JP2007517012A5 - - Google Patents
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- Publication number
- JP2007517012A5 JP2007517012A5 JP2006546365A JP2006546365A JP2007517012A5 JP 2007517012 A5 JP2007517012 A5 JP 2007517012A5 JP 2006546365 A JP2006546365 A JP 2006546365A JP 2006546365 A JP2006546365 A JP 2006546365A JP 2007517012 A5 JP2007517012 A5 JP 2007517012A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- halide
- process according
- alkyl
- 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 16
- -1 alkylphenyl ether Chemical compound 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 13
- 239000002841 Lewis acid Substances 0.000 claims 8
- 150000007517 lewis acids Chemical class 0.000 claims 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 230000002140 halogenating effect Effects 0.000 claims 6
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical group COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 4
- 238000006900 dealkylation reaction Methods 0.000 claims 4
- 238000010438 heat treatment Methods 0.000 claims 4
- 230000020335 dealkylation Effects 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 239000003377 acid catalyst Substances 0.000 claims 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- 229910052797 bismuth Inorganic materials 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 229910052742 iron Inorganic materials 0.000 claims 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 239000010936 titanium Substances 0.000 claims 2
- 229910052719 titanium Inorganic materials 0.000 claims 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- GJQZKBVGMRTLJN-UHFFFAOYSA-N [P].P(Cl)(Cl)Cl Chemical compound [P].P(Cl)(Cl)Cl GJQZKBVGMRTLJN-UHFFFAOYSA-N 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical group ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0315398A FR2864536B1 (fr) | 2003-12-24 | 2003-12-24 | Procede de preparation de n-alkyl-2 (hydroxy-4-benzoyl)-3 benzofurannes et intermediaires pour sa mise en oeuvre |
| FR0315398 | 2003-12-24 | ||
| PCT/IB2004/004158 WO2005066149A1 (en) | 2003-12-24 | 2004-12-15 | Process for the preperation of n-alkyl-2(hydroxy-4 benzoyl)-3 benzofurans and its intermediates thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011175599A Division JP5400840B2 (ja) | 2003-12-24 | 2011-08-11 | Ｎ−アルキル−２（ヒドロキシ−４ベンゾイル）−３ベンゾフラン及びその中間体の調製方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007517012A JP2007517012A (ja) | 2007-06-28 |
| JP2007517012A5 true JP2007517012A5 (enExample) | 2008-01-17 |
| JP4896735B2 JP4896735B2 (ja) | 2012-03-14 |
Family
ID=34639607
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006546365A Expired - Fee Related JP4896735B2 (ja) | 2003-12-24 | 2004-12-15 | Ｎ−アルキル−２（ヒドロキシ−４ベンゾイル）−３ベンゾフラン及びその中間体の調製方法 |
| JP2011175599A Expired - Fee Related JP5400840B2 (ja) | 2003-12-24 | 2011-08-11 | Ｎ−アルキル−２（ヒドロキシ−４ベンゾイル）−３ベンゾフラン及びその中間体の調製方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011175599A Expired - Fee Related JP5400840B2 (ja) | 2003-12-24 | 2011-08-11 | Ｎ−アルキル−２（ヒドロキシ−４ベンゾイル）−３ベンゾフラン及びその中間体の調製方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7544817B2 (enExample) |
| EP (2) | EP2508517A1 (enExample) |
| JP (2) | JP4896735B2 (enExample) |
| KR (1) | KR101150627B1 (enExample) |
| CN (2) | CN100475801C (enExample) |
| DK (1) | DK1699772T3 (enExample) |
| ES (1) | ES2400943T3 (enExample) |
| FR (1) | FR2864536B1 (enExample) |
| NO (1) | NO20062936L (enExample) |
| TW (1) | TWI365878B (enExample) |
| WO (1) | WO2005066149A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2914644B1 (fr) * | 2007-04-06 | 2009-06-05 | Finorga Soc Par Actions Simpli | Procede de preparation de 2-(n-butyl)-3-(4-hydroxybenzoyl) -5-nitrobenzofurane |
| GB0719180D0 (en) * | 2007-10-02 | 2007-11-14 | Cambrex Karlskoga Ab | New process |
| CN102065855A (zh) | 2008-04-17 | 2011-05-18 | 赛诺菲-安万特 | 决奈达隆在制备用于预防因心血管疾病住院或死亡的药物中的用途 |
| EP2246341A1 (en) | 2009-01-23 | 2010-11-03 | Lonza Ltd. | Process for preparing 2-Alkyl-3-aroyl-5-nitro-benzofurans |
| IT1398317B1 (it) * | 2010-02-23 | 2013-02-22 | Chimico Internaz Spa Lab | Nuovo procedimento per la preparazione del dronedarone. |
| 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 |
| EP2452938A1 (en) | 2010-11-12 | 2012-05-16 | LEK Pharmaceuticals d.d. | Process for the preparation of 3-aroyl-5-aminobenzofuran derivatives |
| FR2973027A1 (fr) * | 2011-03-24 | 2012-09-28 | Sanofi Aventis | Procede de synthese de derives de cetobenzofurane |
| CN103265513A (zh) * | 2013-03-25 | 2013-08-28 | 德州学院 | 制备2-烷基-3-(4-羟基苯甲酰基)苯并呋喃的方法 |
| CA3232459A1 (en) * | 2021-07-21 | 2023-01-26 | Jiangsu Chia Tai Fenghai Pharmaceutical Co., Ltd. | Compound for treating diseases related to cerebral ischemic injury |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1382742A (en) * | 1972-09-19 | 1975-02-05 | Labaz | Benzofuran derivatives and process for preparing the same |
| GB1456323A (en) * | 1974-06-06 | 1976-11-24 | Labaz | Benzothiophenes process for preparing them and pharmaceutical compositions containing the same |
| US3983245A (en) * | 1975-02-06 | 1976-09-28 | Smithkline Corporation | Certain 4-(3-azacycloalkoxy or azacycloalkylmethoxy)benzoylbenzofurans or benzothiophenes |
| US4133814A (en) * | 1975-10-28 | 1979-01-09 | Eli Lilly And Company | 2-Phenyl-3-aroylbenzothiophenes useful as antifertility agents |
| US4831054A (en) * | 1988-04-18 | 1989-05-16 | Taro Pharmaceuticals, Ltd. | 2-Alkyl-3-benzoylbenzofurans useful for treating cardiac arrhythmia |
| FR2653431B1 (fr) * | 1989-10-23 | 1994-05-27 | Sanofi Sa | Procede de preparation de derives de benzoyl-3 benzofuranne. |
| JP2873599B2 (ja) * | 1990-03-09 | 1999-03-24 | 寿製薬株式会社 | 新規ベンゾフラン誘導体、尿酸排泄剤及びその製法 |
| 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. |
| JPH06184132A (ja) * | 1992-12-22 | 1994-07-05 | Kotobuki Seiyaku Kk | ベンゾフラン誘導体及びその製造方法並びに尿酸排泄剤 |
| GB9416219D0 (en) * | 1994-08-11 | 1994-10-05 | Karobio Ab | Receptor ligands |
| EP1077965A1 (en) * | 1998-05-12 | 2001-02-28 | American Home Products Corporation | Phenyl oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia |
| 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 |
-
2003
- 2003-12-24 FR FR0315398A patent/FR2864536B1/fr not_active Expired - Fee Related
-
2004
- 2004-12-15 CN CNB2004800382852A patent/CN100475801C/zh not_active Expired - Fee Related
- 2004-12-15 WO PCT/IB2004/004158 patent/WO2005066149A1/en not_active Ceased
- 2004-12-15 CN CN200910006741XA patent/CN101486698B/zh not_active Expired - Fee Related
- 2004-12-15 EP EP12003772A patent/EP2508517A1/en not_active Withdrawn
- 2004-12-15 DK DK04801395.7T patent/DK1699772T3/da active
- 2004-12-15 EP EP04801395A patent/EP1699772B1/en not_active Expired - Lifetime
- 2004-12-15 JP JP2006546365A patent/JP4896735B2/ja not_active Expired - Fee Related
- 2004-12-15 US US10/584,440 patent/US7544817B2/en not_active Expired - Fee Related
- 2004-12-15 KR KR1020067012489A patent/KR101150627B1/ko not_active Expired - Fee Related
- 2004-12-15 ES ES04801395T patent/ES2400943T3/es not_active Expired - Lifetime
- 2004-12-22 TW TW093140136A patent/TWI365878B/zh not_active IP Right Cessation
-
2006
- 2006-06-23 NO NO20062936A patent/NO20062936L/no unknown
-
2011
- 2011-08-11 JP JP2011175599A patent/JP5400840B2/ja not_active Expired - Fee Related
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