WO2004032927A1 - Preparations transdermiques comprenant l'eperisone, la tolperisone ou leurs sels - Google Patents

Preparations transdermiques comprenant l'eperisone, la tolperisone ou leurs sels Download PDF

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Publication number
WO2004032927A1
WO2004032927A1 PCT/KR2003/002086 KR0302086W WO2004032927A1 WO 2004032927 A1 WO2004032927 A1 WO 2004032927A1 KR 0302086 W KR0302086 W KR 0302086W WO 2004032927 A1 WO2004032927 A1 WO 2004032927A1
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WO
WIPO (PCT)
Prior art keywords
acrylic adhesive
transdermal preparations
hydroxy
hydroxy group
fatty acid
Prior art date
Application number
PCT/KR2003/002086
Other languages
English (en)
Inventor
Wan Suk Lee
Young Hee Shin
Jin Hyuk Choi
Yeong Dae Lee
Jung Ju Kim
Original Assignee
Amorepacific Corporation
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 Amorepacific Corporation filed Critical Amorepacific Corporation
Priority to AU2003269511A priority Critical patent/AU2003269511A1/en
Priority to JP2004542906A priority patent/JP2006503877A/ja
Publication of WO2004032927A1 publication Critical patent/WO2004032927A1/fr

Links

Classifications

    • 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
    • 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
    • A61K31/435—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
    • A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system

