AR082981A2 - Proceso para la preparacion de sales de 5-[(r)-2-(5,6-dietil-indan-2-ilamino)-1-hidroxi-etil]-8-hidroxi-(1h)-quinolin-2-ona - Google Patents
Proceso para la preparacion de sales de 5-[(r)-2-(5,6-dietil-indan-2-ilamino)-1-hidroxi-etil]-8-hidroxi-(1h)-quinolin-2-onaInfo
- Publication number
- AR082981A2 AR082981A2 ARP110103340A ARP110103340A AR082981A2 AR 082981 A2 AR082981 A2 AR 082981A2 AR P110103340 A ARP110103340 A AR P110103340A AR P110103340 A ARP110103340 A AR P110103340A AR 082981 A2 AR082981 A2 AR 082981A2
- Authority
- AR
- Argentina
- Prior art keywords
- quinolin
- hydroxy
- formula
- oxy
- substituted
- Prior art date
Links
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)
Abstract
Un proceso para la preparación de sales de 5-[(R)-2-(5,6-dietil-indan-2-ilamino)-1-hidroxi-etil]-8-hidroxi-(1H)-quinolin-2-ona (a) se hace reaccionar (i) 8-hidroxi-(1H)-quinolin-2-ona con un agente acilante y un ácido de Lewis para formar 5-acetil-8-hidroxi-(1H)-quinolin-2-ona; o (ii) 8-hidroxi-(1H)-quinolin-2-ona con un agente acilante para formar 8-acetoxi-(1H)-quinolin-2-ona, y tratar, in situ, la 8-acetoxi-(1H)-quinolin-2-ona con un ácido de Lewis para formar 5-acetil-8-hidroxi-(1H)-quinolin-2-ona; o (iii) 8-acetoxi-(1H)-quinolin-2-ona con un ácido de Lewis para formar 5-acetil-8-hidroxi-(1H)-quinolin-2-ona; (b) se hace reaccionar la 5-acetil-8-hidroxi-(1H)-quinolin-2-ona preparada en el Paso (a) con un compuesto que tiene la fórmula R-Q en presencia de una base y un solvente para formar oxi-(1H)-quinolin-2-ona 5-acetil-8 sustituida, en donde R es un grupo protector y Q es un grupo saliente; (c) se hace reaccionar la oxi-(1H)-quinolin-2-ona 5-acetil-8 sustituida con un agente de halogenación en presencia de un solvente para formar una oxi-(1H)-quinolin-2-ona 5(a-haloacetil)-8-sustituida; (d) se hace reaccionar la oxi-(1H)-quinolin-2-ona 5(a-haloacetil)-8-sustituida con un agente reductor en presencia de un agente quiral y una base para formar oxi-5-((R)-2-halo-1-hidroxi-etil)-(1H)-quinolin-2-ona, teniendo este agente quiral la fórmula (1) ó (2); en donde M es Ru, Rh, Ir, Fe, Co o Ni; L es arilo C6-24, o un residuo arilo C6-24-alifático C1-10, estando en cualquier caso opcionalmente enlazado con un polímero; X es hidrógeno o halógeno; R1 es un residuo alifático C1-10, cicloalifático C3-10, cicloalifático C3-10-alifático C1-10, arilo C6-24-alifático C1-10, o un grupo heterocíclico de 4 a 12 miembros que, en cada caso, está opcionalmente enlazado con un polímero; y R2 y R3 son fenilo, o R2 y R3, junto con el átomo de carbono con el que están unidos, forman un anillo de ciclohexano o ciclopentano; (e) se trata la oxi-5-((R)-2-halo-1-hidroxi-etilo)-(1H)-quinolin-2-ona 8-sustituida con una base en presencia de un solvente para formar una oxi-5-(R)-oxiranil-(1H)-quinolin-2-ona 8-sustituida de la fórmula (3) en donde R es un agente protector; (f) se hace reaccionar la oxi-5-(R)-oxiranil-(1H)-quinolin-2-ona 8-sustituida de la fórmula (3), en donde R es como se define anteriormente en la presente, con 2-amino-(5,6-dietil)-indano, para formar una mezcla de reacción que contiene los compuestos que tienen las fórmulas (4), (5), y (6) en donde R es un grupo protector; (g) se trata la mezcla de reacción preparada en el paso (f) con un ácido en presencia de un solvente para formar la sal correspondiente; (h) se aísla y cristaliza una sal que tiene la fórmula (7) en donde R es un grupo protector y A es un anión; (i) se elimina el grupo protector de la sal que tiene la fórmula (7) en presencia de un solvente para formar una sal que tiene la fórmula (8) en donde A es un anión; y (j) se trata la sal que tiene la fórmula (8) con un ácido en la presencia de un solvente, para formar la sal de 5-[(R)-2-(5,6-dietil-indan-2-ilamino)-1-hidroxi-etiI]-8hidroxi-(1H)-quinolin-2-ona que tiene la fórmula (9), en donde X es un anión. Las sales son útiles para tratar asma y enfermedad pulmonar obstructiva crónica.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0413960.6A GB0413960D0 (en) | 2004-06-22 | 2004-06-22 | Organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR082981A2 true AR082981A2 (es) | 2013-01-23 |
Family
ID=32799952
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP050102511A AR049553A1 (es) | 2004-06-22 | 2005-06-17 | Procesos para preparar compuestos e intermediarios quinolin-2-onas 8- sustituidas |
| ARP110103340A AR082981A2 (es) | 2004-06-22 | 2011-09-14 | Proceso para la preparacion de sales de 5-[(r)-2-(5,6-dietil-indan-2-ilamino)-1-hidroxi-etil]-8-hidroxi-(1h)-quinolin-2-ona |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP050102511A AR049553A1 (es) | 2004-06-22 | 2005-06-17 | Procesos para preparar compuestos e intermediarios quinolin-2-onas 8- sustituidas |
Country Status (33)
| Country | Link |
|---|---|
| US (2) | US20090054653A1 (es) |
| EP (1) | EP1791820B1 (es) |
| JP (1) | JP5064214B2 (es) |
| KR (1) | KR101179302B1 (es) |
| CN (1) | CN1968927B (es) |
| AR (2) | AR049553A1 (es) |
| AT (1) | ATE450512T1 (es) |
| AU (1) | AU2005254698B2 (es) |
| BR (1) | BRPI0512298A (es) |
| CA (1) | CA2566388C (es) |
| CY (1) | CY1109884T1 (es) |
| DE (1) | DE602005018076D1 (es) |
| DK (1) | DK1791820T3 (es) |
| EC (1) | ECSP067100A (es) |
| ES (1) | ES2337273T3 (es) |
| GB (1) | GB0413960D0 (es) |
| HK (1) | HK1105121A1 (es) |
| HR (1) | HRP20100087T1 (es) |
| IL (1) | IL179600A (es) |
| MA (1) | MA28687B1 (es) |
| MX (1) | MXPA06014695A (es) |
| MY (1) | MY142051A (es) |
| NO (1) | NO339079B1 (es) |
| NZ (1) | NZ551276A (es) |
| PE (1) | PE20060304A1 (es) |
| PL (1) | PL1791820T3 (es) |
| PT (1) | PT1791820E (es) |
| RU (1) | RU2383534C2 (es) |
| SI (1) | SI1791820T1 (es) |
| TN (1) | TNSN06408A1 (es) |
| TW (1) | TWI347317B (es) |
| WO (1) | WO2005123684A2 (es) |
| ZA (1) | ZA200609257B (es) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8198450B2 (en) | 2006-06-30 | 2012-06-12 | Novartis Ag | Quinolinone derivatives and their pharmaceutical compositions |
| 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 |
| WO2011109276A1 (en) | 2010-03-01 | 2011-09-09 | Massachussets Institute Of Technology | Epoxidation catalysts |
| SI2593452T1 (sl) | 2010-07-14 | 2017-06-30 | Novartis Ag | Heterociklične spojine agonisti receptorja 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 |
| US20140357641A1 (en) | 2012-01-13 | 2014-12-04 | Novartis Ag | IP receptor agonist heterocyclic compounds |
| ES2561353T3 (es) | 2012-01-13 | 2016-02-25 | Novartis Ag | Sales de un agonista del receptor IP |
| ES2565826T3 (es) | 2012-01-13 | 2016-04-07 | Novartis Ag | Pirroles fusionados como agonistas del receptor IP para el tratamiento de hipertensión arterial pulmonar (PAH) y trastornos relacionados |
| 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 |
| US9115129B2 (en) | 2012-01-13 | 2015-08-25 | Novartis Ag | Substituted pyrido[2,3-B]pyrazines as IP receptor agonists |
| EP2802583A1 (en) | 2012-01-13 | 2014-11-19 | Novartis AG | Fused piperidines as ip receptor agonists for the treatment of pulmonary arterial hypertension (pah) and related disorders |
| WO2014008640A1 (zh) * | 2012-07-11 | 2014-01-16 | 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 |
| EP3848354B1 (en) | 2012-09-21 | 2022-07-27 | Crystal Pharma, S.A.U. | Process for the preparation of indacaterol and intermediates thereof |
| WO2014044288A1 (en) | 2012-09-21 | 2014-03-27 | Crystal Pharma Sa | Methods for the preparation of indacaterol and pharmaceutically acceptable salts thereof |
| JP6363616B2 (ja) | 2012-12-19 | 2018-07-25 | ノバルティス アーゲー | オートタキシン阻害剤 |
| WO2014125413A1 (en) | 2013-02-13 | 2014-08-21 | Novartis Ag | Ip receptor agonist heterocyclic compounds |
| MX2015012529A (es) | 2013-03-14 | 2016-07-05 | Novartis Ag | Deamorfizacion de formulaciones secadas por pulverizacion a traves de pulverizacion de la mezcla. |
| US9452139B2 (en) | 2013-03-14 | 2016-09-27 | Novartis Ag | Respirable agglomerates of porous carrier particles and micronized drug |
| 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) |
| EP2978745B1 (en) | 2013-03-27 | 2017-03-15 | 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 |
| EP3022201A1 (en) | 2013-07-18 | 2016-05-25 | Novartis AG | Autotaxin inhibitors |
| AU2014291711B2 (en) | 2013-07-18 | 2017-02-02 | Novartis Ag | Autotaxin inhibitors comprising a heteroaromatic ring-benzyl-amide-cycle core |
| WO2015104718A2 (en) | 2014-01-09 | 2015-07-16 | Davuluri, Ramamohan Rao | A novel process for preparation of indacaterol or its pharmaceutically acceptable salts |
| RU2016141948A (ru) | 2014-03-27 | 2018-04-27 | Новартис Аг | Высушенные распылением дисперсии твердое-в-масле-в-воде активных фармацевтических ингредиентов для ингаляции |
| US20170037030A1 (en) | 2014-04-24 | 2017-02-09 | 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 |
| WO2017055506A1 (en) | 2015-09-29 | 2017-04-06 | Laboratorios Lesvi, S.L. | Mixed solvate of (r)-5-[2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl] -8-hydroxy-1h-quinolin-2-one l-tartrate |
| CN107394260B (zh) * | 2016-05-17 | 2020-06-09 | 财团法人工业技术研究院 | 金属离子电池 |
| 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 |
| 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 (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9405019D0 (en) * | 1994-03-15 | 1994-04-27 | Smithkline Beecham Plc | Novel compounds |
| 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 |
| PE20050211A1 (es) * | 2003-04-02 | 2005-04-27 | 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 MY MYPI20052795A patent/MY142051A/en unknown
- 2005-06-20 PE PE2005000704A patent/PE20060304A1/es active IP Right Grant
- 2005-06-21 WO PCT/EP2005/006686 patent/WO2005123684A2/en active Application Filing
- 2005-06-21 AT AT05770221T patent/ATE450512T1/de active
- 2005-06-21 KR KR1020067026958A patent/KR101179302B1/ko active IP Right Grant
- 2005-06-21 EP EP05770221A patent/EP1791820B1/en active Active
- 2005-06-21 US US11/569,140 patent/US20090054653A1/en not_active Abandoned
- 2005-06-21 MX MXPA06014695A patent/MXPA06014695A/es active IP Right Grant
- 2005-06-21 JP JP2007517180A patent/JP5064214B2/ja active Active
- 2005-06-21 DK DK05770221.9T patent/DK1791820T3/da active
- 2005-06-21 AU AU2005254698A patent/AU2005254698B2/en active Active
- 2005-06-21 CA CA2566388A patent/CA2566388C/en active Active
- 2005-06-21 NZ NZ551276A patent/NZ551276A/en unknown
- 2005-06-21 ES ES05770221T patent/ES2337273T3/es active Active
- 2005-06-21 PL PL05770221T patent/PL1791820T3/pl unknown
- 2005-06-21 PT PT05770221T patent/PT1791820E/pt unknown
- 2005-06-21 SI SI200530921T patent/SI1791820T1/sl unknown
- 2005-06-21 DE DE602005018076T patent/DE602005018076D1/de active Active
- 2005-06-21 RU RU2007102228/04A patent/RU2383534C2/ru active
- 2005-06-21 BR BRPI0512298-8A patent/BRPI0512298A/pt not_active Application Discontinuation
- 2005-06-21 CN CN2005800195899A patent/CN1968927B/zh active Active
- 2005-06-21 TW TW094120524A patent/TWI347317B/zh active
-
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
- 2007-09-25 HK HK07110434.6A patent/HK1105121A1/xx unknown
-
2010
- 2010-02-18 HR HR20100087T patent/HRP20100087T1/hr unknown
- 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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