CA2487123A1 - Patch containing fentanyl - Google Patents
Patch containing fentanyl Download PDFInfo
- Publication number
- CA2487123A1 CA2487123A1 CA002487123A CA2487123A CA2487123A1 CA 2487123 A1 CA2487123 A1 CA 2487123A1 CA 002487123 A CA002487123 A CA 002487123A CA 2487123 A CA2487123 A CA 2487123A CA 2487123 A1 CA2487123 A1 CA 2487123A1
- Authority
- CA
- Canada
- Prior art keywords
- accordance
- therapeutic system
- transdermal therapeutic
- acrylate
- adhesive matrix
- 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.)
- Granted
Links
- PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 title claims abstract 5
- 229960002428 fentanyl Drugs 0.000 title claims abstract 5
- 230000001225 therapeutic effect Effects 0.000 claims abstract 15
- 239000011159 matrix material Substances 0.000 claims abstract 14
- 239000000853 adhesive Substances 0.000 claims abstract 13
- 230000001070 adhesive effect Effects 0.000 claims abstract 13
- 229920001577 copolymer Polymers 0.000 claims abstract 12
- 239000010410 layer Substances 0.000 claims abstract 6
- 239000003431 cross linking reagent Substances 0.000 claims abstract 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000004480 active ingredient Substances 0.000 claims abstract 2
- 230000035515 penetration Effects 0.000 claims abstract 2
- 239000011241 protective layer Substances 0.000 claims abstract 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical group OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 7
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 4
- 239000013543 active substance Substances 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000004743 Polypropylene Substances 0.000 claims 2
- 229920000728 polyester Polymers 0.000 claims 2
- -1 polypropylene Polymers 0.000 claims 2
- 229920001155 polypropylene Polymers 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Materials Engineering (AREA)
- Surgery (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Anesthesiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a transdermal therapeutic system with a cover layer, an adhesive matrix that contains fentanyl as the active ingredient and a removable protective layer, wherein the adhesive matrix contains no penetration accelerators and comprises a basic acrylate copolymer and polybutyl titanate, in a molar concentration of 0.1 to 1%, as a crosslinking agent.
Claims (14)
1. Transdermal therapeutic system with a cover layer, an adhesive matrix that contains fentanyl as the active ingredient, and a removable protective layer, characterized by an acrylate copolymer adhesive matrix that contains no penetration accelerators, such that the adhesive matrix is selected from the following group:
(a) basic acrylate copolymer, especially acrylate copolymer with hydroxyethyl acrylate units and with an organotitanium compound as a crosslinking agent; and (b) basic acrylate copolymer with vinyl acetate units and free of crosslinking agents, especially acrylate copolymer with hydroxyethyl acrylate units and vinyl acetate units.
(a) basic acrylate copolymer, especially acrylate copolymer with hydroxyethyl acrylate units and with an organotitanium compound as a crosslinking agent; and (b) basic acrylate copolymer with vinyl acetate units and free of crosslinking agents, especially acrylate copolymer with hydroxyethyl acrylate units and vinyl acetate units.
2. Transdermal therapeutic system in accordance with Claim 1, characterized by a fentanyl concentration of 0.1 to 30 wt.%
and especially 5 to 18 wt.%, based an the weight of the adhesive matrix with the active substance.
and especially 5 to 18 wt.%, based an the weight of the adhesive matrix with the active substance.
3. Transdermal therapeutic system in accordance with Claim 1 and/or Claim 2, characterized by a residual content of fentanyl solvent, especially ethyl alcohol, of less than 0.25 wt.%, based on the weight of the adhesive matrix with the active substance.
4. Transdermal therapeutic system in accordance with one or more of the preceding claims, characterized by (a) an acrylate copolymer comprising units that originate exclusively front 2-ethylhexyl acrylate, methacrylate, and 2-hydroxyethyl acrylate, or (b) an acrylate copolymer comprising units that originate exclusively from 2-ethylhexyl acrylate, methacrylate, 2-hydroxyethyl acrylate, and vinyl acetate.
5. Transdermal therapeutic system in accordance with one or more of the preceding claims, characterized by an acrylate copolymer as the adhesive matrix, which can be produced by drying at a temperature of about 70°C or at a temperature above 70°C.
6. Transdermal therapeutic system in accordance with one or more of the preceding claims, characterized by an acrylate copolymer as the adhesive matrix in accordance with Claim (a), which can he produced by crosslinking of the hydroxyl groups of the acrylate copolymer and subsequent addition of the active substance.
7. Transdermal therapeutic system in accordance with one or more of Claims 1 to 5, characterized by an adhesive matrix in accordance with Claim 1(b), which can be produced from 2-ethylhexyl acrylate, methacrylate. 2-hydroxyethyl acrylate, and vinyl acetate in a ratio of 2-hydroxyethyl acrylate:vinyl acetate of 1:0.3 to 1:5, preferably 1:0.4 to 1:5, more preferably 1:0.6 to 1:5, and most preferably 1:2.2 to 1:5, in each case on the basis of the number of moles or on the basis of weight.
