EP1147167A1 - Procede d'obtention d'une huile enrichie en acides gras hydroxyoctadecadienoiques (hode) ou de ses esters, a partir d'un melange huileux contenant de l'acide linoleique, ou ses esters - Google Patents

Procede d'obtention d'une huile enrichie en acides gras hydroxyoctadecadienoiques (hode) ou de ses esters, a partir d'un melange huileux contenant de l'acide linoleique, ou ses esters

Info

Publication number
EP1147167A1
EP1147167A1 EP00901675A EP00901675A EP1147167A1 EP 1147167 A1 EP1147167 A1 EP 1147167A1 EP 00901675 A EP00901675 A EP 00901675A EP 00901675 A EP00901675 A EP 00901675A EP 1147167 A1 EP1147167 A1 EP 1147167A1
Authority
EP
European Patent Office
Prior art keywords
hode
esters
acid
oil
oxidation
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Withdrawn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
EP00901675A
Other languages
German (de)
English (en)
French (fr)
Inventor
Max Rombi
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.)
Laboratoires Arkopharma SA
Original Assignee
Laboratoires Arkopharma SA
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 Laboratoires Arkopharma SA filed Critical Laboratoires Arkopharma SA
Publication of EP1147167A1 publication Critical patent/EP1147167A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/006—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by oxidation
    • 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
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • A61P3/06—Antihyperlipidemics
    • 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
    • A61Q19/06—Preparations for care of the skin for countering cellulitis

