WO1999065504A1 - Extraction method, pharmaceutical composition and a cosmetic composition - Google Patents

Extraction method, pharmaceutical composition and a cosmetic composition Download PDF

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Publication number
WO1999065504A1
WO1999065504A1 PCT/NL1999/000379 NL9900379W WO9965504A1 WO 1999065504 A1 WO1999065504 A1 WO 1999065504A1 NL 9900379 W NL9900379 W NL 9900379W WO 9965504 A1 WO9965504 A1 WO 9965504A1
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WO
WIPO (PCT)
Prior art keywords
solvent
compound
vegetable material
water
tree
Prior art date
Application number
PCT/NL1999/000379
Other languages
French (fr)
Dutch (nl)
Inventor
Henri Marie Ruijten
Original Assignee
Xenobiosis
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Xenobiosis filed Critical Xenobiosis
Priority to AT99929944T priority Critical patent/ATE260668T1/en
Priority to AU46576/99A priority patent/AU4657699A/en
Priority to JP2000554383A priority patent/JP2002518337A/en
Priority to DE69915290T priority patent/DE69915290T2/en
Priority to US09/719,901 priority patent/US6759065B1/en
Priority to EP99929944A priority patent/EP1087780B1/en
Publication of WO1999065504A1 publication Critical patent/WO1999065504A1/en

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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
    • A61K36/11—Pteridophyta or Filicophyta (ferns)
    • 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
    • A61K36/16—Ginkgophyta, e.g. Ginkgoaceae (Ginkgo family)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9741—Pteridophyta [ferns]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9771—Ginkgophyta, e.g. Ginkgoaceae [Ginkgo family]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
    • A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation, decoction
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

Definitions

  • Extraction metho&6 pharmaceutical composition and a cosmetic composition
  • the disadvantage with the known methods is that to a lesser or greater degree the active compound (s) stay behind in the separated insoluble parts .
  • the object of the present invention is to provide a method as described in the preamble, by which the yield of active compound can be increased.
  • the method is characterized in that the vegetable material is frozen using a liquified gas and in frozen condition reduced in size, prior to being extracted with the solvent .
  • Liquid nitrogen is very suitable for this purpose because of its inert (non-oxidative) nature and low price.
  • European patent 0 431 535 describes a method of preparing an extract from Ginkgo biloba leaves that essen- tially corresponds with the method described above.
  • lead salt is used for further purification. For this reason this extraction method is also very laborious while moreover using a lead compound that is bad for both the environment and human health.
  • the vegetable material is chosen from a group comprising plant parts of the ginkgo tree (Ginkgo biloba) and Huperzia serrata.
  • Ginkgolides and flavonoids can be extracted from plant parts of the ginkgo tree.
  • Huberazine can be isolated from plant parts of the Huperzia serrata. All these compounds possess interesting pharmaceutical properties.
  • the most preferable plant parts of the ginkgo tree to be used are fresh leaves which have been dried shortly before treatment, with water being used as the solvent.
  • the term water is understood to mean a liquid comprised of mostly water that may contain up to 10% water-soluble alcohol or ketone, such as acetone.
  • the water can also comprise salt, which prevents undesirable compounds from dissolving and/or assists the precipitation of such compounds.
  • the water may also comprise enzymes that weaken the cell structure of the plant material.
  • the pH can vary within a wide range, it will generally be lower than 7.
  • the extracted leaves may be washed again with water to which a completely water-miscible organic solvent has been added, such as 40% aceton.
  • the preparation of an extract from ginkgo leaves is known in the art.
  • an enzyme such as cellulase to break down the cell walls after reduction.
  • extraction with water is then performed for a maximum of 3 hours.
  • TBE (TBE) may conveniently be used.
  • the invention relates in particular to a pharma- ceutical preparation
  • a pharma- ceutical preparation comprising an active component containing a compound obtained according to a method outlined by the invention, together with a pharmaceutically acceptable excipient or carrier.
  • Such a pharmaceutical preparations may be used, for example, to treat patients with Alzheimer's disease, patients with symptoms caused by prolonged contact with organic solvents, etc.
  • the pharmaceutical preparations according to the invention can be administered in any form, particularly oral or parenteral administration will be preferred.
  • the invention also relates to a cosmetic preparation containing an active component comprised of a com- pound obtained according to a method outlined by the invention, together with a cosmetically acceptable topical carrier.
  • Such a cosmetic preparation can help to keep skin young and supple .
  • the invention will now elucidated with the aid of the following exemplary embodiment .
  • the liquid, containing as active components ginkgolides and flavonoids, is separated from the solid parts by means of filtering over a large-mesh filter and then subjected to microfiltration over, for example, a 0.2 ⁇ m hydrophillic filter and subsequently freeze-dried
  • the residue is after evaporation dissolved in a 3:2 mixture of acetone and water (first acetone is added until the residue is dissolved, then gradually water is added under heating to 50°C and sonication) . Subsequently the acetone is evaporated and the aqueous solution is freeze-dried.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Botany (AREA)
  • Biotechnology (AREA)
  • Mycology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Medical Informatics (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Cosmetics (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention relates to a method of extracting a compound from vegetable material, wherein the vegetable material is reduced and treated with a solvent. According to the invention, the vegetable material is frozen using a liquid nitrogen and in frozen condition reduced in size. According to two important embodiments, the vegetable material comes from the ginkgo tree, in particular fresh leaves, and water is used as the solvent. The invention also relates to a pharmaceutical preparation and a cosmetic preparation comprising as active component a compound obtained by the method according to the invention.

