ES2088973T3 - Cloracion mejorada de 6-esteres de sacarosa. - Google Patents
Cloracion mejorada de 6-esteres de sacarosa.Info
- Publication number
- ES2088973T3 ES2088973T3 ES90307784T ES90307784T ES2088973T3 ES 2088973 T3 ES2088973 T3 ES 2088973T3 ES 90307784 T ES90307784 T ES 90307784T ES 90307784 T ES90307784 T ES 90307784T ES 2088973 T3 ES2088973 T3 ES 2088973T3
- Authority
- ES
- Spain
- Prior art keywords
- sacarosa
- improved
- high temperature
- ester chlorination
- chlorination
- 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
- 238000005660 chlorination reaction Methods 0.000 title abstract 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 title 1
- 229930006000 Sucrose Natural products 0.000 title 1
- 239000011541 reaction mixture Substances 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
PROCESO PARA LA CLORINACION PARA PRODUCIR 6,4,1-TRICLOROSUCROSA-6-ESTERES QUE COMPRENDE LOS PASOS DE: (A)AÑADIR 7 MOLARES EQUIVALENTES DE UN ACIDO CLORURO A UNA MEZCLA DE REACCION CON 6 ESTERES DE SUCROSA; (B) UNIR EL PRODUCTO DE LA MEZCLA DE REACCION DEL PASO (A) A UNA TEMPERATURA ELEVADA NO SUPERIOR A 85 NUEVA TEMPERATURA ELEVADA NOI SUPERIOR A 125
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/382,147 US4980463A (en) | 1989-07-18 | 1989-07-18 | Sucrose-6-ester chlorination |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2088973T3 true ES2088973T3 (es) | 1996-10-01 |
Family
ID=23507711
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES90307784T Expired - Lifetime ES2088973T3 (es) | 1989-07-18 | 1990-07-17 | Cloracion mejorada de 6-esteres de sacarosa. |
Country Status (26)
Country | Link |
---|---|
US (1) | US4980463A (es) |
EP (1) | EP0409549B1 (es) |
JP (1) | JP3183506B2 (es) |
KR (1) | KR0144344B1 (es) |
AR (1) | AR247401A1 (es) |
AT (1) | ATE133175T1 (es) |
AU (1) | AU625908B2 (es) |
CA (1) | CA2021632C (es) |
DE (1) | DE69024868T2 (es) |
DK (1) | DK0409549T3 (es) |
ES (1) | ES2088973T3 (es) |
FI (1) | FI95802C (es) |
GR (1) | GR1002037B (es) |
IE (1) | IE69961B1 (es) |
IL (1) | IL94994A (es) |
MX (1) | MX164442B (es) |
NO (1) | NO175532C (es) |
NZ (1) | NZ234468A (es) |
PE (1) | PE21591A1 (es) |
PH (1) | PH26799A (es) |
PT (1) | PT94719B (es) |
RU (1) | RU1836377C (es) |
TR (1) | TR28705A (es) |
TW (1) | TW219939B (es) |
YU (1) | YU47948B (es) |
ZA (1) | ZA905615B (es) |
Families Citing this family (89)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5136031A (en) * | 1990-07-09 | 1992-08-04 | Tate & Lyle Public Limited Company | Chlorination of sugars |
US5470969A (en) * | 1990-08-27 | 1995-11-28 | Mcneil-Ppc, Inc. | Catalyzed sucrose-6-ester process |
GB9110931D0 (en) * | 1991-05-21 | 1991-07-10 | Tate & Lyle Plc | Process for the preparation of sucrose 6-esters |
US5298611A (en) * | 1993-03-12 | 1994-03-29 | Mcneil-Ppc, Inc. | Sucralose pentaester production |
IL114551A0 (en) | 1994-07-11 | 1995-11-27 | Us Agriculture | Chemically synthesized sugar esters for the control of soft bodied arthropods |
US6608039B1 (en) | 1994-07-11 | 2003-08-19 | The United States Of America As Represented By The Secretary Of Agriculture | Chemically synthesized sugar esters for the control of soft-bodied arthropods |
US5498709A (en) | 1994-10-17 | 1996-03-12 | Mcneil-Ppc, Inc. | Production of sucralose without intermediate isolation of crystalline sucralose-6-ester |
