CA2094913A1 - Transdermal nicotine absorption dosage unit and process - Google Patents
Transdermal nicotine absorption dosage unit and processInfo
- Publication number
- CA2094913A1 CA2094913A1 CA002094913A CA2094913A CA2094913A1 CA 2094913 A1 CA2094913 A1 CA 2094913A1 CA 002094913 A CA002094913 A CA 002094913A CA 2094913 A CA2094913 A CA 2094913A CA 2094913 A1 CA2094913 A1 CA 2094913A1
- Authority
- CA
- Canada
- Prior art keywords
- nicotine
- dosage unit
- layer
- transdermal
- adhesive layer
- 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.)
- Abandoned
Links
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 title claims abstract description 113
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 title claims abstract description 113
- 229960002715 nicotine Drugs 0.000 title claims abstract description 112
- 238000010521 absorption reaction Methods 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000000391 smoking effect Effects 0.000 claims abstract description 12
- 241000208125 Nicotiana Species 0.000 claims abstract description 10
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims abstract description 10
- 235000019788 craving Nutrition 0.000 claims abstract description 6
- 239000010410 layer Substances 0.000 claims description 53
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical group COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 34
- 239000012790 adhesive layer Substances 0.000 claims description 26
- -1 salicylate ester Chemical class 0.000 claims description 26
- 229960001860 salicylate Drugs 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 21
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 19
- 239000000853 adhesive Substances 0.000 claims description 17
- 239000011159 matrix material Substances 0.000 claims description 17
- 229960001047 methyl salicylate Drugs 0.000 claims description 17
- 230000001070 adhesive effect Effects 0.000 claims description 16
- 230000009102 absorption Effects 0.000 claims description 14
- 239000003623 enhancer Substances 0.000 claims description 6
- 239000000779 smoke Substances 0.000 claims description 6
- 239000004615 ingredient Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 description 24
- 238000000576 coating method Methods 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- 229940074928 isopropyl myristate Drugs 0.000 description 17
- 238000009472 formulation Methods 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 8
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 8
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 8
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000002998 adhesive polymer Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 230000004907 flux Effects 0.000 description 5
- 239000011888 foil Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 230000036556 skin irritation Effects 0.000 description 5
- LVYLCBNXHHHPSB-UHFFFAOYSA-N 2-hydroxyethyl salicylate Chemical compound OCCOC(=O)C1=CC=CC=C1O LVYLCBNXHHHPSB-UHFFFAOYSA-N 0.000 description 4
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 4
- 240000001812 Hyssopus officinalis Species 0.000 description 4
- 206010040880 Skin irritation Diseases 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 210000004072 lung Anatomy 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229940105132 myristate Drugs 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 4
- 231100000475 skin irritation Toxicity 0.000 description 4
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 150000005829 chemical entities Chemical class 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 231100000021 irritant Toxicity 0.000 description 3
- 239000002085 irritant Substances 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 150000003902 salicylic acid esters Chemical class 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 2
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 235000000072 L-ascorbyl-6-palmitate Nutrition 0.000 description 2
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 2
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229960004217 benzyl alcohol Drugs 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940005667 ethyl salicylate Drugs 0.000 description 2
- 229960002389 glycol salicylate Drugs 0.000 description 2
- 238000011587 new zealand white rabbit Methods 0.000 description 2
- PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 2