Description

Extraction metho&6)pharmaceutical composition and a cosmetic composition
The present invention relates to a method of extracting a compound from vegetable material, wherein the vegetable material is reduced in size, subjected to an extraction treatment using a solvent, after which the undissolved parts are separated from the solvent comprising the compound.
This type of method is quite old. Examples are the infusion of tea and the preparation of tinctures. In both cases the undissolved parts are usually separated from the solvent comprising the compound. This may be accomplished by, for example, filtering or centrifugation.
The disadvantage with the known methods is that to a lesser or greater degree the active compound (s) stay behind in the separated insoluble parts . The object of the present invention is to provide a method as described in the preamble, by which the yield of active compound can be increased.
To this end the method is characterized in that the vegetable material is frozen using a liquified gas and in frozen condition reduced in size, prior to being extracted with the solvent .
In this manner the vegetable material is effectively opened up and a higher percentage of yield is assured. Liquid nitrogen is very suitable for this purpose because of its inert (non-oxidative) nature and low price.
European patent 0 477 968 describes a method of preparing an extract of Ginkgo biloba by treating the leaves with aqueous acetone, an aqueous alkanol with 1 to 3 C atoms, or anhydrous methanol at a temperature of 40- 100°C. After the removal of solid parts, this solution is treated with ammonium sulphate, methyl ethyl ketone, and the resulting extract is extracted with a higher alkanol. After several additional steps an extract is obtained comprising 20 to % by weight of flavoglycosides, 2.5 to 4.4% by weight of ginkgolides A, B, C and J, and 2.0 to 4.0% by weight of bilobalide. The described method of extraction is very laborious.
European patent 0 431 535 describes a method of preparing an extract from Ginkgo biloba leaves that essen- tially corresponds with the method described above. In addition, lead salt is used for further purification. For this reason this extraction method is also very laborious while moreover using a lead compound that is bad for both the environment and human health. According to an important embodiment, the vegetable material is chosen from a group comprising plant parts of the ginkgo tree (Ginkgo biloba) and Huperzia serrata.
Such vegetable material proves to extract excellently by the method outlined in the present invention at hand, yielding pharmaceutically high-grade solutions. Ginkgolides and flavonoids can be extracted from plant parts of the ginkgo tree. Huberazine can be isolated from plant parts of the Huperzia serrata. All these compounds possess interesting pharmaceutical properties. The most preferable plant parts of the ginkgo tree to be used are fresh leaves which have been dried shortly before treatment, with water being used as the solvent.
Surprisingly, this method has proven that with fewer processing steps a purer product can be obtained. In the present application the term water is understood to mean a liquid comprised of mostly water that may contain up to 10% water-soluble alcohol or ketone, such as acetone. The water can also comprise salt, which prevents undesirable compounds from dissolving and/or assists the precipitation of such compounds. The water may also comprise enzymes that weaken the cell structure of the plant material. Though the pH can vary within a wide range, it will generally be lower than 7. In order to increase the level of flavonoids, the extracted leaves may be washed again with water to which a completely water-miscible organic solvent has been added, such as 40% aceton. The preparation of an extract from ginkgo leaves is known in the art. With this preparation the ginkgo leaves are dried after which they are extracted using alcohol or ketone, which may contain some water. In order to obtain a product with a sufficiently high content of active compound, further laborious refinement steps are necessary, increasing the cost of the product. In order to obtain a high-grade product, the plant parts of the ginkgo tree should be obtained from a 1 to 15-year-old ginkgo tree, preferably from a 3 to 10- year-old tree and most preferably from a 5-year-old tree.
To obtain a preparation with a suitable ginkgolide/ flavonoid ratio (such as 1:4 or higher) , the pH of the water preferably lies between 4 and 7.