KR100405203B1 (ko) * | 1996-05-23 | 2004-02-14 | 비앤티엔지니어링(주) | 암거배수로관 |
NZ337573A (en) * | 1997-02-13 | 2000-06-23 | Mcneil Ppc Inc | Chromatographic purification of chlorinated sucrose |
RU2217435C2 (ru) * | 1998-05-15 | 2003-11-27 | Ростислав Георгиевич Жбанков | Способ получения 4,1'6'-трихлор-4,1',6'-тридезоксигалактосахарозы |
DE19924770A1 (de) * | 1999-05-29 | 2000-12-21 | Buna Sow Leuna Olefinverb Gmbh | Verfahren zur Herstellung von Polyetherpolyolen aus Polysacchariden und deren Verwendung für die Herstellung von PUR-Schäumen |
US6500973B2 (en) | 2000-06-02 | 2002-12-31 | Eastman Chemical Company | Extractive solution crystallization of chemical compounds |
US6667397B2 (en) * | 2000-08-25 | 2003-12-23 | Eastman Chemical Company | Methods of preparing disaccharide and trisaccharide C6-C12 fatty acid esters with high alpha content and materials therefrom |
ATE387457T1 (de) * | 2000-08-25 | 2008-03-15 | Eastman Chem Co | Verfahren zur herstellung von disaccharid und trisaccharid c6-c12 fettsäure-estern mit hohem alpha gehalt und materialien davon |
CN1294139C (zh) * | 2000-11-17 | 2007-01-10 | 塔特和莱利有限公司 | 改进的三氯蔗糖组合物及其制备方法 |
US6998480B2 (en) | 2002-03-08 | 2006-02-14 | Tate & Lyle Public Limited Company | Process for improving sucralose purity and yield |
US7049435B2 (en) | 2002-03-08 | 2006-05-23 | Tate & Lyle Public Limited Company | Extractive methods for purifying sucralose |
US6890581B2 (en) * | 2002-04-05 | 2005-05-10 | Tate & Lyle Public Limited Company | Methods for buffer stabilized aqueous deacylation |
US20040170735A2 (en) * | 2002-04-05 | 2004-09-02 | Mcneil-Ppc, Inc. | Methods and compositions for altering the sweetness delivery profile of sucralose |
US20040086605A1 (en) * | 2002-10-30 | 2004-05-06 | Sox Thomas E. | Composition for delivering a high intensity sweetener |
US6943248B2 (en) | 2003-04-30 | 2005-09-13 | Tate & Lyle Public Limited Company | Crystalline form of sucralose, and method for producing it |
CN1176094C (zh) * | 2003-05-23 | 2004-11-17 | 广东省食品工业研究所 | 一种三氯蔗糖的合成方法 |
US20050196503A1 (en) * | 2004-03-05 | 2005-09-08 | Sunil Srivastava | High-intensity sweetener-polyol compositions |
MXPA06010665A (es) * | 2004-03-19 | 2007-03-28 | Pharmed Medicare Pvt Ltd | Un proceso mejorado para producir sacarosa clorada. |
US20050214425A1 (en) * | 2004-03-23 | 2005-09-29 | Roma Vazirani | Sugar substitute prepared with nutritive and high-intensity sweeteners |
US20080125584A1 (en) * | 2004-12-10 | 2008-05-29 | Rakesh Ratnam | Salts Assisted Selective Extraction Of 6-Acetyl- 4,1' , 6' Trichlorogalactosucrose And 4,1', 6' Trichlorogalactosucrosse From Aqueous Reaction Mixture |
CN101098972A (zh) * | 2004-12-10 | 2008-01-02 | 法马德医疗保险私人有限公司 | 硅烷化硅胶色谱纯化6-乙酰基-4,1',6'三氯半乳蔗糖和4,1',6'三氯半乳蔗糖的改良方法 |
WO2006061854A2 (en) * | 2004-12-10 | 2006-06-15 | Pharmed Medicare Private Limited | CONTROL OF pH BY DIRECT ADDITION OF CARBONATES AND BICARBONATES DURING CONCENTRATION OF ORGANIC SOLVENT EXTRACTS OF 6- ACETYL- 4,1 ‘, 6' TRICHLOROGALACTOSUCROSE AND 4,1 ‘, 6' TRICHLOROGALACTOSUCROSE |
KR20070113194A (ko) * | 2005-01-03 | 2007-11-28 | 팜드 메디케어 프리베이트 리미티드 | 염소화 시약의 동시 첨가에 의한 수크로스-6-에스테르염소화 |
US20060188629A1 (en) * | 2005-01-21 | 2006-08-24 | Greg Liesen | Method for the purification of sucralose |
US20080163867A1 (en) * | 2005-02-22 | 2008-07-10 | Molecular Separation Process in Various Steps of Process for Production of Chlorinated Sugars, Their Precursors and Derivatives | |
