CA3092757A1 - Transdermal therapeutic system comprising a silicone acrylic hybrid polymer - Google Patents
Transdermal therapeutic system comprising a silicone acrylic hybrid polymer Download PDFInfo
- Publication number
- CA3092757A1 CA3092757A1 CA3092757A CA3092757A CA3092757A1 CA 3092757 A1 CA3092757 A1 CA 3092757A1 CA 3092757 A CA3092757 A CA 3092757A CA 3092757 A CA3092757 A CA 3092757A CA 3092757 A1 CA3092757 A1 CA 3092757A1
- Authority
- CA
- Canada
- Prior art keywords
- active agent
- therapeutic system
- transdermal therapeutic
- silicone
- polymer
- 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.)
- Pending
Links
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 324
- 230000001225 therapeutic effect Effects 0.000 title claims abstract description 267
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 240
- 229920000642 polymer Polymers 0.000 title claims abstract description 215
- 239000013543 active substance Substances 0.000 claims abstract description 542
- 239000010410 layer Substances 0.000 claims description 540
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 253
- -1 aliphatic acrylates Chemical class 0.000 claims description 148
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 147
- 239000000203 mixture Substances 0.000 claims description 119
- 239000011159 matrix material Substances 0.000 claims description 116
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 103
- 229910052710 silicon Inorganic materials 0.000 claims description 79
- 239000010703 silicon Substances 0.000 claims description 79
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 74
- RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 claims description 68
- 239000000178 monomer Substances 0.000 claims description 66
- 230000001070 adhesive effect Effects 0.000 claims description 62
- 239000000853 adhesive Substances 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 60
- 239000007787 solid Substances 0.000 claims description 57
- 229960001736 buprenorphine Drugs 0.000 claims description 55
- 239000003795 chemical substances by application Substances 0.000 claims description 55
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 55
- 239000008199 coating composition Substances 0.000 claims description 53
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 52
- 229920002050 silicone resin Polymers 0.000 claims description 52
- 229920001577 copolymer Polymers 0.000 claims description 48
- 239000002904 solvent Substances 0.000 claims description 45
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 44
- 239000000243 solution Substances 0.000 claims description 44
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 41
- 238000004519 manufacturing process Methods 0.000 claims description 36
- 229920000058 polyacrylate Polymers 0.000 claims description 33
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 28
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 27
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 27
- 206010012289 Dementia Diseases 0.000 claims description 26
- 208000018737 Parkinson disease Diseases 0.000 claims description 26
- 239000011248 coating agent Substances 0.000 claims description 26
- 238000000576 coating method Methods 0.000 claims description 26
- 239000007795 chemical reaction product Substances 0.000 claims description 25
- 239000012790 adhesive layer Substances 0.000 claims description 22
- 229920002367 Polyisobutene Polymers 0.000 claims description 21
- 229920002554 vinyl polymer Polymers 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 238000009792 diffusion process Methods 0.000 claims description 20
- 238000001035 drying Methods 0.000 claims description 18
- 239000003999 initiator Substances 0.000 claims description 18
- 208000024891 symptom Diseases 0.000 claims description 15
- 239000008055 phosphate buffer solution Substances 0.000 claims description 14
- 239000011780 sodium chloride Substances 0.000 claims description 14
- 208000024827 Alzheimer disease Diseases 0.000 claims description 13
- 208000031124 Dementia Alzheimer type Diseases 0.000 claims description 13
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 13
- 238000006482 condensation reaction Methods 0.000 claims description 13
- 230000009529 traumatic brain injury Effects 0.000 claims description 13
- 239000002202 Polyethylene glycol Substances 0.000 claims description 10
- 229920003144 amino alkyl methacrylate copolymer Polymers 0.000 claims description 10
- 229920003147 ammonioalkyl methacrylate copolymer Polymers 0.000 claims description 10
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims description 10
- 229920003146 methacrylic ester copolymer Polymers 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 10
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000010030 laminating Methods 0.000 claims description 6
- 238000004080 punching Methods 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 4
- 210000003491 skin Anatomy 0.000 description 186
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 112
- 239000012071 phase Substances 0.000 description 68
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical group CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 description 55
- 229960004136 rivastigmine Drugs 0.000 description 51
- 238000012360 testing method Methods 0.000 description 40
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 35
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 30
- 230000001186 cumulative effect Effects 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000002585 base Substances 0.000 description 23
- 239000012528 membrane Substances 0.000 description 23
- 150000003254 radicals Chemical class 0.000 description 22
- 229940063557 methacrylate Drugs 0.000 description 21
- 239000008186 active pharmaceutical agent Substances 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 19
- 239000000523 sample Substances 0.000 description 19
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 17
- 230000002051 biphasic effect Effects 0.000 description 15
- 229940040102 levulinic acid Drugs 0.000 description 15
- 229940044374 butrans Drugs 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
- 238000005259 measurement Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 12
- 239000008384 inner phase Substances 0.000 description 12
- 239000002609 medium Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 229940117958 vinyl acetate Drugs 0.000 description 12
