EP1227780A2 - Dispersion aqueuse stable d'elements nutritifs - Google Patents

Dispersion aqueuse stable d'elements nutritifs

Info

Publication number
EP1227780A2
EP1227780A2 EP00992308A EP00992308A EP1227780A2 EP 1227780 A2 EP1227780 A2 EP 1227780A2 EP 00992308 A EP00992308 A EP 00992308A EP 00992308 A EP00992308 A EP 00992308A EP 1227780 A2 EP1227780 A2 EP 1227780A2
Authority
EP
European Patent Office
Prior art keywords
mixture
nutrient
group
foregoing
suspension
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.)
Withdrawn
Application number
EP00992308A
Other languages
German (de)
English (en)
Other versions
EP1227780A4 (fr
Inventor
Scott Peters
Darryl H. Woods
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ingredient Innovations International Co
Original Assignee
Ingredient Innovations International Co
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
Priority claimed from US09/685,366 external-priority patent/US6455072B1/en
Priority claimed from US09/698,403 external-priority patent/US6617305B1/en
Application filed by Ingredient Innovations International Co filed Critical Ingredient Innovations International Co
Publication of EP1227780A2 publication Critical patent/EP1227780A2/fr
Publication of EP1227780A4 publication Critical patent/EP1227780A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • 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
    • A61K31/01—Hydrocarbons
    • 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
    • A61K31/01—Hydrocarbons
    • A61K31/015—Hydrocarbons carbocyclic
    • 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
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A61K8/355—Quinones
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61K8/9706—Algae
    • A61K8/9717—Rhodophycota or Rhodophyta [red algae], e.g. Porphyra
    • 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
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • This invention relates to a stable aqueous dispersion of nutrients, and more particularly, to a dispersion comprising an ingredient selected from (a) an isoflavone, (b) lycopene, (c) lutein, (d) a Coenzyme Q or (e) a mixture of the foregoing ingredients; and a stabilizer.
  • a dispersion comprising an ingredient selected from (a) an isoflavone, (b) lycopene, (c) lutein, (d) a Coenzyme Q or (e) a mixture of the foregoing ingredients; and a stabilizer.
  • Nutritional ingredients such as an isoflavone, e.g. a soybean derived isoflavone, are currently available in tablets or other dry forms because heretofore they could not be satisfactorily dispersed in water.
  • the nutritional ingredients such as an isoflavone, lycopene, lutein, Coezyme Q's, are not ordinarily dispersable in aqueous systems because they are only slightly water or oil soluble.
  • aqueous dispersions or liposomes are desirable for use in beverages and cosmetics, in the form of aqueous dispersions or liposomes.
  • isoflavone is employed to treat humans to lower cholesterol, to treat solid tumors and angiogenic diseases. Additionally, it reduces bone calcium loss and is an antioxidant which can reduce free-radical damage to cells. Accordingly, a means for rendering these ingredients water dispersible is needed and desired.
  • a stable suspension comprising a nutrient or nutritional ingredient and a stabilizer therefore dispersed in an aqueous system, e.g. a solvent comprising water.
  • the ingredient is a nutrient selected from the group of (a) an isoflavone (b) lycopene, (c) lutein, (d) a Coenzyme Q n , where n is an integer of 1 to 12, (e) a mixture of any of the foregoing ingredients.
  • This invention involves a stable aqueous suspension which comprises a nutrient and a nutrient stabilizer dispersed in an aqueous system or solvent, e.g. water.
  • a suitable nutrient or nutritional ingredient is one which is suitable for therapeutic treatment of an animal, e.g. a human being, by ingestion, e.g. via a beverage, or a topical application, e.g. via a lotion or cream, but which is unfortunately typically insoluble or only slightly soluble in water at room temperature, e.g. 20°C to 25°C. It is these ingredients which are the subject of this invention.
  • Some suitable nutrients or nutritional ingredients include (1) a compound of the formula,
  • R is OH, ⁇ -glucoside, 6"-O-acetylglucoside, or 6"-O-malonylglucoside; R' is H
  • R" is H or OCH 3 ; such as isoflavone, e.g. a soybean derived isoflavone, and a substituted isoflavone, such as daidzein, genistein and glycitein; (2) lycopene, (3) lutein, (4) a Coenzyme Q n , where n is an integer of 1-12, e.g. Coenzyme Q 10 , and (5) a mixture of any of the foregoing ingredients.
  • isoflavone e.g. a soybean derived isoflavone
  • a substituted isoflavone such as daidzein, genistein and glycitein
  • lycopene (3) lutein
  • (4) a Coenzyme Q n where n is an integer of 1-12, e.g. Coenzyme Q 10 , and (5) a mixture of any of the foregoing ingredients.
  • the particular nutrient or mixture of nutritional ingredients is present in the inventive aqueous dispersions in an effective nutritional amount, that is an amount which causes its desired nutritional or therapeutic effect.
  • amount refers to quantity or concentration as appropriate to the context.
  • the amount of nutrient that constitutes a nutritional amount varies according to factors such as potency of the particular ingredient or mixture of ingredients, the route of administration and the mechanical system used to administer the dispersion.
  • a nutritionally effective amount of a particular nutrient can be selected by those of ordinary skill in the art with due consideration of such factors. Generally, a nutritionally effective amount will be from .005 parts by weight to about 10 parts by weight based on 100 parts by weight of the dispersion.
  • a suitable aqueous system or medium is selected.
  • a suitable aqueous system or medium for the dispersions of this invention include water and an aqueous solution of an organic alcohol of 1 to 6 carbon atoms, e.g. ethanol, propylene glycol, glycerin, etc., and a mixture of the foregoing; present in an amount of up to ten percent (10%) by weight.
  • the aqueous system is one which will permit a stable dispersion to be formed therein when combined with the selected nutrient or mixture of nutrients, which in turn is destined to be combined with a suitable nutrient stabilizer.
  • the aqueous system is present in an amount which affords the desired dispersion and is dependent upon the selected nutrient or mixture of nutritional ingredients with the selected nutrient stabilizer.
  • the aqueous system comprises 75 to 95 weight percent of the dispersion.
  • a suitable stabilizer includes (1) a lecithin, derived from soybean or egg which contain a complex mixture of phospholipids consisting mainly of phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, and phosphatidic acid combined with varying amounts of other substances such as triglycerides; the lecithin can be of standard grade or can be modified or refined lecithin e.g. deoiled, hydrogenated, hydroxylated, enzyme modified, acetylated, etc.; (2) a hydrocolloid, e.g.
  • xanthan gum a pectin, gelatin, guar gum, carrageenan
  • a surfactant e.g. cetylpyridinlium chloride, polysorbate 80, sorbitan monostearate, polyglycerolesters, block copolymers of propylene oxide and ethylene oxide
  • a Dowicil a product of The Dow Chemical Company, e.g. Dowicil 200 of the formula
  • An aqueous dispersion of the selected nutrient comprises the nutrient stabilizer in an amount effective to stabilize the aqueous dispersion relative to an identical aqueous formulation or mixture not containing the nutrient stabilizer, such that the active ingredient does not settle, cream or flocculate after agitation so quickly as to prevent reproducibility, e.g. reproducible dosing.
  • Reproducible application, e.g. dosing can be achieved if the resultant aqueous suspension is substantially uniform for about 1 to 2 hours after agitation thereof.
  • the particular amount of stabilizer that constitutes an effective amount is dependent upon the particular stabilizer, the particular aqueous system or medium employed and the particular nutritional ingredient or mixture of ingredients employed. It is therefore not practical to enumerate a specific effective amount for use with specific dispersions or formulations of the invention, but such amount can readily be determined by those skilled in the art with due consideration of the factors set forth above. Generally, however, the stabilizer can be present in a formulation in an amount from about 0.05 percent by weight to about 10 percent by weight, more preferably about .2 percent to about 5 percent by weight, based on the weight of the dispersion or formulation.
  • the nutrient stabilizer e.g. Dowicil 200 preservative
  • the aqueous system e.g. water
  • the active ingredient or nutritional agent e.g. isoflavone
  • the resultant mixture is then subjected to a high shear pressure treatment using any commercially available equipment for such purpose, e.g. a Microfluidizer, a product manufactured Microfluidics International
  • 6500-7000 psi preferably at a sheer pressure of 6500 to 8000 psi, and most preferably at a shear pressure of 7000 to 7500 psi, whereby a particle size to the active ingredient typically is less than 500nm, preferably less than 300 nm, most preferably less than 250 nm, to form the desired aqueous dispersion.
  • the procedure described above can be modified, namely the stabilizer is added to the resultant aqueous dispersion, i.e. subsequent to the described a high shear pressure treatment of the mixture of the nutrient combined with the aqueous system.
  • the resultant aqueous nutrient dispersion can then be further formulated and administered to a patient, e.g. a mammal such as a human being, by any conventional means, such as topically, orally; etc.
  • a patient e.g. a mammal such as a human being
  • the dispersion is combined with other drugs, adjuvants, etc. in the form of a cream or lotion, e.g. a cosmetic, or in the form of a liquid, e. g. a beverage.
  • SoyLife 100 a product manufactured by Schouten, USA Inc., 3300 Edinborough Way, Minneapolis, MN 55435, contains ten percent by weight of soy derived isoflavone. Ten weight percent of this material was mixed or dispersed with 0.2% by weight of Dowicil 200 and 89.8% by weight of water using a laboratory mixer. The resultant mixture was fluidized twice through a Microfluidizer, Model Ml 10A, at 7,400-psi sheer pressure and 40 psi head pressure. The resultant slurry or dispersion was homogeneous and could easily be incorporated into a skin cream formulation.
  • Prevastein HC a product of Central Soya Company Inc., 1946 West Cook Road, Fort Wayne, _IN 46801, contains 40% by weight of isoflavone. Ten weight percent of this nutrient was combined with 0.1 percent by weight of potassium sorbate and 0.1%) by weight of citric acid in 89.8%> by weight of water. The resultant mixture was mixed with a laboratory mixer, then fluidized twice through the Microfluidizer as in Example 1, at 7500-psi sheer. Rhodigel (xanthan gum), 0.5% by weight, was added to the fluidized sample during high-speed mixing with a laboratory mixer. The resultant product was a thick viscous liquid that did not separate.
  • Example 2 The resultant dispersion obtained in Example 2 was compared to samples prepared similarly to Example 2 but did not include a stabilizer and/or was not fluidized. When diluting the dispersion prepared in Example 2 with water (0.25-0.5% dispersion), the nutrient remained dispersed for over a week, with very little precipitation forming. The other samples prepared were diluted at similar levels as the Example 2 sample, but these dispersions precipitated much more quickly (within 1-2 hours).