US20060205936A1 (en) * | 2005-03-14 | 2006-09-14 | Sl Laboratories, Llc | Chlorination of Sucrose-6-esters |
US20060247180A1 (en) * | 2005-04-29 | 2006-11-02 | Bergey James L | Purgative composition and uses thereof |
GB2442619B (en) * | 2005-05-04 | 2010-05-26 | Pharmed Medicare Pvt Ltd | Chlorination of sucrose acylates using triphosgene |
CN101490070A (zh) * | 2005-05-04 | 2009-07-22 | V.B.医疗保险私人有限公司 | 由五氯化磷和dmf产生副产物磷酰氯以及其通过转变成vilsmeier-haack试剂在氯化反应中的应用 |
US20060276639A1 (en) * | 2005-06-01 | 2006-12-07 | Healthy Brands, Llc | Conversion of sucralose-6-ester to sucralose |
KR20080016826A (ko) * | 2005-06-01 | 2008-02-22 | 팜드 메디케어 프리베이트 리미티드 | 용매 추출에 의한 염소화 수크로스 유도체의 정제 방법 |
WO2007057920A2 (en) * | 2005-09-22 | 2007-05-24 | Pharmed Medicare Pvt. Ltd. | Novel preparation of 6-o-acyl chlorosucrose from anhydrous chlorinated reaction mass |
US20070100139A1 (en) * | 2005-10-31 | 2007-05-03 | Healthy Brands, Llc | Methods for chlorinating sucrose-6-ester |
US7741477B2 (en) * | 2006-01-10 | 2010-06-22 | Alembic Limited | Process for purification of sucralose |
MX2008010982A (es) * | 2006-02-28 | 2008-10-21 | V B Medicare Private Ltd | Reactivo novedosos de cloracion y proceso novedoso para la cloracion de azucares que usa cloruro de tionilo. |
CN100418976C (zh) * | 2006-04-03 | 2008-09-17 | 广州科宏食品添加物有限公司 | 一种三氯蔗糖的制备方法 |
CN100402541C (zh) * | 2006-06-15 | 2008-07-16 | 浙江工业大学 | 一种三氯蔗糖-6-乙酯的合成方法 |
CN101092438A (zh) * | 2006-06-22 | 2007-12-26 | 南京莱因医药科技有限公司 | 6-o-苯甲酰三氯半乳型蔗糖四乙酯的制备方法 |
US20090312538A1 (en) * | 2006-07-06 | 2009-12-17 | Alembic Limited | process for the preparation of sucralose of high purity |
CN100420697C (zh) * | 2006-08-30 | 2008-09-24 | 河北苏科瑞科技有限公司 | 一种制备蔗糖-6-有机酸酯的方法 |
US8258291B2 (en) * | 2006-10-25 | 2012-09-04 | Mamtek International Limited | Process for the preparation of sucralose by the chlorination of sugar with triphosgene (BTC) |
US20080103295A1 (en) * | 2006-10-25 | 2008-05-01 | David Losan Ho | Process for the preparation of sucrose-6-ester by esterification in the presence of solid superacid catalyst |
GB0702857D0 (en) * | 2007-01-19 | 2007-03-28 | Tate & Lyle Plc | Improved sucralose production method |
US20080227971A1 (en) * | 2007-01-19 | 2008-09-18 | Leinhos Duane A | Deacylation of sucralose-6-acylates |
CN101260127B (zh) * | 2007-03-06 | 2011-04-20 | 盐城捷康三氯蔗糖制造有限公司 | 由三氯蔗糖-6-乙酯脱乙酰基合成三氯蔗糖的方法 |
US20080300392A1 (en) * | 2007-06-04 | 2008-12-04 | Polymed Therapeutics, Inc. | Novel chlorination process for preparing sucralose |
US20080300401A1 (en) * | 2007-06-04 | 2008-12-04 | Polymed Therapeutics, Inc. | Novel chlorination process for preparing sucralose |
AR070082A1 (es) * | 2008-01-04 | 2010-03-10 | Tate & Lyle Technology Ltd | Metodo para la produccion de sucralosa |
US7932380B2 (en) * | 2008-03-06 | 2011-04-26 | Wanhe International (Group) Co. Ltd. | Process for the preparation of sucralose |
US8557976B2 (en) * | 2008-03-13 | 2013-10-15 | Tate & Lyle Technology Limited | Microbial consortia and methods for their use |
US8476424B2 (en) * | 2008-03-20 | 2013-07-02 | Tate & Lyle Technology Limited | Removal of acids from tertiary amide solvents |
US8436157B2 (en) * | 2008-03-26 | 2013-05-07 | Tate & Lyle Technology Limited | Method for the production of sucralose |