Definitions

  • Transdermal preparations comprising eperisone, tolperisone or salts thereof
  • the present invention relates to transdermal preparations comprising eperisone, tolperisone or salts thereof (hereinafter, referred to as "eperisone etc.”), which are skeletal muscle relaxant.
  • Spasticity is one of skeletal muscle disorders due to increase of muscle tone, and appears following lesions of the central nervous system such as ischemic stroke, trauma and several types of neuronal degeneration. Since various neurotransmitters, neuromodulators, receptors and related ion-channels are involved in the intern euronal control of muscle tone, centrally acting muscle relaxant is usually used for the treatment of spasm. Centrally acting muscle relaxant reduces the increased muscle tone and inhibits the hyperactive reflexes by antagonizing the receptor activation coupled to the excitation of motor functions or by acting on the receptors related to inhibitory functions. Problems in using such centrally acting muscle relaxant are central depression and muscle weakness.
  • Eperisone etc. a centrally acting muscle relaxant with a low incidence of central depression, are widely used in the treatment of muscle spasm for the relief of myotonia and spinalgia.
  • Eperisone etc. inhibit both monosynaptic and polysynaptic reflex via acting on spinal cord and upper central level, leading to exhibition of muscle relaxation through decrease of muscle tone.
  • eperisone etc. exhibit disadvantages, i.e. very low bioavailability and variable plasma level due to first-pass effect during absorption. Further, frequent administration is needed due to very short duration of the muscle relaxation effect of absorbed eperisone etc. and all commercial products are injection or oral preparations, have a problem in patient's compliance.
  • U.S. Pat. No. 5,252,588 discloses the transdermal preparations comprising eperisone and water-swellable crosslinked polyvinylpyrrolidone.
  • the present invention provides formulations which, compared to the USP 5,252,588, exhibit superior skin permeation and have adequate adhesive property upon attachment on the skin, thereby achieving good adhesion through application period and providing less pain and less skin abrasion at the time of removal, thus more convenience for patients.
  • the present invention is to provide transdermal preparations that guarantee stability of eperisone etc. within adhesives, and have skin adhesion adequate for application while maximizing skin permeation of the drug.
  • the present invention relates to transdermal preparations having adhesive layer comprising drug selected from eperisone, tolperisone and salts thereof, and, as an adhesive, mixture of acrylic adhesive having hydroxy group and acrylic adhesive without hydroxy group.
  • Drug used in the present invention is selected among eperisone, tolperisone and their salts, and as a salt, hydrochloride or phosphate is preferred.
  • Eperisone, tolperisone or salts thereof can exist within adhesives as dissolved or crystal state, and preferably, the content of the drug is 5 to 20 w/w% to total weight of the adhesive layer.
  • skin permeation of drug increases in proportion to drug concentration within adhesives. Therefore, in case drug concentration within adhesives is too low, it is unable to deliver sufficient amount of drug for pharmacological effect through the skin.
  • drug concentration is too high, skin permeation of the drug increases no more over certain level, and affects physical property of adhesive layer, resulting in adverse effect on skin adhesion of the preparation.
  • Acrylic adhesive used in the present invention consists of mixture of acrylic adhesive having hydroxy group and acrylic adhesive without hydroxy group. Mixing ratio of acrylic adhesive having hydroxy group and hydroxy-free acrylic adhesive is preferred to be in a range of 8:2 to 5:5, by weight ratio. Said adhesives are used in viscous liquid state with addition of organic solvent, and majority of the organic solvent is evaporated upon drying after coating and only acrylic adhesive is remained.
  • Acrylic adhesive having hydroxy group is used to maximize skin permeation of drug.
  • the acrylic adhesive having hydroxy group consists of copolymer of monomer with hydroxy group and monomer without hydroxy group.
  • the monomer having hydroxy group at least one selected from a group consisting of hydroxyethyl(metha)acrylate and hydroxypropyl(metha)acrylate can be used.
  • the monomer having hydroxy group is used, preferably, 1 to 20 w/w% of total weight of monomer used for polymerization of acrylic adhesive having hydroxy group.
  • the monomer without hydroxy group one or more monomer selected from a group consisting of general alkyl(metha)acrylate monomer such as butylacrylate, methylacrylate, methylmethacrylate and 2-ethylhexylacrylate, acrylic acid and vinylacetate, can be used.
  • general alkyl(metha)acrylate monomer such as butylacrylate, methylacrylate, methylmethacrylate and 2-ethylhexylacrylate, acrylic acid and vinylacetate
  • the monomer without hydroxy group it is preferred to use 2- ethylhexyl acrylate and vinylacetate together, and 2-ethylhexylacrylate is preferred to be in a range of 49 - 80 w/w% of total weight of acrylic adhesive having hydroxy group, and vinylacetate is preferred to be in a range of 19 - 50 w/w% of total weight of acrylic adhesive having hydroxy group.
  • acrylic adhesive without hydroxy group, as it contains no functional group to react with drug, eperisone etc., it raises stability of eperisone etc. within adhesives, thus used along with acrylic adhesive having hydroxy group.
  • Said acrylic adhesive without hydroxy group consists of copolymer between general alkyl(metha)acrylate monomer such as butylacrylate, methylacrylate, methylmethacrylate and 2-ethylhexylacrylate, and vinylacetate monomer.
  • acrylic adhesive without hydroxy group consists of 2-ethylhexylacrylate and vinylacetate monomer, and 2-ethylhexylacrylate is preferred to be in a range of 50- 80 w/w% to total weight of hydroxy-free acrylic adhesive and vinyl acetate is preferred to be in a range of 20 -50 w/w% to total weight of hydroxy-free acrylic adhesive.
  • General acrylic adhesive used in prior technology has carboxyl group. This is derived from acrylic acid, one of the monomers used for adhesives. Such general acrylic adhesive has carboxyl group alone or both carboxyl group and hydroxy group.
  • acrylic adhesive Duro-Tak 87-2074, Duro-Tak 87-2194, Duro-Tak 87-2353, Duro-Tak 87-2677 and Duro-Tak 87-2825 (National Starch and Chemical) can be enumerated, and as acrylic adhesive having amide group, Duro-Tak 87-9301 (National Starch and Chemical) can be enumerated, and there is also acrylic adhesive having vinylpyrrolidone such as TSR (Sekisui). Such acrylic adhesive is not used in the present invention but was used for a comparison.
  • the preparations according to the present invention can contain further solubilizer to raise the content of eperisone etc. within adhesive layer.
  • solubilizer is used to allow fixed concentration of eperisone etc. to be contained within adhesive layer whose main component is acrylic adhesive.
  • solubilizer distilled water, ethanol, isopropanol, diethyleneglycol monoethylether, polyethyleneglycol, glycerin and dimethylsulfoxide can be enumerated and one or more of them can be used, and the amount thereof is preferred to be 1- 20w/w% of total weight of adhesive layer.
  • preparations of the present invention can further contain skin permeation enhancer to increase percutaneous abso ⁇ tion rate of eperisone etc..
  • higher fatty acid such as oleic acid; higher alcohol such as lauryl alcohol; higher fatty acid ester such as isopropyl myristate; fatty acid ester of glycerin such as glyceryl monolaurate; fatty acid ether of polyethyleneglycol such as polyethyleneglycol lauryl ether; fatty acid ester of polyethyleneglycol such as polyethyleneglycol laurate; fatty acid ether of propyleneglycol such as propyleneglycol lauryl ether; fatty acid ester of propyleneglycol such as propyleneglycol laurate; sorbitan fatty acid ester such as sorbitan monolaurate; polyethyleneglycol sorbitan fatty acid ester such as polyethyleneglycol sorbitan monolaurate; terpenes such as menthol, menthol derivatives and limonene; sulfoxides such as dimethylsulfate, sorbitan fatty acid ester
  • transdermal preparations such backing material as used in conventional transdermal preparations can be used.
  • material with good permeability to air and moisture such as non-woven fabric, cotton cloth and woven fabric, or mono film or multi film laminate of polyethylene terephthalate, polyurethane, polyethylene, polypropylene, ethylenevinylacetate and aluminum-treated polyethylene can be used , and if necessary, non-woven fabric or cotton cloth can be laminated with plastic film that is not moisture permeable, to be used.
  • the transdermal preparations comprising eperisone etc. according to the present invention is characterized by being matrix type or drug-in-adhesive type patch. In case of such patch, the formulation is not much different from plaster and cataplasm, thus can have the form of plaster or cataplasm.
  • Acrylic adhesive (Duro-Tak 87-2194) 70 w/w%(dried weight)
  • dried weight means the weight resulted from evaporation of organic solvent contained in said adhesive product.
  • Acrylic adhesive (Duro-Tak 87-9301) 70 w/w%(dried weight)
  • Acrylic adhesive (Gelva® Multipolymer Solution 3083) 70 w/w%(dried weight)
  • Acrylic adhesive (Duro-Tak 87-2516 ) 70 w/w%(dried weight)
  • Acrylic adhesive (Duro-Tak 87-4098) 87 w/w%(dried weight)
  • Eperisone hydrochloride, polyoxyethylene (2) lauryl ether and propyleneglycol were added to acrylic adhesive and completely dissolved by stirring. 2. Said mixture was coated on release liner to allow depth after drying to be 100 ⁇ m.
  • Acrylic adhesive (Duro-Tak 87-4098) 85 w/w%(dried weight)
  • Eperisone hydrochloride, propyleneglycol monolaurate and diethyleneglycol monoethylether were mixed with two kinds of acrylic adhesives and completely dissolved by stirring.
  • Eperisone hydrochloride, propyleneglycol monolaurate and diethyleneglycol monoethylether were mixed with two kinds of acrylic adhesives and completely dissolved by stirring.
  • Acrylic adhesive (Duro-Tak 87-2287) 51 w/w%(dried weight)
  • Acrylic adhesive (Duro-Tak 87-4098) 34 w/w% (dried weight)
  • Eperisone hydrochloride, propyleneglycol monolaurate and diethyleneglycol monoethylether were mixed with two kinds of acrylic adhesives and completely dissolved by stirring. 2. Said mixture was coated on release liner to allow depth after drying to be 50 ⁇ m.
  • Acrylic adhesive (Duro-Tak 87-2287) 59.5 w/w%(dried weight) Acrylic adhesive (Duro-Tak 87-4098) 25.5 w/w% (dried weight)
  • Eperisone hydrochloride, propyleneglycol monolaurate and diethyleneglycol monoethylether were mixed with two kinds of acrylic adhesives and completely dissolved by stirring.
  • Acrylic adhesive (Duro-Tak 87-2287) 59.5 w/w%(dried weight)
  • Acrylic adhesive (Duro-Tak 87-4098) 25.5 w/w% (dried weight)
  • the skin was mounted on franz-type diffusion cell in such mode that the portion to which the patch was attached faces the upside, and the lower part of the device was filled with buffer solution of desired pH and the diffusion cell was maintained at 37°C.
  • Receptor solution buffer solution
  • Receptor solution buffer solution
  • the sample was subjected to HPLC analysis and the result was represented in Table 1.
  • the patch using higher content of acrylic adhesive with hydroxy group e.g. Examples 1 to 3, showed superior flux over the others.
  • the present invention relates to transdermal preparations comprising eperisone etc, central skeletal muscle relaxant, which achieve extension of drug effect duration compared to the conventional oral preparation or injections, enabling development of once a day or once on alternate days formulation, and exhibit superior skin permeation over that introduced in the prior patent, providing transdermal preparations of smaller size.

