NO319415B1 - Mikrobiell fremstilling av actinol - Google Patents
Mikrobiell fremstilling av actinol Download PDFInfo
- Publication number
- NO319415B1 NO319415B1 NO19993987A NO993987A NO319415B1 NO 319415 B1 NO319415 B1 NO 319415B1 NO 19993987 A NO19993987 A NO 19993987A NO 993987 A NO993987 A NO 993987A NO 319415 B1 NO319415 B1 NO 319415B1
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- trimethylcyclohexanone
- ferm
- actinol
- reaction mixture
- Prior art date
Links
- CSPVUHYZUZZRGF-RNFRBKRXSA-N (4R,6R)-hydroxy-2,2,6-trimethylcyclohexanone Chemical compound C[C@@H]1C[C@@H](O)CC(C)(C)C1=O CSPVUHYZUZZRGF-RNFRBKRXSA-N 0.000 title claims abstract description 41
- 229930185327 Actinol Natural products 0.000 title description 31
- 230000000813 microbial effect Effects 0.000 title description 3
- 244000005700 microbiome Species 0.000 claims abstract description 32
- 239000011541 reaction mixture Substances 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 19
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- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 claims abstract description 7
- XJLXINKUBYWONI-NNYOXOHSSA-O NADP(+) Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-NNYOXOHSSA-O 0.000 claims abstract description 7
- 239000008103 glucose Substances 0.000 claims abstract description 7
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- 241000193804 Planococcus <bacterium> Species 0.000 claims abstract description 5
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- 241000186321 Cellulomonas Species 0.000 claims abstract description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- 241001288676 Leifsonia aquatica Species 0.000 claims description 17
- 241000120652 Cellulomonas sp. Species 0.000 claims description 9
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- 150000001413 amino acids Chemical class 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 4
- 235000019797 dipotassium phosphate Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000186031 Corynebacteriaceae Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 229950006238 nadide Drugs 0.000 description 3
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- 229920000136 polysorbate Polymers 0.000 description 3
- 239000008057 potassium phosphate buffer Substances 0.000 description 3
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- 238000011946 reduction process Methods 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
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- 238000005273 aeration Methods 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960003104 ornithine Drugs 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- CSPVUHYZUZZRGF-UHFFFAOYSA-N 4-hydroxy-2,2,6-trimethylcyclohexan-1-one Chemical class CC1CC(O)CC(C)(C)C1=O CSPVUHYZUZZRGF-UHFFFAOYSA-N 0.000 description 1
- 241000770536 Bacillus thermophilus Species 0.000 description 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- HVHHZSFNAYSPSA-UHFFFAOYSA-N Dihydrooxoisophorone Natural products CC1CC(=O)CC(C)(C)C1=O HVHHZSFNAYSPSA-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011942 biocatalyst Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
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- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000003495 flagella Anatomy 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000001641 gel filtration chromatography Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 210000001822 immobilized cell Anatomy 0.000 description 1
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- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
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- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- 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
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
-
- 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
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- 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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/002—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by oxidation/reduction reactions