8. Transdermal therapeutic system in accordance with Claim 7, characterized by an adhesive matrix in accordance with Claim 1(b), which can be produced from 2-ethylhexyl acrylate, methacrylate, 2-hydroxyethyl acrylate, and vinyl acetate in a ratio of 2-hydroxyethyl acrylate:vinyl acetate of 1:1.5 to 1:3.0, and especially about 1:2.2, in each case on the basis of the number of moles or on the basis of weight.
9. Transdermal therapeutic system in accordance with one or more of claims 1 to 6, characterized by an acrylate copolymer as the adhesives matrix in accordance with Claim 1(a) with polybutyl titanate as the crosslinking agent.
10. Transdermal therapeutic system in accordance with Claim 10, characterized by a concentration of polybutyl titanate in an amount of 0.1 to 1%, and preferably 0.4 to 0.6%, calculated on the basis of the number of moles.
11. Transdermal therapeutic system in accordance with one or more of the preceding claims, characterized by a layer thickness of the adhesive matrix of 20 to 500 µm.
12. Transdermal therapeutic system in accordance with one or more of the preceding claims, characterized by a cover layer based on polypropylene and especially by a biaxially oriented, longitudinally and transversely aligned polypropylene film.
13. Transdermal therapeutic system in accordance with one or more of preceding Claims 1 to 11, characterized by a cover layer based on polyester and especially by a polyester fabric.
14. Transdermal therapeutic system in accordance with any of Claims 1 to 13, characterized by the fact that the cover layer is designed as a matrix carrier.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10223835.9 | 2002-05-28 | ||
| DE10223835A DE10223835A1 (en) | 2002-05-28 | 2002-05-28 | Transdermal therapeutic system for delivery of fentanyl, to treat severe and/or chronic pain, including drug-containing adhesive matrix of specific basic acrylate copolymer requiring no penetration accelerators |
| US42855602P | 2002-11-22 | 2002-11-22 | |
| US60/428,556 | 2002-11-22 | ||
| PCT/DE2003/001635 WO2003101433A1 (en) | 2002-05-28 | 2003-05-20 | Plaster containing fentanyl |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2487123A1 true CA2487123A1 (en) | 2003-12-11 |
| CA2487123C CA2487123C (en) | 2011-10-18 |
Family
ID=29713116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2487123A Expired - Lifetime CA2487123C (en) | 2002-05-28 | 2003-05-20 | Patch containing fentanyl |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US20060039960A1 (en) |
| EP (2) | EP1894563B2 (en) |
| CN (1) | CN1655772B (en) |
| AT (2) | AT10109U3 (en) |
| AU (1) | AU2003243896B2 (en) |
| CA (1) | CA2487123C (en) |
| DE (1) | DE20321052U1 (en) |
| MX (1) | MXPA04011759A (en) |
| WO (1) | WO2003101433A1 (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001292781A1 (en) | 2000-09-19 | 2002-04-02 | National Starch And Chemical Investment Holding Corporation | Acryl adhesive useful in transdermal drug delivery systems |
| CN1320008C (en) * | 2005-03-24 | 2007-06-06 | 上海交通大学 | Combination of acrylic ester containing ester group including partial radical of carboxyl group |
| CN1320006C (en) * | 2005-03-24 | 2007-06-06 | 上海交通大学 | Combination of acrylic ester containing ester group including partial radical of ester group |
| CN1320005C (en) * | 2005-03-24 | 2007-06-06 | 上海交通大学 | Combination of acrylic ester containing ester group including paraffin base |
| CN1326894C (en) * | 2005-03-24 | 2007-07-18 | 上海交通大学 | Combination of acrylic ester containing ester group including partial alkoxyl |
| CN1320009C (en) * | 2005-03-24 | 2007-06-06 | 上海交通大学 | Combination of acrylic ester containing ester group including partial radical of hydroxy group |
| WO2007023791A1 (en) * | 2005-08-22 | 2007-03-01 | Hisamitsu Pharmaceutical Co., Inc. | Preparation for external use |
| KR101170705B1 (en) * | 2005-09-23 | 2012-08-07 | 헨켈 아게 운트 코. 카게아아 | Acrylic polymer-based adhesives |
| DE102007020799A1 (en) * | 2007-05-03 | 2008-11-06 | Novosis Ag | Transdermal therapeutic system with remifentanil |
| KR20090101579A (en) * | 2008-03-24 | 2009-09-29 | 조선대학교산학협력단 | Transdermal drug delivery system containing fentanyl |
| TWI541246B (en) | 2008-12-08 | 2016-07-11 | 歐陸斯迪公司 | Dihydroetorphine |
| CN101780057B (en) * | 2009-01-21 | 2012-09-05 | 考司美德制药株式会社 | Transdermic absorption patch |
| GB201309654D0 (en) | 2013-05-30 | 2013-07-17 | Euro Celtique Sa | Method |
| EP3233081B1 (en) | 2014-12-19 | 2021-09-22 | Kindeva Drug Delivery L.P. | Transdermal drug delivery device including fentanyl |
Family Cites Families (20)
| 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 (en) * | 1990-05-02 | 1991-11-03 | Marian R. Appelt | Crosslinked pressure-sensitive adhesives tolerant of alcohol-based excipients used in transdermal delivery devices and method of preparing same |
| DE59203307D1 (en) * | 1991-06-10 | 1995-09-21 | Lohmann Therapie Syst Lts | NITROGLYCERIN PLASTER AND METHOD FOR THE PRODUCTION THEREOF. |
| US5762952A (en) * | 1993-04-27 | 1998-06-09 | Hercon Laboratories Corporation | Transdermal delivery of active drugs |
| EP0686958B1 (en) * | 1994-06-06 | 2003-10-29 | Canon Kabushiki Kaisha | DC compensation for interlaced display |
| US7150881B2 (en) * | 1997-06-26 | 2006-12-19 | Mylan Technologies, Inc. | Adhesive mixture for transdermal delivery of highly plasticizing drugs |
| 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 (en) | 1998-06-16 | 2000-01-07 | Mitsubishi Electric Corp | Picture tube device |
| US20020147366A1 (en) | 2000-07-07 | 2002-10-10 | Wiggins Michael S. | Alkoxylated tertiary and quaternary amine surfactants |
| US20020119187A1 (en) | 2000-09-29 | 2002-08-29 | Cantor Adam S. | Composition for the transdermal delivery of fentanyl |
| DE10110391A1 (en) * | 2001-03-03 | 2002-09-26 | Lohmann Therapie Syst Lts | Highly flexible nicotine transdermal therapeutic system with nicotine as active ingredient |
| MXPA03008349A (en) * | 2001-03-16 | 2004-10-15 | Johnson & Johnson | Transdermal patch for administering fentanyl. |
| DE10141650C1 (en) | 2001-08-24 | 2002-11-28 | Lohmann Therapie Syst Lts | Safe transdermal therapeutic system for administration of fentanyl or analogous analgesics, having matrix layer of carboxy group-free polyacrylate adhesive providing high permeation rate |
| TW536790B (en) * | 2002-06-12 | 2003-06-11 | Powerchip Semiconductor Corp | A manufacturing method of flash memory |
-
2003
- 2003-05-20 EP EP07018343.9A patent/EP1894563B2/en not_active Expired - Lifetime
- 2003-05-20 US US10/515,608 patent/US20060039960A1/en not_active Abandoned
- 2003-05-20 CN CN038119986A patent/CN1655772B/en not_active Expired - Lifetime
- 2003-05-20 CA CA2487123A patent/CA2487123C/en not_active Expired - Lifetime
- 2003-05-20 AU AU2003243896A patent/AU2003243896B2/en not_active Ceased
- 2003-05-20 MX MXPA04011759A patent/MXPA04011759A/en unknown
- 2003-05-20 WO PCT/DE2003/001635 patent/WO2003101433A1/en not_active Application Discontinuation
- 2003-05-20 EP EP03755897A patent/EP1509210A1/en not_active Ceased
- 2003-05-20 DE DE20321052U patent/DE20321052U1/en not_active Ceased
-
2008
- 2008-03-28 AT AT0019108U patent/AT10109U3/en not_active IP Right Cessation
- 2008-03-28 AT AT0019008U patent/AT10108U3/en not_active IP Right Cessation
-
2016
- 2016-02-17 US US15/045,267 patent/US20160158161A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1894563B2 (en) | 2022-04-27 |
| EP1509210A1 (en) | 2005-03-02 |
| US20160158161A1 (en) | 2016-06-09 |
| AT10109U3 (en) | 2009-07-15 |
| US20060039960A1 (en) | 2006-02-23 |
| AU2003243896B2 (en) | 2008-07-03 |
| AT10108U2 (en) | 2008-09-15 |
| CN1655772A (en) | 2005-08-17 |
| WO2003101433A1 (en) | 2003-12-11 |
| AU2003243896A1 (en) | 2003-12-19 |
| EP1894563A1 (en) | 2008-03-05 |
| EP1894563B1 (en) | 2010-10-27 |
| MXPA04011759A (en) | 2005-07-27 |
| AT10109U2 (en) | 2008-09-15 |
| CA2487123C (en) | 2011-10-18 |
| DE20321052U1 (en) | 2005-09-22 |
| AT10108U3 (en) | 2009-07-15 |
| CN1655772B (en) | 2010-05-26 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |
Effective date: 20230523 |