CA1273871A - Transdermal nitroglycerin delivery system - Google Patents
Transdermal nitroglycerin delivery systemInfo
- Publication number
- CA1273871A CA1273871A CA000507068A CA507068A CA1273871A CA 1273871 A CA1273871 A CA 1273871A CA 000507068 A CA000507068 A CA 000507068A CA 507068 A CA507068 A CA 507068A CA 1273871 A CA1273871 A CA 1273871A
- Authority
- CA
- Canada
- Prior art keywords
- adhesive
- weight
- amount
- nitroglycerin
- sheet material
- 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
Links
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 title claims abstract description 121
- 239000000006 Nitroglycerin Substances 0.000 title claims abstract description 121
- 229960003711 glyceryl trinitrate Drugs 0.000 title claims abstract description 121
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims abstract description 18
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 16
- 206010020772 Hypertension Diseases 0.000 claims abstract description 11
- 206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 10
- 206010019280 Heart failures Diseases 0.000 claims abstract description 10
- 239000000853 adhesive Substances 0.000 claims description 140
- 230000001070 adhesive effect Effects 0.000 claims description 135
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 claims description 82
- 239000011248 coating agent Substances 0.000 claims description 58
- 238000000576 coating method Methods 0.000 claims description 58
- 239000000178 monomer Substances 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 54
- 229920001577 copolymer Polymers 0.000 claims description 47
- 229940068939 glyceryl monolaurate Drugs 0.000 claims description 43
- 239000000463 material Substances 0.000 claims description 40
- -1 fatty acid ester Chemical class 0.000 claims description 37
- 230000035515 penetration Effects 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 28
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 28
- 229940093471 ethyl oleate Drugs 0.000 claims description 28
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 27
- 229930195729 fatty acid Natural products 0.000 claims description 27
- 239000000194 fatty acid Substances 0.000 claims description 27
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 26
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 230000002209 hydrophobic effect Effects 0.000 claims description 11
- 239000008240 homogeneous mixture Substances 0.000 claims description 10
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 9
- 230000002035 prolonged effect Effects 0.000 claims description 9
- 230000037317 transdermal delivery Effects 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 239000003522 acrylic cement Substances 0.000 claims description 7
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 7
- 150000003926 acrylamides Chemical class 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 230000002708 enhancing effect Effects 0.000 claims description 6
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical class CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims description 6
- 230000003014 reinforcing effect Effects 0.000 claims description 6
- 229920001567 vinyl ester resin Chemical class 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 4
- 229920000058 polyacrylate Polymers 0.000 claims 3
- 230000001747 exhibiting effect Effects 0.000 claims 2
- 229920006243 acrylic copolymer Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 13
- 239000010410 layer Substances 0.000 abstract description 11
- 238000011282 treatment Methods 0.000 abstract description 4
- 239000004615 ingredient Substances 0.000 abstract description 3
- 230000009885 systemic effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 238000009472 formulation Methods 0.000 description 36
- 238000000034 method Methods 0.000 description 22
- 239000003814 drug Substances 0.000 description 15
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical group CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 11
- 230000004907 flux Effects 0.000 description 10
- 230000001186 cumulative effect Effects 0.000 description 8
- 238000009792 diffusion process Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 241000699666 Mus <mouse, genus> Species 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 5
