JP4312828B2 - ε−アミノ基の選択的アシル化 - Google Patents
ε−アミノ基の選択的アシル化 Download PDFInfo
- Publication number
- JP4312828B2 JP4312828B2 JP51696396A JP51696396A JP4312828B2 JP 4312828 B2 JP4312828 B2 JP 4312828B2 JP 51696396 A JP51696396 A JP 51696396A JP 51696396 A JP51696396 A JP 51696396A JP 4312828 B2 JP4312828 B2 JP 4312828B2
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- JP
- Japan
- Prior art keywords
- insulin
- amino group
- reaction
- solution
- human insulin
- 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
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- 230000010933 acylation Effects 0.000 title claims description 27
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- 238000002955 isolation Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000009145 protein modification Effects 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/62—Insulins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
- C07K1/1072—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups
- C07K1/1077—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/341,231 US5646242A (en) | 1994-11-17 | 1994-11-17 | Selective acylation of epsilon-amino groups |
| US08/341,231 | 1994-11-17 | ||
| PCT/US1995/014872 WO1996015803A1 (en) | 1994-11-17 | 1995-11-14 | SELECTIVE ACYLATION OF ε-AMINO GROUPS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10509176A JPH10509176A (ja) | 1998-09-08 |
| JP4312828B2 true JP4312828B2 (ja) | 2009-08-12 |
Family
ID=23336740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51696396A Expired - Lifetime JP4312828B2 (ja) | 1994-11-17 | 1995-11-14 | ε−アミノ基の選択的アシル化 |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US5646242A (OSRAM) |
| EP (2) | EP1227107A1 (OSRAM) |
| JP (1) | JP4312828B2 (OSRAM) |
| CN (1) | CN1171742A (OSRAM) |
| AR (1) | AR003915A1 (OSRAM) |
| AT (1) | ATE328902T1 (OSRAM) |
| AU (2) | AU691066B2 (OSRAM) |
| BR (1) | BR9509652A (OSRAM) |
| CA (1) | CA2205061A1 (OSRAM) |
| CO (1) | CO4520285A1 (OSRAM) |
| CZ (1) | CZ287731B6 (OSRAM) |
| DE (1) | DE69535031T2 (OSRAM) |
| DK (1) | DK0712862T3 (OSRAM) |
| ES (1) | ES2264124T3 (OSRAM) |
| HU (2) | HU9903007D0 (OSRAM) |
| IL (1) | IL115972A (OSRAM) |
| IN (1) | IN179820B (OSRAM) |
| NO (1) | NO972185D0 (OSRAM) |
| NZ (1) | NZ297256A (OSRAM) |
| PL (1) | PL320556A1 (OSRAM) |
| PT (1) | PT712862E (OSRAM) |
| RU (1) | RU2155773C2 (OSRAM) |
| SI (1) | SI0712862T1 (OSRAM) |
| TR (1) | TR199501421A2 (OSRAM) |
| WO (1) | WO1996015803A1 (OSRAM) |
| YU (1) | YU71495A (OSRAM) |
| ZA (1) | ZA959680B (OSRAM) |
Families Citing this family (76)
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|---|---|---|---|---|
| GB9316895D0 (en) | 1993-08-13 | 1993-09-29 | Guy S And St Thomas Hospitals | Hepatoselective insulin analogues |
| US6869930B1 (en) * | 1993-09-17 | 2005-03-22 | Novo Nordisk A/S | Acylated insulin |
| US5951974A (en) * | 1993-11-10 | 1999-09-14 | Enzon, Inc. | Interferon polymer conjugates |
| US6251856B1 (en) | 1995-03-17 | 2001-06-26 | Novo Nordisk A/S | Insulin derivatives |
| US5631347A (en) * | 1995-06-07 | 1997-05-20 | Eli Lilly And Company | Reducing gelation of a fatty acid-acylated protein |
| US6451970B1 (en) * | 1996-02-21 | 2002-09-17 | Novo Nordisk A/S | Peptide derivatives |
| US5905140A (en) * | 1996-07-11 | 1999-05-18 | Novo Nordisk A/S, Novo Alle | Selective acylation method |
| WO1998002460A1 (en) * | 1996-07-11 | 1998-01-22 | Novo Nordisk A/S | Selective acylation method |
| ID24890A (id) * | 1997-10-24 | 2000-08-31 | Lilly Co Eli | Komposisi-komposisi insulin yang tidak dapat larut |
| US6444641B1 (en) | 1997-10-24 | 2002-09-03 | Eli Lilly Company | Fatty acid-acylated insulin analogs |
| US5981709A (en) * | 1997-12-19 | 1999-11-09 | Enzon, Inc. | α-interferon-polymer-conjugates having enhanced biological activity and methods of preparing the same |
| US5985263A (en) * | 1997-12-19 | 1999-11-16 | Enzon, Inc. | Substantially pure histidine-linked protein polymer conjugates |
| US6451974B1 (en) | 1999-03-17 | 2002-09-17 | Novo Nordisk A/S | Method of acylating peptides and novel acylating agents |
| US7181349B1 (en) | 1999-05-27 | 2007-02-20 | Cecil Yip | Identification of compounds for modulating dimeric receptors |
| US7169889B1 (en) * | 1999-06-19 | 2007-01-30 | Biocon Limited | Insulin prodrugs hydrolyzable in vivo to yield peglylated insulin |
| AU2001254621A1 (en) * | 2000-05-05 | 2001-11-20 | K.U. Leuven R And D | Critical illness neuropathy |
| US7316999B2 (en) | 2000-06-02 | 2008-01-08 | Novo Nordisk A/S | Glucose dependent release of insulin from glucose sensing insulin derivatives |
| US20030054015A1 (en) * | 2000-12-25 | 2003-03-20 | Shinichiro Haze | Sympathetic-activating perfume composition |
| US7060675B2 (en) * | 2001-02-15 | 2006-06-13 | Nobex Corporation | Methods of treating diabetes mellitus |
| US6867183B2 (en) | 2001-02-15 | 2005-03-15 | Nobex Corporation | Pharmaceutical compositions of insulin drug-oligomer conjugates and methods of treating diseases therewith |
| US6835802B2 (en) * | 2001-06-04 | 2004-12-28 | Nobex Corporation | Methods of synthesizing substantially monodispersed mixtures of polymers having polyethylene glycol moieties |
| US6858580B2 (en) * | 2001-06-04 | 2005-02-22 | Nobex Corporation | Mixtures of drug-oligomer conjugates comprising polyalkylene glycol, uses thereof, and methods of making same |
| US6713452B2 (en) | 2001-06-04 | 2004-03-30 | Nobex Corporation | Mixtures of calcitonin drug-oligomer conjugates comprising polyalkylene glycol, uses thereof, and methods of making same |
| US6828305B2 (en) * | 2001-06-04 | 2004-12-07 | Nobex Corporation | Mixtures of growth hormone drug-oligomer conjugates comprising polyalkylene glycol, uses thereof, and methods of making same |
| US7713932B2 (en) | 2001-06-04 | 2010-05-11 | Biocon Limited | Calcitonin drug-oligomer conjugates, and uses thereof |
| US6828297B2 (en) | 2001-06-04 | 2004-12-07 | Nobex Corporation | Mixtures of insulin drug-oligomer conjugates comprising polyalkylene glycol, uses thereof, and methods of making same |
| US20030082671A1 (en) | 2001-07-24 | 2003-05-01 | Thomas Hoeg-Jensen | Method for making acylated polypeptides |
| AU2002355160A1 (en) * | 2001-07-24 | 2003-02-17 | Novo Nordisk A/S | Method for making acylated polypeptides |
| US7595172B2 (en) * | 2001-07-24 | 2009-09-29 | Novo Nordisk A/S | Method for making acylated polypeptides |
