RU2012133967A - Новый способ получения дронедарона - Google Patents
Новый способ получения дронедарона Download PDFInfo
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- RU2012133967A RU2012133967A RU2012133967/04A RU2012133967A RU2012133967A RU 2012133967 A RU2012133967 A RU 2012133967A RU 2012133967/04 A RU2012133967/04 A RU 2012133967/04A RU 2012133967 A RU2012133967 A RU 2012133967A RU 2012133967 A RU2012133967 A RU 2012133967A
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- Prior art keywords
- formula
- salt
- compounds
- compound
- alkaline earth
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- 238000004519 manufacturing process Methods 0.000 title abstract 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 title 1
- 229960002084 dronedarone Drugs 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 18
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 11
- 150000001875 compounds Chemical class 0.000 claims abstract 11
- 150000003839 salts Chemical class 0.000 claims abstract 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000012442 inert solvent Substances 0.000 claims abstract 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000003513 alkali Substances 0.000 claims abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 4
- -1 alkali metal salts Chemical class 0.000 claims abstract 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract 4
- 239000003054 catalyst Substances 0.000 claims abstract 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract 4
- 150000008282 halocarbons Chemical class 0.000 claims abstract 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract 4
- 239000000203 mixture Substances 0.000 claims abstract 4
- 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 abstract 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical class C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims abstract 2
- VFUIMOGHUGFEBP-UHFFFAOYSA-N 4-[3-(dibutylamino)propoxy]benzoyl chloride Chemical compound CCCCN(CCCC)CCCOC1=CC=C(C(Cl)=O)C=C1 VFUIMOGHUGFEBP-UHFFFAOYSA-N 0.000 claims abstract 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract 2
- 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 abstract 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001340 alkali metals Chemical class 0.000 claims abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract 2
- 229910052791 calcium Inorganic materials 0.000 claims abstract 2
- 239000011575 calcium Substances 0.000 claims abstract 2
- 159000000007 calcium salts Chemical class 0.000 claims abstract 2
- 230000003993 interaction Effects 0.000 claims abstract 2
- 229910052744 lithium Inorganic materials 0.000 claims abstract 2
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract 2
- 159000000002 lithium salts Chemical class 0.000 claims abstract 2
- 229910052749 magnesium Inorganic materials 0.000 claims abstract 2
- 239000011777 magnesium Substances 0.000 claims abstract 2
- 159000000003 magnesium salts Chemical class 0.000 claims abstract 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052700 potassium Inorganic materials 0.000 claims abstract 2
- 239000011591 potassium Substances 0.000 claims abstract 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims abstract 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims abstract 2
- 229910052708 sodium Inorganic materials 0.000 claims abstract 2
- 239000011734 sodium Substances 0.000 claims abstract 2
- 159000000000 sodium salts Chemical class 0.000 claims abstract 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims 1
- 229910001508 alkali metal halide Inorganic materials 0.000 claims 1
- 150000008045 alkali metal halides Chemical class 0.000 claims 1
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims 1
- 229910001622 calcium bromide Inorganic materials 0.000 claims 1
- 239000001110 calcium chloride Substances 0.000 claims 1
- 229910001628 calcium chloride Inorganic materials 0.000 claims 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 claims 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims 1
- 229910001623 magnesium bromide Inorganic materials 0.000 claims 1
- 229910001629 magnesium chloride Inorganic materials 0.000 claims 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1. Способ получения N-[2-бутил-3-{4-[(3-дибутиламино)пропокси]бензоил}-l-бензофуран-5-ил]метансульфонамида формулы I.и его фармацевтически приемлемых солей, отличающийся тем, что соль щелочного или щелочноземельного металла соединения формулы IIвзаимодействует с 4-[3-(дибутиламино)пропокси]бензоилхлоридом формулы IIIв присутствии катализатора и, необязательно, соединение формулы I трансформируется в соль или высвобождается из его соли.2. Способ по п.1, отличающийся тем, что щелочной металл включает литий, натрий или калий, а щелочноземельный металл включает магний или кальций.3. Способ по п.1, отличающийся тем, что взаимодействие соединения формулы II и соединения формулы III проводят в инертном растворителе или в смеси инертных растворителей.4. Способ по п.3, отличающийся тем, что в качестве инертного растворителя используют галогенированные углеводороды.5. Способ по п.4, отличающийся тем, что в качестве галогенированных углеводородов используют дихлорметан, дихлорэтан, хлорбензол или их смеси.6. Способ по п.1, отличающийся тем, что в качестве катализатора используют хлорид железа(III) или хлорид алюминия.7. Способ по п.1, отличающийся тем, что реакцию проводят при температуре от 10 до 100°C.8. Соли щелочных и щелочноземельных металлов 2-бутил-5-метансульфонамидбензофурана формулы II9. Соединения по п.8, отличающиеся тем, что они представляют собой литиевую соль IIa, натриевую соль IIb, калиевую соль IIc, магниевую соль IId и кальциевую соль соединения формулы II.10. Способ получения солей щелочных металлов соединения II по любому из пп.8-9, отличающийся тем, что соединение формулы IIвзаимодействует с соответствующим гидроксидом щелочного металла.11.
Claims (13)
1. Способ получения N-[2-бутил-3-{4-[(3-дибутиламино)пропокси]бензоил}-l-бензофуран-5-ил]метансульфонамида формулы I.
и его фармацевтически приемлемых солей, отличающийся тем, что соль щелочного или щелочноземельного металла соединения формулы II
взаимодействует с 4-[3-(дибутиламино)пропокси]бензоилхлоридом формулы III
в присутствии катализатора и, необязательно, соединение формулы I трансформируется в соль или высвобождается из его соли.
2. Способ по п.1, отличающийся тем, что щелочной металл включает литий, натрий или калий, а щелочноземельный металл включает магний или кальций.
3. Способ по п.1, отличающийся тем, что взаимодействие соединения формулы II и соединения формулы III проводят в инертном растворителе или в смеси инертных растворителей.
4. Способ по п.3, отличающийся тем, что в качестве инертного растворителя используют галогенированные углеводороды.
5. Способ по п.4, отличающийся тем, что в качестве галогенированных углеводородов используют дихлорметан, дихлорэтан, хлорбензол или их смеси.
6. Способ по п.1, отличающийся тем, что в качестве катализатора используют хлорид железа(III) или хлорид алюминия.
7. Способ по п.1, отличающийся тем, что реакцию проводят при температуре от 10 до 100°C.
9. Соединения по п.8, отличающиеся тем, что они представляют собой литиевую соль IIa, натриевую соль IIb, калиевую соль IIc, магниевую соль IId и кальциевую соль соединения формулы II.
11. Способ по п.10, отличающийся тем, что гидроксид щелочного металла включает гидроксид лития, гидроксид натрия или гидроксид калия.
13. Способ по п.12, отличающийся тем, что галогенид щелочноземельного металла включает хлорид магния, бромид магния, хлорид кальция или бромид кальция.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HUP1000010 | 2010-01-08 | ||
HU1000010A HUP1000010A2 (en) | 2010-01-08 | 2010-01-08 | Process for producing dronedarone |
PCT/HU2010/000143 WO2011083346A1 (en) | 2010-01-08 | 2010-12-15 | New process for the preparation of dronedarone |
Publications (1)
Publication Number | Publication Date |
---|---|
RU2012133967A true RU2012133967A (ru) | 2014-02-20 |
Family
ID=89989488
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2012133967/04A RU2012133967A (ru) | 2010-01-08 | 2010-12-15 | Новый способ получения дронедарона |
Country Status (17)
Country | Link |
---|---|
US (1) | US8658809B2 (ru) |
EP (1) | EP2521720B1 (ru) |
JP (1) | JP2013516451A (ru) |
KR (1) | KR20120115365A (ru) |
CN (1) | CN102666522A (ru) |
AR (1) | AR079843A1 (ru) |
AU (1) | AU2010340786A1 (ru) |
BR (1) | BR112012016448A2 (ru) |
CA (1) | CA2786218A1 (ru) |
HU (1) | HUP1000010A2 (ru) |
IL (1) | IL220523A0 (ru) |
MX (1) | MX2012007897A (ru) |
RU (1) | RU2012133967A (ru) |
SG (1) | SG182405A1 (ru) |
TW (1) | TW201139399A (ru) |
UY (1) | UY33168A (ru) |
WO (1) | WO2011083346A1 (ru) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HUP0900759A2 (en) | 2009-12-08 | 2011-11-28 | Sanofi Aventis | Novel process for producing 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 |
FR2958291B1 (fr) | 2010-04-01 | 2013-07-05 | Sanofi Aventis | Procede de preparation de derives d'amino-benzofurane |
HUP1000330A2 (en) | 2010-06-18 | 2011-12-28 | Sanofi Sa | Process for the preparation of dronedarone and the novel intermediates |
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 |
HUP1000386A2 (en) | 2010-07-22 | 2012-05-29 | Sanofi Sa | Novel process for producing dronedarone |
HUP1100165A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Process for preparation of dronedarone by n-butylation |
HUP1100167A2 (en) | 2011-03-29 | 2012-11-28 | Sanofi Sa | Process for preparation of dronedarone by mesylation |
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 |
US9249119B2 (en) | 2012-02-14 | 2016-02-02 | 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 |
US9238636B2 (en) | 2012-05-31 | 2016-01-19 | Sanofi | Process for preparation of dronedarone by Grignard reaction |
EP2963869A4 (en) | 2013-02-26 | 2016-09-28 | Nec Corp | COMMUNICATION SYSTEM, SWITCH, CONTROL APPARATUS, CONTROL CHANNEL CONFIGURATION METHOD AND PROGRAM |
CN103450124B (zh) * | 2013-08-30 | 2016-03-09 | 江苏九九久科技股份有限公司 | 决奈达隆合成方法 |
Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
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 |
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 |
DE10237819A1 (de) | 2002-08-19 | 2004-03-04 | Bayer Ag | 5-Nitrobenzofurane |
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 |
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 |
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 |
FR2958289B1 (fr) | 2010-03-30 | 2012-06-15 | Sanofi Aventis | Procede de preparation de derives de 3-ceto-benzofurane |
FR2958291B1 (fr) | 2010-04-01 | 2013-07-05 | Sanofi Aventis | Procede de preparation de derives d'amino-benzofurane |
HUP1000330A2 (en) | 2010-06-18 | 2011-12-28 | Sanofi Sa | Process for the preparation of dronedarone and the novel intermediates |
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 |
HUP1000386A2 (en) | 2010-07-22 | 2012-05-29 | Sanofi Sa | Novel process for producing dronedarone |
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 |
HUP1100166A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Reductive amination process for preparation of dronedarone using amine intermediary compound |
HUP1100165A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Process for preparation of dronedarone by n-butylation |
-
2010
- 2010-01-08 HU HU1000010A patent/HUP1000010A2/hu unknown
- 2010-12-15 CN CN2010800580717A patent/CN102666522A/zh active Pending
- 2010-12-15 MX MX2012007897A patent/MX2012007897A/es not_active Application Discontinuation
- 2010-12-15 KR KR1020127020680A patent/KR20120115365A/ko not_active Application Discontinuation
- 2010-12-15 JP JP2012547552A patent/JP2013516451A/ja not_active Withdrawn
- 2010-12-15 WO PCT/HU2010/000143 patent/WO2011083346A1/en active Application Filing
- 2010-12-15 RU RU2012133967/04A patent/RU2012133967A/ru not_active Application Discontinuation
- 2010-12-15 CA CA2786218A patent/CA2786218A1/en not_active Abandoned
- 2010-12-15 BR BRBR112012016448-1A patent/BR112012016448A2/pt not_active IP Right Cessation
- 2010-12-15 EP EP10809330.3A patent/EP2521720B1/en active Active
- 2010-12-15 SG SG2012050118A patent/SG182405A1/en unknown
- 2010-12-15 AU AU2010340786A patent/AU2010340786A1/en not_active Abandoned
-
2011
- 2011-01-06 AR ARP110100030A patent/AR079843A1/es unknown
- 2011-01-07 TW TW100100566A patent/TW201139399A/zh unknown
- 2011-01-07 UY UY0001033168A patent/UY33168A/es not_active Application Discontinuation
-
2012
- 2012-06-20 IL IL220523A patent/IL220523A0/en unknown
- 2012-06-29 US US13/537,930 patent/US8658809B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
AR079843A1 (es) | 2012-02-22 |
TW201139399A (en) | 2011-11-16 |
JP2013516451A (ja) | 2013-05-13 |
IL220523A0 (en) | 2012-08-30 |
BR112012016448A2 (pt) | 2015-09-01 |
HU1000010D0 (en) | 2010-03-01 |
MX2012007897A (es) | 2012-08-01 |
EP2521720A1 (en) | 2012-11-14 |
CN102666522A (zh) | 2012-09-12 |
HUP1000010A2 (en) | 2011-11-28 |
EP2521720B1 (en) | 2014-03-12 |
WO2011083346A1 (en) | 2011-07-14 |
UY33168A (es) | 2011-08-31 |
US20120330036A1 (en) | 2012-12-27 |
KR20120115365A (ko) | 2012-10-17 |
CA2786218A1 (en) | 2011-07-14 |
AU2010340786A1 (en) | 2012-07-26 |
US8658809B2 (en) | 2014-02-25 |
SG182405A1 (en) | 2012-08-30 |
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