US20050175678A1 - Device for the transdermal administration of a rotigotine base - Google Patents
Device for the transdermal administration of a rotigotine base Download PDFInfo
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- US20050175678A1 US20050175678A1 US10/517,157 US51715704A US2005175678A1 US 20050175678 A1 US20050175678 A1 US 20050175678A1 US 51715704 A US51715704 A US 51715704A US 2005175678 A1 US2005175678 A1 US 2005175678A1
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- matrix
- rotigotine
- polymer
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- silicon
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- 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
-
- 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
- A61K9/7069—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
Definitions
- the present invention relates to a matrix suitable for transdermal administering of rotigotine [( ⁇ )-5,6,7,8-tetrahydro-6-[propyl [2-(2-thienyl)ethyl]amino]-1-naphtol] that is free of solvents and dispergents and that comprises at least one matrix polymer and rotigotine base in a concentration above the solubility limit of the matrix polymer for rotigotine, wherein the portion of the rotigotine not dissolved in the matrix polymer is dispersed in the matrix polymer as amorphous particles with a maximum mean diameter of 30 ⁇ m.
- the invention relates to a planiform system for transdermal administering of rotigotine, that contains the above-described preferably silicon-based matrix supersaturated with rotigotine and a backing impermeable for the active substance.
- WO 94-07468 discloses a transdermal system that contains an active substance salt in a two-phase matrix.
- the two-phase matrix consists of a hydrophobic matrix polymer with a silicate dispersed therein to absorb the hydrophilic pharmaceutical substance salt, wherein hydrophobic solvents are additionally used.
- the matrix is produced by drying the dispersion at 70° C.
- the rotigotine content in the matrix is 2-5 weight percent.
- WO 99/49852 describes a Transdermal Therapeutic System (TTS) containing a contact adhesive system based on acrylate or silicon, in which rotigotine is present in free-base form.
- TTS Transdermal Therapeutic System
- the disclosed TTS allows therapeutically relevant flow rates of rotigotine through human skin.
- Rotigotine is only feebly soluble in hydrophobic polymers such as silicon, for example.
- hydrophobic polymers such as silicon, for example.
- additives to improve the solution characteristics of the rotigotine is recommended.
- hydrophilic polymers such as polyvinyl pyrrolidone (PVP), copolymers of vinyl pyrrolidone and vinyl acetate, polyethylene glycol polypropylene glycol, copolymers of ethylene and vinyl acetate as well as glycerin and its ester.
- WO 02/089778 and WO 02/089777 also describe a solvent-based transdermal system for administering rotigotine. According to WO 02/089778 and WO 02/089777, surface-active substances or amphiphilic substances are also added as crystallization inhibitor.
- FIG. 1 shows a microscope photo of amorphous rotigotine particles in a silicon matrix that was produced according to example of execution 2b (comparison example) in the solvent method without dispergents.
- FIG. 2 shows microscopic photos of amorphous rotigotine particles in a silicon matrix according to the invention that was produced according to example of execution 1 by “tempering” without dispergents.
- FIG. 3 shows the comparison of in vitro rotigotine flow rates that are achieved after applying on mouse skin a system according to the invention (Charge 20204071), a comparison charge (Charge 20204074) produced according to example of execution 2b in the solvent method without dispergents and a system described in WO 99/49852 (Charge 20107012).
- FIG. 4 shows the comparison of in vitro rotigotine flow rates that are achieved after applying on human skin a system according to the invention (Charge 20204071) and a system described in WO 99/49852 (Charge WE11682).
- FIG. 5 shows as an example the structure of a monolithic TTS with an active substance-containing matrix ( 1 ), a backing ( 2 ) impermeable to the active substance and a protective layer ( 3 ) removable before utilization.
- FIG. 6 shows a comparison of the in vitro penetration rates through mouse skin from the transdermal systems (Charge 20204071, tempered) according to the invention and from the comparative examples 2a (Charge 20107012) and 3 (Charge 20204071, non-tempered) after 12 months of storage.
- Rotigotine base is present as a solid in the form of crystals that are nearly insoluble in the solvents suitable for dissolving matrix polymers, e.g. hexane, ethyl acetate and toluol.
- solvents suitable for dissolving matrix polymers e.g. hexane, ethyl acetate and toluol.
