ES2492918T3 - Procedimiento para la preparación catalítica de nitrilos aromáticos o heteroaromáticos - Google Patents
Procedimiento para la preparación catalítica de nitrilos aromáticos o heteroaromáticos Download PDFInfo
- Publication number
- ES2492918T3 ES2492918T3 ES07115366.2T ES07115366T ES2492918T3 ES 2492918 T3 ES2492918 T3 ES 2492918T3 ES 07115366 T ES07115366 T ES 07115366T ES 2492918 T3 ES2492918 T3 ES 2492918T3
- Authority
- ES
- Spain
- Prior art keywords
- aromatic
- procedure
- catalytic preparation
- heteroaromatic
- heteroaromatic nitriles
- 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.)
- Active
Links
- 125000003118 aryl group Chemical group 0.000 title abstract 3
- 230000003197 catalytic effect Effects 0.000 title abstract 2
- -1 heteroaromatic nitriles Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- UETZVSHORCDDTH-UHFFFAOYSA-N iron(2+);hexacyanide Chemical compound [Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UETZVSHORCDDTH-UHFFFAOYSA-N 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- 150000001502 aryl halides Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 239000011630 iodine Chemical group 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 6
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 description 5
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
- RXNZFHIEDZEUQM-UHFFFAOYSA-N 2-bromo-1,3-thiazole Chemical compound BrC1=NC=CS1 RXNZFHIEDZEUQM-UHFFFAOYSA-N 0.000 description 2
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 2
- RWXUNIMBRXGNEP-UHFFFAOYSA-N 1-bromo-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Br RWXUNIMBRXGNEP-UHFFFAOYSA-N 0.000 description 1
- CSVCVIHEBDJTCJ-UHFFFAOYSA-N 1-bromo-3,5-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Br)=CC(C(F)(F)F)=C1 CSVCVIHEBDJTCJ-UHFFFAOYSA-N 0.000 description 1
- ZDFBKZUDCQQKAC-UHFFFAOYSA-N 1-bromo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1 ZDFBKZUDCQQKAC-UHFFFAOYSA-N 0.000 description 1
- AEJOEPSMZCEYJN-HXUWFJFHSA-N 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl]acetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C(Cl)C(Cl)=CC=1)C=1C=CC=CC=1)N1CCCC1 AEJOEPSMZCEYJN-HXUWFJFHSA-N 0.000 description 1
- MYMYVYZLMUEVED-UHFFFAOYSA-N 2-bromo-1,3-dimethylbenzene Chemical group CC1=CC=CC(C)=C1Br MYMYVYZLMUEVED-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- KXSQMCRVUAALNE-UHFFFAOYSA-N 3-bromo-5-fluoropyridin-2-amine Chemical compound NC1=NC=C(F)C=C1Br KXSQMCRVUAALNE-UHFFFAOYSA-N 0.000 description 1
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 1
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Procedimiento para la preparación catalítica de nitrilos aromáticos o heteroaromáticos dado el caso sustituidos, de fórmula general (I) Ar-CN (I) mediante reacción de los halogenuros de arilo correspondientes de fórmula general (II) Ar-X (II) en la que X representa cloro, bromo, yodo o sulfonato, y Ar representa un resto aromático o heteroaromático dado el caso sustituido, caracterizado por que la reacción se lleva a cabo en presencia de compuestos de cobre y de 1-alquilimidazoles y como donador de cianuro se utiliza hexacianoferrato de potasio (II) o hexacianoferrato de potasio (III).
Description
-
- 3.
- 1-bromo-4-nitrobenceno 80 (1-butilmidazol)
- 4.
- 2amino-5-bromopiridina 55 (1-metilimidazol)
- 5.
- 2-bromo-m-xileno 66 (180°C); (1-metilimidazol)
- 6.
