
- the blending amount of fentanyl in the pressure-sensitive adhesive layer of the external patch of the present invention is 0.1 to 15% by weight, preferably 1 to 12% by weight, more preferably 3 to 10% by weight of the whole pressure-sensitive adhesive layer.
- the thickness of the pressure-sensitive adhesive layer of the external patch of the present invention is not particularly limited, but if it becomes too thin, the adhesive strength decreases, and if it becomes too thick, the number of drugs that are not used in the plaster increases and the cost is low.
- the thickness is preferably 20 to 100 ⁇ m because it becomes high and is easily peeled off by rubbing clothes.
- the flexibility and stretchability of the support in the patch affect the followability to the skin and are greatly involved in improving the transdermal absorbability of the drug.
- the support having high flexibility and stretchability used in the patch of the present invention include low density polymer films, nonwoven fabrics, woven fabrics, etc., but polyethylene terephthalate film is desirable from the viewpoint of versatility and economy.
- the thickness of the film is preferably 0.1 to 100 ⁇ m. When applied to the skin, when the thickness is 100 ⁇ m or more, the patch cannot follow the unevenness or movement of the skin due to the rigidity of the polyethylene terephthalate film, resulting in a decrease in the skin absorbability of the drug.
- the release liner used for the external patch of the present invention is polyethylene terephthalate, polypropylene, paper or the like.
- the release liner is siliconized as necessary to optimize the peel force.
- the external patch of the present invention can be produced, for example, by the following method.
- An organic solvent such as toluene is added to the base component containing the tackifier and dissolved, and then stirred and mixed with the other components dissolved in an appropriate organic solvent.
- the obtained solution is applied on a silicon-treated release liner and dried at 90 ° C. for 10 minutes to form a 20 to 100 ⁇ m adhesive layer.
- the adhesive patch for external use of the present invention can be obtained by cutting into an appropriate size and shape.
- Comparative Examples 1-9 From the formulations described in Tables 3 and 4, external patches for each comparative example were prepared according to the above production method.
- Test Example 1 Hairless mouse skin permeability test in vitro
- an in vitro skin permeability test in hairless mice was conducted for Example 1 and Comparative Example 1.
- the back-extracted skin was set in a Franz-type cell, the inside thereof was filled with phosphate buffered saline, and warm water at 37 ° C. was refluxed in the water jacket.
- Each preparation was punched into a circle ( ⁇ 16 mm), the excised skin was affixed, the receptor fluid was sampled over time, the amount of fentanyl permeation was measured by liquid chromatography, and the permeation rate was calculated. The result is shown in FIG.
- Test Example 2 Stability test Table 5 shows the results of visual observations of the formulations of Examples 1 to 9 and Comparative Examples 1 to 8 after 2 months of storage at room temperature. Formulations with crystal precipitation are indicated by x, and preparations without crystal precipitation are indicated by ⁇ .
- Test Example 3 Adhesive strength test For Examples 1, 6 to 9 and Comparative Examples 3 to 8, the adhesive strength was evaluated by conducting a 180 ° peel test using a tensile tester (Rheometer CR500DX manufactured by Sun Scientific Co., Ltd.). The results are shown in Table 6.
- Comparative Example 1 is inferior to the present invention in the release of the active ingredient
- Comparative Examples 2, 3, 4, and 7 have a problem of crystallization of the active ingredient in the formulation
- Comparative Examples 3, 4, 5, 7 was found to have very low tack compared to the present invention.
- Comparative Examples 6 and 8 have very high adhesiveness as compared with the present invention, and there is concern about skin irritation.
- Test Example 4 Rabbit Plasma Concentration Measurement Test A fentanyl rabbit plasma concentration measurement test was conducted on Example 1 and a commercially available product (a patch in which fentanyl was mixed with an acrylic adhesive) (for each dose of fentanyl, 4.2 mg). . Each patch was applied to the back of the rabbit from which hair had been removed for 72 hours, blood was collected over time, and the concentration of fentanyl in plasma was measured by liquid chromatography / mass spectrometry (LC / MS). The result is shown in FIG. The topical patch of this example was found to be an excellent patch that has a rapid increase in fentanyl blood concentration and can maintain a high fentanyl blood concentration over a long period of time, compared to a commercially available product. did.
