NO317787B1 - Fremgangsmate for fremstilling av kinolinderivat og mellomprodukt - Google Patents
Fremgangsmate for fremstilling av kinolinderivat og mellomprodukt Download PDFInfo
- Publication number
- NO317787B1 NO317787B1 NO20010357A NO20010357A NO317787B1 NO 317787 B1 NO317787 B1 NO 317787B1 NO 20010357 A NO20010357 A NO 20010357A NO 20010357 A NO20010357 A NO 20010357A NO 317787 B1 NO317787 B1 NO 317787B1
- Authority
- NO
- Norway
- Prior art keywords
- preparation
- stirred
- quinoline
- quinoline derivative
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims abstract 3
- 238000002360 preparation method Methods 0.000 title abstract description 9
- KWMBADTWRIGGGG-UHFFFAOYSA-N 2-diethoxyphosphorylacetonitrile Chemical compound CCOP(=O)(CC#N)OCC KWMBADTWRIGGGG-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 Nitrile compound Chemical class 0.000 claims description 31
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 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
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 4
- 150000003248 quinolines Chemical class 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000010410 layer 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 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
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 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
- 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 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 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
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HASGOCLZFTZSTN-UHFFFAOYSA-N cyclohexane;hexane Chemical compound CCCCCC.C1CCCCC1 HASGOCLZFTZSTN-UHFFFAOYSA-N 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
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 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
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20791198 | 1998-07-23 | ||
| PCT/JP1999/003923 WO2000005213A1 (fr) | 1998-07-23 | 1999-07-22 | Procede de preparation d'un derive de quinoleine et produit intermediaire pour ce procede |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20010357D0 NO20010357D0 (no) | 2001-01-22 |
| NO20010357L NO20010357L (no) | 2001-01-22 |
| NO317787B1 true NO317787B1 (no) | 2004-12-13 |
Family
ID=16547618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20010357A NO317787B1 (no) | 1998-07-23 | 2001-01-22 | Fremgangsmate for fremstilling av kinolinderivat og mellomprodukt |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6335449B1 (pt) |
| EP (1) | EP1099694B1 (pt) |
| JP (1) | JP4281248B2 (pt) |
| KR (1) | KR100529201B1 (pt) |
| CN (1) | CN1107670C (pt) |
| AT (1) | ATE302190T1 (pt) |
| AU (1) | AU746722C (pt) |
| CA (1) | CA2338334C (pt) |
| CZ (1) | CZ299881B6 (pt) |
| DE (1) | DE69926760T2 (pt) |
| DK (1) | DK1099694T3 (pt) |
| ES (1) | ES2247813T3 (pt) |
| IL (2) | IL140924A0 (pt) |
| MX (1) | MXPA01000890A (pt) |
| NO (1) | NO317787B1 (pt) |
| NZ (1) | NZ509401A (pt) |
| PT (1) | PT1099694E (pt) |
| RU (1) | RU2214402C2 (pt) |
| SK (1) | SK285675B6 (pt) |
| WO (1) | WO2000005213A1 (pt) |
| ZA (1) | ZA200100525B (pt) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| WO2001053265A1 (fr) * | 2000-01-24 | 2001-07-26 | Ube Industries, Ltd. | Procede de preparation de quinolylpropenal |
