CN101486698B - 取代的苯并呋喃及其制备方法 - Google Patents
取代的苯并呋喃及其制备方法 Download PDFInfo
- Publication number
- CN101486698B CN101486698B CN200910006741XA CN200910006741A CN101486698B CN 101486698 B CN101486698 B CN 101486698B CN 200910006741X A CN200910006741X A CN 200910006741XA CN 200910006741 A CN200910006741 A CN 200910006741A CN 101486698 B CN101486698 B CN 101486698B
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- CN
- China
- Prior art keywords
- formula
- alkyl
- butyl
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- compound
- 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.)
- Expired - Fee Related
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- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- IANQTJSKSUMEQM-UHFFFAOYSA-N benzofuran Natural products C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000001907 coumarones Chemical class 0.000 abstract 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical group O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 abstract 1
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 abstract 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- -1 methoxyl group Chemical group 0.000 description 8
- 125000005037 alkyl phenyl group Chemical group 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 7
- 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 description 6
- 239000002841 Lewis acid Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000002140 halogenating effect Effects 0.000 description 6
- 150000007517 lewis acids Chemical class 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- PGHQMJURMCAWQU-UHFFFAOYSA-N 2-butyl-5-nitro-1-benzofuran-3-carboxylic acid Chemical compound C1=C([N+]([O-])=O)C=C2C(C(O)=O)=C(CCCC)OC2=C1 PGHQMJURMCAWQU-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000026030 halogenation Effects 0.000 description 4
- 238000005658 halogenation reaction Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000020335 dealkylation Effects 0.000 description 3
- 238000006900 dealkylation reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- WNMGORRIIOYPKY-UHFFFAOYSA-N (2-butyl-5-nitro-1-benzofuran-3-yl)-(2-methoxyphenyl)methanone Chemical compound CCCCC=1OC2=CC=C([N+]([O-])=O)C=C2C=1C(=O)C1=CC=CC=C1OC WNMGORRIIOYPKY-UHFFFAOYSA-N 0.000 description 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 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RJMPDGNCDFVLHH-UHFFFAOYSA-N 3-(1-hydroxypentylidene)-5-nitro-1-benzofuran-2-one Chemical class C1=C([N+]([O-])=O)C=C2C(=C(O)CCCC)C(=O)OC2=C1 RJMPDGNCDFVLHH-UHFFFAOYSA-N 0.000 description 2
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000010812 external standard method Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003608 titanium Chemical class 0.000 description 2
- FZOSNJRKFPXEQU-UHFFFAOYSA-N (2-butyl-5-nitro-1-benzofuran-3-yl)-(2-hydroxyphenyl)methanone Chemical compound CCCCC=1OC2=CC=C([N+]([O-])=O)C=C2C=1C(=O)C1=CC=CC=C1O FZOSNJRKFPXEQU-UHFFFAOYSA-N 0.000 description 1
- 0 *C(C1=C(*)NC2=CCCC=C12)=O Chemical compound *C(C1=C(*)NC2=CCCC=C12)=O 0.000 description 1
- XGAJABPTUOLUAE-UHFFFAOYSA-N 2-butyl-5-nitro-1-benzofuran Chemical compound [O-][N+](=O)C1=CC=C2OC(CCCC)=CC2=C1 XGAJABPTUOLUAE-UHFFFAOYSA-N 0.000 description 1
- RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 description 1
- LPMMCJSIUVQZFD-UHFFFAOYSA-N 5-nitro-1-benzofuran Chemical compound [O-][N+](=O)C1=CC=C2OC=CC2=C1 LPMMCJSIUVQZFD-UHFFFAOYSA-N 0.000 description 1
- MHHWPBSIZBYLME-UHFFFAOYSA-N 5-nitro-3-pentanoyl-3h-1-benzofuran-2-one Chemical class C1=C([N+]([O-])=O)C=C2C(C(=O)CCCC)C(=O)OC2=C1 MHHWPBSIZBYLME-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 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 description 1
- 229960002084 dronedarone Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| 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 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004800382852A Division CN100475801C (zh) | 2003-12-24 | 2004-12-15 | 制备2-正烷基-3-(4-羟基苯甲酰基)苯并呋喃及其中间体的方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101486698A CN101486698A (zh) | 2009-07-22 |
