EP1509210A1 - Timbre contenant du fentanyl - Google Patents

Timbre contenant du fentanyl

Info

Publication number
EP1509210A1
EP1509210A1 EP03755897A EP03755897A EP1509210A1 EP 1509210 A1 EP1509210 A1 EP 1509210A1 EP 03755897 A EP03755897 A EP 03755897A EP 03755897 A EP03755897 A EP 03755897A EP 1509210 A1 EP1509210 A1 EP 1509210A1
Authority
EP
European Patent Office
Prior art keywords
acrylate
therapeutic system
transdermal therapeutic
adhesive matrix
acrylate copolymer
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
EP03755897A
Other languages
German (de)
English (en)
Inventor
Günter Cordes
Ulrike Vollmer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Labtec GmbH
Original Assignee
Labtec Gesellschaft fuer Technologische Forschung und Entwicklung mbH
Labtec GmbH
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=29713116&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP1509210(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from DE10223835A external-priority patent/DE10223835A1/de
Application filed by Labtec Gesellschaft fuer Technologische Forschung und Entwicklung mbH, Labtec GmbH filed Critical Labtec Gesellschaft fuer Technologische Forschung und Entwicklung mbH
Priority to DE20321153U priority Critical patent/DE20321153U1/de
Priority to DE20321052U priority patent/DE20321052U1/de
Priority to EP10011331.5A priority patent/EP2438912B1/fr
Priority to EP07018343.9A priority patent/EP1894563B2/fr
Publication of EP1509210A1 publication Critical patent/EP1509210A1/fr
Ceased legal-status Critical Current

Links

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
    • A61K31/435—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
    • 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
    • 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
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • 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
    • 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
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
    • A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/402—Anaestetics, analgesics, e.g. lidocaine

Definitions

  • the invention relates to a transdermal therapeutic system with a cover layer, an adhesive matrix containing fentanyl as the active ingredient and with a removable protective layer.
  • Fentanylum (fentanyl, fentanil) was patented in 1984 using a transdermal patch (US 45 88 580). Since then, it has proven its worth in the therapy of severe and / or chronic pain conditions, particularly postoperatively, as well as in cancer patients. Side effects in this class of opioids include fentanyl, nausea, circulatory problems, constipation or pruritus and life-threatening respiratory depression, which requires slow and continuous supply to the body. Due to the poor oral bioavailability of ⁇ 10%, oral prolonged-release forms (prolonged-release tablets) cannot be used.
  • transdermal patch Applied transdermally, the first pass effect is avoided in the liver
  • the absorption of the substance through the skin is good and long-lasting, uniform blood levels can be achieved in this way if a suitable transdermal formulation can be developed.
  • the application of fentanyl from a transdermal patch is an ever growing market share in the treatment of severe pain.
  • a transdermal system such as Durogesic TM
  • the fentanyl released from the formulation penetrates the skin barrier in order to enter the systemic bloodstream through the subcutaneous blood flow and from there to develop centrally the analgesic effect by means of a reaction at the opiate receptors in the brain.
  • a skin depot due to the high lipophilicity of the opioid analogue, there is an accumulation in the adipose tissue, which in turn can be released into the circulation at a later point in time - this is called a skin depot.
  • the penetration of drugs through the skin is largely determined by the physicochemical properties of the substance.
  • the octa- nol / water distribution coefficient and the molecular size play a role here (Potts RO, Guy RH in: Gurny R, Teubner A; Dermal and transdermal drug delivery, Wiss. Verlagsges. Stuttgart (1993)). Since the patient prefers to use an effective patch in a size as inconspicuous and small as possible, there is also a desire to increase the penetration rate in this case, although there are actually only two options if the skin is not “microinjected” , Micro lesions or the application of external energy sources (e.g. iontophoresis or the like): 1. Facilitation of diffusion by adding penetration accelerators or applying electrical voltage (iontophoresis)
  • Alcohols, fatty acids, fatty alcohols, simple and polyhydric alcohols, lauro- ' capram and surfactants are used as penetration accelerators. However, many of these substances act by disrupting the skin's barrier function and can therefore be classified as more or less irritating to the skin. Nevertheless, numerous systems are described in patent specifications (cf. WO 89 10 108, WO 9956782, WO 9932153 etc.).
  • the use of systems in which the active ingredient is present in supersaturated form is more compatible.
  • the maximum flux of a substance through the skin is usually limited by its solubility in the cornea (stratum corneum), which is the main barrier to penetration.
  • This saturation concentration will occur when the active substance in the vehicle, for example in the matrix of the transdermal system, is also present in a concentration that corresponds to the solubility in the vehicle.
  • One way to further increase this so-called maximum thermodynamic activity is to incorporate the drug in a concentration that exceeds the solubility in the vehicle. This is possible, for example, by incorporating fentanyl into acrylate copolymers (WO 20024386).
  • the setting of the supersaturation must be so sensitive that the supersaturations are as high as possible, but also as stable as necessary, since supersaturated systems are known to be metastable and, after storage, re-crystallized to a saturated state. s. This then has the disadvantage that, due to the crystallization, these systems lead to product complaints due to a lack of aspect as well as a lack of tack. Close contact between the transdermal system and the skin is also necessary in order to obtain an effective amount of fentanyl in the target area of the blood circulation.
  • fentanyl is one of the few drugs that, due to the physicochemical properties of the substance, permeate very well through the skin barrier and like to migrate and accumulate in polymers. Since the therapeutic range of fentanyl is small and there is also an addictive potential as with all opioids, another wish is to incorporate as little substance as possible but as much as necessary in the development of a transdermal fentanyl patch so that a therapeutic blood level spans several Days can be maintained.
  • the object of the present invention is to develop an improved transdermal therapeutic system of the type mentioned in the introduction.
  • an acrylate copolymer adhesive matrix is used which is free from penetration accelerators, the adhesive matrix being selected from the following group:
  • Adhesives without functional groups were found to be sufficiently stable, but adhesives with a low proportion of hydroxyethyl acrylate (Durotak 387-2510) are clearly superior in terms of thermodynamic activity at the same concentration, which is reflected by better in vitro permeation rates exceded human skin in Franzzellen.
  • the wearing properties are achieved by crosslinking the basic Durotak.
  • Durotak 387-2510, 387-2516 There are many other ways of influencing the cohesion and adhesive properties of these adhesives from National Starch & Chemical (Durotak 387-2510, 387-2516), for example by means of titanium crosslinking agents, or by adding solids such as Aerosil or talc, which are found in others Systems have led to success (P 2000 04447), or by adding other polymers such as silicone, resins, polyisobutylenes (WO 9902141, WO 9300058), but if only the Durotak 387-2510 adhesive mentioned above is used, the use of polybutyl titanate leads to the best result, which was surprising.
  • titanium crosslinker requires some skills on the part of the expert. Depending on the source of supply of the polybutyl titanate, it may have to be incorporated differently.
  • the crosslinker from Aldrich (Germany), for example, can simply be added to the active substance-containing adhesive composition in one go after dissolving it in a little ethanol. If the same procedure is used with crosslinkers from Synetix (Vertec TM, UK), brown particles form in the laminate after a few weeks. Therefore you have to pre-dissolve this crosslinker in heptane, then add ethanol to the mixture (mixing ratio 60:40) so that a 3% crosslinker solution results. This is slowly added to the active substance-containing adhesive mass with vigorous stirring. Only then will a perfect matrix be obtained even after storage.
  • Another possibility of reducing the softening effect of fentanyl on the basic adhesive used is to adjust it by adding a "harder” adhesive, characterized by a proportion of vinyl acetate in the acrylate copolymer. This was successfully achieved by adding an adhesive without functional groups such as Durotak 87-4098.
  • the ratio of 2-hydroxyethyl acrylate to vinyl acetate is no longer 1: 0.4 to 1: 5, but 1: 5.2 or 1: 6 and thus no longer has the positive properties of the high thermodynamic activity and the associated high in vitro release and in vitro skin permeation as in the adhesive mixture according to the invention in which the ratio of hydroxyethyl acrylate to vinyl acetate according to the invention is 1: 0, 4 to 1: 5.
  • the following table provides an overview of the values obtained for those formulations that were tested:
  • the carriers of the matrix play an important role in the wearing properties. Since the transdermal system in the strongest dosage of 100 ⁇ g fentanyl per hour delivery rate already reaches a size of at least 40 cm 2 , which is considerable, a certain flexibility is advantageous for the comfort.
  • the protective film should not be too thin (at least 36 ⁇ m layer thickness, preferably 100 ⁇ m layer thickness), so that the larger systems of 30 cm 2 and more are still easy to handle by the patient.
  • the dermal therapeutic systems according to the invention are preferably such that they consist of a cover layer impermeable to the active substance, an adhesive layer containing the active substance adhering to the cover layer and a removable protective layer.
  • TDS This simplest form of a TDS can be produced in the manner known to the person skilled in the art by mixing a solution of the adhesive or adhesive mixture in a low-boiling solvent with the active ingredient, applying the mixture evenly to a removable protective layer, removing the solvent quantitatively by heating, and that product obtained is covered with a carrier.
  • the applied active substance-containing adhesive layer has a thickness of 20 to 500 ⁇ m.
  • Example 1 According to the Invention:
  • the active substance-containing adhesive mass is homogenized by stirring for one hour and then spread with a doctor blade on a siliconized, 100 ⁇ m thick polyester film (FL 2000 100 ⁇ 1-S, Loparex BV, NL-Apeldoorn) in a wet layer thickness of 310 ⁇ m. After drying (10 min. At 70 ° C and 5 min at 100 ° C), the clear and homogeneous laminate is laminated with a polyester film (Hostaphan RN15, Mitsubishi, D-Frankfurt). A patch of size 10 cm 2 contains 5.5 mg fentanyl with a matrix weight of 55.0 g / m 2 .
  • a patch of size 10 cm 2 contains 5.5 mg fentanyl with a matrix weight of 55.0 g / m 2 .
  • a patch of size 10 cm 2 contains 5.5 mg fentanyl with a matrix weight of 55.0 g / m 2 .
  • Example 2 The formulation corresponded to Example 1 according to the invention, with the exception that instead of a polyester film (Hoestphan RN15, Mitsubishi, D-Frankfurt), a BOPP film was used (Trespaphan NAA 40 ⁇ m, Trespaphan, D-Frankfurt).
  • Each patch size 10 cm 2 tested contained 5.5 mg fentanyl with a matrix weight of 55.0 g / m 2 .
  • the comparative product was called Durogesic TM 25 ⁇ g membrane patch.
  • the results of the kinetics are summarized in the table:
  • the graph in Figure 1 shows the course of the blood levels of both products.
  • the drying conditions reported in the examples were those used on a laboratory scale to make the patches. When manufacturing on a larger scale, the conditions may vary. So the product is e.g. conveyed in a pilot plant in a drying tunnel with 4 drying zones at a speed of 2m / min, the individual zones have temperatures of 40 ° C, 60 ° C, 90 ° C and 120 ° C. In the case of production on a production scale, there may be other conditions which must be determined in the scale-up tests.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dermatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Materials Engineering (AREA)
  • Hematology (AREA)
  • Surgery (AREA)
  • Anesthesiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un système thérapeutique transdermique qui comprend une couche de recouvrement et une matrice adhésive contenant du fentanyl.
EP03755897A 2002-05-28 2003-05-20 Timbre contenant du fentanyl Ceased EP1509210A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DE20321153U DE20321153U1 (de) 2002-05-28 2003-05-20 Pflaster, enthaltend Fentanylum
DE20321052U DE20321052U1 (de) 2002-05-28 2003-05-20 Pflaster, enthaltend Fentanylum
EP10011331.5A EP2438912B1 (fr) 2002-05-28 2003-05-20 Emplâtre comprenant du fentanyl
EP07018343.9A EP1894563B2 (fr) 2002-05-28 2003-05-20 Pavé contenant du fentanyl

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE10223835 2002-05-28
DE10223835A DE10223835A1 (de) 2002-05-28 2002-05-28 Pflaster, enthaltend Fentanylum
US42855602P 2002-11-22 2002-11-22
US428556P 2002-11-22
PCT/DE2003/001635 WO2003101433A1 (fr) 2002-05-28 2003-05-20 Timbre contenant du fentanyl

Related Child Applications (2)

Application Number Title Priority Date Filing Date
EP07018343.9A Division EP1894563B2 (fr) 2002-05-28 2003-05-20 Pavé contenant du fentanyl
EP10011331.5A Division EP2438912B1 (fr) 2002-05-28 2003-05-20 Emplâtre comprenant du fentanyl

Publications (1)

Publication Number Publication Date
EP1509210A1 true EP1509210A1 (fr) 2005-03-02

Family

ID=29713116

Family Applications (2)

Application Number Title Priority Date Filing Date
EP07018343.9A Expired - Lifetime EP1894563B2 (fr) 2002-05-28 2003-05-20 Pavé contenant du fentanyl
EP03755897A Ceased EP1509210A1 (fr) 2002-05-28 2003-05-20 Timbre contenant du fentanyl

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP07018343.9A Expired - Lifetime EP1894563B2 (fr) 2002-05-28 2003-05-20 Pavé contenant du fentanyl

Country Status (9)

Country Link
US (2) US20060039960A1 (fr)
EP (2) EP1894563B2 (fr)
CN (1) CN1655772B (fr)
AT (2) AT10108U3 (fr)
AU (1) AU2003243896B2 (fr)
CA (1) CA2487123C (fr)
DE (1) DE20321052U1 (fr)
MX (1) MXPA04011759A (fr)
WO (1) WO2003101433A1 (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002024157A2 (fr) 2000-09-19 2002-03-28 National Starch And Chemical Investment Holding Corporation Adhesif non reactif, utile dans des systemes d'apport transdermique de medicaments
CN1320008C (zh) * 2005-03-24 2007-06-06 上海交通大学 包含酯基部分带羧基基团的丙烯酸酯的组合物
CN1320006C (zh) * 2005-03-24 2007-06-06 上海交通大学 包含酯基部分带酯基基团的丙烯酸酯的组合物
CN1320009C (zh) * 2005-03-24 2007-06-06 上海交通大学 包含酯基部分带羟基基团的丙烯酸酯的组合物
CN1320005C (zh) * 2005-03-24 2007-06-06 上海交通大学 包含酯基部分带烷烃基的丙烯酸酯的组合物
CN1326894C (zh) * 2005-03-24 2007-07-18 上海交通大学 包含酯基部分带烷氧基的丙烯酸酯的组合物
EP1938808B1 (fr) * 2005-08-22 2011-01-12 Hisamitsu Pharmaceutical Co., Inc. Préparation à usage externe comprenant de la tamsulosine
WO2007038322A1 (fr) * 2005-09-23 2007-04-05 National Starch And Chemical Investment Holding Corporation Adhesifs acryliques a base de polymeres
DE102007020799A1 (de) * 2007-05-03 2008-11-06 Novosis Ag Transdermales therapeutisches System mit Remifentanil
KR20090101579A (ko) * 2008-03-24 2009-09-29 조선대학교산학협력단 펜타닐을 함유한 경피 흡수제
TWI541246B (zh) 2008-12-08 2016-07-11 歐陸斯迪公司 二氫羥戊甲嗎啡
CN101780057B (zh) * 2009-01-21 2012-09-05 考司美德制药株式会社 经皮吸收贴剂
GB201309654D0 (en) 2013-05-30 2013-07-17 Euro Celtique Sa Method
CN107106552A (zh) 2014-12-19 2017-08-29 3M创新有限公司 包含芬太尼的透皮药物递送装置

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0622075A1 (fr) 1993-04-27 1994-11-02 Hercon Laboratories Corporation Administration transdermique de médicaments actifs
EP0887075A2 (fr) 1997-06-26 1998-12-30 Bertek, Inc. Mélange adhésif pour l'administration transdermale de principes actifs fortement plastifiants
WO2002026217A2 (fr) 2000-09-29 2002-04-04 3M Innovative Properties Company Composition pour l'administration transcutanée de fentanyle
WO2003018075A2 (fr) 2001-08-24 2003-03-06 Lts Lohmann Therapie-Systeme Ag Systeme therapeutique transdermique contenant du fentanyle et des substances apparentees

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3321451A (en) * 1965-07-02 1967-05-23 Johnson & Johnson Adhesive compositions
US4185051A (en) * 1977-12-22 1980-01-22 Monsanto Company Pressure sensitive adhesive compositions containing a polymetaloxane
US4588580B2 (en) 1984-07-23 1999-02-16 Alaz Corp Transdermal administration of fentanyl and device therefor
US4906463A (en) 1986-12-22 1990-03-06 Cygnus Research Corporation Transdermal drug-delivery composition
US5474783A (en) 1988-03-04 1995-12-12 Noven Pharmaceuticals, Inc. Solubility parameter based drug delivery system and method for altering drug saturation concentration
CA2039586A1 (fr) * 1990-05-02 1991-11-03 Marian R. Appelt Adhesifs reticules sensibles a la pression et tolerants aux excipients a base d'alcool utilises dans les dispositifs transdermiques et methode de preparation connexe
KR0165875B1 (ko) * 1991-06-10 1999-01-15 . 니트로글리세린 플래스터 및 그의 제조방법
DE69532017T2 (de) * 1994-06-06 2004-08-05 Canon K.K. Gleichstromkompensation für Anzeige mit Zeilensprung
GB9714650D0 (en) 1997-07-11 1997-09-17 Strakan Ltd Block copolymer
AU1728099A (en) 1997-12-22 1999-07-12 Alza Corporation Monoglyceride and ethyl palmitate permeation enhancer compositions
US6312715B1 (en) 1998-05-01 2001-11-06 3M Innovative Properties Company Adhesive microsphere drug delivery composition
JP2000004447A (ja) 1998-06-16 2000-01-07 Mitsubishi Electric Corp 受像管装置
US20020147366A1 (en) 2000-07-07 2002-10-10 Wiggins Michael S. Alkoxylated tertiary and quaternary amine surfactants
DE10110391A1 (de) * 2001-03-03 2002-09-26 Lohmann Therapie Syst Lts Hochflexibles Nikotin transdermales therapeutisches System mit Nikotin als Wirkstoff
ATE364380T1 (de) * 2001-03-16 2007-07-15 Alza Corp Transdermales pflaster zur verabreichung von fentanyl
TW536790B (en) * 2002-06-12 2003-06-11 Powerchip Semiconductor Corp A manufacturing method of flash memory

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0622075A1 (fr) 1993-04-27 1994-11-02 Hercon Laboratories Corporation Administration transdermique de médicaments actifs
EP0887075A2 (fr) 1997-06-26 1998-12-30 Bertek, Inc. Mélange adhésif pour l'administration transdermale de principes actifs fortement plastifiants
WO2002026217A2 (fr) 2000-09-29 2002-04-04 3M Innovative Properties Company Composition pour l'administration transcutanée de fentanyle
WO2003018075A2 (fr) 2001-08-24 2003-03-06 Lts Lohmann Therapie-Systeme Ag Systeme therapeutique transdermique contenant du fentanyle et des substances apparentees

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Produktbeschreibung der Firma 'National Starch and Chemical' hinsichtlich Durotak von Februar 2002; provided by B.H.Steerhuis", 1 February 2002 (2002-02-01), pages 1 - 3, XP002997820
ROY ET AL.: "CONTROLLED TRANSDERMAL DELIVERY OF FENTANYL: CHARACTERIZATIONS OF PRESSURE-SENSITIVE ADHESIVES FOR MATRIX PATCH DESIGN", JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 85, no. 5, May 1996 (1996-05-01), pages 491 - 495, XP000583527
See also references of WO03101433A1

Also Published As

Publication number Publication date
AT10108U2 (de) 2008-09-15
CN1655772B (zh) 2010-05-26
DE20321052U1 (de) 2005-09-22
AT10109U2 (de) 2008-09-15
CA2487123C (fr) 2011-10-18
EP1894563A1 (fr) 2008-03-05
AT10109U3 (de) 2009-07-15
CN1655772A (zh) 2005-08-17
MXPA04011759A (es) 2005-07-27
US20160158161A1 (en) 2016-06-09
CA2487123A1 (fr) 2003-12-11
AU2003243896B2 (en) 2008-07-03
WO2003101433A1 (fr) 2003-12-11
EP1894563B1 (fr) 2010-10-27
AU2003243896A1 (en) 2003-12-19
EP1894563B2 (fr) 2022-04-27
AT10108U3 (de) 2009-07-15
US20060039960A1 (en) 2006-02-23

Similar Documents

Publication Publication Date Title
EP2094213B1 (fr) Système thérapeutique transdermique avec un taux d'utilisation de la substance active élevé et une posologie plus précise
DE60314298T2 (de) Therapeutisches pflaster mit capsaicin-haltiger polysiloxan-matrix
EP0617972B1 (fr) Système thérapeutique dermique à base d'un mélange de polyméthacrylates fusibles
US20160158161A1 (en) Plaster containing fentanyl
EP1178782B1 (fr) Systeme therapeutique transdermique (stt) contenant de la tolterodine
EP2559427B1 (fr) Système thérapeutique transdermique contenant un modulateur de récepteurs nicotiniques de l'acétylcholine (nAChR)
EP0817622A1 (fr) Medicament a administration transdermique, comportant des inhibiteurs de l'enzyme de conversion de l'angiotensine
EP0781134A1 (fr) Emplatre a la scopolamine
DE102006019293A1 (de) Pflaster, enthaltend ein Fentanyl Analogum
EP2438912B1 (fr) Emplâtre comprenant du fentanyl
DE102008006791B4 (de) Transdermales Therapeutisches System mit Harnstoff-Komponente und Verfahren zu dessen Herstellung
DE20321153U1 (de) Pflaster, enthaltend Fentanylum
EP1296662B1 (fr) Systeme therapeutique dermique contenant de l'acide 2-(3-benzophenyl)-propionique ou de l'acide '0-(2,6-dichloranilino)-phenyl!-acetique
DE10025971B4 (de) Transdermales therapeutisches System in Plasterform mit verminderter Tendenz zur Wirkstoffkristallisation und seine Verwendung
DE10049225A1 (de) Dermales System, enthaltend Diclofenac
EP2614820A1 (fr) Système thérapeutique transdermique doté d'un inhibiteur de la cholinestérase
DE3843557A1 (de) Transdermales therapeutisches system zur verabreichung von clenbuterol
WO1994005295A1 (fr) Systeme therapeutique percutane contenant du pentylenetetrazol comme principe actif
KR20050019084A (ko) 펜타닐을 함유하는 패치
DE10317108A1 (de) Transdermal applizierbares Beruhigungs- und Sedierungsmittel
EP0992237A2 (fr) Neohesperidine dc comme inhibiteur de cristallisation

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20041104

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL LT LV MK

DAX Request for extension of the european patent (deleted)
TPAC Observations filed by third parties

Free format text: ORIGINAL CODE: EPIDOSNTIPA

17Q First examination report despatched

Effective date: 20070411

TPAC Observations filed by third parties

Free format text: ORIGINAL CODE: EPIDOSNTIPA

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: LABTEC GMBH

APBK Appeal reference recorded

Free format text: ORIGINAL CODE: EPIDOSNREFNE

APBN Date of receipt of notice of appeal recorded

Free format text: ORIGINAL CODE: EPIDOSNNOA2E

APBR Date of receipt of statement of grounds of appeal recorded

Free format text: ORIGINAL CODE: EPIDOSNNOA3E

APAF Appeal reference modified

Free format text: ORIGINAL CODE: EPIDOSCREFNE

APAF Appeal reference modified

Free format text: ORIGINAL CODE: EPIDOSCREFNE

REG Reference to a national code

Ref country code: DE

Ref legal event code: R003

APBT Appeal procedure closed

Free format text: ORIGINAL CODE: EPIDOSNNOA9E

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN REFUSED

18R Application refused

Effective date: 20140505