WO2005046653A1 - Emplatre antiphlogistique et analgesique comprenant un compose de felbinac - Google Patents
Emplatre antiphlogistique et analgesique comprenant un compose de felbinac Download PDFInfo
- Publication number
- WO2005046653A1 WO2005046653A1 PCT/KR2004/002965 KR2004002965W WO2005046653A1 WO 2005046653 A1 WO2005046653 A1 WO 2005046653A1 KR 2004002965 W KR2004002965 W KR 2004002965W WO 2005046653 A1 WO2005046653 A1 WO 2005046653A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- felbinac
- plaster
- drug
- adhesive
- plaster according
- Prior art date
Links
- 239000011505 plaster Substances 0.000 title claims abstract description 70
- 229960000192 felbinac Drugs 0.000 title claims abstract description 64
- -1 felbinac compound Chemical class 0.000 title claims description 9
- 239000002260 anti-inflammatory agent Substances 0.000 title abstract description 5
- 230000000202 analgesic effect Effects 0.000 title description 2
- 230000001741 anti-phlogistic effect Effects 0.000 title description 2
- QRZAKQDHEVVFRX-UHFFFAOYSA-N biphenyl-4-ylacetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CC=CC=C1 QRZAKQDHEVVFRX-UHFFFAOYSA-N 0.000 claims abstract description 68
- 239000002904 solvent Substances 0.000 claims abstract description 26
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims abstract description 24
- 239000003961 penetration enhancing agent Substances 0.000 claims abstract description 23
- 239000006184 cosolvent Substances 0.000 claims abstract description 13
- 229940079593 drug Drugs 0.000 claims description 57
- 239000003814 drug Substances 0.000 claims description 57
- 239000000853 adhesive Substances 0.000 claims description 36
- 230000001070 adhesive effect Effects 0.000 claims description 35
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 14
- 239000000194 fatty acid Substances 0.000 claims description 14
- 229930195729 fatty acid Natural products 0.000 claims description 14
- 150000004665 fatty acids Chemical class 0.000 claims description 14
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 12
- 238000009792 diffusion process Methods 0.000 claims description 12
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 229920001971 elastomer Polymers 0.000 claims description 8
- 239000005060 rubber Substances 0.000 claims description 8
- 239000002736 nonionic surfactant Substances 0.000 claims description 7
- 230000002441 reversible effect Effects 0.000 claims description 6
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 4
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 4
- 229940055577 oleyl alcohol Drugs 0.000 claims description 4
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004840 adhesive resin Substances 0.000 claims description 3
- 229920006223 adhesive resin Polymers 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- 150000003505 terpenes Chemical class 0.000 claims description 3
- 235000007586 terpenes Nutrition 0.000 claims description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 2
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 claims description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 2
- 235000021360 Myristic acid Nutrition 0.000 claims description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims description 2
- LLRANSBEYQZKFY-UHFFFAOYSA-N dodecanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCCCCCC(O)=O LLRANSBEYQZKFY-UHFFFAOYSA-N 0.000 claims description 2
- 229940070765 laurate Drugs 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 229940102253 isopropanolamine Drugs 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
- 230000005923 long-lasting effect Effects 0.000 abstract description 5
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 abstract description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 abstract description 5
- 208000002193 Pain Diseases 0.000 abstract description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
- 230000002757 inflammatory effect Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 33
- 238000002360 preparation method Methods 0.000 description 33
- 238000000034 method Methods 0.000 description 29
- 230000000052 comparative effect Effects 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- 210000003491 skin Anatomy 0.000 description 19
- 239000003522 acrylic cement Substances 0.000 description 13
- 239000002253 acid Substances 0.000 description 11
- 231100000245 skin permeability Toxicity 0.000 description 11
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- DNTGGZPQPQTDQF-XBXARRHUSA-N crotamiton Chemical group C/C=C/C(=O)N(CC)C1=CC=CC=C1C DNTGGZPQPQTDQF-XBXARRHUSA-N 0.000 description 4
- 229960003338 crotamiton Drugs 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 2
- 201000003068 rheumatic fever Diseases 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 231100000475 skin irritation Toxicity 0.000 description 2
- 230000007480 spreading Effects 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 1
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000008035 Back Pain Diseases 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- 239000000006 Nitroglycerin Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229960002896 clonidine Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000010579 first pass effect Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 208000024798 heartburn Diseases 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 230000000391 smoking effect Effects 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
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 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
- 238000013112 stability test Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2121/00—Preparations for use in therapy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Definitions
- the present invention relates to an anti-inflammatory plaster comprising felbinac (4-biphenyl acetic acid) as an effective ingredient.