- 229940068196 placebo Drugs 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 231100000323 severe irritant Toxicity 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- KGYXYKHTHJPEBX-UHFFFAOYSA-N 5-ethoxy-3-ethoxycarbonyl-3-hydroxy-5-oxopentanoic acid Chemical compound CCOC(=O)CC(O)(CC(O)=O)C(=O)OCC KGYXYKHTHJPEBX-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 241001136792 Alle Species 0.000 description 1
- XFOUAXMJRHNTOP-UHFFFAOYSA-N Bacilysin Natural products CC(N)C(=O)NC(C(O)=O)CC1CCC(=O)C2OC12 XFOUAXMJRHNTOP-UHFFFAOYSA-N 0.000 description 1
- OWNRRUFOJXFKCU-UHFFFAOYSA-N Bromadiolone Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1C(O)CC(C=1C(OC2=CC=CC=C2C=1O)=O)C1=CC=CC=C1 OWNRRUFOJXFKCU-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 239000004821 Contact adhesive Substances 0.000 description 1
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
- 235000019227 E-number Nutrition 0.000 description 1
- 239000004243 E-number Substances 0.000 description 1
- 101000760663 Hololena curta Mu-agatoxin-Hc1a Proteins 0.000 description 1
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
- 206010025476 Malabsorption Diseases 0.000 description 1
- 208000004155 Malabsorption Syndromes Diseases 0.000 description 1
- 241000805973 Multilamina Species 0.000 description 1
- 241000282337 Nasua nasua Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241001415395 Spea Species 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000000774 hypoallergenic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000005265 lung cell Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940061319 ovide Drugs 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000005475 siliconizing Methods 0.000 description 1
- 231100000130 skin irritation / corrosion testing Toxicity 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000807 solvent casting Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 239000010409 thin film 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/465—Nicotine; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72112991A | 1991-06-26 | 1991-06-26 | |
| US721,129 | 1991-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2094913A1 true CA2094913A1 (en) | 1992-12-27 |
Family
ID=24896654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002094913A Abandoned CA2094913A1 (en) | 1991-06-26 | 1992-06-24 | Transdermal nicotine absorption dosage unit and process |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0544900A4 (enrdf_load_stackoverflow) |
| CN (1) | CN1067811A (enrdf_load_stackoverflow) |
| AU (1) | AU2294192A (enrdf_load_stackoverflow) |
| CA (1) | CA2094913A1 (enrdf_load_stackoverflow) |
| TW (1) | TW221970B (enrdf_load_stackoverflow) |
| WO (1) | WO1993000057A1 (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2166869A1 (en) * | 1993-07-09 | 1995-01-19 | Ooi Wong | Method and device for providing nicotine replacement therapy transdermally/transbuccally |
| JP5000932B2 (ja) * | 2005-06-21 | 2012-08-15 | 日東電工株式会社 | ニコチン含有経皮吸収製剤 |
| EP1774964B1 (en) * | 2005-10-13 | 2014-08-06 | Nitto Denko Corporation | Nicotine transdermal preparation and production method thereof |
| EP2377540A1 (en) * | 2010-03-31 | 2011-10-19 | Hexal AG | Transdermal patch containing 17-deacetyl norgestimate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4933184A (en) * | 1983-12-22 | 1990-06-12 | American Home Products Corp. (Del) | Menthol enhancement of transdermal drug delivery |
| CH672888A5 (enrdf_load_stackoverflow) * | 1986-11-07 | 1990-01-15 | Mepha Ag | |
| US4908213A (en) * | 1989-02-21 | 1990-03-13 | Schering Corporation | Transdermal delivery of nicotine |
| DE4020144A1 (de) * | 1990-06-25 | 1992-01-09 | Lohmann Therapie Syst Lts | Pflaster mit hohem gehalt an weichmachenden inhaltsstoffen |
-
1992
- 1992-06-04 TW TW81104426A patent/TW221970B/zh not_active IP Right Cessation
- 1992-06-24 AU AU22941/92A patent/AU2294192A/en not_active Abandoned
- 1992-06-24 CA CA002094913A patent/CA2094913A1/en not_active Abandoned
- 1992-06-24 EP EP19920915353 patent/EP0544900A4/en not_active Withdrawn
- 1992-06-24 WO PCT/US1992/005271 patent/WO1993000057A1/en not_active Application Discontinuation
- 1992-06-26 CN CN 92105287 patent/CN1067811A/zh not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0544900A4 (en) | 1993-12-01 |
| WO1993000057A1 (en) | 1993-01-07 |
| TW221970B (enrdf_load_stackoverflow) | 1994-04-01 |
| CN1067811A (zh) | 1993-01-13 |
| AU2294192A (en) | 1993-01-25 |
| EP0544900A1 (en) | 1993-06-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 19990625 |