WO2014188329A4 - Transdermal extended dosing of pramipexole for neurological disorders - Google Patents

Transdermal extended dosing of pramipexole for neurological disorders Download PDF

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Publication number
WO2014188329A4
WO2014188329A4 PCT/IB2014/061545 IB2014061545W WO2014188329A4 WO 2014188329 A4 WO2014188329 A4 WO 2014188329A4 IB 2014061545 W IB2014061545 W IB 2014061545W WO 2014188329 A4 WO2014188329 A4 WO 2014188329A4
Authority
WO
WIPO (PCT)
Prior art keywords
matrix layer
pramipexole
transdermal therapeutic
therapeutic system
active ingredient
Prior art date
Application number
PCT/IB2014/061545
Other languages
French (fr)
Other versions
WO2014188329A3 (en
WO2014188329A2 (en
Inventor
Abhijit Mukund Deshmukh
Akhilesh DIXIT
Prasanna Kumar
Vikram BINDRA
Original Assignee
Mylan, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mylan, Inc. filed Critical Mylan, Inc.
Priority to EP14801302.2A priority Critical patent/EP2999444A4/en
Priority to US14/893,020 priority patent/US9682068B2/en
Publication of WO2014188329A2 publication Critical patent/WO2014188329A2/en
Publication of WO2014188329A3 publication Critical patent/WO2014188329A3/en
Publication of WO2014188329A4 publication Critical patent/WO2014188329A4/en

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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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/428—Thiazoles condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/02—Adhesive plasters or dressings
    • A61F13/0246—Adhesive plasters or dressings characterised by the skin adhering layer
    • A61F13/025—Adhesive plasters or dressings characterised by the skin adhering layer having a special distribution arrangement of the adhesive
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/02—Adhesive plasters or dressings
    • A61F13/0259—Adhesive plasters or dressings characterised by the release liner covering the skin adhering layer
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/02—Adhesive plasters or dressings
    • A61F13/0276—Apparatus or processes for manufacturing adhesive dressings or bandages
    • A61F13/0283—Apparatus or processes for manufacturing adhesive dressings or bandages for making adhesive or cohesive tape or fabrics therefor, e.g. coating or mechanical treatments
    • 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
    • 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
    • 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
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/02—Adhesive plasters or dressings
    • A61F13/0276—Apparatus or processes for manufacturing adhesive dressings or bandages
    • A61F2013/0296—Apparatus or processes for manufacturing adhesive dressings or bandages for making transdermal patches (chemical processes excluded)

Abstract

This disclosure relates to a transdermal therapeutic system (TTS) containing pramipexole or related compounds and methods of making the system as well as its use in administering such compounds as a single dose over an extended period, for example, one week. The system comprises an acrylic-based or silicone-based matrix layer containing pramipexole at concentrations of at least about 5 wt.% of the matrix, which is resistant to crystallizing and discoloration of the active ingredient even when stored over long periods.

Claims

1 AMENDED CLAIMS received by the International Bureau on 04 February 2015 (04.02.2015) What is claimed is:
1. A transdermal therapeutic system (TTS) for the administration of one or more active ingredients selected from the group consisting of pramipexole, pharmaceutically acceptable pramipexole salts, and pharmaceutically acceptable pramipexole derivatives, the system comprising:
(i) a substantially active-ingredient-impermeable backing layer,
(ii) at least one matrix layer which contains from about 5% to about 10% w/w active ingredient(s), and
(iii) a substantially impermeable protective release liner layer which releasably contacts the matrix layer or another adhesive layer;
wherein 1) the matrix layer comprises an adhesive selected from acrylate -based adhesive and silicone-based adhesive, 2) the transdermal therapeutic system provides a therapeutically effective administration of the active ingredient(s), at a flux rate ranging from about 1 μg/ cm2/hr to about 13 μg/ cm2/hr for at least 48 hours after treatment is initiated, and 3) the matrix layer is color-stable and lacks crystal growth of the active ingredient, over an extended storage period of at least one of 30 or more days, 90 or more days, and 180 or more days; and
wherein the matrix layer contains less than about 1 wt.% pramipexole-related impurities after two months of storage at about 40°C.
2. The transdermal therapeutic system of claim 1 wherein the active-ingredient- containing matrix layer contains from about 5.5% to about 7% w/w active ingredient(s) . 2
3. The transdermal therapeutic system of claim 1 wherein the active-ingredient- containing matrix layer contains less than about 0.5 wt.% pramipexole-related impurities after two months of storage at about 40°C.
4. The transdermal therapeutic system of claim 1 wherein the active-ingredient- containing matrix layer provides a therapeutically effective flux rate ranging from about 1 g/cm2/hr to about 13 g/cm2/hr between the 48th hour and 168th hour after treatment is initiated.
5. The transdermal therapeutic system of claim 1 wherein the active-ingredient- containing matrix layer contains from about 5.5% to about 7% w/w active ingredient(s) and provides a therapeutically effective flux profile ranging from about 1 μg/ cm2/hr to about 6 μg/ cm2/hr between the 96th hour and 168th hour after treatment is initiated.
6. The transdermal therapeutic system of claim 1 wherein the active-ingredient- containing matrix layer provides a therapeutically effective flux profile ranging from about 1.2 μg/cm2/hr to about 5.0 μg/cm2/hr 168 hours after treatment is initiated.
7. The transdermal therapeutic system of claim 1 wherein the active ingredient comprises pramipexole free base. 3
8. The transdermal therapeutic system of claim 1 wherein the active ingredient comprises one or more salts pramipexole comprising reaction products of pramipexole or a pramipexole derivative and an acid.
9. The transdermal therapeutic system of claim 1, wherein the matrix layer is self- adhesive.
10. The transdermal therapeutic system of claim 1, wherein the matrix layer comprises an acrylate -based adhesive comprising polyacrylate lacking a carboxylic acid functional group.
11. The transdermal therapeutic system of claim 10, wherein the matrix layer comprises a polymer material free of solubilizers and/or crystal growth inhibitors.
12. The transdermal therapeutic system of claim 10, wherein the matrix layer comprises 0 wt.% to about 20 wt.% of a solubilizer and/ or crystal growth inhibitor.
13. The transdermal therapeutic system of claim 10, wherein the matrix layer comprises from about 2.5 wt.% to about 17.5 wt.% of a solubilizer and/ or crystal growth inhibitor.
14. The transdermal therapeutic system of claim 10, wherein the matrix layer comprises about 10 wt.% of a solubilizer and/ or crystal growth inhibitor. 4
15. The transdermal therapeutic system of claim 12, wherein the solubilizer and/or crystal growth inhibitor is selected from the group consisting of optionally saturated and/or unsaturated fatty alcohols each containing from 8 to 18 carbon atoms; tea tree oil; saturated and/ or unsaturated cyclic ketones; alkyl methyl sulfoxides; saturated and/ or unsaturated fatty acids each containing from 8 to 18 carbon atoms; esters and salts thereof; natural vitamin E (Copherol® F1300); synthetic vitamin E and/or vitamin E derivatives; sorbitan fatty acid esters and/or ethoxylated sorbitan fatty acid esters; azones (laurocapram); 1-alkylpyrrolidone; polyvinylpyrrolidone; block copolymers of polyethylene glycol and dimethylsiloxane with a cationic group at one end; polysiloxanes; polyoxyethylene-10-stearyl ether; mixture of polyoxyethylene-10-stearyl ether and glyceryl dilaurate; dodecyl-2-(N,N-dimethylamino)-propanol tetradecanoate and/or dodecyl-2- (Ν,Ν-dimethylamino) -propionate; N-acetylprolinate esters with >8 carbon atoms; non- ionic surfactants, for example lauryl ethers and/or esters of polyoxyethylene; dimethyl (arylimino)sulfuran; mixture of oleic acid analogues and propylene glycol; mixture of octyl salicylate, isopropyl myristate, isopropyl palmitate, octylmethoxy cinnamate and laurocapram or a mixture of individual components; phospholipids; highly dispersed silicon dioxide (Aerosil®); polyoxyethylene-7-glycerol monococoate (Cetiol® HE); 2-octyldodecanol (Eutanol® G) or a mixture of various individual components.
