WO2002030436A1 - Verfahren zur herstellung von phyllanthusextrakten - Google Patents
Verfahren zur herstellung von phyllanthusextrakten Download PDFInfo
- Publication number
- WO2002030436A1 WO2002030436A1 PCT/EP2001/011526 EP0111526W WO0230436A1 WO 2002030436 A1 WO2002030436 A1 WO 2002030436A1 EP 0111526 W EP0111526 W EP 0111526W WO 0230436 A1 WO0230436 A1 WO 0230436A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phyllanthus
- pharmaceutically acceptable
- drying
- added
- medicament
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/47—Euphorbiaceae (Spurge family), e.g. Ricinus (castorbean)
Definitions
- the invention relates to a method for extracting phyllanthus, wherein (a) extracting phyllanthus constituents with an ethanol / water mixture of 5-85% m / m, to which a heavy metal chelator is added in a concentration of 0.001-3% m / m; (b) the primary extract obtained in step (a) with (ba) Indian sterculia gum in a final concentration of 0.5-5.0% mm, based on the sum of the extractive substances, or (bb) one or more polymers and impendable and / or soluble substance (s) added and concentrated; and (c) drying the concentrated extract obtained in step (b).
- the process according to the invention leads to a particularly high yield of pharmacologically active plant constituents and is therefore of particular interest for therapeutic applications.
- the method according to the invention includes a filtration step of the primary extract. It is further preferred that a lipoid is added during the extraction process.
- the Phyllanthus is preferably Phyllanthus amarus.
- the invention also relates to medicaments which contain extracts obtained by the process according to the invention.
- the plant genus Phyllanthus belongs to the subfamily of Phyllanthoideae, which in turn belongs to the family of Euphorbiaceae.
- the genus Phyllanthus comprises a total of about 700 known species that are native to tropical and subtropical areas in Australia, China, the Philippines, Thailand, Indonesia, Burma, India, East and West Africa as well as North America, Mexico, Cuba, the Caribbean and Venezuela , Representatives of this genus are rarely found in the northern temperate zones. Plants of the genus Phyllanthus contain secondary plant substances that are subject to oxidative degradation processes under the influence of light, temperature, oxygen and heavy metals.
- hydrolyzable tannins should be mentioned, such as didehydrohexahydroxydiphenol amariin or geraniin, a quantity-dominating ellagitannin.
- Phyllanthus amarus Schumach et Thonn is an additional ingredient group (lignans), the phyllanthines, of which primarily phyllanthin and hypophyllanthin are to be mentioned; the former dominates in terms of volume.
- lignans lignans
- phyllanthines of which primarily phyllanthin and hypophyllanthin are to be mentioned; the former dominates in terms of volume.
- lignans lignans
- phyllanthines Common to the phyllanthines and ellagitannins is their antioxidative reactivity, which on the one hand characterizes them as important active ingredients and on the other hand as easily destructible.
- the phyllanthines preferably dissolve in organic solvents or mixtures of the latter with water. Both substance classes can be found in addition to a series of ubiquitous primary and secondary plant substances in aqueous preparations (infuse / decocte), as are common in traditional folk medicine. This may seem surprising to the non-specialist in the case of phyllanthines; However, this finding can easily be explained by the person skilled in the art, since plants contain diverse, solution-mediating substance mixtures. In relation to the solubility behavior of individual components, complex multi-substance mixtures may behave completely differently than would be expected for one ingredient alone.
- Extractives adhere to machine parts that are responsible for heat transfer (heatexchanger), stick, burn. Layers build up that cannot be protected from the evaporative cold of the evaporating solvent. In this way, secondary products of unknown activity are formed on the one hand and the loss of native substances results on the other.
- the active ingredient should be dry, in a solid state and in powder form. Pharmaceutically acceptable excipients that make this goal achievable may be used.
- the chemical, biological and physical properties of the active ingredient must be stable under suitable storage conditions.
- the active ingredient must be able to be integrated into a pharmaceutically acceptable pharmaceutical formulation (preferably film-coated tablet, capsule, dragee).
- the invention was therefore based on the object of providing a method which solves the problems discussed above.
- the present invention thus relates to a process for producing an extract from phyllanthus, wherein (a) extracting phyllanthus constituents with an ethanol / water mixture of 5-85% m / m, to which a heavy metal chelator is added in a concentration of 0.001-3% m / m is; (b) the primary extract obtained in step (a) with (ba) Indian sterculia gum in a final concentration of 0.5-5.0% mm, based on the sum of the extractive substances, or (bb) one or more polymers and impendable and / or soluble substance (s) added and concentrated; and (c) drying the concentrated extract obtained in step (b).
- the term "phyllanthus constituents" as used according to the invention includes all constituents of the entire plant, e.g. Leaves, bark, flowers, stems, seeds, fruits, branches, stems, roots, wood, and parts thereof. These Phyllanthus ingredients may have the same, similar or unrelated ingredients. Different Phyllanthus constituents can be used individually or together as well as different Phyllanthus constituents from different Phyllanthus species individually or combined with one another in the process according to the invention. "Several" Phyllanthus components is also to be understood as the entirety of the Phyllanthus components, for example in the form of whole plants. The phyllanthus components can be used in the process according to the invention after pretreatment or without pretreatment. Pretreatment includes, for example, processes such as drying, for example sheets. i
- the invention provides for the first time a process that provides reproducible and valid plant extracts in large-scale implementation, in which pharmacologically active plant components are essentially retained in active form.
- pharmacologically active plant components are essentially retained in active form.
- this phenomenon is due to the property of the polymer, on the one hand, to swell homogeneously in 45% m / m ethanol and, on the other hand, to be inert towards the ellagitannins.
- Pharmaceutically acceptable alternative polymers such as polyvinylpyrrolidones or hydroxypropyl, ethyl and methyl celluloses dissolve in 45% w / w ethanol, but lead to precipitation with ellagitannins, polymers of the gum arabic or tragacanth type cannot be hydrated in 45% w / w ethanol and fall out as resinous gums.
- an ethanol / water mixture of 35-45% m / m is used for the extraction in step (a).
- 35-45% m / m ethanol is preferred because with sufficient lipophilicity for optimal extraction, it allows the sterculia rubber to be directly protected.
- the heavy metal chelator is added in step (a) in a concentration of 0.1-1.0% m / m.
- the primary extract is mixed with Indian sterculia gum in a final concentration of 0.7-1.3% m / m.
- the substance (s) is a pharmaceutically acceptable polysaccharide / pharmaceutically acceptable polysaccharides in a final concentration of 2-50% m / m, based on the sum of the extractive substances.
- the final concentration of the polysaccharide (s) is in the range of 1-10% m / m.
- filtration is carried out after step (a) and before step (b) (a) with the primary extract obtained in step (a), the filter having an exclusion volume of 0.05-0.5 ⁇ m.
- Phyllanthus amarus contains as a natural product more or less frequently and in more or less pronounced concentration bacterial endospores, fungal spores, which cannot be reliably killed even with an alcoholic extraction method. Since a number of Phyllanthus amarus ingredients are known to be thermolabile, thermal processes, the intensity of which would reliably be sufficient to kill these spores, are out of the question for the removal of these contaminants.
- the extraction liquid obtainable after the first process step above with the addition of polybasic acids or their salts, preferably disodium hydrogen citrate, can be filtered, preferably ultrafiltered, without (or almost without) substance losses, the pore size being selected so that it can pass through the spores are excluded due to their size.
- polybasic acids or their salts preferably disodium hydrogen citrate
- the filter has an exclusion volume of 0.1-0.3 m.
- the filtration is an ultrafiltration.
- a lipoid in a final concentration of 1-100% m / m, based on the extractive substances, is added in step (a) or before step (b).
