EP1353569A2 - Preparation destinee a ameliorer l'assimilation des aliments - Google Patents

Preparation destinee a ameliorer l'assimilation des aliments

Info

Publication number
EP1353569A2
EP1353569A2 EP02715439A EP02715439A EP1353569A2 EP 1353569 A2 EP1353569 A2 EP 1353569A2 EP 02715439 A EP02715439 A EP 02715439A EP 02715439 A EP02715439 A EP 02715439A EP 1353569 A2 EP1353569 A2 EP 1353569A2
Authority
EP
European Patent Office
Prior art keywords
preparation
acid
food
cis
trans
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Withdrawn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
EP02715439A
Other languages
German (de)
English (en)
Inventor
Klaus Krämer
Oliver Hasselwander
Uwe Oberfrank
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP1353569A2 publication Critical patent/EP1353569A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Definitions

  • the present invention relates to food, food or pharmaceutical preparations which contain conjugated trans / cis octa-decatrienoic acid and to processes for their preparation. Preparations according to the invention preferably contain calendulic acid.
  • the invention also relates to the use of the preparations for reducing food intake in humans and animals, and for better food utilization in humans and animals, for changing the body composition, methods for reducing food intake and a kit which contains the preparation according to the invention.
  • Fatty acids and triglycerides have a multitude of applications in the food industry, animal nutrition, cosmetics and pharmaceuticals. Depending on whether they are free saturated or unsaturated fatty acids or triglycerides with an increased content of saturated or unsaturated fatty acids, they are suitable for a wide variety of applications. For example, a high proportion of lipids with unsaturated fatty acids and especially with polyunsaturated fatty acids is important for the nutrition of animals and humans, since these e.g. a positive influence on the triglyceride level or cholesterol level in the blood and thus reduce the risk of heart disease. Unsaturated fatty acids are used in various diet foods or medications.
  • conjugated unsaturated fatty acids are particularly valuable and sought-after unsaturated fatty acids.
  • Conjugated polyunsaturated fatty acids are rather rare compared to other polyunsaturated fatty acids.
  • CLA is a collective term for positional and structural isomers of linoleic acid, which are characterized by a conjugated double bond system on the carbon atom 8, 9, 10 or 11. Geometric isomers exist for each of these positional isomers, i.e. cis-cis, trans-cis, cis-trans, trans-trans. Especially C18: 2 cis-9, trans-11 and C18: 2 trans-10, cis-12 CLAs, which are the most biologically active isomers, are of particular interest because they have been shown to be cancer-preventive in animal experiments, anti-arteriosclerotic act and reduce body fat in humans and animals. Commercially, CLAs are mainly sold as free fatty acids.
  • CLA CLA-containing fatty acids
  • ruminant animals such as cattle (Chin, Journal of Food Composition and Analysis, 5, 1992: 185-197) and sheep, and dairy products have very high CLA concentrations.
  • Cattle have 2.9 to 8.9 mg / g fat.
  • vegetable oils, margarines and fats from non-ruminant animals have CLA concentrations of only 0.6 to 0.9 mg / g fat.
  • Linoleic acid (18: 2); c9, c12)
  • conjugated linoleic acid reduces body fat in humans and animals or increases the feed turnover per body weight in animals (WO 94/16690, WO 96/06605, WO 97/46230, WO 97/46118).
  • conjugated linoleic acid By administering conjugated linoleic acid, allergies (WO 97/32008), diabetes (WO 99/29317) or cancer can also be positive (Banni, Carcinogenesis, Vol. 20, 1999: 1019-1024, Thompson, Cancer, Res., Vol 57, 1997: 5067-5072).
  • Polyunsaturated fatty acids are also added to baby food to "increase the nutritional value" and as essential building blocks that ensure growth and brain development.
  • CLA has very far-reaching positive nutritional effects.
  • CLA naturally only occurs in significant quantities in ruminants and their products, such as milk, cheese, etc.
  • the consumption of meat and milk products has decreased taken to reduce the amount of saturated fat considered unhealthy. At the same time, this also means a reduction in the intake of "healthy" CLA.
  • the object of the present invention is therefore to provide an alternative preparation which has nutritionally similar beneficial effects as a preparation which contains CLA.
  • the present invention therefore relates to a food, dietary supplement, animal feed or pharmaceutical preparation containing conjugated trans / cis octadecatrienoic acid.
  • the present invention is based on the surprising finding that the addition of conjugated trans / cis octadecatrienoic acid, in particular calendulic acid, to food leads to a reduced food intake without a reduction in body weight being observed. That feed conversion is significantly improved when conjugated octadecatrienoic acid is added to the diet.
  • octadecatrienoic acid or the term “calendulic acid” includes not only the free acid, but also the salts, and esters and other non-toxic derivatives.
  • the term encompasses non-toxic salts or glycerides, especially triglycerides, or ethyl or methyl esters as described below.
  • the present invention thus further relates to a method for producing a food, dietary supplement, animal feed or pharmaceutical preparation, which comprises adding a conjugated trans / cis octadecatrienoic acid to the preparation.
  • the said trans / cis octadecatrienoic acid preferably has a t10, cl2 configuration.
  • said trans / cis octadecatrienoic acid is therefore calendulic acid.
  • Calendulic acid is a C18: 3 fatty acid with a t8, tlO, cl2 configuration.
