ATE375992T1 - Epoxidierungsverfahren - Google Patents
EpoxidierungsverfahrenInfo
- Publication number
- ATE375992T1 ATE375992T1 AT01111209T AT01111209T ATE375992T1 AT E375992 T1 ATE375992 T1 AT E375992T1 AT 01111209 T AT01111209 T AT 01111209T AT 01111209 T AT01111209 T AT 01111209T AT E375992 T1 ATE375992 T1 AT E375992T1
- Authority
- AT
- Austria
- Prior art keywords
- group
- hydroxyalkyl
- alkoxyalkyl
- aryloxy
- halo
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000006735 epoxidation reaction Methods 0.000 title 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 3
- 125000004104 aryloxy group Chemical group 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000005041 acyloxyalkyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002837 carbocyclic group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- JUKPWJGBANNWMW-VWBFHTRKSA-N eplerenone Chemical compound C([C@@H]1[C@]2(C)C[C@H]3O[C@]33[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)C(=O)OC)C[C@@]21CCC(=O)O1 JUKPWJGBANNWMW-VWBFHTRKSA-N 0.000 abstract 1
- 229960001208 eplerenone Drugs 0.000 abstract 1
- -1 hydroxycarbonylalkyl Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
- C12P33/06—Hydroxylating
- C12P33/08—Hydroxylating at 11 position
- C12P33/10—Hydroxylating at 11 position at 11 alpha-position
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
- C07J71/0015—Oxiranes at position 9(11)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
- C12P33/005—Degradation of the lateral chains at position 17
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Inorganic Chemistry (AREA)
- Toxicology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Epoxy Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3331596P | 1996-12-11 | 1996-12-11 | |
| US4938897P | 1997-06-11 | 1997-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE375992T1 true ATE375992T1 (de) | 2007-11-15 |
Family
ID=26709541
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT97954126T ATE225367T1 (de) | 1996-12-11 | 1997-12-11 | Verfahren zur herstellung von 3-keto-7alpha- alkoxycarbonyl- delta4,5-steroiden sowie zwischenprodukte |
| AT01111209T ATE375992T1 (de) | 1996-12-11 | 1997-12-11 | Epoxidierungsverfahren |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT97954126T ATE225367T1 (de) | 1996-12-11 | 1997-12-11 | Verfahren zur herstellung von 3-keto-7alpha- alkoxycarbonyl- delta4,5-steroiden sowie zwischenprodukte |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6610844B2 (de) |
| EP (1) | EP0944644B1 (de) |
| JP (1) | JP2001509792A (de) |
| KR (1) | KR100523409B1 (de) |
| CN (1) | CN100369927C (de) |
| AT (2) | ATE225367T1 (de) |
| AU (1) | AU733559B2 (de) |
| BR (1) | BR9714510A (de) |
| CA (1) | CA2273343C (de) |
| DE (2) | DE69716116T2 (de) |
| DK (1) | DK0944644T3 (de) |
| ES (2) | ES2186017T3 (de) |
| HK (1) | HK1043370B (de) |
| IL (1) | IL130182A0 (de) |
| NO (1) | NO314149B1 (de) |
| NZ (1) | NZ336004A (de) |
| PL (1) | PL189459B1 (de) |
| PT (1) | PT944644E (de) |
| RO (1) | RO120710B1 (de) |
| RU (1) | RU2005121439A (de) |