Definitions

  • the present invention relates to a process for the preparation of hydroxyoctadecadienoic acids, more particularly 9-hydroxy-10, 12-octadecadienoic acid and 13-hydroxy-9, 11-octadecadienoic acid, and their mixture, as well as their isomers such as 9 (R / S) -hydroxy-10E, 12Z-octadecadienoic acid, optionally in the form of their esters, more particularly in the form of their ethyl ester.
  • hydroxyoctadecadienoic acid is called HODE.
  • the invention relates to a process for preparing HODE by controlled oxidation of linoleic acid and / or linolenic acid, then reduction.
  • the invention further relates to a process for the preparation of HODE from triglycerides rich in linoleic acid and / or linolenic acid or from linoleic acid and / or linolenic acid in the form of free fatty acid or in the form of an ester or a salt, for example in the form of an ethyl ester.
  • the invention further relates to a medicament, in particular for the treatment of obesity, containing as active ingredient HODE and pharmacologically acceptable carriers.
  • the invention also relates to a food supplement containing HODE, in particular for the treatment of obesity.
  • the invention further relates to a cosmetic product containing HODE and cosmetologically acceptable supports, more particularly for the localized treatment of overweight and its consequences on the appearance of the skin, such as orange peel, dimples, horse breeches.
  • a cosmetic product containing HODE and cosmetologically acceptable supports more particularly for the localized treatment of overweight and its consequences on the appearance of the skin, such as orange peel, dimples, horse breeches.
  • lipids cannot be reduced to less than 30% of energy intake since they not only play an important role in the texture and taste perception of food, but also that a minimum amount is necessary in food, especially for the biosynthesis of essential fatty acids and hormones, and the renewal of membrane phospholipids.
  • One of the objectives of the invention was to find a molecule allowing the regulation of the lipolytic activity of the adipocyte, that is to say, capable of hydrolyzing the triglycerides stored in adipocytes into free fatty acids and glycerols .
  • adrenaline and caffeine are two molecules known for their lipolytic effects. These molecules in particular increase the levels of adenosine cyclic mono phosphate (cAMP), the first step in activating lipolysis.
  • cAMP adenosine cyclic mono phosphate
  • Another object of the invention is to provide a lipolytic molecule synthesized from products commonly found in nature, in a simple and effective manner.
  • HODE hydroxyoctadecadienoic fatty acid
  • the invention therefore relates to a process for obtaining an oil enriched with hydroxyoctadecadienoic fatty acid (HODE) and in particular 9-hydroxyoctadecadienenoic acid (9-HODE), or its esters or its salts, from a oily mixture containing linoleic acid and / or linolenic acid, or their esters or their salts, characterized in that a controlled oxidation of linoleic acid and / or linolenic acid is carried out, or of their esters, in the presence of an oxidation catalyst, the oxidation being stopped when the total content of HODE, or of its esters, is greater than at least 5% and / or the content of 9-hydroxy- acid isomer 10, 12-octadecad ⁇ eno ⁇ que (9- HODE), or its esters, is greater than at least 1.5% and in that the hydroperoxides formed during "- of the oxidation reaction are reduced by a reducing agent.
  • the starting oily mixture is a vegetable oil containing more than 40% by weight of linoleic acid and / or linolenic acid in the form of triglycerides, such as oil of corn, borage, safflower, soybeans, evening primrose, sunflower, blackcurrant seeds, wheat germ, hemp, pumpkin seeds, flaxseed.
  • the starting oily mixture is an oily mixture containing more than 40% by weight of linoleic acid and / or linolenic acid, preferably containing 75% of ethyl linoleate.
  • the final content in the oil enriched in total HODE or in 9-HODE is at least 5%, respectively 1.5% by weight.
  • the final content in the oil enriched in total HODE or in 9-HODE is respectively between 10 and 12% by weight and between 2.2 and 2.5% by weight.
  • the oxidation catalyst is a halogen of iron, copper, preferably FeCl 3 .
  • the reducing agent is preferably NaBH 4 .
  • the invention further relates to the oil enriched in hydroxyoctadecadienoic fatty acid (HODE) or its esters or its salts, obtained as described above.
  • HODE hydroxyoctadecadienoic fatty acid
  • the invention relates to a medicament for the treatment of obesity containing as active principle the fatty acid 9-hydroxyoctadecad ⁇ eno ⁇ que (9-HODE) or its esters or its salts, acceptable pharmacologically, preferably in the form of enriched oil obtained as described above.
  • the invention further relates to a food supplement for the treatment of obesity containing as active principle the fatty acid 9-hydroxyoctadecad ⁇ eno ⁇ que (9-HODE) or its esters or its pharmacologically acceptable salts, preferably in the form of enriched oil obtained as described above.
  • a food supplement for the treatment of obesity containing as active principle the fatty acid 9-hydroxyoctadecad ⁇ eno ⁇ que (9-HODE) or its esters or its pharmacologically acceptable salts, preferably in the form of enriched oil obtained as described above.
  • the invention further relates to a cosmetic product for the treatment of obesity containing as active principle the fatty acid 9-hydroxyoctadecad ⁇ eno ⁇ que (9-HODE) or its esters or its cosmetically acceptable salts, preferably in the form of enriched oil obtained as described above.
  • hydroxyoctadecadienoic acid HODE
  • fatty acids are present in many vegetable oils.
  • the following vegetable oils contain more than 40% linoleic acid in the form of triglycerides: borage oil, safflower, soybeans, evening primrose, sunflower, blackcurrant seeds, wheat germ, hemp, pumpkin seeds, flax.
  • the HODE can be obtained from triglycerides rich in linoleic and / or linolenic acid. This process is advantageous insofar as it makes it possible to use a natural vegetable oil, therefore perfectly suitable for use by the oral route, but has the drawback of considerably limiting the final content of the 9-HODE isomer.
  • the structure of the starting product is a linoleic acid triglyceride or a linoleic acid ester of the following general formula (I):