- the rotigotine crystals are therefore first dissolved in solvents, e.g. ethanol and then added to the polymer phase, e.g. in hexane.
- solvents e.g. ethanol
- dispergents are used such as the hydrophilic polymers mentioned in WO 99/49852. If the dispergents are not added in this method as recommended, large islands of active substance may form ( FIG. 1 ). These then conceal the risk of skin irritation, recrystallization of the active substance, reduced adhesion of the adhesive matrix and fluctuation of the active substance charge.
- the rotigotine base is, for example stirred in crystalline form into a solution of a silicon polymer, e.g. an amino-resistant silicon contact adhesive, in heptane, toluol or ethyl acetate, the mixture is coated onto a foil, e.g. a siliconized polyester foil, and the solvent is removed by drying at 50° C. Then the matrix is heated (“tempered”) to a temperature above the melting point of rotigotine, i.e., above approx. 74° C. until the rotigotine crystals have melted. Finally, the matrix is cooled to room temperature. The rotigotine is then present in the form of amorphous particles or drops finely distributed in the silicon-based matrix.
- a silicon polymer e.g. an amino-resistant silicon contact adhesive, in heptane, toluol or ethyl acetate
- the mixture is coated onto a foil, e.g. a siliconized polyester foil, and
- the amorphous rotigotine particles are surprisingly finely distributed in the silicon matrix, with a maximum size of roughly 30-40 ⁇ m, but mostly smaller than 20 ⁇ m ( FIG. 2 ). Even after six months storage at room temperature, the amorphous rotigotine particles in the silicon matrix showed no tendency to recrystallize.
- the adding of additives to remove peroxide can also be dispensed with.
- the matrix also contains no anorganic silicates or skin penetration enhancers.
- the TTS according to the invention show no signs of rotigotine recrystallization or any change in particle size.
- in vitro release experiments with the TTS according to the invention showed an unchanged release profile comparable with the collidone-containing TTS produced according to example 2a.
- a crystalline, rotigotine-containing TTS produced according to example of execution 3 for which the step of heating above the melting point of rotigotine was dispensed with, provided a clearly lower active substance release.
- softeners typically in hot melting methods—to reduce the dynamic viscosity of matrix polymers can also be dispensed with, since the polymer is processed in the solvent method.
- An object of the invention is thus a matrix for transdermal administering of rotigotine [( ⁇ )-5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino)-1 -naphtol], containing a matrix polymer supersaturated with rotigotine base, characterized in that the portion of the rotigotine not dissolved in the matrix polymer is dispersed in the matrix polymer as amorphous particles with a maximum mean diameter of 30 ⁇ m and the matrix is free of solvents, crystallization inhibitors and dispergents.
- a further object of the invention is a matrix containing rotigotine [( ⁇ )-5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphtol] and consisting of
- the matrix according to the invention generally contains at least 60 weight percent, preferably 70-95 weight percent, and particularly preferably 80-91 weight percent matrix polymer, each relative to the matrix weight.
- the matrix polymer is a silicon, preferably an amino-resistant silicon or a silicon mixture.
- a further object of the invention is thus a matrix containing rotigotine [( ⁇ )-5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphtol] and consisting of
- matrix is understood to mean a pharmaceutical formula that comprises at least one matrix polymer and that can form a disperse system.
- rotigotine base is understood to mean that less than 5 weight percent, preferably less than 2 weight percent, and particularly preferably less than 1 weight percent of the rotigotine is present in salt form;
- particles is understood to mean microscopically visible rotigotine accumulations, e.g. in drop form, in the matrix.
- mean diameter is understood to the mean the average value of all diameters (in the dimensions x, y, z, respectively) of the rotigotine particles present in a given matrix. This can be determined by examining the rotigotine-containing matrix with a microscope and analyzing the image with the Nikon LuciaDi software.
- matrix supersaturated with rotigotine is understood to mean that at least a portion of the rotigotine is not in the form dissolved in the polymer but rather dispersed as particles in the matrix.
- matrix polymer is understood to mean the polymers common for a pharmaceutical expert for producing transdermal forms of medicine. Examples of this are silicons, ethylvinyl acetates (EVA), styrol block copolymers (SXS), acrylates and methacrylates, polyurethanes, vinyl acetates and gums, in particular polyolefines and polyterpenes, e.g. polyisobutylenes, polybutadienes, neoprenes or polyisoprenes as well as suitable mixtures of these matrix polymers.
