NO327039B1 - 3-(1-hydroksy-pentyliden)-5-nitro-3H-benzofuran-2-on, fremgangsmate for fremstilling og anvendelse derav - Google Patents
3-(1-hydroksy-pentyliden)-5-nitro-3H-benzofuran-2-on, fremgangsmate for fremstilling og anvendelse derav Download PDFInfo
- Publication number
- NO327039B1 NO327039B1 NO20010265A NO20010265A NO327039B1 NO 327039 B1 NO327039 B1 NO 327039B1 NO 20010265 A NO20010265 A NO 20010265A NO 20010265 A NO20010265 A NO 20010265A NO 327039 B1 NO327039 B1 NO 327039B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- benzofuran
- nitro
- mol
- pentanoic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- RJMPDGNCDFVLHH-UHFFFAOYSA-N 3-(1-hydroxypentylidene)-5-nitro-1-benzofuran-2-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=C(O)CCCC)C(=O)OC2=C1 RJMPDGNCDFVLHH-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 7
- 239000000543 intermediate Substances 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 7
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 11
- OFONKIRKKMJQLZ-UHFFFAOYSA-N 5-nitro-3h-1-benzofuran-2-one Chemical compound [O-][N+](=O)C1=CC=C2OC(=O)CC2=C1 OFONKIRKKMJQLZ-UHFFFAOYSA-N 0.000 claims description 9
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 4
- MHHWPBSIZBYLME-UHFFFAOYSA-N 5-nitro-3-pentanoyl-3h-1-benzofuran-2-one Chemical group C1=C([N+]([O-])=O)C=C2C(C(=O)CCCC)C(=O)OC2=C1 MHHWPBSIZBYLME-UHFFFAOYSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 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 2
- 229960002084 dronedarone Drugs 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000725 suspension Substances 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
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0000523A FR2803846B1 (fr) | 2000-01-17 | 2000-01-17 | 3-(1-hydroxy-pentylidene)-5-nitro-3h-benzofuran-2-one, son procede de preparation et son utilisation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20010265D0 NO20010265D0 (no) | 2001-01-16 |
| NO20010265L NO20010265L (no) | 2001-07-18 |
| NO327039B1 true NO327039B1 (no) | 2009-04-06 |
Family
ID=8845968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20010265A NO327039B1 (no) | 2000-01-17 | 2001-01-16 | 3-(1-hydroksy-pentyliden)-5-nitro-3H-benzofuran-2-on, fremgangsmate for fremstilling og anvendelse derav |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6515147B2 (zh) |
| EP (1) | EP1116719B1 (zh) |
| JP (1) | JP4408578B2 (zh) |
| KR (1) | KR100788529B1 (zh) |
| CN (1) | CN1204133C (zh) |
| AT (1) | ATE292630T1 (zh) |
| DE (1) | DE60109829T2 (zh) |
| DK (1) | DK1116719T3 (zh) |
| ES (1) | ES2238408T3 (zh) |
| FR (1) | FR2803846B1 (zh) |
| HU (1) | HUP0100146A3 (zh) |
| NO (1) | NO327039B1 (zh) |
| TW (1) | TW564246B (zh) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10237819A1 (de) * | 2002-08-19 | 2004-03-04 | Bayer Ag | 5-Nitrobenzofurane |
| 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 |
| 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 |
| FR2930149B1 (fr) * | 2008-04-17 | 2011-02-18 | Sanofi Aventis | Association de dronedarone avec au moins un diuretique, son application en therapeutique |
| 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 |
| CN102276561A (zh) * | 2010-06-09 | 2011-12-14 | 江苏恒瑞医药股份有限公司 | 决奈达隆及其盐的制备方法 |
| 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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3248401A (en) * | 1966-04-26 | Diethylaminoe hoxybenzoyl benzofurans | ||
| US4252817A (en) * | 1975-03-12 | 1981-02-24 | Sandoz Ltd. | Substituted-2,3-dihydrobenzofuran-2-ones |
| FR2642755B1 (zh) * | 1989-02-07 | 1993-11-05 | Sanofi | |
| 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. |
| GB9416219D0 (en) * | 1994-08-11 | 1994-10-05 | Karobio Ab | Receptor ligands |
-
2000
- 2000-01-17 FR FR0000523A patent/FR2803846B1/fr not_active Expired - Fee Related
-
2001
- 2001-01-10 TW TW090100495A patent/TW564246B/zh not_active IP Right Cessation
- 2001-01-15 EP EP01810033A patent/EP1116719B1/en not_active Expired - Lifetime
- 2001-01-15 AT AT01810033T patent/ATE292630T1/de active
- 2001-01-15 DE DE60109829T patent/DE60109829T2/de not_active Expired - Lifetime
- 2001-01-15 ES ES01810033T patent/ES2238408T3/es not_active Expired - Lifetime
- 2001-01-15 HU HU0100146A patent/HUP0100146A3/hu unknown
- 2001-01-15 DK DK01810033T patent/DK1116719T3/da active
- 2001-01-16 KR KR1020010002333A patent/KR100788529B1/ko not_active IP Right Cessation
- 2001-01-16 NO NO20010265A patent/NO327039B1/no not_active IP Right Cessation
- 2001-01-16 JP JP2001007465A patent/JP4408578B2/ja not_active Expired - Fee Related
- 2001-01-17 US US09/761,452 patent/US6515147B2/en not_active Ceased
- 2001-01-17 CN CNB01101296XA patent/CN1204133C/zh not_active Expired - Fee Related
-
2005
- 2005-02-03 US US11/050,627 patent/USRE39755E1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE60109829T2 (de) | 2006-01-19 |
| JP4408578B2 (ja) | 2010-02-03 |
| EP1116719B1 (en) | 2005-04-06 |
| DE60109829D1 (de) | 2005-05-12 |
| FR2803846A1 (fr) | 2001-07-20 |
| NO20010265L (no) | 2001-07-18 |
| CN1306000A (zh) | 2001-08-01 |
| KR20010076278A (ko) | 2001-08-11 |
| ES2238408T3 (es) | 2005-09-01 |
| EP1116719A2 (en) | 2001-07-18 |
| NO20010265D0 (no) | 2001-01-16 |
| CN1204133C (zh) | 2005-06-01 |
| FR2803846B1 (fr) | 2002-04-05 |
| HU0100146D0 (en) | 2001-03-28 |
| HUP0100146A2 (hu) | 2002-01-28 |
| HUP0100146A3 (en) | 2003-07-28 |
| EP1116719A3 (en) | 2001-10-24 |
| JP2001233870A (ja) | 2001-08-28 |
| US20010012900A1 (en) | 2001-08-09 |
| KR100788529B1 (ko) | 2007-12-24 |
| DK1116719T3 (da) | 2005-07-18 |
| US6515147B2 (en) | 2003-02-04 |
| ATE292630T1 (de) | 2005-04-15 |
| TW564246B (en) | 2003-12-01 |
| USRE39755E1 (en) | 2007-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |