ES2410532T3 - Adhesivo de acrilo útil en sistemas de administración transdérmica de fármacos - Google Patents
Adhesivo de acrilo útil en sistemas de administración transdérmica de fármacos Download PDFInfo
- Publication number
- ES2410532T3 ES2410532T3 ES01973175T ES01973175T ES2410532T3 ES 2410532 T3 ES2410532 T3 ES 2410532T3 ES 01973175 T ES01973175 T ES 01973175T ES 01973175 T ES01973175 T ES 01973175T ES 2410532 T3 ES2410532 T3 ES 2410532T3
- Authority
- ES
- Spain
- Prior art keywords
- acrylamide
- adhesive
- methacrylamide
- weight
- drug delivery
- 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.)
- Expired - Lifetime
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- -1 Acryl Chemical group 0.000 title claims abstract description 28
- 238000013271 transdermal drug delivery Methods 0.000 title claims abstract description 25
- 239000000853 adhesive Substances 0.000 title claims description 72
- 230000001070 adhesive effect Effects 0.000 title claims description 66
- 239000003814 drug Substances 0.000 claims abstract description 81
- 239000000178 monomer Substances 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims abstract description 17
- 125000000524 functional group Chemical group 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 229940124597 therapeutic agent Drugs 0.000 claims abstract description 8
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical group CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 5
- QJUCCGSXGKTYBT-UHFFFAOYSA-N 2,4,4-trimethylpent-2-enamide Chemical group NC(=O)C(C)=CC(C)(C)C QJUCCGSXGKTYBT-UHFFFAOYSA-N 0.000 claims abstract description 4
- WPFTVIVHDBZTSZ-UHFFFAOYSA-N 2-methyl-n-(2,4,4-trimethylpentan-2-yl)prop-2-enamide Chemical group CC(=C)C(=O)NC(C)(C)CC(C)(C)C WPFTVIVHDBZTSZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- JMADMUIDBVATJT-UHFFFAOYSA-N 2-methylprop-2-enamide;propan-2-one Chemical group CC(C)=O.CC(C)=O.CC(=C)C(N)=O JMADMUIDBVATJT-UHFFFAOYSA-N 0.000 claims abstract description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000010382 chemical cross-linking Methods 0.000 claims abstract description 4
- QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical group CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 claims abstract description 4
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical group CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims abstract description 4
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical group CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 23
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 12
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical group CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 5
- YRDNVESFWXDNSI-UHFFFAOYSA-N n-(2,4,4-trimethylpentan-2-yl)prop-2-enamide Chemical group CC(C)(C)CC(C)(C)NC(=O)C=C YRDNVESFWXDNSI-UHFFFAOYSA-N 0.000 claims description 5
- 230000003014 reinforcing effect Effects 0.000 claims description 4
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- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
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- PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 claims 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims 1
- YRVUCYWJQFRCOB-UHFFFAOYSA-N n-butylprop-2-enamide Chemical group CCCCNC(=O)C=C YRVUCYWJQFRCOB-UHFFFAOYSA-N 0.000 claims 1
- IJSVVICYGLOZHA-UHFFFAOYSA-N 2-methyl-n-phenylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=CC=CC=C1 IJSVVICYGLOZHA-UHFFFAOYSA-N 0.000 abstract description 3
- BPCNEKWROYSOLT-UHFFFAOYSA-N n-phenylprop-2-enamide Chemical group C=CC(=O)NC1=CC=CC=C1 BPCNEKWROYSOLT-UHFFFAOYSA-N 0.000 abstract description 3
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical group C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 abstract 1
- GASMGDMKGYYAHY-UHFFFAOYSA-N 2-methylidenehexanamide Chemical group CCCCC(=C)C(N)=O GASMGDMKGYYAHY-UHFFFAOYSA-N 0.000 abstract 1
- 229940079593 drug Drugs 0.000 description 72
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- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 3
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- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
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- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Medicinal Preparation (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23424800P | 2000-09-19 | 2000-09-19 | |
| US234248P | 2000-09-19 | ||
| PCT/US2001/029241 WO2002024157A2 (en) | 2000-09-19 | 2001-09-18 | Acryl adhesive useful in transdermal drug delivery systems |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2410532T3 true ES2410532T3 (es) | 2013-07-02 |
Family
ID=22880566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01973175T Expired - Lifetime ES2410532T3 (es) | 2000-09-19 | 2001-09-18 | Adhesivo de acrilo útil en sistemas de administración transdérmica de fármacos |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9056060B2 (enExample) |
| EP (1) | EP1318843B1 (enExample) |
| JP (2) | JP2004509222A (enExample) |
| KR (1) | KR100940245B1 (enExample) |
| AU (1) | AU2001292781A1 (enExample) |
| ES (1) | ES2410532T3 (enExample) |
| WO (1) | WO2002024157A2 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1318843B1 (en) * | 2000-09-19 | 2013-04-17 | Henkel AG & Co. KGaA | Acryl adhesive useful in transdermal drug delivery systems |
| DE10141650C1 (de) | 2001-08-24 | 2002-11-28 | Lohmann Therapie Syst Lts | Transdermales Therapeutisches System mit Fentanyl bzw. verwandten Substanzen |
| DE10141652B4 (de) | 2001-08-24 | 2011-04-07 | Lts Lohmann Therapie-Systeme Ag | Transdermales therapeutisches System auf der Basis von Polyacrylat-Haftklebern ohne funktionelle Gruppen und seine Verwendung |
| US8252320B2 (en) | 2004-10-21 | 2012-08-28 | Durect Corporation | Transdermal delivery system for sufentanil |
| US8246977B2 (en) | 2004-10-21 | 2012-08-21 | Durect Corporation | Transdermal delivery systems |
| US8383149B2 (en) | 2005-09-23 | 2013-02-26 | Alza Corporation | High enhancer-loading polyacrylate formulation for transdermal applications |
| WO2007035940A2 (en) | 2005-09-23 | 2007-03-29 | Alza Corporation | Transdermal norelgestromin delivery system |
| US20090130188A9 (en) * | 2005-09-29 | 2009-05-21 | National Starch And Chemical Investment Holding Company | Acrylic pressure sensitive adhesives |
| DE102005050654A1 (de) * | 2005-10-20 | 2007-04-26 | LABTEC Gesellschaft für technologische Forschung und Entwicklung mbH | Lippenpflaster |
| CN101431988A (zh) * | 2006-02-27 | 2009-05-13 | 诺芬药品公司 | 包含东莨菪碱的透皮治疗系统 |
| US20100087768A1 (en) * | 2008-10-02 | 2010-04-08 | Forlano Paula | Transdermal drug delivery system for liquid active ingredient |
| US9717697B2 (en) | 2012-10-15 | 2017-08-01 | Noven Pharmaceuticals, Inc. | Compositions and methods for the transdermal delivery of methylphenidate |
| US10493024B2 (en) | 2015-10-12 | 2019-12-03 | Hk Tumescent Pharma Corporation | Tumescent infiltration drug delivery of high subcutaneous drug concentrations with prolonged local and systemic effects and minimal local or systemic toxicity |
| US11241412B2 (en) | 2015-10-12 | 2022-02-08 | Hk Pharma | Tumescent infiltration drug delivery of cannabinoids |
| US20200131409A1 (en) * | 2017-04-17 | 2020-04-30 | 3M Innovative Properties Company | Blended block copolymer/silicone pressure sensitive adhesives |
| CA3097189A1 (en) * | 2018-04-25 | 2019-10-31 | Shinkei Therapeutics Llc | Tetrabenazine transdermal delivery device |
| KR102207590B1 (ko) * | 2018-08-06 | 2021-01-26 | 고세윤 | 생체의료용 고분자를 포함하는 피부 무자극 점착제 조성물 및 이를 이용한 점착시트 |
| EP3997138A4 (en) * | 2019-07-11 | 2023-02-22 | Henkel AG & Co. KGaA | ACRYLIC POLYMER AND ADHESIVE COMPOSITIONS |
| FI3854388T3 (fi) | 2020-01-24 | 2023-11-27 | Luye Pharma Switzerland Ag | Transdermaalinen hoitojärjestelmä, jossa on vaikuttava aine rotigotiini ja ainakin yksi ei-amiiniresistentti silikoniliima |
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| DE20113761U1 (de) | 2001-08-20 | 2001-12-20 | Lohmann & Rauscher GmbH & Co. KG, 56567 Neuwied | Wundversorgungsprodukt |
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-
2001
- 2001-09-18 EP EP01973175.1A patent/EP1318843B1/en not_active Expired - Lifetime
- 2001-09-18 AU AU2001292781A patent/AU2001292781A1/en not_active Abandoned
- 2001-09-18 KR KR1020037003644A patent/KR100940245B1/ko not_active Expired - Fee Related
- 2001-09-18 US US09/955,644 patent/US9056060B2/en not_active Expired - Fee Related
- 2001-09-18 WO PCT/US2001/029241 patent/WO2002024157A2/en not_active Ceased
- 2001-09-18 JP JP2002528194A patent/JP2004509222A/ja active Pending
- 2001-09-18 ES ES01973175T patent/ES2410532T3/es not_active Expired - Lifetime
-
2013
- 2013-05-14 JP JP2013101967A patent/JP5702434B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR100940245B1 (ko) | 2010-02-04 |
| WO2002024157A3 (en) | 2003-01-23 |
| EP1318843B1 (en) | 2013-04-17 |
| EP1318843A2 (en) | 2003-06-18 |
| JP2004509222A (ja) | 2004-03-25 |
| US20020077437A1 (en) | 2002-06-20 |
| AU2001292781A1 (en) | 2002-04-02 |
| JP5702434B2 (ja) | 2015-04-15 |
| WO2002024157A2 (en) | 2002-03-28 |
| US9056060B2 (en) | 2015-06-16 |
| KR20040030408A (ko) | 2004-04-09 |
| JP2013163820A (ja) | 2013-08-22 |
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