- LC / MS liquid chromatography / mass spectrometry
- the fentanyl-containing external patch of the present invention is excellent in skin permeability over a long period of time, has excellent formulation stability without crystallization of active ingredients during storage, and is useful as a therapeutic agent for pain such as cancer. .
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Abstract
Description
一方、主基剤にスチレン・イソプレン・スチレンブロック共重合体(SIS)を用いたフェンタニル含有貼付剤(SIS系製剤)も開示されている(特許文献2及び特許文献3)が、結晶を析出することなく長期間保存でき、かつ使用時において長時間に亘り安定的な皮膚粘着性及び主薬放出性を充足する貼付剤は見当たらない。
また軟化剤として配合される、流動パラフィンとポリブテンの配合比を0.5:1~3:1の範囲にすることにより、皮膚に対する低い刺激性と、製剤中での主薬溶解性のバランスがとれた外用貼付剤を得ることができる。
さらに本発明の外用貼付剤に用いる粘着付与樹脂はロジン系樹脂とテルペン樹脂の2種を配合することにあり、一方のロジン系樹脂としては、ロジンエステル、水添ロジン、グリセリンロジンエステル、水添ロジングリセリンエステル、ロジン酸、重合ロジンなどが挙げられるが、特に、水添ロジングリセリンエステルが好ましい。ロジン系樹脂は粘着剤層全体の重量に対して20~40重量%、より好ましくは25~35重量%の割合で配合される。ロジン系樹脂の配合量が20重量%以下の場合、薬物溶解性が低下し、主薬成分の結晶化等、製剤物性に対する好ましくない影響が出る。また40重量%以上配合された場合には薬物の皮膚透過性が低下する。
そして、テルペン樹脂は粘着剤層全体の10~30重量%、より好ましくは10~25重量%の割合で配合される。テルペン樹脂の配合量が10重量%以下であると薬物の皮膚透過性が低下し、30重量%以上配合されると主薬成分の結晶化等、製剤物性に対する好ましくない影響が出る。
また、本発明におけるロジン系樹脂とテルペン樹脂の配合比率はロジン系樹脂:テルペン樹脂=4:1~1:1の範囲であることが好ましい。より好ましくは3:1.5~3:1である。ロジン系樹脂が4:1より多いと薬物の皮膚透過性が低下し、逆に1:1より少ないと主薬成分の結晶化等、製剤物性に対する好ましくない影響が出る。
流動パラフィン及びポリブテンのフェンタニル溶解性は、ポリブテン>流動パラフィンであり、製剤中の主薬の溶解性を調節することもできる。その配合比は、好ましくは流動パラフィン:ポリブテン=0.5:1~3:1、より好ましくは1:1~2:1である。流動パラフィンの配合量が、3:1より多いと製剤中のフェンタニル溶解性が低下し、主薬の結晶化等好ましくない影響が出、さらに製剤の皮膚への接着性が低下する。また0.5:1より少ないと、粘着力が強くなりすぎ、皮膚刺激が強くなる。
本発明の外用貼付剤の粘着層には、主薬成分の安定性を調整するため抗酸化剤を添加することができる。抗酸化剤としては具体的にはジブチルヒドロキシトルエン(BHT)、アスコルビン酸等が例示されるがBHTが好ましい。本発明に配合されるBHTの配合量は0.1~5重量%であり、好ましくは0.5~2重量%配合される。
粘着付与剤を含む基剤成分にトルエン等の有機溶媒を加え溶解した後、適当な有機溶媒に溶解させた他の成分と攪拌混合する。得られた溶液をシリコン処理された剥離ライナー上に塗布し、90℃で10分間乾燥し、20~100μmの粘着層を形成する。得られた粘着層に支持体のポリエチレンテレフタレートフィルムをラミネートした後、適当な大きさと形状に切断して本発明の外用貼付剤を得ることができる。
フェンタニルの薬物放出性を検討するため、実施例1、及び比較例1につきヘアレスマウスにおけるin vitro皮膚透過性試験を行った。背部摘出皮膚をフランツ型セルにセットし、その内側にはリン酸緩衝生理食塩水を満たし、ウォータージャケットには、37℃の温水を還流した。各製剤を円状(φ16mm)に打ち抜き、摘出皮膚を貼付し、経時的にレセプター液をサンプリングし、液体クロマトグラフ法によりフェンタニル透過量を測定し、透過速度を計算した。その結果を、図1に示す。
実施例1、6~9及び比較例3~8について引っ張り試験器(レオメーターCR500DX サン科学社製)を用い、180°剥離試験を行うことにより粘着力を評価した。その結果を表6に示す。
表5~6、及び図1に示す結果より、本発明の外用貼付剤は優れた薬物放出性、安定性、および粘着力を兼ね備えた貼付剤であることが判明した。一方、比較例1は主薬の放出性において本発明より劣ること、比較例2、3、4及び7は製剤中での主薬の結晶化の問題があること、および比較例3、4、5、7は本発明と比較して粘着性が非常に低いことが判明した。また、比較例6及び8は本発明と比較して粘着性が非常に高く、皮膚刺激性が懸念されるものである。
実施例1及び市販品(アクリル粘着剤にフェンタニルを配合した貼付剤)についてフェンタニルのウサギ血漿中濃度測定試験を行った(フェンタニルの投与量各々4.2mg)。それぞれの貼付剤を除毛したウサギ背部に72時間貼付し、経時的に採血し、液体クロマトグラフィー/マススペクトル法(LC/MS)により血漿中のフェンタニル濃度を測定した。その結果を図2に示す。本実施例の外用貼付剤は、市販品と比較して、速やかにフェンタニル血中濃度が上昇し、長時間にわたって高いフェンタニル血中濃度を維持できる優れた持続性を示す貼付剤であることが判明した。
Claims (3)
- スチレン・イソプレン・スチレンブロック共重合体を粘着剤層全体の重量に対して5~50重量%、ロジン系樹脂とテルペン樹脂からなる粘着付与樹脂を粘着剤層全体の重量に対して30~60重量%、ポリブテンと流動パラフィンからなる軟化剤を粘着剤層全体の重量に対して5~40重量%配合した粘着剤層に、有効成分としてフェンタニルを配合してなるフェンタニル含有外用貼付剤。
- ロジン系樹脂の配合量が粘着剤層全体に対して20~40重量%、そしてテルペン樹脂の配合量が粘着剤層全体に対して10~30重量%である請求項1に記載のフェンタニル含有外用貼付剤。
- ロジン系樹脂が水添ロジングリセリンエステルである請求項1または2に記載のフェンタニル含有外用貼付剤。
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2010274374A AU2010274374B2 (en) | 2009-07-24 | 2010-07-21 | Fentanyl-containing adhesive preparation for external use |
KR1020117029599A KR101766495B1 (ko) | 2009-07-24 | 2010-07-21 | 펜타닐 함유 외용 첩부제 |
US13/319,169 US9375422B2 (en) | 2009-07-24 | 2010-07-21 | Fentanyl-containing adhesive preparation for external use |
CN201080030199.2A CN102470131B (zh) | 2009-07-24 | 2010-07-21 | 含有芬太尼的外用粘合剂制剂 |
NZ596398A NZ596398A (en) | 2009-07-24 | 2010-07-21 | Fentanyl-containing adhesive preparation for external use |
SG2011084902A SG176133A1 (en) | 2009-07-24 | 2010-07-21 | Fentanyl-containing adhesive preparation for external use |
JP2011523662A JP5706324B2 (ja) | 2009-07-24 | 2010-07-21 | フェンタニル含有外用貼付剤 |
EP10802265.8A EP2457570B1 (en) | 2009-07-24 | 2010-07-21 | Fentanyl-containing adhesive preparation for external use |
CA2761600A CA2761600C (en) | 2009-07-24 | 2010-07-21 | Fentanyl-containing adhesive preparation for external use |
ES10802265.8T ES2688658T3 (es) | 2009-07-24 | 2010-07-21 | Preparación adhesiva que contiene fentanilo para uso externo |
ZA2012/00568A ZA201200568B (en) | 2009-07-24 | 2012-01-24 | Fentanyl-containing adhesive preparation for external use |
US15/168,498 US10143662B2 (en) | 2009-07-24 | 2016-05-31 | Fentanyl-containing adhesive preparation for external use |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009-173135 | 2009-07-24 | ||
JP2009173135 | 2009-07-24 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
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US13/319,169 A-371-Of-International US9375422B2 (en) | 2009-07-24 | 2010-07-21 | Fentanyl-containing adhesive preparation for external use |
US15/168,498 Continuation US10143662B2 (en) | 2009-07-24 | 2016-05-31 | Fentanyl-containing adhesive preparation for external use |
Publications (1)
Publication Number | Publication Date |
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WO2011010645A1 true WO2011010645A1 (ja) | 2011-01-27 |
Family
ID=43499117
Family Applications (1)
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PCT/JP2010/062201 WO2011010645A1 (ja) | 2009-07-24 | 2010-07-21 | フェンタニル含有外用貼付剤 |
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Country | Link |
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US (2) | US9375422B2 (ja) |
EP (1) | EP2457570B1 (ja) |
JP (1) | JP5706324B2 (ja) |
KR (1) | KR101766495B1 (ja) |
CN (1) | CN102470131B (ja) |
AU (1) | AU2010274374B2 (ja) |
CA (1) | CA2761600C (ja) |
ES (1) | ES2688658T3 (ja) |
NZ (1) | NZ596398A (ja) |
SG (2) | SG10201404167QA (ja) |
TW (1) | TWI482644B (ja) |
WO (1) | WO2011010645A1 (ja) |
ZA (1) | ZA201200568B (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016196426A (ja) * | 2015-04-03 | 2016-11-24 | 帝國製薬株式会社 | フェンタニル含有貼付剤 |
JPWO2018181364A1 (ja) * | 2017-03-27 | 2020-02-06 | 日産化学株式会社 | 硬化膜形成組成物、配向材および位相差材 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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US11786455B2 (en) | 2011-05-10 | 2023-10-17 | Itochu Chemical Frontier Corporation | Non-aqueous patch |
BR122021017591B1 (pt) | 2011-05-10 | 2022-05-10 | Itochu Chemical Frontier Corporation | Uso de lidocaína para a preparação de um curativo adesivo não-aquoso para o tratamento de dor |
US9925264B2 (en) | 2011-05-10 | 2018-03-27 | Itochu Chemical Frontier Corporation | Non-aqueous patch |
CA2850024C (en) | 2011-09-27 | 2020-07-07 | Itochu Chemical Frontier Corporation | Non-aqueous patch comprising lidocaine |
CN106192481A (zh) * | 2016-08-10 | 2016-12-07 | 东至县洋湖镇希望皮具厂 | 一种皮革制品着色用染料粘合剂 |
SG11202007131UA (en) * | 2018-01-24 | 2020-08-28 | Hisamitsu Pharmaceutical Co | Patch |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003070228A1 (fr) | 2002-02-19 | 2003-08-28 | Hisamitsu Pharmaceutical Co., Inc. | Platre de type a absorption percutanee |
JP2004524336A (ja) | 2001-03-16 | 2004-08-12 | アルザ・コーポレーシヨン | フェンタニルを投与するための経皮的張り付け剤 |
JP2008273865A (ja) | 2007-04-27 | 2008-11-13 | Yuutoku Yakuhin Kogyo Kk | 外用貼付剤 |
WO2009096354A1 (ja) * | 2008-01-28 | 2009-08-06 | Teikoku Seiyaku Co., Ltd. | フェンタニル含有外用貼付剤 |
WO2009157586A1 (ja) * | 2008-06-27 | 2009-12-30 | 祐徳薬品工業株式会社 | フェンタニルまたはその塩含有経皮吸収型貼付剤 |
JP2010006761A (ja) * | 2008-06-27 | 2010-01-14 | Yutoku Yakuhin Kogyo Kk | フェンタニルまたはその塩を含有する経皮吸収型貼付剤およびその製造方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100228514B1 (ko) | 1996-09-05 | 1999-11-01 | 한승수 | 비스테로이드성 소염진통제를 활성성분으로 하는 경피흡수제제의 제조방법 |
US20080038328A1 (en) * | 2004-05-28 | 2008-02-14 | Naruhito Higo | Pasting Preparation |
CN101080219B (zh) * | 2004-12-15 | 2010-11-17 | 帝国制药株式会社 | 含依托芬那酯的外用贴剂 |
US20090074844A1 (en) * | 2005-04-28 | 2009-03-19 | Ono Pharmaceutical Co., Ltd. | Trenadermal absorption preparation |
JP4856125B2 (ja) * | 2008-06-27 | 2012-01-18 | 祐徳薬品工業株式会社 | 安定化されたフェンタニルまたはその塩含有組成物及びこれを用いた医薬製剤並びにフェンタニルまたはその塩の安定化方法 |
JP2011236379A (ja) | 2010-05-13 | 2011-11-24 | Toyo Adl Corp | 感圧式接着剤組成物及びそれを用いた積層体 |
-
2010
- 2010-07-21 CN CN201080030199.2A patent/CN102470131B/zh active Active
- 2010-07-21 ES ES10802265.8T patent/ES2688658T3/es active Active
- 2010-07-21 SG SG10201404167QA patent/SG10201404167QA/en unknown
- 2010-07-21 WO PCT/JP2010/062201 patent/WO2011010645A1/ja active Application Filing
- 2010-07-21 KR KR1020117029599A patent/KR101766495B1/ko active IP Right Grant
- 2010-07-21 US US13/319,169 patent/US9375422B2/en active Active
- 2010-07-21 EP EP10802265.8A patent/EP2457570B1/en active Active
- 2010-07-21 JP JP2011523662A patent/JP5706324B2/ja active Active
- 2010-07-21 SG SG2011084902A patent/SG176133A1/en unknown
- 2010-07-21 CA CA2761600A patent/CA2761600C/en active Active
- 2010-07-21 AU AU2010274374A patent/AU2010274374B2/en active Active
- 2010-07-21 NZ NZ596398A patent/NZ596398A/xx unknown
- 2010-07-23 TW TW099124331A patent/TWI482644B/zh active
-
2012
- 2012-01-24 ZA ZA2012/00568A patent/ZA201200568B/en unknown
-
2016
- 2016-05-31 US US15/168,498 patent/US10143662B2/en active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004524336A (ja) | 2001-03-16 | 2004-08-12 | アルザ・コーポレーシヨン | フェンタニルを投与するための経皮的張り付け剤 |
WO2003070228A1 (fr) | 2002-02-19 | 2003-08-28 | Hisamitsu Pharmaceutical Co., Inc. | Platre de type a absorption percutanee |
JP2008273865A (ja) | 2007-04-27 | 2008-11-13 | Yuutoku Yakuhin Kogyo Kk | 外用貼付剤 |
WO2009096354A1 (ja) * | 2008-01-28 | 2009-08-06 | Teikoku Seiyaku Co., Ltd. | フェンタニル含有外用貼付剤 |
WO2009157586A1 (ja) * | 2008-06-27 | 2009-12-30 | 祐徳薬品工業株式会社 | フェンタニルまたはその塩含有経皮吸収型貼付剤 |
JP2010006761A (ja) * | 2008-06-27 | 2010-01-14 | Yutoku Yakuhin Kogyo Kk | フェンタニルまたはその塩を含有する経皮吸収型貼付剤およびその製造方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP2457570A4 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016196426A (ja) * | 2015-04-03 | 2016-11-24 | 帝國製薬株式会社 | フェンタニル含有貼付剤 |
JPWO2018181364A1 (ja) * | 2017-03-27 | 2020-02-06 | 日産化学株式会社 | 硬化膜形成組成物、配向材および位相差材 |
JP7260853B2 (ja) | 2017-03-27 | 2023-04-19 | 日産化学株式会社 | 硬化膜形成組成物、配向材および位相差材 |
Also Published As
Publication number | Publication date |
---|---|
US9375422B2 (en) | 2016-06-28 |
CA2761600A1 (en) | 2011-01-27 |
US20160271075A1 (en) | 2016-09-22 |
SG10201404167QA (en) | 2014-10-30 |
EP2457570A1 (en) | 2012-05-30 |
KR101766495B1 (ko) | 2017-08-08 |
EP2457570A4 (en) | 2013-08-28 |
US10143662B2 (en) | 2018-12-04 |
CA2761600C (en) | 2017-10-24 |
AU2010274374A1 (en) | 2011-11-24 |
ES2688658T3 (es) | 2018-11-06 |
NZ596398A (en) | 2013-08-30 |
JPWO2011010645A1 (ja) | 2013-01-07 |
TWI482644B (zh) | 2015-05-01 |
KR20120035161A (ko) | 2012-04-13 |
SG176133A1 (en) | 2011-12-29 |
AU2010274374B2 (en) | 2014-08-14 |
JP5706324B2 (ja) | 2015-04-22 |
CN102470131B (zh) | 2014-02-26 |
TW201117840A (en) | 2011-06-01 |
US20120071511A1 (en) | 2012-03-22 |
EP2457570B1 (en) | 2018-08-22 |
CN102470131A (zh) | 2012-05-23 |
ZA201200568B (en) | 2012-09-26 |
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