| CA2452735A1 (en) * | 2001-07-24 | 2003-02-06 | Ivan Diers | Method for making acylated polypeptides |
| US7166571B2 (en) * | 2001-09-07 | 2007-01-23 | Biocon Limited | Insulin polypeptide-oligomer conjugates, proinsulin polypeptide-oligomer conjugates and methods of synthesizing same |
| DK1430082T3 (da) | 2001-09-07 | 2010-01-18 | Biocon Ltd | Fremgangsmåde til syntese af insulinpolypeptid-oligomer-konjugater og proinsulinpolypeptid-oligomerkonjugater samt fremgangsmåde til syntese deraf |
| US7030082B2 (en) * | 2001-09-07 | 2006-04-18 | Nobex Corporation | Pharmaceutical compositions of drug-oligomer conjugates and methods of treating disease therewith |
| US6770625B2 (en) | 2001-09-07 | 2004-08-03 | Nobex Corporation | Pharmaceutical compositions of calcitonin drug-oligomer conjugates and methods of treating diseases therewith |
| US6913903B2 (en) | 2001-09-07 | 2005-07-05 | Nobex Corporation | Methods of synthesizing insulin polypeptide-oligomer conjugates, and proinsulin polypeptide-oligomer conjugates and methods of synthesizing same |
| US7312192B2 (en) * | 2001-09-07 | 2007-12-25 | Biocon Limited | Insulin polypeptide-oligomer conjugates, proinsulin polypeptide-oligomer conjugates and methods of synthesizing same |
| US7196059B2 (en) | 2001-09-07 | 2007-03-27 | Biocon Limited | Pharmaceutical compositions of insulin drug-oligomer conjugates and methods of treating diseases therewith |
| US20030199445A1 (en) * | 2002-02-07 | 2003-10-23 | Knudsen Lotte Bjerre | Use of GLP-1 compound for treatment of critically ill patients |
| WO2003105768A2 (en) | 2002-06-13 | 2003-12-24 | Nobex Corporation | Methods of reducing hypoglycemic episodes in the treatment of diabetes mellitus |
| US7273921B2 (en) | 2002-09-25 | 2007-09-25 | Novo Nordisk A/S | Method for producing acylated peptides |
| EP1546090B1 (en) * | 2002-09-25 | 2009-06-24 | Novo Nordisk A/S | Method for producing acylated peptides |
| JP4463814B2 (ja) * | 2003-08-05 | 2010-05-19 | ノボ ノルディスク アクティーゼルスカブ | 新規のインスリン誘導体 |
| WO2005047508A1 (en) | 2003-11-14 | 2005-05-26 | Novo Nordisk A/S | Processes for making acylated insulin |
| PL2626368T3 (pl) | 2004-07-19 | 2017-06-30 | Biocon Limited | Koniugaty insulina-oligomer, ich formulacje i zastosowania |
| CN101243190B (zh) | 2005-08-16 | 2015-05-13 | 诺沃-诺迪斯克有限公司 | 制备成熟胰岛素多肽的方法 |
| ATE519780T1 (de) * | 2005-12-28 | 2011-08-15 | Novo Nordisk As | Ein acyliertes insulin und zink enthaltende zusammensetzungen und verfahren zur herstellung dieser zusammensetzungen |
| WO2007096431A1 (en) * | 2006-02-27 | 2007-08-30 | Novo Nordisk A/S | Insulin derivatives |
| US8927015B2 (en) * | 2006-04-12 | 2015-01-06 | Emisphere Technologies, Inc. | Formulations for delivering insulin |
| EP2049149B1 (en) | 2006-07-31 | 2015-04-15 | Novo Nordisk A/S | Pegylated extended insulins |
| DK2074141T3 (en) | 2006-09-22 | 2016-11-28 | Novo Nordisk As | The protease resistant insulin analogues. |
| US8518668B2 (en) | 2006-09-27 | 2013-08-27 | Novo Nordisk A/S | Method for making maturated insulin polypeptides in a fungal cell |
| JP5496082B2 (ja) | 2007-04-30 | 2014-05-21 | ノボ・ノルデイスク・エー／エス | タンパク質組成物を乾燥させる方法、乾燥タンパク質組成物、及び乾燥タンパク質を含有する薬学的組成物 |