  • Calendulic acid is the fatty acid responsible for the observed reduction in food intake and improved food utilization in mice according to the invention when calendula oil is added to the feed, as the comparative experiments in the examples with corn oil show.
  • the chemical production of calendulic acid is described in US 3,356,699. Calendula acid comes naturally e.g.
  • conjugated trans / cis octadecatrienoic acids can be obtained by chemical modification of oils containing linolenic acid, e.g. from linseed oil, soybean or hemp oil.
  • Preparations according to the invention are outstandingly suitable as a food or feed additive, e.g. in diets or on animal fattening.
  • calendulic acid can be used to support a diet, e.g. to reduce body weight in humans, which also has an advantageous effect on eating habits.
  • the improved utilization of the increased food leads to a reduction in food consumption, which can be particularly advantageous in less developed regions with food shortages or in extreme situations (illnesses, competitive sports).
  • a change in body composition in particular a reduction in body fat content, can advantageously be achieved.
  • Preparations according to the invention can also be used economically and ecologically advantageously in animal nutrition, in particular for reducing the amount of feed or for reducing the fat content in animals.
  • animal nutrition in particular for reducing the amount of feed or for reducing the fat content in animals.
  • the conjugated trans / cis octadecatrienoic acid or the calendulic acid is contained in the preparation as calendula oil.
  • calendula oil is understood to mean a fatty acid mixture which contains calendula acid.
  • the proportion of calendulic acid in the calendula oil is preferably approximately 30%, more preferred is a proportion of 50%, even more preferred is a proportion of 60%, 70%, 80% or 90%. Most preferred is 95% or more.
  • the proportion of calendulic acid after saponification of the fatty acids and conversion of the fatty acids to methyl esters can be determined by gas chromatography.
  • calendula oil can contain various other saturated or unsaturated fatty acids e.g. Contain linoleic acid, palmitic acid.
  • the proportion of the various fatty acids in the calendula oil can fluctuate depending on the production process. Every fatty acid pattern is encompassed by the preparation according to the invention, in particular fatty acid patterns which arise in the production of oil from vegetable material and which contain the calendula oil component mentioned. It is preferred that the calendula oil contains little scatter of different fatty acids or that the number of different fatty acids in the calendula oil is small.
  • the preparation mentioned contains further additives.
  • additives is understood to mean further additives which are advantageous for nutrition or health, e.g. "Nutrients", “Dietary Additives” or "Active Ingredients”.
  • the preparation can contain one or more additives for animal or human nutrition or treatment and can be diluted or mixed therewith. Additives can be administered together with or separately from the feed, food, dietary supplement or pharmaceutical.
  • a food, dietary supplement, animal feed or pharmaceutical preparation contains no additives or no amounts of additives that can be considered harmful to animal or human nutrition.
  • “Nutrients” are understood to mean additives which are advantageous for the nutrition of humans or animals.
  • the preparation according to the invention therefore preferably also contains vitamins, for example vitamins A, B1, B2, B6, B12, C, D3, and / or E, folic acid, nicotinic acid, taurine, carboxylic acids, for example tricarboxylic acids, citrate, isocitrate, trans / cis aconitat, and / or homo-
  • the animal feed according to the invention particularly preferably contains inanimate, living and / or reproductive portions of fungi of the genus Mucor, yeasts of the genus Saccharomyces and / or bacteria of Enterobacteriaceae, such as E.
  • Bacteria of the genus Bacillus and here of the species Bacillus subtilis are very particularly preferred. Genetically modified and / or transgenic organisms and / or production strains suitable for producing the preparation according to the invention are also included according to the invention. The preceding list is not limiting for the present invention.
  • conjugated trans / cis octadecatrienoic acids are administered individually or in combination in feed
  • the active compounds are administered as pure substance or mixtures of substances or liquid or solid extracts together with conventional feed ingredients.
  • common feed ingredients are: maize, barley, wheat, oats, rye, tritale, sorghum, rice and bran, semolina and flours of these cereals, soybeans, soy products such as soybean meal, rapeseed, rapeseed meal, cottonseed and extraction meal, sunflower, sunflower extract, sunflower meal , Expeller of oilseeds, field beans, peas, gluten, gelatin, tapioca, yeast, single cell protein, fish meal, salts, minerals, trace elements, vitamins, amino acids, oils / fats and the like.
  • Advantageous compositions are e.g. in Jeroch, H. et al. Nutrition of farm animals, UTB described.
  • the preparation according to the invention can be provided as a powder, granulate, pellet, extrudate with a coating ("coated") and / or as combinations thereof.
  • the preparation of the animal feed according to the invention serves, for example, to improve the product properties, such as dust behavior, flow properties, water absorption capacity and storage stability.
  • Such preparations are widely known in the prior art. So be in animal nutrition s -d tr tr Di ⁇ TJ tr W Di 2 ⁇ ⁇ -3 W Di Mi Di ⁇ P P- ⁇ ⁇ P- P- ⁇ P- ⁇ P- ⁇ P P- 3: t
  • fine or amino acids e.g. preferably essential amino acids or such as e.g. Tyrosine, valine, leucine, threonine, tryptophan, methionine, arginine, histidine or glutamine.
  • the amount of conjugated trans / cis octadecatrienoic acid used e.g. Calendulic acid.
  • the amount of calendulic acid used can e.g. Represent 0.01% or 0.1% of the amount of fat added to the diet. Also preferred are 0.5%, 1%, 2% or 3%, 5% or 10% calendulic acid. This can also apply to other fatty acids.
  • the preparation according to the invention can be used to reduce food intake, change the body composition, and to improve food utilization in humans or animals.
  • the preparation according to the invention can be used to reduce the fat content in relation to the body protein content.
  • Feed consumption can preferably be reduced by 1% or 2%, even more preferred are 3%, even more preferred are 5%, 10% or more.
  • the proportion of fats added is replaced by the conjugated trans / cis octadecatrienoic acid.
  • the proportion of conjugated trans / cis octadecatrienoic acid in the added fat is at least 0.1 to 50% by weight, preferably 0.5 to 30% by weight, more preferably 1 to 20% by weight, based on an intake Energy that is 30% fat, that is approx. 70 to 90 g fat / day [according to: reference values for nutrient intake, 2000, German Society for Nutrition, Umschau Braus GmbH publishing company).
  • the present invention relates to a method for feeding the preparation according to the invention or for nutrition, with conjugated trans / cis octadecatrienoic acid, in particular calendulic acid, being added to the fat carrier of the diet.
  • Calendula oil can be obtained from the seeds of Calendula officinalis (marigold), for example. Table 2 shows that the fatty acid pattern of various calendula oils from calendula seeds in Varies depending on their method of manufacture. Such a variation is considered to be included in the preparation according to the invention.
  • Calendula oil can be obtained from plant seeds by pressing, for example, seeds with a high proportion of peel or peeled seeds. The compacts can also be pressed several times.
  • Vegetable seeds or other parts of plants can be used from any plant that contains calendulic acid. Whole plants can also be used. It is known that Calendula officialis contains a high proportion of calendula acid and is therefore particularly suitable for the production of calendula oil. Calendulic acid and thus also oil can also be produced synthetically (US 3,356,694).
  • Calendulic acid can also be produced by selective introduction of double bonds by Wittich reaction or metathesis.
  • calendulic acid can be prepared from oils containing octadecatrienoic acid. These octadecatrienoic acids can be conjugated to propylene glycol at 150 ° C.
  • Calendulic acid or its ester can be prepared by isomerization on the double bond of an octadecatrienoic acid in the presence of NaHS0 or KHS0. This reaction can be carried out as described in DE 114 16 90 for dehydrated castor oil (castor oil).
  • Calendulic acid can be produced analogously to the production process for CLA from oils containing octadecatrienoic acid: e.g. the isomerization of linoleic acid-containing oils with KOH in propylene glycol is carried out at 150 ° C in one process. Free CLA acids are obtained which contain only small amounts of undesired isomers (EP-839897).
  • linoleic acid alkyl esters can be isomerized with catalytic amounts (0.3 to 1%) of base (potassium alcoholate), CLA alkyl esters being obtained in high purity (DE-1156788 and DE-1156789).
  • Conjugated fatty acids and their esters can e.g. isomerized on the double bond in the presence of NaHS0 or KHS0, see also DE-1,141,690th
  • the conjugated cis / trans octadecatrienoic acid according to the invention produced in plants or microorganisms does not have to be worked up, e.g. by production in plants that are used directly for food or by microorganisms that are used in fermentation processes, such as e.g. in the production of cheese, yogurt, beer.
  • the present invention also relates to such plants.
  • transgenic crop plants such as Corn, rice, cereals, potatoes or transgenic oil-producing plants that produce calendulic acid, e.g. Linen, sunflowers, olives or plants whose natural calendula content has been increased through classic or transgenic breeding.
  • the present invention also relates to a kit which contains the preparation according to the invention.
  • the preparation can be packaged in one or more containers.
  • the components of the preparation according to the invention in particular calendula oil or calendulic acid, can be packed separately or together in a container of the kit.
  • the kit can be used to carry out the method according to the invention and can contain instructions for carrying it out.
  • Figure 1 describes the changes in body weight after calendulic acid treatment.
  • Figure 2 describes the food intake of female and male mice after treatment with calendulic acid.
  • Figure 3 describes the feed conversion of female and male mice after treatment with calendulic acid.
  • Figure 4 describes the body fat and protein composition of female mice after calendulic acid treatment. Examples
  • the calendula oil used contained approximately 62% calendulic acid (as a triglyceride).
  • the fatty acid composition of the calendula oil is shown in Table 2.
  • the animals were killed and viscera and organs such as the liver, heart and lungs were removed.
  • the empty bodies were frozen in liquid nitrogen, homogenized and the proportion of fat, protein and ash determined using standard methods.
  • the body weight gain of the two groups was comparable. However, there were clear differences in the body composition of the animals, especially in terms of body fat content.
  • Calendulic acid significantly reduced the fat content in the test animals. The effect was more pronounced in male animals than in female animals:

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Diabetes (AREA)
  • Nutrition Science (AREA)
  • Virology (AREA)
  • Hematology (AREA)
  • Mycology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Zoology (AREA)
  • Animal Husbandry (AREA)
  • Epidemiology (AREA)
  • Obesity (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
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  • Vascular Medicine (AREA)
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  • Urology & Nephrology (AREA)
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Abstract

Préparations alimentaires, diététiques ou médicamenteuses qui contiennent de l'acide octadécatriénoïque trans / cis, et procédés de production desdites préparations. Les préparations selon la présente invention contiennent de préférence de l'acide calendulique. La présente invention concerne en outre l'utilisation desdites préparations pour réduire la prise d'aliments chez les humains et les animaux et pour améliorer l'assimilation des aliments.
EP02715439A 2001-01-17 2002-01-16 Preparation destinee a ameliorer l'assimilation des aliments Withdrawn EP1353569A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10102050 2001-01-17
DE10102050A DE10102050A1 (de) 2001-01-17 2001-01-17 Zubereitung zur Verbesserung der Nahrungsverwertung
PCT/EP2002/000370 WO2002056708A2 (fr) 2001-01-17 2002-01-16 Preparation destinee a ameliorer l'assimilation des aliments

Publications (1)

Publication Number Publication Date
EP1353569A2 true EP1353569A2 (fr) 2003-10-22

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EP02715439A Withdrawn EP1353569A2 (fr) 2001-01-17 2002-01-16 Preparation destinee a ameliorer l'assimilation des aliments

Country Status (7)

Country Link
US (1) US7304089B2 (fr)
EP (1) EP1353569A2 (fr)
JP (2) JP2004520036A (fr)
AR (1) AR032248A1 (fr)
CA (1) CA2435077A1 (fr)
DE (1) DE10102050A1 (fr)
WO (1) WO2002056708A2 (fr)

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JP2009132721A (ja) 2009-06-18
DE10102050A1 (de) 2002-07-18
JP2004520036A (ja) 2004-07-08
WO2002056708A2 (fr) 2002-07-25
CA2435077A1 (fr) 2002-07-25
WO2002056708A3 (fr) 2002-11-07
AR032248A1 (es) 2003-10-29
US7304089B2 (en) 2007-12-04
US20040047894A1 (en) 2004-03-11

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