DE3541186A1 - Wasserloesliche, stabilisierte peroxidasederivate, verfahren zu ihrer herstellung und verwendung zur bestimmung von wasserstoffperoxid - Google Patents
Wasserloesliche, stabilisierte peroxidasederivate, verfahren zu ihrer herstellung und verwendung zur bestimmung von wasserstoffperoxidInfo
- Publication number
- DE3541186A1 DE3541186A1 DE19853541186 DE3541186A DE3541186A1 DE 3541186 A1 DE3541186 A1 DE 3541186A1 DE 19853541186 DE19853541186 DE 19853541186 DE 3541186 A DE3541186 A DE 3541186A DE 3541186 A1 DE3541186 A1 DE 3541186A1
- Authority
- DE
- Germany
- Prior art keywords
- peroxidase
- water
- soluble
- polymer
- pod
- 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- Withdrawn
Links
- 102000003992 Peroxidases Human genes 0.000 title claims abstract description 54
- 108040007629 peroxidase activity proteins Proteins 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000004676 glycans Chemical class 0.000 claims abstract description 13
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 13
- 239000005017 polysaccharide Substances 0.000 claims abstract description 13
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000003647 oxidation Effects 0.000 claims abstract description 6
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 5
- 229920003169 water-soluble polymer Polymers 0.000 claims abstract description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract 2
- 229920000642 polymer Polymers 0.000 claims description 16
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229940072417 peroxidase Drugs 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 9
- 239000003599 detergent Substances 0.000 abstract description 8
- 239000008139 complexing agent Substances 0.000 abstract description 5
- 229920002732 Polyanhydride Polymers 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 12
- 229920002307 Dextran Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 230000004913 activation Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920001917 Ficoll Polymers 0.000 description 3
- 229920005654 Sephadex Polymers 0.000 description 3
- 239000012507 Sephadex™ Substances 0.000 description 3
- 125000005263 alkylenediamine group Chemical group 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000011210 chromatographic step Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AIHDUTVBOYDXOW-UHFFFAOYSA-N 4-(dimethylamino)pyridin-1-ium-1-carbonitrile Chemical class CN(C)C1=CC=[N+](C#N)C=C1 AIHDUTVBOYDXOW-UHFFFAOYSA-N 0.000 description 1
- 101100438971 Caenorhabditis elegans mat-1 gene Proteins 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- 108700020962 Peroxidase Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000011545 carbonate/bicarbonate buffer Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- -1 cyanoborohydride Chemical compound 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 229940127121 immunoconjugate Drugs 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- 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
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/10—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a carbohydrate
-
- 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
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/96—Stabilising an enzyme by forming an adduct or a composition; Forming enzyme conjugates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
- C12Q1/28—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Biophysics (AREA)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Enzymes And Modification Thereof (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Detergent Compositions (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853541186 DE3541186A1 (de) | 1985-11-21 | 1985-11-21 | Wasserloesliche, stabilisierte peroxidasederivate, verfahren zu ihrer herstellung und verwendung zur bestimmung von wasserstoffperoxid |
