PE20060304A1 - Procedimiento para preparar sales de oxi-5-[(r)-2-halo-1-hidroxi-etil]-(1h)-quinolin-2-onas 8 sustituidas - Google Patents
Procedimiento para preparar sales de oxi-5-[(r)-2-halo-1-hidroxi-etil]-(1h)-quinolin-2-onas 8 sustituidasInfo
- Publication number
- PE20060304A1 PE20060304A1 PE2005000704A PE2005000704A PE20060304A1 PE 20060304 A1 PE20060304 A1 PE 20060304A1 PE 2005000704 A PE2005000704 A PE 2005000704A PE 2005000704 A PE2005000704 A PE 2005000704A PE 20060304 A1 PE20060304 A1 PE 20060304A1
- Authority
- PE
- Peru
- Prior art keywords
- quinolin
- hydroxy
- ona
- ethyl
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical class C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 title 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 abstract 1
- KGVIJLMNQNSQHB-UHFFFAOYSA-N 5,6-diethyl-2,3-dihydro-1h-inden-2-amine Chemical compound C1=C(CC)C(CC)=CC2=C1CC(N)C2 KGVIJLMNQNSQHB-UHFFFAOYSA-N 0.000 abstract 1
- 108060003345 Adrenergic Receptor Proteins 0.000 abstract 1
- 102000017910 Adrenergic receptor Human genes 0.000 abstract 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract 1
- 239000000556 agonist Substances 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 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)
Abstract
QUE CONSISTE EN: A) REACCIONAR OXI-(1H)-QUINOLIN-2-ONA-5-(A-HALOACETIL)-8-SUSTITUIDA CON UN AGENTE REDUCTOR TAL COMO 2-PROPANOL, 3-PENTANOL, ACIDO FORMICO, EN PRESENCIA DE UN AGENTE QUIRAL DE FORMULA I, II, Y UNA BASE TAL COMO ETOXIDO, NaOH, K2CO3, ENTRE OTROS, PARA FORMAR 8-(OXISUTITUIDA)-5-((R)-2-HALO-1-HIDROXI-ETIL)-(1H)-QUINOLIN-2-ONA; DONDE M ES Ru, Rh, Fe, ENTRE OTROS; L ES ARILO C6-C24, ENTRE OTROS; X ES H, HALOGENO; R1 ES FENILO, CRISENILO, PERILENILO, ENTRE OTROS; R2 Y R3 SON FENILO; B) TRATAR LA SOLUCION CON UNA BASE EN PRESENCIA DE UN SOLVENTE PARA FORMAR OXI-5-(R)-OXIRANIL-(1H)-QUINOLIN-2-ONA 8 SUSTITUIDA; C) HACER REACCIONAR LA SOLUCION CON 2-AMINO-(5,6-DIETIL)-INDANO PARA FORMAR UNA MEZCLA DE REACCION D) TRATAR LA MEZCLA OBTENIDA, CON UN ACIDO EN PRESENCIA DE UN SOLVENTE PARA FORMAR UNA SAL; E) AISLAR Y CRISTALIZAR LA SAL; F) REMOVER EL GRUPO PROTECTOR Y TRATARLA CON UN ACIDO EN PRESENCIA DE UN SOLVENTE. POR ESTE PROCESO SE OBTIENE: SALES DE [(R)-2-(5,6-DIETIL-INDAN-2-ILAMINO)-1-HIDROXI-ETIL]-8-HIDROXI-(1H)-QUINOLIN-2-ONA. DICHOS COMPUESTOS SON AGONISTAS DEL ADRENOCEPTOR B-SELECTIVOS, UTILES EN EL TRATAMIENTO DE ASMA Y ENFERMEDAD PULMONAR OBSTRUCTIVA CRONICA
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 |
|---|---|
| PE20060304A1 true PE20060304A1 (es) | 2006-05-19 |
Family
ID=32799952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2005000704A PE20060304A1 (es) | 2004-06-22 | 2005-06-20 | Procedimiento para preparar sales de oxi-5-[(r)-2-halo-1-hidroxi-etil]-(1h)-quinolin-2-onas 8 sustituidas |
Country Status (32)
| 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) |
| 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 (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ573292A (en) | 2006-06-30 | 2011-03-31 | 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 |
| DK2593452T3 (en) | 2010-07-14 | 2017-04-24 | Novartis Ag | Heterocyclic compounds as IP receptor agonists |
| 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 |
| US20140378463A1 (en) | 2012-01-13 | 2014-12-25 | Novartis Ag | IP receptor agonist heterocyclic compounds |
| 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 |
| WO2013105061A1 (en) | 2012-01-13 | 2013-07-18 | Novartis Ag | Fused dihydropyrido [2,3 -b] pyrazines as ip receptor agonists for the treatment of pulmonary arterial hypertension (pah) and related disorders |
| WO2013105066A1 (en) | 2012-01-13 | 2013-07-18 | Novartis Ag | Salts of an ip receptor agonist |
| US9115129B2 (en) | 2012-01-13 | 2015-08-25 | Novartis Ag | Substituted pyrido[2,3-B]pyrazines as IP receptor agonists |
| TW201335160A (zh) | 2012-01-13 | 2013-09-01 | Novartis Ag | Ｉｐ受體激動劑之雜環化合物 |
| 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 |
| WO2014044288A1 (en) | 2012-09-21 | 2014-03-27 | Crystal Pharma Sa | Methods for the preparation of indacaterol and pharmaceutically acceptable salts thereof |
| EP2897937B1 (en) | 2012-09-21 | 2017-12-06 | Crystal Pharma S.A.U | Process for the preparation of indacaterol and intermediates thereof |
| CN104968656B (zh) | 2012-12-19 | 2017-08-11 | 诺华股份有限公司 | 自分泌运动因子抑制剂 |
| JP2016507582A (ja) | 2013-02-13 | 2016-03-10 | ノバルティス アーゲー | Ｉｐ受容体アゴニスト複素環式化合物 |
| 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) |
| ES2626829T3 (es) | 2013-03-27 | 2017-07-26 | Laboratorios Lesvi, S.L. | Procedimiento para la fabricación de (R)-5[2-(5,6-dietil-indan-2-ilamino)-1-hidroxietil]-8-hidroxi-(1H)-quinolin-2-ona |
| EP3022201A1 (en) | 2013-07-18 | 2016-05-25 | Novartis AG | Autotaxin inhibitors |
| EA035256B1 (ru) | 2013-07-18 | 2020-05-21 | Новартис Аг | Ингибиторы аутотаксинов, содержащие гетероарил-бензил-амидное ядро |
| US9682935B2 (en) | 2014-01-09 | 2017-06-20 | Davuluri Ramamohan Rao | 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 |
| WO2015162558A1 (en) | 2014-04-24 | 2015-10-29 | 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 |
| EP3347345B1 (en) | 2015-09-29 | 2019-07-31 | Inke, S.A. | 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 |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9405019D0 (en) * | 1994-03-15 | 1994-04-27 | Smithkline Beecham Plc | Novel compounds |
| DE69738949D1 (de) * | 1996-05-20 | 2008-10-09 | Darwin Discovery Ltd | Chinolincarboxamide als tnf-inhibitoren und als pde-iv inhibitoren |
| 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 |
| TWI324151B (en) * | 2003-04-02 | 2010-05-01 | Novartis Ag | Process for the preparation of 5-(haloacetyl)-8-substituted oxy-(1h)-quinolin-2-ones |
-
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 BR BRPI0512298-8A patent/BRPI0512298A/pt not_active Application Discontinuation
- 2005-06-21 AU AU2005254698A patent/AU2005254698B2/en not_active Expired
- 2005-06-21 CA CA2566388A patent/CA2566388C/en not_active Expired - Lifetime
- 2005-06-21 SI SI200530921T patent/SI1791820T1/sl unknown
- 2005-06-21 TW TW094120524A patent/TWI347317B/zh active
- 2005-06-21 JP JP2007517180A patent/JP5064214B2/ja not_active Expired - Lifetime
- 2005-06-21 RU RU2007102228/04A patent/RU2383534C2/ru active
- 2005-06-21 MX MXPA06014695A patent/MXPA06014695A/es active IP Right Grant
- 2005-06-21 ES ES05770221T patent/ES2337273T3/es not_active Expired - Lifetime
- 2005-06-21 AT AT05770221T patent/ATE450512T1/de active
- 2005-06-21 DE DE602005018076T patent/DE602005018076D1/de not_active Expired - Lifetime
- 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 KR KR1020067026958A patent/KR101179302B1/ko not_active Expired - Lifetime
- 2005-06-21 DK DK05770221.9T patent/DK1791820T3/da active
- 2005-06-21 US US11/569,140 patent/US20090054653A1/en not_active Abandoned
- 2005-06-21 CN CN2005800195899A patent/CN1968927B/zh not_active Expired - Lifetime
- 2005-06-21 WO PCT/EP2005/006686 patent/WO2005123684A2/en not_active Ceased
- 2005-06-21 PL PL05770221T patent/PL1791820T3/pl unknown
- 2005-06-21 HR HR20100087T patent/HRP20100087T1/hr unknown
- 2005-06-21 PT PT05770221T patent/PT1791820E/pt unknown
-
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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