WO2005046654A1 - Emplatre antiphlogistique et analgesique comprenant un compose piroxicam - Google Patents

Emplatre antiphlogistique et analgesique comprenant un compose piroxicam Download PDF

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Publication number
WO2005046654A1
WO2005046654A1 PCT/KR2004/002966 KR2004002966W WO2005046654A1 WO 2005046654 A1 WO2005046654 A1 WO 2005046654A1 KR 2004002966 W KR2004002966 W KR 2004002966W WO 2005046654 A1 WO2005046654 A1 WO 2005046654A1
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WIPO (PCT)
Prior art keywords
piroxicam
plaster
drug
composition according
adhesive
Prior art date
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PCT/KR2004/002966
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English (en)
Inventor
Young Kweon Choi
Hyun Suk Yu
Young Moo Lee
Seon Mook Lim
Original Assignee
Icure
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Publication of WO2005046654A1 publication Critical patent/WO2005046654A1/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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam

Definitions

  • 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 already absorbed through skin.
  • Piroxicam one of NSAID (Non-steroidal Ant i-inflammatory Drug) has been used in treating or alleviating various inflammation diseases such as rheumatic arthritis (RA), back pain, myalgia etc till now.
  • NSAID Non-steroidal Ant i-inflammatory Drug
  • RA rheumatic arthritis
  • it has been known NSAID has lots of limits to use in long term or over-dosing oral administration caused by severe adverse action for example, hepatic disorder or gastric disorder together with other problems such as lower bio- availability in oral administration requiring over dosing because of its hepatic first-pass effect, inconvenience of injectable administration have forced to develop topical preparation such as gel, liquid, cataplasm, plaster and the like till now.
  • 92-27130 discloses a method for enhancing the skin permeability using by alcohol, amine, glyceride etc;
  • United States Patent No. 4,678,666 disclose piroxicam containing gel and ointment using organic amine as a solubilizer however, since the amount of used organic amine, i.e., 2 to 3 w%, is too higher comparing with that of piroxicam, i.e., 0.3 to 3 w%, the skin permeation force of piroxicam in the preparation is significantly decreased; United States Patent Nos.
  • 5,496,819 and 5,676,970 disclose a plaster comprising various surfactants such as triacetin or triethylcitrate, ethyleneoxide, and polyethylene non-ionic surfactant, however, there has no disclosure on the method of increasing the concentration of piroxicam to enhance skin permeation rate, and the patent suggests and disclose 0.25 w% piroxicam therein;
  • Korean Patent No. 97-73591 discloses a method for enhancing the skin permeation rate and the solubility of piroxicam using high molecular electrolyte and accelerator, however, it has limits to improve the inconvenience in administration such as transfer of drug to clothes and to solve the difficulty in qualitative administration because its limited disclosure on just a semi-solid preparation; United States Patent No.
  • 5,436,241 discloses tetrahydroxypropylethylenediamine as a drug solubilizer, however, it is also limited to gel preparation;
  • Korean .Patent No. 10-212961 discloses alkanolamine as an absorption adjuvant, however, the plaster is not suitable to use since the amount of used alkanolamine, i.e., 9 to 40 w%, is too higher comparing with that of piroxicam, i.e., 0.5 to 25 w% too;
  • the prior arts mainly related to a method of using strong organic solvent, high molecular electrolyte and alkaline substance such as organic amine and a method of enhancing the solubility of piroxicam using by harsh condition for example, mixing at high temperature in the process for preparing adhesive substance.
  • organic acid or additive which can dissolve piroxicam remains too much in the preparation, they also give rise to several problems, for example, it cause to decreased skin permeability of drug and the decrease of skin adhering force due to its decreased adhesive force of the preparation resulting from remaining excessive organic acid or additives.
  • the inventors of the present invention have intensively investigated to improve and overcome the problems of conventional patch comprising piroxicam till now.
  • the inventive patch can accomplish various advantages such as improved drug solubility, drug stability, increased skin permeability and so on by adopting specific components; alkanolamide as a solubilizer, N-alkyl-pyrrolidone as a co-solvent, sole or combination of non-ionic surfactant, fatty acid, fatty acid derivative as epidermal permeation enhancer, polyvinylpyrrolidone as a dispersion agent 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 piroxicam and endow with superior stability and adhesive ability to conventional patches, and have finally completed the present invention.
  • alkanolamide as a solubilizer
  • N-alkyl-pyrrolidone as a co-solvent
  • sole or combination of non-ionic surfactant fatty acid, fatty acid derivative as epidermal permeation enhancer
  • the present invention improve the reduction of adhesive ability due to the existing solubilizer and organic solvent, the difficulty in handling, low skin-permeability and the reduction of adhesive ability.