| US06/930,871 US4910135A (en) | 1985-11-21 | 1986-11-14 | Water-soluble peroxidase derivatives |
| ES198686115902T ES2036519T3 (es) | 1985-11-21 | 1986-11-15 | Derivados de peroxidasa estabilizados solubles en agua, procedimiento para su preparacion y utilizacion. |
| AT86115902T ATE74961T1 (de) | 1985-11-21 | 1986-11-15 | Wasserloesliche, stabilisierte peroxidasederivate, verfahren zu ihrer herstellung und verwendung zur bestimmung von wasserstoffperoxid. |
| EP86115902A EP0223221B1 (de) | 1985-11-21 | 1986-11-15 | Wasserlösliche, stabilisierte Peroxidasederivate, Verfahren zu ihrer Herstellung und Verwendung zur Bestimmung von Wasserstoffperoxid |
| DE8686115902T DE3684879D1 (de) | 1985-11-21 | 1986-11-15 | Wasserloesliche, stabilisierte peroxidasederivate, verfahren zu ihrer herstellung und verwendung zur bestimmung von wasserstoffperoxid. |
| JP61274247A JPS62126977A (ja) | 1985-11-21 | 1986-11-19 | 水溶性の安定化されたペルオキシダ−ゼ誘導体、及びその製法 |
| GR920400771T GR3004587T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-11-21 | 1992-05-13 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853541186 DE3541186A1 (de) | 1985-11-21 | 1985-11-21 | Wasserloesliche, stabilisierte peroxidasederivate, verfahren zu ihrer herstellung und verwendung zur bestimmung von wasserstoffperoxid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3541186A1 true DE3541186A1 (de) | 1987-05-27 |
Family
ID=6286483
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853541186 Withdrawn DE3541186A1 (de) | 1985-11-21 | 1985-11-21 | Wasserloesliche, stabilisierte peroxidasederivate, verfahren zu ihrer herstellung und verwendung zur bestimmung von wasserstoffperoxid |
| DE8686115902T Expired - Lifetime DE3684879D1 (de) | 1985-11-21 | 1986-11-15 | Wasserloesliche, stabilisierte peroxidasederivate, verfahren zu ihrer herstellung und verwendung zur bestimmung von wasserstoffperoxid. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8686115902T Expired - Lifetime DE3684879D1 (de) | 1985-11-21 | 1986-11-15 | Wasserloesliche, stabilisierte peroxidasederivate, verfahren zu ihrer herstellung und verwendung zur bestimmung von wasserstoffperoxid. |
Country Status (7)
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2632518B2 (ja) * | 1987-08-28 | 1997-07-23 | 天野製薬株式会社 | ビリルビンオキシダーゼの化学修飾体 |
| USRE38385E1 (en) * | 1989-02-16 | 2004-01-13 | Nektar Therapeutics | Storage of materials |
| GB8903593D0 (en) * | 1989-02-16 | 1989-04-05 | Pafra Ltd | Storage of materials |
| US5013646A (en) * | 1989-11-03 | 1991-05-07 | Transgenic Sciences, Inc. | TMB Formulation for soluble and precipitable HRP-ELISA |
| FR2656329A1 (fr) * | 1989-12-21 | 1991-06-28 | Elf Aquitaine | Procede de production de peroxydases mn-dependantes. |
| US5112752A (en) * | 1990-10-18 | 1992-05-12 | The Mead Corporation | Biocatalytic oxidation using soybean and other legume peroxidases |
| JP3125428B2 (ja) * | 1991-03-28 | 2001-01-15 | 和光純薬工業株式会社 | 修飾酵素 |
| AU659645B2 (en) | 1991-06-26 | 1995-05-25 | Inhale Therapeutic Systems | Storage of materials |
| CA2091544A1 (en) * | 1992-03-26 | 1993-09-27 | Shing F. Kwan | Stabilization of functional proteins |
| AU662235B2 (en) * | 1992-09-04 | 1995-08-24 | Becton Dickinson & Company | Intrinsic factor - horseradish peroxidase conjugates |
| US5849301A (en) * | 1993-09-22 | 1998-12-15 | Henry M. Jackson Foundation For The Advancement Of Military Medicine | Producing immunogenic constructs using soluable carbohydrates activated via organic cyanylating reagents |
| JP3828145B2 (ja) * | 1993-09-22 | 2006-10-04 | ヘンリー エム．ジャクソン ファウンデイション フォー ザ アドバンスメント オブ ミリタリー メディスン | 免疫原性構成物の製造のための新規シアン化試薬を使った可溶性炭水化物の活性化方法 |
| US6290991B1 (en) | 1994-12-02 | 2001-09-18 | Quandrant Holdings Cambridge Limited | Solid dose delivery vehicle and methods of making same |
| US5856451A (en) * | 1994-12-07 | 1999-01-05 | Novo Nordisk A/S | Method for reducing respiratory allergenicity |
| DE19506262A1 (de) * | 1995-02-23 | 1996-08-29 | Behringwerke Ag | Störungsvermindertes Redox-Nachweissystem |
| ES2200059T3 (es) * | 1995-03-22 | 2004-03-01 | Henry M. Jackson Foundation For The Advancement Of Military Medicine | Produccion de construcciones inmunogenicas usando carbohidratos solubles activados mediante reactivos cianilados organicos. |
| DE122009000056I1 (de) * | 1995-03-22 | 2010-01-28 | Jackson H M Found Military Med | Herstellung von immunogenen konstrukten unter verwendung von löslichen kohlehydraten, die durch organische cyanylierungs-reagenzien aktiviert wurden |
| US6309671B1 (en) | 1995-04-14 | 2001-10-30 | Inhale Therapeutic Systems | Stable glassy state powder formulations |
| GB9508691D0 (en) * | 1995-04-28 | 1995-06-14 | Pafra Ltd | Stable compositions |
| EP0874893A2 (en) * | 1995-12-29 | 1998-11-04 | The Procter & Gamble Company | Detergent compositions comprising immobilized enzymes |
| WO1997030148A1 (en) * | 1996-02-15 | 1997-08-21 | Novo Nordisk A/S | Conjugation of polypeptides |
| US6309646B1 (en) | 1996-05-09 | 2001-10-30 | The Henry M. Jackson Foundation For The Advancement Of Military Medicine | Protein-polysaccharide conjugate vaccines and other immunological reagents prepared using homobifunctional and heterobifunctional vinylsulfones, and processes for preparing the conjugates |
| KR20140097115A (ko) | 2011-08-26 | 2014-08-06 | 아비아나 몰레큘라 테크놀로지스 엘엘씨 | 현장 진단용 바이오 코팅 압전 바이오센서 플랫폼 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3860484A (en) * | 1972-09-28 | 1975-01-14 | Xerox Corp | Enzyme stabilization |
| JPS536483A (en) * | 1976-07-02 | 1978-01-20 | Tanabe Seiyaku Co Ltd | Composition having enzymatic activity and its preparation |
| GB2055847A (en) * | 1979-07-30 | 1981-03-11 | Bull F G | Process for the production of carrier particles |
| US4652524A (en) * | 1980-10-02 | 1987-03-24 | Ivan E. Modrovich | Soluble stabilized enzymes |
| DE3126759A1 (de) * | 1981-07-07 | 1983-01-27 | Boehringer Mannheim Gmbh, 6800 Mannheim | Loesliche leber-uricase, verfahren zu ihrer herstellung und verwendung |
| JPS5951789A (ja) * | 1982-09-18 | 1984-03-26 | Wako Pure Chem Ind Ltd | 安定化酵素 |
-
1985
- 1985-11-21 DE DE19853541186 patent/DE3541186A1/de not_active Withdrawn
-
1986
- 1986-11-14 US US06/930,871 patent/US4910135A/en not_active Expired - Lifetime
- 1986-11-15 AT AT86115902T patent/ATE74961T1/de not_active IP Right Cessation
- 1986-11-15 EP EP86115902A patent/EP0223221B1/de not_active Expired - Lifetime
- 1986-11-15 DE DE8686115902T patent/DE3684879D1/de not_active Expired - Lifetime
- 1986-11-15 ES ES198686115902T patent/ES2036519T3/es not_active Expired - Lifetime
- 1986-11-19 JP JP61274247A patent/JPS62126977A/ja active Granted
-
1992
- 1992-05-13 GR GR920400771T patent/GR3004587T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0223221A3 (en) | 1989-03-08 |
| DE3684879D1 (de) | 1992-05-21 |
| EP0223221A2 (de) | 1987-05-27 |
| GR3004587T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-04-28 |
| US4910135A (en) | 1990-03-20 |
| JPS6355918B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-11-04 |
| EP0223221B1 (de) | 1992-04-15 |
| ES2036519T3 (es) | 1993-06-01 |
| JPS62126977A (ja) | 1987-06-09 |
| ATE74961T1 (de) | 1992-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |