NO326212B1 - Fremgangsmate for fremstilling og rensing av et N-alkylert aspartamderivat - Google Patents
Fremgangsmate for fremstilling og rensing av et N-alkylert aspartamderivat Download PDFInfo
- Publication number
- NO326212B1 NO326212B1 NO19993676A NO993676A NO326212B1 NO 326212 B1 NO326212 B1 NO 326212B1 NO 19993676 A NO19993676 A NO 19993676A NO 993676 A NO993676 A NO 993676A NO 326212 B1 NO326212 B1 NO 326212B1
- Authority
- NO
- Norway
- Prior art keywords
- organic solvent
- aqueous
- methanol
- solution
- phenylalanine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 39
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical class OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 title claims description 23
- 238000000746 purification Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 120
- 239000003960 organic solvent Substances 0.000 claims description 72
- HLIAVLHNDJUHFG-HOTGVXAUSA-N neotame Chemical compound CC(C)(C)CCN[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-HOTGVXAUSA-N 0.000 claims description 26
- 239000003125 aqueous solvent Substances 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 21
- 238000001914 filtration Methods 0.000 claims description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 239000000605 aspartame Substances 0.000 claims description 15
- 229960003438 aspartame Drugs 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 108010011485 Aspartame Proteins 0.000 claims description 14
- 235000010357 aspartame Nutrition 0.000 claims description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- LTNUSYNQZJZUSY-UHFFFAOYSA-N 3,3-dimethylbutanal Chemical compound CC(C)(C)CC=O LTNUSYNQZJZUSY-UHFFFAOYSA-N 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
- 239000002244 precipitate Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- HLIAVLHNDJUHFG-UHFFFAOYSA-N neotame Chemical compound CC(C)(C)CCNC(CC(O)=O)C(=O)NC(C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 35
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 235000003599 food sweetener Nutrition 0.000 description 8
- 239000003765 sweetening agent Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- -1 3,3-dimethylbutyl Chemical group 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Peptides Or Proteins (AREA)
- Seasonings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Enzymes And Modification Thereof (AREA)
- Arrangements For Transmission Of Measured Signals (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/790,113 US5728862A (en) | 1997-01-29 | 1997-01-29 | Method for preparing and purifying an N-alkylated aspartame derivative |
PCT/US1998/001734 WO1998032767A1 (en) | 1997-01-29 | 1998-01-29 | Method for preparing and purifying an n-alkylated aspartame derivative |
Publications (3)
Publication Number | Publication Date |
---|---|
NO993676D0 NO993676D0 (no) | 1999-07-28 |
NO993676L NO993676L (no) | 1999-09-28 |
NO326212B1 true NO326212B1 (no) | 2008-10-20 |
Family
ID=25149681
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19993676A NO326212B1 (no) | 1997-01-29 | 1999-07-28 | Fremgangsmate for fremstilling og rensing av et N-alkylert aspartamderivat |
Country Status (29)
Country | Link |
---|---|
US (1) | US5728862A (et) |
EP (1) | EP0973796B1 (et) |
CN (1) | CN1136227C (et) |
AR (1) | AR011782A1 (et) |
AT (1) | ATE313555T1 (et) |
AU (1) | AU723479B2 (et) |
BG (1) | BG64562B1 (et) |
BR (1) | BR9807020B1 (et) |
CA (1) | CA2278608C (et) |
CO (1) | CO5040054A1 (et) |
CZ (1) | CZ296888B6 (et) |
