AU5729999A - Active ingredient support in the form of a film - Google Patents
Active ingredient support in the form of a film Download PDFInfo
- Publication number
- AU5729999A AU5729999A AU57299/99A AU5729999A AU5729999A AU 5729999 A AU5729999 A AU 5729999A AU 57299/99 A AU57299/99 A AU 57299/99A AU 5729999 A AU5729999 A AU 5729999A AU 5729999 A AU5729999 A AU 5729999A
- Authority
- AU
- Australia
- Prior art keywords
- film
- active substance
- shaped
- particles
- carrier according
- 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
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
-
- 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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/009—Sachets, pouches characterised by the material or function of the envelope
-
- 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
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- 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
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
-
- 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
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0065—Forms with gastric retention, e.g. floating on gastric juice, adhering to gastric mucosa, expanding to prevent passage through the pylorus
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
-
- 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
- A61K9/7007—Drug-containing films, membranes or sheets
Description
Film-shaped active substance carriers The invention relates to a film-shaped active substance carrier with particles of an active substance-containing substrate, which particles can be applied to the surface thereof. Administration forms to be applied in the oral region and on the mucous membranes thereof are known. US 3,444,858 describes medicament strips based on a gelatin like material. Already in 1937, film-shaped medicaments were described in the "New England Journal of Medicine", volume 289, pages 533 to 535. From DE-OS 24 49 865 are known medicinal active substance carriers in the form of films containing, side by side, different active substances and active substance concentrations. EP 0 216 762 describes a water-soluble film of starch, gelatin, glycerin or sorbite which is coated by means of a roll coating process. It is mentioned in this connection that these administration forms can also be produced for chemical reagents, flavourings, etc. Canadian patent application 492 040 describes a process for making film-shaped preparations using active substances, along with gelatin or agar, gluten, carboxyvinyl polymer, polyvalent alcohol, a vegetable mucilage, or wax and water. EP 0 460 588 discloses a formulation suitable for the manufacture of film-shaped systems. Here, a preparation of 20 to 60%-wt. of film former, 2 to 40%-wt. of gel former, 0.1 to 35%-wt of active substance and maximally 40%-wt. of an inert filler is of particular advantage. Among other substances, polyvinyl alcohol is mentioned as a gel former. According to DE-OS 36 30 603 it is particularly advantageous to apply a flat-shaped dosage form to a carrier material, which is formed as a release film, in such a manner that it can be peeled off in doses.
2 US 4,128,445 and US 4,197,289 discuss possible technical solutions of loading carrier material with active substance. They describe loading processes in dry and moist environment, which aim at attaining a uniform distribution of active substances on these layers, or can be carried out making use of electrostatics. US Re 31764 discloses a detailed description of possibilities of applying pharmaceutical active substances on flat sub strates in drops. In this connection the document describes mechanisms of piezoelectrical application of active sub stances with the aid of electrical fields. US 5,089,307 describes a hot-sealable, edible film based on water-soluble polysaccharides, polyvalent alcohols and water. However, only food applications but not medicinal appli cations are described therein. From US 5,714,007 it is known to supply surfaces of pharmaceutical formulations with pulverulent active sub stances. To this end, active substance loading of planar layers is carried through by means of electrostatic charging of active substance particles, with the active substance carrier having opposite charge, said loading being controlled by voltage, polarity or duration. US 4,851,394 describes edible films based on glucomannane and glycerin as a covering of soft capsules or as food packages which dissolve when being consumed. US 5,232,704 discloses oral pharmaceutical forms wherein a lifting force caused by the generation of gas brought about by admission of liquid is used as a means. for attaining a prolonged retention time in the stomach with the aim of achieving a prolonged duration of action. US 5,047,244 describes film-shaped systems which, advantageously, have a two-layer structure of a water swellable layer and a water-insoluble barrier layer. The document reports on the use of polymers such as polyethylene glycol, the use of colloidal silicon dioxide, bioadhesive, 3 e.g. carboxyfunctional, polymers, polyvinyl alcohol and other auxiliaries. The above-described preparations, however, do not meet the below listed requirements