WO1996039136A1 - Formulation transdermique a base de ropinirole - Google Patents
Formulation transdermique a base de ropinirole Download PDFInfo
- Publication number
- WO1996039136A1 WO1996039136A1 PCT/EP1996/002435 EP9602435W WO9639136A1 WO 1996039136 A1 WO1996039136 A1 WO 1996039136A1 EP 9602435 W EP9602435 W EP 9602435W WO 9639136 A1 WO9639136 A1 WO 9639136A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ropinirole
- transdermal
- transdermal formulation
- formulation
- free base
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 32
- UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical compound CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 title claims description 32
- 238000009472 formulation Methods 0.000 title claims description 31
- 229960001879 ropinirole Drugs 0.000 title claims description 26
- 239000012458 free base Substances 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 11
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 230000004907 flux Effects 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 229940079593 drug Drugs 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000012528 membrane Substances 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 6
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229940088679 drug related substance Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XDXHAEQXIBQUEZ-UHFFFAOYSA-N Ropinirole hydrochloride Chemical compound Cl.CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 XDXHAEQXIBQUEZ-UHFFFAOYSA-N 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229960002349 ropinirole hydrochloride Drugs 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007916 tablet composition Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 239000008135 aqueous vehicle Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000010874 in vitro model Methods 0.000 description 2
- 239000002687 nonaqueous vehicle Substances 0.000 description 2
- 231100000435 percutaneous penetration Toxicity 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000011505 plaster Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 230000037317 transdermal delivery Effects 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 0 C*c1c(CC(N2)=O)c2ccc1 Chemical compound C*c1c(CC(N2)=O)c2ccc1 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000011340 continuous therapy Methods 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 230000000774 hypoallergenic effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229940068984 polyvinyl alcohol Drugs 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 238000010944 pre-mature reactiony Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000013464 silicone adhesive Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
-
- 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
Definitions
- the present invention relates to a transdermal formulation comprising 4-(2-di-n- proylaminoethyl)-2(3H)-indolone and for the use thereof in treating Parkinson's Disease.
- EP 0 299 602- A2 further discloses that other forms of administration may be considered for ropinirole and salts thereof, including parenteral, rectal and transdermal.
- a typical transdermal formulation is said to comprise a conventional aqueous or non-aqueous vehicle, for example, a cream, ointment lotion or paste in the form of a medicated plaster, patch or membrane. There is however no further guidance on suitable transdermal formulations or expected dosage for such formulations.
- a transdermal formulation offers the advantage of a more convenient mode of administration of the drug substance, thereby potentially enhancing patient compliance.
- drug substance is released in a more controlled fashion, over a prolonged period, offering potential therapeutic advantges.
- transdermal formulations able to provide a therapeutically useful amount of the drug may be prepared by using the free base form of the compound, in comparison to the hydrochloride salt preferred for tablet formulation.
- the present invention provides for a transdermal formulation comprising ropinirole (free base).
- Such formulations offer not only a more convenient method of administration but also possible therapeutic benefits and improved side effect profile.
- transdermal formulations are well known in the art (see for instance Percutaneous Absorption and Transdermal Therapy, K A Walters, March 1986; Pharmaceutical Dosage Forms and Drug Delivery Systems, (5th Ed.), H C. Ansel and N G. Popovich, Chapter 9, Lea and Febiger (1990), pages 307 to 320 and Sustained and Controlled Release Drug Delivery Systems, ed J R Robinson, Marcel Dekker Inc., New York (1978), pages 579 et seq.).
- Two main types of transdermal delivery devices are currentiy marketed and these are classified as matrix and membrane systems (Physicochemical Principles of Pharmacy, A.T. Florence and D. Attwood, 2nd Edition, Macmillan, 1993, page 331).
- the drug is dispersed in a release controlling matrix which consists either of a gel or an adhesive film.
- Membrane systems generally consist of a drug reservoir, a rate-controlling membrane and an adhesive layer. In both cases the active is dissolved or suspended in a vehicle which then forms an integral part of the delivery device.
- the drug substance may be dissolved or suspended in a liquid or a gel.
- Suitable vehicles include both aqueous and non-aqueous vehicles, for instance saline and saline/propylene glycol (1:1).
- a penetration enhancer may also be added, if appropriate.
- the transdermal formulation is provided in the form of a medicated plaster, patch or membrane, preferably a patch.
- the patch is between 10 and 50cm 2 , preferably between 20 and 40 cm 2 .
- the patch will be provided with a pharmaceutically accetable adhesive layer so that it can retained on the skin of the user.
- the adhesive effect of the layer will be reversible such that the patch will remain in place for the lifetime of the patch but still be easy for the Parkinson's Disease patient to apply and remove.
- ropinirole free base may be generated in situ in the transdermal formulation, from a suitable ropinirole salt such as ropinirole hydrochloride, suitably immediately prior to use.
- a suitable ropinirole salt such as ropinirole hydrochloride
- this may be achieved by including in the formulation a base which would be brought into contact with the ropinirole salt to effect formation of the free base.
- the salt and base are kept apart, to avoid premature reaction, for instance in a two compartment reservoir having a rupturable barrier between the two compartments.
- a preliminary evaluation of transdermal candidates is performed prior to incorporation in such a device.
- the most effective method is to determine drug penetration from suspensions or solutions using a human skin in vitro model, such as the Franz cell (Dematological Formulations: Percutaneous Abso ⁇ tion, B W Barry, Marcel Dekker (1983), page 245).
- the delivery profile will provide a steady rate delivery.
- a compartmentalised rate controlled device may be used.
- a suitable target skin flux will be in the range 5 to 25, preferably 10 to 15 ⁇ g/cm 2 hr.
- the amount of ropinirole administered through a transdermal formulauon according to the present invention will be selected so that it will provide an amount of ropinirole substantially similar to that obtained following conventional oral administration of a tablet formulation, that is substantially similar to that obtained following administration of between 0.1 and lOmg of ropinirole (expressed as the free base) three times a day, assuming about 50% bioavailablity.
- the transdermal formulation is provided in unit dose form.
- the transdermal formulation is provided in a range of dosage amounts, for instance to allow for titration of an individual patient's drug requirement.
- a suitable dose may be obtained by combining different strength formulations.
- the unit dose form will provide sufficient drug substance for a 24 hour period (including, if appropriate 'off time'), to permit once-a-day application of the formulation. Suitably such application may be in the evening.
- the transdermal formulation will be administered for a period of continuous therapy.
- Transdermal formulations according to the present invention will be of use in therapy, in particular treating Parkinson's Disease. Accordingly, in a further aspect, the present invention provides for the manufacture of a medicament comprising ropinirole (free base) adapted for a transdermal administration for use in treating Parkinson's Disease.
- the transdermal formulation may be used in patients in all stages of disease and/or as therapy after initial dose titration with a conventional tablet.
- Ropinirole hydrochloride (190gm), water (1.35L) and ammonia (160mL,SG 0.88) were added to a flask fitted with stirrer and nitrogen bleed. This mixture was then stirred at ambient for ca 2hours and then extracted with dichloromethane (lx500mL, lx 250mL, lx 200mL). All the organic extracts were combined, washed with brine (3x50mL) and dried over with magnesium sulphate (if free water was still present). Removal of the solvent by evaporation under reduced pressue gave a light brown solid (142gm, 85% yield).
- a typical patch comprising a membrane is as follows:
- a backing layer of aluminized plastic that is impermeable to ropinirole; drug reservoir containing ropinirole (30 to 60mg/ml) in a saline/propylene glycol (1:1) vehicle; ethylene- vinyl acetate copolymer membrane that is permeable to ropinirole; and a layer of hypoallergenic silicone adhesive; plus a protective peel strip covering the adhesive surface.
- a typical patch comprising a matrix is as follows:
- ropinirole as the free base
- a ropinirole salt for formulation into a transdermal delivery system was initially evaluated by determining drug penetration from suspensions or solutions using a human skin in vitro model.
- the in vitro percutaneous penetration method utilised saturated solutions of ropinirole hydrochloride and ropinirole free base.
- the in vitro set up consisted of modified Franz cells (Dematological Formulations: Percutaneous Absorption. B.W. Barry, Marcel Dekker, 1983, 245) with full thickness human abdominal skin and a receptor of 0.9% saline.
- the vehicles tested were ropinirole and its hydrochloride salt in aqueous 0.9% saline and aqueous 0.9% saline/propylene glycol (50:50). Samples were taken from the receptor at intervals and analysed for ropinirole content. From these results the concentration of ropinirole penetrating human skin with time could be determined.