16. The transdermal therapeutic system of claim 12, wherein the solubilizer and/or crystal growth inhibitor is polyvinylpyrrolidone. 5
17. A method for preparing a transdermal therapeutic system comprising a matrix layer containing pramipexole free base as an active ingredient wherein the matrix layer contains less than about 1 wt.% pramipexole-related impurities after two months of storage at about 40°C; said method comprising:
i) providing an active-ingredient containing matrix layer by:
1) forming a mixture comprising a) said active ingredient, b) a solvent selected from methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol and tert- butanol, acetone, pentane, hexane, heptane, ethyl acetate, isopropanol, toluene, xylene, 2,4-pentanedione, and water, and c) an optional solubilizer and/or crystal growth inhibitor;
2) dissolving the mixture to provide a dissolved mixture;
3) combining the dissolved mixture with a matrix forming ingredient to form a pramipexole-containing matrix precursor mixture; and
4) optionally degassing the matrix precursor mixture to provide a degassed matrix precursor mixture;
ii) coating one side of a release liner film with the matrix precursor mixture or optionally degassed matrix precursor mixture to produce said matrix layer, wherein said matrix layer contains from about 5% to about 10% w/w active ingredient(s); and
iii) laminating a backing film to the coated side of the release liner film.
18. The method of claim 17 wherein the solvent comprises ethanol, the dissolving step comprises sonication, the optional solubilizer and/or crystal growth inhibitor comprises polyvinylpyrrolidone, and the matrix forming ingredient comprises an adhesive selected from acrylate-based adhesive and silicone-based adhesive. 6
19. The method of claim 18 wherein the adhesive comprises polyacrylate lacking a carboxylic acid functional group.
20. The method of claim 17 wherein the optional solubilizer and/or crystal growth inhibitor comprises polyvinylpyrrolidone.
21. The method of claim 17 wherein the adhesive comprises silicone-based adhesive, silicone oil, and colloidal silicon dioxide.
22. A method for administering pramipexole to a human subject in need thereof, which method comprises:
i) providing a transdermal dosage form comprising a therapeutically effective amount of active ingredient pramipexole or a pharmaceutically acceptable salt thereof in at least one matrix layer which contains from about 5% to about 10% w/w active ingredient(s), and further
wherein 1) the matrix layer comprises an adhesive selected from acrylate -based adhesive and silicone-based adhesive, 2) the transdermal therapeutic system provides a therapeutically effective administration of the active ingredient(s), at a flux rate ranging from about 1 μg/ cm2/hr to about 13 μg/ cm2/hr for at least 48 hours after treatment is initiated, and 3) the matrix layer is color-stable and lacks crystal growth of the active ingredient, over an extended storage period of at least one of 30 or more days, 90 or more days, and 180 or more days; and 7
wherein the matrix layer contains less man auoui i piamipexoie-ieiaieu impurities after two months of storage at about 40°C; and
ii) applying the dosage form onto an area of skin of the subject in an amount sufficient to provide a therapeutic concentration of pramipexole in the bloodstream of the subject.
23. The method according to claim 22, wherein the human subject is in need of pramipexole to treat a neurological disorder.
24. The method according to claim 23, wherein the human subject is in need of pramipexole to treat a condition selected from the group consisting of Parkinson's Disease, Restless Legs Syndrome, Tourette's Syndrome, Chronic Tic Disorder, Essential Tremor, and Attention Deficit Hyperactivity Disorder.
25. The method according to claim 22, which comprises applying up to about 10 grams of the dosage form daily to a skin surface area of about 50 to about 500 cm2.
26. The method according to claim 22, wherein the method comprises applying the dosage form in a weekly single dose.
27. A method for preparing a transdermal therapeutic system comprising a matrix layer containing pramipexole free base as an active ingredient, wherein the matrix layer contains less than about 1 wt.% pramipexole-related impurities after two months of storage at about 40°C; said method comprising : 8
i) providing an active-ingredient containing mauix layer uy:
1) forming a mixture comprising a) said active ingredient, b) a solvent and/or dispersant selected from methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso- butanol and tert-butanol, acetone, pentane, hexane, heptane, ethyl acetate, isopropanol, toluene, xylene, 2,4-pentanedione, and water, and c) an optional solubilizer and/ or crystal growth inhibitor;
2) dissolving and/or dispersing the mixture to provide a dissolved and/or dispersed mixture;
3) combining the dissolved and/or dispersed mixture with a matrix forming ingredient to form a pramipexole-containing matrix precursor mixture; and
4) optionally degassing the matrix precursor mixture to provide a degassed matrix precursor mixture;
ii) coating one side of a release liner film with the matrix precursor mixture or optionally degassed matrix precursor mixture to produce said matrix layer, wherein said matrix layer contains from about 5% to about 10% w/w active ingredient(s); and
iii) laminating a backing film to the coated side of the release liner film.

Statement under Article 19(1)

In the International Search Report and Written Opinion, claims 2 and 3 were determined to possess novelty, an inventive step, and industrial applicability. The Examiner acknowledged that the prior art fails to teach a transdermal system with an active-ingredient containing matrix layer containing from about 5 percent to about 10 percent w/w active ingredient(s), and less than about 1 wt percent pramipexole-related impurities after two months of storage at about 40 degrees Celsius. Accordingly, amended claims 1, 17, and 22, as well as replacement claim 27, recite a matrix layer containing from about 5% to about 10% w/w active ingredient(s); and containing less than about 1 wt.% pramipexole-related impurities after two months of storage at about 40° C.

Therefore, claims 1, 17, 22, and 27, as amended, each possess novelty, an inventive step, and industrial applicability.

PCT/IB2014/061545 2013-05-20 2014-05-19 Transdermal therapeutic system for extended dosing of pramipexole in treating neurological disorders WO2014188329A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP14801302.2A EP2999444A4 (en) 2013-05-20 2014-05-19 Transdermal extended dosing of pramipexole for neurological disorders
US14/893,020 US9682068B2 (en) 2013-05-20 2014-05-19 Transdermal therapeutic system for extended dosing of pramipexole in treating neurological disorders

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1787MU2013 2013-05-20
IN1787/MUM/2013 2013-05-20

Publications (3)

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WO2014188329A2 WO2014188329A2 (en) 2014-11-27
WO2014188329A3 WO2014188329A3 (en) 2015-03-12
WO2014188329A4 true WO2014188329A4 (en) 2015-04-30

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EP (1) EP2999444A4 (en)
WO (1) WO2014188329A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016103956A1 (en) * 2014-12-25 2016-06-30 ニプロ株式会社 Preparation for transdermal administration
US9980921B2 (en) 2016-06-30 2018-05-29 Taho Pharmaceuticals Ltd. Transdermal delivery system containing methylphenidate or its salts and methods thereof
CN114796163A (en) * 2016-10-07 2022-07-29 全崴生技股份有限公司 Pramipexole transdermal patch system and method of use
CN107935962A (en) * 2017-11-17 2018-04-20 山东新华制药股份有限公司 The preparation method of 6s n-pentyl Pramipexole impurity
EP3784237B1 (en) * 2018-04-25 2023-11-01 Shinkei Therapeutics, Inc. Tetrabenazine transdermal delivery device
CN109999012A (en) * 2019-03-26 2019-07-12 大道隆达（北京）医药科技发展有限公司 A kind of Pramipexole transdermal patch and preparation method thereof
CN111904950B (en) * 2019-05-07 2023-05-05 上海京新生物医药有限公司 Pramipexole transdermal patch
EP4048268A4 (en) * 2019-10-22 2023-11-29 Shinkei Therapeutics, Inc. Tetrabenazine transdermal delivery device