| 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 |
| DE60125915T2 (de) * | 2000-02-21 | 2007-10-11 | Nissan Chemical Industries, Ltd. | Verfahren zum herstellen von chinolinderivaten und deren intermediaten |
| CN1230173C (zh) * | 2000-10-12 | 2005-12-07 | 日产化学工业株式会社 | 糖尿病合并症预防及治疗剂 |
| 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 |
| TWI309644B (pt) * | 2001-02-14 | 2009-05-11 | Nissan Chemical Ind Ltd | |
| 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 |
| KR20040026705A (ko) | 2001-08-16 | 2004-03-31 | 테바 파마슈티컬 인더스트리즈 리미티드 | 스타틴의 칼슘 염 형태의 제조 방법 |
| CN102285916B (zh) * | 2003-02-12 | 2015-02-25 | 日产化学工业株式会社 | 匹伐他汀钙的晶形 |
| 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 |
| WO2010089770A2 (en) | 2009-01-19 | 2010-08-12 | Msn Laboratories Limited | Improved process for the preparation of highly pure (3r,5s)-7-[2-cyclopropyl-4-(4-fluorophenyl) quinolin-3-yl]-3,5-dihydroxy-6(e)-heptenoic acid and pharmaceutically acceptable salts thereof |
| WO2011086584A2 (en) | 2010-01-18 | 2011-07-21 | Msn Laboratories Limited | Improved process for the preparation of amide intermediates and their use thereof |
| WO2011089623A2 (en) | 2010-01-20 | 2011-07-28 | Cadila Healthcare Limited | Process for preparing pitavastatin and pharmaceutically 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 |
| CA2954215A1 (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 |
| 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 |
| US5854259A (en) | 1987-08-20 | 1998-12-29 | Nissan Chemical Industries Ltd. | Quinoline type mevalonolactones |
| 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 |
| AU691582B2 (en) | 1994-02-25 | 1998-05-21 | Daicel Chemical Industries Ltd. | Process for producing optically active mevalonolactone compound |
-
1999
- 1999-07-22 WO PCT/JP1999/003923 patent/WO2000005213A1/ja active IP Right Grant
- 1999-07-22 CN CN99809003A patent/CN1107670C/zh not_active Expired - Fee Related
- 1999-07-22 RU RU2001105200/04A patent/RU2214402C2/ru not_active IP Right Cessation
- 1999-07-22 AU AU47992/99A patent/AU746722C/en not_active Ceased
- 1999-07-22 EP EP99931484A patent/EP1099694B1/en not_active Expired - Lifetime
- 1999-07-22 PT PT99931484T patent/PT1099694E/pt unknown
- 1999-07-22 CZ CZ20010062A patent/CZ299881B6/cs not_active IP Right Cessation
- 1999-07-22 SK SK62-2001A patent/SK285675B6/sk not_active IP Right Cessation
- 1999-07-22 IL IL14092499A patent/IL140924A0/xx active IP Right Grant
- 1999-07-22 MX MXPA01000890A patent/MXPA01000890A/es not_active IP Right Cessation
- 1999-07-22 DK DK99931484T patent/DK1099694T3/da active
- 1999-07-22 JP JP2000561169A patent/JP4281248B2/ja not_active Expired - Fee Related
- 1999-07-22 DE DE69926760T patent/DE69926760T2/de not_active Expired - Lifetime
- 1999-07-22 ES ES99931484T patent/ES2247813T3/es not_active Expired - Lifetime
- 1999-07-22 US US09/764,994 patent/US6335449B1/en not_active Expired - Lifetime
- 1999-07-22 AT AT99931484T patent/ATE302190T1/de active
- 1999-07-22 NZ NZ509401A patent/NZ509401A/xx not_active IP Right Cessation
- 1999-07-22 KR KR10-2001-7000778A patent/KR100529201B1/ko not_active IP Right Cessation
