CA2479620A1 - Ethane-1,2-diamino-bis[2r)-2-bromo-3-phenylpropanoate], method for production and use thereof - Google Patents
Ethane-1,2-diamino-bis[2r)-2-bromo-3-phenylpropanoate], method for production and use thereof Download PDFInfo
- Publication number
- CA2479620A1 CA2479620A1 CA002479620A CA2479620A CA2479620A1 CA 2479620 A1 CA2479620 A1 CA 2479620A1 CA 002479620 A CA002479620 A CA 002479620A CA 2479620 A CA2479620 A CA 2479620A CA 2479620 A1 CA2479620 A1 CA 2479620A1
- Authority
- CA
- Canada
- Prior art keywords
- bromo
- ethane
- phenylpropanoate
- bis
- phenylpropionic acid
- 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.)
- Abandoned
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 54
- WDRSCFNERFONKU-MRVPVSSYSA-N (2r)-2-bromo-3-phenylpropanoic acid Chemical compound OC(=O)[C@H](Br)CC1=CC=CC=C1 WDRSCFNERFONKU-MRVPVSSYSA-N 0.000 claims abstract description 39
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003112 inhibitor Substances 0.000 claims abstract description 3
- ZRZOZKGGVZNHNM-GGTCEIRZSA-N 2-azaniumylethylazanium;(2r)-2-bromo-3-phenylpropanoate Chemical compound [NH3+]CC[NH3+].[O-]C(=O)[C@H](Br)CC1=CC=CC=C1.[O-]C(=O)[C@H](Br)CC1=CC=CC=C1 ZRZOZKGGVZNHNM-GGTCEIRZSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 15
- -1 R3 is H Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 claims description 6
- UOVSNFYJYANSNI-JTQLQIEISA-N (2s)-2-acetylsulfanyl-3-phenylpropanoic acid Chemical compound CC(=O)S[C@H](C(O)=O)CC1=CC=CC=C1 UOVSNFYJYANSNI-JTQLQIEISA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- UOVSNFYJYANSNI-UHFFFAOYSA-N 2-acetylsulfanyl-3-phenylpropanoic acid Chemical compound CC(=O)SC(C(O)=O)CC1=CC=CC=C1 UOVSNFYJYANSNI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003756 stirring Methods 0.000 description 12
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 10
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 10
- 229930016911 cinnamic acid Natural products 0.000 description 10
- 235000013985 cinnamic acid Nutrition 0.000 description 10
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- ZDQDNFAUFIVJIQ-NIFFTEIASA-N (2r)-2-bromo-3-phenylpropanoate;dicyclohexylazanium Chemical compound [O-]C(=O)[C@H](Br)CC1=CC=CC=C1.C1CCCCC1[NH2+]C1CCCCC1 ZDQDNFAUFIVJIQ-NIFFTEIASA-N 0.000 description 5
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- YKSGKEBVZVHBKC-GGTCEIRZSA-N (2r)-2-bromo-3-phenylpropanoate;2-(dimethylazaniumyl)ethyl-dimethylazanium Chemical compound C[NH+](C)CC[NH+](C)C.[O-]C(=O)[C@H](Br)CC1=CC=CC=C1.[O-]C(=O)[C@H](Br)CC1=CC=CC=C1 YKSGKEBVZVHBKC-GGTCEIRZSA-N 0.000 description 2
- XBLHKXQIWWWZKR-DDWIOCJRSA-N (2r)-2-bromo-3-phenylpropanoate;triethylazanium Chemical compound CC[NH+](CC)CC.[O-]C(=O)[C@H](Br)CC1=CC=CC=C1 XBLHKXQIWWWZKR-DDWIOCJRSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UDEYUIQKWQZFPV-DDWIOCJRSA-N (2r)-2-bromo-3-phenylpropanoic acid;cyclohexanamine Chemical compound NC1CCCCC1.OC(=O)[C@H](Br)CC1=CC=CC=C1 UDEYUIQKWQZFPV-DDWIOCJRSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WDRSCFNERFONKU-UHFFFAOYSA-N 2-bromo-3-phenylpropanoic acid Chemical compound OC(=O)C(Br)CC1=CC=CC=C1 WDRSCFNERFONKU-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241001000171 Chira Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10212198.2 | 2002-03-19 | ||
| DE10212198A DE10212198A1 (de) | 2002-03-19 | 2002-03-19 | Ethan-1-diaminium-bis(2R)-2-brom-3-phenylpropanoat), Verfahren zu dessen Herstellung und dessen Verwendung |
| PCT/EP2003/002353 WO2003078434A1 (de) | 2002-03-19 | 2003-03-07 | Ethan-1,2-diaminium-bis[(2r)-2-brom-3-phenylpropanoat],verfahren zu dessen herstellung und dessen verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2479620A1 true CA2479620A1 (en) | 2003-09-25 |
Family
ID=27797927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002479620A Abandoned CA2479620A1 (en) | 2002-03-19 | 2003-03-07 | Ethane-1,2-diamino-bis[2r)-2-bromo-3-phenylpropanoate], method for production and use thereof |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1487836B1 (enExample) |
| JP (1) | JP4532910B2 (enExample) |
| AT (1) | ATE338756T1 (enExample) |
| AU (1) | AU2003219027A1 (enExample) |
| BR (1) | BR0308485A (enExample) |
| CA (1) | CA2479620A1 (enExample) |
| DE (2) | DE10212198A1 (enExample) |
| IL (1) | IL164042A0 (enExample) |
| MX (1) | MXPA04008490A (enExample) |
| WO (1) | WO2003078434A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5726530B2 (ja) * | 2007-12-05 | 2015-06-03 | クゥアルコム・インコーポレイテッドＱｕａｌｃｏｍｍ Ｉｎｃｏｒｐｏｒａｔｅｄ | 全地球ナビゲーション受信機 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2678759B2 (ja) * | 1988-02-23 | 1997-11-17 | 日本合成化学工業株式会社 | 固体状高分子化合物のアンモニウム塩類の製造法 |
| CA2053340C (en) * | 1990-10-18 | 2002-04-02 | Timothy P. Burkholder | Mercaptoacetylamide derivatives useful as inhibitors of enkephalinase and ace |
| JPH1014590A (ja) * | 1996-06-28 | 1998-01-20 | Kanegafuchi Chem Ind Co Ltd | 光学活性２−置換−３−フェニルプロピオン酸及びそのエステルの製造方法 |
| IT1298267B1 (it) * | 1998-02-18 | 1999-12-20 | Zambon Spa | Procedimento per la preparazione dell'acido (s)-2-acetiltio-3-fenil- propionico e dei suoi sali |
| NL1014353C2 (nl) * | 2000-02-11 | 2001-08-15 | Dsm Nv | Werkwijze voor de bereiding van (R) -2-broom-3-fenylpropaanzuur. |
| NL1014354C2 (nl) * | 2000-02-11 | 2001-08-14 | Dsm Nv | Werkwijze voor de bereiding van (S) -2-acethylthio-3-fenylpropaanzuur. |
-
2002
- 2002-03-19 DE DE10212198A patent/DE10212198A1/de not_active Withdrawn
-
2003
- 2003-03-07 CA CA002479620A patent/CA2479620A1/en not_active Abandoned
- 2003-03-07 IL IL16404203A patent/IL164042A0/xx unknown
- 2003-03-07 AT AT03714788T patent/ATE338756T1/de not_active IP Right Cessation
- 2003-03-07 EP EP03714788A patent/EP1487836B1/de not_active Expired - Lifetime
- 2003-03-07 DE DE50304950T patent/DE50304950D1/de not_active Expired - Lifetime
- 2003-03-07 AU AU2003219027A patent/AU2003219027A1/en not_active Abandoned
- 2003-03-07 BR BR0308485-0A patent/BR0308485A/pt not_active IP Right Cessation
- 2003-03-07 MX MXPA04008490A patent/MXPA04008490A/es unknown
- 2003-03-07 JP JP2003576439A patent/JP4532910B2/ja not_active Expired - Fee Related
- 2003-03-07 WO PCT/EP2003/002353 patent/WO2003078434A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005528358A (ja) | 2005-09-22 |
| DE10212198A1 (de) | 2003-10-02 |
| EP1487836B1 (de) | 2006-09-06 |
| ATE338756T1 (de) | 2006-09-15 |
| IL164042A0 (en) | 2005-12-18 |
| BR0308485A (pt) | 2005-01-18 |
| DE50304950D1 (de) | 2006-10-19 |
| AU2003219027A1 (en) | 2003-09-29 |
| JP4532910B2 (ja) | 2010-08-25 |
| MXPA04008490A (es) | 2004-12-06 |
| EP1487836A1 (de) | 2004-12-22 |
| WO2003078434A1 (de) | 2003-09-25 |
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