ATE477227T1 - Verfahren zur herstellung eines trans-4-amino-1- cyclohexancarbonsäurederivats - Google Patents
Verfahren zur herstellung eines trans-4-amino-1- cyclohexancarbonsäurederivatsInfo
- Publication number
- ATE477227T1 ATE477227T1 AT03708516T AT03708516T ATE477227T1 AT E477227 T1 ATE477227 T1 AT E477227T1 AT 03708516 T AT03708516 T AT 03708516T AT 03708516 T AT03708516 T AT 03708516T AT E477227 T1 ATE477227 T1 AT E477227T1
- Authority
- AT
- Austria
- Prior art keywords
- trans
- amino
- producing
- acid derivative
- cyclohexanecarboxylic acid
- Prior art date
Links
Classifications
-
- 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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- 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
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/07—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
- C07C313/06—Sulfinamides
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
-
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/14—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2002067548 | 2002-03-12 | ||
PCT/JP2003/002729 WO2003076374A1 (fr) | 2002-03-12 | 2003-03-07 | Procede de production de derive d'acide trans-4-amino-1-cyclohexanecarboxylique |
Publications (1)
Publication Number | Publication Date |
---|---|
ATE477227T1 true ATE477227T1 (de) | 2010-08-15 |
Family
ID=27800286
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT03708516T ATE477227T1 (de) | 2002-03-12 | 2003-03-07 | Verfahren zur herstellung eines trans-4-amino-1- cyclohexancarbonsäurederivats |
Country Status (14)
Country | Link |
---|---|
US (4) | US7314950B2 (de) |
EP (1) | EP1484301B1 (de) |
JP (1) | JP3850838B2 (de) |
KR (1) | KR100794955B1 (de) |
CN (3) | CN100528821C (de) |
AT (1) | ATE477227T1 (de) |
AU (1) | AU2003213422A1 (de) |
BR (1) | BR0308345A (de) |
CA (1) | CA2478283C (de) |
DE (1) | DE60333733D1 (de) |
ES (1) | ES2350031T3 (de) |
MX (1) | MXPA04008728A (de) |
TW (1) | TWI233924B (de) |
WO (1) | WO2003076374A1 (de) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101898982B (zh) * | 1999-11-26 | 2012-07-04 | 盐野义制药株式会社 | Npy y5拮抗剂 |
JP4636525B2 (ja) * | 2004-03-12 | 2011-02-23 | 塩野義製薬株式会社 | トランス−4−アミノ−1−シクロヘキサンカルボン酸エチルエステルの塩およびその製造方法 |
WO2006001318A1 (ja) * | 2004-06-24 | 2006-01-05 | Shionogi & Co., Ltd. | スルホンアミド化合物 |
US8115030B2 (en) | 2005-03-31 | 2012-02-14 | Shionogi & Co., Ltd. | Process for the preparation of sulfomate-carboxylate derivatives |
JP5187901B2 (ja) * | 2006-08-30 | 2013-04-24 | 塩野義製薬株式会社 | ヒドラジンアミド誘導体 |
WO2008038640A1 (fr) * | 2006-09-28 | 2008-04-03 | Shionogi & Co., Ltd. | Procédé de production d'un sel de l'acide 4-sulfinylamino-1-cyclohexanecarboxylique |
JP5019396B2 (ja) | 2006-10-18 | 2012-09-05 | 塩野義製薬株式会社 | 糖代謝改善剤 |
WO2009038112A1 (ja) | 2007-09-21 | 2009-03-26 | Shionogi & Co., Ltd. | Npyy5受容体拮抗剤を含有する固形製剤 |
CL2009001088A1 (es) | 2008-05-08 | 2011-06-17 | Shionogi & Co | Forma cristalina (ii) de (1r,4r)-4-(1,1-dimetiletilsulfonamido)-n-(5-(trifluorometil) piridin-2-il) ciclohexancarboxamida; procesos de preparacion; utiles como antagonistas del receptor npyy5. |
CN102438623A (zh) * | 2009-03-19 | 2012-05-02 | 盐野义制药株式会社 | 含有npyy5受体拮抗剂的固体制剂 |
JP5604255B2 (ja) * | 2010-10-18 | 2014-10-08 | 住友精化株式会社 | アルキルスルフィニルクロライドの製造方法 |
CN102702005A (zh) * | 2012-06-21 | 2012-10-03 | 扬州天和药业有限公司 | 一种提纯反式氨甲环酸的方法 |
CN105085296B (zh) * | 2015-09-09 | 2017-08-08 | 常州齐晖药业有限公司 | 一种制备反式‑4‑(叔丁氧羰基氨基)环己甲酸中间体异构化的方法 |
WO2017134212A1 (en) | 2016-02-05 | 2017-08-10 | Siegfried Ag | Process for the preparation of trans-4-amino-1-cyclohexanecarboxilic acid and its derivatives |
CN113402428B (zh) * | 2021-06-11 | 2023-03-03 | 重庆医药高等专科学校 | 一种反式4-(叔丁氧羰氨基)环己烷羧酸及其中间体的制备方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4134467A1 (de) | 1991-10-18 | 1993-04-22 | Thomae Gmbh Dr K | Heterobiarylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
US5700801A (en) * | 1994-12-23 | 1997-12-23 | Karl Thomae, Gmbh | Piperazine derivatives, pharmaceutical compositions containing these compounds, their use and processes for preparing them |
CA2229617A1 (en) * | 1995-10-20 | 1997-05-01 | Dr. Karl Thomae Gmbh | 5-membered heterocycles, medicaments containing these compounds, their use and processes for their preparation |
CN101898982B (zh) * | 1999-11-26 | 2012-07-04 | 盐野义制药株式会社 | Npy y5拮抗剂 |
-
2003
- 2003-03-07 DE DE60333733T patent/DE60333733D1/de not_active Expired - Lifetime
- 2003-03-07 US US10/505,963 patent/US7314950B2/en not_active Expired - Fee Related
- 2003-03-07 AT AT03708516T patent/ATE477227T1/de not_active IP Right Cessation
- 2003-03-07 BR BR0308345-4A patent/BR0308345A/pt not_active Application Discontinuation
- 2003-03-07 WO PCT/JP2003/002729 patent/WO2003076374A1/ja active Application Filing
- 2003-03-07 CN CNB038056828A patent/CN100528821C/zh not_active Expired - Fee Related
- 2003-03-07 JP JP2003574597A patent/JP3850838B2/ja not_active Expired - Fee Related
- 2003-03-07 EP EP03708516A patent/EP1484301B1/de not_active Expired - Lifetime
- 2003-03-07 CN CN2007101280230A patent/CN101104598B/zh not_active Expired - Fee Related
- 2003-03-07 MX MXPA04008728A patent/MXPA04008728A/es active IP Right Grant
- 2003-03-07 ES ES03708516T patent/ES2350031T3/es not_active Expired - Lifetime
- 2003-03-07 CA CA2478283A patent/CA2478283C/en not_active Expired - Fee Related
- 2003-03-07 KR KR1020047014226A patent/KR100794955B1/ko not_active IP Right Cessation
- 2003-03-07 CN CN200610059627XA patent/CN1821217B/zh not_active Expired - Fee Related
- 2003-03-07 AU AU2003213422A patent/AU2003213422A1/en not_active Abandoned
- 2003-03-11 TW TW092105199A patent/TWI233924B/zh not_active IP Right Cessation
-
2007
- 2007-10-12 US US11/871,851 patent/US7459580B2/en not_active Expired - Fee Related
-
2008
- 2008-10-07 US US12/247,057 patent/US7547800B2/en not_active Expired - Fee Related
-
2009
- 2009-05-11 US US12/464,031 patent/US7795471B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US20050222255A1 (en) | 2005-10-06 |
CN1639096A (zh) | 2005-07-13 |
EP1484301B1 (de) | 2010-08-11 |
US20090043094A1 (en) | 2009-02-12 |
CN101104598B (zh) | 2011-06-15 |
CA2478283A1 (en) | 2003-09-18 |
CN1821217B (zh) | 2010-09-29 |
TW200305559A (en) | 2003-11-01 |
TWI233924B (en) | 2005-06-11 |
DE60333733D1 (en) | 2010-09-23 |
US7795471B2 (en) | 2010-09-14 |
US7459580B2 (en) | 2008-12-02 |
EP1484301A4 (de) | 2006-09-06 |
KR20040091714A (ko) | 2004-10-28 |
CA2478283C (en) | 2010-10-12 |
CN100528821C (zh) | 2009-08-19 |
MXPA04008728A (es) | 2004-12-06 |
EP1484301A1 (de) | 2004-12-08 |
US7547800B2 (en) | 2009-06-16 |
WO2003076374A1 (fr) | 2003-09-18 |
CN1821217A (zh) | 2006-08-23 |
KR100794955B1 (ko) | 2008-01-15 |
US20080039662A1 (en) | 2008-02-14 |
AU2003213422A1 (en) | 2003-09-22 |
US7314950B2 (en) | 2008-01-01 |
CN101104598A (zh) | 2008-01-16 |
ES2350031T3 (es) | 2011-01-17 |
JP3850838B2 (ja) | 2006-11-29 |
JPWO2003076374A1 (ja) | 2005-07-07 |
BR0308345A (pt) | 2005-01-25 |
US20090221817A1 (en) | 2009-09-03 |
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