| US9034818B2 (en) | 2007-06-13 | 2015-05-19 | Novo Nordisk A/S | Pharmaceutical formulations comprising an insulin derivative |
| ES2664822T3 (es) | 2007-10-16 | 2018-04-23 | Biocon Limited | Una composición farmacéutica sólida administrable por vía oral y un proceso de la misma |
| CN101970477B (zh) | 2008-03-14 | 2014-12-31 | 诺沃-诺迪斯克有限公司 | 蛋白酶稳定的胰岛素类似物 |
| EP2910569B1 (en) | 2008-03-18 | 2016-10-05 | Novo Nordisk A/S | Protease stabilized, acylated insulin analogues |
| WO2010029159A1 (en) | 2008-09-12 | 2010-03-18 | Novo Nordisk A/S | Method of acylating a peptide or protein |
| EP2352513B1 (en) * | 2008-10-30 | 2016-09-14 | Novo Nordisk A/S | Treating diabetes melitus using insulin injections with less than daily injection frequency |
| CA2751673A1 (en) * | 2009-02-20 | 2010-08-26 | Ipsen Pharma S.A.S | Analogues of neuropeptide y having proline substitution at position 34 |
| WO2011064316A2 (en) | 2009-11-25 | 2011-06-03 | Paolo Botti | Mucosal delivery of peptides |
| RU2013123515A (ru) | 2010-10-27 | 2014-12-10 | Ново Нордиск А/С | Лечение сахарного диабета с помощью инъекций инсулина, вводимых с различными интервалами |
| BR112014025132A2 (pt) | 2012-04-11 | 2017-07-11 | Novo Nordisk As | formulações de insulina |
| WO2014177623A1 (en) | 2013-04-30 | 2014-11-06 | Novo Nordisk A/S | Novel administration regime |
| CA2926701A1 (en) | 2013-10-07 | 2015-04-16 | Novo Nordisk A/S | Novel derivative of an insulin analogue |
| FR3013049B1 (fr) | 2013-11-14 | 2015-11-13 | You-Ping Chan | Analogue de l'insuline glargine |
| AR099569A1 (es) | 2014-02-28 | 2016-08-03 | Novo Nordisk As | Derivados de insulina y los usos médicos de estos |
| CN104558097A (zh) * | 2014-05-20 | 2015-04-29 | 广东东阳光药业有限公司 | 肽的酰化方法 |
| CN105111305B (zh) * | 2015-10-10 | 2018-12-14 | 山东阿华生物药业有限公司 | 酰化胰岛素的色谱纯化方法 |
| CN105440125B (zh) * | 2015-11-25 | 2019-09-24 | 华润昂德生物药业有限公司 | 地特胰岛素或其类似物的制备方法 |
| CA3021009A1 (en) * | 2016-05-05 | 2017-11-09 | Codexis, Inc. | Penicillin-g acylases |
| US11787837B2 (en) | 2016-11-07 | 2023-10-17 | Novo Nordisk A/S | DCHBS-active esters of PEG compounds and their use |
| SI3554534T1 (sl) | 2016-12-16 | 2021-09-30 | Novo Nordisk A/S | Farmacevtski sestavki, ki vsebujejo inzulin |
| CN107602437A (zh) * | 2017-08-09 | 2018-01-19 | 上海昂德生物科技有限公司 | 活化酯的制备方法 |
| US10335464B1 (en) | 2018-06-26 | 2019-07-02 | Novo Nordisk A/S | Device for titrating basal insulin |
| US12343383B2 (en) | 2019-07-12 | 2025-07-01 | Novo Nordisk A/S | High concentration insulin formulation |
| CN116874585B (zh) * | 2023-09-06 | 2023-12-15 | 杭州湃肽生化科技有限公司 | 一种地特胰岛素的合成方法 |
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| FR1468831A (fr) * | 1965-10-05 | 1967-02-10 | Roussel Uclaf | Procédé de préparation de nouveaux composés polypeptidiques et produits en résultant |
| DE1902865A1 (de) * | 1968-02-01 | 1969-09-11 | American Home Prod | Substituierte Insulin-Derivate,Verfahren zu ihrer Herstellung und ihre Verwendung in pharmazeutischen Zubereitungen |
| US3591574A (en) * | 1968-05-29 | 1971-07-06 | American Home Prod | Tri-n-phenylglycyl derivatives of insulin |
| US3528960A (en) * | 1968-10-07 | 1970-09-15 | Lilly Co Eli | N-carboxyaroyl insulins |
| US3823125A (en) * | 1969-10-14 | 1974-07-09 | American Home Prod | N-aminoacyl-substituted insulins |
