CA2875454C - Composition for patch preparation comprising drug, organic solvent, lipophilic mass base, and powder - Google Patents
Composition for patch preparation comprising drug, organic solvent, lipophilic mass base, and powder Download PDFInfo
- Publication number
- CA2875454C CA2875454C CA2875454A CA2875454A CA2875454C CA 2875454 C CA2875454 C CA 2875454C CA 2875454 A CA2875454 A CA 2875454A CA 2875454 A CA2875454 A CA 2875454A CA 2875454 C CA2875454 C CA 2875454C
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- CA
- Canada
- Prior art keywords
- drug
- powder
- acid
- composition according
- triethanolamine
- Prior art date
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- 239000003814 drug Substances 0.000 title claims abstract description 188
- 238000002360 preparation method Methods 0.000 title claims abstract description 180
- 229940079593 drug Drugs 0.000 title claims abstract description 179
- 239000000843 powder Substances 0.000 title claims abstract description 102
- 239000000203 mixture Substances 0.000 title claims abstract description 72
- 239000003960 organic solvent Substances 0.000 title claims abstract description 47
- 239000002608 ionic liquid Substances 0.000 claims abstract description 65
- -1 carboxylic acid compound Chemical class 0.000 claims description 33
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 30
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 30
- 229940043276 diisopropanolamine Drugs 0.000 claims description 29
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims description 27
- 235000012239 silicon dioxide Nutrition 0.000 claims description 27
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 25
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 20
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 18
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- 150000003839 salts Chemical class 0.000 claims description 18
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- JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 claims description 14
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- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 12
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- 229960004418 trolamine Drugs 0.000 claims description 12
- RJQQOKKINHMXIM-UHFFFAOYSA-N 2-hydroxypropanoate;tris(2-hydroxyethyl)azanium Chemical compound CC(O)C(O)=O.OCCN(CCO)CCO RJQQOKKINHMXIM-UHFFFAOYSA-N 0.000 claims description 11
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 11
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- JFNWWQMIGPYWED-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;16-methylheptadecanoic acid Chemical compound OCCN(CCO)CCO.CC(C)CCCCCCCCCCCCCCC(O)=O JFNWWQMIGPYWED-UHFFFAOYSA-N 0.000 claims description 8
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 8
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- KBKGPMDADJLBEM-UHFFFAOYSA-N 1-(4-pentylphenyl)ethanone Chemical compound CCCCCC1=CC=C(C(C)=O)C=C1 KBKGPMDADJLBEM-UHFFFAOYSA-N 0.000 claims description 7
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical compound O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
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- INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical compound CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 description 1
- 229960002409 mepivacaine Drugs 0.000 description 1
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- DVEKCXOJTLDBFE-UHFFFAOYSA-N n-dodecyl-n,n-dimethylglycinate Chemical compound CCCCCCCCCCCC[N+](C)(C)CC([O-])=O DVEKCXOJTLDBFE-UHFFFAOYSA-N 0.000 description 1
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 239000000014 opioid analgesic Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- HIANJWSAHKJQTH-UHFFFAOYSA-N pemirolast Chemical compound CC1=CC=CN(C2=O)C1=NC=C2C=1N=NNN=1 HIANJWSAHKJQTH-UHFFFAOYSA-N 0.000 description 1