  • the present invention manufacture piroxicam-contaning plaster comprising the specific solubilizer, co-solvent, dispersion agent and epidermal permeation enhancer at a fixed ratio and provide an effective piroxicam-containing plaster maintaining long-lasting ant i-inflammatory effect and endowing with superior stability, skin-permeability, and adhesive- ability to conventional patches.
  • piroxicam-containing plaster composition comprising 1 to 25 w% piroxicam as an active ingredient, 1 to 35 w% alkanola ide as a solubilizer, N-alkyl-pyrrolidone as a co-solvent, 1 to 30 w% at least one epidermal permeation enhancer selected from non-ionic surfactant, fatty acid and fatty acid derivative, 1 to 30 w at least one dispersing agent selected from polyvinylpyrrolidone and cellulose derivative derivative, and 30 to 90 w% pressure sensitive adhesive as a support.
  • alkanolamide may be used as a solubilizer; N-alkyl- pyrrolidone 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.
  • piroxicam in an amount rangingm 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 30 w% may be used as an epidermal permeation enhancer, sole or the combination thereof consisting of polyvinypyrrolidone, cellulose etc in an amount ranging from 1 to 30 w% may be used as a dispersing agent; and pressure sensitive adhesive in an amount rainging from 30 to 90w 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, dispersion agent and other conventionally used additives in the art.
  • the composition in the plaster may comprise piroxicam 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 permeating ability, inconstant efficacy and stability of drug, and economic interest. If the amount of piroxicam 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, formation of drug crystal, decrease of adhesive force etc may occur.
  • the alkanolamide adopted by a solubilizer in the present invention is prepared by the condensation reaction between fatty acid, fatty acid derivative and alkanolamine and has been used as a potent solubilizer and binder in the field of cosmetic, sanitary good, cleansing product etc.
  • alkanolamide used as a solubilizer for hydrophobic antibacterial agent
  • Korean Patent No. 2001-8665 discloses lauric diethanolamide used as an epidermal permeation enhancer of oxybutidine!
  • Korean Patent No. 2002-66047 disclose the use as an epidermal permeation enhancer of ketoprofen; United States Patent No.
  • Alkanolamine such as methanolamine, ethanolamine, propanolamine, isopropyl mine or other isopropylamine, preferably, ethanolamine, more preferably, sole or the combination of monoethanolamine, diethanolamine, triethanolamine and the like may be added to the inventive plaster of the present invention to enhancing the solubility for piroxicam in the amount ranging from 0.3 to 3 w%, preferably, 2 to 3 w% in total composition.
  • the amount of alkanolamine is less than 1 w%, the uniformity between adhesive and piroxicam 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 piroxicam and the adhesive ability due to the increased amount of alkanolamine in the preparation.
  • the alkanolamine in the inventive plaster can play a role as a plasicizer as well as show improving effect on the adhesive property of the plaster.
  • N-alkyl-pyrrrolidone preferably, N-methyl-2-pyrrolidione may be used in the present invention as a co-solvent.
  • N-methyl-2-pyrrolidone is easily disappeared in the drying process in spite of its good solubility for piroxicam therefore it can improve skin permeability and minimize skin irritation.
  • the amount of N-alkyl-pyrrolidone ranging from 0.5 to 3 folds of the amount of piroxicam can be preferably used. If the amount is less than 0.5 fold of the amount of piroxicam, additional other solvent to solve piroxicam 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, sorbitane ester, sorbitane 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 or polyglycery-6-olate etc can be used herein.
  • 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.
  • a dispersing agent for preventing from the formation of piroxicam crystal polyvinylpyrrolidone such as povidone K90, K25 etc can be used herein.
  • Those dispersing agents can be used as a sole or the combination thereof with other solubilizer according to the distribution of M. W.
  • the dispersion agent can provide piroxicam with the uniformity with other components in the plaster, inhibit the formation of piroxicam crystal and improve physical property of the plaster such as adhesive force, cohesive force, adhering force etc.
  • the dispersion agent can be used in the amount ranging from 1 to 30 w%, preferably, 3 to 20 w%, more preferably. If the amount of dispersing agent is less than 1 w%, there shows no dispersion effect whereas if more than 30 w%, the adhesive force of the preparation is decreased and the handling of the preparation gets worse because of its increased viscosity.
  • 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 can be used in the present invention.
  • 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 80 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%. > Besides the above described components, other additives, for example, essential oil such as 1-menthol, peppermint oil etc, anti-oxidant , preservative and inorganic filler etc in the amount ranging from 0.2 to 5 w%, among total composition in of drug layer can be further added to improve the physical property of the present preparation.
