WO1998031348A1 - Acetylsalicylsäure enthaltendes transdermales therapeutisches system mit resorptionsverstärkung - Google Patents
Acetylsalicylsäure enthaltendes transdermales therapeutisches system mit resorptionsverstärkung Download PDFInfo
- Publication number
- WO1998031348A1 WO1998031348A1 PCT/EP1998/000013 EP9800013W WO9831348A1 WO 1998031348 A1 WO1998031348 A1 WO 1998031348A1 EP 9800013 W EP9800013 W EP 9800013W WO 9831348 A1 WO9831348 A1 WO 9831348A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- limonene
- acetylsalicylic acid
- therapeutic system
- dimethyl isosorbide
- transdermal therapeutic
- Prior art date
Links
Classifications
-
- 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
- A61K31/60—Salicylic acid; Derivatives thereof
- A61K31/612—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid
- A61K31/616—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid by carboxylic acids, e.g. acetylsalicylic acid
-
- 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
-
- 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
-
- 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
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- 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
- A61K9/70—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
- 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
- A61K9/7092—Transdermal patches having multiple drug layers or reservoirs, e.g. for obtaining a specific release pattern, or for combining different drugs
Definitions
- the invention relates to a transdermal therapeutic system containing acetylsalicylic acid with an essentially active substance and moisture impermeable back layer, an active substance reservoir and optionally a removable protective layer.
- TTS Transdermal therapeutic systems
- Acetylsalicylic acid is a relatively safe drug with a high therapeutic index. It is used as an anti-inflammatory drug in very high doses (over one gram per day), as an antipyretic / analgesic in medium doses (250-500 mg) and as a platelet aggregation inhibitor in low doses (30 to 150 mg per day). Acetylsalicylic acid is a substance that melts at a low temperature (approx. 139 ° C) and is already noticeably volatile at this temperature.
- Acetylsalicylic acid is susceptible to hydrolysis and transesterification due to the unstable ester grouping.
- stabilization methods have already been considered, such as elimination of water, alcohols and esters as possible reaction partners for a transesterification or saponification; Add acetic acid or acetic anhydride or adjust pH 2-3.
- dimethyl isosorbide is also mentioned as a stabilizing solvent.
- a major obstacle to the development of pharmaceutically active transdermal therapeutic systems containing acetylsalicylic acid is, moreover, the low permeability of the active substance through the skin compared to the high required daily therapeutic dose.
- Numerous permeation accelerators have therefore already been proposed as additives, such as azones, carboxylic acid esters and surface-active substances Etc.
- US Pat. No. 5,164,416 also specifies limonene as a permeation-enhancing substance for acetylsalicylic acid, but its use is then restricted to the simultaneous addition of a possibly irritating alkaline additive. Furthermore, the permeation rates achievable for acetylsalicylic acid - following this teaching - are not yet sufficiently high.
- the transdermal therapeutic system of the type mentioned at the outset is essentially characterized by a content of limonene and Dimethyl isosorbide in a mixing ratio of at least 50:50 (g / g) limonene to dimethyl isosorbide in the active substance range.
- the principle according to the invention can be used both in matrix systems and in reservoir / membrane systems. It is also irrelevant which polymers, resins and possibly other additives are added, provided the formulation is only suitable for delivering the basic substances acetylsalicylic acid, limonene and dimethylisosorbide to the skin.
- all three characteristic feedstocks can be dispersed or dissolved in a solution of base polymers, the mixture can be coated on a suitable base, usually a siliconized thermoplastic film, and, after evaporation of the solvent components, possibly reinforced by the addition of heat , are covered with another film, which makes up the back of the transdermal therapeutic system.
- a suitable base usually a siliconized thermoplastic film
- another film which makes up the back of the transdermal therapeutic system.
- a two-layer matrix is formed from a skin-side layer which contains the active ingredient in dispersed or dissolved form and a second skin-facing layer which contains limonene and dimethyl isosorbide in the desired mixing ratio.
- these design variants are only the simplest of a number of possible system designs known to the person skilled in the art. Of course, matrix systems with more than two layers are possible and additional active ingredients can be provided if necessary.
- Suitable base polymers for the system according to the invention are in particular acrylate copolymers, styrene / diene copolymers, silicone polymers, mixtures of polyisobutylene with suitable thermoplastic resins. This list is far from complete, but does show the broad applicability of the principle according to the invention.
- the mixing ratio of limonene to dimethyl isosorbide is in particular in the range from 50:50 to 99: 1, preferably in the range from 85:15 to 95: 5 and especially in the range from 90:10.
- a limonene fraction which is of the order of magnitude of the acetylsalicyl acid concentration can expediently be provided.
- the mass is coated on a siliconized polyester film (100 ⁇ m thick) so that a layer of 150 g per m 2 basis weight is formed. Drying is gently achieved by storing in air for 10 hours at room temperature. A further film (polyester film 15 ⁇ m thick) is applied to this matrix by lamination and circular die-cuts of 20 cm 2 in size are produced with punch iron.
- transdermal therapeutic systems were obtained which, after the siliconized polyester film had been detached, could be applied directly to the skin in order to produce the desired therapeutic effect.
- a 2.54 cm 2 round fleece disc (cotton) is applied to the adhesive area of the laminate from (2). 8.5 mg of a mixture of 10% (g / g) dimethyl isosorbide and 90% (g / g) limonene, which had been saturated beforehand by stirring for 5 hours at room temperature and then filtering off with acetylsalicylic acid, are dripped onto the fleece disc.
- Laminate of (1) and fleece disc are covered on the adhesive side with layer (2) so that a sandwich made of polyester film (15 ⁇ m), 52 g / m 2 polyacrylate with acetylsalicylic acid, doped fleece disc 2.54 cm 2 and 93 g / m 2 Polyacrylate with acetylsalicylic acid is formed, which is still covered on the adhesive side by a protective film made of siliconized polyester.
- Example 3 (comparative example to example 2):
- Layers 1 and 2 are made according to example 2.
- a 2.54 cm 2 , round fleece disc (cotton) is applied to the adhesive area of the laminate from (2). 8.5 mg of pure dimethyl isosorbide, which had been saturated beforehand by stirring for 5 hours at room temperature and then filtering with acetylsalicylic acid, are dripped onto the nonwoven disk. Laminate from (1) and fleece disc are punched out in a pattern of 7.10 cm 2 analogously to Example 2. A permeation determination was also carried out on excised rat skin.
- Example 4 (Comparative example to Example 2)
- Layers 1 and 2 are made according to example 2.
- a 2.54 cm 2 round fleece disc (cotton) is applied to the adhesive area of the laminate from (2). 8.5 mg of pure limonene, which had been saturated with acetylsalicylic acid by stirring for 5 hours at room temperature and then filtering off, are dripped onto the nonwoven disk.
- Laminate from (1) and fleece disc are punched out in a pattern of 7.10 cm 2 analogously to Example 2.
- a permeation determination was also carried out on excised rat skin. After 48 hours, an average permeation of 253.3 ⁇ g / cm 2 acetylsalicylic acid was found.
- Example 5 (Comparative example to Example 2)
- Layers 1 and 2 are made according to example 2.
- a 2.54 cm 2 round fleece disc (cotton) is applied to the adhesive area of the laminate from (2). No medium is dripped on. Laminate from (1) and fleece disc are punched out in a pattern of 7.10 cm 2 analogously to Example 2. A permeation determination was also carried out on excised rat skin.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002277366A CA2277366A1 (en) | 1997-01-15 | 1998-01-03 | Transdermal, acetylsalicylic acid-containing therapeutic system with reinforced resorption |
JP53137698A JP2001508069A (ja) | 1997-01-15 | 1998-01-03 | 吸収性を高めたアセチルサリチル酸含有経皮吸収治療システム |
AU59862/98A AU726094B2 (en) | 1997-01-15 | 1998-01-03 | Acetylsalicylic acid-containing transdermal therapeutic system with absorption enhancement |
EP98902976A EP1023053A1 (de) | 1997-01-15 | 1998-01-03 | Acetylsalicylsäure enthaltendes transdermales therapeutisches system mit resorptionsverstärkung |
NO993435A NO993435D0 (no) | 1997-01-15 | 1999-07-12 | Transdermalt acetylsalicylsyre inneholdende terapeutisk system med forsterket resorpsjon |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19701059A DE19701059C2 (de) | 1997-01-15 | 1997-01-15 | Acetylsalicylsäure enthaltendes transdermales therapeutisches System mit Resorptionsverstärkung |
DE19701059.8 | 1997-01-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998031348A1 true WO1998031348A1 (de) | 1998-07-23 |
Family
ID=7817375
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/000013 WO1998031348A1 (de) | 1997-01-15 | 1998-01-03 | Acetylsalicylsäure enthaltendes transdermales therapeutisches system mit resorptionsverstärkung |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP1023053A1 (de) |
JP (1) | JP2001508069A (de) |
KR (1) | KR20000070228A (de) |
AU (1) | AU726094B2 (de) |
CA (1) | CA2277366A1 (de) |
DE (1) | DE19701059C2 (de) |
NO (1) | NO993435D0 (de) |
WO (1) | WO1998031348A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003511408A (ja) * | 1999-10-13 | 2003-03-25 | エルテーエス ローマン テラピー−ジステーメ アーゲー | アセチルサリチル酸および/またはサリチル酸投与用の経皮治療システム |
US8936813B2 (en) | 2001-11-01 | 2015-01-20 | Novartis Ag | Spray drying methods and related compositions |
IT202000014578A1 (it) * | 2020-06-18 | 2021-12-18 | Poli Md S R L | Dispositivo medicale comprendente acido acetil salicilico |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19949252B4 (de) * | 1999-10-13 | 2004-02-12 | Lts Lohmann Therapie-Systeme Ag | Verwendung eines superfiziellen therapeutischen Systems zur topischen Applikation von Acetylsalicylsäure zur Behandlung von Akne-Erkrankungen und Verfahren zu seiner Herstellung |
DE19959913A1 (de) * | 1999-12-11 | 2001-06-28 | Lohmann Therapie Syst Lts | Acetylsalicylsäure enthaltendes transdermales System zur Behandlung von Migräne |
KR100448469B1 (ko) * | 2001-10-26 | 2004-09-13 | 신풍제약주식회사 | 항염증제의 경피 조성물 및 장치 |
DE10338162B3 (de) † | 2003-08-20 | 2005-06-02 | Haldex Brake Products Gmbh | Verfahren zum Betreiben einer Druckluftbeschaffungsanlage eines Kraftfahrzeuges sowie Druckluftaufbereitungseinrichtung |
DE102005033543A1 (de) * | 2005-07-14 | 2007-01-18 | Grünenthal GmbH | Ein einen Duftstoff aufweisendes transdermales therapeutisches System |
DE102005050431A1 (de) * | 2005-10-21 | 2007-04-26 | Lts Lohmann Therapie-Systeme Ag | Transdermales therapeutisches System zur Verabreicherung lipophiler und/oder wenig hautpermeabler Wirkstoffe |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4228162A (en) * | 1979-07-09 | 1980-10-14 | Research Corporation | Dimethyl isosorbide in liquid formulation of aspirin |
US5164416A (en) * | 1989-02-03 | 1992-11-17 | Lintec Corporation | Transdermal therapeutic formulation containing a limonene |
DE4332094A1 (de) * | 1993-09-22 | 1995-03-23 | Lohmann Therapie Syst Lts | Lösemittelfrei herstellbares Wirkstoffpflaster |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4332093C2 (de) * | 1993-09-22 | 1995-07-13 | Lohmann Therapie Syst Lts | Transdermales therapeutisches System mit dem Wirkstoff Acetylsalicylsäure und Verfahren zu seiner Herstellung |
-
1997
- 1997-01-15 DE DE19701059A patent/DE19701059C2/de not_active Expired - Fee Related
-
1998
- 1998-01-03 EP EP98902976A patent/EP1023053A1/de not_active Withdrawn
- 1998-01-03 CA CA002277366A patent/CA2277366A1/en not_active Abandoned
- 1998-01-03 AU AU59862/98A patent/AU726094B2/en not_active Ceased
- 1998-01-03 JP JP53137698A patent/JP2001508069A/ja active Pending
- 1998-01-03 WO PCT/EP1998/000013 patent/WO1998031348A1/de not_active Application Discontinuation
- 1998-01-03 KR KR1019997006454A patent/KR20000070228A/ko not_active Application Discontinuation
-
1999
- 1999-07-12 NO NO993435A patent/NO993435D0/no not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4228162A (en) * | 1979-07-09 | 1980-10-14 | Research Corporation | Dimethyl isosorbide in liquid formulation of aspirin |
US5164416A (en) * | 1989-02-03 | 1992-11-17 | Lintec Corporation | Transdermal therapeutic formulation containing a limonene |
DE4332094A1 (de) * | 1993-09-22 | 1995-03-23 | Lohmann Therapie Syst Lts | Lösemittelfrei herstellbares Wirkstoffpflaster |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003511408A (ja) * | 1999-10-13 | 2003-03-25 | エルテーエス ローマン テラピー−ジステーメ アーゲー | アセチルサリチル酸および/またはサリチル酸投与用の経皮治療システム |
JP4938949B2 (ja) * | 1999-10-13 | 2012-05-23 | エルテーエス ローマン テラピー−ジステーメ アーゲー | アセチルサリチル酸および/またはサリチル酸投与用の経皮治療システム |
US8936813B2 (en) | 2001-11-01 | 2015-01-20 | Novartis Ag | Spray drying methods and related compositions |
IT202000014578A1 (it) * | 2020-06-18 | 2021-12-18 | Poli Md S R L | Dispositivo medicale comprendente acido acetil salicilico |
Also Published As
Publication number | Publication date |
---|---|
AU5986298A (en) | 1998-08-07 |
AU726094B2 (en) | 2000-11-02 |
NO993435L (no) | 1999-07-12 |
DE19701059C2 (de) | 2000-12-21 |
DE19701059A1 (de) | 1998-07-16 |
JP2001508069A (ja) | 2001-06-19 |
CA2277366A1 (en) | 1998-07-23 |
NO993435D0 (no) | 1999-07-12 |
KR20000070228A (ko) | 2000-11-25 |
EP1023053A1 (de) | 2000-08-02 |
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