| US3752798A (en) * | 1969-12-02 | 1973-08-14 | G Amird | Tris-na1,nb1,nepsilonb29 - (3-x-3-oxo - 1-y-prop-1-en-1-yl)(ndelta-(4-z-6-r-pyrimidin - 2 - yl) ornithine b22)-insulins and their preparation |
| US3869437A (en) * | 1970-05-08 | 1975-03-04 | Nat Res Dev | Mono-, di, and N{HD A1{B , N{HU B1{B , N{HU B29{B -tri-acylated insulin |
| US3950517A (en) * | 1970-05-08 | 1976-04-13 | National Research Development Corporation | Insulin derivatives |
| GB1381274A (en) * | 1971-01-28 | 1975-01-22 | Nat Res Dev | Insulin derivatives |
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| US3864325A (en) * | 1971-11-18 | 1975-02-04 | Nat Res Dev | (N{HU Al{b , N{HU Bl{b , N{HU B29{B , carbamoyl)-(O{HU A14{B , O{HU B16{B , O{HU B26{B aryl) insulin derivatives |
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| US5905140A (en) | 1996-07-11 | 1999-05-18 | Novo Nordisk A/S, Novo Alle | Selective acylation method |
-
1994
- 1994-11-17 US US08/341,231 patent/US5646242A/en not_active Ceased
-
1995
- 1995-11-14 CA CA002205061A patent/CA2205061A1/en not_active Abandoned
- 1995-11-14 EP EP02000258A patent/EP1227107A1/en not_active Ceased
- 1995-11-14 NZ NZ297256A patent/NZ297256A/xx active IP Right Revival
- 1995-11-14 WO PCT/US1995/014872 patent/WO1996015803A1/en not_active Application Discontinuation
- 1995-11-14 ES ES95308167T patent/ES2264124T3/es not_active Expired - Lifetime
- 1995-11-14 CN CN95197224A patent/CN1171742A/zh active Pending
- 1995-11-14 PL PL95320556A patent/PL320556A1/xx unknown
- 1995-11-14 EP EP95308167A patent/EP0712862B1/en not_active Expired - Lifetime
- 1995-11-14 SI SI9530727T patent/SI0712862T1/sl unknown
- 1995-11-14 JP JP51696396A patent/JP4312828B2/ja not_active Expired - Lifetime
- 1995-11-14 IN IN1452CA1995 patent/IN179820B/en unknown
- 1995-11-14 CO CO95053590A patent/CO4520285A1/es unknown
- 1995-11-14 AU AU42372/96A patent/AU691066B2/en not_active Revoked
- 1995-11-14 HU HU9903007A patent/HU9903007D0/hu unknown
- 1995-11-14 AT AT95308167T patent/ATE328902T1/de active
- 1995-11-14 AR ARP950100165A patent/AR003915A1/es not_active Application Discontinuation
- 1995-11-14 DE DE69535031T patent/DE69535031T2/de not_active Expired - Lifetime
- 1995-11-14 DK DK95308167T patent/DK0712862T3/da active
- 1995-11-14 ZA ZA959680A patent/ZA959680B/xx unknown
- 1995-11-14 RU RU97110075/04A patent/RU2155773C2/ru active
- 1995-11-14 BR BR9509652A patent/BR9509652A/pt not_active Application Discontinuation
- 1995-11-14 HU HU9800566A patent/HU217585B/hu not_active IP Right Cessation
- 1995-11-14 YU YU71495A patent/YU71495A/sh unknown
- 1995-11-14 PT PT95308167T patent/PT712862E/pt unknown
- 1995-11-14 TR TR95/01421A patent/TR199501421A2/xx unknown
- 1995-11-14 CZ CZ19971456A patent/CZ287731B6/cs not_active IP Right Cessation
- 1995-11-14 IL IL11597295A patent/IL115972A/xx unknown
-
1997
- 1997-05-13 NO NO972185A patent/NO972185D0/no not_active Application Discontinuation
-
1998
- 1998-08-07 AU AU78854/98A patent/AU720820B2/en not_active Ceased
-
1999
- 1999-07-08 US US09/351,103 patent/USRE37971E1/en not_active Expired - Lifetime
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