- EVA ethylvinyl acetates
- SXS styrol block copolymers
- acrylates and methacrylates polyurethanes
- vinyl acetates and gums in particular polyolefines and polyterpenes, e.g. polyisobutylenes, polybutadienes, neoprenes or polyisoprenes as well as suitable mixtures of these matrix
- silicon-based matrix is understood to mean a matrix that contains at least 60 weight percent, preferably 70-95 weight percent, and particularly preferably 80-91 weight percent silicon, relative to the matrix weight.
- matrix polymers are used in which rotigotine has a solubility of less than 5 weight percent, preferably less than 3 weight percent and particularly preferably less than 1 weight percent.
- the matrix supersaturated with rotigotine can be used for processing in various galenic forms of medicine.
- the rotigotine-containing matrix can be designed as an adhesive (self-adhesive) or non-adhesive matrix.
- the amorphous rotigotine particles are present preferably dispersed in a self-adhesive matrix, particularly preferably in a self-adhesive silicon contact adhesive matrix.
- Preferred silicon contact adhesives to use in the self-adhesive silicon contact adhesive matrix are amino-resistant, pressure-sensitive polyorganosiloxane adhesives.
- Silicon contact adhesives are in most cases polydimethyl siloxanes, but in principle instead of methyl groups other organic residues, such as ethyl or phenyl groups, can also be present.
- Amino-resistant silicon contact adhesive are generally distinguished in that they contain no or only few free silanol functions, because the Si—OH groups were alkalized. Such adhesives are described in the patent EP 180 377.
- Particularly preferable adhesives are condensates or mixtures of silicon resins and polyorganosiloxanes, as described in US RE 35 474, for example.
- Suitable polyorganosiloxane adhesives are commercially available from Dow Corning as so-called BIO-PSA contact adhesives. Particularly suitable are contact adhesives that are marketed by Dow Corning under the designation Bio-PSA 7-4201 and Bio-PSA 7-4301, as Well as suitable mixtures of these adhesives. These mixtures of silicon adhesives with strong and medium tack, in particular mixtures in Bio-PSA 7-4201 to Bio-PSA 7-4301 proportions of 40:60 to 60:40, are distinguished by a particularly favorable adhesion/ cohesion balance.
- the active substance concentration of the matrix according to the invention is not subject to the method-related limitations like the matrices produced in the solvent method according to the state of the art.
- the active substance concentration in the matrix can be between 1 and roughly 40 weight percent relative to the total weight of the matrix, wherein rotigotine concentrations between 5 and 30 weight percent and particularly between 7 and 25 weight percent are preferred.
- a rotigotine concentration in the matrix of at least 15 weight percent, and particularly of at least 20 weight percent, is preferred.
- Antioxidants are added, preferably in a total concentration of up to 2 weight percent, preferably 0.05-0.5 weight percent (relative to the matrix weight).
- Preferred examples are alpha-tocopherol, ascorbyl palmitate and mixtures thereof.
- the matrix according to the invention consists of
- the size distribution of the rotigotine particles in the preferably silicon-based matrix supersaturated with rotigotine should be as uniform as possible, wherein the mean diameter should preferably be below 25 ⁇ m, and particularly preferably below 20 ⁇ m.
- the matrix according to the invention is a component of a system, in particular a planiform system for transdermal administering of rotigotine, wherein the system can have further components such as, for example, a protective layer, a backing, further polymer layers and/or a membrane controlling the active substance delivery.
- the system according to the invention is equipped as a so-called monolithic plaster, i.e., it consists of a backing ( 2 ) impermeable to the active substance, a self-adhesive, preferably silicon-based matrix ( 1 ) supersaturated with rotigotine and into which the free base of rotigotine is dispersed in amorphous form and which contains no solvent, and a layer ( 3 ) that can be removed before applying on the patient's skin, as illustrated in FIG. 5 .
- a so-called monolithic plaster i.e., it consists of a backing ( 2 ) impermeable to the active substance, a self-adhesive, preferably silicon-based matrix ( 1 ) supersaturated with rotigotine and into which the free base of rotigotine is dispersed in amorphous form and which contains no solvent, and a layer ( 3 ) that can be removed before applying on the patient's skin, as illustrated in FIG. 5
- the rotigotine can also be present in a nonadhesive, supersaturated, preferably silicon-based matrix.
