RU2007125687A - Способ получения хиральных 1,4-дизамещенных пиперазинов - Google Patents
Способ получения хиральных 1,4-дизамещенных пиперазинов Download PDFInfo
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- RU2007125687A RU2007125687A RU2007125687/04A RU2007125687A RU2007125687A RU 2007125687 A RU2007125687 A RU 2007125687A RU 2007125687/04 A RU2007125687/04 A RU 2007125687/04A RU 2007125687 A RU2007125687 A RU 2007125687A RU 2007125687 A RU2007125687 A RU 2007125687A
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- Prior art keywords
- formula
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- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 18
- 238000000034 method Methods 0.000 claims 7
- -1 bromo, chloro, methanesulfonyloxy, p-toluenesulfonyloxy Chemical group 0.000 claims 4
- 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 claims 3
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 230000003287 optical effect Effects 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 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 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000000707 stereoselective effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/06—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (11)
1. Способ стереоселективного получения соединения формулы III
где R и R' каждый независимо друг от друга представляет собой С1-С3-алкильную группу; Ar представляет собой дигидробензодиоксинил, бензодиоксинил или фенил, необязательно замещенный до трехкратно заместителями, независимо друг от друга выбранными из галогена, метокси, галогенметила, дигалогенметила и тригалогенметила;
включающий взаимодействие соединения формулы Ia
где R' имеет определенные выше значения
и соединения формулы Ib
с получением соединения формулы II
где R' имеет определенные выше значения,
и дальнейшее взаимодействие соединения формулы II с ариламином Ar-NH2, где Ar имеет определенные выше значения, с получением соединения формулы III.
2. Способ по п.1, где указанный способ осуществляют в виде последовательного процесса без выделения соединения формулы II.
3. Способ по п.1 или 2, где соединение формулы III представляет собой по существу чистый S-энантиомер.
4. Способ получения соединения формулы IV
где Ar и R имеют значения, определенные в п.1,
включающий восстановление соединения формулы III
где R, R' и Ar имеют значения, определенные в п.1.
5. Способ получения соединения формулы V
где Х представляет собой пригодную удаляемую группу, независимо выбранную из группы, включающей бром, хлор, метансульфонилокси, п-толуолсульфонилокси и п-бромфенилсульфонилокси, и Ar и R имеют значения, определенные в п.1,
включающий превращение соединения формулы III
где R, R' и Ar имеют значения, определенные в п.1,
с получением соединения формулы IV
где Ar и R имеют значения, определенные в п.1,
и дальнейшее превращение соединения формулы IV в целевой продукт формулы V.
6. Соединение формулы II
где R и R' каждый независимо друг от друга представляет собой С1-С3-низший алкил, и его оптические изомеры и соли.
7. Соединение по п.6, где указанная соль представляет собой
8. Соединение формулы III
где R и R' каждый независимо друг от друга представляет собой С1-С3-низший алкил, Ar представляет собой дигидробензодиоксинил, бензодиоксинил или фенил, необязательно замещенный до трехкратно заместителями, независимо друг от друга выбранными из галогена, метокси, галогенметила, дигалогенметила и тригалогенметила,
и его оптические изомеры.
9. Соединение по п.8, где Ar представляет собой 2,3-дигидробензодиоксин-5-ил.
10. Соединение формулы IV
где Ar представляет собой дигидробензодиоксинил, или бензодиоксинил, или фенил, необязательно замещенный до трехкратно заместителями, независимо друг от друга выбранными из галогена, метокси, галогенметила, дигалогенметила и тригалогенметила, и его оптические изомеры.
11. Соединение по п.10, где Ar представляет собой 2,3-дигидробензодиоксин-5-ил.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36345802P | 2002-03-12 | 2002-03-12 | |
| US60/363,458 | 2002-03-12 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004130313/04A Division RU2315044C2 (ru) | 2002-03-12 | 2003-03-10 | Способ получения хиральных 1,4-дизамещенных пиперазинов |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2007125687A true RU2007125687A (ru) | 2009-01-20 |
Family
ID=28041772
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004130313/04A RU2315044C2 (ru) | 2002-03-12 | 2003-03-10 | Способ получения хиральных 1,4-дизамещенных пиперазинов |
| RU2007125687/04A RU2007125687A (ru) | 2002-03-12 | 2007-07-06 | Способ получения хиральных 1,4-дизамещенных пиперазинов |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004130313/04A RU2315044C2 (ru) | 2002-03-12 | 2003-03-10 | Способ получения хиральных 1,4-дизамещенных пиперазинов |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US7019137B2 (ru) |
| EP (1) | EP1483256A2 (ru) |
| JP (1) | JP2005527530A (ru) |
| KR (1) | KR20040091119A (ru) |
| CN (2) | CN100451014C (ru) |
| AR (1) | AR038931A1 (ru) |
| AU (1) | AU2003220110B2 (ru) |
| BR (1) | BR0308347A (ru) |
| CA (1) | CA2477906A1 (ru) |
| CR (1) | CR7428A (ru) |
| EC (1) | ECSP045292A (ru) |
| IL (1) | IL163828A0 (ru) |
| MX (1) | MXPA04008730A (ru) |
| NO (1) | NO20043988L (ru) |
| NZ (1) | NZ535169A (ru) |
| RU (2) | RU2315044C2 (ru) |
| TW (1) | TW200304825A (ru) |
| UA (1) | UA79774C2 (ru) |
| WO (1) | WO2003078420A2 (ru) |
| ZA (1) | ZA200408205B (ru) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003007956A1 (en) | 2001-07-20 | 2003-01-30 | Psychogenics, Inc. | Treatment for attention-deficit hyperactivity disorder |
| US7361773B2 (en) * | 2002-03-12 | 2008-04-22 | Wyeth | Preparation of N1-(2'-pyridyl)-1,2-propanediamine sulfamic acid and its use in the synthesis of biologically active piperazines |
| RU2315044C2 (ru) * | 2002-03-12 | 2008-01-20 | Уайт | Способ получения хиральных 1,4-дизамещенных пиперазинов |
| US20050209245A1 (en) * | 2004-03-19 | 2005-09-22 | Wyeth | Process for preparing N-aryl-piperazine derivatives |
| US20050215561A1 (en) * | 2004-03-19 | 2005-09-29 | Krishnendu Ghosh | Pharmaceutical dosage forms and compositions |
| US20070099931A1 (en) * | 2004-03-19 | 2007-05-03 | Wyeth | Pharmaceutical dosage forms and compositions |
| EP2896624B1 (en) | 2007-03-28 | 2016-07-13 | Atir Holding S.A. | Heterotricyclic compounds as serotonergic and/or dopaminergic agents and uses thereof |
| CN108627380B (zh) * | 2017-03-15 | 2020-10-20 | 中国人民解放军军事医学科学院毒物药物研究所 | 去除或减少有毒物质的方法以及检测有毒物质的方法 |
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| DE960203C (de) * | 1953-12-25 | 1957-03-21 | Yoshitomi Pharmaceutical | Verfahren zur Herstellung von N-substituierten Aminocarbonsaeureestern |
| AU577802B2 (en) * | 1983-10-17 | 1988-10-06 | Duphar International Research B.V. | Blood-pressure lowering piperazine derivatives |
| DE3586794T2 (de) | 1984-12-21 | 1993-05-27 | Duphar Int Res | Arzneimittel mit psychotroper wirkung. |
| JPH01125357A (ja) | 1987-11-06 | 1989-05-17 | Dainippon Pharmaceut Co Ltd | トリペプチドの誘導体 |
| AU645681B2 (en) | 1991-05-02 | 1994-01-20 | John Wyeth & Brother Limited | Piperazine derivatives |
| GB9125900D0 (en) * | 1991-12-05 | 1992-02-05 | Wyeth John & Brother Ltd | Piperazine derivatives |
| IL105348A0 (en) * | 1992-04-13 | 1993-08-18 | Fujisawa Pharmaceutical Co | Azabicyclo derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| GB9208740D0 (en) * | 1992-04-23 | 1992-06-10 | Glaxo Group Ltd | Chemical compounds |
| WO1994024115A1 (fr) | 1993-04-16 | 1994-10-27 | Santen Pharmaceutical Co., Ltd. | Nouveau derive de piperazine |
| GB9411099D0 (en) | 1994-06-03 | 1994-07-27 | Wyeth John & Brother Ltd | Piperazine derivatives |
| JPH10504275A (ja) | 1994-06-03 | 1998-04-28 | ジョン・ワイス・アンド・ブラザー・リミテッド | ピペラジン誘導体を製造するための新規な方法および中間体 |
| GB9413772D0 (en) | 1994-07-08 | 1994-08-24 | Wyeth John & Brother Ltd | 5-HT1A ligands |
| CA2196769C (en) * | 1994-08-05 | 2002-10-08 | William S. Faraci | Benzimidazole derivatives having dopaminergic activity |
| US5681958A (en) * | 1995-06-07 | 1997-10-28 | Shaman Pharmaceuticals, Inc. | Cryptolepine analogs with hypoglycemic activity |
| US5889010A (en) * | 1995-05-18 | 1999-03-30 | Pfizer Inc. | Benzimidazole derivatives having dopaminergic activity |
| GB9514901D0 (en) | 1995-07-20 | 1995-09-20 | American Home Prod | Piperazine derivatives |
| WO1997037655A1 (en) | 1996-04-10 | 1997-10-16 | Merck & Co., Inc. | αvβ3 ANTAGONISTS |
| US6271234B1 (en) * | 1997-08-01 | 2001-08-07 | Recordati S.A., Chemical And Pharmaceutical Company | 1,4-disubstituted piperazines |
| JPH11106381A (ja) * | 1997-09-30 | 1999-04-20 | Ss Pharmaceut Co Ltd | クロメン誘導体及びその塩並びにこれを含有する医薬 |
| US6469007B2 (en) | 2000-11-28 | 2002-10-22 | Wyeth | Serotonergic agents |
| US6875772B2 (en) * | 2001-11-30 | 2005-04-05 | Schering Corporation | [1,2,4]-Triazole bicyclic adeonsine A2a receptor antagonists |
| ATE439356T1 (de) * | 2002-03-12 | 2009-08-15 | Wyeth Corp | Verfahren zur herstellung von chiralen n-aryl piperazinen |
| US7091349B2 (en) * | 2002-03-12 | 2006-08-15 | Wyeth | Process for synthesizing N-aryl piperazines with chiral N′-1-[benzoyl(2-pyridyl)amino]-2-propane substitution |
| ES2334836T3 (es) * | 2002-03-12 | 2010-03-16 | Wyeth | Preparacion de 2-((2,3-dihidro-benzo(1,4)dioxin-5-il)-(2-hidroxietil)-amino)-etanol y productos intermedios correspondientes. |
| RU2315044C2 (ru) * | 2002-03-12 | 2008-01-20 | Уайт | Способ получения хиральных 1,4-дизамещенных пиперазинов |
| US7361773B2 (en) * | 2002-03-12 | 2008-04-22 | Wyeth | Preparation of N1-(2'-pyridyl)-1,2-propanediamine sulfamic acid and its use in the synthesis of biologically active piperazines |
-
2003
- 2003-03-10 RU RU2004130313/04A patent/RU2315044C2/ru not_active IP Right Cessation
- 2003-03-10 CA CA002477906A patent/CA2477906A1/en not_active Withdrawn
- 2003-03-10 WO PCT/US2003/007176 patent/WO2003078420A2/en not_active Ceased
- 2003-03-10 BR BR0308347-0A patent/BR0308347A/pt not_active IP Right Cessation
- 2003-03-10 US US10/384,837 patent/US7019137B2/en not_active Expired - Fee Related
- 2003-03-10 NZ NZ535169A patent/NZ535169A/xx unknown
- 2003-03-10 EP EP03716403A patent/EP1483256A2/en not_active Withdrawn
- 2003-03-10 TW TW092105096A patent/TW200304825A/zh unknown
- 2003-03-10 MX MXPA04008730A patent/MXPA04008730A/es active IP Right Grant
- 2003-03-10 CN CNB038059169A patent/CN100451014C/zh not_active Expired - Fee Related
- 2003-03-10 AU AU2003220110A patent/AU2003220110B2/en not_active Expired - Fee Related
- 2003-03-10 JP JP2003576425A patent/JP2005527530A/ja active Pending
- 2003-03-10 CN CNA2008101786904A patent/CN101492383A/zh not_active Withdrawn
- 2003-03-10 IL IL16382803A patent/IL163828A0/xx unknown
- 2003-03-10 KR KR10-2004-7014163A patent/KR20040091119A/ko not_active Ceased
- 2003-03-11 AR ARP030100832A patent/AR038931A1/es unknown
- 2003-10-03 UA UA20041008215A patent/UA79774C2/uk unknown
-
2004
- 2004-08-24 CR CR7428A patent/CR7428A/es not_active Application Discontinuation
- 2004-09-10 EC EC2004005292A patent/ECSP045292A/es unknown
- 2004-09-23 NO NO20043988A patent/NO20043988L/no not_active Application Discontinuation
- 2004-10-11 ZA ZA200408205A patent/ZA200408205B/en unknown
-
2005
- 2005-06-07 US US11/147,055 patent/US7256289B2/en not_active Expired - Fee Related
-
2007
- 2007-07-06 RU RU2007125687/04A patent/RU2007125687A/ru not_active Application Discontinuation
- 2007-08-08 US US11/891,062 patent/US20080058543A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003220110B2 (en) | 2009-04-09 |
| ZA200408205B (en) | 2007-03-28 |
| WO2003078420A3 (en) | 2004-03-11 |
| TW200304825A (en) | 2003-10-16 |
| AU2003220110A1 (en) | 2003-09-29 |
| BR0308347A (pt) | 2005-01-25 |
| RU2004130313A (ru) | 2005-04-10 |
| US7256289B2 (en) | 2007-08-14 |
| MXPA04008730A (es) | 2004-12-06 |
| NO20043988L (no) | 2004-09-23 |
| WO2003078420A2 (en) | 2003-09-25 |
| CN101492383A (zh) | 2009-07-29 |
| RU2315044C2 (ru) | 2008-01-20 |
| UA79774C2 (en) | 2007-07-25 |
| US20030208075A1 (en) | 2003-11-06 |
| CN100451014C (zh) | 2009-01-14 |
| NZ535169A (en) | 2006-03-31 |
| US20080058543A1 (en) | 2008-03-06 |
| US20050228181A1 (en) | 2005-10-13 |
| AR038931A1 (es) | 2005-02-02 |
| IL163828A0 (en) | 2005-12-18 |
| JP2005527530A (ja) | 2005-09-15 |
| CA2477906A1 (en) | 2003-09-25 |
| KR20040091119A (ko) | 2004-10-27 |
| CN1642937A (zh) | 2005-07-20 |
| EP1483256A2 (en) | 2004-12-08 |
| CR7428A (es) | 2008-09-23 |
| ECSP045292A (es) | 2004-10-26 |
| US7019137B2 (en) | 2006-03-28 |
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