of pharmaceutical administration forms of the kind mentioned at the outset, or they meet these requirements only in a very dissatisfactory manner. Said requirements comprise: - it must be possible to prepare the active substance preparation in an extremely accurate and in a precisely reproducible manner; - the finished administration form must contain the active substance unchangeably as to the amount and quality thereof, and it is to have a the desired mechanical stability; - the administration forms must release the active substance to the organism in a predetermined manner, not immediately and uncontrollably, but evenly and over a prolonged period of time; - in the case of oral application, the retention time in the stomach must be increased in accordance with a desired duration of action; - the dissolution rate of slightly soluble active substance components should be increased; - where film pieces are used as a finished administration form for oral application, these should retain their flat shape and avoid curling, such curling being a phenomenon frequently to be expected in the case of cast films. These requirements are not satisfactorily met by the systems and formulations of the prior art mentioned. Consequently, the invention has the object of providing a film-shaped 4 active substance carrier of the kind mentioned in the introductory portion of Claim 1 which enables both an accurate and a precisely reproducible active substance dosage as well as an accurate and a precisely reproducible active substance release at a predetermined delivery rate, and which contains the active substance, protected against premature detachment, on or in a mechanically stable film-shaped active substance carrier. This object is achieved by the invention in a film-shaped active substance carrier of the kind mentioned initially in that the particles of the active substance-containing substrate are fixedly connected with the said substrate. One embodiment of the invention provides for the particles to be fixed on the substrate with the aid of a solvent. In this case the anchoring of the particles on the carrier film is effected by preliminary interaction with moisture or solvent vapor, or under action of pressure and/or temperature. One advantageous embodiment of the invention makes use of the fact that by applying a further film-shaped layer one achieves an encapsulation of the drug particles. Application of this additional layer can be effected by calendering with or without the use of solvent or heat. It is also of advantage that by using fusible particles of an active substance-containing preparation, the adhesion of the particles on or in the carrier layer can be optimally realized. In this embodiment of the film-shaped active substance carrier it is of essential importance with regard to the invention that the further film-shaped layer is water vapour-diffusible. Here, the second film-shaped layer applied provides for additional protection of the particles applied to the surface of a carrier, and when selecting a suitable film the rate of active substance release is controlled by reason of the fact that it is possible to adjust the active substance release characteristics, which characteristics can 5 be predetermined in the process and which, in particular, are retarded. When in this process the two films which are used for lamination are sealed upon each other at their edge contour, it is possible - by employing gas-generating components in, for example, aqueous environment - to use the laminate as a gas-filled, floatable pouch in the stomach as a gastroretentive system. A further retardation of the active substance release can be achieved by a specific embodiment of the invention in that at least one further film-shaped body is contained in the space of the active substance carrier, which space is inflated due to the generation of gas, on whose surface are present active substance-containing particles which are fixedly connected with the said body. Furthermore, additional film-shaped bodies may be present in the cavity of the active substance carrier which are adapted as auxiliary substance carriers for the generation of gas. The use of the film-shaped active substance carrier is provided for as an administration form for cosmetic, pharmaceutical or food-technological products. Further details and advantages of the invention will become evident from the following explanation of some of the examples of embodiments schematically shown in the drawings. The drawings show: Figure 1 to Figure 6: sectional and side views of different but similar embodiments of film-shaped active substance carriers according to the invention. Figure 1: a sectional view of a film-shaped active substance carrier (2) provided with particles (1) of an active substance-containing substrate, which particles are fixedly 6 anchored on the carrier. When using slightly soluble active substances it is possible here to employ the measure of homogeneously applying to the surface a micronized form of the active substance at particle sizes of below 50 pm, preferably below 5 pm, and - avoiding agglomeration - fixing the same on the surface. In this case, a base may be chosen for the film-shaped drug carrier