WO2001038292A3 - Verfahren zur herstellung optisch aktiver amine - Google Patents
Verfahren zur herstellung optisch aktiver amine Download PDFInfo
- Publication number
- WO2001038292A3 WO2001038292A3 PCT/EP2000/011191 EP0011191W WO0138292A3 WO 2001038292 A3 WO2001038292 A3 WO 2001038292A3 EP 0011191 W EP0011191 W EP 0011191W WO 0138292 A3 WO0138292 A3 WO 0138292A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- optically active
- active amines
- amines
- producing optically
- relates
- 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.)
- Ceased
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
- C07C217/10—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the 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
- C07C235/04—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 being acyclic and saturated
- C07C235/08—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 being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE50009670T DE50009670D1 (de) | 1999-11-25 | 2000-11-13 | Verfahren zur herstellung optisch aktiver amine |
| US10/129,978 US7078226B1 (en) | 1999-11-25 | 2000-11-13 | Method for producing optically active amines |
| DK00987237T DK1232279T3 (da) | 2000-11-13 | 2000-11-13 | Fremgangsmåde til fremstilling af optisk aktive aminer |
| JP2001539849A JP4776846B2 (ja) | 1999-11-25 | 2000-11-13 | 光学活性アミンの製造方法 |
| UA2002065187A UA77651C2 (en) | 1999-11-25 | 2000-11-13 | Method for producing optically active amines and optically active amide |
| BRPI0015805-4A BR0015805B1 (pt) | 1999-11-25 | 2000-11-13 | processo para preparar compostos opticamente ativos, e, composto opticamente ativo. |
| AU23561/01A AU2356101A (en) | 1999-11-25 | 2000-11-13 | Method for producing optically active amines |
| EEP200200268A EE05162B1 (et) | 1999-11-25 | 2000-11-13 | Meetod optiliselt aktiivsete amiinide saamiseks |
| AT00987237T ATE290099T1 (de) | 1999-11-25 | 2000-11-13 | Verfahren zur herstellung optisch aktiver amine |
| IL14904800A IL149048A0 (en) | 1999-11-25 | 2000-11-13 | Method for producing optically active amines |
| CA2396661A CA2396661C (en) | 1999-11-25 | 2000-11-13 | Method for producing optically active amines |
| EP00987237A EP1232279B1 (de) | 1999-11-25 | 2000-11-13 | Verfahren zur herstellung optisch aktiver amine |
| IL149048A IL149048A (en) | 1999-11-25 | 2002-04-09 | Method for producing optically active amines |
| NO20022458A NO328104B1 (no) | 1999-11-25 | 2002-05-24 | Fremgangsmate for fremstilling av optisk aktive aminer |
| US11/327,307 US7358396B2 (en) | 1999-11-25 | 2006-01-09 | Preparation of optically active amines |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19956786A DE19956786A1 (de) | 1999-11-25 | 1999-11-25 | Verfahren zur Herstellung optisch aktiver Amine |
| DE19956786.7 | 1999-11-25 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/327,307 Division US7358396B2 (en) | 1999-11-25 | 2006-01-09 | Preparation of optically active amines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2001038292A2 WO2001038292A2 (de) | 2001-05-31 |
| WO2001038292A3 true WO2001038292A3 (de) | 2002-02-28 |
Family
ID=7930317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2000/011191 Ceased WO2001038292A2 (de) | 1999-11-25 | 2000-11-13 | Verfahren zur herstellung optisch aktiver amine |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US7078226B1 (de) |
| EP (1) | EP1232279B1 (de) |
| JP (1) | JP4776846B2 (de) |
| KR (1) | KR100677798B1 (de) |
| CN (1) | CN1204262C (de) |
| AT (1) | ATE290099T1 (de) |
| AU (1) | AU2356101A (de) |
| BR (1) | BR0015805B1 (de) |
| CA (1) | CA2396661C (de) |
| DE (2) | DE19956786A1 (de) |
| EE (1) | EE05162B1 (de) |
| IL (2) | IL149048A0 (de) |
| NO (1) | NO328104B1 (de) |
| RU (1) | RU2293724C9 (de) |
| UA (1) | UA77651C2 (de) |
| WO (1) | WO2001038292A2 (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2843112B1 (fr) * | 2002-07-30 | 2004-10-22 | Clariant | Procede de preparation d'amines primaires. |
| GB0306267D0 (en) * | 2003-03-19 | 2003-04-23 | Ineos Fluor Ltd | Process |
| KR100739537B1 (ko) | 2004-01-07 | 2007-07-13 | 주식회사 카이로라이트 | 카이랄 무기-유기 혼성 다공성 물질 및 이의 제조 방법 |
| DE102005028492A1 (de) * | 2005-06-20 | 2006-12-28 | Basf Ag | Verfahren zur Herstellung von optisch aktiven Aminoalkylphenolen |
| DE102005063192A1 (de) * | 2005-12-30 | 2007-07-05 | Basf Ag | Racematspaltung von 2,6-trans-Dimethyl-morpholin |
| JP2010512333A (ja) * | 2006-12-07 | 2010-04-22 | ヘルシン ヘルスケア ソシエテ アノニム | 塩酸パロノセトロンの結晶及び非晶質形 |
| EP2387556B1 (de) * | 2009-01-16 | 2014-07-30 | Basf Se | Trennung eines enantiomerengemischs von (r)- und (s)-3-amino-1-butanol |
| BR112017001516B1 (pt) | 2015-02-17 | 2023-10-31 | Amorepacific Corporation | Método de ressolubilização quiral, estereoisômero, método para preparar um composto, composto, composição, e kit de ressolubilização quiral |
| KR102565407B1 (ko) * | 2016-01-04 | 2023-08-10 | (주)아모레퍼시픽 | 극성 비양자성 용매를 이용한 n-[4-(1-아미노에틸)-페닐]-술폰아미드 유도체의 카이랄 분할 방법 |
| CN117945937B (zh) * | 2024-01-26 | 2024-07-30 | 重庆华森制药股份有限公司 | 一种制备高光学纯度苯磺酸美洛加巴林的方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE247144C (de) * | ||||
| DE723498C (de) * | 1939-01-19 | 1942-08-18 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von aliphatischen Oxyaldehyden und Oxyketonen |
| WO1996023894A1 (de) * | 1995-02-03 | 1996-08-08 | Basf Aktiengesellschaft | Racematspaltung primärer und sekundärer heteroatomsubstituierter amine durch enzym-katalysierte acylierung |
| WO1997028271A1 (de) * | 1996-02-01 | 1997-08-07 | Bayer Aktiengesellschaft | Verfahren zur herstellung von optisch aktiven aminen |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB292615A (de) * | 1927-06-23 | 1929-07-18 | I.G. Farbenindustrie Aktiengesellschaft | |
| DE551436C (de) * | 1930-08-22 | 1932-06-02 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von Diaminen |
| US2424061A (en) * | 1944-06-29 | 1947-07-15 | Lilly Co Eli | 9-amino-alkyl-amino-substituted acridine derivatives |
| GB609488A (en) * | 1944-08-07 | 1948-10-01 | Lilly Co Eli | Production of propyldiamines and acridine compounds of propyldiamines |
| GB615715A (en) * | 1945-02-22 | 1949-01-11 | Sharples Chemicals Inc | Improvements in or relating to amines and process of forming same |
| US2624753A (en) * | 1948-06-30 | 1953-01-06 | Monsanto Chemicals | 5-n-butoxy-1-hexyl adipate and method for making the same |
| US2764615A (en) * | 1952-05-01 | 1956-09-25 | Purdue Research Foundation | Alkoxyalkylamines and acid addition salts |
| GB739741A (en) * | 1952-11-10 | 1955-11-02 | Lilly Co Eli | Improvements in or relating to substituted benzamidopropylamines and process of preparing the same |
| US3009915A (en) * | 1958-10-01 | 1961-11-21 | Sahyun | 1, 4, 5, 6-tetrahydro-pirimidylmethylacetates and glycolates |
| BE795019A (fr) * | 1972-02-07 | 1973-08-06 | Ciba Geigy | Composes anthraquinoniques, leur procede de preparation et leur utilisation |
| DE2509155A1 (de) * | 1975-03-03 | 1976-09-09 | Hoechst Ag | 1,4-benzoxazinderivate und verfahren zu ihrer herstellung |
| IT1083904B (it) * | 1976-08-31 | 1985-05-25 | Lilly Co Eli | Composizione erbicida acquatica a base di fenossi alchilammine sostituite |
| US4207343A (en) * | 1978-06-22 | 1980-06-10 | Eli Lilly And Company | 1-Phenyl-3-(substituted phenoxy)propylamines |
| DE2935062A1 (de) * | 1978-09-06 | 1980-03-20 | Degussa | Substituierte aminoalkylguanidine, deren herstellung und arzneimittel |
| FR2496653A1 (fr) * | 1980-12-22 | 1982-06-25 | Delalande Sa | Nouveaux derives aminoalcoyl heterocycliques, leurs procedes de preparation et leur application en therapeutique |
| HU184392B (en) * | 1981-03-04 | 1984-08-28 | Gyogyszerkutato Intezet | Process for producing new alkylene-diamine derivatives |
| DE3277694D1 (en) * | 1982-06-23 | 1987-12-23 | Teikoku Hormone Mfg Co Ltd | Hydrazinopyridazine compound, process for production thereof, and use thereof as medicament |
| JPS61145166A (ja) * | 1984-12-12 | 1986-07-02 | バイエル・アクチエンゲゼルシヤフト | 新規な2,4‐ジアミノピリジン類 |
| JPS61171458A (ja) * | 1985-01-25 | 1986-08-02 | Tokuyama Soda Co Ltd | アミン化合物の製造方法 |
| JPS61197558A (ja) * | 1985-02-25 | 1986-09-01 | Nippon Chemiphar Co Ltd | 新規なキナルジン酸アミド誘導体およびその製造法 |
| JPS6354342A (ja) * | 1986-08-26 | 1988-03-08 | Daicel Chem Ind Ltd | (±)−α−エチルベンジルアミンの光学分割方法 |
| PT87163B (pt) * | 1987-04-09 | 1992-07-31 | Lilly Co Eli | Processo para a preparacao de 1-fenil-3-naftaleniloxi-propanaminas |
| US5039706A (en) * | 1987-11-30 | 1991-08-13 | Du Pont Merck Pharmaceutical Company | Antiinflammatory PLA2 inhibitors |
| FI902321A7 (fi) * | 1989-05-19 | 1990-11-20 | Eisai Co Ltd | Buteenihappojohdannaiset |
| JPH07119189B2 (ja) * | 1989-09-28 | 1995-12-20 | 北陸製薬株式会社 | 光学活性なベンジルアルコール誘導体及びその用途 |
| WO1991019002A1 (en) | 1990-06-01 | 1991-12-12 | Carlbiotech Ltd. A/S | A process for chiral enrichment of asymmetric primary amines |
| US5057607A (en) | 1990-06-08 | 1991-10-15 | Eli Lilly And Company | Enantiomerically selective biocatalyzed acylation |
| DE4232424A1 (de) * | 1992-09-28 | 1994-03-31 | Basf Ag | Verfahren zur Herstellung von ungesättigten Aminen |
| DE4332738A1 (de) | 1993-09-25 | 1995-03-30 | Basf Ag | Racematspaltung primärer und sekundärer Amine durch Enzym-katalysierte Acylierung |
| JP3312459B2 (ja) * | 1993-12-28 | 2002-08-05 | 東レ株式会社 | 光学活性アミンの単離方法 |
| DE19534208A1 (de) | 1995-09-15 | 1997-03-20 | Basf Ag | Spaltung von optisch aktiven Amiden |
| DE19535762A1 (de) * | 1995-09-26 | 1997-03-27 | Basf Ag | Verfahren zur Racematspaltung |
| US6387692B1 (en) | 1995-12-06 | 2002-05-14 | Bayer Aktiengesellschaft | Process for the preparation of optically active amines |
| US6166048A (en) * | 1999-04-20 | 2000-12-26 | Targacept, Inc. | Pharmaceutical compositions for inhibition of cytokine production and secretion |
| DE19621686A1 (de) | 1996-05-30 | 1997-12-04 | Bayer Ag | Verfahren zur Herstellung von optisch aktiven Aminen |
| DE19629692A1 (de) | 1996-07-23 | 1998-01-29 | Bayer Ag | Verfahren zur Herstellung von racemischen Phenethylaminen |
| DE19727517A1 (de) * | 1997-06-30 | 1999-01-07 | Basf Ag | Racematspaltung von Aminosäureestern durch Enzym-katalysierte Acylierung |
| EP1027333A4 (de) * | 1997-09-30 | 2000-11-08 | Merck & Co Inc | Thrombin-inhibitoren |
| HUP9702411A2 (hu) * | 1997-12-11 | 2000-03-28 | Gyógyszerkutató Intézet Kft. | Fenoxi-alkil-amin-származékok és a vegyületeket tartalmazó antiaritmiás hatású gyógyszerkészítmények |
| DE19837745A1 (de) * | 1998-08-20 | 2000-02-24 | Basf Ag | Enzymkatalysierte Racematspaltung von primären Aminen |
| MXPA01012202A (es) * | 1999-05-24 | 2002-06-21 | Targacept Inc | Composiciones farmaceuticas y metodos de uso. |
| WO2001000626A1 (en) * | 1999-06-30 | 2001-01-04 | The Regents Of The University Of California | Hexahydropyrrolo[1,2-c]pyrimidines as antiviral, antifungal and/or antitumor agents |
-
1999
- 1999-11-25 DE DE19956786A patent/DE19956786A1/de not_active Withdrawn
-
2000
- 2000-11-13 US US10/129,978 patent/US7078226B1/en not_active Expired - Lifetime
- 2000-11-13 BR BRPI0015805-4A patent/BR0015805B1/pt not_active IP Right Cessation
- 2000-11-13 CN CNB008161372A patent/CN1204262C/zh not_active Expired - Fee Related
- 2000-11-13 KR KR1020027006527A patent/KR100677798B1/ko not_active Expired - Fee Related
- 2000-11-13 EP EP00987237A patent/EP1232279B1/de not_active Expired - Lifetime
- 2000-11-13 RU RU2002117053/04A patent/RU2293724C9/ru not_active IP Right Cessation
- 2000-11-13 UA UA2002065187A patent/UA77651C2/uk unknown
- 2000-11-13 JP JP2001539849A patent/JP4776846B2/ja not_active Expired - Fee Related
- 2000-11-13 IL IL14904800A patent/IL149048A0/xx active IP Right Grant
- 2000-11-13 DE DE50009670T patent/DE50009670D1/de not_active Expired - Lifetime
- 2000-11-13 AT AT00987237T patent/ATE290099T1/de active
- 2000-11-13 AU AU23561/01A patent/AU2356101A/en not_active Abandoned
- 2000-11-13 WO PCT/EP2000/011191 patent/WO2001038292A2/de not_active Ceased
- 2000-11-13 EE EEP200200268A patent/EE05162B1/xx unknown
- 2000-11-13 CA CA2396661A patent/CA2396661C/en not_active Expired - Lifetime
-
2002
- 2002-04-09 IL IL149048A patent/IL149048A/en unknown
- 2002-05-24 NO NO20022458A patent/NO328104B1/no not_active IP Right Cessation
-
2006
- 2006-01-09 US US11/327,307 patent/US7358396B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE247144C (de) * | ||||
| DE723498C (de) * | 1939-01-19 | 1942-08-18 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von aliphatischen Oxyaldehyden und Oxyketonen |
| WO1996023894A1 (de) * | 1995-02-03 | 1996-08-08 | Basf Aktiengesellschaft | Racematspaltung primärer und sekundärer heteroatomsubstituierter amine durch enzym-katalysierte acylierung |
| WO1997028271A1 (de) * | 1996-02-01 | 1997-08-07 | Bayer Aktiengesellschaft | Verfahren zur herstellung von optisch aktiven aminen |
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| ANDRES C ET AL: "STEREOSELECTIVE RING OPENING OF CHIRAL OXAZOLIDINES BY REFORMATSKY REAGENTS: AN ENANTIOSELECTIVE ENTRY TO BETA-AMINO ESTERS", TETRAHEDRON LETTERS,NL,ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, vol. 33, no. 20, 12 May 1992 (1992-05-12), pages 2895 - 2898, XP002043792, ISSN: 0040-4039 * |
| BESSE P ET AL: "Stereoselective chemoenzymatic synthesis of both enantiomers of protected 4-amino-2-pentanone", TETRAHEDRON: ASYMMETRY,NL,ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, vol. 10, no. 11, 4 June 1999 (1999-06-04), pages 2213 - 2224, XP004174104, ISSN: 0957-4166 * |
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| DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOEDERUNG DER CHEMISCHEN WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; XP002171097 * |
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Also Published As
| Publication number | Publication date |
|---|---|
| AU2356101A (en) | 2001-06-04 |
| NO20022458L (no) | 2002-05-24 |
| CA2396661A1 (en) | 2001-05-31 |
| US20060122429A1 (en) | 2006-06-08 |
| IL149048A0 (en) | 2002-11-10 |
| US7078226B1 (en) | 2006-07-18 |
| ATE290099T1 (de) | 2005-03-15 |
| IL149048A (en) | 2007-03-08 |
| RU2293724C2 (ru) | 2007-02-20 |
| KR20020051937A (ko) | 2002-06-29 |
| RU2002117053A (ru) | 2004-01-20 |
| EE05162B1 (et) | 2009-04-15 |
| JP2003514888A (ja) | 2003-04-22 |
| UA77651C2 (en) | 2007-01-15 |
| NO20022458D0 (no) | 2002-05-24 |
| EP1232279B1 (de) | 2005-03-02 |
| CA2396661C (en) | 2010-10-19 |
| CN1204262C (zh) | 2005-06-01 |
| EE200200268A (et) | 2003-06-16 |
| WO2001038292A2 (de) | 2001-05-31 |
| NO328104B1 (no) | 2009-12-07 |
| CN1399687A (zh) | 2003-02-26 |
| US7358396B2 (en) | 2008-04-15 |
| DE50009670D1 (de) | 2005-04-07 |
| EP1232279A2 (de) | 2002-08-21 |
| KR100677798B1 (ko) | 2007-02-05 |
| BR0015805A (pt) | 2002-08-06 |
| RU2293724C9 (ru) | 2008-06-27 |
| BR0015805B1 (pt) | 2013-04-30 |
| DE19956786A1 (de) | 2001-05-31 |
| JP4776846B2 (ja) | 2011-09-21 |
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