To further increase the yield, it is advantageous to add an enzyme such as cellulase to break down the cell walls after reduction. Preferably extraction with water is then performed for a maximum of 3 hours.
In order to ensure a high level of purity, the extraction treatment is suitably carried out at a temperature from 10 to 60°C, preferably 20 to 40°C. One favourable embodiment for obtaining a composition containing the compound and having a long shelf life involves drying the solution containing the compound, which may conveniently be achieved by spray-drying or freeze-drying. Suitably the solvent is eliminated from the solvent containing the compound, and the residue is extracted with a further solvent .
In this manner it is possible to obtain a purer preparation comprising the compound. For the extraction of ginkgo methylisobutylketone (MIK) or tert . -butylether
(TBE) may conveniently be used.
In accordance with the above the invention also related to two preparations.
The invention relates in particular to a pharma- ceutical preparation comprising an active component containing a compound obtained according to a method outlined by the invention, together with a pharmaceutically acceptable excipient or carrier. Such a pharmaceutical preparations may be used, for example, to treat patients with Alzheimer's disease, patients with symptoms caused by prolonged contact with organic solvents, etc. The pharmaceutical preparations according to the invention can be administered in any form, particularly oral or parenteral administration will be preferred.
The invention also relates to a cosmetic preparation containing an active component comprised of a com- pound obtained according to a method outlined by the invention, together with a cosmetically acceptable topical carrier.
Such a cosmetic preparation can help to keep skin young and supple . The invention will now elucidated with the aid of the following exemplary embodiment .
Example 1
Within 72 hours of being picked, 10 g of ginkgo leaves are contacted with liquid nitrogen (3 ml) . The ginkgo leaves are crushed using a porcelain mortar. Then 100 ml of water is added as well as 1:1000% w/v of Ultra- zym AFP-L and Cellubrix L. (Novo Noridsk Ferment Ltd., Switzerland) ; this is incubated for 2 hours at 50°C and a pH of 5.5 while being mixed and subsequently extracted at a pH of 4-5. The liquid, containing as active components ginkgolides and flavonoids, is separated from the solid parts by means of filtering over a large-mesh filter and then subjected to microfiltration over, for example, a 0.2 μm hydrophillic filter and subsequently freeze-dried
(extract A) .
Example II
The method described in Example I is repeated. In the same manner described above, the residue resulting from the extraction is extracted for 1 hour with 40% acetone solution and subsequently freeze-dried (extract B) .
Water is added to both freeze-dried extracts A and B (0.1 g extract per ml water) . The obtained solutions are extracted with (1:1 v/v) methylisobutylketone (MIK) or tert . -butylether (TBE) . These extractions are repeated twice and the fractions are combined for each solvent. The solvents are evaporated by means of a film evaporator.
As it is difficult to adequately eliminate MIK, the residue is after evaporation dissolved in a 3:2 mixture of acetone and water (first acetone is added until the residue is dissolved, then gradually water is added under heating to 50°C and sonication) . Subsequently the acetone is evaporated and the aqueous solution is freeze-dried.
The resulting residues are analyzed with the aid of HPLC. A 150 * 3 mm ODS-3 Inertsil 5 column (Chrompack) was used. Isocratic elution, with as mobile phase methanol/ water (for ginkgolides) or methanol/buffer 55/45 v/v (for flavonoids) was performed with 1 ml/min.
Buffer composition: 1.2 g/1 ammonium dihydrogen phosphate with phosphoric acid at pH=2.5.
Retention times for Bilobalide, Ginkgolide A and B: 4.9, 9.0 and 10.1 min. Detection by means of a refractive index detector.
Retention times for the flavonoids Quercetin, Kaempferol and Isorametine: 8.9, 15.5 and 16.9 min. Detection at 360 nm.
The data a summarized in Table I.
TABLE I
Figure imgf000007_0001
*) in mg. The percentage of dry matter is indicated in brackets. The above table shows that extraction with MIK and TBE improves the purity of the product. Extraction with MIK results in a higher yield, while extraction with TBE is useful if a higher yield of ginkgolides in relation to flavonoids is desired.