| WO (1) | WO1998025948A2 (de) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA74141C2 (uk) | 1998-12-09 | 2005-11-15 | Дж.Д. Сірл Енд Ко. | Фармацевтична композиція на основі тонкоподрібненого еплеренону (варіанти), спосіб її одержання та спосіб лікування розладів, опосередкованих альдостероном (варіанти) |
| EP1580193A3 (de) * | 1999-12-08 | 2010-06-23 | Pharmacia Corporation | Kristalline Form von Eplerenon |
| JP2003516414A (ja) * | 1999-12-08 | 2003-05-13 | ファルマシア コーポレイション | より高い溶解速度を示すエプレレノン結晶形 |
| CA2362845A1 (en) * | 1999-12-08 | 2001-06-14 | Pharmacia Corporation | Eplerenone crystalline form |
| EP1505072A3 (de) * | 1999-12-08 | 2006-06-21 | Pharmacia Corporation | Kristalline Form von Eplerenon mit verbesserter Lösegeschwindigkeit |
| US6716829B2 (en) | 2000-07-27 | 2004-04-06 | Pharmacia Corporation | Aldosterone antagonist and cyclooxygenase-2 inhibitor combination therapy to prevent or treat inflammation-related cardiovascular disorders |
| AU2001285318A1 (en) * | 2000-08-28 | 2002-03-13 | Pharmacia Corporation | Use of an aldosterone receptor antagonist to improve cognitive function |
| CA2427615A1 (en) | 2000-10-30 | 2002-06-13 | Pharmacia Corporation | Aspergillus ochraceus 11 alpha hydroxylase and oxidoreductase |
| DK1487859T3 (da) * | 2002-03-22 | 2008-10-06 | Pharmacia & Upjohn Co Llc | Fremstillingsmetoder til at fremstille Eplerenon |
| US7235655B2 (en) | 2002-03-22 | 2007-06-26 | Pharmacia & Upjohn Company | Processes to prepare eplerenone |
| TW200407150A (en) | 2002-11-06 | 2004-05-16 | Upjohn Co | Processes for preparing 7- carboxy substituted steroids |
| WO2004043986A1 (en) * | 2002-11-07 | 2004-05-27 | Pharmacia & Upjohn Company Llc | Processes for preparing c-7 substituted 5-androstenes |
| CL2004000574A1 (es) * | 2003-03-21 | 2005-02-11 | Pharmacia Corp Sa Organizada B | Proceso para preparar un compuesto 17-espirolactona o la sal de lactona abierta por carbonilacion del correspondiente 17-alquenil o alquinil derivado, los intermediarios que se usan y su proceso de obtencion. |
| EP1626980A4 (de) * | 2003-05-29 | 2007-07-04 | Univ Washington | Neuroaktive 13,24-cyclo-18,21-dinorcholane und strukturell verwandte pentacyclische steroide |
| KR20060123647A (ko) * | 2004-03-22 | 2006-12-01 | 파마시아 앤드 업존 캄파니 엘엘씨 | 9,11 에폭시 스테로이드의 개선된 제조 방법 |
| US8015725B2 (en) * | 2004-09-21 | 2011-09-13 | Dos-I Solutions, S.L. | Method and machine for the sintering and/or drying of powder materials using infrared radiation |
| CA2525205C (en) * | 2004-11-08 | 2013-06-25 | Ecolab Inc. | Foam cleaning and brightening composition, and methods |
| HUP0402466A2 (en) * | 2004-11-30 | 2006-07-28 | Richter Gedeon Vegyeszet | Industrial process for preparing 17-hydroxy-6-betha, 7-betha, 15-betha, 16-betha-bis-methylene-3-oxo-17-alpha-pregn-4-ene-21-carboxylic acid gamma lacton and the main, intermediates of the process |
| CN1321128C (zh) * | 2005-07-15 | 2007-06-13 | 浙江医药股份有限公司新昌制药厂 | 孕甾－4－烯－7，21－二甲酸，9，11－环氧－17－羟基－3－氧代，γ－内酯，甲酯，(7α,11α,17α)－的制备方法 |
| US8222237B2 (en) * | 2008-11-25 | 2012-07-17 | Evestra, Inc. | Progestational 3-(6,6-ethylene-17B-hydroxy-3-oxo-17A-pregna-4-ene-17A-yl)propionic acid G-lactones |
| US8957052B2 (en) | 2010-05-10 | 2015-02-17 | Universite Paris Descartes | Methods and compositions for the treatment of fluid accumulation in and/or under the retina |
| WO2011157798A1 (en) | 2010-06-16 | 2011-12-22 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and compositions for stimulating reepithelialisation during wound healing |
| CN104844681B (zh) * | 2014-02-13 | 2016-06-01 | 合肥久诺医药科技有限公司 | 一种l晶型依普利酮的精制方法 |
| US9562068B2 (en) | 2014-10-17 | 2017-02-07 | Industriale Chimica, S.R.L. | Process for the preparation of 7 α-(methoxycarbonyl)-3-OXO-17alpha-pregn-4,9(11)-dien-21,17-carbolactone, a useful intermediate for the synthesis of molecules with pharmacological activity |
| WO2017055248A1 (en) | 2015-09-28 | 2017-04-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of heart failure |
| JP6835836B2 (ja) | 2015-10-13 | 2021-02-24 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | 脈絡膜血管新生の処置のための方法及び医薬組成物 |
| CN105541960A (zh) * | 2016-02-22 | 2016-05-04 | 浙江仙琚制药股份有限公司 | 17α-羟基-3-氧代-γ-内酯-孕甾-4-烯-（7α，9α）-二羧酸内酯的制备方法 |
| WO2018019843A1 (en) | 2016-07-26 | 2018-02-01 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Antagonist of mineralocorticoid receptor for the treatment of osteoarthritis |
| CN106349326A (zh) * | 2016-07-29 | 2017-01-25 | 北京万全德众医药生物技术有限公司 | 依普利酮杂质a的制备方法 |
| CN107602652A (zh) * | 2017-10-11 | 2018-01-19 | 浙江仙琚制药股份有限公司 | 制备6β‑甲基泼尼松龙的方法 |
| CN108445236B (zh) * | 2018-02-07 | 2021-04-20 | 深圳市新产业生物医学工程股份有限公司 | 甾体类衍生物和其保存液以及其应用 |
| CN110698529A (zh) * | 2019-11-19 | 2020-01-17 | 湖南新合新生物医药有限公司 | 一种依普利酮中间体△9,11烯酯的制备方法 |
| EP4395785A1 (de) | 2021-08-31 | 2024-07-10 | Inserm (Institut National de la Santé et de la Recherche Scientifique) | Verfahren zur behandlung von augenrosacea |
| CN115433252A (zh) * | 2022-08-24 | 2022-12-06 | 浙江亚瑟医药有限公司 | 一种δ9(11)-坎利酮的制备方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3053856A (en) * | 1958-10-29 | 1962-09-11 | Shell Oil Co | Epoxidation of ethylenic compounds with peroxycarboximidic acids |
| US3200113A (en) | 1963-01-09 | 1965-08-10 | Sterling Drug Inc | 7-cyano steroids and derivatives thereof |
| US3300489A (en) | 1964-07-24 | 1967-01-24 | Smith Kline French Lab | Steroidal c-17 spirolactones and processes and intermediates used in the preparation thereof |
| US3413288A (en) | 1965-07-07 | 1968-11-26 | Parke Davis & Co | Process for the production of steroidal c-17 spirolactones |
| US3759791A (en) | 1970-12-10 | 1973-09-18 | Searle & Co | Selective microbiological preparation of androst-4-ene-3,17-dione |
| FR2216273B1 (de) | 1973-02-06 | 1977-07-22 | Roussel Uclaf | |
| DE2404946C3 (de) * | 1973-02-06 | 1978-03-02 | Roussel-Uclaf S.A., Paris | Verfahren zur Herstellung von 7alpha-Acylthio-Steroidspirolactonen |
| DE2443746A1 (de) * | 1973-09-14 | 1975-03-20 | Searle & Co | 4',5-dihydro-7alpha-alkoxycarbonylspiro eckige klammer auf androst-4-en17,2'(3'h)-furan eckige klammer zu -3-one und entsprechende delta hoch 1,4-verbindungen |
| DE2349022A1 (de) | 1973-09-26 | 1975-04-10 | Schering Ag | Neue d-homo-steroide |
| FR2260569B1 (de) | 1974-02-08 | 1978-06-16 | Ugine Kuhlmann | |
| CH631462A5 (de) | 1976-03-05 | 1982-08-13 | Schering Ag | Verfahren zur herstellung von neuen steroiden der androstan- oder oestranreihe. |
| YU41412B (en) | 1978-08-15 | 1987-04-30 | Gist Brocades Nv | Process for obtaining 17 beta-hydroxy -3-dxo-17 alpha-pregn-4-en-21-carboxylic acid |
| US4270994A (en) | 1980-02-20 | 1981-06-02 | G. D. Searle & Co. | Electrochemical dehydrogenation of steroidal Δ3,5 enol ethers under basic conditions to provide steroidal Δ4,6 dienones |
| JPS58179498A (ja) * | 1982-04-13 | 1983-10-20 | Dainippon Ink & Chem Inc | 微生物による１１α−ヒドロキシル化アンドロスタン系化合物の製造方法 |
| FI77669C (fi) * | 1983-04-13 | 1989-04-10 | Ciba Geigy Ag | 20-spiroxaner och analoger, som innehaoller en oeppen ring e, foerfarande foer deras framstaellning samt dessa innehaollande farmaceutiska preparat. |
| EP0123734A1 (de) | 1983-04-29 | 1984-11-07 | Gist-Brocades N.V. | 17-(Isocyano-sulfonylmethylen)-Steroide, 17-(Formamido-sulfonylmethylen)-Steroide und ihre Herstellung |
| US4670551A (en) * | 1984-06-21 | 1987-06-02 | Ciba-Geigy Corporation | Epoxy steroids |
| EP0263569B1 (de) | 1986-10-10 | 1992-12-09 | Roussel-Uclaf | 9-Alpha-Hydroxysteroide, Verfahren zu ihrer Herstellung und Verfahren zur Herstellung der entsprechenden 9(11)-Dehydro-Derivate. |
| US5502222A (en) | 1994-06-01 | 1996-03-26 | Schering Corporation | Process for preparing delta 9,11 and 21-chloro corticosteroids |
| DE69637140T2 (de) * | 1995-12-11 | 2008-04-10 | G.D. Searle Llc, Chicago | Verfahren zur herstellung einer epoxy-verbindung |
-
1997
- 1997-12-11 DK DK97954126T patent/DK0944644T3/da active
- 1997-12-11 KR KR10-2004-7021389A patent/KR100523409B1/ko not_active Expired - Fee Related
- 1997-12-11 BR BR9714510-6A patent/BR9714510A/pt not_active Application Discontinuation
- 1997-12-11 DE DE69716116T patent/DE69716116T2/de not_active Expired - Fee Related
- 1997-12-11 AT AT97954126T patent/ATE225367T1/de not_active IP Right Cessation
- 1997-12-11 DE DE69738225T patent/DE69738225T2/de not_active Expired - Fee Related
- 1997-12-11 AU AU57983/98A patent/AU733559B2/en not_active Ceased
- 1997-12-11 RO RO99-00668A patent/RO120710B1/ro unknown
- 1997-12-11 AT AT01111209T patent/ATE375992T1/de not_active IP Right Cessation
- 1997-12-11 PT PT97954126T patent/PT944644E/pt unknown
- 1997-12-11 CN CNB971817375A patent/CN100369927C/zh not_active Expired - Fee Related
- 1997-12-11 IL IL13018297A patent/IL130182A0/xx not_active IP Right Cessation
- 1997-12-11 JP JP52703298A patent/JP2001509792A/ja not_active Ceased
- 1997-12-11 ES ES97954126T patent/ES2186017T3/es not_active Expired - Lifetime
- 1997-12-11 PL PL97334084A patent/PL189459B1/pl not_active IP Right Cessation
- 1997-12-11 NZ NZ336004A patent/NZ336004A/en unknown
- 1997-12-11 CA CA002273343A patent/CA2273343C/en not_active Expired - Fee Related
- 1997-12-11 ES ES01111209T patent/ES2293944T3/es not_active Expired - Lifetime
- 1997-12-11 EP EP97954126A patent/EP0944644B1/de not_active Expired - Lifetime
- 1997-12-11 WO PCT/US1997/023090 patent/WO1998025948A2/en not_active Ceased
-
1999
- 1999-06-10 NO NO19992825A patent/NO314149B1/no not_active IP Right Cessation
-
2002
- 2002-03-29 US US10/112,355 patent/US6610844B2/en not_active Expired - Fee Related
- 2002-04-24 HK HK02103077.8A patent/HK1043370B/en not_active IP Right Cessation
-
2005
- 2005-07-07 RU RU2005121439/04A patent/RU2005121439A/ru not_active Application Discontinuation
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