TWI347317B - Process for preparing 8-substituted oxy-5-(r)-2-halo-1-hydroxy-ethyl)-(1h)-quinolin-2-ones or acceptable solvates thereof and use of the product obtained therefrom - Google Patents
Process for preparing 8-substituted oxy-5-(r)-2-halo-1-hydroxy-ethyl)-(1h)-quinolin-2-ones or acceptable solvates thereof and use of the product obtained therefromInfo
- Publication number
- TWI347317B TWI347317B TW094120524A TW94120524A TWI347317B TW I347317 B TWI347317 B TW I347317B TW 094120524 A TW094120524 A TW 094120524A TW 94120524 A TW94120524 A TW 94120524A TW I347317 B TWI347317 B TW I347317B
- Authority
- TW
- Taiwan
- Prior art keywords
- quinolin
- halo
- hydroxy
- ones
- ethyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000012453 solvate Substances 0.000 title 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
- C07D215/16—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- C07D215/16—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/04—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D251/06—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0413960.6A GB0413960D0 (en) | 2004-06-22 | 2004-06-22 | Organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200615265A TW200615265A (en) | 2006-05-16 |
| TWI347317B true TWI347317B (en) | 2011-08-21 |
Family
ID=32799952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094120524A TWI347317B (en) | 2004-06-22 | 2005-06-21 | Process for preparing 8-substituted oxy-5-(r)-2-halo-1-hydroxy-ethyl)-(1h)-quinolin-2-ones or acceptable solvates thereof and use of the product obtained therefrom |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US20090054653A1 (zh) |
| EP (1) | EP1791820B1 (zh) |
| JP (1) | JP5064214B2 (zh) |
| KR (1) | KR101179302B1 (zh) |
| CN (1) | CN1968927B (zh) |
| AR (2) | AR049553A1 (zh) |
| AT (1) | ATE450512T1 (zh) |
| AU (1) | AU2005254698B2 (zh) |
| BR (1) | BRPI0512298A (zh) |
| CA (1) | CA2566388C (zh) |
| CY (1) | CY1109884T1 (zh) |
| DE (1) | DE602005018076D1 (zh) |
| DK (1) | DK1791820T3 (zh) |
| EC (1) | ECSP067100A (zh) |
| ES (1) | ES2337273T3 (zh) |
| GB (1) | GB0413960D0 (zh) |
| HR (1) | HRP20100087T1 (zh) |
| IL (1) | IL179600A (zh) |
| MA (1) | MA28687B1 (zh) |
| MX (1) | MXPA06014695A (zh) |
| MY (1) | MY142051A (zh) |
| NO (1) | NO339079B1 (zh) |
| NZ (1) | NZ551276A (zh) |
| PE (1) | PE20060304A1 (zh) |
| PL (1) | PL1791820T3 (zh) |
| PT (1) | PT1791820E (zh) |
| RU (1) | RU2383534C2 (zh) |
| SI (1) | SI1791820T1 (zh) |
| TN (1) | TNSN06408A1 (zh) |
| TW (1) | TWI347317B (zh) |
| WO (1) | WO2005123684A2 (zh) |
| ZA (1) | ZA200609257B (zh) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2396987T3 (es) | 2006-06-30 | 2013-03-01 | Novartis Ag | Derivados de quinolina y sus composiciones farmacéuticas |
| EP1914227A1 (en) * | 2006-08-31 | 2008-04-23 | Novartis AG | Polymorphic crystal form of a indan-2-ylamino-hydroxyethyl-quinolinone maleate derivative as beta-adrenoceptor agonist |
| US8877930B2 (en) | 2009-11-04 | 2014-11-04 | Massachusetts Institute Of Technology | Continuous flow synthesis of amino alcohols using microreactors |
| US8680303B2 (en) | 2010-03-01 | 2014-03-25 | Massachusetts Institute Of Technology | Epoxidation catalysts |
| EA022046B1 (ru) | 2010-07-14 | 2015-10-30 | Новартис Аг | Гетероциклические соединения, агонисты рецептора ip |
| JOP20120023B1 (ar) | 2011-02-04 | 2022-03-14 | Novartis Ag | صياغات مساحيق جافة من جسيمات تحتوي على واحد أو اثنين من المواد الفعالة لعلاج امراض ممرات الهواء الانسدادية او الالتهابية |
| AR089698A1 (es) | 2012-01-13 | 2014-09-10 | Novartis Ag | Compuestos heterociclicos antagonistas del receptor ip |
| US9115129B2 (en) | 2012-01-13 | 2015-08-25 | Novartis Ag | Substituted pyrido[2,3-B]pyrazines as IP receptor agonists |
| US20150005311A1 (en) | 2012-01-13 | 2015-01-01 | Novartis Ag | IP receptor agonist heterocyclic compounds |
| EP2802584B1 (en) | 2012-01-13 | 2015-11-18 | Novartis AG | Salts of an ip receptor agonist |
| US20140357641A1 (en) | 2012-01-13 | 2014-12-04 | Novartis Ag | IP receptor agonist heterocyclic compounds |
| EP2802581A1 (en) | 2012-01-13 | 2014-11-19 | Novartis AG | 7,8- dihydropyrido [3, 4 - b]pyrazines as ip receptor agonists for the treatment of pulmonary arterial hypertension (pah) and related disorders |
| CN104379566B (zh) * | 2012-07-11 | 2016-08-24 | 上海威智医药科技有限公司 | 茚达特罗中间体及茚达特罗的合成方法 |
| EP3138837B1 (en) | 2012-09-21 | 2021-11-24 | Crystal Pharma, S.A.U. | Indacaterol free base in solid form |
| WO2014044288A1 (en) | 2012-09-21 | 2014-03-27 | Crystal Pharma Sa | Methods for the preparation of indacaterol and pharmaceutically acceptable salts thereof |
| CA2895448A1 (en) | 2012-12-19 | 2014-06-26 | Novartis Ag | Autotaxin inhibitors |
| US9604981B2 (en) | 2013-02-13 | 2017-03-28 | Novartis Ag | IP receptor agonist heterocyclic compounds |
| US9452139B2 (en) | 2013-03-14 | 2016-09-27 | Novartis Ag | Respirable agglomerates of porous carrier particles and micronized drug |
| BR112015020443A8 (pt) | 2013-03-14 | 2019-11-12 | Novartis Ag | formulação em pó para inalação, seus usos e seu processo de preparação, e composição farmacêutica |
| CZ306252B6 (cs) | 2013-03-15 | 2016-10-26 | Zentiva, K.S. | Způsob přípravy 5-[(R)-2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-(1H)-chinolin-2-onu (indacaterolu) |
| WO2014154841A1 (en) | 2013-03-27 | 2014-10-02 | Laboratorios Lesvi, S.L. | Process for the manufacture of (r)-5-[2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-(1h)-quinolin-2-one |
| US20160168119A1 (en) | 2013-07-18 | 2016-06-16 | Novartis Ag | Autotaxin inhibitors |
| US9763957B2 (en) | 2013-07-18 | 2017-09-19 | Novartis Ag | Autotaxin inhibitors |
| ES2815123T3 (es) | 2014-01-09 | 2021-03-29 | Davuluri Ramamohan Rao | Proceso novedoso para la preparación de indacaterol o sus sales aceptables farmacéuticamente |
| RU2016141948A (ru) | 2014-03-27 | 2018-04-27 | Новартис Аг | Высушенные распылением дисперсии твердое-в-масле-в-воде активных фармацевтических ингредиентов для ингаляции |
| EP3134398A1 (en) | 2014-04-24 | 2017-03-01 | Novartis Ag | Autotaxin inhibitors |
| CN105693603B (zh) * | 2014-11-24 | 2019-11-29 | 上海医药工业研究院 | 改良的马来酸茚达特罗制备工艺 |
| KR101769204B1 (ko) * | 2015-08-04 | 2017-08-17 | 씨제이헬스케어 주식회사 | 크로마놀 유도체의 신규한 제조방법 |
| ES2747905T3 (es) | 2015-09-29 | 2020-03-12 | Inke Sa | Solvato mixto de L-tartrato de (R)-5-[2-(5,6-dietilindan-2-ilamino)-1-hidroxietil]-8-hidroxi-1H-quinolin-2-ona |
| US10418663B2 (en) | 2016-05-17 | 2019-09-17 | Industrial Technology Research Institute | Metal-ion battery |
| CN107868045A (zh) * | 2016-09-28 | 2018-04-03 | 四川海思科制药有限公司 | 一种茚达特罗中间体的制备方法 |
| CN114591236A (zh) * | 2020-12-02 | 2022-06-07 | 四川海思科制药有限公司 | 一种茚达特罗的改进制备方法 |
| CN113731406B (zh) * | 2021-10-12 | 2023-07-28 | 南京工业大学 | 一种提高钯碳活性加氢脱除保护基的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9405019D0 (en) * | 1994-03-15 | 1994-04-27 | Smithkline Beecham Plc | Novel compounds |
| EP0952832B1 (en) * | 1996-05-20 | 2008-08-27 | Darwin Discovery Limited | Quinoline carboxamides as tnf inhibitors and as pde-iv inhibitors |
| GB9913083D0 (en) * | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| TWI249515B (en) * | 2001-11-13 | 2006-02-21 | Theravance Inc | Aryl aniline beta2 adrenergic receptor agonists |
| TWI324150B (en) * | 2003-02-28 | 2010-05-01 | Novartis Ag | Process for preparing 5-[(r)-2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-8-hydroxy-(1h)-quinolin-2-one salt |
| PE20100399A1 (es) * | 2003-04-02 | 2010-06-01 | Novartis Ag | Procedimiento para preparar oxi-(1h)-quinolin-2-onas 5-(alfa-haloacetil)-8-sustituidas |
-
2004
- 2004-06-22 GB GBGB0413960.6A patent/GB0413960D0/en not_active Ceased
-
2005
- 2005-06-17 AR ARP050102511A patent/AR049553A1/es not_active Application Discontinuation
- 2005-06-20 PE PE2005000704A patent/PE20060304A1/es active IP Right Grant
- 2005-06-20 MY MYPI20052795A patent/MY142051A/en unknown
- 2005-06-21 ES ES05770221T patent/ES2337273T3/es not_active Expired - Lifetime
- 2005-06-21 DK DK05770221.9T patent/DK1791820T3/da active
- 2005-06-21 PL PL05770221T patent/PL1791820T3/pl unknown
- 2005-06-21 BR BRPI0512298-8A patent/BRPI0512298A/pt not_active Application Discontinuation
- 2005-06-21 SI SI200530921T patent/SI1791820T1/sl unknown
- 2005-06-21 AT AT05770221T patent/ATE450512T1/de active
- 2005-06-21 MX MXPA06014695A patent/MXPA06014695A/es active IP Right Grant
- 2005-06-21 DE DE602005018076T patent/DE602005018076D1/de not_active Expired - Lifetime
- 2005-06-21 CA CA2566388A patent/CA2566388C/en not_active Expired - Lifetime
- 2005-06-21 PT PT05770221T patent/PT1791820E/pt unknown
- 2005-06-21 NZ NZ551276A patent/NZ551276A/en not_active IP Right Cessation
- 2005-06-21 EP EP05770221A patent/EP1791820B1/en not_active Expired - Lifetime
- 2005-06-21 WO PCT/EP2005/006686 patent/WO2005123684A2/en not_active Ceased
- 2005-06-21 HR HR20100087T patent/HRP20100087T1/hr unknown
- 2005-06-21 TW TW094120524A patent/TWI347317B/zh active
- 2005-06-21 AU AU2005254698A patent/AU2005254698B2/en not_active Expired
- 2005-06-21 RU RU2007102228/04A patent/RU2383534C2/ru active
- 2005-06-21 CN CN2005800195899A patent/CN1968927B/zh not_active Expired - Lifetime
- 2005-06-21 US US11/569,140 patent/US20090054653A1/en not_active Abandoned
- 2005-06-21 KR KR1020067026958A patent/KR101179302B1/ko not_active Expired - Lifetime
- 2005-06-21 JP JP2007517180A patent/JP5064214B2/ja not_active Expired - Lifetime
-
2006
- 2006-11-07 ZA ZA200609257A patent/ZA200609257B/en unknown
- 2006-11-27 IL IL179600A patent/IL179600A/en active IP Right Grant
- 2006-12-08 TN TNP2006000408A patent/TNSN06408A1/en unknown
- 2006-12-20 EC EC2006007100A patent/ECSP067100A/es unknown
- 2006-12-28 MA MA29571A patent/MA28687B1/fr unknown
-
2007
- 2007-01-22 NO NO20070400A patent/NO339079B1/no unknown
-
2010
- 2010-03-01 CY CY20101100199T patent/CY1109884T1/el unknown
-
2011
- 2011-09-14 AR ARP110103340A patent/AR082981A2/es unknown
-
2012
- 2012-05-01 US US13/461,204 patent/US20120220775A1/en not_active Abandoned
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