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- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- ONQDVAFWWYYXHM-UHFFFAOYSA-M potassium lauryl sulfate Chemical compound [K+].CCCCCCCCCCCCOS([O-])(=O)=O ONQDVAFWWYYXHM-UHFFFAOYSA-M 0.000 description 1
- 229940116985 potassium lauryl sulfate Drugs 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 229940075579 propyl gallate Drugs 0.000 description 1
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
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- 108700004121 sarkosyl Proteins 0.000 description 1
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- KQPKPCNLIDLUMF-UHFFFAOYSA-N secobarbital Chemical compound CCCC(C)C1(CC=C)C(=O)NC(=O)NC1=O KQPKPCNLIDLUMF-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000004799 sedative–hypnotic effect Effects 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 229940045885 sodium lauroyl sarcosinate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
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- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
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- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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- NZHGWWWHIYHZNX-CSKARUKUSA-N tranilast Chemical compound C1=C(OC)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1C(O)=O NZHGWWWHIYHZNX-CSKARUKUSA-N 0.000 description 1
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Classifications
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- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- A61K31/407—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 other heterocyclic ring systems, e.g. ketorolac, physostigmine
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Landscapes
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- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| PCT/JP2013/066765 WO2013191187A1 (ja) | 2012-06-20 | 2013-06-18 | 薬剤と有機溶媒と親油性膏体基剤と粉体を配合した貼付製剤組成物 |
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| EP3824883B1 (en) * | 2013-09-11 | 2023-08-02 | MEDRx Co., Ltd. | Novel composition for plaster base material in tape preparation |
| CN103830206B (zh) * | 2014-02-26 | 2016-08-31 | 上海现代药物制剂工程研究中心有限公司 | 阿戈美拉汀三维网状立体构型的透皮给药制剂及制备方法 |
| US10045948B2 (en) | 2014-02-27 | 2018-08-14 | Medrx Co., Ltd. | Pramipexole-containing transdermal patch for treatment of neurodegenerative disease |
| WO2016109483A1 (en) * | 2014-12-30 | 2016-07-07 | Noven Pharmaceuticals, Inc. | Transdermal drug delivery systems for agomelatine |
| US10016502B2 (en) | 2015-08-29 | 2018-07-10 | Medrx Co., Ltd | Patch preparation containing an acid scavenger |
| WO2017037812A1 (ja) * | 2015-08-29 | 2017-03-09 | 株式会社メドレックス | 酸捕捉剤を含有する貼付製剤 |
| CN107427509B (zh) * | 2015-08-29 | 2021-06-15 | 美德阿利克斯株式会社 | 含有碱性药物和山梨酸的经皮吸收组成物 |
| ES2957234T3 (es) * | 2016-03-24 | 2024-01-15 | Medrx Co Ltd | Preparación de parche con características de prevención del uso incorrecto de sustancias |
| US20170273974A1 (en) | 2016-03-24 | 2017-09-28 | Medrx Co., Ltd | Patch preparations with misuse prevention features |
| JP7143219B2 (ja) * | 2016-11-09 | 2022-09-28 | 株式会社クラレ | 粘着シート、絆創膏及びこれらの製造方法 |
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| JPH06145050A (ja) | 1992-11-11 | 1994-05-24 | Sekisui Chem Co Ltd | 貼付剤の製造方法 |
| JPH07145047A (ja) | 1993-11-25 | 1995-06-06 | Sekisui Chem Co Ltd | 局所麻酔用経皮吸収テープ |
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| DE10033853A1 (de) * | 2000-07-12 | 2002-01-31 | Hexal Ag | Transdermales therapeutisches System mit hochdispersem Siliziumdioxid |
| US6503532B1 (en) * | 2001-04-13 | 2003-01-07 | Murty Pharmaceuticals, Inc. | Pharmaceutical composition containing tetrahydrocannabinol and a transdermal/transcutaneous delivery method thereof |
| US7785622B2 (en) * | 2002-09-13 | 2010-08-31 | Hisamitsu Pharmaceutical Co., Inc. | Adhesive patch for fentanyl administration |
| JP4629578B2 (ja) * | 2003-01-22 | 2011-02-09 | ニチバン株式会社 | 眼疾患治療用経皮吸収型製剤 |
| US8080261B2 (en) * | 2004-09-30 | 2011-12-20 | Teikoku Pharma Usa, Inc. | 1-chloro-2,4-dinitrobenzene non-aqueous gel compositions and methods for using the same |
| WO2008032718A1 (en) * | 2006-09-11 | 2008-03-20 | Sekisui Chemical Co., Ltd. | Adhesive preparation |
| ATE543490T1 (de) † | 2006-09-11 | 2012-02-15 | Sekisui Chemical Co Ltd | Klebende zubereitung mit desglymidodrin |
| US8623387B2 (en) * | 2007-11-22 | 2014-01-07 | Medrx Co., Ltd. | External preparation composition comprising fatty acid-based ionic liquid as active ingredient |
| US20110189261A1 (en) | 2008-03-03 | 2011-08-04 | Hisamitsu Pharmaceutical Co., Inc. | Transdermally absorbable preparation |
| JP4822032B2 (ja) | 2009-01-08 | 2011-11-24 | タイヨーエレック株式会社 | 組合せ式遊技機 |
| WO2010113225A1 (en) * | 2009-03-30 | 2010-10-07 | Yutoku Pharmaceutical Industries Co., Ltd. | Riluzole-containing transdermal patch |
| DE102009022915A1 (de) * | 2009-05-27 | 2010-12-09 | Lts Lohmann Therapie-Systeme Ag | Transdermales therapeutisches System mit gesteuertem Wirkstofffluss |
| JP2011074035A (ja) | 2009-09-30 | 2011-04-14 | Sekisui Medical Co Ltd | 貼付剤 |
-
2013
- 2013-06-18 PT PT13806076T patent/PT2865376T/pt unknown
- 2013-06-18 CN CN201911053677.0A patent/CN110693859A/zh active Pending
- 2013-06-18 DK DK13806076.9T patent/DK2865376T4/da active
- 2013-06-18 CN CN201380031729.9A patent/CN104363900A/zh active Pending
- 2013-06-18 TR TR2019/11328T patent/TR201911328T4/tr unknown
- 2013-06-18 SI SI201331532T patent/SI2865376T1/sl unknown
- 2013-06-18 WO PCT/JP2013/066765 patent/WO2013191187A1/ja not_active Ceased
- 2013-06-18 CA CA2875454A patent/CA2875454C/en active Active
- 2013-06-18 AU AU2013278403A patent/AU2013278403B2/en not_active Ceased
- 2013-06-18 ES ES13806076T patent/ES2738303T5/es active Active
- 2013-06-18 EP EP13806076.9A patent/EP2865376B2/en active Active
- 2013-06-18 JP JP2014521482A patent/JP6309892B2/ja active Active
- 2013-06-18 US US14/408,649 patent/US10543275B2/en active Active
- 2013-06-18 PL PL13806076.9T patent/PL2865376T5/pl unknown
- 2013-06-18 BR BR112014031701A patent/BR112014031701A2/pt not_active Application Discontinuation
- 2013-06-18 CN CN201810750500.5A patent/CN108553452A/zh active Pending
- 2013-06-18 HU HUE13806076A patent/HUE045479T2/hu unknown
- 2013-06-18 IN IN10706DEN2014 patent/IN2014DN10706A/en unknown
-
2019
- 2019-09-09 US US16/564,587 patent/US12016924B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| IN2014DN10706A (enExample) | 2015-09-04 |
| SI2865376T1 (sl) | 2019-11-29 |
| US20190388544A1 (en) | 2019-12-26 |
| BR112014031701A2 (pt) | 2017-06-27 |
| EP2865376B1 (en) | 2019-06-05 |
| EP2865376A4 (en) | 2015-11-18 |
| TR201911328T4 (tr) | 2019-08-21 |
| JP6309892B2 (ja) | 2018-04-11 |
| ES2738303T3 (es) | 2020-01-21 |
| DK2865376T3 (da) | 2019-08-12 |
| CA2875454A1 (en) | 2013-12-27 |
| WO2013191187A1 (ja) | 2013-12-27 |
| JPWO2013191187A1 (ja) | 2016-05-26 |
| HUE045479T2 (hu) | 2019-12-30 |
| PL2865376T5 (pl) | 2023-01-09 |
| US20150174249A1 (en) | 2015-06-25 |
| CN104363900A (zh) | 2015-02-18 |
| US10543275B2 (en) | 2020-01-28 |
| US12016924B2 (en) | 2024-06-25 |
| EP2865376A1 (en) | 2015-04-29 |
| AU2013278403A1 (en) | 2015-01-22 |
| PT2865376T (pt) | 2019-08-26 |
| CN110693859A (zh) | 2020-01-17 |
| ES2738303T5 (es) | 2022-09-12 |
| DK2865376T4 (da) | 2022-07-18 |
| EP2865376B2 (en) | 2022-05-11 |
| AU2013278403B2 (en) | 2018-02-01 |
| PL2865376T3 (pl) | 2019-12-31 |
| CN108553452A (zh) | 2018-09-21 |
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