- the planiform system can then have an additional active substance-free adhesive layer or a so-called “overtape”.
- An object of the invention is thus a planiform system for transdermal administering of rotigotine [( ⁇ )-5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphtol], containing a rotigotine-containing matrix layer and a backing impermeable to the active substance, characterized in that the matrix layer consists of
- the planiform system is structured as a monolithic system and contains a self-adhesive rotigotine-containing matrix layer based on an amino-resistant silicon contact adhesive.
- the surface of the system can be between 5 and approx. 80 cm 2 large, is preferably between 10 and 60 cm 2 and particularly preferably between 20 and 40 cm 2 .
- the thickness of the matrix layer in the systems according to the invention is typically in the 40-300 ⁇ m range, wherein matrix thicknesses of 50-200 ⁇ m and particularly of 70-150 ⁇ m are preferred. This results in a preferred matrix weight of approx. 40-200 g/m 2 .
- Preferred rotigotine concentrations in the matrix layer of the system are between 5 and 30 weight percent and particularly preferably between 7 and 25 weight percent, relative to the total weight of the matrix. If the system is intended for an application of more than 5 days, as a rule concentrations, of the rotigotine of more than 15 weight percent, and preferably more than 20 weight percent, are preferred. Typical concentrations for 7-day plasters are 20-30 weight percent.
- the charge level of the matrix in the system according to the invention is basically between 0.1 and 9 mg rotigotine/cm 2 matrix surface.
- the preferred charge level is in the 0.3-6 mg rotigotine/cm 2 range.
- a rotigotine charge between 0.3 and 1.5 mg rotigotine/cm 2 is preferred, and for 7-day systems one of 2.5-6.0 mg/cm 2 .
- the following table shows active substance concentrations and matrix weight of the monolithic plaster used for the skin permeation experiments ( FIG. 2, 3 ).
- Matrix Cumulative flow Cumulative flow Charge Production Active substance weight through human skin through mouse skin number condition concentration (g/m 2 ) ⁇ m/cm 2 /72 h ⁇ m/cm 2 /72 h 20204071 Tempered 90° C., 8.87 weight percent 129 850 1030 75 min. 20107012
- Solvent method 1 9 weight percent 110 n.d. 1080 WE 11682
- the size distribution of the rotigotine particles in the silicon-based matrix of the systems according to the invention should be as uniform as possible and on the average below 30 ⁇ m, wherein the mean diameter is preferably below 25 ⁇ m, and particularly preferably below 20 ⁇ m.
- a given matrix layer there should preferably be no particles whose diameter in the largest dimension (x, y, z) is greater than 90% of the thickness of the respective matrix layer.
- the backing onto which the matrix mass of the system according to the invention is spread should be inert for the contents of the matrix and impermeable to rotigotine.
- Suitable materials are, for example, polyesters, polyamides, polyethylenes, polypropylene, polyurethanes, PVC or combinations of these materials.
- the foils can be siliconized and/or provided with an aluminum layer. The thickness typically varies between 10 and 100 ⁇ m and is preferably between 20 and 40 ⁇ m.
- the system also preferably contains a protective layer or foil that is removed immediately before using the system, i.e., before applying on the skin.
- This protective layer can, for example, be of polyester, polyethylene or polypropylene. This layer can additionally be coated with aluminum or fluoropolymers. The thickness of this protective layer is typically between 30 and 200 ⁇ m.
- the protective layer preferably consists of two separate foils the ends of which may overlap. Corresponding designs are known from conventional plasters.
- Rotigotine is a dopamine agonist.
- the matrices and systems according to the invention are thus particularly suitable for treating illnesses that are associated with a disturbed dopamine metabolism.
- An object of the invention is thus the use of a system according to the invention or a matrix according to the invention in a drug for treating Morbus Parkinson, Restless Leg or depression.
