CN101861308B - 用于制备苯并呋喃类化合物的方法 - Google Patents
用于制备苯并呋喃类化合物的方法 Download PDFInfo
- Publication number
- CN101861308B CN101861308B CN2008801163899A CN200880116389A CN101861308B CN 101861308 B CN101861308 B CN 101861308B CN 2008801163899 A CN2008801163899 A CN 2008801163899A CN 200880116389 A CN200880116389 A CN 200880116389A CN 101861308 B CN101861308 B CN 101861308B
- Authority
- CN
- China
- Prior art keywords
- compound
- formula
- preparation
- salt
- reaction
- 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
Links
- 0 C*C(C*)N(C)OC1C(C)(*)C(*)C(*)C(*)C1 Chemical compound C*C(C*)N(C)OC1C(C)(*)C(*)C(*)C(*)C1 0.000 description 1
- ZBSCIIGOYCSAQV-UHFFFAOYSA-N CCCCc1c(C(c(cc2)ccc2O)=O)c(cc(cc2)N)c2[o]1 Chemical compound CCCCc1c(C(c(cc2)ccc2O)=O)c(cc(cc2)N)c2[o]1 ZBSCIIGOYCSAQV-UHFFFAOYSA-N 0.000 description 1
- WKFHEWCOYQNAQR-UHFFFAOYSA-N CCCCc1c(C(c(cc2)ccc2O)=O)c(cc(cc2)NS(C)(=O)=O)c2[o]1 Chemical compound CCCCc1c(C(c(cc2)ccc2O)=O)c(cc(cc2)NS(C)(=O)=O)c2[o]1 WKFHEWCOYQNAQR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/20—Hydroxylamino compounds or their ethers or esters having oxygen atoms of hydroxylamino groups etherified
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/825—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups all hydroxy groups bound to the ring
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310195267.6A CN103342633B (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0719180.2A GB0719180D0 (en) | 2007-10-02 | 2007-10-02 | New process |
| GB0719180.2 | 2007-10-02 | ||
| PCT/GB2008/003341 WO2009044143A2 (en) | 2007-10-02 | 2008-10-02 | Process for preparing benzofurans |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011102205750A Division CN102382086A (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
| CN201310195267.6A Division CN103342633B (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101861308A CN101861308A (zh) | 2010-10-13 |
| CN101861308B true CN101861308B (zh) | 2013-06-19 |
Family
ID=38738973
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011102205750A Pending CN102382086A (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
| CN201310195267.6A Expired - Fee Related CN103342633B (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
| CN2008801163899A Expired - Fee Related CN101861308B (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011102205750A Pending CN102382086A (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
| CN201310195267.6A Expired - Fee Related CN103342633B (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8519165B2 (enExample) |
| EP (3) | EP2200993B1 (enExample) |
| JP (2) | JP5577252B2 (enExample) |
| CN (3) | CN102382086A (enExample) |
| BR (1) | BRPI0817423A2 (enExample) |
| ES (3) | ES2589011T3 (enExample) |
| GB (1) | GB0719180D0 (enExample) |
| PL (3) | PL2636670T3 (enExample) |
| WO (1) | WO2009044143A2 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN102171200B (zh) * | 2008-10-02 | 2015-09-30 | 坎布雷卡尔斯库加公司 | 用于制备二酮类和药物的方法 |
| EA201100620A1 (ru) * | 2008-10-10 | 2011-12-30 | Лонца Лтд | Способ получения 2-алкил-3-ароил-5-нитробензофуранов |
