ATE229031T1 - 6,7-oxygenierte steroide und deren verwendung - Google Patents
6,7-oxygenierte steroide und deren verwendungInfo
- Publication number
- ATE229031T1 ATE229031T1 AT97929071T AT97929071T ATE229031T1 AT E229031 T1 ATE229031 T1 AT E229031T1 AT 97929071 T AT97929071 T AT 97929071T AT 97929071 T AT97929071 T AT 97929071T AT E229031 T1 ATE229031 T1 AT E229031T1
- Authority
- AT
- Austria
- Prior art keywords
- oxygen substitution
- steroids
- disclosed
- steroid
- functionality
- Prior art date
Links
- 150000003431 steroids Chemical class 0.000 title abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 6
- 239000001301 oxygen Substances 0.000 abstract 6
- 229910052760 oxygen Inorganic materials 0.000 abstract 6
- 238000006467 substitution reaction Methods 0.000 abstract 6
- -1 Steroid compounds Chemical class 0.000 abstract 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical group C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000422 delta-lactone group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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
-
- 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
- C07J1/0003—Androstane derivatives
- C07J1/0007—Androstane derivatives not substituted in position 17
-
- 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
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- 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
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/005—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not 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
- C07J21/005—Ketals
- C07J21/008—Ketals at position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
-
- 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
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C07J41/0016—Oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
-
- 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
-
- 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
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2345096P | 1996-07-11 | 1996-07-11 | |
| US67964296A | 1996-07-12 | 1996-07-12 | |
| PCT/CA1997/000490 WO1998002450A2 (en) | 1996-07-11 | 1997-07-11 | 6,7-oxygenated steroids and uses related thereto |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE229031T1 true ATE229031T1 (de) | 2002-12-15 |
Family
ID=26697171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT97929071T ATE229031T1 (de) | 1996-07-11 | 1997-07-11 | 6,7-oxygenierte steroide und deren verwendung |
Country Status (13)
| Country | Link |
|---|---|
| US (5) | US6046185A (de) |
| EP (1) | EP0917534B1 (de) |
| JP (1) | JP2001503732A (de) |
| KR (1) | KR100533436B1 (de) |
| AT (1) | ATE229031T1 (de) |
| AU (1) | AU722815B2 (de) |
| BR (1) | BR9710353A (de) |
| CA (1) | CA2259981C (de) |
| DE (1) | DE69717633T2 (de) |
| ES (1) | ES2187788T3 (de) |
| NZ (1) | NZ333731A (de) |
| RU (1) | RU2196143C2 (de) |
| WO (1) | WO1998002450A2 (de) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002506830A (ja) | 1998-03-13 | 2002-03-05 | ザ ユニバーシティ オブ ブリティッシュ コロンビア | 治療的ケモカイン受容体アンタゴニスト |
| CA2305787A1 (en) * | 2000-05-09 | 2001-11-09 | The University Of British Columbia | Cxcr4 antagonist treatment of hematopoietic cells |