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  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Medicinal Preparation (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Neurology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention porte sur des préparations transdermiques comprenant l'épérisone, la tolpérisone ou leurs sels qui sont des décontracturants des muscles squelettiques, et notamment sur des préparations transdermiques qui se caractérisent en ce que, lors de l'administration de l'épérisone, la tolpérisone ou de leurs sels dans la peau, le mélange du rapport fixe de l'adhésif acrylique possédant un groupe hydroxy et de l'adhésif acrylate sans groupe hydroxy est utilisé comme substrat, ce qui maximise l'absorption percutanée de l'épérisone, la tolpérisone ou de leurs sels, augmente leur stabilité dans la couche du substrat et assure une meilleure adhésion sur la peau.
PCT/KR2003/002086 2002-10-11 2003-10-10 Preparations transdermiques comprenant l'eperisone, la tolperisone ou leurs sels WO2004032927A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2003269511A AU2003269511A1 (en) 2002-10-11 2003-10-10 Transdermal preparations comprising eperisone, tolperisone or salts thereof
JP2004542906A JP2006503877A (ja) 2002-10-11 2003-10-10 エペリゾン、トルペリゾン又はそれらの塩を含む経皮製剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2002-0061972A KR100511492B1 (ko) 2002-10-11 2002-10-11 에페리손, 톨페리손 또는 그것들의 염을 포함하는경피흡수제제
KR10-2002-0061972 2002-10-11

Publications (1)

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WO2004032927A1 true WO2004032927A1 (fr) 2004-04-22

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JP (1) JP2006503877A (fr)
KR (1) KR100511492B1 (fr)
CN (1) CN100469367C (fr)
AU (1) AU2003269511A1 (fr)
WO (1) WO2004032927A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006151927A (ja) * 2004-12-01 2006-06-15 Toin Gakuen 光線力学的治療用組成物
WO2006099374A1 (fr) * 2005-03-10 2006-09-21 3M Innovative Properties Company Compositions antivirales et leurs methodes d'utilisation
WO2010103544A2 (fr) 2009-03-09 2010-09-16 Dinesh Shantilal Patel Nouvelle composition à libération prolongée de composés choisis dans la classe des relaxants musculaires à action centrale
US8372979B2 (en) 2007-04-26 2013-02-12 Sanochemia Pharmazeutika Ag Process for the production of high-purity 2,4′-dimethyl-3-piperidino-propiophenone (tolperisone), pharmaceutical compositions that contain the latter, as well as active ingredient formulations that contain tolperisone
US20150098982A1 (en) * 2013-10-07 2015-04-09 Teikoku Pharma Usa, Inc. Methods and Compositions for Managing Pain Comprising Dexmedetomidine Transdermal Compositions
US20160367494A1 (en) * 2015-06-17 2016-12-22 Nitto Denko Corporation Patch preparation
US9826770B2 (en) 2005-03-10 2017-11-28 3M Innovative Properties Company Antimicrobial compositions comprising esters of hydroxycarboxylic acids
US10471036B2 (en) 2003-09-09 2019-11-12 3M Innovative Properties Company Antimicrobial compositions and methods
US10772871B2 (en) 2013-10-07 2020-09-15 Teikoku Pharma Usa, Inc. Dexmedetomidine transdermal delivery devices and methods for using the same
US10874642B2 (en) 2013-10-07 2020-12-29 Teikoku Pharma Usa, Inc. Methods and compositions for treating attention deficit hyperactivity disorder, anxiety and insomnia using dexmedetomidine transdermal compositions
US10918618B2 (en) 2005-03-10 2021-02-16 3M Innovative Properties Company Methods of reducing microbial contamination
US10987342B2 (en) 2013-10-07 2021-04-27 Teikoku Pharma Usa, Inc. Methods and compositions for transdermal delivery of a non-sedative amount of dexmedetomidine

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101832842B1 (ko) * 2012-01-13 2018-02-27 한미약품 주식회사 안정성이 향상된 에페리손 또는 이의 약학적으로 허용 가능한 염 및 특정 산성화제를 포함하는 약학 조성물

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JPH04182424A (ja) * 1990-11-16 1992-06-30 Nitto Denko Corp エペリゾン含有貼付製剤
JPH0640917A (ja) * 1991-06-21 1994-02-15 Nichiban Co Ltd トルペリゾン又はエペリゾン含有ハップ剤
JPH08291067A (ja) * 1995-04-21 1996-11-05 Sekisui Chem Co Ltd エペリゾン外用貼付剤
EP1163902A2 (fr) * 2000-06-16 2001-12-19 Pacific Corporation Préparation transdermique contenant un principe actif hydrosoluble ou sous forme de son sel

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JP2693212B2 (ja) * 1989-03-28 1997-12-24 日東電工株式会社 疾患治療用テープ製剤
JPH03141223A (ja) * 1989-10-26 1991-06-17 Nitto Denko Corp 外用製剤
KR930007407A (ko) * 1991-10-10 1993-05-20 이헌조 취반기의 적정수량 자동판정 장치 및 방법
JP4145996B2 (ja) * 1998-08-03 2008-09-03 日東電工株式会社 アクリル系粘着テープおよび経皮吸収製剤

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04182424A (ja) * 1990-11-16 1992-06-30 Nitto Denko Corp エペリゾン含有貼付製剤
JPH0640917A (ja) * 1991-06-21 1994-02-15 Nichiban Co Ltd トルペリゾン又はエペリゾン含有ハップ剤
JPH08291067A (ja) * 1995-04-21 1996-11-05 Sekisui Chem Co Ltd エペリゾン外用貼付剤
EP1163902A2 (fr) * 2000-06-16 2001-12-19 Pacific Corporation Préparation transdermique contenant un principe actif hydrosoluble ou sous forme de son sel

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10471036B2 (en) 2003-09-09 2019-11-12 3M Innovative Properties Company Antimicrobial compositions and methods
JP2006151927A (ja) * 2004-12-01 2006-06-15 Toin Gakuen 光線力学的治療用組成物
US9826770B2 (en) 2005-03-10 2017-11-28 3M Innovative Properties Company Antimicrobial compositions comprising esters of hydroxycarboxylic acids
WO2006099374A1 (fr) * 2005-03-10 2006-09-21 3M Innovative Properties Company Compositions antivirales et leurs methodes d'utilisation
AU2006223065B2 (en) * 2005-03-10 2011-10-27 3M Innovative Properties Company Antiviral compositions and methods of use
US10918618B2 (en) 2005-03-10 2021-02-16 3M Innovative Properties Company Methods of reducing microbial contamination
US9675598B2 (en) 2007-04-26 2017-06-13 Sanochemia Pharmazeutika Ag Compositions of tolperisone
US9315480B2 (en) 2007-04-26 2016-04-19 Sanochemia Pharmazeutika Ag Compositions of tolperisone
US9662317B2 (en) 2007-04-26 2017-05-30 Sanochemia Pharmazeutika Ag Methods of administering tolperisone for therapeutic purposes
US8372979B2 (en) 2007-04-26 2013-02-12 Sanochemia Pharmazeutika Ag Process for the production of high-purity 2,4′-dimethyl-3-piperidino-propiophenone (tolperisone), pharmaceutical compositions that contain the latter, as well as active ingredient formulations that contain tolperisone
WO2010103544A3 (fr) * 2009-03-09 2011-04-07 Dinesh Shantilal Patel Nouvelle composition à libération prolongée de composés choisis dans la classe des relaxants musculaires à action centrale
WO2010103544A2 (fr) 2009-03-09 2010-09-16 Dinesh Shantilal Patel Nouvelle composition à libération prolongée de composés choisis dans la classe des relaxants musculaires à action centrale
US20150098982A1 (en) * 2013-10-07 2015-04-09 Teikoku Pharma Usa, Inc. Methods and Compositions for Managing Pain Comprising Dexmedetomidine Transdermal Compositions
US10772871B2 (en) 2013-10-07 2020-09-15 Teikoku Pharma Usa, Inc. Dexmedetomidine transdermal delivery devices and methods for using the same
US10874642B2 (en) 2013-10-07 2020-12-29 Teikoku Pharma Usa, Inc. Methods and compositions for treating attention deficit hyperactivity disorder, anxiety and insomnia using dexmedetomidine transdermal compositions
US10987342B2 (en) 2013-10-07 2021-04-27 Teikoku Pharma Usa, Inc. Methods and compositions for transdermal delivery of a non-sedative amount of dexmedetomidine
US20240245652A1 (en) * 2013-10-07 2024-07-25 Teikoku Pharma Usa, Inc. Methods and compositions for managing pain comprising dexmedetomidine transdermal compositions
US20160367494A1 (en) * 2015-06-17 2016-12-22 Nitto Denko Corporation Patch preparation
CN106256348A (zh) * 2015-06-17 2016-12-28 日东电工株式会社 贴片制剂

Also Published As

Publication number Publication date
KR20040033082A (ko) 2004-04-21
JP2006503877A (ja) 2006-02-02
CN100469367C (zh) 2009-03-18
KR100511492B1 (ko) 2005-08-31
CN1703219A (zh) 2005-11-30
AU2003269511A1 (en) 2004-05-04

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