CZ287731B6 - Protein selective acylation process - Google Patents
Protein selective acylation process Download PDFInfo
- Publication number
- CZ287731B6 CZ287731B6 CZ19971456A CZ145697A CZ287731B6 CZ 287731 B6 CZ287731 B6 CZ 287731B6 CZ 19971456 A CZ19971456 A CZ 19971456A CZ 145697 A CZ145697 A CZ 145697A CZ 287731 B6 CZ287731 B6 CZ 287731B6
- Authority
- CZ
- Czechia
- Prior art keywords
- insulin
- fatty acid
- amino
- ester
- amino group
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 45
- 230000010933 acylation Effects 0.000 title claims abstract description 34
- 238000005917 acylation reaction Methods 0.000 title claims abstract description 34
- 102000004169 proteins and genes Human genes 0.000 title claims abstract description 21
- 108090000623 proteins and genes Proteins 0.000 title claims abstract description 21
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- 239000011356 non-aqueous organic solvent Substances 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
- 239000002243 precursor Substances 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
- 230000017854 proteolysis Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 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)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Endocrinology (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/341,231 US5646242A (en) | 1994-11-17 | 1994-11-17 | Selective acylation of epsilon-amino groups |
| PCT/US1995/014872 WO1996015803A1 (en) | 1994-11-17 | 1995-11-14 | SELECTIVE ACYLATION OF ε-AMINO GROUPS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ145697A3 CZ145697A3 (en) | 1997-12-17 |
| CZ287731B6 true CZ287731B6 (en) | 2001-01-17 |
Family
ID=23336740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ19971456A CZ287731B6 (en) | 1994-11-17 | 1995-11-14 | Protein selective acylation process |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US5646242A (en, 2012) |
| EP (2) | EP1227107A1 (en, 2012) |
| JP (1) | JP4312828B2 (en, 2012) |
| CN (1) | CN1171742A (en, 2012) |
| AR (1) | AR003915A1 (en, 2012) |
| AT (1) | ATE328902T1 (en, 2012) |
| AU (2) | AU691066B2 (en, 2012) |
| BR (1) | BR9509652A (en, 2012) |
| CA (1) | CA2205061A1 (en, 2012) |
| CO (1) | CO4520285A1 (en, 2012) |
| CZ (1) | CZ287731B6 (en, 2012) |
| DE (1) | DE69535031T2 (en, 2012) |
| DK (1) | DK0712862T3 (en, 2012) |
| ES (1) | ES2264124T3 (en, 2012) |
| HU (2) | HU217585B (en, 2012) |
| IL (1) | IL115972A (en, 2012) |
| IN (1) | IN179820B (en, 2012) |
| NO (1) | NO972185L (en, 2012) |
| NZ (1) | NZ297256A (en, 2012) |
| PL (1) | PL320556A1 (en, 2012) |
| PT (1) | PT712862E (en, 2012) |
| RU (1) | RU2155773C2 (en, 2012) |
| SI (1) | SI0712862T1 (en, 2012) |
| TR (1) | TR199501421A2 (en, 2012) |
| WO (1) | WO1996015803A1 (en, 2012) |
| YU (1) | YU71495A (en, 2012) |
| ZA (1) | ZA959680B (en, 2012) |
Families Citing this family (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE69731105T2 (de) * | 1996-07-11 | 2005-11-17 | Novo Nordisk A/S | Verfahren zur selektiven acetylierung |
| US6444641B1 (en) | 1997-10-24 | 2002-09-03 | Eli Lilly Company | Fatty acid-acylated insulin analogs |
| EA200000453A1 (ru) * | 1997-10-24 | 2000-10-30 | Эли Лилли Энд Компани | Композиции нерастворимого инсулина |
| US5985263A (en) * | 1997-12-19 | 1999-11-16 | Enzon, Inc. | Substantially pure histidine-linked protein polymer conjugates |
| US5981709A (en) * | 1997-12-19 | 1999-11-09 | Enzon, Inc. | α-interferon-polymer-conjugates having enhanced biological activity and methods of preparing the same |
| 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 |
| WO2001085256A2 (en) * | 2000-05-05 | 2001-11-15 | Novo Nordisk A/S | 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 |
| CN1406131A (zh) * | 2000-12-25 | 2003-03-26 | 株式会社资生堂 | 活化交感神经的香料组合物 |
| 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 |
| 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 |