  • the inventive piroxicam-containing plaster of the present invention could provide all the components in the preparation with equal distribution. Accordingly, it could provide with superior advantages to conventional preparations: it can maintain the uniform distribution and high skin permeability of piroxiacm sufficiently and stably; accordingly, it can maintain ant i-inflammatory effect due to piroxicam sufficiently for a long time; it also provide with superior stability and adherence force of the preparation.
  • Present invention also provide with formulated plaster depicted in Fig. 1 using by the above- described composition as an exemplary embodiment.
  • 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 piroxicam 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 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 piroxicam, 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 piroxicam 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 piroxicam-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 piroxicam-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 Examples, Comparative examples and conventional plaster.
  • Comparative Example 1 Preparation of Comparative plaster (1) o> The mixture of 8 w% povidone K25 and 7 w% povidone K90 used as a dispersing agent were dissolved in ethanol. 5% piroxicam and identical amount of N-methyl-2-pyrrolidone used as a co-solvent were added thereto and stirred to solve completely. 6 w% oleylalcohol and 6 w% polyglyceryl-6-olate used as an epidermal permeation enhancer were added thereto and mixed thoroughly. 68 w% aery adhesive used as a pressure sensitive adhesive was added thereto and stirred for 30 mins sufficiently to obtain sticky material.
  • the sticky material was spread on a release liner in order to the mixture contains 0.38 2 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 piroxicam containing comparative plaster (1) to use as a sample in following Experimental Examples.
  • Comparative plaster (2) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 16 w% piroxicam, 57 w% acrylic adhesive as a pressure sensitive adhesive, and 1.2 2 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Comparative Example 3 Preparation of Comparative plaster (3) b> Comparative plaster (3) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 without dispersing agent except adopting 16 w% piroxicam, 62 w% acrylic adhesive as a pressure sensitive adhesive, 10 w coconut fat diethanolamide used as a solubilizer 2 and 1.2 mg/cm of dry drug content to use as a sample in following Experimental Examples.
  • Example 1 Preparation of inventive plaster (1) > Inventive plaster (1) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 5 w% piroxicam, 58 w% acrylic adhesive as a pressure sensitive adhesive, 10 w% 2 coconut fat diethanolamide used as a solubilizer, and 0.17 mg/cm of dry drug content to use as a sample in following Experimental Examples.
  • Example 2 Preparation of inventive plaster (2) > Inventive plaster (2) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 10 w% piroxicam, 53 w% acrylic adhesive as a pressure sensitive adhesive, 10 w% 2 coconut fat diethanolamide used as a solubilizer, and 0.75 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Example 3 Preparation of inventive plaster (3) > Inventive plaster (3) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 20 w% piroxicam, 43 w% acrylic adhesive as a pressure sensitive adhesive, 10 w% 2 coconut fat diethanolamide as a solubilizer and 1.5 mg/cm of dry 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 25 w% piroxicam, 38 w% acrylic adhesive as a pressure sensitive adhesive, 10 w% 2 coconut fat diethanolamide as a solubilizer and 1.88 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 16 w% piroxicam, 45 w acrylic adhesive as a pressure sensitive adhesive, the mixture of 10 w% coconut fat diethanolamide and 2% diethanolamine as a 2 solubilizer and 1.2 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Example 7' Preparation of inventive plaster (7) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 16 w piroxicam, 47 w% acrylic adhesive as a pressure sensitive adhesive, 10 w% coconut fat diethanolamide as a solubilizer, the mixture of 6% sorbitane monooleic acid and 5 w% ⁇ olyglyceryl-6-olate used as an epidermal permeation 2 enhancer, and 1.2 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 16 w% piroxicam, 47 w% acrylic adhesive as a pressure sensitive adhesive, 10 w% coconut fat diethanolamide as a solubilizer, the mixture of 6% sorbitane monooleic acid and 6 w% oleyl alcohol used as an epidermal permeation 2 enhancer, and 1.2 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 16 w% piroxicam, 47 w% acrylic adhesive as a pressure sensitive adhesive, 10 w% 2 lauric mono ethanol amide as a solubilizer, and 1.2 mg/cm of drug content to use as a sample in following Experimental Examples.
  • Example 1 In order to examine the drug transdermal permeability of the formulations prepared by the procedures disclosed in Example 1 to 10, Comparative Example 1 to 3 and conventionally available plaster, the samples were attached to skin epidermis of four weeks old hairless mouse and then, in vitro drug permeability was measured by using Franz-diffusion cell at 32°C. 2 The effective drug permeation area of diffusion cell was 0.64cm and the volume of solution (phosphate buffer (pH 7.4), 40% Tween 20, 1% sodium ascorbate, 0.1% sodium citrate, 0.1% sodium azide) was 5.2m£. The samples were attached to the diffusion apparatus and the PBS (pH 7.4) was used as a mobile phase. The mobile phase was stirred with a speed of 600rpm.
  • PBS pH 7.4
  • the inventive piroxicam-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 piroxicam-containing plaster to treat and alleviate various inflammation and pain inconsistently.

