ES2183587T3 - Procedimiento continuo para la preparacion de derivados de acido (s) -3-4-dihidroxibutirico opticamente puros.. - Google Patents
Procedimiento continuo para la preparacion de derivados de acido (s) -3-4-dihidroxibutirico opticamente puros..Info
- Publication number
- ES2183587T3 ES2183587T3 ES99935131T ES99935131T ES2183587T3 ES 2183587 T3 ES2183587 T3 ES 2183587T3 ES 99935131 T ES99935131 T ES 99935131T ES 99935131 T ES99935131 T ES 99935131T ES 2183587 T3 ES2183587 T3 ES 2183587T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- alpha
- expressed
- amylase
- optically pure
- 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.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 102000004139 alpha-Amylases Human genes 0.000 abstract 3
- 108090000637 alpha-Amylases Proteins 0.000 abstract 3
- 229940024171 alpha-amylase Drugs 0.000 abstract 3
- DZAIOXUZHHTJKN-VKHMYHEASA-N 3S,4-dihydroxy-butyric acid Chemical class OC[C@@H](O)CC(O)=O DZAIOXUZHHTJKN-VKHMYHEASA-N 0.000 abstract 2
- 229920000945 Amylopectin Polymers 0.000 abstract 2
- 238000006911 enzymatic reaction Methods 0.000 abstract 2
- 229920001542 oligosaccharide Polymers 0.000 abstract 2
- 150000002482 oligosaccharides Chemical class 0.000 abstract 2
- -1 (S) -3,4-dihydroxybutyl Chemical group 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 229910052784 alkaline earth metal Chemical group 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003957 anion exchange resin Substances 0.000 abstract 1
- 230000015556 catabolic process Effects 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 229940088598 enzyme Drugs 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004676 glycans Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229920001282 polysaccharide Polymers 0.000 abstract 1
- 239000005017 polysaccharide Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/22—Preparation of compounds containing saccharide radicals produced by the action of a beta-amylase, e.g. maltose
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04M—TELEPHONIC COMMUNICATION
- H04M1/00—Substation equipment, e.g. for use by subscribers
- H04M1/02—Constructional features of telephone sets
- H04M1/04—Supports for telephone transmitters or receivers
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04M—TELEPHONIC COMMUNICATION
- H04M1/00—Substation equipment, e.g. for use by subscribers
- H04M1/60—Substation equipment, e.g. for use by subscribers including speech amplifiers
- H04M1/6033—Substation equipment, e.g. for use by subscribers including speech amplifiers for providing handsfree use or a loudspeaker mode in telephone sets
- H04M1/6041—Portable telephones adapted for handsfree use
- H04M1/6058—Portable telephones adapted for handsfree use involving the use of a headset accessory device connected to the portable telephone
- H04M1/6066—Portable telephones adapted for handsfree use involving the use of a headset accessory device connected to the portable telephone including a wireless connection
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04M—TELEPHONIC COMMUNICATION
- H04M19/00—Current supply arrangements for telephone systems
- H04M19/02—Current supply arrangements for telephone systems providing ringing current or supervisory tones, e.g. dialling tone or busy tone
- H04M19/04—Current supply arrangements for telephone systems providing ringing current or supervisory tones, e.g. dialling tone or busy tone the ringing-current being generated at the substations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Signal Processing (AREA)
- Computer Networks & Wireless Communication (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Un procedimiento para producir derivados de ácido (S)-3,4-dihidroxibutírico ópticamente puros expresado por la **fórmula** a partir de fuente polisacárida, que comprende las etapas siguientes: (a) reacción enzimática, utilizando enzimas específicas para la degradación secuencial, de amilopectina a oligosa cárido con enlace alfa-(1,4) expresado por la fórmula 2; en donde dicha reacción enzimática utiliza alfa-amilasa y pululanasa de forma secuencial de modo que la amilo- pectina se degrade mediante alfa-amilasa y se inactive la alfa-amilasa restante antes de la introducción de pululanasa (b) oxidación del oligosacárido, mediante actuación de la resina de intercambio de aniones básica con un oxidante para dar el ácido (S)-3,4-dihidroxibutí rico expresado por la fórmula 3; y (c) esterificación subsiguiente con alcohol en presencia de un catalizador de ácido para dar éster de ácido (S)-3,4-dihidroxibutírico expresado por la fórmula 1 en donde, M representa hidrógeno, átomo de metal alcalinoo de metal alcalinotérreo; R representa grupo de alquilo lineal o ramificado con 1-5 carbonos.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR19980029912 | 1998-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2183587T3 true ES2183587T3 (es) | 2003-03-16 |
Family
ID=19545119
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99935128T Expired - Lifetime ES2183585T3 (es) | 1998-07-24 | 1999-07-23 | Procedimiento para la preparacion de derivados de (s) -3-4-dihidroxibutirico opticamente puros. |
| ES99935130T Expired - Lifetime ES2183586T3 (es) | 1998-07-24 | 1999-07-23 | Procedimiento continuo para la preparacion de (s) -3- hidroxi- gamma- butirolactona opticamente pura. |
| ES99935131T Expired - Lifetime ES2183587T3 (es) | 1998-07-24 | 1999-07-23 | Procedimiento continuo para la preparacion de derivados de acido (s) -3-4-dihidroxibutirico opticamente puros.. |
| ES99935127T Expired - Lifetime ES2183584T3 (es) | 1998-07-24 | 1999-07-23 | Procedimiento para la preparacion de (s) -3-hidroxi-gamma-butirolactona opticamente pura. |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99935128T Expired - Lifetime ES2183585T3 (es) | 1998-07-24 | 1999-07-23 | Procedimiento para la preparacion de derivados de (s) -3-4-dihidroxibutirico opticamente puros. |
| ES99935130T Expired - Lifetime ES2183586T3 (es) | 1998-07-24 | 1999-07-23 | Procedimiento continuo para la preparacion de (s) -3- hidroxi- gamma- butirolactona opticamente pura. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99935127T Expired - Lifetime ES2183584T3 (es) | 1998-07-24 | 1999-07-23 | Procedimiento para la preparacion de (s) -3-hidroxi-gamma-butirolactona opticamente pura. |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US6124122A (es) |
| EP (5) | EP1100954B1 (es) |
| JP (5) | JP2002521031A (es) |
| KR (5) | KR20000011940A (es) |
| CN (5) | CN1144878C (es) |
| AU (5) | AU5067999A (es) |
| CA (5) | CA2338755A1 (es) |
| DE (4) | DE69903441T2 (es) |
| ES (4) | ES2183585T3 (es) |
| WO (5) | WO2000005402A1 (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6713290B2 (en) * | 1998-07-24 | 2004-03-30 | Samsung Fine Chemicals Co., Ltd. | Process for preparing optically pure (S)-3-hydroxy-γ-butyrolactone |
| KR20000011940A (ko) * | 1998-07-24 | 2000-02-25 | 박영구 | α-(1,4)결합으로연결된올리고당의제조방법 |
| US6239311B1 (en) * | 2000-04-24 | 2001-05-29 | Board Of Trustees Operating Michigan State University | Process for the preparation of 3,4-dihydroxybutanoic acid and salts and lactones derived therefrom |
| KR100645665B1 (ko) * | 2000-07-27 | 2006-11-13 | 에스케이 주식회사 | (ｓ)-베타-하이드록시-감마-부티로락톤의 연속 제조방법 |
| FR2819123B1 (fr) * | 2000-12-29 | 2003-04-11 | St Microelectronics Sa | Pompe de charge a faible bruit pour boucle a verrouillage de phase |
| JP4824874B2 (ja) * | 2001-07-19 | 2011-11-30 | 高砂香料工業株式会社 | 光学活性γ−ブチロラクトンの製造方法 |
| AU2002329102A1 (en) * | 2002-09-18 | 2004-04-08 | Sk Corporation | CONTINUOUS PROCESS FOR THE PRODUCTION OF OPTICALLY PURE (S)-Beta HYDROXY-Gamma-BUTYROLACTONE |
| US6713639B1 (en) | 2002-10-28 | 2004-03-30 | Council Of Scientific And Industrial Research | Process for preparing enantiomerically pure (S)-3-hydroxy-gamma-butyrolactone |
| JP4545487B2 (ja) * | 2004-05-28 | 2010-09-15 | イハラケミカル工業株式会社 | アニリド化合物の製造方法 |
| KR100590857B1 (ko) | 2005-02-05 | 2006-06-19 | 엔자이텍 주식회사 | 양이온교환수지를 이용한 3-히드록시-감마-부티로락톤의 제조 방법 |
| WO2007100227A1 (en) * | 2006-03-02 | 2007-09-07 | Lg Chem, Ltd. | Method for preparing (s)-3-hydroxy-gamma-butyrolactone using hydrolase |
| JP2008162902A (ja) * | 2006-12-27 | 2008-07-17 | Central Glass Co Ltd | ジフルオロ酢酸エステルの製造方法 |
| CN102325563A (zh) | 2008-12-22 | 2012-01-18 | 昆士兰大学 | 贴剂制备 |
| CN105669423B (zh) * | 2016-01-08 | 2018-06-29 | 江西科技师范大学 | 4-(4-(苯甲氧基)苯基)-2-羟基丁酸的两种对映异构体的新合成方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3791865A (en) * | 1969-05-12 | 1974-02-12 | Staley Mfg Co A E | High maltose syrups |
| US3986890A (en) | 1972-02-21 | 1976-10-19 | Akademie Der Wissenschaften Der Ddr | Method of producing starch hydrolysis products for use as food additives |
| US3922200A (en) | 1974-03-18 | 1975-11-25 | Cpc International Inc | Enzymatic hydrolysis of granular starch |
| US4138484A (en) | 1976-08-16 | 1979-02-06 | Nelson Research & Development Company | Method for treating schizophrenia and method and composition for potentiating neuroleptic drugs |
| AT362526B (de) * | 1977-09-13 | 1981-05-25 | Boehringer Mannheim Gmbh | Verfahren und reagens zur bestimmung von alpha- -amylase |
| US4447532A (en) | 1982-04-29 | 1984-05-08 | H. J. Heinz Company | Process for the manufacture of low D.E. maltodextrins |
| US4612284A (en) | 1984-09-28 | 1986-09-16 | A. E. Staley Manufacturing Company | Process for the enzymatic hydrolysis of non-gelatinized granular starch material directly to glucose |
| US4963479A (en) * | 1986-10-07 | 1990-10-16 | Hoechst Celanese Corporation | Reagent system for an alpha-amylase assay containing aromatic substituted glycoside |
| JPS6413069A (en) * | 1987-07-03 | 1989-01-17 | Shiseido Co Ltd | Optically active mono-beta-lactam ring derivative and production thereof |
| JPH01202294A (ja) * | 1988-02-09 | 1989-08-15 | Agency Of Ind Science & Technol | グルコースの増収法 |
| US4912272A (en) | 1988-06-23 | 1990-03-27 | Mobil Oil Corporation | Lubricant blends having high viscosity indices |
| WO1990000500A2 (en) * | 1988-07-07 | 1990-01-25 | John Earp | Packaged food recovery apparatus |
| JP2825604B2 (ja) | 1990-04-11 | 1998-11-18 | 三井化学株式会社 | メチレン架橋されたポリアリールアミンの製造方法 |
| JPH04121197A (ja) * | 1990-09-11 | 1992-04-22 | Shin Etsu Chem Co Ltd | マルトオリゴ糖の製造方法 |
| JP2710688B2 (ja) * | 1990-10-09 | 1998-02-10 | 鐘淵化学工業株式会社 | ４―ブロモ―３―ヒドロキシ酪酸エステル誘導体の製造法 |
| JP3030073B2 (ja) | 1990-10-11 | 2000-04-10 | コベルコ健機株式会社 | ホイールクレーン |
| JP3072433B2 (ja) * | 1990-10-19 | 2000-07-31 | 東和化成工業株式会社 | 高純度マルトースの製造方法 |
| CA2049536C (en) * | 1991-05-13 | 1999-07-06 | Rawle I. Hollingsworth | Process for the preparation of 3,4-dihydroxybutanoic acid and salts thereof |
| GB9121289D0 (en) | 1991-10-08 | 1991-11-20 | Isf Spa | Composition and use |
| IS2334B (is) | 1992-09-08 | 2008-02-15 | Vertex Pharmaceuticals Inc., (A Massachusetts Corporation) | Aspartyl próteasi hemjari af nýjum flokki súlfonamíða |
| JP3351563B2 (ja) | 1992-12-03 | 2002-11-25 | 鐘淵化学工業株式会社 | ３−ヒドロキシ酪酸誘導体の製造法 |
| US5506353A (en) | 1994-03-21 | 1996-04-09 | Firmenich Sa | Particulate hydrogenated starch hydrolysate based flavoring materials and use of same |
| JP3855033B2 (ja) * | 1995-09-08 | 2006-12-06 | 高砂香料工業株式会社 | 光学活性３−ヒドロキシ−γ−ブチロラクトンの製造方法 |
| WO1998004543A1 (en) * | 1996-07-29 | 1998-02-05 | Warner-Lambert Company | Improved process for the synthesis of protected esters of (s)-3,4-dihydroxybutyric acid |
| KR100255039B1 (ko) * | 1997-07-28 | 2000-05-01 | 박영구 | L-카르니틴의제조방법 |
| US5808107A (en) | 1997-10-31 | 1998-09-15 | Board Of Trustees Operating Michigan State University | Process for the preparation of hydroxy substituted gamma butyrolactones |
| KR20000011940A (ko) * | 1998-07-24 | 2000-02-25 | 박영구 | α-(1,4)결합으로연결된올리고당의제조방법 |
-
1999
- 1999-07-23 KR KR1019990030064A patent/KR20000011940A/ko not_active Ceased
- 1999-07-23 EP EP99935131A patent/EP1100954B1/en not_active Expired - Lifetime
- 1999-07-23 CN CNB998103659A patent/CN1144878C/zh not_active Expired - Fee Related
- 1999-07-23 WO PCT/KR1999/000399 patent/WO2000005402A1/en not_active Ceased
- 1999-07-23 AU AU50679/99A patent/AU5067999A/en not_active Abandoned
- 1999-07-23 JP JP2000561344A patent/JP2002521031A/ja active Pending
- 1999-07-23 CA CA002338755A patent/CA2338755A1/en not_active Abandoned
- 1999-07-23 ES ES99935128T patent/ES2183585T3/es not_active Expired - Lifetime
- 1999-07-23 WO PCT/KR1999/000397 patent/WO2000005398A1/en not_active Ceased
- 1999-07-23 EP EP99935130A patent/EP1100953B1/en not_active Expired - Lifetime
- 1999-07-23 EP EP99935127A patent/EP1100951B1/en not_active Expired - Lifetime
- 1999-07-23 AU AU50680/99A patent/AU5068099A/en not_active Abandoned
- 1999-07-23 CA CA002338756A patent/CA2338756A1/en not_active Abandoned
- 1999-07-23 US US09/359,678 patent/US6124122A/en not_active Expired - Fee Related
- 1999-07-23 KR KR1019990030062A patent/KR100308524B1/ko not_active Expired - Fee Related
- 1999-07-23 WO PCT/KR1999/000395 patent/WO2000005399A1/en not_active Ceased
- 1999-07-23 US US09/359,679 patent/US6221639B1/en not_active Expired - Fee Related
- 1999-07-23 CA CA002338527A patent/CA2338527A1/en not_active Abandoned
- 1999-07-23 JP JP2000561348A patent/JP3614367B2/ja not_active Expired - Fee Related
- 1999-07-23 DE DE69903441T patent/DE69903441T2/de not_active Expired - Fee Related
- 1999-07-23 KR KR1019990030063A patent/KR100324476B1/ko not_active Expired - Fee Related
- 1999-07-23 ES ES99935130T patent/ES2183586T3/es not_active Expired - Lifetime
- 1999-07-23 JP JP2000561345A patent/JP3512741B2/ja not_active Expired - Fee Related
- 1999-07-23 AU AU50677/99A patent/AU5067799A/en not_active Abandoned
- 1999-07-23 KR KR1019990030065A patent/KR100310935B1/ko not_active Expired - Fee Related
- 1999-07-23 EP EP99935129A patent/EP1100948A1/en not_active Withdrawn
- 1999-07-23 US US09/359,676 patent/US6288272B1/en not_active Expired - Fee Related
- 1999-07-23 CN CNB998103721A patent/CN1160468C/zh not_active Expired - Fee Related
- 1999-07-23 DE DE69903442T patent/DE69903442T2/de not_active Expired - Fee Related
- 1999-07-23 EP EP99935128A patent/EP1100952B1/en not_active Expired - Lifetime
- 1999-07-23 WO PCT/KR1999/000396 patent/WO2000005400A1/en not_active Ceased
- 1999-07-23 AU AU50676/99A patent/AU5067699A/en not_active Abandoned
- 1999-07-23 JP JP2000561347A patent/JP3364482B2/ja not_active Expired - Fee Related
- 1999-07-23 AU AU50678/99A patent/AU5067899A/en not_active Abandoned
- 1999-07-23 US US09/359,712 patent/US6251642B1/en not_active Expired - Fee Related
- 1999-07-23 ES ES99935131T patent/ES2183587T3/es not_active Expired - Lifetime
- 1999-07-23 JP JP2000561346A patent/JP3614366B2/ja not_active Expired - Fee Related
- 1999-07-23 WO PCT/KR1999/000398 patent/WO2000005401A1/en not_active Ceased
- 1999-07-23 CN CNB998103144A patent/CN1166781C/zh not_active Expired - Fee Related
- 1999-07-23 DE DE69903444T patent/DE69903444T2/de not_active Expired - Fee Related
- 1999-07-23 KR KR1019990030066A patent/KR100324475B1/ko not_active Expired - Fee Related
- 1999-07-23 CN CNB998103160A patent/CN1166782C/zh not_active Expired - Fee Related
- 1999-07-23 ES ES99935127T patent/ES2183584T3/es not_active Expired - Lifetime
- 1999-07-23 CA CA002338752A patent/CA2338752A1/en not_active Abandoned
- 1999-07-23 CA CA002338757A patent/CA2338757A1/en not_active Abandoned
- 1999-07-23 DE DE69903443T patent/DE69903443T2/de not_active Expired - Fee Related
- 1999-07-23 CN CN99810313A patent/CN1316008A/zh active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
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