- 1999-07-22 CA CA002338334A patent/CA2338334C/en 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 |
|---|---|
| NZ509401A (en) | 2002-08-28 |
| CZ200162A3 (en) | 2001-06-13 |
| WO2000005213A1 (fr) | 2000-02-03 |
| KR100529201B1 (ko) | 2005-11-17 |
| IL140924A0 (en) | 2002-02-10 |
| JP4281248B2 (ja) | 2009-06-17 |
| CZ299881B6 (cs) | 2008-12-17 |
| NO20010357D0 (no) | 2001-01-22 |
| DK1099694T3 (da) | 2005-09-19 |
| DE69926760D1 (de) | 2005-09-22 |
| CA2338334C (en) | 2008-07-15 |
| EP1099694A1 (en) | 2001-05-16 |
| EP1099694A4 (en) | 2002-08-14 |
| US6335449B1 (en) | 2002-01-01 |
| IL140924A (en) | 2006-06-11 |
| SK622001A3 (en) | 2001-08-06 |
| MXPA01000890A (es) | 2002-06-04 |
| AU746722B2 (en) | 2002-05-02 |
| ATE302190T1 (de) | 2005-09-15 |
| PT1099694E (pt) | 2005-10-31 |
| RU2214402C2 (ru) | 2003-10-20 |
| ZA200100525B (en) | 2001-08-01 |
| DE69926760T2 (de) | 2006-01-19 |
| AU4799299A (en) | 2000-02-14 |
| EP1099694B1 (en) | 2005-08-17 |
| CN1310711A (zh) | 2001-08-29 |
| AU746722C (en) | 2003-03-27 |
| SK285675B6 (sk) | 2007-06-07 |
| CA2338334A1 (en) | 2000-02-03 |
| CN1107670C (zh) | 2003-05-07 |
| NO20010357L (no) | 2001-01-22 |
| KR20010070987A (ko) | 2001-07-28 |
| ES2247813T3 (es) | 2006-03-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO317787B1 (no) | Fremgangsmate for fremstilling av kinolinderivat og mellomprodukt | |
| US5473075A (en) | Diastereomer salt of optically active quinolinemevalonic acid | |
| US4474788A (en) | Anti-SRSA quinoline carboxylic acid derivatives | |
| RU2094428C1 (ru) | Способ получения бензопирановых соединений, промежуточные соединения и способы их получения | |
| KR20040010720A (ko) | 피페리딘 유도체 펙소페나딘의 제조방법 | |
| US5663370A (en) | Chemical intermediates useful in agriculture | |
| US5258525A (en) | Processes for preparing [2S-(2α,3aβ,7aβ)]octahydro-1H-indole-2-carboxylic acid and esters | |
| NO179680B (no) | Fremgangsmåte ved fremstilling av 2R-benzylchroman-6-karbaldehyd | |
| JP3219946B2 (ja) | 新規製造中間体及びピリジン誘導体の製造方法 | |
| JP2006528655A (ja) | スタチン、特にアトルバスタチンの調製において有用な方法および中間体化合物 | |
| JP2004508371A (ja) | 置換イミダゾピリジン化合物の製造方法 | |
| CA2448421C (en) | Process for producing quinoline carbaldehyde | |
| US5008403A (en) | Deacylative bromination process for the preparation of molluscicidal 2,4,5-tribromopyrrole-3-carbonitrile compounds | |
| EP0452094A2 (en) | A method of the preparation of N-hydroxy aspartic acid derivate | |
| UA65627C2 (uk) | Спосіб одержання похідної сполуки хіноліну та проміжна сполука | |
| US5530136A (en) | Process for the preparation of pilocarpine derivatives from a 5-formyl-imidazole derivative | |
| JP6256469B2 (ja) | スピロ［２．５］オクタン−５，７−ジオンの調製プロセス | |
| JP4280464B2 (ja) | ４−トリフルオロメチルニコチン酸又はその塩の製造方法 | |
| JPH0873454A (ja) | シクロヘプトイミダゾ−ル誘導体の製造法 | |
| KR20010023347A (ko) | 1-(3-시클로펜틸옥시-4-알콕시페닐)-4-옥소시클로헥산카르보니트릴의 제조 방법 | |
| CA2416454A1 (en) | Intermediates for synthesis of vinblastine and its congeners, and a method for synthesis of the intermediates | |
| KR20090104898A (ko) | (ｒ)-5-(2-아미노에틸)-1-(6,8-디플루오로크로만-3-일)-1,3-디히드로이미다졸-2-티온의 제조 방법 | |
| JPH08165282A (ja) | ２−アルキル−４−オキソ−５、６、７、８−テトラヒドロ−シクロヘプトイミダゾ−ルの製造方法 | |
| NO155196B (no) | Fremgangsmaate ved fremstilling av 4-aminohex-5-en-syre eller et salt derav. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |