WO2005046653A1 - Emplatre antiphlogistique et analgesique comprenant un compose de felbinac - Google Patents

Emplatre antiphlogistique et analgesique comprenant un compose de felbinac Download PDF

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Publication number
WO2005046653A1
WO2005046653A1 PCT/KR2004/002965 KR2004002965W WO2005046653A1 WO 2005046653 A1 WO2005046653 A1 WO 2005046653A1 KR 2004002965 W KR2004002965 W KR 2004002965W WO 2005046653 A1 WO2005046653 A1 WO 2005046653A1
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WO
WIPO (PCT)
Prior art keywords
felbinac
plaster
drug
adhesive
plaster according
Prior art date
Application number
PCT/KR2004/002965
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English (en)
Inventor
Young Kweon Choi
Hyun Suk Yu
Young Moo Lee
Seon Mook Lim
Original Assignee
Icure
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 Icure filed Critical Icure
Publication of WO2005046653A1 publication Critical patent/WO2005046653A1/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
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 

Definitions

  • the present invention relates to an anti-inflammatory plaster comprising felbinac (4-biphenyl acetic acid) as an effective ingredient.
  • Drug plaster has been introduced to the treatment of various diseases as one of TTS (Transdermal Treatment System) from long years ago.
  • the drug plaster containing various drugs such as nitroglycerin for treating angina pectoris, nicotine for abstaining from smoking, estradiol for treating various diseases caused by menopause and clonidine for lowering blood pressure has been developed and sold on the market.
  • TTS shows systemic action due to distributed active substance into the circulatory blood vessel in human body which has been already absorbed through skin.
  • NSAID Non-steroidal Anti- inflammatory Drug
  • RA rheumatic arthritis
  • NSAID has lots of limits to use in long term administration caused by severe adverse action for example, heart burn, gastritis, gastriorrhagia and the like as an anti-inflammatory drug since it inhibits the release of gastrointestinal protecting substance from gastric juice.
  • H 4-321624 discloses ant i-inflammatory patch wherein base is styrene-isoprene-styrene block copolymer and solubiliser is crotamitone, however it has several disadvantages such as the reduction of adhesive ability because of the surface extrusion of crotamitone and the difficulty in handling crotamitone.
  • PCT/W098/24423 discloses anti- inflammatory patch including styrene-isoprene-styrene block copolymer, rosin resin, plasticizer and felbinac without crotamitone, however it has also some problems such as inequitable needs in maximizing skin permeating rate and inducing stable release of the drug for the application period because of its low concentration of active ingredient in the patch, i.e., about 1 to 5 (w/w) %.
  • Korean Patent No. 2002-0079811 discloses felbinac preparation of skin permeability improved by adopting water soluble additive to hot-meIt adhesive base, however it has also limits to increase the content of felbinac.
  • the inventive patch can accomplish various advantages such as high- concentrated preparation of felbinac, drug stability, increased skin permeability and so on by adopting specific components; alkanolamine as a solubilizing agent, N-alkyl-pyrrolidone as a co-solvent, non-ionic surfactant, fatty acid, fatty acid derivative and the mixture thereof as epidermal permeation enhancer, and specific structured patch; multi-layered structure comprising primer layer consisting of rubber adhesive for preventing the reverse diffusion of drug from support and improving skin adhesive ability, which can maintain long-lasting ant i-inflammatory effect of felbinac and endow with superior stability and adhesive ability to conventional patches, and have finally completed the present invention.
  • Disclosure [Technical Problem]
  • the present invention improve the reduction of adhesive ability due to solubilizer and organic solvent, the difficulty in handling and the demerits , low skin-permeability and the reduction of adhesive ability, because of extraction of the crystal of drug when the drug is high-concentrated in the plaster not containing solubilizer.
  • the present invention provide felbinac-containing plaster having long lasting anti-inflammatory effect, superior stability and adhering force to the conventional plasters therefore.
  • [Technical Solution] o> Accordingly, it is an object of the present invention to provide novel plaster comprising felbinac (4-biphenyl acetic acid) as a NSAID anti- inflammatory agent, solubilizer, co-solvent, epidermal permeation enhancer, and pressure sensitive adhesive as a support.
  • felbinac-containing plaster comprising 1 to 25 w% felbinac (4- biphenyl acetic acid) as an active ingredient, 0.1 to 7 w% alkanolamine as a solubilizer, N-alkyl-pyrrol idone as a co-solvent, 1 to 20 w at least one epidermal permeation enhancer selected from non-ionic surfactant, fatty acid and fatty acid derivative and 30 to 90 w% pressure sensitive adhesive as a support .
  • alkanolamine may be used as a solubilizer; N-alkyl- pyrrol idone as a co-solvent; non-ionic surfactant, fatty acid, fatty acid derivative and the mixture thereof as epidermal permeation enhancer; and acrylic adhesive, water soluble adhesive, rubber adhesive and the like as a pressure sensitive adhesive.
  • felbinac in an amount rnaging from about 1 to 25 w% may be used as an active ingredient; non-ionic surfactant, fatty acid, fatty acid derivative or the mixture thereof in an amount ranging from 1 to 20 w% may be used as an epidermal permeation enhancer, pressure sensitive adhesive in an amount rainging from 30 to may be used as a support .
  • the inventive plaster according to the present invention may comprise active ingredient, solubilizer, co-solvent, epidermal permeation enhancer, pressure sensitive adhesive, and other conventionally used additives in the art.
  • the composition in the plaster may comprise felbinac as an active ingredient in an amount of from 1 to 25 w% preferably, 3 to 20 w% more preferably, in total weight of inventive composition of which weight ratio of active ingredient can provide with optimum conditions such as good skin permeability, inconstant efficacy and stability of the drug, and economic interest. If the amount of felbinac in the composition is less than 1 w%, the sufficient efficacy of drug could not exert and if more than 25 w%, various problems, for example, extraction of drug crystal, decrease of adhesive force etc may occur.
  • the alkanolamine adopted by a solubilizer in the present invention has been used as a emulsifier, stabilizer, alkaline agent etc and used to increase the solubility of insoluble drug as disclosed in prior patents (United State Patent Nos. 4,678,666 and 5,436,241; European Patent No. 0276561 (BI); Korean patent No. 10-0212961). If the used amount of the agent exceeds in the amount of active ingredient, it causes to several problems such as the decrease of skin permeability or adhesive force of preparation, yellow coloring phenomenon in the process of preparation whereas the solubility of drug in the composition is increased.
  • present invention adopts N-alkyl-pyrrol idone as a co-solvent for increasing the drug amount in the adhesive composition before spreading and appropriate amount of alkanolamine as a solubilizer for improving the solubility of insoluble felbinac in the preparation in order to obtain purposed high concentrated felbinac plaster excluding any other disadvantages such as the decrease of adhesive ability or yellow coloring phenomenon.
  • alkanolamine can increase adhesive force by acting as a plasticizer resulting in improving adhering ability to skin and accordingly improving skin permeability together with good compatibility with pressure sensitive adhesive.
  • methanolamine, ethanolamine, propanolamine, isopropylamine and other alkanolamines may be used herein in the amount of preferably, from about 0.1 to 7 w%, more preferably, 1 to 5 w% in total composition.
  • the uniformity between adhesive and felbinac is not so enough to obtain uniformed drug releasing rate whereas if the amount is more than 7 w%, the drug releasing rate may be decreased due to the interaction between alkanolamine and felbinac and the adhesive ability due to the increased amount of alkanolamine in the preparation may decrease.
  • N-alkyl-pyrrrol idone preferably, N-methyl-2-pyrrolidione may be used in the present invention as a co-solvent. N-methyl-2-pyrrol idone is easily disappeared in the drying process in spite of its good solubility for felbinac therefore it can improve skin permeability and minimize skin irritation.
  • the amount of N-alkyl-pyrrol idone ranging from 0.5 to 3 folds of the amount of felbinac can be preferably used. If the amount is less than 0.5 fold of the amount of felbinac, additional other solvent to solve felbinac is necessary and the remaining co-solvent may cause to deteriorate the physical property of plaster, i.e., adhesive force and attachment force to skin etc.
  • non-ionic surfactant such as monoglyceride, sorbitan ester, sorbitan ester oxyethylene etc, fatty acid such as oleic acid, linoleic acid, capric acid, myristic acid etc, or fatty acid derivative such as oleyl alcohol, isopropyl myristate, propylene glycol laurate, polyethylene glycol laurate etc
  • Those epidermal permeation enhancers can be use as a sole or the combination thereof in the amount ranging from 1 to 30 w%, preferably, 5 to 20 w% more preferably.
  • acrylic adhesive consisting of acrylate polymer, rubber adhesive and water soluble adhesive prepared by adding several additive i.e., adhesive resin such as oil resin, rosin resin, terpene resin etc, oil, anti-oxidants to natural or synthetic rubber
  • adhesive resin such as oil resin, rosin resin, terpene resin etc, oil, anti-oxidants to natural or synthetic rubber
  • Those pressure sensitive adhesive can be use as a sole or the combination thereof in the amount ranging from 30 to 90 w%, preferably, from 45 to 70 w more preferably. If the amount of the adhesive is less than 30 w%, the cohesive force of the preparation is collapsed resulting in unfavorable problems such as skin transfer etc and the amount of active ingredient and other components can be limited to use and the adherence power is lessened if more than 90 w%.
  • the support layer (1) for preventing from drug diffusion as a base layer, primer layer (2) located thereon for preventing from the reverse diffusion of drug and improving skin adhesive ability, drug containing layer (3) located thereon containing felbinac thereon, and release liner (4) located at the uppermost which could be released by patient's hand.
  • the support (1) is made from the materials showing good humid permeability and elasticity, which do not interact between the drug and other composition in drug layer (3).
  • the material of the support may effect on drug release.
  • Synthetic resin film such as polyethylene, polypropylene, polyester and polyurethane etc, sheet, sheet foams, woven or non-woven and their laminates thereof can be preferably used as a support (3) in the present invention.
  • Preferable thickness of the support layer ranges from 30 to 200 urn, however if the width is out of the range, the skin adhering force of patch can be worse due to the decrease of adhesive force and elasticity when the patch is applied to skin.
  • the primer layer (2) existed in inner side of the support (1) plays a role of preventing from the reverse diffusion of drug and improving skin adhesive ability and it consists of rubber adhesive prepared by adding several additive i.e., adhesive resin such as oil resin, rosin resin, terpene resin etc, oil, anti-oxidants to natural or synthetic rubber.
  • Preferable thickness of the primer layer ranges from 5 to 40 urn, however if the thickness is out of the range, it could ' not prevent from the reverse diffusion of drug sufficiently or improve skin adhesive ability resulting in preventing cohesive force of adhesive agent and lowering skin adhering ability in the end, >
  • the drug containing layer (3) consists of mainly felbinac, pressure sensitive adhesive, solubilizer, co-solvent, dispersing agent, epidermal permeation accelerator and skin irritation preventing agent or plasticizer may be added thereto if required.
  • the drug layer containing felbinac and other components consists of mono-layer or multi-layer having more than two layers having thickness of each layer ranging from 10 to 150 um, preferably, from 20 to 120 um and thickness of total layers ranging from 30 to 500 um, preferably, from 50 to 200 um.
  • the drug containing layer can be formed by mono layer or bi-layer of which component of each layer may be same or different from each other in order to form multi-layer laminated with each layers wherein the closest layer to skin could release felbinac most rapidly and the layer showing the slowest releasing velocity is positioned to be closest to primer layer (2) preferably.
  • the release liner (4) can be formed with polyester film coated with silicone or fluoride, polyethylene film or paper to be attached to drug containing layer (3).
  • the inventive felbinac-containing plaster can provide with long lasting anti-inflammatory effect, superior stability and adhering force to the conventional plasters therefore, it can be useful as an effective felbinac- containing plaster to treat and alleviate various inflammation and pain inconsistently.
  • Fig. 1 presents a sectional diagram showing one embodiment example of inventive preparation
  • Fig. 2 represents the comparison of skin permeation amount experimented in hairless mouse between the Example 1 of the present invention, comparative example and conventional plaster.
  • Comparative Example 1 Preparation of Comparative plaster (1) > 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer and 5 w% felbinac were added to 5 w% N-methyl-2-pyrrol idone used as a co- solvent and stirred to solve completely. 77 w% rubber adhesive was added thereto and stirred for 30 mins sufficiently. 3 w% triethanolamine used as a solubilizer was further added thereto and stirred for 30 mins removing air bubble.
  • the mixture was spread on a release liner in order to the mixture 2 contains 0.17 mg/cm of drug and dried at 90°C for 20 mins to remove volatile co-solvent and volatile ingredient in pressure sensitive adhesive. After the drying process, the exposed dug-containing layer was closed with already prepared support layer spread with primer layer.
