PE20050211A1 - Procedimiento para preparar oxi-(1h)-quinolin-2-onas 5-(alfa-haloacetil)-8-sustituidas - Google Patents
Procedimiento para preparar oxi-(1h)-quinolin-2-onas 5-(alfa-haloacetil)-8-sustituidasInfo
- Publication number
- PE20050211A1 PE20050211A1 PE2004000341A PE2004000341A PE20050211A1 PE 20050211 A1 PE20050211 A1 PE 20050211A1 PE 2004000341 A PE2004000341 A PE 2004000341A PE 2004000341 A PE2004000341 A PE 2004000341A PE 20050211 A1 PE20050211 A1 PE 20050211A1
- Authority
- PE
- Peru
- Prior art keywords
- quinolin
- ona
- acetyl
- hydroxy
- oxy
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 239000002841 Lewis acid Substances 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 150000007517 lewis acids Chemical class 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- -1 BORON TRIFLORIDE Chemical class 0.000 abstract 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 229910052796 boron Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 150000004693 imidazolium salts Chemical class 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
-
- 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
-
- 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
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pulmonology (AREA)
- Materials Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Quinoline Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
QUE COMPRENDE: a) HACER REACCIONAR EN PRESENCIA DE UN HALOGENURO ALCALINO O SAL DE IMIDAZOLIO, ENTRE OTROS: i) 8-HIDROXI-(1H)-QUINOLIN-2-ONA CON DE 1 A 1,5 EQUIVALENTES MOLARES DE UN AGENTE DE ACILACION, TAL COMO ANHIDRIDO ACETICO O CLORURO DE ACETILO, Y DE 3 A 5 EQUIVALENTES MOLARES DE UN ACIDO LEWIS, TAL COMO TRIFLORURO DE BORO, CLORURO DE ALUMINIO O TETRACLORURO DE TITANIO, PARA FORMAR 5-ACETIL-8-HIDROXI-(1H)-QUINOLIN-2-ONA; o ii) 8-HIDROXI-(1H)-QUINOLIN-2-ONA CON UN AGENTE DE ACILACION PARA FORMAR 8-ACETOXI-(1H)-QUINOLIN-2-ONA, Y TRATAR, IN SITU, LA 8-ACETOXI-(1H)-QUINOLIN-2-ONA CON UN ACIDO LEWIS PARA FORMAR LA 5-ACETIL-8-HIDROXI-(1H)-QUINOLIN-2-ONA; o iii) 8-ACETOXI-(1H)-QUINOLIN-2-ONA CON ACIDO LEWIS PARA FORMAR 5-ACETIL-8-HIDROXI-(1H)-QUINOLIN-2-ONA; b) HACER REACCIONAR LA 5-ACETIL-8-HIDROXI-(1H)-QUINOLIN-2-ONA PREPARADA EN (a) CON UN COMPUESTO QUE TIENE LA FORMULA RL EN PRESENCIA DE UNA BASE Y UN SOLVENTE PARA FORMAR OXI-(1H)-QUINOLIN-2-ONA 5-ACETIL-8-SUBSTITUIDA, EN DONDE R ES UN GRUPO PROTECTOR Y L ES UN GRUPO SALIENTE; Y, c) HACER REACCIONAR LA OXI-(1H)-QUINOLIN-2-ONA 5 ACETIL-8-SUBSTITUIDA CON UN AGENTE DE HALOGENACION, TAL COMO DICLOROYODATO DE BENCILTRIMETILAMONIO, EN PRESENCIA DE UN SOLVENTE PARA FORMAR OXI-(1H)-QUINOLIN-2-ONA 5-(ALFA-HALOACETIL)-8-SUBSTITUIDA. EL SOLVENTE ES, ENTRE OTROS, EN (a) HIDROCARBURO ALIFATICO C6-C12, EN (b) ACETONA, Y EN (c) ACIDO ACETICO. LA TEMPERATURA EN (a) ES DE 0°C A 160°C, EN (b) ES DE 20°C A 90°C, Y EN (c) ES DE 10°C A 160°C
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45972403P | 2003-04-02 | 2003-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20050211A1 true PE20050211A1 (es) | 2005-04-27 |
Family
ID=33131902
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2010000225A PE20100399A1 (es) | 2003-04-02 | 2004-03-31 | Procedimiento para preparar oxi-(1h)-quinolin-2-onas 5-(alfa-haloacetil)-8-sustituidas |
| PE2004000341A PE20050211A1 (es) | 2003-04-02 | 2004-03-31 | Procedimiento para preparar oxi-(1h)-quinolin-2-onas 5-(alfa-haloacetil)-8-sustituidas |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2010000225A PE20100399A1 (es) | 2003-04-02 | 2004-03-31 | Procedimiento para preparar oxi-(1h)-quinolin-2-onas 5-(alfa-haloacetil)-8-sustituidas |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US7605267B2 (es) |
| EP (1) | EP1613599B8 (es) |
| JP (1) | JP4726778B2 (es) |
| KR (1) | KR101073740B1 (es) |
| CN (1) | CN1774423A (es) |
| AR (2) | AR043825A1 (es) |
| AT (1) | ATE491690T1 (es) |
| AU (1) | AU2004226212B2 (es) |
| BR (1) | BRPI0409154B1 (es) |
| CA (1) | CA2520990C (es) |
| CL (1) | CL2004000706A1 (es) |
| CO (1) | CO5700779A2 (es) |
| CY (1) | CY1111515T1 (es) |
| DE (1) | DE602004030553D1 (es) |
| DK (1) | DK1613599T3 (es) |
| EC (1) | ECSP056059A (es) |
| ES (1) | ES2358193T3 (es) |
| HR (1) | HRP20110184T1 (es) |
| IL (1) | IL171053A (es) |
| IS (1) | IS2800B (es) |
| MA (1) | MA27761A1 (es) |
| MX (1) | MXPA05010616A (es) |
| MY (1) | MY141871A (es) |
| NO (1) | NO331980B1 (es) |
| NZ (1) | NZ542623A (es) |
| PE (2) | PE20100399A1 (es) |
| PL (1) | PL1613599T3 (es) |
| PT (1) | PT1613599E (es) |
| RU (1) | RU2339621C2 (es) |
| SI (1) | SI1613599T1 (es) |
| TN (1) | TNSN05245A1 (es) |
| TW (1) | TWI324151B (es) |
| WO (1) | WO2004087668A1 (es) |
| ZA (1) | ZA200507603B (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| GB0413960D0 (en) * | 2004-06-22 | 2004-07-28 | Novartis Ag | Organic compounds |
| US8198450B2 (en) | 2006-06-30 | 2012-06-12 | Novartis Ag | Quinolinone derivatives and their pharmaceutical compositions |
| WO2013132514A2 (en) * | 2012-03-09 | 2013-09-12 | Rao Davuluri Ramamohan | A novel process for the preparation of (r)-5-[2-[(5, 6-diethyl-2, 3-dihydro-1h-inden-2-yl) amino]-1-hydroxyethyl]-8-hydroxy quinolin-2(1h)-one |
| CN102633717B (zh) * | 2012-03-30 | 2013-11-20 | 西南大学 | N-乙酰-喹啉-2(1h)酮类化合物及其制备方法和应用 |
| 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 |
| 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) |
| US9682935B2 (en) | 2014-01-09 | 2017-06-20 | Davuluri Ramamohan Rao | Process for preparation of indacaterol or its pharmaceutically acceptable salts |
| 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 |
| CN107531636B (zh) * | 2015-04-09 | 2022-11-25 | 正大天晴药业集团股份有限公司 | 茚达特罗或其盐的制备方法 |
| 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 |
| CN108264483A (zh) * | 2016-12-31 | 2018-07-10 | 天津金耀集团有限公司 | 一种马来酸茚达特罗的制备方法 |
| CN109721534B (zh) * | 2018-09-25 | 2022-05-20 | 四川海思科制药有限公司 | 一种马来酸茚达特罗中间体及其制备方法和用途 |
| CN114751857A (zh) * | 2022-04-29 | 2022-07-15 | 梯尔希（南京）药物研发有限公司 | 一种茚达特罗杂质的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS539228B2 (es) * | 1974-01-31 | 1978-04-04 | ||
| CA1164459A (en) * | 1980-11-11 | 1984-03-27 | Yung-Hsiung Yang | Process for preparing (imidazo¬1,2-a|pyridine- 2-yl)-carbostyril or -3,4-dihydrocarbostyryl derivatives |
| JPS5896022A (ja) * | 1981-11-30 | 1983-06-07 | Otsuka Pharmaceut Co Ltd | 強心剤 |
| ES519384A0 (es) * | 1983-01-28 | 1984-03-16 | Espanola Farma Therapeut | Procedimiento para la obtencion de un compuesto derivado de la 2-quinolinona. |
| ES8605239A1 (es) * | 1985-12-04 | 1986-03-16 | Astur Pharma | Un procedimiento para la preparacion de quinolonas sustitui-das |
| US4894219A (en) * | 1988-03-29 | 1990-01-16 | University Of Florida | Beta-agonist carbostyril derivatives, assay method and pharmacological composition |
| GB9405019D0 (en) | 1994-03-15 | 1994-04-27 | Smithkline Beecham Plc | Novel compounds |
| RU2170730C2 (ru) * | 1996-05-20 | 2001-07-20 | Дарвин Дискавери Лимитед | Хинолиновые карбоксамиды и фармацевтическая композиция на их основе |
| GB9913083D0 (en) * | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| GB0029562D0 (en) * | 2000-12-04 | 2001-01-17 | Novartis Ag | Organic compounds |
| US6653323B2 (en) * | 2001-11-13 | 2003-11-25 | Theravance, Inc. | Aryl aniline β2 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 |
-
2004
- 2004-03-31 TW TW093108942A patent/TWI324151B/zh not_active IP Right Cessation
- 2004-03-31 PE PE2010000225A patent/PE20100399A1/es not_active Application Discontinuation
- 2004-03-31 PE PE2004000341A patent/PE20050211A1/es not_active Application Discontinuation
- 2004-04-01 BR BRPI0409154-0B1A patent/BRPI0409154B1/pt not_active IP Right Cessation
- 2004-04-01 RU RU2005133664/04A patent/RU2339621C2/ru active
- 2004-04-01 ES ES04725035T patent/ES2358193T3/es not_active Expired - Lifetime
- 2004-04-01 MX MXPA05010616A patent/MXPA05010616A/es active IP Right Grant
- 2004-04-01 PL PL04725035T patent/PL1613599T3/pl unknown
- 2004-04-01 US US10/550,621 patent/US7605267B2/en active Active
- 2004-04-01 AU AU2004226212A patent/AU2004226212B2/en not_active Expired
- 2004-04-01 SI SI200431618T patent/SI1613599T1/sl unknown
- 2004-04-01 WO PCT/EP2004/003479 patent/WO2004087668A1/en not_active Ceased
- 2004-04-01 AR ARP040101105A patent/AR043825A1/es not_active Application Discontinuation
- 2004-04-01 CL CL200400706A patent/CL2004000706A1/es unknown
- 2004-04-01 HR HR20110184T patent/HRP20110184T1/hr unknown
- 2004-04-01 AT AT04725035T patent/ATE491690T1/de active
- 2004-04-01 CA CA2520990A patent/CA2520990C/en not_active Expired - Lifetime
- 2004-04-01 JP JP2006504953A patent/JP4726778B2/ja not_active Expired - Lifetime
- 2004-04-01 PT PT04725035T patent/PT1613599E/pt unknown
- 2004-04-01 DE DE602004030553T patent/DE602004030553D1/de not_active Expired - Lifetime
- 2004-04-01 DK DK04725035.2T patent/DK1613599T3/da active
- 2004-04-01 NZ NZ542623A patent/NZ542623A/en not_active IP Right Cessation
- 2004-04-01 MY MYPI20041213A patent/MY141871A/en unknown
- 2004-04-01 CN CNA2004800089560A patent/CN1774423A/zh active Pending
- 2004-04-01 EP EP04725035A patent/EP1613599B8/en not_active Expired - Lifetime
-
2005
- 2005-09-20 ZA ZA200507603A patent/ZA200507603B/en unknown
- 2005-09-22 IL IL171053A patent/IL171053A/en active IP Right Grant
- 2005-09-29 EC EC2005006059A patent/ECSP056059A/es unknown
- 2005-09-30 TN TNP2005000245A patent/TNSN05245A1/en unknown
- 2005-09-30 KR KR1020057018750A patent/KR101073740B1/ko not_active Expired - Lifetime
- 2005-10-11 MA MA28545A patent/MA27761A1/fr unknown
- 2005-10-12 CO CO05104250A patent/CO5700779A2/es active IP Right Grant
- 2005-10-27 IS IS8095A patent/IS2800B/is unknown
- 2005-11-01 NO NO20055099A patent/NO331980B1/no unknown
-
2011
- 2011-03-14 CY CY20111100284T patent/CY1111515T1/el unknown
-
2016
- 2016-01-25 AR ARP160100188A patent/AR103508A2/es unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC | Refusal | ||
| FG | Grant, registration | ||
| FD | Application declared void or lapsed |