- the preferably silicon-based matrix supersaturated with rotigotine can be produced simply in that the rotigotine base in crystalline form is stirred into a solution of a corresponding matrix polymer, the solvent is removed by drying at 50° C. and finally, the solvent-free matrix is heated (“tempered”) to a temperature above the melting point of rotigotine, i.e., above approx. 74° C. until the rotigotine crystals have melted. Subsequently, the matrix is cooled to room temperature, in such a way that the rotigotine is finally present in the form of amorphous particles or drops in the matrix according to the invention.
- the cooling step is preferably carried out “passively”, i.e., the rotigotine-containing matrix is exposed to room temperature; an additional cooling is not necessary, as a rule.
- An object of the invention is thus a method for producing a matrix for transdermal administering of rotigotine, characterized by the consecutive steps:
- step (c) the removal of the solvent and the melting of the rotigotine can be achieved by continually raising the temperature, e.g. from 50° C. to 90° C., in a dry lane.
- step (c) the solvent can first be removed in a step (c1) at a temperature of 40-60° C. and the solvent-free matrix can then be heated in a step (c2) to at least 74° C. until the rotigotine has melted.
- Suitable process temperatures for the melting of rotigotine are, for example, 75-120° C., preferably 80-100° C., and particularly preferably 90° C.
- the rotigotine-containing polymer mass created during the above-described matrix production in step (b) is spread out on a suitable foil, e.g. a polyester foil, before removal of the solvent.
- An object of the invention is thus a method for producing a planiform system for transdermal administering of rotigotine, comprising a rotigotine-containing matrix, characterized by the consecutive steps:
- step (d) removal of the solvent and the melting of the rotigotine according to step (d) can take place either by continually raising the temperature, e.g. from 50° C. to 90° C. or, on the other hand, in stages in two separate steps (d1) and (d2), as already described further above.
- the usually needle-shaped rotigotine crystals can be reduced to the desired size, e.g. 50 ⁇ m long, if necessary, by suitable pretreatment, e.g. by grinding or pounding and subsequent sifting.
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Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/020,414 US8545872B2 (en) | 2002-12-30 | 2011-02-03 | Device for the transdermal administration of a rotigotine base |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10261696.5 | 2002-12-30 | ||
DE2002161696 DE10261696A1 (de) | 2002-12-30 | 2002-12-30 | Vorrichtung zur transdermalen Verabreichung von Rotigotin-Base |
PCT/EP2003/014902 WO2004058247A1 (de) | 2002-12-30 | 2003-12-24 | Vorrichtung zur transdermalen verabreichung von rotigotin-base |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US13/020,414 Continuation US8545872B2 (en) | 2002-12-30 | 2011-02-03 | Device for the transdermal administration of a rotigotine base |
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Publication Number | Publication Date |
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US20050175678A1 true US20050175678A1 (en) | 2005-08-11 |
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Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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US10/517,157 Abandoned US20050175678A1 (en) | 2002-12-30 | 2003-12-24 | Device for the transdermal administration of a rotigotine base |
US13/020,414 Expired - Fee Related US8545872B2 (en) | 2002-12-30 | 2011-02-03 | Device for the transdermal administration of a rotigotine base |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
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US13/020,414 Expired - Fee Related US8545872B2 (en) | 2002-12-30 | 2011-02-03 | Device for the transdermal administration of a rotigotine base |
Country Status (22)
Country | Link |
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US (2) | US20050175678A1 (de) |
EP (1) | EP1490052B1 (de) |
JP (1) | JP5134187B2 (de) |
KR (1) | KR100875532B1 (de) |
