CA2332110A1 - Biologically active composition - Google Patents
Biologically active composition Download PDFInfo
- Publication number
- CA2332110A1 CA2332110A1 CA002332110A CA2332110A CA2332110A1 CA 2332110 A1 CA2332110 A1 CA 2332110A1 CA 002332110 A CA002332110 A CA 002332110A CA 2332110 A CA2332110 A CA 2332110A CA 2332110 A1 CA2332110 A1 CA 2332110A1
- Authority
- CA
- Canada
- Prior art keywords
- biologically active
- active agent
- composition according
- carrier
- composition
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 135
- 239000000126 substance Substances 0.000 claims abstract description 103
- 239000013543 active substance Substances 0.000 claims abstract description 84
- 239000011159 matrix material Substances 0.000 claims abstract description 38
- 239000007787 solid Substances 0.000 claims abstract description 18
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 239000003814 drug Substances 0.000 claims description 56
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 29
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 13
- -1 mono- Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 230000005588 protonation Effects 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 238000007792 addition Methods 0.000 claims description 5
- 230000002776 aggregation Effects 0.000 claims description 5
- 238000004220 aggregation Methods 0.000 claims description 5
- 238000010494 dissociation reaction Methods 0.000 claims description 5
- 230000005593 dissociations Effects 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 210000004907 gland Anatomy 0.000 claims description 4
- 239000000021 stimulant Substances 0.000 claims description 4
- 230000000699 topical effect Effects 0.000 claims description 4
- 238000012384 transportation and delivery Methods 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- HJAJMZJYCFUYMA-UHFFFAOYSA-N 2-hydroxyacetic acid;prop-2-enoic acid Chemical compound OCC(O)=O.OC(=O)C=C HJAJMZJYCFUYMA-UHFFFAOYSA-N 0.000 claims description 2
- WTVNUJRNSNVFID-UHFFFAOYSA-N 2-hydroxypropanoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(O)C(O)=O WTVNUJRNSNVFID-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- 229920001651 Cyanoacrylate Polymers 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 150000003926 acrylamides Chemical class 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 229940111133 antiinflammatory and antirheumatic drug oxicams Drugs 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 239000003443 antiviral agent Substances 0.000 claims description 2
- 229940121357 antivirals Drugs 0.000 claims description 2
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 239000003246 corticosteroid Substances 0.000 claims description 2
- 229960001334 corticosteroids Drugs 0.000 claims description 2
- 230000036576 dermal application Effects 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 239000000262 estrogen Substances 0.000 claims description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 2
- 210000003630 histaminocyte Anatomy 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 210000002752 melanocyte Anatomy 0.000 claims description 2
- 239000003176 neuroleptic agent Substances 0.000 claims description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 230000028327 secretion Effects 0.000 claims description 2
- 239000007790 solid phase Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 150000004072 triols Chemical class 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 229940121375 antifungal agent Drugs 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 230000000063 preceeding effect Effects 0.000 claims 1
- 238000001556 precipitation Methods 0.000 abstract description 15
- 229940079593 drug Drugs 0.000 description 53
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 229960000282 metronidazole Drugs 0.000 description 20
- 230000004888 barrier function Effects 0.000 description 19
- 238000013459 approach Methods 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 11
- 238000009792 diffusion process Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 238000010586 diagram Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 230000035515 penetration Effects 0.000 description 8
- 210000003491 skin Anatomy 0.000 description 8
- 230000009471 action Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 229940002612 prodrug Drugs 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 230000004907 flux Effects 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 3
- 238000012377 drug delivery Methods 0.000 description 3
- 230000002500 effect on skin Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000000935 solvent evaporation Methods 0.000 description 3
- 238000002798 spectrophotometry method Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000994 depressogenic effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003405 preventing effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 229920000260 silastic Polymers 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000002525 ultrasonication Methods 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
- 244000287680 Garcinia dulcis Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000002821 anti-nucleating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000005331 crown glasses (windows) Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000012385 systemic delivery Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 238000011179 visual inspection Methods 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
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
-
- 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
-
- 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
- A61K9/08—Solutions
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9801705-6 | 1998-05-14 | ||
| SE9801705A SE9801705D0 (sv) | 1998-05-14 | 1998-05-14 | Biologically active composition |
| PCT/SE1999/000824 WO1999058109A1 (en) | 1998-05-14 | 1999-05-12 | Biologically active composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2332110A1 true CA2332110A1 (en) | 1999-11-18 |
Family
ID=20411319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002332110A Abandoned CA2332110A1 (en) | 1998-05-14 | 1999-05-12 | Biologically active composition |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1077677B1 (https=) |
| JP (1) | JP2002514588A (https=) |
| KR (1) | KR100766998B1 (https=) |
| CN (1) | CN1309554A (https=) |
| AT (1) | ATE252371T1 (https=) |
| AU (1) | AU742921B2 (https=) |
| CA (1) | CA2332110A1 (https=) |
| DE (2) | DE69912271T2 (https=) |
| DK (1) | DK1077677T3 (https=) |
| ES (1) | ES2155049T3 (https=) |
| GR (1) | GR20010300014T1 (https=) |
| HU (1) | HUP0102002A3 (https=) |
| IL (2) | IL139577A0 (https=) |
| NO (1) | NO20005725L (https=) |
| NZ (1) | NZ508074A (https=) |
| PL (1) | PL344221A1 (https=) |
| SE (1) | SE9801705D0 (https=) |
| TR (1) | TR200003588T2 (https=) |
| WO (1) | WO1999058109A1 (https=) |
| ZA (1) | ZA200006476B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003524652A (ja) * | 2000-02-29 | 2003-08-19 | ツァン，ツィエ | 改良された経皮薬剤パッチ |
| WO2005013939A1 (en) | 2003-08-06 | 2005-02-17 | Nirmal Mulye | Pharmaceutical composition containing water soluble drug |
| KR20090031726A (ko) | 2006-06-14 | 2009-03-27 | 닥터 레디스 레보러터리즈 리미티드 | 국소용 조성물 |
| WO2012028496A1 (de) * | 2010-08-31 | 2012-03-08 | Basf Se | Verzweigte polyester auf basis von zitronensäure sowie deren herstellung und verwendung |
| KR20140089478A (ko) * | 2011-01-13 | 2014-07-15 | 큐엘티 인코포레이티드 | 감광제의 국소 전달용 약학 조성물 및 그의 이용 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4940701A (en) * | 1984-01-25 | 1990-07-10 | Beecham Group P.L.C. | Topical drug release system |
| SE9502244D0 (sv) * | 1995-06-20 | 1995-06-20 | Bioglan Ab | A composition and a process for the preparation thereof |
| US5906830A (en) * | 1995-09-08 | 1999-05-25 | Cygnus, Inc. | Supersaturated transdermal drug delivery systems, and methods for manufacturing the same |
| GB2306885B (en) * | 1995-11-08 | 1999-07-14 | Reckitt & Colmann Prod Ltd | Supersaturated Pharmaceutical Compositions |
-
1998
- 1998-05-14 SE SE9801705A patent/SE9801705D0/xx unknown
-
1999
- 1999-05-12 IL IL13957799A patent/IL139577A0/xx active IP Right Grant
- 1999-05-12 NZ NZ508074A patent/NZ508074A/xx not_active IP Right Cessation
- 1999-05-12 DE DE69912271T patent/DE69912271T2/de not_active Expired - Lifetime
- 1999-05-12 HU HU0102002A patent/HUP0102002A3/hu unknown
- 1999-05-12 TR TR2000/03588T patent/TR200003588T2/xx unknown
- 1999-05-12 DE DE1077677T patent/DE1077677T1/de active Pending
- 1999-05-12 ES ES99927062T patent/ES2155049T3/es not_active Expired - Lifetime
- 1999-05-12 KR KR1020007012709A patent/KR100766998B1/ko not_active Expired - Fee Related
- 1999-05-12 JP JP2000547961A patent/JP2002514588A/ja active Pending
- 1999-05-12 WO PCT/SE1999/000824 patent/WO1999058109A1/en not_active Ceased
- 1999-05-12 CN CN99808549A patent/CN1309554A/zh active Pending
- 1999-05-12 EP EP99927062A patent/EP1077677B1/en not_active Expired - Lifetime
- 1999-05-12 PL PL99344221A patent/PL344221A1/xx unknown
- 1999-05-12 CA CA002332110A patent/CA2332110A1/en not_active Abandoned
- 1999-05-12 AT AT99927062T patent/ATE252371T1/de active
- 1999-05-12 AU AU44051/99A patent/AU742921B2/en not_active Ceased
- 1999-05-12 DK DK99927062T patent/DK1077677T3/da active
-
2000
- 2000-11-09 IL IL139577A patent/IL139577A/en not_active IP Right Cessation
- 2000-11-09 ZA ZA200006476A patent/ZA200006476B/xx unknown
- 2000-11-13 NO NO20005725A patent/NO20005725L/no not_active Application Discontinuation
-
2001
- 2001-04-30 GR GR20010300014T patent/GR20010300014T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0102002A3 (en) | 2002-12-28 |
| HUP0102002A2 (hu) | 2002-03-28 |
| ATE252371T1 (de) | 2003-11-15 |
| DK1077677T3 (da) | 2004-02-16 |
| JP2002514588A (ja) | 2002-05-21 |
| TR200003588T2 (tr) | 2001-06-21 |
| IL139577A0 (en) | 2002-02-10 |
| SE9801705D0 (sv) | 1998-05-14 |
| EP1077677B1 (en) | 2003-10-22 |
| GR20010300014T1 (en) | 2001-04-30 |
| AU742921B2 (en) | 2002-01-17 |
| ZA200006476B (en) | 2001-06-11 |
| WO1999058109A1 (en) | 1999-11-18 |
| ES2155049T1 (es) | 2001-05-01 |
| KR100766998B1 (ko) | 2007-10-15 |
| AU4405199A (en) | 1999-11-29 |
| NZ508074A (en) | 2003-01-31 |
| DE69912271D1 (de) | 2003-11-27 |
| CN1309554A (zh) | 2001-08-22 |
| DE69912271T2 (de) | 2004-08-26 |
| NO20005725L (no) | 2001-01-11 |
| KR20010052349A (ko) | 2001-06-25 |
| ES2155049T3 (es) | 2004-05-16 |
| EP1077677A1 (en) | 2001-02-28 |
| DE1077677T1 (de) | 2001-09-20 |
| PL344221A1 (en) | 2001-10-08 |
| NO20005725D0 (no) | 2000-11-13 |
| IL139577A (en) | 2007-07-04 |
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