- 238000011068 loading method Methods 0.000 description 11
- 239000008385 outer phase Substances 0.000 description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 10
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 9
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 9
- 239000011888 foil Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 229940095095 2-hydroxyethyl acrylate Drugs 0.000 description 8
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 8
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 8
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 239000005038 ethylene vinyl acetate Substances 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 8
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 7
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 7
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 7
- 210000002615 epidermis Anatomy 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 125000005641 methacryl group Chemical group 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 229910020485 SiO4/2 Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 5
- 230000001839 systemic circulation Effects 0.000 description 5
- XKWFZGCWEYYGSK-UHFFFAOYSA-N 3,3,5,5-tetramethyl-2-methylidenehexanamide Chemical compound CC(C)(C)CC(C)(C)C(=C)C(N)=O XKWFZGCWEYYGSK-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000005370 alkoxysilyl group Chemical group 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
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- 239000003963 antioxidant agent Substances 0.000 description 4
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- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- 239000004148 curcumin Substances 0.000 description 4
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- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- 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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
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- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
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- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- 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
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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
- 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
- A61K9/7084—Transdermal patches having a drug layer or reservoir, and one or more separate drug-free skin-adhesive layers, e.g. between drug reservoir and skin, or surrounding the drug reservoir; Liquid-filled reservoir patches
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- 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
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- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Emergency Medicine (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18161437.1 | 2018-03-13 | ||
| EP18161437 | 2018-03-13 | ||
| PCT/EP2019/056028 WO2019175109A1 (en) | 2018-03-13 | 2019-03-11 | Transdermal therapeutic system comprising a silicone acrylic hybrid polymer |
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| CA3092757A Pending CA3092757A1 (en) | 2018-03-13 | 2019-03-11 | Transdermal therapeutic system comprising a silicone acrylic hybrid polymer |
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| EP (1) | EP3764998A1 (https=) |
| JP (1) | JP2021517572A (https=) |
| CN (1) | CN111971032A (https=) |
| BR (1) | BR112020018300A2 (https=) |
| CA (1) | CA3092757A1 (https=) |
| WO (1) | WO2019175109A1 (https=) |
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| CN118765196A (zh) * | 2022-01-27 | 2024-10-11 | Lts罗曼治疗系统股份公司 | 用于透皮施用赛乐西帕的透皮治疗系统 |
| WO2025038382A1 (en) * | 2023-08-11 | 2025-02-20 | Momentive Performance Materials Inc. | Pharmaceutical adhesive compositions |
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|---|---|---|---|---|
| US5362496A (en) * | 1993-08-04 | 1994-11-08 | Pharmetrix Corporation | Method and therapeutic system for smoking cessation |
| US5968547A (en) * | 1997-02-24 | 1999-10-19 | Euro-Celtique, S.A. | Method of providing sustained analgesia with buprenorphine |
| US6974588B1 (en) * | 1999-12-07 | 2005-12-13 | Elan Pharma International Limited | Transdermal patch for delivering volatile liquid drugs |
| TWI389709B (zh) * | 2005-12-01 | 2013-03-21 | Novartis Ag | 經皮治療系統 |
| EP2024406B1 (en) | 2006-06-06 | 2012-08-01 | Dow Corning Corporation | A silicone acrylate hybrid composition |
| DE102006054731B4 (de) * | 2006-11-21 | 2013-02-28 | Lts Lohmann Therapie-Systeme Ag | Transdermales therapeutisches System zur Verabreichung des Wirkstoffs Buprenorphin und Verwendung desselben in der Schmerztherapie |
| BRPI1014886B1 (pt) | 2009-04-24 | 2020-02-11 | Henkel IP & Holding GmbH | Polímeros acrílicos de silicone híbridos, seus métodos de preparação, adesivos e soluções de uma composição adesiva sensível à pressão compreendendo os mesmos. |
| DK2468274T3 (en) * | 2010-12-14 | 2015-08-31 | Acino Ag | Transdermal therapeutic system for administration of an active substance |
| JP2013139554A (ja) | 2011-11-29 | 2013-07-18 | Dow Corning Corp | シリコーンアクリレートハイブリッド組成物及び該組成物の製造方法 |
| TW201338813A (zh) | 2011-12-12 | 2013-10-01 | 洛曼治療系統股份有限公司 | 經皮遞送系統 |
| AU2013205080B2 (en) * | 2012-12-12 | 2016-07-07 | Lts Lohmann Therapie-Systeme Ag | Transdermal Delivery System |
| US10316228B2 (en) * | 2015-02-09 | 2019-06-11 | Dow Silicones Corporation | Multi-phase silicone acrylic hybrid visco-elastic compositions and methods of making same |
| US20170112781A1 (en) * | 2015-10-27 | 2017-04-27 | Noven Pharmaceuticals, Inc. | Transdermal drug delivery systems with polyisobutylene face adhesive |
| KR102381686B1 (ko) * | 2016-07-22 | 2022-04-01 | 에르테에스 로만 테라피-시스테메 아게 | 접착제 도메인의 제어 |
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- 2019-03-11 EP EP19709060.8A patent/EP3764998A1/en not_active Withdrawn
- 2019-03-11 US US15/733,596 patent/US20210038532A1/en not_active Abandoned
- 2019-03-11 CA CA3092757A patent/CA3092757A1/en active Pending
- 2019-03-11 WO PCT/EP2019/056028 patent/WO2019175109A1/en not_active Ceased
Also Published As
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| CN111971032A (zh) | 2020-11-20 |
| WO2019175109A1 (en) | 2019-09-19 |
| BR112020018300A2 (pt) | 2020-12-22 |
| EP3764998A1 (en) | 2021-01-20 |
| US20210038532A1 (en) | 2021-02-11 |
| JP2021517572A (ja) | 2021-07-26 |
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