- Penetration of the free base appears to be 20 fold better than the salt from the 0.9% saline vehicle and 40 fold better from the PG: saline vehicle.
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- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP96917499A EP0831810A1 (fr) | 1995-06-06 | 1996-06-04 | Formulation transdermique a base de ropinirole |
JP9500145A JPH11506462A (ja) | 1995-06-06 | 1996-06-04 | ロピニロールを含有してなる経皮製剤 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9511366.8 | 1995-06-06 | ||
GBGB9511366.8A GB9511366D0 (en) | 1995-06-06 | 1995-06-06 | Novel formulations |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996039136A1 true WO1996039136A1 (fr) | 1996-12-12 |
Family
ID=10775543
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1996/002435 WO1996039136A1 (fr) | 1995-06-06 | 1996-06-04 | Formulation transdermique a base de ropinirole |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0831810A1 (fr) |
JP (1) | JPH11506462A (fr) |
GB (1) | GB9511366D0 (fr) |
WO (1) | WO1996039136A1 (fr) |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19814084A1 (de) * | 1998-03-30 | 1999-10-14 | Lohmann Therapie Syst Lts | D2-Agonist enthaltendes transdermales therapeutisches System zur Behandlung des Parkinson-Syndroms und Verfahren zu seiner Herstellung |
WO2003011291A1 (fr) * | 2001-07-30 | 2003-02-13 | Hexal Ag | Systeme therapeutique transdermique (reservoir tts) pour utiliser du pramipexol et du ropinirol |
US7258871B2 (en) | 2000-10-20 | 2007-08-21 | Neurobiotec Gmbh | Combination of a transdermal therapeutic system and an oral and/or parenteral preparation containing dopamine agonists for the treatment of dopaminergic disease states |
WO2008005240A3 (fr) * | 2006-06-29 | 2008-05-08 | Jazz Pharmaceuticals | Compositions pharmaceutiques de ropinirole et leurs méthodes d'application |
WO2009082268A2 (fr) | 2007-12-21 | 2009-07-02 | Alla Chem, Llc | Ligands dalpha-adrénorécepteurs, de récepteurs de dopamine, de l'histamine, d'imidazoline et de sérotonine ainsi que leurs procédés d'utilisation |
WO2009112167A1 (fr) * | 2008-03-11 | 2009-09-17 | Lts Lohmann Therapie-Systeme Ag | Système thérapeutique transdermique avec membrane stabilisée |
WO2010024717A1 (fr) | 2008-08-22 | 2010-03-04 | Алла Xem, Ллс | Ligand possédant une gamme étendue d’activité pharmacologique, composition pharmaceutique, médicament et méthode de traitement |
EP2258355A1 (fr) * | 2008-02-27 | 2010-12-08 | Hisamitsu Pharmaceutical Co., Inc. | Patch |
US7927624B2 (en) | 2000-04-14 | 2011-04-19 | Jagotec Ag | Hydrophilic/lipophilic polymeric matrix dosage formulation |
CN102361639A (zh) * | 2009-04-24 | 2012-02-22 | 久光制药株式会社 | 内包贴附剂的包装袋、及贴附剂的保存方法 |
EP2438917A1 (fr) * | 2009-05-21 | 2012-04-11 | Hisamitsu Pharmaceutical Co., Inc. | Préparation transdermique |
WO2011132966A3 (fr) * | 2010-04-23 | 2012-04-12 | 아이큐어(주) | Préparation pour absorption transdermique |
CN103561737A (zh) * | 2011-05-31 | 2014-02-05 | 久光制药株式会社 | 含有罗匹尼罗的贴附剂及其包装体 |
US9155725B2 (en) | 2008-02-27 | 2015-10-13 | Hisamitsu Pharmaceutical Co., Inc. | Adhesive skin patch and packaged product |
US9155710B2 (en) | 2011-05-31 | 2015-10-13 | Hisamitsu Pharmaceutical Co., Inc. | Ropinirole-containing patch and package thereof |
US9186335B2 (en) | 2002-07-30 | 2015-11-17 | Ucb Pharma Gmbh | Hot melt TTS for administering rotigotine |
US9320728B2 (en) | 2013-06-28 | 2016-04-26 | Hisamitsu Pharmaceutical Co., Inc. | Method for producing patch, patch and package |
US9849095B2 (en) | 2011-12-01 | 2017-12-26 | Teikoku Seiyaku Co., Ltd. | Ropinirole-containing adhesive patch |
US10149834B2 (en) | 2011-12-01 | 2018-12-11 | Teikoku Seiyaku Co., Ltd. | Ropinirole-containing adhesive patch |
US10716763B2 (en) | 2015-04-15 | 2020-07-21 | Hisamitsu Pharmaceutical Co., Inc. | Transdermal patch containing ropinirole |
US20210169849A1 (en) * | 2019-04-17 | 2021-06-10 | Vici Health Sciences LLC | Liquid pharmaceutical compositions |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10338174A1 (de) | 2003-08-20 | 2005-03-24 | Lts Lohmann Therapie-Systeme Ag | Transdermale Arzneimittelzubereitungen mit Wirkstoffkombinationen zur Behandlung der Parkinson-Krankheit |
US10022336B2 (en) | 2012-11-30 | 2018-07-17 | Teikoku Seiyaku Co., Ltd. | Ropinirole-containing adhesive patch |
JP6373061B2 (ja) * | 2014-05-23 | 2018-08-15 | 帝國製薬株式会社 | 経皮投与製剤 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0299602A2 (fr) * | 1987-05-21 | 1989-01-18 | Smith Kline & French Laboratories Limited | L'emploi de dérivés de l'indolone pour la fabrication de médicaments pour le traitement du parkinsonisme |
-
1995
- 1995-06-06 GB GBGB9511366.8A patent/GB9511366D0/en active Pending
-
1996
- 1996-06-04 WO PCT/EP1996/002435 patent/WO1996039136A1/fr not_active Application Discontinuation
- 1996-06-04 JP JP9500145A patent/JPH11506462A/ja active Pending
- 1996-06-04 EP EP96917499A patent/EP0831810A1/fr not_active Withdrawn
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0299602A2 (fr) * | 1987-05-21 | 1989-01-18 | Smith Kline & French Laboratories Limited | L'emploi de dérivés de l'indolone pour la fabrication de médicaments pour le traitement du parkinsonisme |
Non-Patent Citations (3)
Title |
---|
"FORMES PHARMACEUTIQUES NOUVELLES", 1988, LAVOISIER, PARIS, XP002013798 * |
D.B. CALNE: "TREATMENT OF PARKINSON'S DISEASE", THE NEW ENGLAND JOURNAL OF MEDICINE, vol. 329, no. 14, 1993, pages 1021 - 1027, XP002013778 * |
H.C. ANSEL ET AL.: "TRANSDERMAL DRUG DELIVERY SYSTEMS, OINTMENTS, CREAMS, LOTIONS, AND OTHER PREPARATIONS", PHARMACEUTICAL DOSAGE FORMS AND DRUG DELIVERY SYSTEMS 5TH ED., CHAPTER 9, 1990, pages 307 - 320, XP002013779 * |
Cited By (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10322093B2 (en) | 1998-03-30 | 2019-06-18 | Ucb Biopharma Sprl | Method for producing a transdermal therapeutic system which contains a D2 agonist |
DE19814084A1 (de) * | 1998-03-30 | 1999-10-14 | Lohmann Therapie Syst Lts | D2-Agonist enthaltendes transdermales therapeutisches System zur Behandlung des Parkinson-Syndroms und Verfahren zu seiner Herstellung |
US6884434B1 (en) | 1998-03-30 | 2005-04-26 | 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 |
DE19814084B4 (de) * | 1998-03-30 | 2005-12-22 | Lts Lohmann Therapie-Systeme Ag | D2-Agonist enthaltendes transdermales therapeutisches System zur Behandlung des Parkinson-Syndroms und Verfahren zu seiner Herstellung |
US10251844B2 (en) | 1998-03-30 | 2019-04-09 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system and method of use thereof for treating parkinsonism |
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Also Published As
Publication number | Publication date |
---|---|
JPH11506462A (ja) | 1999-06-08 |
EP0831810A1 (fr) | 1998-04-01 |
GB9511366D0 (en) | 1995-08-02 |
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