- Drug plaster has been introduced to the treatment of various diseases as one of TTS (Transdermal Treatment System) from long years ago.
- the drug plaster containing various drugs such as nitroglycerin for treating angina pectoris, nicotine for abstaining from smoking, estradiol for treating various diseases caused by menopause and clonidine for lowering blood pressure has been developed and sold on the market.
- TTS shows systemic action due to distributed active substance into the circulatory blood vessel in human body which has been already absorbed through skin.
- NSAID Non-steroidal Anti- inflammatory Drug
- RA rheumatic arthritis
- NSAID has lots of limits to use in long term administration caused by severe adverse action for example, heart burn, gastritis, gastriorrhagia and the like as an anti-inflammatory drug since it inhibits the release of gastrointestinal protecting substance from gastric juice.
- H 4-321624 discloses ant i-inflammatory patch wherein base is styrene-isoprene-styrene block copolymer and solubiliser is crotamitone, however it has several disadvantages such as the reduction of adhesive ability because of the surface extrusion of crotamitone and the difficulty in handling crotamitone.
- PCT/W098/24423 discloses anti- inflammatory patch including styrene-isoprene-styrene block copolymer, rosin resin, plasticizer and felbinac without crotamitone, however it has also some problems such as inequitable needs in maximizing skin permeating rate and inducing stable release of the drug for the application period because of its low concentration of active ingredient in the patch, i.e., about 1 to 5 (w/w) %.
- Korean Patent No. 2002-0079811 discloses felbinac preparation of skin permeability improved by adopting water soluble additive to hot-meIt adhesive base, however it has also limits to increase the content of felbinac.
- the inventive patch can accomplish various advantages such as high- concentrated preparation of felbinac, drug stability, increased skin permeability and so on by adopting specific components; alkanolamine as a solubilizing agent, N-alkyl-pyrrolidone as a co-solvent, non-ionic surfactant, fatty acid, fatty acid derivative and the mixture thereof as epidermal permeation enhancer, and specific structured patch; multi-layered structure comprising primer layer consisting of rubber adhesive for preventing the reverse diffusion of drug from support and improving skin adhesive ability, which can maintain long-lasting ant i-inflammatory effect of felbinac and endow with superior stability and adhesive ability to conventional patches, and have finally completed the present invention.
- Disclosure [Technical Problem]
- the present invention improve the reduction of adhesive ability due to solubilizer and organic solvent, the difficulty in handling and the demerits , low skin-permeability and the reduction of adhesive ability, because of extraction of the crystal of drug when the drug is high-concentrated in the plaster not containing solubilizer.
- the present invention provide felbinac-containing plaster having long lasting anti-inflammatory effect, superior stability and adhering force to the conventional plasters therefore.
- [Technical Solution] o> Accordingly, it is an object of the present invention to provide novel plaster comprising felbinac (4-biphenyl acetic acid) as a NSAID anti- inflammatory agent, solubilizer, co-solvent, epidermal permeation enhancer, and pressure sensitive adhesive as a support.
- felbinac-containing plaster comprising 1 to 25 w% felbinac (4- biphenyl acetic acid) as an active ingredient, 0.1 to 7 w% alkanolamine as a solubilizer, N-alkyl-pyrrol idone as a co-solvent, 1 to 20 w at least one epidermal permeation enhancer selected from non-ionic surfactant, fatty acid and fatty acid derivative and 30 to 90 w% pressure sensitive adhesive as a support .
- alkanolamine may be used as a solubilizer; N-alkyl- pyrrol idone as a co-solvent; non-ionic surfactant, fatty acid, fatty acid derivative and the mixture thereof as epidermal permeation enhancer; and acrylic adhesive, water soluble adhesive, rubber adhesive and the like as a pressure sensitive adhesive.
- felbinac in an amount rnaging from about 1 to 25 w% may be used as an active ingredient; non-ionic surfactant, fatty acid, fatty acid derivative or the mixture thereof in an amount ranging from 1 to 20 w% may be used as an epidermal permeation enhancer, pressure sensitive adhesive in an amount rainging from 30 to may be used as a support .
- the inventive plaster according to the present invention may comprise active ingredient, solubilizer, co-solvent, epidermal permeation enhancer, pressure sensitive adhesive, and other conventionally used additives in the art.