- 239000012790 adhesive layer Substances 0.000 description 5
- 239000002998 adhesive polymer Substances 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 229920001684 low density polyethylene Polymers 0.000 description 5
- 239000004702 low-density polyethylene Substances 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000002390 adhesive tape Substances 0.000 description 4
- 239000003623 enhancer Substances 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000003961 penetration enhancing agent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ULBTUVJTXULMLP-UHFFFAOYSA-N butyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCC ULBTUVJTXULMLP-UHFFFAOYSA-N 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- PGYJSURPYAAOMM-UHFFFAOYSA-N 2-ethenoxy-2-methylpropane Chemical group CC(C)(C)OC=C PGYJSURPYAAOMM-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000184049 Chlosyne californica Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical group CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
- 239000004707 linear low-density polyethylene Substances 0.000 description 1
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 229940074369 monoethyl fumarate Drugs 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- 238000011580 nude mouse model Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US725,215 | 1985-04-19 | ||
| US06/725,215 US4751087A (en) | 1985-04-19 | 1985-04-19 | Transdermal nitroglycerin delivery system |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1273871A true CA1273871A (en) | 1990-09-11 |
Family
ID=24913627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000507068A Expired - Lifetime CA1273871A (en) | 1985-04-19 | 1986-04-18 | Transdermal nitroglycerin delivery system |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4751087A (enExample) |
| EP (1) | EP0219539B1 (enExample) |
| JP (1) | JP2588180B2 (enExample) |
| AT (1) | ATE76736T1 (enExample) |
| AU (1) | AU593810B2 (enExample) |
| CA (1) | CA1273871A (enExample) |
| CZ (1) | CZ390591A3 (enExample) |
| DE (1) | DE3685545T2 (enExample) |
| ES (1) | ES8802370A1 (enExample) |
| IE (1) | IE59725B1 (enExample) |
| IL (1) | IL78527A (enExample) |
| NZ (1) | NZ215746A (enExample) |
| WO (1) | WO1986006281A1 (enExample) |
| ZA (1) | ZA862945B (enExample) |
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| EP1889609B1 (en) * | 2006-07-18 | 2019-05-22 | Meda AB | Immune response modifier foam formulations |
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| JP5389668B2 (ja) | 2007-01-31 | 2014-01-15 | チョンシー ユー | 皮膚浸透率の非常に高い１Ｈ−イミダゾ［４，５−ｃ］キノリン−４−アミン及び関連化合物の正に荷電した水溶性プロドラッグ |
| DE102007021549A1 (de) | 2007-05-08 | 2008-11-13 | Novosis Ag | Transdermales therapeutisches System enthaltend mindestens zwei Opioide |
| US20090304776A1 (en) * | 2008-06-06 | 2009-12-10 | Totada Shantha | Transmucosal delivery of therapeutic agents and methods of use thereof |
| US7883487B2 (en) * | 2008-06-16 | 2011-02-08 | Shantha Totada R | Transdermal local anesthetic patch with injection port |
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| US20100221313A1 (en) * | 2008-12-01 | 2010-09-02 | Innovative Pharmaceuticals, Llc | Transdermal reservoir patch |
| MX2011001555A (es) | 2008-12-19 | 2011-04-14 | Graceway Pharmaceuticals Llc | Formulaciones de imiquimod de baja concentracion de dosis y regimenes de dosis de corta duracion para tratar queratosis actinica. |
| WO2011008324A1 (en) | 2009-07-13 | 2011-01-20 | Graceway Pharmaceuticals, Llc | Lower dosage strength imiquimod formulations and short dosing regimens for treating genital and perianal warts |
| PH12012500472A1 (en) * | 2009-09-07 | 2012-10-22 | Nipro Patch Co Ltd | Transdermally absorbable preparation |
| EP2584900B1 (en) | 2010-06-25 | 2019-01-02 | Medicis Pharmaceutical Corporation | Combination therapy with cryosurgery and low dosage strength imiquimod to treat actinic keratosis |
| US9849270B2 (en) | 2011-12-16 | 2017-12-26 | 3M Innovative Properties Company | Foldable adhesive composite dressing |
| CN104024358B (zh) | 2011-12-21 | 2016-02-10 | 3M创新有限公司 | 具有叠置衬片的粘合贴剂组件和系统及其制备方法 |
| WO2013096026A1 (en) | 2011-12-21 | 2013-06-27 | 3M Innovative Properties Company | Transdermal adhesive patch assembly with removable microneedle array and method of using same |