Claims

1. A method of extracting a compound from vegetable material, wherein the vegetable material is reduced in size, subjected to an extraction treatment using a solvent, after which the undissolved parts are separated from the solvent comprising the compound, characterized in that the vegetable material is frozen using a liquified gas and in frozen condition reduced in size, prior to being extracted with the solvent .
2. A method according to claim 1, characterized in that the vegetable material is chosen from a group comprising plant parts of the ginkgo tree and Huperzia serrata.
3. A method according to claim 2 , characterized in that the plant parts of the ginkgo tree are fresh leaves, and water is used as the solvent .
4. A method according to claim 2 or 3 , character- ized in that the plant parts of the ginkgo tree are obtained from a 1 to 15-year-old ginkgo tree, preferably from a 3 to 10-year-old tree and most preferably from a 5- year-old tree.
5. A method according to claim 3 or 4 , character- ized in that the pH of the water lies between 4 and 7.
6. A method according to one of the claims 2 to 5, characterized in that after reduction an enzyme is added to break down the cell walls.
7. A method according to one of the claims 3 to 6, characterized in that extraction with water is performed for a maximum of 3 hours.
8. A method according to one of the claims 3 to 7, characterized in that the extraction treatment is carried out at a temperature from 10 to 60┬░C, preferably 20 to 40┬░C.
9. A method according to one of the preceding claims, characterized in that the extract obtained is subjected to a microfiltration.
10. A method according to one of the preceding claims, characterized in that the solution comprising the compound is dried, conveniently by spray-drying or freeze- drying .
11. A method according to one of the preceding claims, characterized in that the solvent is eliminated from the solvent comprising the compound, and is subsequently extracted with a further solvent.
12. A pharmaceutical preparation comprising as active component a compound obtained by a method according to one of the preceding claims, as well as a pharmaceutically acceptable excipient or carrier.
13. A cosmetic preparation comprising as active component a compound obtained by a method according to one of the preceding claims, as well as a cosmetically acceptable topical carrier.
PCT/NL1999/000379 1998-06-18 1999-06-18 Extraction method, pharmaceutical composition and a cosmetic composition WO1999065504A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AT99929944T ATE260668T1 (en) 1998-06-18 1999-06-18 METHOD FOR EXTRACTING A COMPONENT OF PLANT MATERIAL
AU46576/99A AU4657699A (en) 1998-06-18 1999-06-18 Extraction method, pharmaceutical composition and a cosmetic composition
JP2000554383A JP2002518337A (en) 1998-06-18 1999-06-18 Extraction method, drug component and beauty component
DE69915290T DE69915290T2 (en) 1998-06-18 1999-06-18 PROCESS FOR EXTRACTION OF AN INGREDIENT OF PLANT MATERIAL
US09/719,901 US6759065B1 (en) 1998-06-18 1999-06-18 Extraction method, pharmaceutical composition and a cosmetic composition
EP99929944A EP1087780B1 (en) 1998-06-18 1999-06-18 Extraction method of a compound from vegetable material