US20090299055A1 (en) * | 2008-04-03 | 2009-12-03 | Tate & Lyle Technology Limited | Purification of Sucralose Containing Feed Streams for Sucralose Crystallization |
AR071134A1 (es) * | 2008-04-03 | 2010-05-26 | Tate & Lyle Technology Ltd | Cristalizacion de sucralosa a partir de chorros que contienen sucralosa |
EP2260049B1 (en) * | 2008-04-03 | 2013-02-27 | Tate & Lyle Technology Limited | Effect of carbohydrate concentration on sucralose extraction efficiency |
US20090259036A1 (en) * | 2008-04-03 | 2009-10-15 | Tate & Lyle Technology Limited | Extraction of less polar impurities from sucralose containing aqueous feed streams |
US8497367B2 (en) * | 2008-04-03 | 2013-07-30 | Tate & Lyle Technology Limited | Sucralose purification process |
US20100022765A1 (en) * | 2008-07-23 | 2010-01-28 | David Losan Ho | Methods for extracting and purifying sucralose intermediate |
US7862744B2 (en) * | 2008-07-23 | 2011-01-04 | Mamtek International Limited | Methods and systems for preparing materials for sucralose production |
GB2468936B (en) | 2009-03-27 | 2011-09-07 | Mohamad Rami Radwan Jaber | Chlorination of sucrose-6-esters |
GB2469157B (en) * | 2009-03-30 | 2011-07-06 | John Kerr | Process for removing dimethylamine during sucralose production |
GB2469158B (en) * | 2009-03-31 | 2011-09-28 | Peter J Seaberg | Base-assisted formation of tin-sucrose adducts |
GB2471348B (en) | 2009-06-22 | 2011-12-14 | Tate & Lyle Technology Ltd | A method for producing sucralose-6-acylate |
GB2474311B (en) | 2009-10-12 | 2012-10-17 | Tate & Lyle Technology Ltd | Low temperature, single solvent process for the production of sucrose-6-ester |
GB2474310B (en) | 2009-10-12 | 2012-02-29 | Tate & Lyle Technology Ltd | Process for the production of sucrose-6-ester |
EP2609120B1 (en) * | 2010-08-25 | 2015-07-29 | Davuluri, Ramamohan Rao | Improved process for preparation of sugammadex |
SG190083A1 (en) | 2010-11-23 | 2013-06-28 | Lexington Pharmaceuticals Lab Llc | Low temperature chlorination of carbohydrates |
GB201110520D0 (en) | 2011-05-10 | 2011-08-03 | Tate & Lyle Technology Ltd | Extraction of carboxylic acids with tin compounds |
JP5679447B2 (ja) * | 2011-06-20 | 2015-03-04 | 第一工業製薬株式会社 | ショ糖ベンゾエート組成物の製造方法 |
US8884004B2 (en) | 2011-09-02 | 2014-11-11 | Divi's Laboratories, Ltd. | Process for the preparation of sucralose |
DK2646452T3 (da) * | 2011-10-14 | 2016-06-20 | Lexington Pharmaceutical Laboratories Llc | Chlorering af carbohydrater og carbohydratderivater |
CN102964396B (zh) * | 2012-10-26 | 2015-11-18 | 溧阳维信生物科技有限公司 | 一种三氯蔗糖-6-乙酯重结晶的方法 |
JP6109531B2 (ja) * | 2012-11-02 | 2017-04-05 | 第一工業製薬株式会社 | 溶媒の除去方法 |
CN103145772A (zh) * | 2013-03-26 | 2013-06-12 | 山东金城柯瑞化学有限公司 | 三氯蔗糖的制备方法 |
GB2539112B (en) | 2013-12-16 | 2020-11-04 | Tate & Lyle Tech Ltd | Chlorination of sucrose-6-esters |
CN106573949B (zh) * | 2014-08-08 | 2019-03-15 | 塔特和莱利技术有限公司 | 蔗糖-6-酯的氯化 |
CN104387427A (zh) * | 2014-10-30 | 2015-03-04 | 安徽金禾实业股份有限公司 | 一种三氯蔗糖的生产方法 |
GB2536480B (en) | 2015-03-17 | 2019-09-04 | Tate & Lyle Tech Ltd | DMF Distillation |
CN105131050B (zh) * | 2015-07-22 | 2018-07-31 | 青岛科技大学 | 一种氯化剂的制备方法及其制备三氯蔗糖的方法 |
CN105859802B (zh) * | 2016-05-14 | 2019-02-12 | 广西科技大学 | 一种三氯蔗糖的结晶和纯化方法 |
GB2551591B (en) | 2016-06-23 | 2019-08-07 | Tate & Lyle Tech Ltd | Liquid-liquid extraction of DMF |
US20230374054A1 (en) | 2020-09-30 | 2023-11-23 | Anhui Jinhe Industrial Co., Ltd. | Method for purifying sucralose |