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

Abstract

Cette invention concerne un emplâtre contenant un composé piroxicam et plus spécifiquement un emplâtre renfermant un composé piroxicam comme agent anti-inflammatoire non stéroïdien (AINS), un solubilisant, un co-solvant, un activateur de perméabilité épidermique, un agent de dispersion et un adhésif autocollant comme support, lequel emplâtre peut procurer un effet anti-inflammatoire durable, une plus grande stabilité et un plus grand pouvoir adhérant par rapport aux emplâtres conventionnels. Cet emplâtre peut par conséquent être utilisé comme emplâtre efficace contenant un composé piroxicam pour traiter et soulager indifféremment diverses inflammations et douleurs.
PCT/KR2004/002966 2003-11-17 2004-11-16 Emplatre antiphlogistique et analgesique comprenant un compose piroxicam WO2005046654A1 (fr)

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KR10-2003-0080982 2003-11-17
KR20030080982A KR100552650B1 (ko) 2003-11-17 2003-11-17 피록시캄 함유 소염진통용 플라스터

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2098254A1 (fr) 2008-03-06 2009-09-09 Bayer MaterialScience AG Colles médicales pour la chirurgie dotées de liaisons bioactives
WO2010095875A2 (fr) * 2009-02-23 2010-08-26 Kim Tae Jin Timbre pour traiter la constipation au moyen de médicaments bruts
US20110293721A1 (en) * 2010-05-27 2011-12-01 Absize, Inc. Piroxicam-containing matrix patches and methods for the topical treatment of acute and chronic pain and inflammation therewith
CN114796100A (zh) * 2022-03-04 2022-07-29 中山大学 一种吡罗昔康凝胶贴膏剂及其制备方法

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Publication number Priority date Publication date Assignee Title
KR101304982B1 (ko) * 2006-05-08 2013-09-06 (주)아모레퍼시픽 경피흡수용 조성물 및 이로부터 형성된 고분자 매트릭스함유 경피흡수제제

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US4879118A (en) * 1984-03-07 1989-11-07 Yamanouchi Pharmaceutical Co., Ltd. Glycyrrhetinic acid-containing plasters
US5413776A (en) * 1990-02-27 1995-05-09 Sekisui Chemical Co., Ltd. Pharmaceutical preparation for percutaneous absorption
WO1997029735A1 (fr) * 1996-02-19 1997-08-21 Monash University Promoteurs de penetration dermique et systeme d'administration de medicaments comprenant ces promoteurs
EP0676962B1 (fr) * 1992-12-31 2001-06-27 Sunkyong Industries Co., Ltd. Compositions pharmaceutiques assurant une absorption percutanee amelioree pour piroxicam
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

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4879118A (en) * 1984-03-07 1989-11-07 Yamanouchi Pharmaceutical Co., Ltd. Glycyrrhetinic acid-containing plasters
US5413776A (en) * 1990-02-27 1995-05-09 Sekisui Chemical Co., Ltd. Pharmaceutical preparation for percutaneous absorption
EP0676962B1 (fr) * 1992-12-31 2001-06-27 Sunkyong Industries Co., Ltd. Compositions pharmaceutiques assurant une absorption percutanee amelioree pour piroxicam
WO1997029735A1 (fr) * 1996-02-19 1997-08-21 Monash University Promoteurs de penetration dermique et systeme d'administration de medicaments comprenant ces promoteurs
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
EP2098254A1 (fr) 2008-03-06 2009-09-09 Bayer MaterialScience AG Colles médicales pour la chirurgie dotées de liaisons bioactives
WO2010095875A2 (fr) * 2009-02-23 2010-08-26 Kim Tae Jin Timbre pour traiter la constipation au moyen de médicaments bruts
WO2010095875A3 (fr) * 2009-02-23 2010-12-09 Kim Tae Jin Timbre pour traiter la constipation au moyen de médicaments bruts
CN102325527A (zh) * 2009-02-23 2012-01-18 金兑镇 利用生药的便秘治疗用贴剂
CN102325527B (zh) * 2009-02-23 2013-09-11 金兑镇 利用生药的便秘治疗用贴剂
US20110293721A1 (en) * 2010-05-27 2011-12-01 Absize, Inc. Piroxicam-containing matrix patches and methods for the topical treatment of acute and chronic pain and inflammation therewith
WO2011150239A3 (fr) * 2010-05-27 2012-06-07 Absize, Inc. Timbres matriciels contenant du piroxicam et procédés pour le traitement topique de la douleur aiguë et chronique et de l'inflammation utilisant lesdits timbres
CN102970986A (zh) * 2010-05-27 2013-03-13 艾毕赛斯公司 含有吡罗昔康的骨架型贴剂以及局部治疗急性和慢性疼痛及其相关炎症的方法
US8563031B2 (en) 2010-05-27 2013-10-22 Absize, Inc. Piroxicam-containing matrix patches and methods for the topical treatment of acute and chronic pain and inflammation therewith
CN102970986B (zh) * 2010-05-27 2015-06-03 南京前沿生物技术有限公司 含有吡罗昔康的骨架型贴剂以及局部治疗急性和慢性疼痛及其相关炎症的方法
CN114796100A (zh) * 2022-03-04 2022-07-29 中山大学 一种吡罗昔康凝胶贴膏剂及其制备方法
CN114796100B (zh) * 2022-03-04 2023-09-22 中山大学 一种吡罗昔康凝胶贴膏剂及其制备方法

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