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL1009437A NL1009437C2 (en) 1998-06-18 1998-06-18 Extraction process.
NL1009437 1998-06-18

Publications (1)

Publication Number Publication Date
WO1999065504A1 true WO1999065504A1 (en) 1999-12-23

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Country Status (12)

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US (1) US6759065B1 (en)
EP (1) EP1087780B1 (en)
JP (1) JP2002518337A (en)
KR (1) KR100703242B1 (en)
CN (1) CN1160088C (en)
AT (1) ATE260668T1 (en)
AU (1) AU4657699A (en)
DE (1) DE69915290T2 (en)
DK (1) DK1087780T3 (en)
ES (1) ES2217770T3 (en)
NL (1) NL1009437C2 (en)
WO (1) WO1999065504A1 (en)

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Publication number Priority date Publication date Assignee Title
WO2006026713A2 (en) * 2004-08-31 2006-03-09 Tracie Martyn International, Llc Topical benfotiamine and pyridoxamine compositions
US10864525B1 (en) * 2017-05-26 2020-12-15 Cryocann USA Corporation System and method for cryogenic separation of plant material
CN109954292A (en) * 2017-12-25 2019-07-02 山东坦途农业科技有限公司 The extraction process of medicinal material
CA3147046A1 (en) 2021-01-29 2022-07-29 Vitalis Extraction Technology Inc. Liquid carbon dioxide and cosolvent biomass extraction method and system

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SU440394A1 (en) * 1972-08-10 1974-08-25 Институт Ботаники Им.В.Л.Комарова Ан Азербайджанской Сср The method of obtaining dye from raw materials of plant origin
EP0431535A1 (en) * 1989-12-04 1991-06-12 Dr. Willmar Schwabe GmbH & Co. Extract from Ginkgo biloba leaves, its method of preparation and pharmaceuticals containing the extract
EP0477968A1 (en) * 1990-09-28 1992-04-01 Dr. Willmar Schwabe GmbH & Co. Extract from Ginkgo biloba leaves, in particular for intravenous injection or infusion, a method of preparation of the extract and ampoule preparations containing the extract
WO1996039812A2 (en) * 1995-06-07 1996-12-19 Phyton, Inc. Cryopreservation of diverse plant cells

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SU440394A1 (en) * 1972-08-10 1974-08-25 Институт Ботаники Им.В.Л.Комарова Ан Азербайджанской Сср The method of obtaining dye from raw materials of plant origin
EP0431535A1 (en) * 1989-12-04 1991-06-12 Dr. Willmar Schwabe GmbH & Co. Extract from Ginkgo biloba leaves, its method of preparation and pharmaceuticals containing the extract
EP0477968A1 (en) * 1990-09-28 1992-04-01 Dr. Willmar Schwabe GmbH & Co. Extract from Ginkgo biloba leaves, in particular for intravenous injection or infusion, a method of preparation of the extract and ampoule preparations containing the extract
WO1996039812A2 (en) * 1995-06-07 1996-12-19 Phyton, Inc. Cryopreservation of diverse plant cells

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DATABASE WPI Section Ch Week 7529, Derwent World Patents Index; Class D13, AN 75-49034W, XP002095997 *

Also Published As

Publication number Publication date
DE69915290T2 (en) 2005-03-24
DK1087780T3 (en) 2004-07-12
CN1160088C (en) 2004-08-04
NL1009437C2 (en) 1999-12-21
AU4657699A (en) 2000-01-05
EP1087780B1 (en) 2004-03-03
KR20010052992A (en) 2001-06-25
ATE260668T1 (en) 2004-03-15
EP1087780A1 (en) 2001-04-04
DE69915290D1 (en) 2004-04-08
JP2002518337A (en) 2002-06-25
CN1310624A (en) 2001-08-29
ES2217770T3 (en) 2004-11-01
US6759065B1 (en) 2004-07-06
KR100703242B1 (en) 2007-04-20

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