CN113699196A (zh) * | 2021-08-17 | 2021-11-26 | 安徽金禾实业股份有限公司 | 一种蔗糖-6-乙酸酯的无水酶法催化合成方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4435440A (en) * | 1976-01-08 | 1984-03-06 | Tate & Lyle Limited | Sweeteners |
EP0010410B1 (en) * | 1978-10-18 | 1982-03-03 | TATE & LYLE PATENT HOLDINGS LIMITED | A method for the preparation of 2-chloro-2-deoxy saccharides and some 2-chloro-2-deoxy saccharides |
US4324888A (en) * | 1979-03-09 | 1982-04-13 | Talres Development (N.A.) N.V. | Process for the preparation of chlorodeoxysugars |
DE3062467D1 (en) * | 1979-12-20 | 1983-04-28 | Tate & Lyle Plc | Process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxy-galactosucrose |
US4291158A (en) * | 1980-01-28 | 1981-09-22 | Velsicol Chemical Corporation | Sucrose ester of 2-methoxy-3,6-dichlorobenzoic acid |
US4345933A (en) * | 1980-01-28 | 1982-08-24 | Velsicol Chemical Corporation | Sucrose ester of 2-methoxy-3,6-dichlorobenzoic acid |
DE3165986D1 (en) * | 1980-07-08 | 1984-10-18 | Tate & Lyle Plc | Process for the preparation of 4, 1',6'-trichloro-4,1',6'-trideoxygalactosucrose (tgs) |
DK160315C (da) * | 1982-09-13 | 1991-07-29 | Tate & Lyle Plc | Saccharosederivater, en fremgangsmaade til soedning af et spiseligt produkt af ikke-naeringsmiddelmaessig art eller et oralt praeparat samt et soedepraeparat |
GB8316790D0 (en) * | 1983-06-21 | 1983-07-27 | Tate & Lyle Plc | Chemical process |
GB8622345D0 (en) * | 1986-09-17 | 1986-10-22 | Tate & Lyle Plc | Sucrose derivatives |
-
1989
- 1989-07-18 US US07/382,147 patent/US4980463A/en not_active Expired - Lifetime
-
1990
- 1990-07-06 PH PH40800A patent/PH26799A/en unknown
- 1990-07-06 IL IL9499490A patent/IL94994A/en unknown
- 1990-07-11 NZ NZ234468A patent/NZ234468A/en unknown
- 1990-07-12 GR GR900100537A patent/GR1002037B/el not_active IP Right Cessation
- 1990-07-16 CA CA002021632A patent/CA2021632C/en not_active Expired - Lifetime
- 1990-07-16 PE PE1990172224A patent/PE21591A1/es not_active Application Discontinuation
- 1990-07-17 RU SU4830726A patent/RU1836377C/ru active
- 1990-07-17 AT AT90307784T patent/ATE133175T1/de not_active IP Right Cessation
- 1990-07-17 NO NO903190A patent/NO175532C/no not_active IP Right Cessation
- 1990-07-17 AR AR90317395A patent/AR247401A1/es active
- 1990-07-17 ES ES90307784T patent/ES2088973T3/es not_active Expired - Lifetime
- 1990-07-17 DK DK90307784.0T patent/DK0409549T3/da active
- 1990-07-17 IE IE260390A patent/IE69961B1/en not_active IP Right Cessation
- 1990-07-17 DE DE69024868T patent/DE69024868T2/de not_active Expired - Lifetime
- 1990-07-17 PT PT94719A patent/PT94719B/pt not_active IP Right Cessation
- 1990-07-17 FI FI903603A patent/FI95802C/fi not_active IP Right Cessation
- 1990-07-17 EP EP90307784A patent/EP0409549B1/en not_active Expired - Lifetime
- 1990-07-17 JP JP18732890A patent/JP3183506B2/ja not_active Expired - Fee Related
- 1990-07-17 AU AU59069/90A patent/AU625908B2/en not_active Expired
- 1990-07-17 ZA ZA905615A patent/ZA905615B/xx unknown
- 1990-07-18 MX MX21634A patent/MX164442B/es unknown
- 1990-07-18 KR KR1019900010857A patent/KR0144344B1/ko not_active IP Right Cessation
- 1990-07-18 YU YU141190A patent/YU47948B/sh unknown
- 1990-07-18 TR TR00678/90A patent/TR28705A/xx unknown
- 1990-07-26 TW TW079106171A patent/TW219939B/zh active
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