| CA2245224A1 (en) * | 1998-08-14 | 2000-02-14 | Jiang-Hong Giong | Chemokine receptor antagonists and chemotherapeutics |
| US20080015174A1 (en) * | 1998-11-24 | 2008-01-17 | Reading Christopher L | Metabolic Disease Treatments |
| US20030083231A1 (en) * | 1998-11-24 | 2003-05-01 | Ahlem Clarence N. | Blood cell deficiency treatment method |
| US6667299B1 (en) * | 2000-03-16 | 2003-12-23 | Hollis-Eden Pharmaceuticals, Inc. | Pharmaceutical compositions and treatment methods |
| US7378098B2 (en) * | 2000-04-12 | 2008-05-27 | The University Of British Columbia | CXC chemokine receptor 4 agonist peptides |
| US7368425B2 (en) * | 2006-03-24 | 2008-05-06 | Chemokine Therapeutics Corp. | Cyclic peptides for modulating growth of neo-vessels and their use in therapeutic angiogenesis |
| US20050059584A1 (en) * | 2002-08-16 | 2005-03-17 | Ahmed Merzouk | Novel chemokine mimetics synthesis and their use |
| CA2335109A1 (en) * | 2000-04-12 | 2001-10-12 | Chemokine Therapeutics Corporation | Cxcr4 agonist treatment of hematopoietic cells |
| EP1278763B1 (de) * | 2000-04-28 | 2007-02-14 | Inflazyme Pharmaceuticals, Ltd. | 3-stickstoff-6,7-dioxygenierte steroid verbindungen und verwendungen davon |
| US7067148B2 (en) | 2001-02-15 | 2006-06-27 | King Pharmaceutical Research & Development, Inc. | Stabilized pharmaceutical and thyroid hormone compositions and method of preparation |
| EP1392322A1 (de) * | 2001-05-21 | 2004-03-03 | Alcon, Inc. | Methode zur behandlung des trockenen auges |
| JP2004527578A (ja) | 2001-05-21 | 2004-09-09 | アルコン，インコーポレイテッド | ドライアイ障害を処置するためのＮＦ−κＢインヒビターの使用 |
| EP1404700A2 (de) * | 2001-05-22 | 2004-04-07 | Inflazyme Pharmaceuticals, Ltd. | Verfahren zur herstellung von 6,7-dihydroxy steroidverbindungen durch allylisch-oxidation von steroid-5-en verbindungen zu entsprechenden steroid-5-en-7-on verbindungen und hydroboration und oxidation, sowie zwischenprodukte dieses verfahrens |
| US7101569B2 (en) | 2001-08-14 | 2006-09-05 | Franz G Andrew | Methods of administering levothyroxine pharmaceutical compositions |
| KR20100093621A (ko) * | 2002-03-27 | 2010-08-25 | 파이토팜 피엘씨 | 사포게닌 및 그 유도체의 치료 방법 및 용도 |
| GB0217930D0 (en) * | 2002-08-02 | 2002-09-11 | Glycologic Ltd | A chemical carrier |
| CA2522784C (en) * | 2003-04-01 | 2012-06-19 | Hollis-Eden Pharmaceuticals, Inc. | Antiandrogens with marginal agonist activity and methods of use |
| DE602004031410D1 (de) * | 2003-04-15 | 2011-03-31 | Aquinox Pharmaceuticals Inc | Inden derivate als pharmazeutika |
| EP2471536A1 (de) * | 2004-09-29 | 2012-07-04 | Harbor BioSciences, Inc. | Steroidanaloga sowie charakterisierungs- und behandlungsverfahren |
| AU2006218875B2 (en) * | 2005-02-25 | 2012-08-09 | Efficas, Inc. | Compositions comprising Actinidia and methods of use thereof |
| CN101395159A (zh) | 2006-03-02 | 2009-03-25 | 马林克罗特公司 | 制备含有低含量α,β-不饱和酮化合物的吗啡烷-6-酮产物的方法 |
| CN101884638B (zh) * | 2010-07-09 | 2011-11-09 | 中山大学 | 5α-雄甾(烷)-3β,5,6β-三醇在制备神经元保护药物中的应用 |
| CN103626819B (zh) * | 2012-03-08 | 2016-01-20 | 广州市赛普特医药科技有限公司 | 雄甾-3β,5α,6β-三醇的晶型化合物及其制备方法 |
| ES2740779T3 (es) | 2013-03-14 | 2020-02-06 | Aquinox Pharmaceuticals Canada Inc | Moduladores de SHIP1 |
| JP6407950B2 (ja) | 2013-03-14 | 2018-10-17 | アクイノックス ファーマシューティカルズ （カナダ） インコーポレイテッド | Ｓｈｉｐ１モジュレーターおよびそれに関連する組成物および方法 |
| CN104072564B (zh) * | 2013-03-28 | 2016-08-17 | 广州市赛普特医药科技股份有限公司 | 2β,3α,5α-三羟基-雄甾-6-酮及其制备方法与用途 |
| CA2986790A1 (en) | 2015-06-26 | 2016-12-29 | Aquinox Pharmaceuticals (Canada) Inc. | Crystalline solid forms of the acetate salt of (1s,3s,4r)-4-((3as,4r,5s,7as)-4-(aminomethyl)-7a-methyl-1-methyleneoctahydro-1h-inden-5-yl)-3-(hydroxymethyl)-4-methylcyclohexanol |
| US10053415B2 (en) | 2016-01-20 | 2018-08-21 | Aquinox Pharmaceuticals (Canada) Inc. | Synthesis of a substituted indene derivative |
| WO2017149052A1 (en) | 2016-03-02 | 2017-09-08 | Patheon Austria Gmbh Co. & Kg | Process and intermediates for the production of 17(20)-ene b-seco steroids |
| JP6892278B2 (ja) * | 2017-02-10 | 2021-06-23 | あすか製薬株式会社 | １５−オキソステロイド化合物及びその製造方法 |
| ES2960542T3 (es) * | 2018-04-06 | 2024-03-05 | Taro Pharmaceuticals Inc | Derivados de hexadecahidro-1H-ciclopenta[a]fenantreno útiles en el tratamiento del dolor y la inflamación |
| JP2021526546A (ja) | 2018-04-06 | 2021-10-07 | アキノックス ファーマシューティカルス（カナダ）インク． | 疼痛及び炎症を治療するのに有用なインデン誘導体 |
| JP2021526545A (ja) | 2018-04-06 | 2021-10-07 | アキノックス ファーマシューティカルス（カナダ）インク． | 疼痛及び炎症を治療するのに有用なインデン誘導体 |
| US20250296952A1 (en) * | 2022-05-06 | 2025-09-25 | Aurisco Pharmaceutical Co., Ltd. | Method for preparing abiraterone acetate and intermediate thereof |
| CN116574151B (zh) * | 2023-03-13 | 2026-03-13 | 奥锐特药业股份有限公司 | 一种醋酸阿比特龙及其中间体的制备方法 |
| CN116178475B (zh) * | 2023-03-13 | 2025-07-29 | 奥锐特药业股份有限公司 | 一种醋酸阿比特龙及其中间体的制备方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3026320A (en) * | 1958-11-28 | 1962-03-20 | Syntex Sa | Derivatives of cortisone and hydrocortisone |
| JPS4122178Y1 (de) * | 1964-12-16 | 1966-11-04 | ||
| US3681410A (en) * | 1970-08-07 | 1972-08-01 | Syntex Corp | Process for preparing 17{60 -hydroxy-20-keto and 17{60 ,21-dihydroxy-20-keto pregnanes and derivatives and intermediates thereof |
| BE792321A (fr) * | 1971-12-08 | 1973-06-05 | Roussel Uclaf | Nouveaux 18,19-dinor 13,beta-alcoyl pregna 4,9,11-trienes et procede depreparation |
| ES427522A1 (es) * | 1973-06-25 | 1976-12-16 | Scherico Ltd | Un procedimiento para la preparacion de un 3-ceto-6-arido-4.6-bis-deshidroesteroide. |
| CH606090A5 (de) * | 1974-07-30 | 1978-10-13 | Ciba Geigy Ag | |
| GB1490852A (en) * | 1974-09-12 | 1977-11-02 | Leo Pharm Prod Ltd | Fusidic acid derivatives |
| US5002961A (en) * | 1987-10-19 | 1991-03-26 | Merrell Dow Pharmaceuticals | Method for reducing injury with imidazol-2-thionecarboxamides |
| US5017573A (en) * | 1988-07-29 | 1991-05-21 | Dainippon Pharmaceutical Co., Ltd. | Indazole-3-carboxylic acid derivatives |
| DK603988D0 (da) * | 1988-10-28 | 1988-10-28 | Klaus Bendtzen | Farmaceutisk praeparat |
| DE4005516A1 (de) * | 1989-02-24 | 1990-08-30 | Henkel Corp | Verfahren zur umwandlung (alpha)-acetyl-substituierter lactone in (alpha)-alkyliden-substituierte lactone |
| US5079239A (en) * | 1990-02-16 | 1992-01-07 | Harbor Branch Oceanographic Institution, Inc. | Sterol disulfates and methods of use |
| US5219879A (en) * | 1990-03-05 | 1993-06-15 | Du Pont Merck Pharmaceutical Company | Heterocyclic steroid compounds |
| GB9212511D0 (en) * | 1992-06-12 | 1992-07-22 | Cortecs Ltd | Pharmaceutical compositions |
| FR2696934B1 (fr) * | 1992-10-20 | 1995-06-02 | Conservatoire Nal Arts Metiers | Dérivés de stéroïdes naturels 3B hydroxyles ayant des propriétés de déclenchement et de stimulation de l'immunité, composition les contenant et procédé pour les obtenir. |
| CA2086221C (en) * | 1992-12-23 | 2003-07-15 | Raymond J. Andersen | Contignasterol, and related 3-alpha hydroxy-6-alpha hydroxy-7-beta hydroxy-15-keto-14-beta steroids useful as anti-inflammatory and anti-thrombosis agent |
| US5506221A (en) * | 1992-12-24 | 1996-04-09 | University Of British Columbia | Contignasterol, and related 3-alpha hydroxy-6-alpha hydroxy-7-beta hydroxy-15-keto-14-beta steroids useful as anti-inflammatory and anti-thrombosis agents |
| US5763435A (en) * | 1995-11-21 | 1998-06-09 | Children's Hospital Medical Center | Sulfate conjugates of ursodeoxycholic acid, and their beneficial use in inflammatory disorders |
-
1997
- 1997-07-10 US US08/893,575 patent/US6046185A/en not_active Expired - Fee Related
- 1997-07-11 ES ES97929071T patent/ES2187788T3/es not_active Expired - Lifetime
- 1997-07-11 DE DE69717633T patent/DE69717633T2/de not_active Expired - Fee Related
- 1997-07-11 AT AT97929071T patent/ATE229031T1/de not_active IP Right Cessation
- 1997-07-11 EP EP97929071A patent/EP0917534B1/de not_active Expired - Lifetime
- 1997-07-11 RU RU99103025/04A patent/RU2196143C2/ru not_active IP Right Cessation
- 1997-07-11 CA CA002259981A patent/CA2259981C/en not_active Expired - Fee Related
- 1997-07-11 KR KR1019997000116A patent/KR100533436B1/ko not_active Expired - Fee Related
- 1997-07-11 BR BR9710353-5A patent/BR9710353A/pt not_active Application Discontinuation
- 1997-07-11 JP JP53564497A patent/JP2001503732A/ja not_active Ceased
- 1997-07-11 NZ NZ333731A patent/NZ333731A/xx unknown
- 1997-07-11 AU AU33323/97A patent/AU722815B2/en not_active Ceased
- 1997-07-11 WO PCT/CA1997/000490 patent/WO1998002450A2/en not_active Ceased
-
1999
- 1999-12-23 US US09/471,827 patent/US6706701B1/en not_active Expired - Fee Related
-
2003
- 2003-11-06 US US10/703,155 patent/US7067682B2/en not_active Expired - Fee Related
- 2003-11-06 US US10/703,153 patent/US6949533B2/en not_active Expired - Fee Related
-
2005
- 2005-11-22 US US11/285,779 patent/US20060211857A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| RU2196143C2 (ru) | 2003-01-10 |
| NZ333731A (en) | 2000-09-29 |
| CA2259981A1 (en) | 1998-01-22 |
| KR100533436B1 (ko) | 2006-01-09 |
| ES2187788T3 (es) | 2003-06-16 |
| EP0917534B1 (de) | 2002-12-04 |
| US20040157814A1 (en) | 2004-08-12 |
| US20060211857A1 (en) | 2006-09-21 |
| US7067682B2 (en) | 2006-06-27 |
| JP2001503732A (ja) | 2001-03-21 |
| US20040162425A1 (en) | 2004-08-19 |
| DE69717633T2 (de) | 2003-10-02 |
| DE69717633D1 (de) | 2003-01-16 |
| WO1998002450A2 (en) | 1998-01-22 |
| BR9710353A (pt) | 2000-01-11 |
| US6706701B1 (en) | 2004-03-16 |
| EP0917534A2 (de) | 1999-05-26 |
| AU3332397A (en) | 1998-02-09 |
| AU722815B2 (en) | 2000-08-10 |
| US6949533B2 (en) | 2005-09-27 |
| CA2259981C (en) | 2008-06-10 |
| US6046185A (en) | 2000-04-04 |
| KR20000023661A (ko) | 2000-04-25 |
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