| CN101486698B true CN101486698B (zh) | 2011-07-27 |
Family
ID=34639607
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200910006741XA Expired - Fee Related CN101486698B (zh) | 2003-12-24 | 2004-12-15 | 取代的苯并呋喃及其制备方法 |
| CNB2004800382852A Expired - Fee Related CN100475801C (zh) | 2003-12-24 | 2004-12-15 | 制备2-正烷基-3-(4-羟基苯甲酰基)苯并呋喃及其中间体的方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004800382852A Expired - Fee Related CN100475801C (zh) | 2003-12-24 | 2004-12-15 | 制备2-正烷基-3-(4-羟基苯甲酰基)苯并呋喃及其中间体的方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7544817B2 (https=) |
| EP (2) | EP2508517A1 (https=) |
| JP (2) | JP4896735B2 (https=) |
| KR (1) | KR101150627B1 (https=) |
| CN (2) | CN101486698B (https=) |
| DK (1) | DK1699772T3 (https=) |
| ES (1) | ES2400943T3 (https=) |
| FR (1) | FR2864536B1 (https=) |
| NO (1) | NO20062936L (https=) |
| TW (1) | TWI365878B (https=) |
| WO (1) | WO2005066149A1 (https=) |
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 |
| 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 |
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5223510A (en) * | 1990-08-06 | 1993-06-29 | Sanofi | Alkylaminoalkyl derivatives of benzofuran, benzothiophene, indole and indolizine, process for their preparation and compositions containing them |
| WO1996005190A1 (en) * | 1994-08-11 | 1996-02-22 | Karo Bio Ab | 3-benzoyl benzofuran derivatives as thyroid hormone antagonists |
| CN1308621A (zh) * | 1998-05-12 | 2001-08-15 | 美国家用产品公司 | 用于治疗胰岛素抗性和高血糖的苯基氧代－乙酸 |
Family Cites Families (9)
| 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 |
| 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 |
| 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 KR KR1020067012489A patent/KR101150627B1/ko not_active Expired - Fee Related
- 2004-12-15 US US10/584,440 patent/US7544817B2/en not_active Expired - Fee Related
- 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 JP JP2006546365A patent/JP4896735B2/ja not_active Expired - Fee Related
- 2004-12-15 EP EP04801395A patent/EP1699772B1/en not_active Expired - Lifetime
- 2004-12-15 WO PCT/IB2004/004158 patent/WO2005066149A1/en not_active Ceased
- 2004-12-15 ES ES04801395T patent/ES2400943T3/es not_active Expired - Lifetime
- 2004-12-15 DK DK04801395.7T patent/DK1699772T3/da active
- 2004-12-15 CN CNB2004800382852A patent/CN100475801C/zh not_active Expired - Fee Related
- 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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5223510A (en) * | 1990-08-06 | 1993-06-29 | Sanofi | Alkylaminoalkyl derivatives of benzofuran, benzothiophene, indole and indolizine, process for their preparation and compositions containing them |
| WO1996005190A1 (en) * | 1994-08-11 | 1996-02-22 | Karo Bio Ab | 3-benzoyl benzofuran derivatives as thyroid hormone antagonists |
| CN1308621A (zh) * | 1998-05-12 | 2001-08-15 | 美国家用产品公司 | 用于治疗胰岛素抗性和高血糖的苯基氧代－乙酸 |
Non-Patent Citations (1)
| Title |
|---|
| Larry J. Powers.Chemistry and Antibacterial Activity of Nitrobenzofurans.Journal of Medicinal Chemistry.1976,19(1),57－62. * |
Also Published As
| Publication number | Publication date |
|---|---|
| US7544817B2 (en) | 2009-06-09 |
| JP2007517012A (ja) | 2007-06-28 |
| HK1097835A1 (zh) | 2007-07-06 |
| EP1699772A1 (en) | 2006-09-13 |
| FR2864536B1 (fr) | 2006-03-17 |
| EP1699772B1 (en) | 2013-02-20 |
| ES2400943T3 (es) | 2013-04-15 |
| US20070155831A1 (en) | 2007-07-05 |
| WO2005066149A1 (en) | 2005-07-21 |
| JP5400840B2 (ja) | 2014-01-29 |
| TWI365878B (en) | 2012-06-11 |
| JP4896735B2 (ja) | 2012-03-14 |
| NO20062936L (no) | 2006-09-22 |
| JP2012012400A (ja) | 2012-01-19 |
| FR2864536A1 (fr) | 2005-07-01 |
| KR20060111608A (ko) | 2006-10-27 |
| KR101150627B1 (ko) | 2012-06-01 |
| CN100475801C (zh) | 2009-04-08 |
| DK1699772T3 (da) | 2013-05-27 |
| EP2508517A1 (en) | 2012-10-10 |
| CN101486698A (zh) | 2009-07-22 |
| TW200526616A (en) | 2005-08-16 |
| CN1898226A (zh) | 2007-01-17 |
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