| RU2520748C2 (ru) | 2008-12-04 | 2014-06-27 | Санофи | Способы и применения, включающие гемсвязывающий белок 1 |
| WO2010096871A1 (en) | 2009-02-25 | 2010-09-02 | Applied Hybrid Energy Pty Ltd | Carbon capture |
| CN102459154B (zh) * | 2009-04-08 | 2015-12-02 | 坎布雷卡尔斯库加公司 | 用于制备羟胺类和药物的新方法 |
| TW201107303A (en) | 2009-05-27 | 2011-03-01 | Sanofi Aventis | Process for the production of benzofurans |
| UY32657A (es) * | 2009-05-27 | 2010-12-31 | Sanofi Aventis | Procedimiento para la fabricación de productos intermedios de dronedarona |
| IT1398317B1 (it) * | 2010-02-23 | 2013-02-22 | Chimico Internaz Spa Lab | Nuovo procedimento per la preparazione del 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 |
| HUP1000330A2 (en) | 2010-06-18 | 2011-12-28 | Sanofi Sa | Process for the preparation of dronedarone and the novel intermediates |
| US20120005128A1 (en) * | 2010-06-29 | 2012-01-05 | Sanofi | Methods for reducing the risk of an adverse dronedarone / calcium channel blockers interaction in a patient suffering from atrial fibrilation |
| 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 |
| 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 |
| EP2452938A1 (en) | 2010-11-12 | 2012-05-16 | LEK Pharmaceuticals d.d. | Process for the preparation of 3-aroyl-5-aminobenzofuran derivatives |
| CN102070580B (zh) * | 2011-01-19 | 2015-05-20 | 上海医药工业研究院 | 2-正丁基-3-(4-(3-二正丁基氨基丙氧基)苯甲酰基)-5-取代氨基苯并呋喃的制备 |
| CN102070581B (zh) * | 2011-01-19 | 2015-11-25 | 上海医药工业研究院 | 2-正丁基-3-(4-(3-二正丁基氨基丙氧基)苯甲酰基)-5-氨基苯并呋喃的制备 |
| CN102070577B (zh) * | 2011-01-19 | 2016-03-09 | 上海医药工业研究院 | 2-正丁基-3-(4-取代丙氧基苯甲酰基)-5-取代氨基苯并呋喃及其应用 |
| CN102070578B (zh) * | 2011-01-19 | 2015-10-14 | 上海医药工业研究院 | 2-正丁基-3-(4-(3-二正丁基氨基丙氧基)苯甲酰基)-5-烷酰基氨基苯并呋喃的制备方法 |
| 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 |
| FR2973027A1 (fr) * | 2011-03-24 | 2012-09-28 | Sanofi Aventis | Procede de synthese de derives de cetobenzofurane |
| 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 |
| WO2013014480A1 (en) * | 2011-07-26 | 2013-01-31 | Sanofi | Process for preparation of dronedarone using amide intermediary compound |
| 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 |
| WO2013121234A1 (en) | 2012-02-14 | 2013-08-22 | Sanofi | Process for the preparation of dronedarone by oxidation of a sulphenyl group |
| WO2013124745A1 (en) | 2012-02-22 | 2013-08-29 | Sanofi | Process for preparation of dronedarone by oxidation of a hydroxyl group |
| CN102690250A (zh) * | 2012-05-08 | 2012-09-26 | 郑州明泽医药科技有限公司 | 决奈达隆中间体及其制备方法 |
| US9238636B2 (en) | 2012-05-31 | 2016-01-19 | Sanofi | Process for preparation of dronedarone by Grignard reaction |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0270342A2 (en) * | 1986-12-02 | 1988-06-08 | Tanabe Seiyaku Co., Ltd. | A benzo-furan (or -thiophene) derivative and processes for preparing the same |
| CN1479735A (zh) * | 2000-12-11 | 2004-03-03 | ʥŵ��-�ϳ�ʵ���ҹ�˾ | 甲基磺酰胺基-苯并呋喃衍生物,它的制备方法与它作为合成中间体的应用 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3340300A (en) * | 1964-10-05 | 1967-09-05 | American Cyanamid Co | Trimethoxy benzoylacetaldehyde oximes |