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/06—Arthrobacter
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/15—Corynebacterium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98115564 | 1998-08-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO993987D0 NO993987D0 (no) | 1999-08-18 |
| NO993987L NO993987L (no) | 2000-02-21 |
| NO319415B1 true NO319415B1 (no) | 2005-08-08 |
Family
ID=8232480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19993987A NO319415B1 (no) | 1998-08-19 | 1999-08-18 | Mikrobiell fremstilling av actinol |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6444460B1 (id) |
| EP (1) | EP0982406B1 (id) |
| JP (1) | JP3897489B2 (id) |
| KR (1) | KR100602296B1 (id) |
| CN (1) | CN1246466C (id) |
| AT (1) | ATE318925T1 (id) |
| AU (1) | AU753590B2 (id) |
| BR (1) | BR9903739A (id) |
| CA (1) | CA2280350A1 (id) |
| DE (1) | DE69930031T2 (id) |
| ES (1) | ES2259224T3 (id) |
| ID (1) | ID23839A (id) |
| NO (1) | NO319415B1 (id) |
| TW (1) | TWI229697B (id) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000057820A (ko) | 1999-02-01 | 2000-09-25 | 프리돌린 클라우스너, 롤란드 비. 보레르 | 레보디온 리덕테이즈 |
| CA2330023A1 (en) | 2000-02-01 | 2001-08-01 | F. Hoffmann-La Roche Ag | Levodione reductase gene and use thereof |
| US20060121586A1 (en) * | 2002-07-04 | 2006-06-08 | Tatsuo Hoshino | Process for producing phorenol |
| WO2004029263A2 (en) * | 2002-09-27 | 2004-04-08 | Dsm Ip Assets B.V. | Process for actinol production from ketoisophorone |
| US20090269852A1 (en) * | 2005-09-09 | 2009-10-29 | Masako Shinjoh | Novel gene gms 01 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1041904B (it) * | 1974-08-21 | 1980-01-10 | Hoffmann La Roche | Procedimento per la preparazione di derivati del cicloesano otticamente attivi |
| US3988205A (en) | 1974-08-21 | 1976-10-26 | Hoffmann-La Roche Inc. | Optically active cyclohexane derivatives |
| US5385833A (en) * | 1992-02-26 | 1995-01-31 | The Scripps Research Institute | Pseudomonas sp. ATCC No. 49794 alcohol dehydrogenase |
-
1999
- 1999-08-10 DE DE69930031T patent/DE69930031T2/de not_active Expired - Lifetime
- 1999-08-10 ES ES99115723T patent/ES2259224T3/es not_active Expired - Lifetime
- 1999-08-10 EP EP99115723A patent/EP0982406B1/en not_active Expired - Lifetime
- 1999-08-10 AT AT99115723T patent/ATE318925T1/de not_active IP Right Cessation
- 1999-08-16 ID IDP990789D patent/ID23839A/id unknown
- 1999-08-16 US US09/375,129 patent/US6444460B1/en not_active Expired - Lifetime
- 1999-08-17 CA CA002280350A patent/CA2280350A1/en not_active Abandoned
- 1999-08-18 BR BR9903739-4A patent/BR9903739A/pt not_active IP Right Cessation
- 1999-08-18 KR KR1019990034138A patent/KR100602296B1/ko not_active IP Right Cessation
- 1999-08-18 AU AU44553/99A patent/AU753590B2/en not_active Ceased
- 1999-08-18 JP JP23114399A patent/JP3897489B2/ja not_active Expired - Fee Related
- 1999-08-18 NO NO19993987A patent/NO319415B1/no unknown
- 1999-08-18 CN CNB991179838A patent/CN1246466C/zh not_active Expired - Fee Related
- 1999-08-19 TW TW088114151A patent/TWI229697B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO993987L (no) | 2000-02-21 |
| CN1254760A (zh) | 2000-05-31 |
| DE69930031T2 (de) | 2006-09-28 |
| US6444460B1 (en) | 2002-09-03 |
| DE69930031D1 (de) | 2006-04-27 |
| BR9903739A (pt) | 2000-10-17 |
| TWI229697B (en) | 2005-03-21 |
| EP0982406B1 (en) | 2006-03-01 |
| EP0982406A2 (en) | 2000-03-01 |
| AU753590B2 (en) | 2002-10-24 |
| KR20000017373A (ko) | 2000-03-25 |
| AU4455399A (en) | 2000-03-09 |
| CA2280350A1 (en) | 2000-02-19 |
| ID23839A (id) | 2000-05-25 |
| ATE318925T1 (de) | 2006-03-15 |
| ES2259224T3 (es) | 2006-09-16 |
| EP0982406A3 (en) | 2000-09-20 |
| JP2000069986A (ja) | 2000-03-07 |
| KR100602296B1 (ko) | 2006-07-14 |
| CN1246466C (zh) | 2006-03-22 |
| JP3897489B2 (ja) | 2007-03-22 |
| NO993987D0 (no) | 1999-08-18 |
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