DE50015330D1 - Herstellung von n-substituierten 2,7-dialkyl-4-hydroxy-5-amino-8-aryl-octanoylamiden - Google Patents
Herstellung von n-substituierten 2,7-dialkyl-4-hydroxy-5-amino-8-aryl-octanoylamidenInfo
- Publication number
- DE50015330D1 DE50015330D1 DE50015330T DE50015330T DE50015330D1 DE 50015330 D1 DE50015330 D1 DE 50015330D1 DE 50015330 T DE50015330 T DE 50015330T DE 50015330 T DE50015330 T DE 50015330T DE 50015330 D1 DE50015330 D1 DE 50015330D1
- Authority
- DE
- Germany
- Prior art keywords
- sub
- alkyl
- alkoxy
- formula
- substituted
- 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 - Lifetime
Links
- 125000000217 alkyl group Chemical group 0.000 abstract 23
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000007245 halolactonization reaction Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000007142 ring opening reaction Methods 0.000 abstract 1
- -1 tetramethylene, pentamethylene, 3-oxa-1,5-pentylene Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/20—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
- C07C247/12—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH140199 | 1999-07-29 | ||
| CH442000 | 2000-01-11 | ||
| PCT/CH2000/000384 WO2001009083A1 (de) | 1999-07-29 | 2000-07-13 | Herstellung von n-substituierten 2,7-dialkyl-4-hydroxy-5-amino-8-aryl-octanoylamiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE50015330D1 true DE50015330D1 (de) | 2008-10-09 |
Family
ID=25687539
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50015330T Expired - Lifetime DE50015330D1 (de) | 1999-07-29 | 2000-07-13 | Herstellung von n-substituierten 2,7-dialkyl-4-hydroxy-5-amino-8-aryl-octanoylamiden |
| DE50006271T Expired - Lifetime DE50006271D1 (de) | 1999-07-29 | 2000-07-13 | 2-alkyl-5-halogen-pent-4-encarbonsäuren und deren herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50006271T Expired - Lifetime DE50006271D1 (de) | 1999-07-29 | 2000-07-13 | 2-alkyl-5-halogen-pent-4-encarbonsäuren und deren herstellung |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US7009078B1 (enExample) |
| EP (2) | EP1200384B1 (enExample) |
| JP (2) | JP4580606B2 (enExample) |
| AT (2) | ATE406346T1 (enExample) |
| AU (2) | AU5518400A (enExample) |
| DE (2) | DE50015330D1 (enExample) |
| DK (2) | DK1200384T3 (enExample) |
| ES (2) | ES2218173T3 (enExample) |
| PT (2) | PT1200390E (enExample) |
| WO (2) | WO2001009079A1 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL212898B1 (pl) | 2000-07-05 | 2012-12-31 | Speedel Pharma Ag | Sposób otrzymywania podstawionych amidów oktanoilowych oraz zwiazki posrednie wykorzystane w tym sposobie |
| EP1412514B1 (en) | 2001-05-15 | 2010-02-17 | Novartis Ag | Enzymatic process for the preparation of substituted carboxylic esters |
| AU2003238007A1 (en) * | 2002-06-11 | 2003-12-22 | Elan Pharmaceuticals, Inc. | Methods of treating alzheimer's disease using aryl alkanoic acid amides |
| ATE355263T1 (de) * | 2002-12-09 | 2006-03-15 | Asahi Glass Co Ltd | Verfahren zur herstellung von(4e)-5-chloro-2- isopropyl-4-pentensäureester und optischaktivem isomer davon |
| EP1626093A1 (en) * | 2004-08-11 | 2006-02-15 | Dow Global Technologies Inc. | Process for the production of (S)-5-chloro-2-isopropylpent-4-enoic acid esters |
| EA200701925A1 (ru) * | 2005-03-09 | 2008-02-28 | Дсм Файн Кемикалс Аустриа Нфг Гмбх Унд Ко Кг | Способ получения энантиомерночистых e-2(s)-алкил-5-галопент-4-еновых кислот и их сложных эфиров |
| ATE451345T1 (de) * | 2005-03-17 | 2009-12-15 | Basf Se | Verfahren zur herstellung von optisch aktiven 3- phenylpropionsäurederivaten und folgeprodukte davon |
| WO2006117057A1 (en) * | 2005-05-02 | 2006-11-09 | Dsm Fine Chemicals Austria Nfg Gmbh & Co Kg | Process for preparing enantiomerically enriched e-(2s)- and (2r)-alkyl-5-halopent-4-enecarboxylic acids or their esters |
| AT502257B1 (de) * | 2005-07-25 | 2007-04-15 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von racemischen alkyl-5-halogen-pent-4-en-carbonsäuren bzw. -carbonsäureestern |
| DE102005042458A1 (de) * | 2005-09-06 | 2007-03-22 | Basf Ag | Verfahren zur Herstellung von 2-substituierten Carbonsäuren |
| WO2007036491A1 (de) * | 2005-09-30 | 2007-04-05 | Basf Aktiengesellschaft | Verfahren zur herstellung von alpha-substituierten carbonsäuren |
| GB0521083D0 (en) | 2005-10-17 | 2005-11-23 | Novartis Ag | Organic compounds |
| GB2431654A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
| GB2431640A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
| DE102005052195A1 (de) | 2005-10-28 | 2007-05-03 | Reuter Chemischer Apparatebau Kg | Verfahren zur Herstellung von chiralen Octensäurederivaten |
| ES2439735T3 (es) * | 2005-12-16 | 2014-01-24 | Asahi Glass Company, Limited | Método para producir ácido (4E)-5-cloro-2-isopropil-4-pentenoico o una sal de aminoácido básico del mismo |
| TW200837046A (en) * | 2006-11-08 | 2008-09-16 | Speedel Experimenta Ag | Process for preparing organic compounds |
| EP1958666A1 (en) | 2007-02-13 | 2008-08-20 | Speedel Experimenta AG | Heterocyclic-substituted alkanamides as therapeutic compounds |
| DE102007049039A1 (de) | 2007-10-11 | 2009-04-16 | Reuter Chemischer Apparatebau Kg | Verfahren zur Herstellung von 8-Hydrazino-8-Aryl-Octanoylderivaten und deren Verwendung |
| EP2062874B1 (en) | 2007-11-20 | 2014-12-17 | KRKA, tovarna zdravil, d.d., Novo mesto | Process and intermediates for the preparation of aliskiren |
| EP2225200B1 (en) * | 2007-12-24 | 2013-10-16 | DSM IP Assets B.V. | Convergent synthesis of renin inhibitors and intermediates useful therein |
| JP2011520984A (ja) * | 2008-05-23 | 2011-07-21 | テバ ファーマシューティカル インダストリーズ リミティド | アリスキレンモノフマル酸塩及びその製造方法 |
| SI2189442T1 (sl) | 2008-11-20 | 2015-03-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Postopek in intermediati za pripravo aliskirena |
| EA201190091A1 (ru) | 2009-02-05 | 2012-01-30 | Крка, Товарна Здравил, Д. Д., Ново Место | Активируемый влагой способ грануляции |
| US8203005B2 (en) | 2009-10-29 | 2012-06-19 | Carbo Design Llc | Manufacturing process for enantiomerically pure 8-aryloctanoic acids as Aliskiren |
| CN101774986B (zh) | 2010-01-06 | 2012-03-28 | 浙江天宇药业股份有限公司 | 一种制备阿利克伦及其中间体的方法 |
| TR201002256A1 (tr) * | 2010-03-24 | 2011-10-21 | Sanovel �La� Sanay� Ve T�Caret Anon�M ��Rket� | Stabil aliskiren formülasyonları |
| US20110268797A1 (en) | 2010-04-30 | 2011-11-03 | Sanovel IIac Sanayi Ve Ticaret Anonim Sirketi | Multicoated aliskiren formulations |
| WO2012052829A1 (en) | 2010-10-19 | 2012-04-26 | Matrix Laboratories Ltd | Synthesis of aliskiren |
| US8703976B2 (en) | 2011-10-02 | 2014-04-22 | Milan Soukup | Manufacturing process for 8-aryloctanoic acids such as Aliskiren |
| WO2013118138A1 (en) | 2011-12-13 | 2013-08-15 | Laboratories Ltd Mylan | Novel process for the preparation of renin inhibitors |
| WO2013121443A1 (en) | 2012-02-17 | 2013-08-22 | Mylan Laboratories Ltd. | An improved process for the preparation of aliskiren |
| WO2013124868A2 (en) | 2012-02-21 | 2013-08-29 | Mylan Laboratories Limited | Solid form of aliskiren intermediate |
| WO2013144979A1 (en) | 2012-03-28 | 2013-10-03 | Maylan Laboratories Ltd | Process for the preparation of aliskiren |
| WO2013171767A1 (en) | 2012-05-18 | 2013-11-21 | Mylan Laboratories Limited | An improved process for the preparation of aliskiren |
| CN103130677B (zh) * | 2013-03-12 | 2015-01-07 | 博瑞生物医药技术(苏州)有限公司 | 一种阿利克仑的制备方法 |
| EP3013836B1 (en) * | 2013-06-27 | 2018-06-20 | Patheon Austria GmbH & Co KG | Preparation of grignard reagents using a fluidized bed |
| CN103351300A (zh) * | 2013-06-30 | 2013-10-16 | 北京万全德众医药生物技术有限公司 | 一种制备阿利克仑中间体侧链（s）-2-溴代异戊酸甲酯的方法 |
| CN105294478B (zh) * | 2014-07-01 | 2017-06-13 | 华润双鹤药业股份有限公司 | 阿利吉仑的一种非对映异构体、其制备方法及用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4492799A (en) * | 1979-07-02 | 1985-01-08 | Union Carbide Corporation | Halo-4-alkenoic acids and their use as pesticidal intermediates |
| US4291057A (en) * | 1979-07-02 | 1981-09-22 | Union Carbide Corporation | Biocidal esters of halo-4-alkenoic acids |
| MY119161A (en) * | 1994-04-18 | 2005-04-30 | Novartis Ag | Delta-amino-gamma-hydroxy-omega-aryl-alkanoic acid amides with enzyme especially renin inhibiting activities |
| US5952507A (en) * | 1997-03-10 | 1999-09-14 | Hoffmann La Roche | Process for manufacture of chiral succinic acid derivatives |
-
2000
- 2000-07-13 DK DK00940109T patent/DK1200384T3/da active
- 2000-07-13 AT AT00940108T patent/ATE406346T1/de active
- 2000-07-13 DE DE50015330T patent/DE50015330D1/de not_active Expired - Lifetime
- 2000-07-13 AT AT00940109T patent/ATE265415T1/de active
- 2000-07-13 PT PT00940108T patent/PT1200390E/pt unknown
- 2000-07-13 EP EP00940109A patent/EP1200384B1/de not_active Expired - Lifetime
- 2000-07-13 AU AU55184/00A patent/AU5518400A/en not_active Abandoned
- 2000-07-13 AU AU55185/00A patent/AU5518500A/en not_active Abandoned
- 2000-07-13 US US10/048,229 patent/US7009078B1/en not_active Expired - Fee Related
- 2000-07-13 JP JP2001514283A patent/JP4580606B2/ja not_active Expired - Lifetime
- 2000-07-13 US US10/048,290 patent/US6777574B1/en not_active Expired - Fee Related
- 2000-07-13 ES ES00940109T patent/ES2218173T3/es not_active Expired - Lifetime
- 2000-07-13 ES ES00940108T patent/ES2312346T3/es not_active Expired - Lifetime
- 2000-07-13 DE DE50006271T patent/DE50006271D1/de not_active Expired - Lifetime
- 2000-07-13 PT PT00940109T patent/PT1200384E/pt unknown
- 2000-07-13 EP EP00940108A patent/EP1200390B1/de not_active Expired - Lifetime
- 2000-07-13 JP JP2001514287A patent/JP4922521B2/ja not_active Expired - Fee Related
- 2000-07-13 DK DK00940108T patent/DK1200390T3/da active
- 2000-07-13 WO PCT/CH2000/000385 patent/WO2001009079A1/de not_active Ceased
- 2000-07-13 WO PCT/CH2000/000384 patent/WO2001009083A1/de not_active Ceased
-
2005
- 2005-10-21 US US11/254,749 patent/US7132569B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PT1200384E (pt) | 2004-09-30 |
| WO2001009079A1 (de) | 2001-02-08 |
| DK1200390T3 (da) | 2008-12-01 |
| AU5518400A (en) | 2001-02-19 |
| PT1200390E (pt) | 2008-12-05 |
| ATE265415T1 (de) | 2004-05-15 |
| US7132569B2 (en) | 2006-11-07 |
| WO2001009083A1 (de) | 2001-02-08 |
| EP1200384B1 (de) | 2004-04-28 |
| EP1200390A1 (de) | 2002-05-02 |
| DK1200384T3 (da) | 2004-08-02 |
| JP4580606B2 (ja) | 2010-11-17 |
| AU5518500A (en) | 2001-02-19 |
| JP4922521B2 (ja) | 2012-04-25 |
| ES2312346T3 (es) | 2009-03-01 |
| EP1200390B1 (de) | 2008-08-27 |
| JP2003506347A (ja) | 2003-02-18 |
| DE50006271D1 (de) | 2004-06-03 |
| EP1200384A1 (de) | 2002-05-02 |
| US7009078B1 (en) | 2006-03-07 |
| US20060041169A1 (en) | 2006-02-23 |
| ATE406346T1 (de) | 2008-09-15 |
| ES2218173T3 (es) | 2004-11-16 |
| JP2003506345A (ja) | 2003-02-18 |
| US6777574B1 (en) | 2004-08-17 |
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