| 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 |
| 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 |
| US6835802B2 (en) * | 2001-06-04 | 2004-12-28 | Nobex Corporation | Methods of synthesizing substantially monodispersed mixtures of polymers having polyethylene glycol moieties |
| US20030082671A1 (en) | 2001-07-24 | 2003-05-01 | Thomas Hoeg-Jensen | Method for making acylated polypeptides |
| JP2005503141A (ja) * | 2001-07-24 | 2005-02-03 | ノボ ノルディスク アクティーゼルスカブ | アシル化ポリペプチドを作出するための方法 |
| DE60229403D1 (de) * | 2001-07-24 | 2008-11-27 | Novo Nordisk As | Verfahren zur herstellung acylierter polypeptide |
| US7595172B2 (en) * | 2001-07-24 | 2009-09-29 | Novo Nordisk A/S | 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 |
| US6770625B2 (en) | 2001-09-07 | 2004-08-03 | Nobex Corporation | Pharmaceutical compositions of calcitonin drug-oligomer conjugates and methods of treating diseases therewith |
| US7196059B2 (en) | 2001-09-07 | 2007-03-27 | Biocon Limited | Pharmaceutical compositions of insulin drug-oligomer conjugates and methods of treating diseases therewith |
| DE60234198D1 (de) | 2001-09-07 | 2009-12-10 | Biocon Ltd | Verfahren zur synthese von insulinpolypeptid-oligomer-konjugaten und proinsulinpolypeptid-oligomer-konjugaten und verfahren zu deren synthese |
| 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 |
| US7030082B2 (en) * | 2001-09-07 | 2006-04-18 | Nobex Corporation | Pharmaceutical compositions of drug-oligomer conjugates and methods of treating disease therewith |
| US7312192B2 (en) * | 2001-09-07 | 2007-12-25 | Biocon Limited | Insulin polypeptide-oligomer conjugates, proinsulin polypeptide-oligomer conjugates and methods of synthesizing same |
| US20030199445A1 (en) * | 2002-02-07 | 2003-10-23 | Knudsen Lotte Bjerre | Use of GLP-1 compound for treatment of critically ill patients |
| AU2003236521A1 (en) | 2002-06-13 | 2003-12-31 | 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 |
| CN100586926C (zh) * | 2002-09-25 | 2010-02-03 | 诺沃娜第克公司 | 制备酰化肽的方法 |
| 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 |
| EP1687428A1 (en) | 2003-11-14 | 2006-08-09 | Novo Nordisk A/S | Processes for making acylated insulin |
| DK1773878T3 (en) | 2004-07-19 | 2015-05-11 | Biocon Ltd | Insulin-oligomerkonjugater, formulations and uses thereof |
| ATE513921T1 (de) | 2005-08-16 | 2011-07-15 | Novo Nordisk As | Verfahren zur herstellung reifer insulinpolypeptide |
| JP4808785B2 (ja) * | 2005-12-28 | 2011-11-02 | ノボ・ノルデイスク・エー／エス | インスリン組成物および組成物の製造方法 |
| JP5202338B2 (ja) * | 2006-02-27 | 2013-06-05 | ノボ・ノルデイスク・エー／エス | 新規インシュリン誘導体 |
| US8927015B2 (en) * | 2006-04-12 | 2015-01-06 | Emisphere Technologies, Inc. | Formulations for delivering insulin |
| CN101573133B (zh) | 2006-07-31 | 2014-08-27 | 诺沃-诺迪斯克有限公司 | Peg化延长的胰岛素 |
| JP5864834B2 (ja) | 2006-09-22 | 2016-02-17 | ノボ・ノルデイスク・エー／エス | プロテアーゼ耐性のインスリンアナログ |
| US8518668B2 (en) | 2006-09-27 | 2013-08-27 | Novo Nordisk A/S | Method for making maturated insulin polypeptides in a fungal cell |
| WO2008132224A2 (en) | 2007-04-30 | 2008-11-06 | Novo Nordisk A/S | Method for drying a protein composition, a dried protein composition and a pharmaceutical composition comprising the dried protein |
| ES2744384T3 (es) | 2007-06-13 | 2020-02-24 | Novo Nordisk As | Formulación farmacéutica que comprende un derivado de insulina |
| AU2008313248B2 (en) | 2007-10-16 | 2012-04-26 | Biocon Limited | An orally administerable solid pharmaceutical composition and a process thereof |
| JP5762001B2 (ja) | 2008-03-14 | 2015-08-12 | ノボ・ノルデイスク・エー／エス | プロテアーゼ安定化インスリンアナログ |
| PL2910570T3 (pl) | 2008-03-18 | 2017-06-30 | Novo Nordisk A/S | Stabilizowane względem proteaz, acylowane analogi insuliny |
| ES2561208T3 (es) | 2008-09-12 | 2016-02-25 | Novo Nordisk A/S | Método de acilación de un péptido o una proteína |
| JP4959005B2 (ja) * | 2008-10-30 | 2012-06-20 | ノボ・ノルデイスク・エー／エス | 毎日の注射頻度より少ないインスリン注射での真性糖尿病の治療 |
| AU2010216385B2 (en) * | 2009-02-20 | 2013-06-20 | Ipsen Pharma S.A.S. | Analogues of neuropeptide Y having proline substitution at position 34 |
| BR112012012945A2 (pt) | 2009-11-25 | 2020-12-29 | Arisgen Sa | Composição de liberação mucosal, seu método de produção, complexo de peptídeo pré-formado, kit e uso de um agente ativo de peptídeo |
| RU2013123515A (ru) | 2010-10-27 | 2014-12-10 | Ново Нордиск А/С | Лечение сахарного диабета с помощью инъекций инсулина, вводимых с различными интервалами |
| MX2014012096A (es) | 2012-04-11 | 2014-11-21 | Novo Nordisk As | Formulaciones de insulina. |
| EP2991672A1 (en) | 2013-04-30 | 2016-03-09 | Novo Nordisk A/S | Novel administration regime |
| JP6499184B2 (ja) | 2013-10-07 | 2019-04-10 | ノヴォ ノルディスク アー／エス | インスリン類似体の新規な誘導体 |
| 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 |
| EP3452587B1 (en) | 2016-05-05 | 2021-09-08 | Codexis, Inc. | Penicillin-g acylases |
| MA46780A (fr) | 2016-11-07 | 2019-09-11 | Novo Nordisk As | Esters à dchbs actif de composés peg et leur utilisation |
| HUE055231T2 (hu) | 2016-12-16 | 2021-11-29 | Novo Nordisk As | Inzulint tartalmazó gyógyászati készítmények |
| 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 |
| CN114096269B (zh) | 2019-07-12 | 2024-06-11 | 诺和诺德股份有限公司 | 高浓度胰岛素制剂 |
| 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 |
| US3950517A (en) * | 1970-05-08 | 1976-04-13 | National Research Development Corporation | Insulin derivatives |
| 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 |
| GB1381273A (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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| DE2252157C3 (de) * | 1972-10-25 | 1976-03-18 | Hoechst Ag | Zwischenprodukte zur herstellung von insulin, insulin-analogen und -derivaten und verfahren zur herstellung von insulin, insulin analogen und derivaten |
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-
1994
- 1994-11-17 US US08/341,231 patent/US5646242A/en not_active Ceased
-
1995
- 1995-11-14 IN IN1452CA1995 patent/IN179820B/en unknown
- 1995-11-14 CO CO95053590A patent/CO4520285A1/es unknown
- 1995-11-14 PT PT95308167T patent/PT712862E/pt unknown
- 1995-11-14 ES ES95308167T patent/ES2264124T3/es not_active Expired - Lifetime
- 1995-11-14 AU AU42372/96A patent/AU691066B2/en not_active Revoked
- 1995-11-14 EP EP02000258A patent/EP1227107A1/en not_active Ceased
- 1995-11-14 HU HU9800566A patent/HU217585B/hu not_active IP Right Cessation
- 1995-11-14 JP JP51696396A patent/JP4312828B2/ja not_active Expired - Lifetime
- 1995-11-14 HU HU9903007A patent/HU9903007D0/hu unknown
- 1995-11-14 DE DE69535031T patent/DE69535031T2/de not_active Expired - Lifetime
- 1995-11-14 WO PCT/US1995/014872 patent/WO1996015803A1/en not_active Application Discontinuation
- 1995-11-14 NZ NZ297256A patent/NZ297256A/xx active IP Right Revival
- 1995-11-14 CZ CZ19971456A patent/CZ287731B6/cs not_active IP Right Cessation
- 1995-11-14 AR ARP950100165A patent/AR003915A1/es not_active Application Discontinuation
- 1995-11-14 YU YU71495A patent/YU71495A/sh unknown
- 1995-11-14 TR TR95/01421A patent/TR199501421A2/xx unknown
- 1995-11-14 CN CN95197224A patent/CN1171742A/zh active Pending
- 1995-11-14 ZA ZA959680A patent/ZA959680B/xx unknown
- 1995-11-14 PL PL95320556A patent/PL320556A1/xx unknown
- 1995-11-14 AT AT95308167T patent/ATE328902T1/de active
- 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 CA CA002205061A patent/CA2205061A1/en not_active Abandoned
- 1995-11-14 DK DK95308167T patent/DK0712862T3/da active
- 1995-11-14 EP EP95308167A patent/EP0712862B1/en not_active Expired - Lifetime
- 1995-11-14 SI SI9530727T patent/SI0712862T1/sl unknown
- 1995-11-14 IL IL11597295A patent/IL115972A/xx unknown
-
1997
- 1997-05-13 NO NO972185A patent/NO972185L/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
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 19951114 |