- lipophilic organic impurities for example dioxins, aflatoxins, organochlorine pesticides or polychlorinated biphenyls
- lipophilic organic impurities for example dioxins, aflatoxins, organochlorine pesticides or polychlorinated biphenyls
- the lipoid is very particularly preferably selected from the group of vegetable oils, waxes and fatty acids.
- the heavy metal chelator is a polybasic organic acid or its salt.
- the polybasic organic acid is disodium hydrogen citrate.
- one or more pharmaceutically acceptable auxiliary (s) are added to the concentrated extract obtained in step (b) before drying.
- Pharmaceutically acceptable excipients include pharmaceutically acceptable carriers and pharmaceutically acceptable diluents.
- Preferred examples of such auxiliaries are maltodextrin and highly disperse silicon dioxide.
- Further examples of suitable carriers are known to the person skilled in the art and are monographed as pharmaceutical excipients in international pharmacopoeias.
- step (c) is carried out in the presence of one or more pharmaceutically acceptable auxiliary (s).
- the present invention relates to a method for producing a medicament, a food supplement or a medical product, wherein the steps of the method according to the invention are carried out and the dried extract obtained in step (c) is formulated with one or more pharmaceutically acceptable excipient (s) ,
- the drugs can be administered to an individual in a suitable dosage.
- Administration can be oral or parenteral, for example intravenous, intraperitoneal, subcutaneous, perinodal, intramuscular, topical, intradermal, intranasal, oral or intrabronchial, or via a catheter at one location in an artery.
- the dose is determined by the attending physician and essentially depends on the clinical factors. These factors are known in medicine and science and include, for example, height or weight, body surface area, age, gender, and the general state of health of the patient, the specific composition to be administered, the duration of treatment, the mode of administration and the possible simultaneous treatment with other medicines.
- a typical dose can be, for example, in a range between 0.001 and 5000 mg of extractive substances, doses below or above this exemplary range being conceivable, especially taking into account the factors mentioned above.
- the dose should be in a range between 100 mg and 1000 mg units per day.
- the composition is administered intravenously, which is not preferred to reduce the risk of anaphylactic To minimize reactions, the dose should be in the range between 1 ⁇ g and 10 mg units per kilogram of body weight per minute.
- the present invention further relates to a method for producing a medicament, a food supplement or a medical product, wherein the steps of the methods according to the invention are carried out and the drying in step (c) is carried out in the presence of one or more pharmaceutically acceptable auxiliary (s).
- the present invention relates to a method for producing a medicament, a food supplement or a medical product, wherein the steps of the method according to the invention are carried out and the pharmaceutically acceptable auxiliary (s) are added before the drying in step (c).
- the auxiliaries are maltodextrin and / or highly disperse silicon dioxide.
- the drying is carried out by means of atomization, belt or freeze drying.
- the Phyllanthus is Phyllanthus amarus.
- the Phyllanthus amarus is Phyllanthus amarus Schumach et Thonn.
- the present invention relates to a phyllanthus extract obtainable by the process according to the invention.
- the present invention also relates to a medicament obtainable by the process according to the invention.
- the present invention relates to a medicament containing a phyllant extract produced by the method according to the invention.
- the dosage form is a tablet, a dragee, a hard gelatin capsule or a soft gelatin capsule.
- the tablet is a film-coated tablet.
- Dried Phyllanthus amarus leaves were placed in an extraction system (steel vessel). 50% v / v EtOH was used as the extractant. Disodium hydrogen citrate was also added to the batch in a final concentration of 0.1-1.0% m / m. The EtOH content was checked by density measurement and corresponded to 35-45% m / m. The ratio of drug and solvent was 1:10 (+/- 3 solvents). The leaves were extracted for 1 hour at a temperature between 30 and 50 ° C. The Miscela was then washed through a filter with water (corresponds to three parts of drugs) and squeezed out. The mixture was then filtered through a membrane with an exclusion volume between 0.1-0.3 ⁇ m.