- the composition in the plaster may comprise felbinac as an active ingredient in an amount of from 1 to 25 w% preferably, 3 to 20 w% more preferably, in total weight of inventive composition of which weight ratio of active ingredient can provide with optimum conditions such as good skin permeability, inconstant efficacy and stability of the drug, and economic interest. If the amount of felbinac in the composition is less than 1 w%, the sufficient efficacy of drug could not exert and if more than 25 w%, various problems, for example, extraction of drug crystal, decrease of adhesive force etc may occur.
- the alkanolamine adopted by a solubilizer in the present invention has been used as a emulsifier, stabilizer, alkaline agent etc and used to increase the solubility of insoluble drug as disclosed in prior patents (United State Patent Nos. 4,678,666 and 5,436,241; European Patent No. 0276561 (BI); Korean patent No. 10-0212961). If the used amount of the agent exceeds in the amount of active ingredient, it causes to several problems such as the decrease of skin permeability or adhesive force of preparation, yellow coloring phenomenon in the process of preparation whereas the solubility of drug in the composition is increased.
- present invention adopts N-alkyl-pyrrol idone as a co-solvent for increasing the drug amount in the adhesive composition before spreading and appropriate amount of alkanolamine as a solubilizer for improving the solubility of insoluble felbinac in the preparation in order to obtain purposed high concentrated felbinac plaster excluding any other disadvantages such as the decrease of adhesive ability or yellow coloring phenomenon.
- alkanolamine can increase adhesive force by acting as a plasticizer resulting in improving adhering ability to skin and accordingly improving skin permeability together with good compatibility with pressure sensitive adhesive.
- methanolamine, ethanolamine, propanolamine, isopropylamine and other alkanolamines may be used herein in the amount of preferably, from about 0.1 to 7 w%, more preferably, 1 to 5 w% in total composition.
- the uniformity between adhesive and felbinac is not so enough to obtain uniformed drug releasing rate whereas if the amount is more than 7 w%, the drug releasing rate may be decreased due to the interaction between alkanolamine and felbinac and the adhesive ability due to the increased amount of alkanolamine in the preparation may decrease.
- N-alkyl-pyrrrol idone preferably, N-methyl-2-pyrrolidione may be used in the present invention as a co-solvent. N-methyl-2-pyrrol idone is easily disappeared in the drying process in spite of its good solubility for felbinac therefore it can improve skin permeability and minimize skin irritation.
- the amount of N-alkyl-pyrrol idone ranging from 0.5 to 3 folds of the amount of felbinac can be preferably used. If the amount is less than 0.5 fold of the amount of felbinac, additional other solvent to solve felbinac is necessary and the remaining co-solvent may cause to deteriorate the physical property of plaster, i.e., adhesive force and attachment force to skin etc.
- non-ionic surfactant such as monoglyceride, sorbitan ester, sorbitan ester oxyethylene etc, fatty acid such as oleic acid, linoleic acid, capric acid, myristic acid etc, or fatty acid derivative such as oleyl alcohol, isopropyl myristate, propylene glycol laurate, polyethylene glycol laurate etc
- Those epidermal permeation enhancers can be use as a sole or the combination thereof in the amount ranging from 1 to 30 w%, preferably, 5 to 20 w% more preferably.
- acrylic adhesive consisting of acrylate polymer, rubber adhesive and water soluble adhesive prepared by adding several additive i.e., adhesive resin such as oil resin, rosin resin, terpene resin etc, oil, anti-oxidants to natural or synthetic rubber
- adhesive resin such as oil resin, rosin resin, terpene resin etc, oil, anti-oxidants to natural or synthetic rubber
- Those pressure sensitive adhesive can be use as a sole or the combination thereof in the amount ranging from 30 to 90 w%, preferably, from 45 to 70 w more preferably. If the amount of the adhesive is less than 30 w%, the cohesive force of the preparation is collapsed resulting in unfavorable problems such as skin transfer etc and the amount of active ingredient and other components can be limited to use and the adherence power is lessened if more than 90 w%.
- the support layer (1) for preventing from drug diffusion as a base layer, primer layer (2) located thereon for preventing from the reverse diffusion of drug and improving skin adhesive ability, drug containing layer (3) located thereon containing felbinac thereon, and release liner (4) located at the uppermost which could be released by patient's hand.
- the support (1) is made from the materials showing good humid permeability and elasticity, which do not interact between the drug and other composition in drug layer (3).
- the material of the support may effect on drug release.
- Synthetic resin film such as polyethylene, polypropylene, polyester and polyurethane etc, sheet, sheet foams, woven or non-woven and their laminates thereof can be preferably used as a support (3) in the present invention.
- Preferable thickness of the support layer ranges from 30 to 200 urn, however if the width is out of the range, the skin adhering force of patch can be worse due to the decrease of adhesive force and elasticity when the patch is applied to skin.
- the primer layer (2) existed in inner side of the support (1) plays a role of preventing from the reverse diffusion of drug and improving skin adhesive ability and it consists of rubber adhesive prepared by adding several additive i.e., adhesive resin such as oil resin, rosin resin, terpene resin etc, oil, anti-oxidants to natural or synthetic rubber.
- Preferable thickness of the primer layer ranges from 5 to 40 urn, however if the thickness is out of the range, it could ' not prevent from the reverse diffusion of drug sufficiently or improve skin adhesive ability resulting in preventing cohesive force of adhesive agent and lowering skin adhering ability in the end, >
- the drug containing layer (3) consists of mainly felbinac, pressure sensitive adhesive, solubilizer, co-solvent, dispersing agent, epidermal permeation accelerator and skin irritation preventing agent or plasticizer may be added thereto if required.
- the drug layer containing felbinac and other components consists of mono-layer or multi-layer having more than two layers having thickness of each layer ranging from 10 to 150 um, preferably, from 20 to 120 um and thickness of total layers ranging from 30 to 500 um, preferably, from 50 to 200 um.
- the drug containing layer can be formed by mono layer or bi-layer of which component of each layer may be same or different from each other in order to form multi-layer laminated with each layers wherein the closest layer to skin could release felbinac most rapidly and the layer showing the slowest releasing velocity is positioned to be closest to primer layer (2) preferably.
- the release liner (4) can be formed with polyester film coated with silicone or fluoride, polyethylene film or paper to be attached to drug containing layer (3).
- the inventive felbinac-containing plaster can provide with long lasting anti-inflammatory effect, superior stability and adhering force to the conventional plasters therefore, it can be useful as an effective felbinac- containing plaster to treat and alleviate various inflammation and pain inconsistently.
- Fig. 1 presents a sectional diagram showing one embodiment example of inventive preparation
- Fig. 2 represents the comparison of skin permeation amount experimented in hairless mouse between the Example 1 of the present invention, comparative example and conventional plaster.
- Comparative Example 1 Preparation of Comparative plaster (1) > 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer and 5 w% felbinac were added to 5 w% N-methyl-2-pyrrol idone used as a co- solvent and stirred to solve completely. 77 w% rubber adhesive was added thereto and stirred for 30 mins sufficiently. 3 w% triethanolamine used as a solubilizer was further added thereto and stirred for 30 mins removing air bubble.
- the mixture was spread on a release liner in order to the mixture 2 contains 0.17 mg/cm of drug and dried at 90°C for 20 mins to remove volatile co-solvent and volatile ingredient in pressure sensitive adhesive. After the drying process, the exposed dug-containing layer was closed with already prepared support layer spread with primer layer.
- the plaster prepared by above procedure was cut into appropriate size to prepare felbinac containing comparative plaster (1) to use as a sample in following Experimental Examples.
- Comparative Example 2 Preparation of Comparative plaster (2) o> Comparative plaster (2) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer, 15 w% felbinac, 67 w% rubber adhesive as a pressure sensitive adhesive, 3 w% 2 triethanolamine as a solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples.
- Comparative Example 3 Preparation of Comparative plaster (3)
- Comparative plaster (3) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer, 15 w% felbinac, 70 w acrylic adhesive as a pressure sensitive adhesive, and 0.50 2 mg/cm of drug content to use as a sample in following Experimental Examples.
- Example 1 Preparation of inventive plaster (1) t ⁇ > Inventive plaster (1) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer, 5 w felbinac, 77 w% acrylic adhesive as a pressure sensitive adhesive, and 0.17 2 mg/cm of drug content to use as a sample in following Experimental Examples.
- Example 2 Preparation of inventive plaster (2) 5> Inventive plaster (2) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer, 10 w% felbinac, 72 w% acrylic adhesive as a pressure sensitive adhesive, and 0.34 2 mg/cm of drug content to use as a sample in following Experimental Examples.