| US3558667A (en) * | 1968-11-01 | 1971-01-26 | Sterling Drug Inc | Benzofurans from o-phenyl ketoximes |
| JPS60169446A (ja) | 1984-02-15 | 1985-09-02 | Mitsui Petrochem Ind Ltd | ニトロフエノキシアミン類の製造方法 |
| JP2982130B2 (ja) * | 1990-02-06 | 1999-11-22 | ダイセル化学工業株式会社 | β−ケトアミド合成用触媒およびβ−ケトアミドの製造方法 |
| KR0168056B1 (ko) * | 1990-04-26 | 1999-03-20 | 베르너 발데크 | 선형 1,3-디케톤의 제조방법 |
| 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. |
| DE4244390A1 (de) * | 1992-12-29 | 1994-06-30 | Basf Ag | Verfahren zur Herstellung von Oximino-Derivaten und neue Oximino-Derivate |
| GB9416219D0 (en) | 1994-08-11 | 1994-10-05 | Karobio Ab | Receptor ligands |
| FR2746013B1 (fr) | 1996-03-18 | 1998-05-29 | Sanofi Sa | Utilisation de composes antiarythmiques dans la prevention de la mortalite post infarctus |
| AU6320998A (en) * | 1997-02-21 | 1998-09-09 | Bristol-Myers Squibb Company | Benzoic acid derivatives and related compounds as antiarrhythmic agents |
| FR2764800B1 (fr) | 1997-06-23 | 1999-09-10 | Sanofi Sa | Composition pharmaceutique solide contenant des derives de benzofuranne |
| GB9817118D0 (en) * | 1998-08-07 | 1998-10-07 | Glaxo Group Ltd | Pharmaceutical compounds |
| 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 |
| US6687428B2 (en) | 2000-09-21 | 2004-02-03 | Tera Op (Usa) Inc. | Optical switch |
| 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 |
| FR2817750B1 (fr) | 2000-12-11 | 2003-02-21 | Sanofi Synthelabo | Composition pharmaceutique de dronedarone pour administration parenterale |
| JP2004517954A (ja) * | 2001-02-02 | 2004-06-17 | ロシュ ビタミン アーゲー | 1,3−ジケトンの精製方法 |
| JP2002371076A (ja) * | 2001-06-14 | 2002-12-26 | Sumitomo Seika Chem Co Ltd | 2−アルキル−3−アシルベンゾフラン類の製造方法 |
| IL146389A0 (en) * | 2001-11-08 | 2002-07-25 | Isp Finetech Ltd | Process for the preparation of dronedarone |
| 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 |
| US7947707B2 (en) * | 2005-10-07 | 2011-05-24 | Kissei Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic compound and pharmaceutical composition comprising the same |
| GB0611210D0 (en) | 2006-06-07 | 2006-07-19 | Cambrex Karlskoga Ab | Process |
| 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 |
| CN100560067C (zh) | 2006-09-29 | 2009-11-18 | 北京德众万全药物技术开发有限公司 | 盐酸决奈达隆口服药物组合物及其制备方法 |
| GB0719180D0 (en) | 2007-10-02 | 2007-11-14 | Cambrex Karlskoga Ab | New process |
| CN102171200B (zh) | 2008-10-02 | 2015-09-30 | 坎布雷卡尔斯库加公司 | 用于制备二酮类和药物的方法 |
-
2007
- 2007-10-02 GB GBGB0719180.2A patent/GB0719180D0/en not_active Ceased
-
2008
- 2008-10-02 EP EP08806486A patent/EP2200993B1/en not_active Not-in-force
- 2008-10-02 WO PCT/GB2008/003341 patent/WO2009044143A2/en not_active Ceased
- 2008-10-02 ES ES13167925.0T patent/ES2589011T3/es active Active
- 2008-10-02 CN CN2011102205750A patent/CN102382086A/zh active Pending
- 2008-10-02 EP EP13167925.0A patent/EP2636670B1/en not_active Not-in-force
- 2008-10-02 ES ES08806486T patent/ES2395174T3/es active Active
- 2008-10-02 PL PL13167925.0T patent/PL2636670T3/pl unknown
- 2008-10-02 EP EP11075168.2A patent/EP2388256B1/en not_active Not-in-force
- 2008-10-02 CN CN201310195267.6A patent/CN103342633B/zh not_active Expired - Fee Related
- 2008-10-02 PL PL11075168T patent/PL2388256T3/pl unknown
- 2008-10-02 CN CN2008801163899A patent/CN101861308B/zh not_active Expired - Fee Related
- 2008-10-02 JP JP2010527524A patent/JP5577252B2/ja not_active Expired - Fee Related
- 2008-10-02 ES ES11075168.2T patent/ES2559939T3/es active Active
- 2008-10-02 PL PL08806486T patent/PL2200993T3/pl unknown
- 2008-10-02 BR BRPI0817423-7A patent/BRPI0817423A2/pt not_active IP Right Cessation
- 2008-10-02 US US12/681,299 patent/US8519165B2/en not_active Expired - Fee Related
-
2013
- 2013-07-18 US US13/944,950 patent/US8779201B2/en not_active Expired - Fee Related
-
2014
- 2014-06-04 JP JP2014115816A patent/JP5943965B2/ja not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0270342A2 (en) * | 1986-12-02 | 1988-06-08 | Tanabe Seiyaku Co., Ltd. | A benzo-furan (or -thiophene) derivative and processes for preparing the same |
| CN1479735A (zh) * | 2000-12-11 | 2004-03-03 | ʥŵ��-�ϳ�ʵ���ҹ�˾ | 甲基磺酰胺基-苯并呋喃衍生物,它的制备方法与它作为合成中间体的应用 |
Non-Patent Citations (4)
| Title |
|---|
| Daniel Lim, et al..Direct Carbon-Carbon Bond Formation via Soft Enolization: A Facile and Efficient Synthesis of 1,3-Diketones.《Org. Lett.》.2007,第9卷(第21期),4139-4142. * |
| DanielLim et al..Direct Carbon-Carbon Bond Formation via Soft Enolization: A Facile and Efficient Synthesis of 1 |
| N. Takeda, et al..Efficient Synthesis of Benzofurans Utilizing [3,3]-Sigmatropic Rearrangement Triggered by N-Trifluoroacetylation of Oxime Ethers: Short Synthesis of Natural 2-Arylbenzofurans.《Eur. J. Org. Chem.》.2007,1491-1509. * |
| N.Takeda et al..Efficient Synthesis of Benzofurans Utilizing [3 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102382086A (zh) | 2012-03-21 |
| PL2388256T3 (pl) | 2016-06-30 |
| ES2589011T3 (es) | 2016-11-08 |
| EP2388256A1 (en) | 2011-11-23 |
| JP2010540608A (ja) | 2010-12-24 |
| EP2388256B1 (en) | 2015-11-25 |
| JP5943965B2 (ja) | 2016-07-05 |
| JP2014208660A (ja) | 2014-11-06 |
| WO2009044143A2 (en) | 2009-04-09 |
| PL2200993T3 (pl) | 2013-01-31 |
| EP2200993B1 (en) | 2012-08-29 |
| CN103342633A (zh) | 2013-10-09 |
| HK1185611A1 (en) | 2014-02-21 |
| US8779201B2 (en) | 2014-07-15 |
| US8519165B2 (en) | 2013-08-27 |
| ES2559939T3 (es) | 2016-02-16 |
| GB0719180D0 (en) | 2007-11-14 |
| CN103342633B (zh) | 2016-05-04 |
| BRPI0817423A2 (pt) | 2015-06-16 |
| JP5577252B2 (ja) | 2014-08-20 |
| EP2200993A2 (en) | 2010-06-30 |
| WO2009044143A4 (en) | 2009-09-11 |
| ES2395174T3 (es) | 2013-02-08 |
| HK1145684A1 (en) | 2011-04-29 |
| US20130338398A1 (en) | 2013-12-19 |
| CN101861308A (zh) | 2010-10-13 |
| EP2636670B1 (en) | 2016-06-01 |
| HK1164303A1 (en) | 2012-09-21 |
| PL2636670T3 (pl) | 2016-12-30 |
| WO2009044143A3 (en) | 2009-06-25 |
| US20100292319A1 (en) | 2010-11-18 |
| EP2636670A1 (en) | 2013-09-11 |
| EP2388256A3 (en) | 2012-03-21 |
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