EP1102584A2 - Antioxidative, antiproliferative zusammensetzung mit carnitin und einem carotenoid - Google Patents

Antioxidative, antiproliferative zusammensetzung mit carnitin und einem carotenoid

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Publication number
EP1102584A2
EP1102584A2 EP99935044A EP99935044A EP1102584A2 EP 1102584 A2 EP1102584 A2 EP 1102584A2 EP 99935044 A EP99935044 A EP 99935044A EP 99935044 A EP99935044 A EP 99935044A EP 1102584 A2 EP1102584 A2 EP 1102584A2
Authority
EP
European Patent Office
Prior art keywords
carnitine
lycopene
composition
propionyl
acid
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Withdrawn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
EP99935044A
Other languages
English (en)
French (fr)
Inventor
Claudio Cavazza
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.)
Sigma Tau HealthScience SpA
Original Assignee
Sigma Tau HealthScience SpA
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 Sigma Tau HealthScience SpA filed Critical Sigma Tau HealthScience SpA
Publication of EP1102584A2 publication Critical patent/EP1102584A2/de
Withdrawn legal-status Critical Current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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • 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
    • A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
    • 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)
    • A61K36/81—Solanaceae (Potato family), e.g. tobacco, nightshade, tomato, belladonna, capsicum or jimsonweed
    • 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
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • A61P39/00—General protective or antinoxious agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/02—Antidotes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • 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
    • 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