CN (1) | CN1731995B (de) |
AT (1) | ATE363274T1 (de) |
AU (1) | AU2003294007B2 (de) |
BR (1) | BR0311637A (de) |
CA (1) | CA2485656C (de) |
CY (1) | CY1108084T1 (de) |
DE (2) | DE10261696A1 (de) |
DK (1) | DK1490052T3 (de) |
ES (1) | ES2285234T3 (de) |
HK (1) | HK1088227A1 (de) |
IL (1) | IL165131A (de) |
MX (1) | MXPA04012151A (de) |
NO (1) | NO335200B1 (de) |
PL (1) | PL215307B1 (de) |
PT (1) | PT1490052E (de) |
RU (1) | RU2340339C2 (de) |
WO (1) | WO2004058247A1 (de) |
ZA (1) | ZA200408523B (de) |
Cited By (40)
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US20030166709A1 (en) * | 2000-08-24 | 2003-09-04 | Stephan Rimpler | Novel pharmaceutical compositions administering n-0923 |
US20040048779A1 (en) * | 2002-05-06 | 2004-03-11 | Erwin Schollmayer | Use of rotigotine for treating the restless leg syndrome |
US20040081683A1 (en) * | 2002-07-30 | 2004-04-29 | Schacht Dietrich Wilhelm | Transdermal delivery system |
US20040116537A1 (en) * | 2002-12-02 | 2004-06-17 | Li Gai Ling | Iontophoretic delivery of rotigotine for the treatment of Parkinson's disease |
US20040137045A1 (en) * | 2002-07-30 | 2004-07-15 | Armin Breitenbach | Hot-melt TTS for administering Rotigotine |
US20050033065A1 (en) * | 1998-03-30 | 2005-02-10 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system which contains a D2 agonist and which is provided for treating parkinsonism, and a method for the production thereof |
US20050142175A1 (en) * | 2003-12-12 | 2005-06-30 | Thomas Langguth | Transdermal delivery of hormones without the need of penetration enhancers |
US20050197385A1 (en) * | 2004-02-20 | 2005-09-08 | Schwarz Pharma Ag | Use of rotigotine for treatment or prevention of dopaminergic neuron loss |
US20050260254A1 (en) * | 2002-07-30 | 2005-11-24 | Schwarz Pharma | Hot melt tts for administering rotigotine |
US20060246122A1 (en) * | 2005-05-02 | 2006-11-02 | Thomas Langguth | Solid transdermal therapeutic system with UV absorber |
US20060251707A1 (en) * | 2003-02-21 | 2006-11-09 | Jochen Schumacher | Uv stable transdermal therapeutic plaster |
US20070093546A1 (en) * | 2003-07-26 | 2007-04-26 | Srz Properties, Inc. | Use of rotigotine for the treatment of depression |
US20070191470A1 (en) * | 2004-03-24 | 2007-08-16 | Dieter Scheller | Use of rotigotine for treating and preventing parkinson's plus syndrome |
US20070197480A1 (en) * | 2003-12-18 | 2007-08-23 | Srz Properties, Inc. | (S)-2-N-Propylamino-5-Hydroxytetralin As A D3-Agonist |
US20080008748A1 (en) * | 2006-06-22 | 2008-01-10 | Bettina Beyreuther | Method for treating pain using a substituted 2-aminotetralin compound |
US20080146622A1 (en) * | 2003-12-24 | 2008-06-19 | Srz Properties, Inc. | Use Of Substituted 2-Aminotetralins For Preventive Treatment Of Parkinson's Disease |
US20080226698A1 (en) * | 2007-03-16 | 2008-09-18 | Mylan Technologies, Inc. | Amorphous drug transdermal systems, manufacturing methods, and stabilization |
US20080274061A1 (en) * | 2007-05-04 | 2008-11-06 | Erwin Schollmayer | Method for Treating a Restless Limb Disorder |
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CN113453676A (zh) | 2019-02-15 | 2021-09-28 | 久光制药株式会社 | 罗替戈汀稳定化方法 |
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CN110200950B (zh) * | 2012-11-22 | 2023-03-10 | Lts勒曼治疗系统股份公司 | 用于罗替戈汀经皮施用的多天型贴剂 |
US11033723B2 (en) | 2013-07-03 | 2021-06-15 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system comprising an electronic component |
US11426359B2 (en) | 2014-05-20 | 2022-08-30 | Lts Lohmann Therapie-Systeme Ag | Method for adjusting the release of active agent in a transdermal delivery system |
US11633367B2 (en) | 2014-05-20 | 2023-04-25 | Lts Lohmann Therapie-Systeme Ag | Transdermal delivery system containing rotigotine |
US11752110B2 (en) | 2014-05-20 | 2023-09-12 | Lts Lohmann Therapie-Systeme Ag | Transdermal delivery system including an interface mediator |
US11607394B2 (en) | 2017-12-19 | 2023-03-21 | Hisamitsu Pharmaceutical Co., Inc. | Rotigotine-containing patch |
WO2019234662A1 (en) * | 2018-06-07 | 2019-12-12 | Nal Pharmaceutical Group Limited | Transdermal drug delivery system containing rotigotine |
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