- Indian sterculia gum previously dissolved in ethanol water or absolute ethanol was added to the solution.
- the mixture was concentrated. This was done by evaporation under reduced pressure (about 300 mB descending to 20 mB) using a temperature of 30-60 ° C (+/- 5 ° C) until the material had a dry matter content of 20-40% (m / m) had.
- the soft extract was then mixed with maltodextrin until a homogeneous suspension was obtained. The mixture was then subjected to spray drying.
- Example 2 Extraction of Phyllanthus amarus leaves The process was carried out according to Example 1 with the following changes: After the addition of maltodextrin, the mixture was placed in a short-time heater at a temperature of 100 ° C. for a period of 36 seconds. This reduces the microbial load on the drug. The mixture was dried until the water content was below 5%. During the drying process, the outlet temperature of the heating unit did not exceed 90 ° C (+/- 5%). Silica was added during the drying process and after the drying process. The dried product was mixed and then sieved. The values of the pesticides examined here are mentioned in Table 1, the Ellagitannin values in Table 2.
- Example 1 The process was carried out according to Example 1 with the following changes: Before the filtration, a lipid (Miglyol) was added to the mixture (final concentration of 54.9% m / m, based on the extractive substances). The mixture was then filtered through a membrane with an exclusion volume between 0.1-0.3 ⁇ m. The above lipoid addition removes contaminations of lipophilic organic contaminants during ultrafiltration. The concentration, mixing and spray drying carried out subsequently are described in Example 1.
- a lipid Miglyol
- Table 1 shows a clear removal of the undesirable lipophilic impurities and / or residues below the detection limit.
- Table 2 shows that no ellagitannins are removed. nci not detectable
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- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicinal Preparation (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Extraction Or Liquid Replacement (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT01982401T ATE275413T1 (de) | 2000-10-06 | 2001-10-05 | Verfahren zur herstellung von phyllanthusextrakten |
CA002424930A CA2424930A1 (en) | 2000-10-06 | 2001-10-05 | Method for producing phyllanthus extracts |
DE50103561T DE50103561D1 (de) | 2000-10-06 | 2001-10-05 | Verfahren zur herstellung von phyllanthusextrakten |
JP2002533876A JP2004510822A (ja) | 2000-10-06 | 2001-10-05 | Phyllanthus抽出物の製造方法 |
DK01982401T DK1326624T3 (da) | 2001-10-05 | 2001-10-05 | Fremgangsmåde til fremstilling af phyllanthusekstrakter |
US10/398,380 US7074436B2 (en) | 2000-10-06 | 2001-10-05 | Method for the production of phyllanthus extracts |
EP01982401A EP1326624B1 (de) | 2000-10-06 | 2001-10-05 | Verfahren zur herstellung von phyllanthusextrakten |
AU2002213996A AU2002213996A1 (en) | 2000-10-06 | 2001-10-05 | Method for producing phyllanthus extracts |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00121852 | 2000-10-06 | ||
EP00121852.8 | 2000-10-06 | ||
EP00100825.7 | 2001-01-15 | ||
EP01100825 | 2001-01-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002030436A1 true WO2002030436A1 (de) | 2002-04-18 |
Family
ID=26071483
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2001/011526 WO2002030436A1 (de) | 2000-10-06 | 2001-10-05 | Verfahren zur herstellung von phyllanthusextrakten |
Country Status (10)
Country | Link |
---|---|
US (1) | US7074436B2 (de) |
EP (1) | EP1326624B1 (de) |
JP (1) | JP2004510822A (de) |
AT (1) | ATE275413T1 (de) |
AU (1) | AU2002213996A1 (de) |
CA (1) | CA2424930A1 (de) |
DE (1) | DE50103561D1 (de) |
ES (1) | ES2227298T3 (de) |
PT (1) | PT1326624E (de) |
WO (1) | WO2002030436A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1407679A1 (de) * | 2001-06-21 | 2004-04-14 | Kyowa Hakko Kogyo Co., Ltd. | Verfahren zur herstellung von pflanzenextrakthaltigem pflanzenpulver |
WO2005002609A1 (en) * | 2003-07-01 | 2005-01-13 | Max Zeller Söhne Ag | Plant extraction method and extract |
EP3954379A1 (de) | 2020-08-12 | 2022-02-16 | HFM - Hybrid Fusion Medicals, GmbH | Zusammensetzungen mit phyllanthus-extrakt zur verwendung in der behandlung oder vorbeugung einer sars-cov-2-infektion und/oder mindestens eines symptoms von covid-19 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2116253A1 (de) | 2008-05-07 | 2009-11-11 | Phytrix JV, LLC | Neuartiger Phyllanthus-Extrakt |
Family Cites Families (18)
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US28754A (en) * | 1860-06-19 | Congress boot | ||
US161477A (en) * | 1875-03-30 | Improvement in curtain-fixtures | ||
US3272796A (en) * | 1957-08-16 | 1966-09-13 | Oletta Sa | Salt of alkaloid from phyllanthus discodeus |
FR1206300A (fr) * | 1957-08-16 | 1960-02-09 | Réacteur nucléaire à combustible sous forme sphéroïde | |
DE3131471A1 (de) | 1981-03-20 | 1982-09-30 | Roderich Wilhelm Dr.-Ing. 6100 Darmstadt Gräff | Vorrichtung zum trocknen feuchter abluft aus einem oder mehreren schuettgut-trocknungsbehaeltern |
US4388457A (en) | 1982-02-11 | 1983-06-14 | University Patents, Inc. | Phyllanthostatin compounds |
US4673575A (en) | 1985-04-26 | 1987-06-16 | Fox Chase Cancer Center | Composition, pharmaceutical preparation and method for treating viral hepatitus |
US4937074A (en) | 1988-03-29 | 1990-06-26 | Fox Chase Cancer Center | Method of treating retrovirus infection |
CA2001898A1 (en) | 1988-10-31 | 1990-04-30 | Kuo-Hsiung Lee | Inhibition of human retroviruses |
US5854233A (en) | 1993-09-08 | 1998-12-29 | Pharmacy And Therapeutic Advisory Consultancy Ltd. | Method of treating liver disease and like indications with vasodilating agents |
US5529778A (en) | 1994-09-13 | 1996-06-25 | Rohatgi; Surendra | Ayurvedic composition for the prophylaxis and treatment of AIDS, flu, TB and other immuno-deficiencies and the process for preparing the same |
US5571441A (en) | 1994-11-01 | 1996-11-05 | The Procter & Gamble Company | Nutrient supplement compositions providing physiologic feedback |
US5648089A (en) | 1995-07-03 | 1997-07-15 | Shawkat; Tarek | Extract solution and herbal mixture for treatment of hepatitis |
US6136316A (en) | 1996-04-17 | 2000-10-24 | Dabur Research Foundation | Hepatoprotective compositions and composition for treatment of conditions related to hepatitis B and E infection |
WO2000056347A1 (en) * | 1999-03-24 | 2000-09-28 | Southern Petrochemical Industries Corporation Limited | An enriched fraction prepared from phyllanthus amarus for the treatment of hepatitis and the preparation thereof |
DE19919585A1 (de) | 1999-04-29 | 2000-12-07 | Cmi Ag | Verwendung von Phyllanthus zur Behandlung von oxidativem Streß und anderen Symptomen |
DE10030139A1 (de) | 2000-06-20 | 2002-01-10 | Cmi Ag | Verwendung von Phyllanthusbesandteilen zur Behandlung oder Prophylaxe von Infekten durch Flaviviridae |
JP2004513092A (ja) | 2000-10-06 | 2004-04-30 | シーエムアイ−センターズ・フォー・メディカル・イノヴェーション・アクチェンゲゼルシャフト | ヌクレオシド性阻害剤耐性レトロウイルス又は非ヌクレオシド性阻害剤耐性レトロウイルスに付随した疾患の予防及び/又は治療のためのPhyllanthus由来の化合物 |
-
2001
- 2001-10-05 US US10/398,380 patent/US7074436B2/en not_active Expired - Fee Related
- 2001-10-05 DE DE50103561T patent/DE50103561D1/de not_active Expired - Lifetime
- 2001-10-05 AU AU2002213996A patent/AU2002213996A1/en not_active Abandoned
- 2001-10-05 EP EP01982401A patent/EP1326624B1/de not_active Expired - Lifetime
- 2001-10-05 PT PT01982401T patent/PT1326624E/pt unknown
- 2001-10-05 WO PCT/EP2001/011526 patent/WO2002030436A1/de active IP Right Grant
- 2001-10-05 CA CA002424930A patent/CA2424930A1/en not_active Abandoned
- 2001-10-05 JP JP2002533876A patent/JP2004510822A/ja active Pending
- 2001-10-05 ES ES01982401T patent/ES2227298T3/es not_active Expired - Lifetime
- 2001-10-05 AT AT01982401T patent/ATE275413T1/de not_active IP Right Cessation
Non-Patent Citations (4)
Title |
---|
DATABASE BIOSIS [online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; 1991, MEHROTRA R ET AL: "IN-VITRO EFFECT OF PHYLLANTHUS-AMARUS ON HEPATITIS B VIRUS", XP002189217, Database accession no. PREV199191116067 * |
DATABASE BIOSIS [online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; 1993, MUNSHI ANUPAMA ET AL: "Evaluation of anti-hepadnavirus activity of Phyllanthus amarus and Phyllanthus maderaspatensis in duck hepatitis B virus carrier Pekin ducks.", XP002189216, Database accession no. PREV199497070792 * |
INDIAN JOURNAL OF MEDICAL RESEARCH SECTION A, vol. 93, no. MAR., 1991, pages 71 - 73, ISSN: 0970-955X * |
JOURNAL OF MEDICAL VIROLOGY, vol. 41, no. 4, 1993, pages 275 - 281, ISSN: 0146-6615 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1407679A1 (de) * | 2001-06-21 | 2004-04-14 | Kyowa Hakko Kogyo Co., Ltd. | Verfahren zur herstellung von pflanzenextrakthaltigem pflanzenpulver |
EP1407679A4 (de) * | 2001-06-21 | 2005-06-15 | Kyowa Hakko Kogyo Kk | Verfahren zur herstellung von pflanzenextrakthaltigem pflanzenpulver |
WO2005002609A1 (en) * | 2003-07-01 | 2005-01-13 | Max Zeller Söhne Ag | Plant extraction method and extract |
EP3954379A1 (de) | 2020-08-12 | 2022-02-16 | HFM - Hybrid Fusion Medicals, GmbH | Zusammensetzungen mit phyllanthus-extrakt zur verwendung in der behandlung oder vorbeugung einer sars-cov-2-infektion und/oder mindestens eines symptoms von covid-19 |
Also Published As
Publication number | Publication date |
---|---|
EP1326624B1 (de) | 2004-09-08 |
US20040033275A1 (en) | 2004-02-19 |
EP1326624A1 (de) | 2003-07-16 |
AU2002213996A1 (en) | 2002-04-22 |
DE50103561D1 (de) | 2004-10-14 |
ES2227298T3 (es) | 2005-04-01 |
US7074436B2 (en) | 2006-07-11 |
CA2424930A1 (en) | 2003-04-04 |
JP2004510822A (ja) | 2004-04-08 |
ATE275413T1 (de) | 2004-09-15 |
PT1326624E (pt) | 2005-01-31 |
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