which is freely soluble in water. Figure 2 shows another embodiment of the film-shaped active substance carrier, with active substance particles (1), the film-shaped carrier (2) and a further film-shaped carrier (3) laminated thereon. Figure 3 shows an alternative embodiment of the film-shaped active substance carrier (2), with active substance particles (1) fixedly connected with the surface thereof, which active substance carrier (2) is covered or encapsulated with a film shaped layer (3), thus forming a cavity (4). According to Figure 4 the film-shaped active substance carrier (2) and the film-shaped layer (3) covering said carrier form a cavity (4) wherein an additional film-shaped element (2'), comprising active substance particles (1) fixed on the surface thereof, is embedded. In the cavity (4) are provided film-shaped auxiliary substance carriers (5, 6) for generation of gas. To render the latter activatable by admission of moisture, the film-shaped layer (3) is formed using water vapour-diffusible material. The active substance carrier (2) may be provided with active substance particles fixed on the surface thereof. As shown in Figure 5, a further alternative embodiment of the device according to the invention is provided with a film shaped active substance carrier (2) and a water vapour diffusible layer (3), forming a cavity (4) which contains 7 film-shaped active substance carriers (5, 6). The active substance particles (1) are fixed on the inner surfaces of the layers (2, 3). Figure 6 shows the separation of a strand consisting of layers (2, 3) and provided with active substance particles (1), using a separating device (7). The drug carriers (2, 2') shown in Figures 1 to 6 consist of a film of film-forming materials such as, for example, polyvinyl alcohol, preferably in partially hydrolized form, wherein between 1 and 20%, particularly preferred 12%, of the hydroxyl groups are replaced by acetyl groups, of cellulose derivatives, gelatin, pullulan or other saccharides, vegetable gums and polyvinylpyrrolidone. Furthermore, sugar, glucose, sorbite, polyethylene glycol and other water-soluble additives may advantageously be added to regulate the dissolution properties. Additives of up to 30%-wt. of a surfactant can improve the wetting to the active substance containing particles (1). Adding up to 40%-wt. of a filler does not eliminate the advantages of the invention and is likewise suitable for modification of the dissolution properties. Without claiming to be exhaustive, suitable substances for this purpose are silicon dioxide, titanium dioxide, calcium carbonate, calcium sulfate, calcium phosphate, talcum or mixtures of these substances. To improve acceptance, it is also possible to add flavours which advantageously form a drop-shaped internal phase in the layer. Furthermore, flavour-enhancing substances such as sodium saccharinate, other sweeteners, salt or sugar derivatives can be used to improve the impression of taste, such as also, for example, low-molecular organic acids, for example malic acid, adipic acid or citric acid. Further, stabilizers such as antioxidants improve the shelf-life of the adhering active substance particles.
8 These may consist of the above-mentioned base components of the film itself but also of more lipophile, e.g. wax- or resin-like, portions. Thermoplastic components, as well as water-soluble polymers such as polyethylene, are suitable for embedding after application onto a carrier film. Typically the active substances may be applied to a carrier in pure and optionally in micronized form. The film-shaped products or initial products preferably have a thickness of 20 to 300 pm; their size is advantageously 0.5 to 8 cm 2 . Through the application according to the invention of a second film-shaped layer (3) to an active substance carrier (2) it is possible to protect and encapsulate the particles (1) applied on the surface. Depending on the base material as well as the sensitivity to temperature, this can be effected by hot-calendering, bonding with the aid of solvents, or other methods known to those skilled in the art. By further processing, for example by means of contour rolls or similar shaping devices, the film laminate can obtain a desired geometrical contour, for example a shape suitable for filling into capsules. In this manner, it is possible to obtain, for example, markedly delayed active substance release characteristics. If two films intended for lamination are sealed with each other at the edge contour, it is thereby possible to achieve further special effects. On the one hand, it is thereby possible to achieve an extreme delay of the active substance release rate, and on the other hand the laminate can be used as a gastroretentive therapeutic product in the stomach or the intestinal tract by employing gas-generating components in the interior space of 9 a device according to the invention which is shaped as a pouch and has water vapour-diffusible layers. The film-shaped active substance carrier according to the invention has a wide range of applications, it can be produced in industrial production processes with high outputs at moderate costs, and it solves the task mentioned at the outset in an optimal manner.
