JP2008169225A5 - - Google Patents
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- Publication number
- JP2008169225A5 JP2008169225A5 JP2008060163A JP2008060163A JP2008169225A5 JP 2008169225 A5 JP2008169225 A5 JP 2008169225A5 JP 2008060163 A JP2008060163 A JP 2008060163A JP 2008060163 A JP2008060163 A JP 2008060163A JP 2008169225 A5 JP2008169225 A5 JP 2008169225A5
- Authority
- JP
- Japan
- Prior art keywords
- aralkyloxypyrrolidine
- benzyloxypyrrolidine
- derivative
- protected
- producing
- 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.)
- Pending
Links
- 239000013078 crystal Substances 0.000 claims description 46
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910001507 metal halide Inorganic materials 0.000 claims 2
- 150000005309 metal halides Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- -1 N-protected-3-hydroxypyrrolidine Chemical class 0.000 claims 1
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical group CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000003444 phase transfer catalyst Substances 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
- 235000019445 benzyl alcohol Nutrition 0.000 description 16
- 239000012141 concentrate Substances 0.000 description 12
- 239000012535 impurity Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- JHHZLHWJQPUNKB-SCSAIBSYSA-N (3r)-pyrrolidin-3-ol Chemical compound O[C@@H]1CCNC1 JHHZLHWJQPUNKB-SCSAIBSYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- CWBMYKUPMLRKQK-LLVKDONJSA-N (3r)-3-phenylmethoxypyrrolidine Chemical compound C=1C=CC=CC=1CO[C@@H]1CCNC1 CWBMYKUPMLRKQK-LLVKDONJSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000003796 beauty Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000007769 metal material Substances 0.000 description 4
- FRKGSNOMLIYPSH-GSVOUGTGSA-N (3r)-3-hydroxypyrrolidin-2-one Chemical compound O[C@@H]1CCNC1=O FRKGSNOMLIYPSH-GSVOUGTGSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- LDGGKPLLUKFIHV-RFVHGSKJSA-N (3r)-3-phenylmethoxypyrrolidine;hydrobromide Chemical compound Br.C=1C=CC=CC=1CO[C@@H]1CCNC1 LDGGKPLLUKFIHV-RFVHGSKJSA-N 0.000 description 2
- HSYANDXYTBIRPP-RFVHGSKJSA-N (3r)-3-phenylmethoxypyrrolidine;sulfuric acid Chemical compound OS(O)(=O)=O.C=1C=CC=CC=1CO[C@@H]1CCNC1 HSYANDXYTBIRPP-RFVHGSKJSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- PAQGUMZPOPIQIE-RFVHGSKJSA-N 4-methylbenzenesulfonic acid;(3r)-3-phenylmethoxypyrrolidine Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C=1C=CC=CC=1CO[C@@H]1CCNC1 PAQGUMZPOPIQIE-RFVHGSKJSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- POUFTKPCKYNBNN-JZSAPEFASA-N N[C@@H](CC(=O)O)C(=O)O.C(C1=CC=CC=C1)O[C@H]1CNCC1 Chemical compound N[C@@H](CC(=O)O)C(=O)O.C(C1=CC=CC=C1)O[C@H]1CNCC1 POUFTKPCKYNBNN-JZSAPEFASA-N 0.000 description 2
- POUFTKPCKYNBNN-OYUHWNLBSA-N N[C@H](CC(=O)O)C(=O)O.C(C1=CC=CC=C1)O[C@H]1CNCC1 Chemical compound N[C@H](CC(=O)O)C(=O)O.C(C1=CC=CC=C1)O[C@H]1CNCC1 POUFTKPCKYNBNN-OYUHWNLBSA-N 0.000 description 2
- ODGFHDKFXHIRGF-IMWLJMTPSA-N OC(=O)[C@@H](O)[C@H](O)C(O)=O.C=1C=CC=CC=1CO[C@@H]1CCNC1 Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O.C=1C=CC=CC=1CO[C@@H]1CCNC1 ODGFHDKFXHIRGF-IMWLJMTPSA-N 0.000 description 2
- ODGFHDKFXHIRGF-VUAFVNRWSA-N OC(=O)[C@H](O)[C@@H](O)C(O)=O.C=1C=CC=CC=1CO[C@@H]1CCNC1 Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.C=1C=CC=CC=1CO[C@@H]1CCNC1 ODGFHDKFXHIRGF-VUAFVNRWSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- NWDGDDMXWPHGTF-RFVHGSKJSA-N benzoic acid;(3r)-3-phenylmethoxypyrrolidine Chemical compound OC(=O)C1=CC=CC=C1.C=1C=CC=CC=1CO[C@@H]1CCNC1 NWDGDDMXWPHGTF-RFVHGSKJSA-N 0.000 description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical class OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- SNDPVESSAGLHJB-CQSZACIVSA-N tert-butyl (3r)-3-phenylmethoxypyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@H]1OCC1=CC=CC=C1 SNDPVESSAGLHJB-CQSZACIVSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- GOLSNGZZFJTKQD-SNVBAGLBSA-N (3R)-3-phenylmethoxypyrrolidin-2-one Chemical compound O=C1NCC[C@H]1OCc1ccccc1 GOLSNGZZFJTKQD-SNVBAGLBSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- KJXBOETWBRQJFK-UHFFFAOYSA-N 1-phenylmethoxypyrrolidine Chemical compound C=1C=CC=CC=1CON1CCCC1 KJXBOETWBRQJFK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- YOIUWLBWALBKBJ-ASTHLYEOSA-N C(C)(C)(C)OC(=O)N1C[C@@H](CC1)O.C(C)(C)(C)OC(=O)N1C[C@@H](CC1)OCC1=CC=CC=C1 Chemical compound C(C)(C)(C)OC(=O)N1C[C@@H](CC1)O.C(C)(C)(C)OC(=O)N1C[C@@H](CC1)OCC1=CC=CC=C1 YOIUWLBWALBKBJ-ASTHLYEOSA-N 0.000 description 1
- 101000717863 Sporidiobolus salmonicolor Aldehyde reductase 2 Proteins 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- APCBTRDHCDOPNY-SSDOTTSWSA-N tert-butyl (3r)-3-hydroxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](O)C1 APCBTRDHCDOPNY-SSDOTTSWSA-N 0.000 description 1
- YVZFGLMFJYDGAK-AWEZNQCLSA-N tert-butyl N-[(3S)-3-phenylmethoxypyrrolidin-1-yl]carbamate Chemical compound C1N(NC(=O)OC(C)(C)C)CC[C@@H]1OCC1=CC=CC=C1 YVZFGLMFJYDGAK-AWEZNQCLSA-N 0.000 description 1
- ZZJCAPFEPWXMSG-UHFFFAOYSA-N tert-butyl n-(3-hydroxypyrrolidin-1-yl)carbamate Chemical compound CC(C)(C)OC(=O)NN1CCC(O)C1 ZZJCAPFEPWXMSG-UHFFFAOYSA-N 0.000 description 1
- YVZFGLMFJYDGAK-UHFFFAOYSA-N tert-butyl n-(3-phenylmethoxypyrrolidin-1-yl)carbamate Chemical compound C1N(NC(=O)OC(C)(C)C)CCC1OCC1=CC=CC=C1 YVZFGLMFJYDGAK-UHFFFAOYSA-N 0.000 description 1
- YVZFGLMFJYDGAK-CQSZACIVSA-N tert-butyl n-[(3r)-3-phenylmethoxypyrrolidin-1-yl]carbamate Chemical compound C1N(NC(=O)OC(C)(C)C)CC[C@H]1OCC1=CC=CC=C1 YVZFGLMFJYDGAK-CQSZACIVSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008060163A JP2008169225A (ja) | 2005-08-23 | 2008-03-10 | ３−アラルキルオキシピロリジン誘導体の製造法 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005241742 | 2005-08-23 | ||
| JP2008060163A JP2008169225A (ja) | 2005-08-23 | 2008-03-10 | ３−アラルキルオキシピロリジン誘導体の製造法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007532139A Division JP4167297B2 (ja) | 2005-08-23 | 2006-08-22 | ３−アラルキルオキシピロリジン誘導体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008169225A JP2008169225A (ja) | 2008-07-24 |
| JP2008169225A5 true JP2008169225A5 (https=) | 2008-09-04 |
Family
ID=37771567
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007532139A Expired - Fee Related JP4167297B2 (ja) | 2005-08-23 | 2006-08-22 | ３−アラルキルオキシピロリジン誘導体の製造法 |
| JP2008060163A Pending JP2008169225A (ja) | 2005-08-23 | 2008-03-10 | ３−アラルキルオキシピロリジン誘導体の製造法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007532139A Expired - Fee Related JP4167297B2 (ja) | 2005-08-23 | 2006-08-22 | ３−アラルキルオキシピロリジン誘導体の製造法 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7973176B2 (https=) |
| EP (1) | EP1947083B1 (https=) |
| JP (2) | JP4167297B2 (https=) |
| DE (1) | DE602006018182D1 (https=) |
| WO (1) | WO2007023824A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009122997A1 (ja) * | 2008-04-02 | 2009-10-08 | 株式会社カネカ | （ｓ）－３－（１－シアノ－１，１－ジフェニルメチル）－ピロリジンの製造法 |
| CN102633704A (zh) * | 2012-03-28 | 2012-08-15 | 扬州天和药业有限公司 | R-4-苄氧吡咯烷的一种制备方法 |
| CN104610122A (zh) * | 2015-02-06 | 2015-05-13 | 中国药科大学 | 反-2-[(3r)-3-苄氧基-1-吡咯烷基]-1-环己醇的制备方法 |
| AU2017297505B2 (en) * | 2016-07-13 | 2020-09-17 | DAJW Investments II, Ltd. | Band-pass filter |
| CA3032047C (en) | 2016-07-27 | 2025-07-08 | Synergetic Oil Tools, Inc. | DEVICES AND METHODS FOR INCREASING THE SOLUBILITY OF CRYSTALS IN WATER |
| US12258285B2 (en) | 2016-07-27 | 2025-03-25 | Synergetic Oil Tools, Inc. | Device and methods for increasing the solubility of crystals in water, rheology data |
| CN108203517B (zh) * | 2017-06-26 | 2021-03-30 | 哈尔滨工业大学（威海） | 一种芳香聚合物材料表面接枝阳离子抑菌涂层的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60178837A (ja) * | 1984-02-24 | 1985-09-12 | Yamanouchi Pharmaceut Co Ltd | カテコ−ル誘導体 |
| ES8505914A1 (es) * | 1983-05-13 | 1985-06-16 | Yamanouchi Pharma Co Ltd | Un procedimiento para la produccion de un derivado de catecol |
| JPS61243081A (ja) * | 1985-04-19 | 1986-10-29 | Dainippon Pharmaceut Co Ltd | ピリドンカルボン酸誘導体、そのエステルおよびその塩 |
| AU578793B2 (en) * | 1985-02-15 | 1988-11-03 | Dainippon Pharmaceutical Co. Ltd. | Novel 1,8-naphthyridine derivatives and processes for preparation thereof |
| DE3835291A1 (de) * | 1988-04-19 | 1989-11-02 | Bayer Ag | 1,3-disubstituierte pyrrolidine |
| CA2195107A1 (en) * | 1994-08-02 | 1996-02-15 | Richard Alexander Jelley | Azetidine, pyrrolidine and piperidine derivatives |
| JPH10109976A (ja) * | 1996-04-26 | 1998-04-28 | Ishihara Sangyo Kaisha Ltd | ピラゾール系化合物、それらの製造方法及びそれらを含有する除草剤 |
| AR006793A1 (es) * | 1996-04-26 | 1999-09-29 | Ishihara Sangyo Kaisha | Compuestos pirazol o sus sales y herbicidas conteniendo los mismos |
| DE60333741D1 (de) * | 2002-03-29 | 2010-09-23 | Kaneka Corp | Verfahren zum erhöhen der optischen reinheit von 1-benzyl-3-aminopyrrolidin und salz, das sich dabei verwenden lässt |
| CA2524323C (en) * | 2003-05-02 | 2012-05-15 | Cardiome Pharma Corp. | Aminocyclohexyl ether compounds and uses thereof |
-
2006
- 2006-08-22 WO PCT/JP2006/316435 patent/WO2007023824A1/ja not_active Ceased
- 2006-08-22 JP JP2007532139A patent/JP4167297B2/ja not_active Expired - Fee Related
- 2006-08-22 EP EP06796649A patent/EP1947083B1/en active Active
- 2006-08-22 US US11/990,766 patent/US7973176B2/en not_active Expired - Fee Related
- 2006-08-22 DE DE602006018182T patent/DE602006018182D1/de active Active
-
2008
- 2008-03-10 JP JP2008060163A patent/JP2008169225A/ja active Pending
-
2011
- 2011-05-25 US US13/115,385 patent/US8247578B2/en not_active Expired - Fee Related
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