- Example 3 Preparation of inventive plaster (3) ⁇ -8> Inventive plaster (3) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer, 20 w% felbinac, 62 w% acrylic adhesive as a pressure sensitive adhesive, 3 w% 2 triethanolamine as a solubilizer and 0.67 mg/cm of drug content to use as a sample in following Experimental Examples. )>
- Example 4 Preparation of inventive plaster (4)
- Inventive plaster (4) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% monooleic acid sorbitan used as an epidermal permeation enhancer, 15 w% felbinac, 67 w% acrylic adhesive as a pressure sensitive adhesive, 3 w% 2 triethanolamine as a solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples.
- Example 5 Preparation of inventive plaster (5)
- Inventive plaster (5) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% oleic acid used as an epidermal permeation enhancer, 15 w% felbinac, 67 w% acrylic adhesive as a pressure sensitive adhesive, 3 w% triethanolamine as a 2 solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples.
- Example 6 Preparation of inventive plaster (6) > Inventive plaster (6) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting 15 w% oleylalcohol used as an epidermal permeation enhancer, 15 w% felbinac, 67 w% acrylic adhesive as a pressure sensitive adhesive, 3 w% triethanolamine as a 2 solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples. > Example 7: Preparation of inventive plaster (7)
- Inventive plaster (7) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting the mixture of 5 w% oleylalcohol and 10% monooleic acid sorbitane used as an epidermal permeation enhancer, 15 w% felbinac, 67 w% acrylic adhesive as a pressure sensitive adhesive, 3 w% triethanolamine as a solubilizer and 0.50 2 mg/cm of drug content to use as a sample in following Experimental Examples.
- Example 8 Preparation of inventive plaster (8) > Inventive plaster (8) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting the mixture of 15 w% monooleic acid sorbitane used as an epidermal permeation enhancer, 15 w% felbinac, 67 w% acrylic adhesive as a pressure sensitive 2 adhesive, 3 w% monoethanolamine as a solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples.
- Inventive plaster (9) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting the mixture of 15 w% monooleic acid sorbitane used as an epidermal permeation enhancer, 15 w% felbinac, 65 w% acrylic adhesive as a pressure sensitive 2 adhesive, 5 w% triethanolamine as a solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples.
- Example 10 Preparation of inventive plaster (10)
- Inventive plaster (10) was prepared through similar procedure to the procedure disclosed in above Comparative Example 1 except adopting the mixture of 15 w% monooleic acid sorbitane used as an epidermal permeation enhancer, 15 w% felbinac, 65 w acrylic adhesive as a pressure sensitive 2 adhesive, 5 w% monoethanolamine as a solubilizer and 0.50 mg/cm of drug content to use as a sample in following Experimental Examples.
- the inventive felbinac-containing plaster can provide with long lasting ant i-inflammatory effect, superior stability and adhering force to the conventional plasters therefore, it can be useful as an effective felbinac-containing plaster to treat and alleviate various inflammation and pain inconsistently. While the invention has been described with respect to the above specific embodiments, it should be recognized that various modification and changes might be made to the invention by those skilled in the art which also fall within the scope of the invention as defined in the appended claims.
Landscapes
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
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KR1020030080978A KR100552649B1 (ko) | 2003-11-17 | 2003-11-17 | 펠비낙 함유 소염진통용 플라스터 |
KR10-2003-0080978 | 2003-11-17 |
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WO2005046653A1 true WO2005046653A1 (fr) | 2005-05-26 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/KR2004/002965 WO2005046653A1 (fr) | 2003-11-17 | 2004-11-16 | Emplatre antiphlogistique et analgesique comprenant un compose de felbinac |
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KR (1) | KR100552649B1 (fr) |
WO (1) | WO2005046653A1 (fr) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006024339A2 (fr) * | 2004-09-03 | 2006-03-09 | Bouty S.P.A. | Timbre multicouche a liberation commandee pour une utilisation topique |
EP2098254A1 (fr) | 2008-03-06 | 2009-09-09 | Bayer MaterialScience AG | Colles médicales pour la chirurgie dotées de liaisons bioactives |
WO2010004784A1 (fr) | 2008-07-10 | 2010-01-14 | 株式会社J-オイルミルズ | Agent d'amélioration de goût pour aliments et boissons |
EP1951211B1 (fr) | 2005-10-24 | 2017-06-14 | Handok Inc. | Préparations transdermiques contenant des médicaments anti-inflammatoires non stéroïdiens hydrophobes |
CN107847487A (zh) * | 2015-07-27 | 2018-03-27 | 久光制药株式会社 | 含有阿塞那平的贴剂 |
Citations (5)
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US5505956A (en) * | 1992-11-30 | 1996-04-09 | Pacific Chemical Co., Ltd. | Medicinal adhesive for percutaneous administration |
JPH10114646A (ja) * | 1996-10-08 | 1998-05-06 | Toko Yakuhin Kogyo Kk | 皮膚低刺激性経皮吸収貼付剤 |
WO1998024423A1 (fr) * | 1996-12-06 | 1998-06-11 | Hisamitsu Pharmaceutical Co., Inc. | Timbre contenant du felbinac |
EP1072261A2 (fr) * | 1999-07-30 | 2001-01-31 | Hisamitsu Pharmaceutical Co., Inc. | Timbre contenant du felbinac |
JP2002020274A (ja) * | 2000-06-12 | 2002-01-23 | San-A Seiyaku Kk | 非ステロイド性消炎鎮痛剤の外用貼付剤および外用貼付薬 |
-
2003
- 2003-11-17 KR KR1020030080978A patent/KR100552649B1/ko not_active IP Right Cessation
-
2004
- 2004-11-16 WO PCT/KR2004/002965 patent/WO2005046653A1/fr active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US5505956A (en) * | 1992-11-30 | 1996-04-09 | Pacific Chemical Co., Ltd. | Medicinal adhesive for percutaneous administration |
JPH10114646A (ja) * | 1996-10-08 | 1998-05-06 | Toko Yakuhin Kogyo Kk | 皮膚低刺激性経皮吸収貼付剤 |
WO1998024423A1 (fr) * | 1996-12-06 | 1998-06-11 | Hisamitsu Pharmaceutical Co., Inc. | Timbre contenant du felbinac |
EP1072261A2 (fr) * | 1999-07-30 | 2001-01-31 | Hisamitsu Pharmaceutical Co., Inc. | Timbre contenant du felbinac |
JP2002020274A (ja) * | 2000-06-12 | 2002-01-23 | San-A Seiyaku Kk | 非ステロイド性消炎鎮痛剤の外用貼付剤および外用貼付薬 |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006024339A2 (fr) * | 2004-09-03 | 2006-03-09 | Bouty S.P.A. | Timbre multicouche a liberation commandee pour une utilisation topique |
WO2006024339A3 (fr) * | 2004-09-03 | 2006-08-17 | Bouty S P A | Timbre multicouche a liberation commandee pour une utilisation topique |
EP1951211B1 (fr) | 2005-10-24 | 2017-06-14 | Handok Inc. | Préparations transdermiques contenant des médicaments anti-inflammatoires non stéroïdiens hydrophobes |
EP1951211B2 (fr) † | 2005-10-24 | 2020-06-24 | Handok Inc. | Préparations transdermiques contenant des médicaments anti-inflammatoires non stéroïdiens hydrophobes |
EP2098254A1 (fr) | 2008-03-06 | 2009-09-09 | Bayer MaterialScience AG | Colles médicales pour la chirurgie dotées de liaisons bioactives |
WO2010004784A1 (fr) | 2008-07-10 | 2010-01-14 | 株式会社J-オイルミルズ | Agent d'amélioration de goût pour aliments et boissons |
CN107847487A (zh) * | 2015-07-27 | 2018-03-27 | 久光制药株式会社 | 含有阿塞那平的贴剂 |
US20190000775A1 (en) * | 2015-07-27 | 2019-01-03 | Hisamitsu Pharmaceutical Co., Inc. | Asenapine-containing patch |
EP3329915A4 (fr) * | 2015-07-27 | 2019-03-27 | Hisamitsu Pharmaceutical Co., Inc. | Patch adhésif contenant de l'asénapine |
TWI677352B (zh) * | 2015-07-27 | 2019-11-21 | 日商久光製藥股份有限公司 | 含有阿申那平(asenapine)之貼附劑 |
US10806705B2 (en) | 2015-07-27 | 2020-10-20 | Hisamitsu Pharmaceutical Co., Inc. | Asenapine-containing patch |
CN107847487B (zh) * | 2015-07-27 | 2021-11-02 | 久光制药株式会社 | 含有阿塞那平的贴剂 |
Also Published As
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KR100552649B1 (ko) | 2006-02-20 |
KR20050047194A (ko) | 2005-05-20 |
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