  • Linolenic acid exists in two forms: ⁇ -linolenic acid (or acid (Z, Z, Z) 9, 12, 15-octadecatrienoic) and ⁇ -linolenic acid (or acid (Z, Z, Z) 6, 9, 12- octadecat ⁇ enoic).
  • the oxidation reaction is carried out in the presence of an oxygenation catalyst such as an iron or copper halide, preferably FeCl 3 .
  • the reaction has a variable duration from 12 to 78 hours and at a temperature between -20 ° C and 40 ° C, at atmospheric pressure and / or under reduced pressure.
  • the degree of oxidation is followed by different criteria:
  • the mixture is reduced, namely, the hydroperoxides formed during the oxidation are reduced.
  • An ethanolic solution of NaBH 4 or an ethanolic solution of any other reducing agent is used which is added in parts to the reaction mixture.
  • the temperature of the mixture is maintained between 4 and 25 ° C.
  • the reduction is complete when the temperature becomes constant.
  • the reaction medium is neutralized to pH6-7 by adding an acid solution, preferably a solution of an acid which is pharmacologically and / or cosmetologically acceptable, for example citric acid.
  • the compounds (II) and (III) are extracted with hexane or any other organic solvent capable of dissolving them.
  • the organic phase is washed with water until neutral.
  • the organic phase is then dried over sodium sulfate or anhydrous magnesium sulfate. Then the filtrate is evaporated under vacuum.
  • the product obtained is a light yellow oily liquid with a slightly aromatic odor. It has a total content of compounds (II) and (III) (determined by gas chromatography) greater than 5% by weight and a content of compound (II) [acid 9 (R / S) hydroxy-lOE, 12Z- octadecad ⁇ eno ⁇ que or ester of 9 (R / S) hydroxy-10E, 12Z-octadecad ⁇ eno ⁇ que acid] greater than 1.5% by weight.
  • the starting product is an oily mixture containing 75% by weight of ethyl moleate.
  • Oxygen is bubbled (technical quality) in the reaction medium using a stainless steel or bronze filter, with a porosity of 2 to 4 ⁇ m (of the HPLC filter type or particle filter for gases ). This fine bubbling is maintained at a flow rate of 1 liter / m for 48 to 72 hours.
  • the oxidation rate is controlled either:
  • the reduction phase is completed when the temperature is constant when the stirring is maintained at room temperature (approximately 1 hour).
  • the reduction reaction releases hydrogen.
  • the object of the invention is to find a molecule having an activity on lipolysis, that is to say, capable of promoting the hydrolysis of the triglycerides stored in the edipocytes, the free fatty acids thus released being then metabolized.
  • the purpose of this study is to study the effect of 9-HODE on the production of cAMP (cyclic adenos e monophosphate) which is a activator of lipolysis, in human adipocytes.
  • cAMP cyclic adenos e monophosphate
  • the concentration of cAMP is 10 times greater than that obtained with caffeine (7,940 fentomoles of cAMP / million adipocytes against 799).
  • 9-HODE is, in vitro, a potent activator of lipolysis thanks to a stimulation of the adipocyte production of cAMP greater than that of the caffeine and adrenaline molecules.
  • the study is carried out on twelve rats which are first subjected to a food restriction (simulation of a diet) for two weeks, then who receive a normal diet (weight gain) associated or not with the administration of a sunflower oil treated according to the process of the present invention and containing 2% by weight of 9-HODE.
  • a control group is used which receives sunflower oil devoid of 9-HODE. After eleven days of treatment, the fat mass is measured in the two groups.
  • a skin penetration study is carried out in vitro on human skin with FRANZ cells. These cells comprise a surface of human skin of 1.76 cm 2 on which 800 ⁇ g of 9-HODE are deposited. After 6 hours of contact, a 9-HODE assay is carried out by gas chromatography on the surface of the sample of human skin, in the epidermis, in the dermis and in the receptor phase.
  • 9-HODE therefore has significant skin penetrating power allowing it to act directly at the level of adipocytes.
  • Clinical study evaluating the effectiveness of a cosmetic gel containing 0.5% of 9-HODE A clinical study is carried out in twenty women with excess fatty tissue in the thighs ("horse breeches"). The volunteers applied for a month, twice a day, a gel containing 0.5% of 9-HODE on each thigh. The efficiency criterion is the measurement of the thigh circumference on two levels.
  • thermogenesis The difference in energy expenditure after treatment is statistically significant (p ⁇ 0.01). This increase in thermogenesis of almost 8% is particularly interesting for the treatment of obesity. 4863
  • 9-HODE can be administered as an acid or as a triglyceride.
  • 9-HODE is preferably administered in the form of free acid.
  • 9-HODE can be administered as a dietary supplement in the form of capsules, tablets, oral solution, lozenges, chews, etc. and / or in food. You can use 9-HODE pure or diluted in creams, gels, sticks, ointments, etc.
  • 9-HODE can be administered as a systemic or topical medication for the treatment of obesity.
  • the administration doses are, for example, orally, 50 to 5,000 mg / day and locally, 0.1 to 100%.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dermatology (AREA)
  • Wood Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Child & Adolescent Psychology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Edible Oils And Fats (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
EP00901675A 1999-01-29 2000-01-28 Procede d'obtention d'une huile enrichie en acides gras hydroxyoctadecadienoiques (hode) ou de ses esters, a partir d'un melange huileux contenant de l'acide linoleique, ou ses esters Withdrawn EP1147167A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9901078 1999-01-29
FR9901078A FR2789085B1 (fr) 1999-01-29 1999-01-29 Procede d'obtention d'une huile enrichie en acides gras hydroxyoctadecadienoiques (hode), ou de ses esters a partir d'un melange huileux contenant de l'acide linoleique, ou ses esters
PCT/FR2000/000208 WO2000044863A1 (fr) 1999-01-29 2000-01-28 Procede d'obtention d'une huile enrichie en acides gras hydroxyoctadecadienoiques (hode) ou de ses esters, a partir d'un melange huileux contenant de l'acide linoleique, ou ses esters

Publications (1)

Publication Number Publication Date
EP1147167A1 true EP1147167A1 (fr) 2001-10-24

Family

ID=9541426

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00901675A Withdrawn EP1147167A1 (fr) 1999-01-29 2000-01-28 Procede d'obtention d'une huile enrichie en acides gras hydroxyoctadecadienoiques (hode) ou de ses esters, a partir d'un melange huileux contenant de l'acide linoleique, ou ses esters

Country Status (17)

Country Link
US (1) US6348609B1 (zh)
EP (1) EP1147167A1 (zh)
JP (1) JP2002535479A (zh)
KR (1) KR20010102995A (zh)
CN (1) CN1342193A (zh)
AU (1) AU2299900A (zh)
BR (1) BR0007861A (zh)
CA (1) CA2325887A1 (zh)
FR (1) FR2789085B1 (zh)
HK (1) HK1043605A1 (zh)
IL (1) IL144573A0 (zh)
MX (1) MXPA01007680A (zh)
NZ (1) NZ513136A (zh)
PL (1) PL364225A1 (zh)
RU (1) RU2245358C2 (zh)
WO (1) WO2000044863A1 (zh)
ZA (1) ZA200106098B (zh)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2844454B1 (fr) * 2002-09-12 2006-05-19 Marc Schwaller Composition comprenant en association au moins une huile de courge et au moins une huile de bourrache,son utilisation comme medicament, comme agent dermatologique ou dermato-cosmetique
WO2004068970A2 (en) * 2003-01-31 2004-08-19 The Procter & Gamble Company Means for improving the appearance of mammalian keratinous tissue
WO2005059566A1 (ja) * 2003-12-16 2005-06-30 National Institute Of Advanced Industrial Science And Technology 酸化ストレスマーカー及びその測定法
WO2006137435A1 (ja) * 2005-06-22 2006-12-28 National University Corporation Gunma University Gタンパク質共役型受容体g2aの作動薬、及びg2a活性調節薬のスクリーニング方法
CN100548962C (zh) * 2007-11-27 2009-10-14 江南大学 一种醇-水体系中还原制备羟基共轭亚油酸的方法
CN101613267B (zh) * 2008-06-27 2012-08-29 中山市尤利卡天然药物有限公司 双羟基油酸及它的制备方法与用途
GB0814105D0 (en) * 2008-08-01 2008-09-10 Springdale Sustainable Develop Composition for accelerated production of collagen
US11304960B2 (en) * 2009-01-08 2022-04-19 Chandrashekar Giliyar Steroidal compositions
SI2588101T1 (sl) 2010-07-02 2015-01-30 Helix Biomedix, Inc. Derivati N-acil amino kisline za zdravljenje koĹľnih stanj, kot je celulitis
US20130274333A1 (en) * 2012-04-11 2013-10-17 Versitech Limited Coriolus versicolor extracts, methods of isolating biologically-active compounds, and uses thereof
CN110054560A (zh) * 2019-05-23 2019-07-26 河南农业大学 一种医药用木本α-亚麻酸的提纯方法及其应用
CN111568889A (zh) * 2020-06-12 2020-08-25 四川大学华西医院 羟基十八碳二烯酸在制备α-葡萄糖苷酶抑制剂类药物的用途及其分离方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU546872B2 (en) * 1982-06-16 1985-09-26 Unilever Plc Skin treatment compositions containing a fatty acid or ester
JPH0710774B2 (ja) * 1986-01-13 1995-02-08 株式会社ツムラ アンジオテンシンｉ転換酵素阻害剤
EP0437694B1 (de) * 1990-01-16 1993-06-16 Boots Pharma GmbH Verwendung einer Hydroxyoctadecadiensäure, deren zur Ketoform oxidierte Säure sowie deren Derivate zur Therapie östrogenabhängiger Krankheiten, sowie pharmazeutische Zusammensetzungen, die diese enthalten

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0044863A1 *

Also Published As

Publication number Publication date
FR2789085A1 (fr) 2000-08-04
NZ513136A (en) 2003-08-29
JP2002535479A (ja) 2002-10-22
US6348609B1 (en) 2002-02-19
RU2245358C2 (ru) 2005-01-27
MXPA01007680A (es) 2003-06-24
IL144573A0 (en) 2002-05-23
BR0007861A (pt) 2001-10-23
FR2789085B1 (fr) 2003-06-20
AU2299900A (en) 2000-08-18
PL364225A1 (en) 2004-12-13
WO2000044863A1 (fr) 2000-08-03
ZA200106098B (en) 2002-05-03
HK1043605A1 (zh) 2002-09-20
CA2325887A1 (fr) 2000-08-03
CN1342193A (zh) 2002-03-27
KR20010102995A (ko) 2001-11-17

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