AR035663A1 - Clorhidrato de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano, procedimiento para su preparacion, y procedimiento de preparacion de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano - Google Patents
Clorhidrato de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano, procedimiento para su preparacion, y procedimiento de preparacion de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofuranoInfo
- Publication number
- AR035663A1 AR035663A1 ARP010105714A ARP010105714A AR035663A1 AR 035663 A1 AR035663 A1 AR 035663A1 AR P010105714 A ARP010105714 A AR P010105714A AR P010105714 A ARP010105714 A AR P010105714A AR 035663 A1 AR035663 A1 AR 035663A1
- Authority
- AR
- Argentina
- Prior art keywords
- dibutylamino
- propoxy
- nitro
- benzoyl
- hydrochloride
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Clorhidrato de 2-butil-3-(4-[3-(dibutilamino)propoxi)benzoil)-5-nitro-benzofurano de fórmula (1). Derivados benzoilos de fórmula general (2) así como su clorhidrato, en la cual R representa cloro o un grupo -OR1 en la cual R1 representa hidrógeno o un grupo alquilo C1-4 a excepción del clorhidrato de cloro-1 (di-n-butilamino-3 propoxi)-4 benzoilo. Procedimiento de preparación del compuesto de fórmula (1), en donde, en una fase orgánica constituida por uno o varios solventes elegidos entre hidrocarburos halogenados o no, se hace reaccionar 2-butil-5-nitro-benzofurano con clorhidrato del cloruro de 4-[3-(dibutilamino)propoxi]benzoilo y estos, en presencia de un máximo de 3 equivalente molares de un ácido de Lewis como catalizador, luego se hidroliza para formar el compuesto deseado que se recupera en la fase orgánica. Procedimiento de preparación de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano, en el cual se trata el clorhidrato de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano por medio de un agente básico, lo que da el compuesto deseado. Procedimiento de preparación de dronedarona y de sus sales farmacéuticamente aceptables, en la cual: a) en una fase orgánica, constituida por uno o varios solventes elegidos entre hidrocarburos halogenados o no, se hace reaccionar el 2-butil-5-nitro-benzofurano con el clorhidrato del cloruro de 4-[3-(dibutilamino)propoxi]benzoilo y esto, en presencia de un máximo de 3 equivalente molares de un ácido de Lewis como catalizador, luego se hidroliza para obtener transitoriamente y sin aislamiento, el clorhidrato 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano que se recupera en la fase orgánica y que se trata por medio de un agente básico para formar el 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano; b) se hidrogena el compuesto así obtenido en presencia de un catalizador apropiado, lo que da 5-amino-2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil-benzofurano; c) se hace reaccionar el derivado de 5-aminobenzofurano así obtenido con cloruro de metanosulfonilo o con anhídrido metanosulfónico, la reacción tiene lugar en presencia de un aceptador de ácido, lo que da dronedarona que se puede hacer reaccionar, se se lo desea, con un ácido orgánico o inorgánico para formar una sal farmacéuticamente aceptable de ese compuesto. Procedimiento de preparación del clorhidrato del cloruro de 4-[3-(dibutilamino)propoxi]benzoilo, en el cual: a) se hace reaccionar el 1-dibutilamino-3-cloro-propano con un p-hidroxibenzoato de alquilo C1-4 y esto, en presencia de un agente básico para obtener un 4-[3-(dibutilamino)propoxi]benzoato de alquilo C1-4; b) se saponifica el éster así obtenido en presencia de un hidróxido de metal alcalino, luego se trata la