ZA200100525B - Process for the preparation of quinoline derivative and intermediate therefor. - Google Patents
Process for the preparation of quinoline derivative and intermediate therefor. Download PDFInfo
- Publication number
- ZA200100525B ZA200100525B ZA200100525A ZA200100525A ZA200100525B ZA 200100525 B ZA200100525 B ZA 200100525B ZA 200100525 A ZA200100525 A ZA 200100525A ZA 200100525 A ZA200100525 A ZA 200100525A ZA 200100525 B ZA200100525 B ZA 200100525B
- Authority
- ZA
- South Africa
- Prior art keywords
- preparation
- stirred
- hexane
- quinoline derivative
- solvent
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 238000000034 method Methods 0.000 title abstract description 5
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- WULPWIFGZFQFEQ-UHFFFAOYSA-N 3-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]prop-2-enal Chemical compound C1=CC(F)=CC=C1C1=C(C=CC=O)C(C2CC2)=NC2=CC=CC=C12 WULPWIFGZFQFEQ-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- HASGOCLZFTZSTN-UHFFFAOYSA-N cyclohexane;hexane Chemical compound CCCCCC.C1CCCCC1 HASGOCLZFTZSTN-UHFFFAOYSA-N 0.000 claims 1
- KWMBADTWRIGGGG-UHFFFAOYSA-N 2-diethoxyphosphorylacetonitrile Chemical compound CCOP(=O)(CC#N)OCC KWMBADTWRIGGGG-UHFFFAOYSA-N 0.000 abstract description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract description 4
- 150000002825 nitriles Chemical class 0.000 abstract 1
- -1 quinoline compound Chemical class 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 5
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 150000003248 quinolines Chemical class 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- JAHBIRPTCXOGLB-UHFFFAOYSA-N 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde Chemical compound C1=CC(F)=CC=C1C1=C(C=O)C(C2CC2)=NC2=CC=CC=C12 JAHBIRPTCXOGLB-UHFFFAOYSA-N 0.000 description 1
- BFDPBLWCXIOOLM-UHFFFAOYSA-N 3-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]prop-2-enenitrile Chemical compound C1=CC(F)=CC=C1C1=C(C=CC#N)C(C2CC2)=NC2=CC=CC=C12 BFDPBLWCXIOOLM-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20791198 | 1998-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200100525B true ZA200100525B (en) | 2001-08-01 |
Family
ID=16547618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200100525A ZA200100525B (en) | 1998-07-23 | 2001-01-18 | Process for the preparation of quinoline derivative and intermediate therefor. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6335449B1 (cs) |
| EP (1) | EP1099694B1 (cs) |
| JP (1) | JP4281248B2 (cs) |
| KR (1) | KR100529201B1 (cs) |
| CN (1) | CN1107670C (cs) |
| AT (1) | ATE302190T1 (cs) |
| AU (1) | AU746722C (cs) |
| CA (1) | CA2338334C (cs) |
| CZ (1) | CZ299881B6 (cs) |
| DE (1) | DE69926760T2 (cs) |
| DK (1) | DK1099694T3 (cs) |
| ES (1) | ES2247813T3 (cs) |
| IL (2) | IL140924A0 (cs) |
| MX (1) | MXPA01000890A (cs) |
| NO (1) | NO317787B1 (cs) |
| NZ (1) | NZ509401A (cs) |
| PT (1) | PT1099694E (cs) |
| RU (1) | RU2214402C2 (cs) |
| SK (1) | SK285675B6 (cs) |
| WO (1) | WO2000005213A1 (cs) |
| ZA (1) | ZA200100525B (cs) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6630591B2 (en) * | 2000-01-24 | 2003-10-07 | Ube Industries, Ltd. | Process for the preparation of quinolylpropenal |
| JP4496586B2 (ja) * | 2000-01-24 | 2010-07-07 | 日産化学工業株式会社 | キノリルアクリロニトリルの製造法及びその中間体 |
| JP4496584B2 (ja) * | 2000-01-24 | 2010-07-07 | 日産化学工業株式会社 | キノリルプロペナールの製造法 |
| JP4496585B2 (ja) * | 2000-01-24 | 2010-07-07 | 日産化学工業株式会社 | キノリルプロペナールの製造方法 |
| JP4867071B2 (ja) * | 2000-02-21 | 2012-02-01 | 日産化学工業株式会社 | キノリン誘導体の製造方法 |
| CA2400977C (en) * | 2000-02-21 | 2011-03-22 | Kuraray Co., Ltd. | Processes for preparing quinoline derivatives and intermediates thereof |
| ATE401886T1 (de) * | 2000-10-12 | 2008-08-15 | Nissan Chemical Ind Ltd | Wirkstoffe zur vorbeugung und behandlung von komplikationen im zusammenhang mit diabetes |
| US6777552B2 (en) * | 2001-08-16 | 2004-08-17 | Teva Pharmaceutical Industries, Ltd. | Processes for preparing calcium salt forms of statins |
| JP2002155056A (ja) * | 2000-11-17 | 2002-05-28 | Ube Ind Ltd | キノリルアクリロニトリル誘導体の製法 |
| JP4590749B2 (ja) * | 2001-02-14 | 2010-12-01 | 宇部興産株式会社 | キノリンカルボキシアルデヒド誘導体の製法 |
| TWI309644B (cs) * | 2001-02-14 | 2009-05-11 | Nissan Chemical Ind Ltd | |
| WO2004072040A1 (en) | 2003-02-12 | 2004-08-26 | Ciba Specialty Chemicals Holding Inc. | Crystalline forms of pitavastatin calcium |
| US8455640B2 (en) | 2006-05-03 | 2013-06-04 | Msn Laboratories Limited | Process for statins and its pharmaceutically acceptable salts thereof |
| EP2086945B1 (en) | 2006-10-09 | 2016-01-06 | MSN Laboratories Private Limited | Novel process for the preparation of statins and their pharmaceutically acceptable salts thereof |
| EP2387561A4 (en) | 2009-01-19 | 2012-07-25 | Msn Lab Ltd | IMPROVED PROCESS FOR THE PREPARATION OF HIGH-PURITY (3R, 5S) -7-β-CYCLOPROPYL-4- (4-FLUOROPHENYL) QUINOLIN-3-YL-3,5-DIHYDROXY-6 (E) -HEPTENOIC ACID, INCLUDING ITS PHARMACEUTICALLY ACCEPTABLE SALTS |
| WO2011086584A2 (en) | 2010-01-18 | 2011-07-21 | Msn Laboratories Limited | Improved process for the preparation of amide intermediates and their use thereof |
| US20120022102A1 (en) | 2010-01-20 | 2012-01-26 | Cadila Healthcare Limited | Method for preparation of pitavastatin and its pharmaceutical acceptable salts thereof |
| US9034901B2 (en) | 2010-08-25 | 2015-05-19 | Cadila Healthcare Limited | Pitavastatin calcium and process for its preparation |
| CN103508949B (zh) * | 2013-10-22 | 2015-12-09 | 黄河三角洲京博化工研究院有限公司 | 一种（e）-3-[2-环丙基-4-（4-氟-苯基）-3-喹啉基]丙烯醛的合成方法 |
| WO2016005919A1 (en) | 2014-07-09 | 2016-01-14 | Lupin Limited | Polymorphic forms of pitavastatin sodium |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5815836A (ja) * | 1981-07-17 | 1983-01-29 | オリンパス光学工業株式会社 | 内視鏡管路の洗浄装置 |
| US5854259A (en) | 1987-08-20 | 1998-12-29 | Nissan Chemical Industries Ltd. | Quinoline type mevalonolactones |
| JP2569746B2 (ja) | 1987-08-20 | 1997-01-08 | 日産化学工業株式会社 | キノリン系メバロノラクトン類 |
| US5185328A (en) | 1987-08-20 | 1993-02-09 | Nissan Chemical Industries Ltd. | Quinoline type mevalonolactones useful for treating hyperlipidemia, hyperlipoproteinemia or atherosclerosis |
| DE3905908A1 (de) * | 1989-02-25 | 1990-09-06 | Bayer Ag | Substituierte chinoline, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| JP3528186B2 (ja) | 1991-06-24 | 2004-05-17 | 日産化学工業株式会社 | 光学活性キノリンメバロン酸のジアステレオマー塩 |
| JP3130342B2 (ja) | 1991-10-04 | 2001-01-31 | 日産化学工業株式会社 | 動脈硬化性血管内膜肥厚抑制薬 |
| WO1995023125A1 (fr) | 1994-02-25 | 1995-08-31 | Daicel Chemical Industries, Ltd. | Procede de production de compose de mevalonolactone optiquement actif |
-
1999
- 1999-07-22 DK DK99931484T patent/DK1099694T3/da active
- 1999-07-22 PT PT99931484T patent/PT1099694E/pt unknown
- 1999-07-22 US US09/764,994 patent/US6335449B1/en not_active Expired - Lifetime
- 1999-07-22 AU AU47992/99A patent/AU746722C/en not_active Ceased
- 1999-07-22 WO PCT/JP1999/003923 patent/WO2000005213A1/ja active IP Right Grant
- 1999-07-22 RU RU2001105200/04A patent/RU2214402C2/ru not_active IP Right Cessation
- 1999-07-22 SK SK62-2001A patent/SK285675B6/sk not_active IP Right Cessation
- 1999-07-22 CN CN99809003A patent/CN1107670C/zh not_active Expired - Fee Related
- 1999-07-22 MX MXPA01000890A patent/MXPA01000890A/es not_active IP Right Cessation
- 1999-07-22 CA CA002338334A patent/CA2338334C/en not_active Expired - Fee Related
- 1999-07-22 EP EP99931484A patent/EP1099694B1/en not_active Expired - Lifetime
- 1999-07-22 CZ CZ20010062A patent/CZ299881B6/cs not_active IP Right Cessation
- 1999-07-22 KR KR10-2001-7000778A patent/KR100529201B1/ko not_active IP Right Cessation
- 1999-07-22 NZ NZ509401A patent/NZ509401A/xx not_active IP Right Cessation
- 1999-07-22 DE DE69926760T patent/DE69926760T2/de not_active Expired - Lifetime
- 1999-07-22 IL IL14092499A patent/IL140924A0/xx active IP Right Grant
- 1999-07-22 AT AT99931484T patent/ATE302190T1/de active
- 1999-07-22 ES ES99931484T patent/ES2247813T3/es not_active Expired - Lifetime
- 1999-07-22 JP JP2000561169A patent/JP4281248B2/ja not_active Expired - Fee Related
-
2001
- 2001-01-16 IL IL140924A patent/IL140924A/en not_active IP Right Cessation
- 2001-01-18 ZA ZA200100525A patent/ZA200100525B/en unknown
- 2001-01-22 NO NO20010357A patent/NO317787B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69926760T2 (de) | 2006-01-19 |
| IL140924A0 (en) | 2002-02-10 |
| DE69926760D1 (de) | 2005-09-22 |
| CN1107670C (zh) | 2003-05-07 |
| CZ299881B6 (cs) | 2008-12-17 |
| WO2000005213A1 (fr) | 2000-02-03 |
| MXPA01000890A (es) | 2002-06-04 |
| EP1099694A1 (en) | 2001-05-16 |
| JP4281248B2 (ja) | 2009-06-17 |
| ES2247813T3 (es) | 2006-03-01 |
| ATE302190T1 (de) | 2005-09-15 |
| EP1099694B1 (en) | 2005-08-17 |
| DK1099694T3 (da) | 2005-09-19 |
| NO317787B1 (no) | 2004-12-13 |
| SK285675B6 (sk) | 2007-06-07 |
| CA2338334C (en) | 2008-07-15 |
| CA2338334A1 (en) | 2000-02-03 |
| AU746722B2 (en) | 2002-05-02 |
| IL140924A (en) | 2006-06-11 |
| RU2214402C2 (ru) | 2003-10-20 |
| AU4799299A (en) | 2000-02-14 |
| CZ200162A3 (en) | 2001-06-13 |
| NO20010357L (no) | 2001-01-22 |
| AU746722C (en) | 2003-03-27 |
| NO20010357D0 (no) | 2001-01-22 |
| SK622001A3 (en) | 2001-08-06 |
| KR20010070987A (ko) | 2001-07-28 |
| EP1099694A4 (en) | 2002-08-14 |
| NZ509401A (en) | 2002-08-28 |
| PT1099694E (pt) | 2005-10-31 |
| KR100529201B1 (ko) | 2005-11-17 |
| US6335449B1 (en) | 2002-01-01 |
| CN1310711A (zh) | 2001-08-29 |
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