Claims (11)
1. Film-shaped active substance carrier with particles of an active substance-containing substrate, which particles can be applied to the surface of said carrier, characterized in that said particles are fixedly connected with the surface of the film-shaped active substance-carrier or, respectively, are embedded therein.
2. Film-shaped active substance carrier according to Claim 1, characterized in that the particles are fixed thereon with the aid of a solvent.
3. Film-shaped active substance carrier according to Claim 1, characterized in that the particles are fixed thereon under action of pressure and/or temperature.
4. Film-shaped active substance carrier according to one or more of Claims 1 - 3, characterized in that its surface, which is enriched with active substance-containing particles, is covered by a further film-shaped layer.
5. Film-shaped active substance carrier according to Claim 4, characterized in that the further film-shaped layer is water vapour-diffusible.
6. Film-shaped active substance carrier according to one or more of Claims 1 to 5, characterized in that the two film shaped layers form a closed cavity around the active substance-containing particles, which cavity encloses a gas filling.
7. Film-shaped active substance carrier according to Claim 6, characterized in that the gas filling is the product of gas-generating reagents contained in the cavity which are 11 activatable under influence of moisture, temperature and/or light.
8. Film-shaped active substance carrier according to one or more of Claims 1 to 7, characterized in that at least one further film-shaped body is contained in the cavity, which body has active substance-containing particles on its surface which are fixedly connected with the film-shaped body.
9. Film-shaped active substance carrier according to one or more of Claims 1 to 8, characterized in that the cavity contains film-shaped bodies which are formed as auxiliary substance carriers for auxiliary substances for gas generation.
10. Film-shaped active substance carrier according to Claim 1, characterized in that particles of a slightly soluble active substance are applied thereto which have a particle size of below 50 pm, preferably below 5 pm.
11. The use of the film-shaped active substance carrier as an administration form for cosmetic, pharmaceutical or food technological products.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19837073 | 1998-08-17 | ||
DE19837073A DE19837073A1 (en) | 1998-08-17 | 1998-08-17 | Foil-shaped drug carriers |
PCT/EP1999/005549 WO2000010539A1 (en) | 1998-08-17 | 1999-07-31 | Active ingredient support in the form of a film |
Publications (1)
Publication Number | Publication Date |
---|---|
AU5729999A true AU5729999A (en) | 2000-03-14 |
Family
ID=7877657
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU57299/99A Abandoned AU5729999A (en) | 1998-08-17 | 1999-07-31 | Active ingredient support in the form of a film |
Country Status (17)
Country | Link |
---|---|
EP (1) | EP1109541B8 (en) |
JP (2) | JP5184725B2 (en) |
KR (1) | KR100550890B1 (en) |
CN (1) | CN1312710A (en) |
AR (1) | AR021768A1 (en) |
AT (1) | ATE306912T1 (en) |
AU (1) | AU5729999A (en) |
BR (1) | BRPI9913444B8 (en) |
CA (1) | CA2339836C (en) |