sal así formada, por medio de ácido clorhídrico para formar el clorhidrato del ácido 4-[3-(dibutilamino)propoxi]benzoico; y c) se trata el clorhidrato así obtenido por medio de un agente de cloración, para obtener el compuesto deseado. El compuesto de fórmula (1) es particularmente útil como intermediario para preparar 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano, a su vez, intermediario para la dronedarona. Los compuestos de fórmula (2) son particularmente útiles como intermediarios de síntesis, por ejemplo para la preparación del compuesto de fórmula (1). La dronedarona es particularmente útil en el campo cardiovascular, especialmente como agente antirrítmico.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0016069A FR2817865B1 (fr) | 2000-12-11 | 2000-12-11 | Derive aminoalkoxybenzoyle sous forme de sel, son procede de preparation et son utilisation comme intermediaire de synthese |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR035663A1 true AR035663A1 (es) | 2004-06-23 |
Family
ID=8857481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP010105714A AR035663A1 (es) | 2000-12-11 | 2001-12-10 | Clorhidrato de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano, procedimiento para su preparacion, y procedimiento de preparacion de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6846936B2 (es) |
| EP (1) | EP1351907B1 (es) |
| JP (2) | JP4437004B2 (es) |
| CN (2) | CN1295200C (es) |
| AR (1) | AR035663A1 (es) |
| AT (1) | ATE345319T1 (es) |
| AU (1) | AU2002217227A1 (es) |
| BR (1) | BR0116065B1 (es) |
| CA (1) | CA2429268C (es) |
| CZ (1) | CZ303489B6 (es) |
| DE (1) | DE60124587T2 (es) |
| DK (1) | DK1351907T3 (es) |
| ES (1) | ES2276741T3 (es) |
| FR (1) | FR2817865B1 (es) |
| HK (1) | HK1055944A1 (es) |
| HR (1) | HRP20030471B1 (es) |
| HU (1) | HUP0500981A3 (es) |
| MX (1) | MXPA03005223A (es) |
| PL (1) | PL206029B1 (es) |
| SK (1) | SK287770B6 (es) |
| WO (1) | WO2002048078A1 (es) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI356054B (en) * | 2004-03-31 | 2012-01-11 | Activus Pharma Co Ltd | Quaternary ammonium compound, producing method the |
| GB0719180D0 (en) * | 2007-10-02 | 2007-11-14 | Cambrex Karlskoga Ab | New process |
| FR2930149B1 (fr) * | 2008-04-17 | 2011-02-18 | Sanofi Aventis | Association de dronedarone avec au moins un diuretique, son application en therapeutique |
| US8410167B2 (en) * | 2008-04-17 | 2013-04-02 | Sanofi | Use of dronedarone for the preparation of a medicament for use in the prevention of cardiovascular hospitalization or of mortality |
| EP2116239A1 (en) * | 2008-04-29 | 2009-11-11 | Sanofi-Aventis | Method for managing the risks associated with an increase in serum creatinine during dronedarone treatment |
| EP2246341A1 (en) | 2009-01-23 | 2010-11-03 | Lonza Ltd. | Process for preparing 2-Alkyl-3-aroyl-5-nitro-benzofurans |
| EP2417099B1 (en) * | 2009-04-08 | 2015-12-23 | Cambrex Karlskoga AB | New process for preparing hydroxylamines and medicaments |
| UY32656A (es) | 2009-05-27 | 2010-12-31 | Sanofi Aventis | Procedimiento para producir benzofuranos |
| TW201111354A (en) | 2009-05-27 | 2011-04-01 | Sanofi Aventis | Process for the production of Dronedarone intermediates |
| CN101993427B (zh) * | 2009-08-26 | 2012-10-10 | 成都伊诺达博医药科技有限公司 | 一种制备决奈达隆的方法 |
| HUP0900759A2 (en) | 2009-12-08 | 2011-11-28 | Sanofi Aventis | Novel process for producing dronedarone |
| HUP1000010A2 (en) | 2010-01-08 | 2011-11-28 | Sanofi Sa | Process for producing dronedarone |
| IT1398317B1 (it) * | 2010-02-23 | 2013-02-22 | Chimico Internaz Spa Lab | Nuovo procedimento per la preparazione del dronedarone. |
