JP2010540608A5 - - Google Patents
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- Publication number
- JP2010540608A5 JP2010540608A5 JP2010527524A JP2010527524A JP2010540608A5 JP 2010540608 A5 JP2010540608 A5 JP 2010540608A5 JP 2010527524 A JP2010527524 A JP 2010527524A JP 2010527524 A JP2010527524 A JP 2010527524A JP 2010540608 A5 JP2010540608 A5 JP 2010540608A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- salt
- reaction
- dronedarone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 40
- 150000001875 compounds Chemical class 0.000 claims 27
- 238000006243 chemical reaction Methods 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- ZQTNQVWKHCQYLQ-UHFFFAOYSA-N dronedarone Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C(NS(C)(=O)=O)C=C12 ZQTNQVWKHCQYLQ-UHFFFAOYSA-N 0.000 claims 11
- 229960002084 dronedarone Drugs 0.000 claims 11
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 7
- 238000002360 preparation method Methods 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- ZJZKLBXEGZKOBW-UHFFFAOYSA-N (2-butyl-5-nitro-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone Chemical compound CCCCC=1OC2=CC=C([N+]([O-])=O)C=C2C=1C(=O)C1=CC=C(O)C=C1 ZJZKLBXEGZKOBW-UHFFFAOYSA-N 0.000 claims 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 238000005580 one pot reaction Methods 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- WYALRXZJYXWYGR-UHFFFAOYSA-N (2-butyl-5-nitro-1-benzofuran-3-yl)-(4-methoxyphenyl)methanone Chemical compound CCCCC=1OC2=CC=C([N+]([O-])=O)C=C2C=1C(=O)C1=CC=C(OC)C=C1 WYALRXZJYXWYGR-UHFFFAOYSA-N 0.000 claims 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000011260 aqueous acid Substances 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- -1 methylsulfonylamino Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229920001983 poloxamer Polymers 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0719180.2A GB0719180D0 (en) | 2007-10-02 | 2007-10-02 | New process |
| GB0719180.2 | 2007-10-02 | ||
| PCT/GB2008/003341 WO2009044143A2 (en) | 2007-10-02 | 2008-10-02 | Process for preparing benzofurans |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014115816A Division JP5943965B2 (ja) | 2007-10-02 | 2014-06-04 | ベンゾフラン類を製造するための工程 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010540608A JP2010540608A (ja) | 2010-12-24 |
| JP2010540608A5 true JP2010540608A5 (enExample) | 2011-11-10 |
| JP5577252B2 JP5577252B2 (ja) | 2014-08-20 |
Family
ID=38738973
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010527524A Expired - Fee Related JP5577252B2 (ja) | 2007-10-02 | 2008-10-02 | ベンゾフラン類を製造するための工程 |
| JP2014115816A Expired - Fee Related JP5943965B2 (ja) | 2007-10-02 | 2014-06-04 | ベンゾフラン類を製造するための工程 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014115816A Expired - Fee Related JP5943965B2 (ja) | 2007-10-02 | 2014-06-04 | ベンゾフラン類を製造するための工程 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8519165B2 (enExample) |
| EP (3) | EP2200993B1 (enExample) |
| JP (2) | JP5577252B2 (enExample) |
| CN (3) | CN103342633B (enExample) |
| BR (1) | BRPI0817423A2 (enExample) |
| ES (3) | ES2589011T3 (enExample) |
| GB (1) | GB0719180D0 (enExample) |
| PL (3) | PL2388256T3 (enExample) |
| WO (1) | WO2009044143A2 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0719180D0 (en) | 2007-10-02 | 2007-11-14 | Cambrex Karlskoga Ab | New process |
| EP2684564A1 (en) | 2008-04-17 | 2014-01-15 | Sanofi | Use of dronedarone for the preparation of a medicament for use in the prevention of cardiovascular hospitalization or in the prevention of atrial fibrillation |
| JP5654994B2 (ja) * | 2008-10-02 | 2015-01-14 | カンブレックス カルルスクーガ アクチ ボラケットＣａｍｂｒｅｘ Ｋａｒｌｓｋｏｇａ Ａｂ | ジケトン及び薬剤を製造するための新しいプロセス |
| CN102171199A (zh) * | 2008-10-10 | 2011-08-31 | 隆萨有限公司 | 制备2-烷基-3-芳酰基-5-硝基-苯并呋喃类的方法 |
| CN102239414A (zh) | 2008-12-04 | 2011-11-09 | 赛诺菲-安万特 | 牵涉血红素结合蛋白1的方法和用途 |
| US9101876B2 (en) | 2009-02-25 | 2015-08-11 | Applied Hybrid Energy Pty Ltd. | Carbon capture |
| JP5788381B2 (ja) * | 2009-04-08 | 2015-09-30 | カンブレックス カルルスクーガ アクチ ボラケットＣａｍｂｒｅｘ Ｋａｒｌｓｋｏｇａ Ａｂ | ヒドロキシルアミンおよび薬剤を調製するための新規のプロセス |
| UY32657A (es) * | 2009-05-27 | 2010-12-31 | Sanofi Aventis | Procedimiento para la fabricación de productos intermedios de dronedarona |
| UY32656A (es) | 2009-05-27 | 2010-12-31 | Sanofi Aventis | Procedimiento para producir benzofuranos |
| 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 |
| FR2958290B1 (fr) | 2010-03-30 | 2012-10-19 | Sanofi Aventis | Procede de preparation de derives de sulfonamido-benzofurane |
| HUP1000330A2 (en) | 2010-06-18 | 2011-12-28 | Sanofi Sa | Process for the preparation of dronedarone and the novel intermediates |
| US20120005128A1 (en) * | 2010-06-29 | 2012-01-05 | Sanofi | Methods for reducing the risk of an adverse dronedarone / calcium channel blockers interaction in a patient suffering from atrial fibrilation |
| 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 |
| 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 |
| EP2452938A1 (en) | 2010-11-12 | 2012-05-16 | LEK Pharmaceuticals d.d. | Process for the preparation of 3-aroyl-5-aminobenzofuran derivatives |
| 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 |
| CN102070577B (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-取代氨基苯并呋喃及其应用 |
| 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 |
| FR2973027A1 (fr) * | 2011-03-24 | 2012-09-28 | Sanofi Aventis | Procede de synthese de derives de cetobenzofurane |
| HUP1100167A2 (en) * | 2011-03-29 | 2012-11-28 | Sanofi Sa | Process for preparation of dronedarone by mesylation |
| HUP1100165A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Process for preparation of dronedarone by n-butylation |
| WO2013014480A1 (en) * | 2011-07-26 | 2013-01-31 | Sanofi | Process for preparation of dronedarone using amide intermediary compound |
| 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 |
| WO2013121235A2 (en) | 2012-02-13 | 2013-08-22 | Sanofi | Process for preparation of dronedarone by removal of hydroxyl group |
| WO2013121234A1 (en) | 2012-02-14 | 2013-08-22 | 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 |
| CN102690250A (zh) * | 2012-05-08 | 2012-09-26 | 郑州明泽医药科技有限公司 | 决奈达隆中间体及其制备方法 |
| WO2013178337A1 (en) | 2012-05-31 | 2013-12-05 | Sanofi | Process for preparation of dronedarone by grignard reaction |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3340300A (en) | 1964-10-05 | 1967-09-05 | American Cyanamid Co | Trimethoxy benzoylacetaldehyde oximes |
| US3558667A (en) * | 1968-11-01 | 1971-01-26 | Sterling Drug Inc | Benzofurans from o-phenyl ketoximes |
| JPS60169446A (ja) | 1984-02-15 | 1985-09-02 | Mitsui Petrochem Ind Ltd | ニトロフエノキシアミン類の製造方法 |
| JPS63139180A (ja) * | 1986-12-02 | 1988-06-10 | Tanabe Seiyaku Co Ltd | カルボン酸誘導体 |
| JP2982130B2 (ja) * | 1990-02-06 | 1999-11-22 | ダイセル化学工業株式会社 | β−ケトアミド合成用触媒およびβ−ケトアミドの製造方法 |
| KR0168056B1 (ko) * | 1990-04-26 | 1999-03-20 | 베르너 발데크 | 선형 1,3-디케톤의 제조방법 |
| 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. |
| DE4244390A1 (de) | 1992-12-29 | 1994-06-30 | Basf Ag | Verfahren zur Herstellung von Oximino-Derivaten und neue Oximino-Derivate |
| GB9416219D0 (en) | 1994-08-11 | 1994-10-05 | Karobio Ab | Receptor ligands |
| FR2746013B1 (fr) | 1996-03-18 | 1998-05-29 | Sanofi Sa | Utilisation de composes antiarythmiques dans la prevention de la mortalite post infarctus |
| AU6320998A (en) * | 1997-02-21 | 1998-09-09 | Bristol-Myers Squibb Company | Benzoic acid derivatives and related compounds as antiarrhythmic agents |
| FR2764800B1 (fr) | 1997-06-23 | 1999-09-10 | Sanofi Sa | Composition pharmaceutique solide contenant des derives de benzofuranne |
| GB9817118D0 (en) * | 1998-08-07 | 1998-10-07 | Glaxo Group Ltd | Pharmaceutical compounds |
| FR2803846B1 (fr) | 2000-01-17 | 2002-04-05 | Clariant France Sa | 3-(1-hydroxy-pentylidene)-5-nitro-3h-benzofuran-2-one, son procede de preparation et son utilisation |
| US6687428B2 (en) | 2000-09-21 | 2004-02-03 | Tera Op (Usa) Inc. | Optical switch |
| FR2817750B1 (fr) | 2000-12-11 | 2003-02-21 | Sanofi Synthelabo | Composition pharmaceutique de dronedarone pour administration parenterale |
| FR2817865B1 (fr) | 2000-12-11 | 2005-02-18 | Sanofi Synthelabo | Derive aminoalkoxybenzoyle sous forme de sel, son procede de preparation et son utilisation comme intermediaire de synthese |
| FR2817864B1 (fr) * | 2000-12-11 | 2003-02-21 | Sanofi Synthelabo | Derive de methanesulfonamido-benzofurane, son procede de preparation et son utilisation comme intermediaire de synthese |
| EP1355871A1 (en) | 2001-02-02 | 2003-10-29 | Roche Vitamins AG | Process for the purification of 1,3-diketones |
| JP2002371076A (ja) | 2001-06-14 | 2002-12-26 | Sumitomo Seika Chem Co Ltd | ２−アルキル−３−アシルベンゾフラン類の製造方法 |
| IL146389A0 (en) | 2001-11-08 | 2002-07-25 | Isp Finetech Ltd | Process for the preparation of dronedarone |
| FR2864536B1 (fr) * | 2003-12-24 | 2006-03-17 | Clariant France Sa | Procede de preparation de n-alkyl-2 (hydroxy-4-benzoyl)-3 benzofurannes et intermediaires pour sa mise en oeuvre |
| WO2007043400A1 (ja) * | 2005-10-07 | 2007-04-19 | Kissei Pharmaceutical Co., Ltd. | 含窒素芳香族複素環化合物およびそれを含有する医薬組成物 |
| GB0611210D0 (en) | 2006-06-07 | 2006-07-19 | Cambrex Karlskoga Ab | Process |
| CN100560067C (zh) | 2006-09-29 | 2009-11-18 | 北京德众万全药物技术开发有限公司 | 盐酸决奈达隆口服药物组合物及其制备方法 |
| CN101153012B (zh) | 2006-09-29 | 2010-06-23 | 北京德众万全药物技术开发有限公司 | 一种决奈达隆关键中间体的新的制备方法 |
| GB0719180D0 (en) | 2007-10-02 | 2007-11-14 | Cambrex Karlskoga Ab | New process |
| JP5654994B2 (ja) | 2008-10-02 | 2015-01-14 | カンブレックス カルルスクーガ アクチ ボラケットＣａｍｂｒｅｘ Ｋａｒｌｓｋｏｇａ Ａｂ | ジケトン及び薬剤を製造するための新しいプロセス |
-
2007
- 2007-10-02 GB GBGB0719180.2A patent/GB0719180D0/en not_active Ceased
-
2008
- 2008-10-02 ES ES13167925.0T patent/ES2589011T3/es active Active
- 2008-10-02 ES ES11075168.2T patent/ES2559939T3/es active Active
- 2008-10-02 EP EP08806486A patent/EP2200993B1/en not_active Not-in-force
- 2008-10-02 WO PCT/GB2008/003341 patent/WO2009044143A2/en not_active Ceased
- 2008-10-02 PL PL11075168T patent/PL2388256T3/pl unknown
- 2008-10-02 EP EP11075168.2A patent/EP2388256B1/en not_active Not-in-force
- 2008-10-02 CN CN201310195267.6A patent/CN103342633B/zh not_active Expired - Fee Related
- 2008-10-02 BR BRPI0817423-7A patent/BRPI0817423A2/pt not_active IP Right Cessation
- 2008-10-02 CN CN2008801163899A patent/CN101861308B/zh not_active Expired - Fee Related
- 2008-10-02 PL PL08806486T patent/PL2200993T3/pl unknown
- 2008-10-02 EP EP13167925.0A patent/EP2636670B1/en not_active Not-in-force
- 2008-10-02 ES ES08806486T patent/ES2395174T3/es active Active
- 2008-10-02 JP JP2010527524A patent/JP5577252B2/ja not_active Expired - Fee Related
- 2008-10-02 US US12/681,299 patent/US8519165B2/en not_active Expired - Fee Related
- 2008-10-02 CN CN2011102205750A patent/CN102382086A/zh active Pending
- 2008-10-02 PL PL13167925.0T patent/PL2636670T3/pl unknown
-
2013
- 2013-07-18 US US13/944,950 patent/US8779201B2/en not_active Expired - Fee Related
-
2014
- 2014-06-04 JP JP2014115816A patent/JP5943965B2/ja not_active Expired - Fee Related
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