DE (2) | DE19837073A1 (en) |
DK (1) | DK1109541T3 (en) |
ES (1) | ES2252968T3 (en) |
IL (2) | IL141399A0 (en) |
MX (1) | MXPA01001402A (en) |
PL (1) | PL346145A1 (en) |
TR (1) | TR200100564T2 (en) |
WO (1) | WO2000010539A1 (en) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19646392A1 (en) | 1996-11-11 | 1998-05-14 | Lohmann Therapie Syst Lts | Preparation for use in the oral cavity with a layer containing pressure-sensitive adhesive, pharmaceuticals or cosmetics for dosed delivery |
DE10032456A1 (en) * | 2000-07-04 | 2002-01-31 | Lohmann Therapie Syst Lts | Rapidly disintegrating dosage form for the release of active substances in the mouth or in the body cavities |
US8268333B2 (en) | 2001-04-24 | 2012-09-18 | Lintec Corporation | Orally administered agent and an orally administered agent/supporting substrate complex |
JP4993652B2 (en) * | 2004-03-31 | 2012-08-08 | リンテック株式会社 | Oral administration |
DE10224607B4 (en) * | 2002-06-04 | 2008-03-13 | Lts Lohmann Therapie-Systeme Ag | Film-form, disintegratable preparations for drug release and process for their preparation |
AU2008238634B2 (en) * | 2007-03-30 | 2013-01-17 | Lintec Corporation | Film-like orally administered medication and manufacturing method therefor |
WO2010086989A1 (en) | 2009-01-29 | 2010-08-05 | 日東電工株式会社 | Intraoral film-shaped base and preparation |
JP2011207847A (en) * | 2010-03-30 | 2011-10-20 | Nitto Denko Corp | Film-form preparation and method for producing the same |
JP5751868B2 (en) | 2010-03-30 | 2015-07-22 | 日東電工株式会社 | Film-form preparation and method for producing the same |
JP5841433B2 (en) | 2012-01-11 | 2016-01-13 | 日東電工株式会社 | Intraoral film-form base and preparation |
CA2937049C (en) | 2013-12-16 | 2024-01-16 | The University Of British Columbia | Self-fueled particles for propulsion through flowing aqueous fluids |
JP2015154716A (en) * | 2014-02-19 | 2015-08-27 | 日本合成化学工業株式会社 | edible film |
US11697904B2 (en) | 2017-01-27 | 2023-07-11 | The Procter & Gamble Company | Active agent-containing articles that exhibit consumer acceptable article in-use properties |
US11697906B2 (en) | 2017-01-27 | 2023-07-11 | The Procter & Gamble Company | Active agent-containing articles and product-shipping assemblies for containing the same |
US11697905B2 (en) | 2017-01-27 | 2023-07-11 | The Procter & Gamble Company | Active agent-containing articles that exhibit consumer acceptable article in-use properties |
WO2018140472A1 (en) * | 2017-01-27 | 2018-08-02 | The Procter & Gamble Company | Active agent-containing articles that exhibit consumer acceptable article in-use properties |
DE102017127434A1 (en) * | 2017-11-21 | 2019-05-23 | Lts Lohmann Therapie-Systeme Ag | Pocket-shaped oral-release films with high drug loading |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US31764A (en) * | 1861-03-19 | Gearing eor threshing-machines | ||
ZA767136B (en) * | 1975-12-15 | 1977-10-26 | Hoffmann La Roche | Novel dosage form |
US4197289A (en) * | 1975-12-15 | 1980-04-08 | Hoffmann-La Roche Inc. | Novel dosage forms |
AU514195B2 (en) * | 1975-12-15 | 1981-01-29 | F. Hoffmann-La Roche & Co. | Dosage form |
US4451260A (en) * | 1982-03-26 | 1984-05-29 | Minnesota Mining And Manufacturing Company | Sustained release oral medicinal delivery device |
EP0283474A1 (en) * | 1985-10-09 | 1988-09-28 | Desitin Arzneimittel GmbH | Process for producing an administration or dosage form of drugs, reagents or other active ingredients |
JPS62207208A (en) * | 1986-03-07 | 1987-09-11 | Teijin Ltd | Film-shaped, gradually releasing oral preparation |
US4812315A (en) * | 1987-05-14 | 1989-03-14 | Tarabishi M Hisham | Diet pills |
IL87710A (en) * | 1987-09-18 | 1992-06-21 | Ciba Geigy Ag | Covered floating retard form for controlled release in gastric juice |
US4900552A (en) * | 1988-03-30 | 1990-02-13 | Watson Laboratories, Inc. | Mucoadhesive buccal dosage forms |
KR970005574B1 (en) * | 1994-08-24 | 1997-04-17 | 현대전자산업 주식회사 | Noise attenuation output buffer |
EP0961611B1 (en) * | 1997-01-14 | 2002-03-27 | LTS Lohmann Therapie-Systeme AG | Expandable gastro-retentive therapeutic system with controlled active substance release in the gastro-intestinal tract |
-
1998
- 1998-08-17 DE DE19837073A patent/DE19837073A1/en not_active Withdrawn
-
1999
- 1999-07-31 CN CN99809709A patent/CN1312710A/en active Pending
- 1999-07-31 PL PL99346145A patent/PL346145A1/en unknown
- 1999-07-31 WO PCT/EP1999/005549 patent/WO2000010539A1/en active IP Right Grant
- 1999-07-31 KR KR1020017001972A patent/KR100550890B1/en active IP Right Grant
- 1999-07-31 EP EP99944317A patent/EP1109541B8/en not_active Expired - Lifetime
- 1999-07-31 AT AT99944317T patent/ATE306912T1/en active
- 1999-07-31 IL IL14139999A patent/IL141399A0/en active IP Right Grant
- 1999-07-31 JP JP2000565861A patent/JP5184725B2/en not_active Expired - Lifetime
- 1999-07-31 BR BRPI9913444A patent/BRPI9913444B8/en not_active IP Right Cessation
- 1999-07-31 MX MXPA01001402A patent/MXPA01001402A/en unknown
- 1999-07-31 CA CA002339836A patent/CA2339836C/en not_active Expired - Lifetime
- 1999-07-31 AU AU57299/99A patent/AU5729999A/en not_active Abandoned
- 1999-07-31 DK DK99944317T patent/DK1109541T3/en active
- 1999-07-31 TR TR2001/00564T patent/TR200100564T2/en unknown
- 1999-07-31 DE DE59912684T patent/DE59912684D1/en not_active Expired - Lifetime
- 1999-07-31 ES ES99944317T patent/ES2252968T3/en not_active Expired - Lifetime
- 1999-08-13 AR ARP990104065A patent/AR021768A1/en unknown
-
2001
- 2001-02-12 IL IL141399A patent/IL141399A/en not_active IP Right Cessation
-
2010
- 2010-07-21 JP JP2010164089A patent/JP2010280679A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
EP1109541B1 (en) | 2005-10-19 |
KR100550890B1 (en) | 2006-02-10 |
CA2339836C (en) | 2007-07-17 |
IL141399A (en) | 2007-02-11 |
AR021768A1 (en) | 2002-08-07 |
DE19837073A1 (en) | 2000-03-23 |
CN1312710A (en) | 2001-09-12 |
JP2002523359A (en) | 2002-07-30 |
KR20010072683A (en) | 2001-07-31 |
BR9913444A (en) | 2001-09-25 |
ATE306912T1 (en) | 2005-11-15 |
TR200100564T2 (en) | 2001-07-23 |
PL346145A1 (en) | 2002-01-28 |
DK1109541T3 (en) | 2006-03-13 |
EP1109541A1 (en) | 2001-06-27 |
MXPA01001402A (en) | 2002-06-21 |
DE59912684D1 (en) | 2006-03-02 |
CA2339836A1 (en) | 2000-03-02 |
IL141399A0 (en) | 2002-03-10 |
EP1109541B8 (en) | 2005-12-28 |
JP2010280679A (en) | 2010-12-16 |
BR9913444B1 (en) | 2014-10-14 |
ES2252968T3 (en) | 2006-05-16 |
BRPI9913444B8 (en) | 2021-05-25 |
WO2000010539A1 (en) | 2000-03-02 |
JP5184725B2 (en) | 2013-04-17 |
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