Family Cites Families (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3598122A (en) 1969-04-01 1971-08-10 Alza Corp Bandage for administering drugs
US3598123A (en) 1969-04-01 1971-08-10 Alza Corp Bandage for administering drugs
US3797494A (en) 1969-04-01 1974-03-19 Alza Corp Bandage for the administration of drug by controlled metering through microporous materials
US3731683A (en) 1971-06-04 1973-05-08 Alza Corp Bandage for the controlled metering of topical drugs to the skin
US4031894A (en) 1975-12-08 1977-06-28 Alza Corporation Bandage for transdermally administering scopolamine to prevent nausea
US4201211A (en) 1977-07-12 1980-05-06 Alza Corporation Therapeutic system for administering clonidine transdermally
US4286592A (en) 1980-02-04 1981-09-01 Alza Corporation Therapeutic system for administering drugs to the skin
US4314557A (en) 1980-05-19 1982-02-09 Alza Corporation Dissolution controlled active agent dispenser
US4379454A (en) 1981-02-17 1983-04-12 Alza Corporation Dosage for coadministering drug and percutaneous absorption enhancer
US4849226A (en) 1981-06-29 1989-07-18 Alza Corporation Method for increasing oxygen supply by administering vasodilator
US4725272A (en) 1981-06-29 1988-02-16 Alza Corporation Novel bandage for administering beneficial drug
US4435180A (en) 1982-05-25 1984-03-06 Alza Corporation Elastomeric active agent delivery system and method of use
US4559222A (en) 1983-05-04 1985-12-17 Alza Corporation Matrix composition for transdermal therapeutic system
US4704282A (en) 1984-06-29 1987-11-03 Alza Corporation Transdermal therapeutic system having improved delivery characteristics
US4588580B2 (en) 1984-07-23 1999-02-16 Alaz Corp Transdermal administration of fentanyl and device therefor
US4568343A (en) 1984-10-09 1986-02-04 Alza Corporation Skin permeation enhancer compositions
US4645502A (en) 1985-05-03 1987-02-24 Alza Corporation Transdermal delivery of highly ionized fat insoluble drugs
US4904475A (en) 1985-05-03 1990-02-27 Alza Corporation Transdermal delivery of drugs from an aqueous reservoir
US4698062A (en) 1985-10-30 1987-10-06 Alza Corporation Medical device for pulsatile transdermal delivery of biologically active agents
DE3775830D1 (en) 1986-06-13 1992-02-20 Alza Corp ACTIVATING A TRANSDERMAL DRUG DELIVERY SYSTEM THROUGH MOISTURE.
US4938759A (en) 1986-09-02 1990-07-03 Alza Corporation Transdermal delivery device having a rate controlling adhesive
US5344656A (en) 1986-09-12 1994-09-06 Alza Corporation Subsaturated transdermal therapeutic system having improved release characteristics
US4908027A (en) 1986-09-12 1990-03-13 Alza Corporation Subsaturated transdermal therapeutic system having improved release characteristics
US4816258A (en) 1987-02-26 1989-03-28 Alza Corporation Transdermal contraceptive formulations
US4788062A (en) 1987-02-26 1988-11-29 Alza Corporation Transdermal administration of progesterone, estradiol esters, and mixtures thereof
US5071656A (en) 1987-03-05 1991-12-10 Alza Corporation Delayed onset transdermal delivery device
US4943435A (en) 1987-10-05 1990-07-24 Pharmetrix Corporation Prolonged activity nicotine patch
US4917895A (en) 1987-11-02 1990-04-17 Alza Corporation Transdermal drug delivery device
US4781924A (en) 1987-11-09 1988-11-01 Alza Corporation Transdermal drug delivery device
US5656286A (en) * 1988-03-04 1997-08-12 Noven Pharmaceuticals, Inc. Solubility parameter based drug delivery system and method for altering drug saturation concentration
US5004610A (en) 1988-06-14 1991-04-02 Alza Corporation Subsaturated nicotine transdermal therapeutic system
WO1993023025A1 (en) 1992-05-13 1993-11-25 Alza Corporation Transdermal administration of oxybutynin
US5635203A (en) 1994-09-29 1997-06-03 Alza Corporation Transdermal device having decreased delamination
US6222030B1 (en) 1998-08-03 2001-04-24 Agilent Technologies, Inc. Solid phase synthesis of oligonucleotides using carbonate protecting groups and alpha-effect nucleophile deprotection
GB9828480D0 (en) * 1998-12-24 1999-02-17 Dermatech Limited Transdermal drug delivery system
DE10137082A1 (en) * 2001-07-28 2003-02-13 Hexal Ag Stable transdermal therapeutic system containing pramipexol or ropinirol, especially for treating Parkinson's disease, comprises backing, drug-containing pressure-sensitive adhesive matrix and protective layers
DE10137162A1 (en) * 2001-07-30 2003-02-20 Hexal Ag Transdermal therapeutic system for administration of pramipexole or ropinirole for treating Parkinson's disease, comprises backing layer, reservoir, semipermeable membrane, adhesive layer and protecting layer
DE10333393A1 (en) * 2003-07-23 2005-02-24 Lts Lohmann Therapie-Systeme Ag Transdermal therapeutic system with the active ingredient pramipexole
US20050202073A1 (en) 2004-03-09 2005-09-15 Mylan Technologies, Inc. Transdermal systems containing multilayer adhesive matrices to modify drug delivery
WO2008001200A2 (en) * 2006-06-29 2008-01-03 Antares Pharma Ipl Ag Transdermal composition having enhanced color stability
JP5665116B2 (en) * 2009-11-20 2015-02-04 日東電工株式会社 Patches and patch preparations
WO2012140604A1 (en) * 2011-04-15 2012-10-18 Sandoz Ag Stable formulations of pramipexole hydrochloride
DE102012205493A1 (en) * 2012-04-03 2013-10-10 Acino Ag A dopamine agonist-containing transdermal delivery system

Also Published As

Publication number Publication date
EP2999444A2 (en) 2016-03-30
WO2014188329A3 (en) 2015-03-12
US20160113908A1 (en) 2016-04-28
WO2014188329A2 (en) 2014-11-27
US9682068B2 (en) 2017-06-20
EP2999444A4 (en) 2016-10-12

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