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Birds (AREA)
  • Biotechnology (AREA)
  • Chemical & Material Sciences (AREA)
  • Mycology (AREA)
  • Botany (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention concerne une dispersion aqueuse stable d'éléments nutritifs, notamment une dispersion aqueuse d'un ingrédient nutritionnel actif choisi parmi (a) une isoflavone, (b) le lycopène (c) la lutéine, (d) une coenzyme Qn (où n désigne un entier compris entre 1 et 12), ou (e) un mélange de l'un quelconque des éléments nutritifs précédents.
EP00992308A 1999-10-28 2000-10-30 Dispersion aqueuse stable d'elements nutritifs Withdrawn EP1227780A4 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US685366 1984-12-24
US16199599P 1999-10-28 1999-10-28
US09/685,366 US6455072B1 (en) 1999-10-28 2000-10-10 Stable aqueous dispersion of nutrients
US09/698,403 US6617305B1 (en) 2000-10-10 2000-10-27 Stable aqueous dispersion of nutrients
PCT/US2000/041706 WO2001037781A2 (fr) 1999-10-28 2000-10-30 Dispersion aqueuse stable d'elements nutritifs
US161995P 2009-03-20

Publications (2)

Publication Number Publication Date
EP1227780A2 true EP1227780A2 (fr) 2002-08-07
EP1227780A4 EP1227780A4 (fr) 2006-09-06

Family

ID=27388711

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00992308A Withdrawn EP1227780A4 (fr) 1999-10-28 2000-10-30 Dispersion aqueuse stable d'elements nutritifs

Country Status (2)

Country Link
EP (1) EP1227780A4 (fr)
WO (1) WO2001037781A2 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MXPA02009956A (es) 2000-04-14 2003-02-12 Mars Inc Composiciones y metodos para mejorar la salud vascular.
FR2815861B1 (fr) * 2000-10-26 2003-02-28 Oreal Utilisation de l'association d'au moins un carotenoide et d'au moins un isoflavonoide pour traiter les signes cutanes du vieillissement
US6811801B2 (en) 2001-12-12 2004-11-02 Abbott Laboratories Methods and compositions for brightening the color of thermally processed nutritionals
US20030228392A1 (en) 2002-06-06 2003-12-11 Wyeth Infant formula compositions containing lutein and zeaxanthin
DE20319249U1 (de) * 2003-12-10 2004-12-30 Aquanova German Solubilisate Technologies (Agt) Gmbh Lutein-Konzentrat
US20090118227A1 (en) 2007-11-07 2009-05-07 Bristol-Myers Squibb Company Carotenoid-containing compositions and methods

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1112568A (en) * 1965-07-15 1968-05-08 Taisho Pharmaceutical Co Ltd Aqueous suspensions containing benzoquinone derivatives
US3499088A (en) * 1965-07-15 1970-03-03 Taisho Pharmaceutical Co Ltd Stable aqueous solutions of coenzyme q with a polyoxyethylene hydrogenated castor oil and propylene glycol and process for the manufacture thereof
WO1998026008A1 (fr) * 1996-12-12 1998-06-18 Basf Aktiengesellschaft Dispersions aqueuses stables et poudre seche stable dispersible dans l'eau de xanthophylles, leur preparation et leur utilisation

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4264466A (en) * 1980-02-14 1981-04-28 The Procter & Gamble Company Mulls containing chain structure clay suspension aids
US4742066A (en) * 1986-03-17 1988-05-03 Charles Of The Ritz Group Ltd. Skin treatment composition and method
DE19609476A1 (de) * 1996-03-11 1997-09-18 Basf Ag Stabile zur parenteralen Verabreichung geeignete Carotinoid-Emulsionen
US6096343A (en) * 1997-10-27 2000-08-01 Gerhard Gergely Instant calcium/soybean granules, their use and process for their preparation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1112568A (en) * 1965-07-15 1968-05-08 Taisho Pharmaceutical Co Ltd Aqueous suspensions containing benzoquinone derivatives
US3499088A (en) * 1965-07-15 1970-03-03 Taisho Pharmaceutical Co Ltd Stable aqueous solutions of coenzyme q with a polyoxyethylene hydrogenated castor oil and propylene glycol and process for the manufacture thereof
WO1998026008A1 (fr) * 1996-12-12 1998-06-18 Basf Aktiengesellschaft Dispersions aqueuses stables et poudre seche stable dispersible dans l'eau de xanthophylles, leur preparation et leur utilisation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO0137781A2 *

Also Published As

Publication number Publication date
WO2001037781A2 (fr) 2001-05-31
WO2001037781A3 (fr) 2001-12-13
WO2001037781A8 (fr) 2002-05-30
EP1227780A4 (fr) 2006-09-06

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