ZA200401316B - Amino-phthalazinone derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions containing them. - Google Patents
Amino-phthalazinone derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions containing them. Download PDFInfo
- Publication number
- ZA200401316B ZA200401316B ZA200401316A ZA200401316A ZA200401316B ZA 200401316 B ZA200401316 B ZA 200401316B ZA 200401316 A ZA200401316 A ZA 200401316A ZA 200401316 A ZA200401316 A ZA 200401316A ZA 200401316 B ZA200401316 B ZA 200401316B
- Authority
- ZA
- South Africa
- Prior art keywords
- phthalazin
- dihydro
- oxo
- benzyl
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 50
- IUBSMBJKUKVEMK-UHFFFAOYSA-N 4-amino-2h-phthalazin-1-one Chemical class C1=CC=C2C(N)=NNC(=O)C2=C1 IUBSMBJKUKVEMK-UHFFFAOYSA-N 0.000 title claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229940043355 kinase inhibitor Drugs 0.000 title description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 148
- 125000000217 alkyl group Chemical group 0.000 claims description 142
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 69
- 125000000623 heterocyclic group Chemical group 0.000 claims description 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
- -1 nitro, carboxy Chemical group 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 34
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- 102000001253 Protein Kinase Human genes 0.000 claims description 22
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- 229910052736 halogen Inorganic materials 0.000 claims description 9
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- AYJQCFPUYBRGAG-UHFFFAOYSA-N 1-[1-[(3-fluorophenyl)methyl]-4-oxo-3h-phthalazin-6-yl]-3-pyridin-3-ylurea Chemical compound FC1=CC=CC(CC=2C3=CC=C(NC(=O)NC=4C=NC=CC=4)C=C3C(=O)NN=2)=C1 AYJQCFPUYBRGAG-UHFFFAOYSA-N 0.000 claims description 2
- PUVFSOHSSORMMM-UHFFFAOYSA-N 7-amino-4-(pyridin-3-ylmethyl)-2h-phthalazin-1-one Chemical compound N=1NC(=O)C2=CC(N)=CC=C2C=1CC1=CC=CN=C1 PUVFSOHSSORMMM-UHFFFAOYSA-N 0.000 claims description 2
- OIKKRYMMIGIJEN-UHFFFAOYSA-N 7-amino-4-(quinolin-3-ylmethyl)-2h-phthalazin-1-one Chemical compound C1=CC=CC2=CC(CC=3C4=CC=C(C=C4C(=O)NN=3)N)=CN=C21 OIKKRYMMIGIJEN-UHFFFAOYSA-N 0.000 claims description 2
- UJZAZZGWFKYPIT-UHFFFAOYSA-N 7-amino-4-[(3-fluorophenyl)methyl]-2h-phthalazin-1-one Chemical compound N=1NC(=O)C2=CC(N)=CC=C2C=1CC1=CC=CC(F)=C1 UJZAZZGWFKYPIT-UHFFFAOYSA-N 0.000 claims description 2
- SPXHQKBEMODERJ-UHFFFAOYSA-N 7-amino-4-[(4-chloro-3-fluorophenyl)methyl]-2h-phthalazin-1-one Chemical compound N=1NC(=O)C2=CC(N)=CC=C2C=1CC1=CC=C(Cl)C(F)=C1 SPXHQKBEMODERJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
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- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 claims description 2
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- OAOPDYUHWPBJCW-UHFFFAOYSA-N cyanoboron;sodium Chemical compound [Na].[B]C#N OAOPDYUHWPBJCW-UHFFFAOYSA-N 0.000 claims description 2
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- KXUMNSRAVZFKGY-UHFFFAOYSA-N ethyl 4-oxo-4-[[4-oxo-1-(pyridin-3-ylmethyl)-3h-phthalazin-6-yl]amino]butanoate Chemical compound N=1NC(=O)C2=CC(NC(=O)CCC(=O)OCC)=CC=C2C=1CC1=CC=CN=C1 KXUMNSRAVZFKGY-UHFFFAOYSA-N 0.000 claims description 2
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- SJJIKHBVIVCEBE-UHFFFAOYSA-N n-[4-oxo-1-(quinolin-3-ylmethyl)-3h-phthalazin-6-yl]-2-propylpentanamide Chemical compound C1=CC=CC2=CC(CC=3C4=CC=C(C=C4C(=O)NN=3)NC(=O)C(CCC)CCC)=CN=C21 SJJIKHBVIVCEBE-UHFFFAOYSA-N 0.000 description 1
- RDOQTNZNXCLJHH-UHFFFAOYSA-N n-[4-oxo-1-(quinolin-3-ylmethyl)-3h-phthalazin-6-yl]furan-2-carboxamide Chemical compound C=1C=C2C(CC=3C=C4C=CC=CC4=NC=3)=NNC(=O)C2=CC=1NC(=O)C1=CC=CO1 RDOQTNZNXCLJHH-UHFFFAOYSA-N 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- GZLPQVREIBIVAT-UHFFFAOYSA-N n-phenylphthalazin-1-amine Chemical class N=1N=CC2=CC=CC=C2C=1NC1=CC=CC=C1 GZLPQVREIBIVAT-UHFFFAOYSA-N 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- YSZIOXAEADAJLX-UHFFFAOYSA-N phthalazine-1,4-dione Chemical group C1=CC=C2C(=O)N=NC(=O)C2=C1 YSZIOXAEADAJLX-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 238000007086 side reaction Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 102000009076 src-Family Kinases Human genes 0.000 description 1