| US20140004204A1 (en) * | 2012-06-29 | 2014-01-02 | University Of South Florida | Biocompatible polyacrylate compositions and methods of use |
| WO2014058746A1 (en) | 2012-10-10 | 2014-04-17 | 3M Innovative Properties Company | Force-controlled applicator for applying a microneedle device to skin |
| US9789299B2 (en) | 2012-11-16 | 2017-10-17 | 3M Innovative Properties Company | Force-controlled applicator for applying a microneedle device to skin |
| KR101712413B1 (ko) | 2013-03-22 | 2017-03-06 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 카운터 조립체를 포함하는 마이크로니들 어플리케이터 |
| EP3003459B1 (en) | 2013-05-31 | 2018-06-20 | 3M Innovative Properties Company | Microneedle injection apparatus comprising an inverted actuator |
| JP6494602B2 (ja) | 2013-05-31 | 2019-04-03 | スリーエム イノベイティブ プロパティズ カンパニー | 二重カバーを備えるマイクロニードル注射装置 |
| EP3003457B8 (en) | 2013-05-31 | 2021-02-24 | Kindeva Drug Delivery L.P. | Microneedle injection and infusion apparatus |
| EP3033056B1 (en) | 2013-08-12 | 2020-01-15 | 3M Innovative Properties Company | Peptides for enhancing transdermal delivery |
| EP3020398A1 (en) | 2014-11-17 | 2016-05-18 | Nitto Denko Corporation | Compounds and formulations for reducing scarring |
| WO2017136303A1 (en) | 2016-02-05 | 2017-08-10 | 3M Innovative Properties Company | Transdermal drug delivery systems with fluorosilicone release liners |
| EP3287462A1 (en) | 2016-08-25 | 2018-02-28 | Nitto Denko Corporation | Isosorbide derivatives to treat bacterial biofilms |
| CN116829347A (zh) | 2021-01-13 | 2023-09-29 | 3M创新有限公司 | 用于与玻璃表面一起使用的制品 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3742951A (en) * | 1971-08-09 | 1973-07-03 | Alza Corp | Bandage for controlled release of vasodilators |
| DE2528516A1 (de) * | 1974-07-05 | 1976-01-22 | Sandoz Ag | Neue galenische zubereitung |
| DE2920500A1 (de) * | 1979-05-21 | 1980-11-27 | Boehringer Sohn Ingelheim | Pharmazeutische zubereitung in form eines polyacrylatfilmes |
| JPS5777617A (en) * | 1980-10-20 | 1982-05-15 | Nichiban Co Ltd | Plaster for cardiac disease |
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| JPS6059207B2 (ja) * | 1981-03-13 | 1985-12-24 | 日東電工株式会社 | 複合製剤の製法 |
| JPS58913A (ja) * | 1981-06-26 | 1983-01-06 | Nitto Electric Ind Co Ltd | 局所系医薬製剤 |
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| JPS61502760A (ja) * | 1984-07-24 | 1986-11-27 | キイ・フア−マシユ−テイカルズ・インコ−ポレイテツド | 粘着性経皮投与層 |
-
1985
- 1985-04-19 US US06/725,215 patent/US4751087A/en not_active Expired - Lifetime
-
1986
- 1986-04-09 NZ NZ215746A patent/NZ215746A/xx unknown
- 1986-04-16 IL IL78527A patent/IL78527A/xx not_active IP Right Cessation
- 1986-04-18 CA CA000507068A patent/CA1273871A/en not_active Expired - Lifetime
- 1986-04-18 WO PCT/US1986/000789 patent/WO1986006281A1/en not_active Ceased
- 1986-04-18 ZA ZA862945A patent/ZA862945B/xx unknown
- 1986-04-18 ES ES554144A patent/ES8802370A1/es not_active Expired
- 1986-04-18 EP EP86902978A patent/EP0219539B1/en not_active Expired - Lifetime
- 1986-04-18 IE IE103586A patent/IE59725B1/en not_active IP Right Cessation
- 1986-04-18 JP JP61502454A patent/JP2588180B2/ja not_active Expired - Lifetime
- 1986-04-18 AU AU57725/86A patent/AU593810B2/en not_active Expired
- 1986-04-18 DE DE8686902978T patent/DE3685545T2/de not_active Expired - Lifetime
- 1986-04-18 AT AT86902978T patent/ATE76736T1/de not_active IP Right Cessation
-
1991
- 1991-12-19 CZ CS913905A patent/CZ390591A3/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES554144A0 (es) | 1988-05-16 |
| ZA862945B (en) | 1987-12-30 |
| IL78527A0 (en) | 1986-08-31 |
| US4751087A (en) | 1988-06-14 |
| DE3685545T2 (de) | 1992-12-24 |
| JP2588180B2 (ja) | 1997-03-05 |
| IL78527A (en) | 1991-07-18 |
| IE861035L (en) | 1986-10-19 |
| EP0219539B1 (en) | 1992-06-03 |
| WO1986006281A1 (en) | 1986-11-06 |
| EP0219539A1 (en) | 1987-04-29 |
| ATE76736T1 (de) | 1992-06-15 |
| DE3685545D1 (de) | 1992-07-09 |
| CZ390591A3 (en) | 1993-07-14 |
| AU5772586A (en) | 1986-11-18 |
| JPS62502965A (ja) | 1987-11-26 |
| ES8802370A1 (es) | 1988-05-16 |
| NZ215746A (en) | 1989-08-29 |
| AU593810B2 (en) | 1990-02-22 |
| US4751087B1 (enExample) | 1993-03-02 |
| IE59725B1 (en) | 1994-03-23 |
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| MKEX | Expiry |