- 3,5-Bis(trifluorometil)-bromobenceno 98 (1-butilimidazol) 68 (1-metilimidazol, 0,05 equivalentes de CuI) 52 (1-butilimidazol, 0,02 equivalentes de. CuI) 29 (1-butilimidazol, 0,02 equivalentes de CuBr)
- 7.
- 2-bromobenzotrifluoruro 83 (1-butilimidazol)
- 8.
- 2-amino-3-bromo-5-fluoropiridina 93 (1-metilimidazol)
- 9.
- 5-bromopiridina 95 (1-butilimidazol) 82 (1-metilimidazol, 0,05 equivalentes de CuI)
- 10.
- 2-bromotiazol 99 (1-metilimidazol)
- Sustrato
- Disolvente Temperatura [ºC] Etapa previa de metal1 Aditivos1 Ligando1 Rendimiento [%]
- 2-Bromotiazol
- NMP 140 CuI 10 % Na2CO3 20 % KI 20 % DMEDA 100 % 0
- NMP
- 140 Pd(OAc)20,1 % Na2CO3 20 % dppf 0,2 % 0
- 1-Metil-imidazol
- 140 CuI 10 % - - 99
- 2-Bromopiridina
- NMP 130 Pd(OAc)2 0,5 % Na2CO3 20 % dppf3 2 % 30
- NMP
- 110 Na2CO3 20 % dppf 1 % 0
- NMP
- 140 Na2CO3 20 % dppf 1 % < 5
- NMP
- 160 Na2CO3 20 % KI 20 % DMEDA 100 % 0
- 1-metil-imidazol
- 140 CuI 10 % - - 100
- 3 dppf = 1,1’-bis-(difenilfosfino)-propano
Claims (1)
-
imagen1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006042439 | 2006-09-09 | ||
| DE102006042439A DE102006042439A1 (de) | 2006-09-09 | 2006-09-09 | Verfahren zur katalytischen Herstellung von aromatischen oder heteroaromatischen Nitrilen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2492918T3 true ES2492918T3 (es) | 2014-09-10 |
Family
ID=38924443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07115366.2T Active ES2492918T3 (es) | 2006-09-09 | 2007-08-31 | Procedimiento para la preparación catalítica de nitrilos aromáticos o heteroaromáticos |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7592452B2 (es) |
| EP (1) | EP1903030B1 (es) |
| JP (1) | JP5235366B2 (es) |
| DE (1) | DE102006042439A1 (es) |
| ES (1) | ES2492918T3 (es) |
| PL (1) | PL1903030T3 (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI432421B (zh) | 2007-12-19 | 2014-04-01 | Du Pont | 製備２－胺基－５－氰基苯甲酸衍生物之方法 |
| TWI431000B (zh) * | 2008-03-05 | 2014-03-21 | Du Pont | 製備２－胺基－５－氰基苯甲酸衍生物之方法 |
| CN101671300B (zh) * | 2009-09-28 | 2011-04-13 | 南京第一农药集团有限公司 | 一种2-氰基-3,6-二氯吡啶的制备方法 |
| CN102381918B (zh) * | 2011-08-31 | 2014-03-26 | 河南科技大学 | 一种由苄氯类化合物合成苯乙腈类化合物的方法 |
| GB201118876D0 (en) | 2011-11-01 | 2011-12-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| CN102408378A (zh) * | 2012-01-06 | 2012-04-11 | 盛世泰科生物医药技术(苏州)有限公司 | 一种5-氰基嘧啶的合成方法 |
| JP6333251B2 (ja) | 2012-08-16 | 2018-05-30 | バイエル ファーマ アクチエンゲゼルシャフト | ２，３−ベンゾジアゼピン類 |
| CN102898264B (zh) * | 2012-09-12 | 2014-07-02 | 浙江大学 | 一种芳香腈或杂芳腈的催化制备工艺 |
| CN107903190A (zh) * | 2017-12-14 | 2018-04-13 | 郑州盖科科技有限公司 | 一种对叔丁基邻苯二甲腈的制备方法 |
| CN109369563A (zh) * | 2018-12-10 | 2019-02-22 | 白东跃 | 一种医药中间体2-氰基噻唑的制备方法 |
| CN114380713B (zh) * | 2021-09-29 | 2024-10-08 | 辽宁众辉生物科技有限公司 | 邻甲基苯甲酰氰合成方法 |
| AR129265A1 (es) | 2022-05-12 | 2024-08-07 | Syngenta Crop Protection Ag | Compuestos de alcoxi-heteroaril-carboxamida o tioamida |
| CN115677522B (zh) * | 2022-10-31 | 2025-02-14 | 浙江巍华新材料股份有限公司 | 一种邻三氟甲基苯甲酰胺及其中间体的制备方法 |
| CN119954718B (zh) * | 2024-12-13 | 2025-11-18 | 上海合全药业股份有限公司 | 一种2-氰基吡啶类化合物的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE293094C (es) | ||||
| US4211721A (en) | 1978-12-04 | 1980-07-08 | Hooker Chemicals & Plastics Corp. | Process for the preparation of aromatic nitriles |
| JPS55120549A (en) * | 1979-03-09 | 1980-09-17 | Nippon Kayaku Co Ltd | Preparation of 2-chloro-6-nitrobenzonitrile |
| US4499025A (en) | 1982-04-23 | 1985-02-12 | Occidental Chemical Corporation | Electrochemical maintenance of catalyst activity |
| PL319692A1 (en) | 1994-10-17 | 1997-08-18 | Ciba Geigy Ag | Method of obtaining substituted 3-amino benzonitriles |
| DE19706648A1 (de) | 1997-02-20 | 1998-08-27 | Bayer Ag | Verfahren zur Herstellung von aromatischen Nitrilen |
| EP0994099B1 (en) | 1998-10-13 | 2005-02-02 | Bayer CropScience S.A. | Process for preparing 4-cyano-3-nitrobenzotrifluoride from 3-bromo-4-cyanobenzotrifluoride in the presence of catalytic cuprous cyanide and a phase transfer catalyst. |
| JP2000344732A (ja) * | 1999-03-29 | 2000-12-12 | Nissan Chem Ind Ltd | ベンゾニトリル化合物の製造法 |
| DE10113976A1 (de) | 2001-03-22 | 2002-09-26 | Degussa | Verfahren zur katalytischen Herstellung von aromatischen oder heteroaromatischen Nitrilen |
| DE10322408A1 (de) | 2003-05-16 | 2004-12-02 | Degussa Ag | Stickstoffhaltige monodentate Phosphine und deren Verwendung in der Katalyse |
| DE102005009517A1 (de) | 2005-02-28 | 2006-08-31 | Lanxess Deutschland Gmbh | Verfahren zur katalytischen Herstellung von aromatischen Nitrilen |
-
2006
- 2006-09-09 DE DE102006042439A patent/DE102006042439A1/de not_active Withdrawn
-
2007
- 2007-08-27 US US11/895,728 patent/US7592452B2/en not_active Expired - Fee Related
- 2007-08-31 ES ES07115366.2T patent/ES2492918T3/es active Active
- 2007-08-31 PL PL07115366T patent/PL1903030T3/pl unknown
- 2007-08-31 EP EP07115366.2A patent/EP1903030B1/de not_active Not-in-force
- 2007-09-10 JP JP2007234347A patent/JP5235366B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008063336A (ja) | 2008-03-21 |
| PL1903030T3 (pl) | 2014-11-28 |
| US20090062541A1 (en) | 2009-03-05 |
| EP1903030A1 (de) | 2008-03-26 |
| EP1903030B1 (de) | 2014-06-04 |
| DE102006042439A1 (de) | 2008-03-27 |
| US7592452B2 (en) | 2009-09-22 |
| JP5235366B2 (ja) | 2013-07-10 |
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