DE (1) | DE69832870T2 (et) |
DK (1) | DK0973796T3 (et) |
EA (1) | EA001948B1 (et) |
EE (1) | EE03928B1 (et) |
ES (1) | ES2251765T3 (et) |
HU (1) | HU228676B1 (et) |
ID (1) | ID22966A (et) |
IL (1) | IL131140A0 (et) |
NO (1) | NO326212B1 (et) |
NZ (1) | NZ336893A (et) |
PE (1) | PE71999A1 (et) |
PL (1) | PL191750B1 (et) |
SK (1) | SK285451B6 (et) |
TR (1) | TR199901811T2 (et) |
TW (1) | TW432074B (et) |
UA (1) | UA57605C2 (et) |
UY (1) | UY24864A1 (et) |
WO (1) | WO1998032767A1 (et) |
Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6146680A (en) * | 1997-09-11 | 2000-11-14 | The Nutrasweet Company | Metal complexes of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester |
US6180156B1 (en) | 1997-09-11 | 2001-01-30 | The Nutrasweet Company | Acid salts of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester |
US6129942A (en) * | 1997-09-11 | 2000-10-10 | The Nutrasweet Company | Sweetener salts of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester |
US6291004B1 (en) | 1997-09-11 | 2001-09-18 | The Nutrasweet Company | Basic salts of n-[n-(3,3-dimethylbutyl)-l-α-aspartyl]-l-phenylalanine 1-methyl ester |
JPH1180108A (ja) * | 1997-09-12 | 1999-03-26 | Ajinomoto Co Inc | 甘味料の精製法 |
JPH11130794A (ja) | 1997-10-23 | 1999-05-18 | Ajinomoto Co Inc | アスパルテーム誘導体の精製方法 |
JPH11171895A (ja) * | 1997-12-11 | 1999-06-29 | Ajinomoto Co Inc | アスパルテームとアスパルテーム誘導体の分離精製方法 |
JPH11169132A (ja) * | 1997-12-15 | 1999-06-29 | Ajinomoto Co Inc | アスパルテームとアスパルテーム誘導体の混晶及びその製造方法 |
US6692778B2 (en) * | 1998-06-05 | 2004-02-17 | Wm. Wrigley Jr. Company | Method of controlling release of N-substituted derivatives of aspartame in chewing gum |
WO1999062354A1 (en) * | 1998-06-05 | 1999-12-09 | Wm. Wrigley Jr. Company | Method of controlling release of n-substituted derivatives of aspartame in chewing gum and gum produced thereby |
US5977415A (en) * | 1998-08-20 | 1999-11-02 | The Nutrasweet Company | Preparation of 3, 3-dimethylbutyraldehyde from a tert-butyl cation precursor, vinyl chloride and an acidic catalyst |
NL1010063C2 (nl) * | 1998-09-10 | 2000-03-13 | Holland Sweetener Co | Werkwijze voor de bereiding van neotaam. |
US6214402B1 (en) | 1998-09-17 | 2001-04-10 | The Nutrasweet Company | Co-crystallization of sugar and n-[n-(3,3-dimethylbutyl)-l αaspartyl]-l-phenylalanine 1-methyl ester |
US5994593A (en) * | 1998-09-17 | 1999-11-30 | The Nutrasweet Company | Synthesis and purification of 3,3-dimethylbutyraldehyde via hydrolysis of 1,1-dichloro-3,3-dimethylbutane or 1-bromo-1-chloro-3,3-dimethylbutane |
US6844465B2 (en) * | 1998-10-30 | 2005-01-18 | Ajinomoto Co., Inc. | Method for preparing highly stable crystals of aspartame derivative |
CN1317012A (zh) | 1998-10-30 | 2001-10-10 | 味之素株式会社 | 稳定性优良的天冬甜素衍生物晶体的结晶方法 |
US6465677B1 (en) | 1998-11-19 | 2002-10-15 | The Nutrasweet Company | Method for the preparation of N-neohexyl-α-aspartyl-L-phenylalanine methyl ester from imidazolidin-4-one intermediates |
WO2000031118A1 (en) * | 1998-11-20 | 2000-06-02 | The Nutrasweet Company | AMORPHOUS N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER |
AU1832500A (en) * | 1998-11-25 | 2000-06-19 | Nutrasweet Company, The | Purification of N-(N-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methyl ester via crystallization |
WO2000036933A1 (en) * | 1998-12-18 | 2000-06-29 | The Nutrasweet Company | USE OF N-NEOHEXYL-α-ASPARTYL-L-PHENYLALANINE METHYL ESTER AS A FLAVOR MODIFIER |
US6077962A (en) * | 1998-12-24 | 2000-06-20 | The Nutrasweet Company | N-3, 3-dimethylbutyl-L-aspartic acid and esters thereof, the process of preparing the same, and the process for preparing N-(N-(3,3-dimethylbutyl) -α L-aspartyl)-L- phenylalanine 1-methyl ester therefrom |
US6048999A (en) * | 1999-01-25 | 2000-04-11 | The Nutrasweet Company | N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester synergistic sweetener blends |
US6180157B1 (en) | 1999-02-18 | 2001-01-30 | The Nutrasweet Company | Process for preparing an N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester agglomerate |
AU4449100A (en) * | 1999-03-03 | 2000-09-21 | Nutrasweet Company, The | Novel crystallization products of neotame and methods for producing same |
WO2000057725A1 (en) | 1999-03-26 | 2000-10-05 | The Nutrasweet Company | PARTICLES OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER |
US6573409B1 (en) | 1999-07-02 | 2003-06-03 | The Nutrasweet Company | Process for the preparation of 3,3-dimethylbutanal |
AU4459400A (en) * | 1999-07-28 | 2001-02-19 | Nutrasweet Company, The | A method for the purification of n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl]-l-phenylalanine 1-methyl ester |
US6506434B1 (en) | 1999-08-06 | 2003-01-14 | The Nutrasweet Company | Process for coating N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester onto a carrier |
KR20020038795A (ko) * | 1999-10-07 | 2002-05-23 | 에가시라 구니오 | 아스파르틸디펩타이드 에스테르 유도체의 제조방법과 이를위한 신규한 제조 중간체 및 이의 제조방법 |
US20040176472A1 (en) * | 1999-10-07 | 2004-09-09 | Ajinomoto Co., Inc. | Process for production of aspartyl dipeptide ester derivative, novel production intermediate therefor, and process for production thereof |
CA2386859A1 (en) * | 1999-10-08 | 2001-04-19 | Ajinomoto Co., Inc. | Process for production of aspartame derivative, crystal thereof, novel production intermediate therefor, and process for production of intermediate thereof |
US6627431B1 (en) * | 2000-05-12 | 2003-09-30 | The Nutrasweet Company | Chemoenzymatic synthesis of neotame |
US6281380B1 (en) * | 2000-05-18 | 2001-08-28 | The Nutra Sweet Company | Synthesis of N-(N-(3,3-dimethylbutyl)-L-α-aspartyl)L-phenylalanine1-methyl ester by reductive alkylation and crystallization/ isolation in aqueous methanol |
DE60115106T2 (de) | 2000-05-18 | 2006-07-13 | The Nutrasweet Co., Chicago | Herstellung von N-[N-(3,3-Dimethylbutyl)-l-Alpha-Aspartyl]-l-Phenylalanin-1-Methylester durch Verwendung vom l-Alpha-Aspartyl-l-Phenylalanin-1-Methylester als Vorläufer |
ATE288446T1 (de) | 2000-05-19 | 2005-02-15 | Nutrasweet Co | Herstellung von n-(n-(3,3-dimethylbutyl)-l-alpha- aspartyl)- l-phenylalaninmethylester mittels oxazolidinonderivate |
US7326430B2 (en) * | 2000-07-18 | 2008-02-05 | The Nutrasweet Company | Method of preparing liquid compositions for delivery of N-[N- (3,3-dimethylbutyl-L-α-aspartyl]-L-phenylalanine 1-methyl ester in food and beverage systems |
US6225493B1 (en) * | 2000-08-21 | 2001-05-01 | The Nutrasweet Company | Metal ion assisted N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester isomer resolution |
AU2001297682A1 (en) * | 2000-11-06 | 2002-09-04 | The Nutrasweet Company | Catalyst modification to enhance neotame production |
US6720446B2 (en) * | 2001-11-05 | 2004-04-13 | The Nutrasweet Company | Catalyst modification to enhance neotame production |
US6782048B2 (en) * | 2002-06-21 | 2004-08-24 | Pulse-Link, Inc. | Ultra-wideband communication through a wired network |
WO2004101604A2 (en) * | 2003-05-06 | 2004-11-25 | Nutrasweet Company | SYNTHESIS OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER USING 3,3-DIMETHYLBUTYRALDEHYDE PRECURSORS |
WO2005087020A1 (en) * | 2004-03-05 | 2005-09-22 | Richmond Chemical Corporation | High-intensity sweetener-polyol compositions |
US20060188629A1 (en) * | 2005-01-21 | 2006-08-24 | Greg Liesen | Method for the purification of sucralose |
CN101270092B (zh) * | 2008-04-30 | 2010-12-08 | 厦门大学 | 一种合成纽甜的方法 |
FR3102041A1 (fr) | 2019-10-22 | 2021-04-23 | Aroma Sens | Edulcorant pour liquides de cigarette électronique |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59227849A (ja) * | 1983-06-08 | 1984-12-21 | Ajinomoto Co Inc | L―α―アスパルチル―L―フェニルアラニンメチルエステル束状晶の晶析分離法 |
FR2697844B1 (fr) * | 1992-11-12 | 1995-01-27 | Claude Nofre | Nouveaux composés dérivés de dipeptides ou d'analogues dipeptidiques utiles comme agents édulcorants, leur procédé de préparation. |
FR2719590B1 (fr) * | 1994-05-09 | 1996-07-26 | Claude Nofre | Procédé perfectionné de préparation d'un composé dérivé de l'aspartame utile comme agent édulcorant. |
US5480688A (en) * | 1994-06-13 | 1996-01-02 | The Auld Company | Shaped flexible decorative articles and method for making same |
US5510805A (en) * | 1994-08-08 | 1996-04-23 | Prime View International Co. | Scanning circuit |
EP0751146B1 (en) * | 1995-06-30 | 2002-03-13 | Holland Sweetener Company V.o.F. | Crystallization of alpha-L-aspartyl-L-phenylalanine methyl ester from aqueous solution |
-
1997
- 1997-01-29 US US08/790,113 patent/US5728862A/en not_active Expired - Lifetime
-
1998
- 1998-01-26 TW TW087101110A patent/TW432074B/zh not_active IP Right Cessation
- 1998-01-29 AU AU61375/98A patent/AU723479B2/en not_active Expired
- 1998-01-29 WO PCT/US1998/001734 patent/WO1998032767A1/en active IP Right Grant
- 1998-01-29 DK DK98906040T patent/DK0973796T3/da active
- 1998-01-29 NZ NZ336893A patent/NZ336893A/en not_active IP Right Cessation
- 1998-01-29 IL IL13114098A patent/IL131140A0/xx not_active IP Right Cessation
- 1998-01-29 EP EP98906040A patent/EP0973796B1/en not_active Expired - Lifetime
- 1998-01-29 EA EA199900690A patent/EA001948B1/ru not_active IP Right Cessation
- 1998-01-29 CA CA002278608A patent/CA2278608C/en not_active Expired - Lifetime
- 1998-01-29 UY UY24864A patent/UY24864A1/es not_active IP Right Cessation
- 1998-01-29 TR TR1999/01811T patent/TR199901811T2/xx unknown
- 1998-01-29 CO CO98004324A patent/CO5040054A1/es unknown
- 1998-01-29 DE DE69832870T patent/DE69832870T2/de not_active Expired - Lifetime
- 1998-01-29 UA UA99084829A patent/UA57605C2/uk unknown
- 1998-01-29 PL PL334882A patent/PL191750B1/pl unknown
- 1998-01-29 BR BRPI9807020-7A patent/BR9807020B1/pt not_active IP Right Cessation
- 1998-01-29 HU HU0001453A patent/HU228676B1/hu unknown
- 1998-01-29 CN CNB988035219A patent/CN1136227C/zh not_active Expired - Lifetime
- 1998-01-29 AR ARP980100388A patent/AR011782A1/es active IP Right Grant
- 1998-01-29 SK SK1010-99A patent/SK285451B6/sk unknown
- 1998-01-29 PE PE1998000066A patent/PE71999A1/es not_active IP Right Cessation
- 1998-01-29 AT AT98906040T patent/ATE313555T1/de active
- 1998-01-29 CZ CZ0261299A patent/CZ296888B6/cs not_active IP Right Cessation
- 1998-01-29 EE EEP199900329A patent/EE03928B1/et unknown
- 1998-01-29 ID IDW990777A patent/ID22966A/id unknown
- 1998-01-29 ES ES98906040T patent/ES2251765T3/es not_active Expired - Lifetime
-
1999
- 1999-07-28 NO NO19993676A patent/NO326212B1/no not_active IP Right Cessation
- 1999-08-27 BG BG103694A patent/BG64562B1/bg unknown
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