| FR2957079B1 (fr) | 2010-03-02 | 2012-07-27 | Sanofi Aventis | Procede de synthese de derives de cetobenzofurane |
| EP2371824A1 (en) * | 2010-03-08 | 2011-10-05 | Ratiopharm GmbH | Crystalline dronedarone salts |
| FR2958290B1 (fr) | 2010-03-30 | 2012-10-19 | Sanofi Aventis | Procede de preparation de derives de sulfonamido-benzofurane |
| FR2958291B1 (fr) | 2010-04-01 | 2013-07-05 | Sanofi Aventis | Procede de preparation de derives d'amino-benzofurane |
| HUP1000330A2 (en) * | 2010-06-18 | 2011-12-28 | Sanofi Sa | Process for the preparation of dronedarone and the novel intermediates |
| US8602215B2 (en) | 2010-06-30 | 2013-12-10 | Sanofi | Methods for reducing the risk of an adverse dronedarone/beta-blockers interaction in a patient suffering from atrial fibrillation |
| WO2012004658A2 (en) | 2010-07-09 | 2012-01-12 | Frichem Private Limited | Process for preparation of n-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]-5-benzofuranyl]methanesulfonamide, acid addition salts and product thereof |
| WO2012007959A1 (en) * | 2010-07-16 | 2012-01-19 | Glenmark Generics Limited | Process for preparing dronedarone |
| FR2962731B1 (fr) | 2010-07-19 | 2012-08-17 | Sanofi Aventis | Procede de preparation de derives d'amino-benzoyl-benzofurane |
| FR2963006B1 (fr) | 2010-07-21 | 2013-03-15 | Sanofi Aventis | Procede de preparation de derives de nitro-benzofurane |
| HUP1000386A2 (en) | 2010-07-22 | 2012-05-29 | Sanofi Sa | Novel process for producing dronedarone |
| WO2012032545A1 (en) * | 2010-09-08 | 2012-03-15 | Cadila Healthcare Limited | Processes for preparing dronedarone and its intermediates |
| EP2447256A1 (en) * | 2010-10-21 | 2012-05-02 | Laboratorios Lesvi, S.L. | Process for obtaining dronedarone |
| CN102070578B (zh) * | 2011-01-19 | 2015-10-14 | 上海医药工业研究院 | 2-正丁基-3-(4-(3-二正丁基氨基丙氧基)苯甲酰基)-5-烷酰基氨基苯并呋喃的制备方法 |
| CN102070581B (zh) * | 2011-01-19 | 2015-11-25 | 上海医药工业研究院 | 2-正丁基-3-(4-(3-二正丁基氨基丙氧基)苯甲酰基)-5-氨基苯并呋喃的制备 |
| CN102070579B (zh) * | 2011-01-19 | 2016-03-09 | 上海医药工业研究院 | 2-正丁基-3-(4-取代丙氧基苯甲酰基)-5-取代氨基苯并呋喃的制备方法 |
| CN102070580B (zh) * | 2011-01-19 | 2015-05-20 | 上海医药工业研究院 | 2-正丁基-3-(4-(3-二正丁基氨基丙氧基)苯甲酰基)-5-取代氨基苯并呋喃的制备 |
| WO2012120544A2 (en) | 2011-03-10 | 2012-09-13 | Sun Pharmaceutical Industries Ltd. | PROCESS FOR N-[2-n-BUTYL-3-[4-[3-(DI-n-BUTYLAMINO) PROPOXY]ENZOYL]BENZOFURAN-5-YL]METHANESULFONAMIDE HYDROCHLORIDE |
| CN102690249B (zh) * | 2011-03-22 | 2014-09-17 | 江苏康缘药业股份有限公司 | 一种决奈达隆的制备方法 |
| HUP1100165A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Process for preparation of dronedarone by n-butylation |
| HUP1100166A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Reductive amination process for preparation of dronedarone using amine intermediary compound |
| HUP1100167A2 (en) * | 2011-03-29 | 2012-11-28 | Sanofi Sa | Process for preparation of dronedarone by mesylation |
| WO2013014479A1 (en) | 2011-07-26 | 2013-01-31 | Sanofi | Reductive animation process for preparation of dronedarone using aldehyde intermediary compound |
| WO2013014478A1 (en) | 2011-07-26 | 2013-01-31 | Sanofi | Reductive amination process for preparation of dronedarone using carboxyl intermediary compound |
| WO2013014480A1 (en) | 2011-07-26 | 2013-01-31 | Sanofi | Process for preparation of dronedarone using amide intermediary compound |
| ITMI20111672A1 (it) * | 2011-09-16 | 2013-03-17 | Olon Spa | Metodo efficiente per la preparazione di dronedarone cloridrato |
| FR2983198B1 (fr) | 2011-11-29 | 2013-11-15 | Sanofi Sa | Procede de preparation de derives de 5-amino-benzoyl-benzofurane |
| EP2617718A1 (en) | 2012-01-20 | 2013-07-24 | Sanofi | Process for preparation of dronedarone by the use of dibutylaminopropanol reagent |
| US9221778B2 (en) | 2012-02-13 | 2015-12-29 | Sanofi | Process for preparation of dronedarone by removal of hydroxyl group |
| US9249119B2 (en) | 2012-02-14 | 2016-02-02 | Sanofi | Process for the preparation of dronedarone by oxidation of a sulphenyl group |
| US9382223B2 (en) | 2012-02-22 | 2016-07-05 | Sanofi | Process for preparation of dronedarone by oxidation of a hydroxyl group |
| US9238636B2 (en) | 2012-05-31 | 2016-01-19 | Sanofi | Process for preparation of dronedarone by Grignard reaction |
| CN102675267B (zh) * | 2012-06-07 | 2015-05-13 | 济南富创医药科技有限公司 | 盐酸决奈达隆及其中间体的制备方法 |
| CN108164411B (zh) * | 2017-12-29 | 2021-03-02 | 苏州汶颢微流控技术股份有限公司 | 基于微反应器制备对庚氧基苯甲酸的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3947470A (en) * | 1974-06-20 | 1976-03-30 | Smithkline Corporation | Substituted benzofurans and benzothiophenes |
| US4024273A (en) * | 1974-06-20 | 1977-05-17 | Smithkline Corporation | Coronary vasodilator and anti-anginal compositions comprising substituted benzofurans and benzothiophenes and methods of producing coronary vasodilation and anti-anginal activity |
| FR2665444B1 (fr) * | 1990-08-06 | 1992-11-27 | Sanofi Sa | Derives d'amino-benzofuranne, benzothiophene ou indole, leur procede de preparation ainsi que les compositions les contenant. |
| US5631369A (en) * | 1994-08-31 | 1997-05-20 | Eli Lilly And Company | Process for preparing benzoic acid derivative intermediates and benzothiophene pharmaceutical agents |
| US5731436A (en) * | 1994-08-31 | 1998-03-24 | Eli Lilly And Company | Process for preparing benzoic acid derivative intermediates and benzothiophene pharmaceutical agents |
-
2000
- 2000-12-11 FR FR0016069A patent/FR2817865B1/fr not_active Expired - Fee Related
-
2001
- 2001-12-10 PL PL364774A patent/PL206029B1/pl unknown
- 2001-12-10 AT AT01270513T patent/ATE345319T1/de active
- 2001-12-10 AU AU2002217227A patent/AU2002217227A1/en not_active Abandoned
- 2001-12-10 HU HU0500981A patent/HUP0500981A3/hu unknown
- 2001-12-10 JP JP2002549615A patent/JP4437004B2/ja not_active Expired - Fee Related
- 2001-12-10 CA CA2429268A patent/CA2429268C/fr not_active Expired - Fee Related
- 2001-12-10 CZ CZ20031611A patent/CZ303489B6/cs not_active IP Right Cessation
- 2001-12-10 DK DK01270513T patent/DK1351907T3/da active
- 2001-12-10 ES ES01270513T patent/ES2276741T3/es not_active Expired - Lifetime
- 2001-12-10 WO PCT/FR2001/003900 patent/WO2002048078A1/fr active IP Right Grant
- 2001-12-10 AR ARP010105714A patent/AR035663A1/es not_active Application Discontinuation
- 2001-12-10 CN CNB018203787A patent/CN1295200C/zh not_active Expired - Fee Related
- 2001-12-10 US US10/433,639 patent/US6846936B2/en not_active Expired - Lifetime
- 2001-12-10 CN CNB200510108930XA patent/CN100371314C/zh not_active Expired - Fee Related
- 2001-12-10 SK SK727-2003A patent/SK287770B6/sk not_active IP Right Cessation
- 2001-12-10 BR BRPI0116065-6A patent/BR0116065B1/pt not_active IP Right Cessation
- 2001-12-10 DE DE60124587T patent/DE60124587T2/de not_active Expired - Lifetime
- 2001-12-10 EP EP01270513A patent/EP1351907B1/fr not_active Expired - Lifetime
- 2001-12-10 MX MXPA03005223A patent/MXPA03005223A/es active IP Right Grant
-
2003
- 2003-06-11 HR HR20030471A patent/HRP20030471B1/xx not_active IP Right Cessation
- 2003-11-13 HK HK03108257A patent/HK1055944A1/xx not_active IP Right Cessation
-
2008
- 2008-07-11 JP JP2008181486A patent/JP2009024007A/ja active Pending
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