JP2013530959A5 - - Google Patents
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- Publication number
- JP2013530959A5 JP2013530959A5 JP2013513534A JP2013513534A JP2013530959A5 JP 2013530959 A5 JP2013530959 A5 JP 2013530959A5 JP 2013513534 A JP2013513534 A JP 2013513534A JP 2013513534 A JP2013513534 A JP 2013513534A JP 2013530959 A5 JP2013530959 A5 JP 2013530959A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- dronedarone hydrochloride
- ether
- aliphatic
- solvent
- 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 description 27
- CPKOXUVSOOKUDA-UHFFFAOYSA-N 1-bromo-5-fluoro-2-iodo-4-methylbenzene Chemical compound CC1=CC(I)=C(Br)C=C1F CPKOXUVSOOKUDA-UHFFFAOYSA-N 0.000 claims description 11
- 229960002919 dronedarone hydrochloride Drugs 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- SPIIBUQYWNFELT-UHFFFAOYSA-N (5-amino-2-butyl-1-benzofuran-3-yl)-[4-[3-(dibutylamino)propoxy]phenyl]methanone Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C(N)C=C12 SPIIBUQYWNFELT-UHFFFAOYSA-N 0.000 claims description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- -1 4- [3- (dibutylamino) Propoxy] benzoyl Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 4
- 150000008282 halocarbons Chemical class 0.000 claims 4
- 150000002576 ketones Chemical class 0.000 claims 4
- 150000002825 nitriles Chemical class 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000012670 alkaline solution Substances 0.000 claims 2
- 150000004292 cyclic ethers Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
- 229960002084 dronedarone Drugs 0.000 claims 1
- 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 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010101957337A CN102276561A (zh) | 2010-06-09 | 2010-06-09 | 决奈达隆及其盐的制备方法 |
| CN201010195733.7 | 2010-06-09 | ||
| PCT/CN2011/075255 WO2011153923A1 (zh) | 2010-06-09 | 2011-06-03 | 决奈达隆及其盐的制备方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013530959A JP2013530959A (ja) | 2013-08-01 |
| JP2013530959A5 true JP2013530959A5 (https=) | 2015-10-08 |
| JP5873484B2 JP5873484B2 (ja) | 2016-03-01 |
Family
ID=45097533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013513534A Expired - Fee Related JP5873484B2 (ja) | 2010-06-09 | 2011-06-03 | ドロネダロン及びその塩の製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8481763B2 (https=) |
| EP (1) | EP2581369A4 (https=) |
| JP (1) | JP5873484B2 (https=) |
| CN (2) | CN102276561A (https=) |
| WO (1) | WO2011153923A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120108828A1 (en) * | 2010-09-09 | 2012-05-03 | USV Limited, B.S.D. Marg | Synthesis of dronedarone and salts thereof |
| EP2447256A1 (en) * | 2010-10-21 | 2012-05-02 | Laboratorios Lesvi, S.L. | Process for obtaining dronedarone |
| 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 |
| WO2012153225A1 (en) * | 2011-05-09 | 2012-11-15 | Alembic Pharmaceuticals Limited | Improved processes for obtaining high purity of dronedarone hydrochloride |
| CN103044369A (zh) * | 2012-12-21 | 2013-04-17 | 北京华禧联合科技发展有限公司 | 一种盐酸决奈达隆的精制方法 |
| WO2014203058A1 (en) * | 2013-06-17 | 2014-12-24 | Aurobindo Pharma Limited | An improved process for preparing benzofuran compound |
| CN107880003A (zh) * | 2016-09-30 | 2018-04-06 | 北京新领先医药科技发展有限公司 | 一种精制盐酸决奈达隆的新方法 |
| CN112442003B (zh) * | 2020-12-17 | 2022-04-19 | 南京方生和医药科技有限公司 | 一种决奈达隆中间体杂质及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US522351A (en) | 1894-07-03 | phillips | ||
| 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. |
| 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 |
| IL146389A0 (en) | 2001-11-08 | 2002-07-25 | Isp Finetech Ltd | Process for the preparation of dronedarone |
| FR2833262A1 (fr) | 2001-12-06 | 2003-06-13 | Rhodia Chimie Sa | Procede de monosulfonylation d'un compose de type aminobenzofuranne ou aminobenzothiophene |
| 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 |
| FR2915482B1 (fr) * | 2007-04-27 | 2009-11-27 | Finorga | Procede de preparation du 2-(n-butyl)-5-nitrobenzofurane. |
-
2010
- 2010-06-09 CN CN2010101957337A patent/CN102276561A/zh active Pending
-
2011
- 2011-06-03 US US13/701,642 patent/US8481763B2/en not_active Expired - Fee Related
- 2011-06-03 EP EP11791914.2A patent/EP2581369A4/en not_active Withdrawn
- 2011-06-03 JP JP2013513534A patent/JP5873484B2/ja not_active Expired - Fee Related
- 2011-06-03 CN CN201180003259.6A patent/CN102471302B/zh not_active Expired - Fee Related
- 2011-06-03 WO PCT/CN2011/075255 patent/WO2011153923A1/zh not_active Ceased
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