  • the plaster prepared by above procedure was cut into appropriate size to prepare felbinac containing comparative plaster (1) to use as a sample in following Experimental Examples.
  • Comparative Example 2 Preparation of Comparative plaster (2) o> Comparative plaster (2) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer, 15 w% felbinac, 67 w% rubber adhesive as a pressure sensitive adhesive, 3 w% 2 triethanolamine as a solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Comparative Example 3 Preparation of Comparative plaster (3)
  • Comparative plaster (3) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer, 15 w% felbinac, 70 w acrylic adhesive as a pressure sensitive adhesive, and 0.50 2 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Example 1 Preparation of inventive plaster (1) t ⁇ > Inventive plaster (1) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer, 5 w felbinac, 77 w% acrylic adhesive as a pressure sensitive adhesive, and 0.17 2 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Example 2 Preparation of inventive plaster (2) 5> Inventive plaster (2) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer, 10 w% felbinac, 72 w% acrylic adhesive as a pressure sensitive adhesive, and 0.34 2 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Example 3 Preparation of inventive plaster (3) ⁇ -8> Inventive plaster (3) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer, 20 w% felbinac, 62 w% acrylic adhesive as a pressure sensitive adhesive, 3 w% 2 triethanolamine as a solubilizer and 0.67 mg/cm of drug content to use as a sample in following Experimental Examples. )>
  • Example 4 Preparation of inventive plaster (4)
  • Inventive plaster (4) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer, 15 w% felbinac, 67 w% acrylic adhesive as a pressure sensitive adhesive, 3 w% 2 triethanolamine as a solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Example 5 Preparation of inventive plaster (5)
  • Inventive plaster (5) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% oleic acid used as an epidermal permeation enhancer, 15 w% felbinac, 67 w% acrylic adhesive as a pressure sensitive adhesive, 3 w% triethanolamine as a 2 solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Example 6 Preparation of inventive plaster (6) > Inventive plaster (6) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% oleylalcohol used as an epidermal permeation enhancer, 15 w% felbinac, 67 w% acrylic adhesive as a pressure sensitive adhesive, 3 w% triethanolamine as a 2 solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples. > Example 7: Preparation of inventive plaster (7)
  • Inventive plaster (7) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting the mixture of 5 w% oleylalcohol and 10% monooleic acid sorbitane used as an epidermal permeation enhancer, 15 w% felbinac, 67 w% acrylic adhesive as a pressure sensitive adhesive, 3 w% triethanolamine as a solubilizer and 0.50 2 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Example 8 Preparation of inventive plaster (8) > Inventive plaster (8) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting the mixture of 15 w% monooleic acid sorbitane used as an epidermal permeation enhancer, 15 w% felbinac, 67 w% acrylic adhesive as a pressure sensitive 2 adhesive, 3 w% monoethanolamine as a solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Inventive plaster (9) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting the mixture of 15 w% monooleic acid sorbitane used as an epidermal permeation enhancer, 15 w% felbinac, 65 w% acrylic adhesive as a pressure sensitive 2 adhesive, 5 w% triethanolamine as a solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Example 10 Preparation of inventive plaster (10)
  • Inventive plaster (10) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting the mixture of 15 w% monooleic acid sorbitane used as an epidermal permeation enhancer, 15 w% felbinac, 65 w acrylic adhesive as a pressure sensitive 2 adhesive, 5 w% monoethanolamine as a solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples.
  • the inventive felbinac-containing plaster can provide with long lasting ant i-inflammatory effect, superior stability and adhering force to the conventional plasters therefore, it can be useful as an effective felbinac-containing plaster to treat and alleviate various inflammation and pain inconsistently. While the invention has been described with respect to the above specific embodiments, it should be recognized that various modification and changes might be made to the invention by those skilled in the art which also fall within the scope of the invention as defined in the appended claims.

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  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne un emplâtre contenant du felbinac, en particulier un emplâtre comprenant du felbinac (acide 4-biphényl acétique) en tant qu'agent anti-inflammatoire non stéroïdien, un agent de solubilisation, un co-solvant, un agent d'amélioration de perméabilité épidermique et un adhésif autocollant servant de support. Cet emplâtre offre un effet anti-inflammatoire de longue durée, une meilleure stabilité et un meilleur pouvoir d'adhérence que les emplâtres classiques. Il peut être utilisé comme emplâtre contenant du felbinac, efficace pour traiter et soulager diverses inflammations et douleurs.
PCT/KR2004/002965 2003-11-17 2004-11-16 Emplatre antiphlogistique et analgesique comprenant un compose de felbinac WO2005046653A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20030080978A KR100552649B1 (ko) 2003-11-17 2003-11-17 펠비낙 함유 소염진통용 플라스터
KR10-2003-0080978 2003-11-17

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WO2005046653A1 true WO2005046653A1 (fr) 2005-05-26

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006024339A2 (fr) * 2004-09-03 2006-03-09 Bouty S.P.A. Timbre multicouche a liberation commandee pour une utilisation topique
EP2098254A1 (fr) 2008-03-06 2009-09-09 Bayer MaterialScience AG Colles médicales pour la chirurgie dotées de liaisons bioactives
WO2010004784A1 (fr) 2008-07-10 2010-01-14 株式会社Ｊ－オイルミルズ Agent d'amélioration de goût pour aliments et boissons
EP1951211B1 (fr) 2005-10-24 2017-06-14 Handok Inc. Préparations transdermiques contenant des médicaments anti-inflammatoires non stéroïdiens hydrophobes
CN107847487A (zh) * 2015-07-27 2018-03-27 久光制药株式会社 含有阿塞那平的贴剂

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5505956A (en) * 1992-11-30 1996-04-09 Pacific Chemical Co., Ltd. Medicinal adhesive for percutaneous administration
JPH10114646A (ja) * 1996-10-08 1998-05-06 Toko Yakuhin Kogyo Kk 皮膚低刺激性経皮吸収貼付剤
WO1998024423A1 (fr) * 1996-12-06 1998-06-11 Hisamitsu Pharmaceutical Co., Inc. Timbre contenant du felbinac
EP1072261A2 (fr) * 1999-07-30 2001-01-31 Hisamitsu Pharmaceutical Co., Inc. Timbre contenant du felbinac
JP2002020274A (ja) * 2000-06-12 2002-01-23 San-A Seiyaku Kk 非ステロイド性消炎鎮痛剤の外用貼付剤および外用貼付薬

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5505956A (en) * 1992-11-30 1996-04-09 Pacific Chemical Co., Ltd. Medicinal adhesive for percutaneous administration
JPH10114646A (ja) * 1996-10-08 1998-05-06 Toko Yakuhin Kogyo Kk 皮膚低刺激性経皮吸収貼付剤
WO1998024423A1 (fr) * 1996-12-06 1998-06-11 Hisamitsu Pharmaceutical Co., Inc. Timbre contenant du felbinac
EP1072261A2 (fr) * 1999-07-30 2001-01-31 Hisamitsu Pharmaceutical Co., Inc. Timbre contenant du felbinac
JP2002020274A (ja) * 2000-06-12 2002-01-23 San-A Seiyaku Kk 非ステロイド性消炎鎮痛剤の外用貼付剤および外用貼付薬

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006024339A2 (fr) * 2004-09-03 2006-03-09 Bouty S.P.A. Timbre multicouche a liberation commandee pour une utilisation topique
WO2006024339A3 (fr) * 2004-09-03 2006-08-17 Bouty S P A Timbre multicouche a liberation commandee pour une utilisation topique
EP1951211B1 (fr) 2005-10-24 2017-06-14 Handok Inc. Préparations transdermiques contenant des médicaments anti-inflammatoires non stéroïdiens hydrophobes
EP1951211B2 (fr) † 2005-10-24 2020-06-24 Handok Inc. Préparations transdermiques contenant des médicaments anti-inflammatoires non stéroïdiens hydrophobes
EP2098254A1 (fr) 2008-03-06 2009-09-09 Bayer MaterialScience AG Colles médicales pour la chirurgie dotées de liaisons bioactives
WO2010004784A1 (fr) 2008-07-10 2010-01-14 株式会社Ｊ－オイルミルズ Agent d'amélioration de goût pour aliments et boissons
CN107847487A (zh) * 2015-07-27 2018-03-27 久光制药株式会社 含有阿塞那平的贴剂
US20190000775A1 (en) * 2015-07-27 2019-01-03 Hisamitsu Pharmaceutical Co., Inc. Asenapine-containing patch
EP3329915A4 (fr) * 2015-07-27 2019-03-27 Hisamitsu Pharmaceutical Co., Inc. Patch adhésif contenant de l'asénapine
TWI677352B (zh) * 2015-07-27 2019-11-21 日商久光製藥股份有限公司 含有阿申那平（ａｓｅｎａｐｉｎｅ）之貼附劑
US10806705B2 (en) 2015-07-27 2020-10-20 Hisamitsu Pharmaceutical Co., Inc. Asenapine-containing patch
CN107847487B (zh) * 2015-07-27 2021-11-02 久光制药株式会社 含有阿塞那平的贴剂

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KR100552649B1 (ko) 2006-02-20

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