  • Antioxidant, antiproliferous composition comprising a carnitine and a carotenoid.
  • the present invention relates to a composition for the prevention and/or treatment of diseases brought about by the presence of free radicals due to environmental pollution and by lipoperoxidation phenomena of atherosclerotic, vascular, cardiac or cerebral kind; of proliferative alterations of tissues comprising prostatic, uterine, mammary or colon tissues; sight and retina alterations comprising cataract and macular degeneration of the retina.
  • the composition may take the form and exert the action of a dietary supplement or of an actual medicine, depending upon the support or preventive action, or the strictly therapeutic action, which the composition is intended to exert in relation to the particular individuals it is to be used in.
  • composition that can be administered orally, parenterally, rectally, transdermally or by ocular instillation, which comprises in combination:
  • propionyl L-carnitine or a pharmacologically acceptable salt thereof possibly in combination with another "carnitine", where what is meant by "carnitine” is L-carnitine or an alkanoyl L-carnitine selected from the group comprising acetyl L-carnitine, valeryl L- carnitine and isovaleryl L-carnitine or their pharmacologically acceptable salts; and
  • a carotenoid preferably selected from the group comprising of lycopene, ⁇ -carotene, ⁇ -carotene, zeaxanthin, cryptoxanthin, lutein or mixtures thereof or extracts of natural vegetable products containing such carotenoids, typically tomato extracts ⁇ Lycopersicon esculentum).
  • the carotenoids are a group of long-chain vegetable pigments of a terpenic nature (tetraterpenes) containing up to 40 carbon atoms with a conjugated system of double bonds.
  • Carotenoids are present in superior plants, in chloroplasts and in those plastids located in the regions of the plant where chlorophyll is absent (some roots and many flowers and fruits, such as, for example, tomatoes, in which they increase during ripening); they are also to be found in blue algae, in some photosynthetic bacteria and in some fungi.
  • Carotenoids play a complementary role to chlorophyll in photosynthesis, absorbing some light rays and transmitting the energy to the chlorophyll itself.
  • carotenoids are present in the vegetable world, only forty of these are present in the human diet and only fourteen are absorbed in the gut, the remainder consisting of non- absorbable epoxides. The most common of these fourteen are lycopene, ⁇ -carotene, ⁇ -carotene, lutein, zeaxanthin and the ⁇ -cryptoxanthins.
  • Lycopene presents eleven linearly conjugated double bonds (whereas ⁇ - carotene presents nine) and is the carotenoid with the longest chain of linearly conjugated double bonds.
  • lycopene cannot transform itself in the body into ⁇ -carotene, which is characterised by a trimethylcyclohexanyl ring on the two sides of the carbon chain.
  • ⁇ -carotene is capable of transforming itself through reduction of the chain to trans-retinol and retinoic acid and of acting as provitamin A.
  • lycopene is the one which presents the greatest ability to block singlet oxygen, which is more than twice that of ⁇ -carotene, for instance. Lycopene is absorbed by the body, particularly in the presence of fat and is found in the blood and tissues in its two isomeric forms, cis- and trans-ly coipene.
  • lycopene Like all carotenoids, lycopene cannot be synthesised by the body, but must be ingested with food.
  • lycopene is its potent antioxidising action most notably against singlet oxygen, which is one of the most reactive oxygen products in producing free radicals.
  • lycopene is also extremely active in protecting cells and tissues from other reactive species of oxygen such as hydrogen peroxide and nitrous oxide.
  • lycopene is also superior to that of ⁇ - and ⁇ -carotene when measured on cell cultures (C3H/10T1/2 cells) where it prevents their neoplastic transformation.
  • the antilipoperoxidative activity of lycopene also explains its ability to prevent atherosclerosis and atherosclerotic vascular damage and also, in conjunction with its IGF-inhibiting and junctional intracellular communication enhancing activity, tumour cell proliferation.
  • Lycopene is the most potent of the carotenoids in inhibiting the spontaneous development of breast tumours in the rat and the growth of leukaemic cells (Hl-60 promyelocytic leukaemia cell line) as well as rat glioma C-6 cells in vitro or the neoplastic transformations induced by chemical agents.
  • leukaemic cells Hl-60 promyelocytic leukaemia cell line
  • rat glioma C-6 cells in vitro or the neoplastic transformations induced by chemical agents.
  • AMD age-related macular degeneration of the retina
  • L-carnitine and its alkanoyl derivatives are well known for the important role they are capable of playing at metabolic level, particularly with regard to oxidation and to fatty acid utilisation through ⁇ -oxidation.
  • L-carnitine in fact, whether taken with the diet or synthesised by the body, is concentrated by the blood in the organs which are metabolically most active in the utilisation of fatty acids, such as the skeletal muscles and heart.
  • L-carnitine deficiency may give rise to myopathies, whereas the oral administration of L-carnitine improves the clinical status of such myopathies.
  • L-carnitine performs an important function in energy production, with the result that adequate levels of L-carnitine are necessary for normal energy metabolism at cardiac and muscular level.
  • L-carnitine and its derivatives are its ability to stabilise the cell membranes and to protect them against lesions induced by oxidative processes.
  • composition containing as its characterising components a combination of: (a) propionyl L-carnitine or a pharmacologically acceptable salt thereof, and
  • a carotenoid chosen from the group consisting of lycopene, ⁇ - carotene, ⁇ -carotene, zeaxanthin, cryptoxanthin, lutein or mixtures thereof, is extremely effective in the prevention and/or treatment of damage induced by the presence of free radicals due to environmental pollution and by lipoperoxidation phenomena of an atherosclerotic, vascular, cardiac or cerebral nature; of proliferative abnormalities of tissues including prostate, uterine, mammary and colon tissue; and of visual and retinal disorders including cataracts and macular degeneration of the retina, as a result of the potent synergistic effect exerted by its components.
  • component (a) may advantageously further comprise a "carnitine” selected from the group comprising L-carnitine, acetyl L-carnitine, valeryl L-carnitine and isovaleryl L-carnitine or their pharmacologically acceptable salts or mixtures thereof and that component (b) may consist in an extract of vegetable products containing it, such as, for example, tomato (Lycopersicon esculentum, Solanaceae family) extract.
  • a "carnitine” selected from the group comprising L-carnitine, acetyl L-carnitine, valeryl L-carnitine and isovaleryl L-carnitine or their pharmacologically acceptable salts or mixtures thereof
  • component (b) may consist in an extract of vegetable products containing it, such as, for example, tomato (Lycopersicon esculentum, Solanaceae family) extract.
  • the (a):(b) weight-to-weight ratio ranges from 1:0.1 to 1:10.
  • carnitine and its derivatives and lycopene and the other carotenoids such as lutein, zeaxanthin and cryptoxanthin, as well as ⁇ - carotene, present low toxicity and are well tolerated, particularly when administered orally.
  • compositions according to the invention described herein To assess the antioxidising and protective activity against free radicals exerted by the compositions according to the invention described herein, their effects on intoxication induced by carbon tetrachloride were assayed on an isolated liver cell culture.
  • liver cells taken from rat liver were isolated using the method described by Seglen (Seglen F.O., Meth. Cell. Biol. Chem.. 264. 4747, 1989).
  • AlAT alanine aminotransferase
  • aspaAT aspartate aminotransferase
  • Cytological examination of the liver cells confirms the reduction in necrotic cells after treatment with propionyl L-carnitine and lycopene; however, at ultrastructural examination particularly, whereas the cells in the control group (CC1 ) presented haemochrome abnormalities, irregular nuclear membranes, disappearance of the mitochondrial crests in the mitochondria and reduction in the number of ribosomes, those cells which had been exposed not only to CC1 , but also to carnitines and lycopene, presented unexpectedly intact cell membranes and nuclei, and regular heterochromatins, as well as regular mitochondria and number of ribosomes.
  • lens opacification is obtained in the rat which, in terms of its severity, is classified in increasing order as stage I, II and III according to the method described by Sippel (Sippel T.O., Invest. Qphthalmol., 5, 568, 1966).
  • Propionyl L-carnitine 400 mg/kg + natural tomato carotenoid extract (100 mg/kg) 14 6 0
  • the animals were then sacrificed and the liver was taken from each of them and used for assaying total cholesterol and triglycerides according to the Dehoff and Levy methods, respectively [Dehoff J.L., Clin. Chem., 24, 433, 1978; Levy A., Advances in Automated Analysis (Technicon Corp.) 497, Thurman, Miami 1972].
  • the aorta and heart were also isolated and used to evaluate the presence of atherosclerotic lesions according to the Klurfeld method (Klurfeld D.M., J. Med., 10. 35, 1979) rating lesions from I to IV according to severity.
  • VLDL (mg/dl) LDL (mg/dl) HDL (mg/dl)
  • HC hypercholesterolaemic controls
  • CM carnitine mixture
  • TE natural tomato carotenoid extract
  • P propionyl L-carnitine
  • L lycopene Antiproliferative activity tests with evaluation of ornithine decarboxylase activity
  • teleocidin administered subcutaneously in the rat causes proliferative abnormalities in the skin of the animals thus treated which can even lead to the formation of tumour-type keratotic processes.
  • the proliferative abnormality is accompanied by an increase in ornithine decarboxylase enzyme and, as in all cases of pathological proliferative activation in general, the increase in ornithine decarboxylase activity is proportional to the severity of the lesion induced.
  • teleocidin dissolved in 0.2 cc of aqueous solution was injected subcutaneously into the depilated backs of mice at a dose of 5 ⁇ g/mouse.
  • test animals received oral administrations of either carnitine mixture alone (400 mg/kg) consisting in a combination of L-carnitine, acetyl L-carnitine, propionyl L-carnitine and isovaleryl L-carnitine in identical weight amounts to one another, or propionyl L-carnitine alone (400 mg/kg), or natural tomato carotenoid extract (100 mg/kg containing 5% lycopene) alone, or lycopene alone (5 mg/kg), or combinations of carnitine mixture with lycopene or lycopene-containing extracts, or of propionyl L-carnitine with lycopene or lycopene- containing extracts.
  • carnitine mixture alone 400 mg/kg
  • acetyl L-carnitine acetyl L-carnitine
  • propionyl L-carnitine and isovaleryl L-carnitine in identical weight amounts to one another
  • propionyl L-carnitine alone 400
  • these products were applied to the skin of the mice half an hour prior to injection of teleocidin after suitable dispersion of the products first in dimethylsulphoxide and then in lanolin until a 200 mg/cc concentration of the carnitine mixture, or a 200 mg/cc concentration of the carotenoid extract containing 5% lycopene, or a 5 mg/cc concentration of lycopene were achieved.
  • the various preparations were applied at the dose of 0.3 cc on the skin area where teleocidin was injected and the area injected was protected with an occlusive bandage.
  • the procedure adopted five hours after injection consisted in the method described by O'Brien and Nakadate (O'Brien T.G., Cancer Res., 35, 1662, 1975; Nakadate T., Cancer Res., 42, 2841, 1982).
  • the protein concentration of the epidermal extract was measured using the Lowry method (Lowry O.H., J: Biol. Chem., 193, 265, 1951).
  • compositions according to the invention are reported hereinbelow.
  • Carnitine mixture mg 500 (L-carnitine mg 125, acetyl L-carnitine mgl25, propionyl L-carnitine mg 125, isovaleryl L-carnitine mg 125)
  • Carnitine mixture mg 300 (L-carnitine mg 75, acetyl L-carnitine mg 75, propionyl L-carnitine mg 75, isovaleryl L-carnitine mg 75)
  • Carnitine mixture mg 300 (L-carnitine mg 75, acetyl L-carnitine mg 75, propionyl L-carnitine mg 75, isovaleryl L-carnitine mg 75)
  • Carnitine mixture mg 300 (L-carnitine mg 75, acetyl L-carnitine mg 75, propionyl L-carnitine mg 75, isovaleryl L-carnitine m 75)
  • Extract of cactus blossom (Opuntia ficus indica) mg 50
  • pharmacologically acceptable salt of L-carnitine or alkanoyl L-carnitine is any salt of these active ingredients with an acid that does not give rise to unwanted toxic or side effects. These acids are well known to pharmacy experts.
  • Non-limiting examples of suitable salts are the following: chloride; bromide; iodide; aspartate, acid aspartate; citrate, acid citrate; tartrate; phosphate, acid phosphate; fumarate; acid fumarate; glycerophosphate; glucose phosphate; lactate; maleate, acid maleate; orotate; oxalate, acid oxalate; sulphate, acid sulphate, trichloroacetate, trifluoro acetate and methanesulphonate.
  • the compositon according to the invention may also comprise vitamins, coenzymes, minerals substances and antioxidants.

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  • Health & Medical Sciences (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
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  • Natural Medicines & Medicinal Plants (AREA)
  • Toxicology (AREA)
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  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
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  • Ophthalmology & Optometry (AREA)
  • Dermatology (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP99935044A 1998-08-03 1999-07-29 Antioxidative, antiproliferative zusammensetzung mit carnitin und einem carotenoid Withdrawn EP1102584A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IT1998RM000516A IT1302125B1 (it) 1998-08-03 1998-08-03 Composizione ad attivita' antiossidante ed antiproliferativacomprendente una carnitina ed un carotenoide
ITRM980516 1998-08-03
PCT/IT1999/000251 WO2000007581A2 (en) 1998-08-03 1999-07-29 Antioxidant, antiproliferous composition, comprising a carnitine and a carotenoid

Publications (1)

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EP1102584A2 true EP1102584A2 (de) 2001-05-30

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EP99935044A Withdrawn EP1102584A2 (de) 1998-08-03 1999-07-29 Antioxidative, antiproliferative zusammensetzung mit carnitin und einem carotenoid

Country Status (21)

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EP (1) EP1102584A2 (de)
JP (1) JP2002522382A (de)
KR (1) KR20010072146A (de)
CN (1) CN1311674A (de)
AR (1) AR021172A1 (de)
AU (1) AU5064199A (de)
BR (1) BR9912703A (de)
CA (1) CA2338035A1 (de)
EE (1) EE200100052A (de)
HK (1) HK1039062A1 (de)
HU (1) HUP0102807A2 (de)
IL (1) IL140797A0 (de)
IS (1) IS5816A (de)
IT (1) IT1302125B1 (de)
MA (1) MA26666A1 (de)
NO (1) NO20010532L (de)
PL (1) PL346161A1 (de)
SK (1) SK1252001A3 (de)
TN (1) TNSN99152A1 (de)
TR (1) TR200100333T2 (de)
WO (1) WO2000007581A2 (de)

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PT1711070E (pt) * 2004-01-28 2016-02-15 Nestec Sa Composição nutricional para melhorar o estado da pele e prevenir doenças de pele
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CA2338035A1 (en) 2000-02-17
WO2000007581A2 (en) 2000-02-17
IT1302125B1 (it) 2000-07-31
SK1252001A3 (en) 2001-08-06
WO2000007581A3 (en) 2000-05-11
IS5816A (is) 2001-01-16
ITRM980516A0 (it) 1998-08-03
JP2002522382A (ja) 2002-07-23
BR9912703A (pt) 2001-05-02
EE200100052A (et) 2002-06-17
HK1039062A1 (zh) 2002-04-12
IL140797A0 (en) 2002-02-10
ITRM980516A1 (it) 2000-02-03
CN1311674A (zh) 2001-09-05
KR20010072146A (ko) 2001-07-31
PL346161A1 (en) 2002-01-28
NO20010532L (no) 2001-03-20
MA26666A1 (fr) 2004-12-20
TNSN99152A1 (fr) 2005-11-10
HUP0102807A2 (hu) 2002-03-28
TR200100333T2 (tr) 2001-07-23
NO20010532D0 (no) 2001-01-31
AU5064199A (en) 2000-02-28

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