- 108010087686 src-Family Kinases Proteins 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
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- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
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- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
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- A61K31/50—Pyridazines; Hydrogenated pyridazines
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- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
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- C07D237/30—Phthalazines
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- 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
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- 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
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- 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
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- 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
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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Landscapes
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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- Oncology (AREA)
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- Structural Engineering (AREA)
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- Hematology (AREA)
- Rheumatology (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/922,729 US20030073692A1 (en) | 2001-08-07 | 2001-08-07 | Amino-phthalazinone derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200401316B true ZA200401316B (en) | 2005-03-10 |
Family
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Family Applications (1)
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| ZA200401316A ZA200401316B (en) | 2001-08-07 | 2004-02-18 | Amino-phthalazinone derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions containing them. |
Country Status (23)
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| US (2) | US20030073692A1 (xx) |
| EP (1) | EP1427708B1 (xx) |
| JP (1) | JP2005501085A (xx) |
| KR (1) | KR20040029400A (xx) |
| CN (2) | CN101085759A (xx) |
| AT (1) | ATE407928T1 (xx) |
| BR (1) | BR0211807A (xx) |
| CA (1) | CA2455759A1 (xx) |
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| CZ (1) | CZ2004305A3 (xx) |
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| IL (1) | IL159843A0 (xx) |
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| NO (1) | NO20040547L (xx) |
| NZ (1) | NZ531310A (xx) |
| PL (1) | PL368440A1 (xx) |
| PT (1) | PT1427708E (xx) |
| SI (1) | SI1427708T1 (xx) |
| WO (1) | WO2003014090A1 (xx) |
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Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7151102B2 (en) * | 2000-10-30 | 2006-12-19 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| GB0305681D0 (en) | 2003-03-12 | 2003-04-16 | Kudos Pharm Ltd | Phthalazinone derivatives |
| GB0317466D0 (en) | 2003-07-25 | 2003-08-27 | Univ Sheffield | Use |
| US7598383B2 (en) * | 2003-11-19 | 2009-10-06 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| DK1684736T3 (da) | 2003-12-01 | 2011-11-21 | Kudos Pharm Ltd | Inhibitorer af DNA-skadereparation til behandling af cancer |
| EP1694686A1 (en) * | 2003-12-19 | 2006-08-30 | Takeda San Diego, Inc. | Kinase inhibitors |
| EP1763524A1 (en) * | 2004-04-23 | 2007-03-21 | Takeda San Diego, Inc. | Indole derivatives and use thereof as kinase inhibitors |
| JP2008510734A (ja) * | 2004-08-18 | 2008-04-10 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
| GB0419072D0 (en) * | 2004-08-26 | 2004-09-29 | Kudos Pharm Ltd | Phthalazinone derivatives |
| AU2005289560A1 (en) * | 2004-09-28 | 2006-04-06 | Angion Biomedica Corp. | Small molecule modulators of cytokine activity |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| BE567431A (xx) * | 1957-05-07 | |||
| EP0600831A1 (de) | 1992-11-27 | 1994-06-08 | Ciba-Geigy Ag | Phthalazinonderivate |
| EP0634404A1 (en) * | 1993-07-13 | 1995-01-18 | Rhone Poulenc Agriculture Ltd. | Phtalazin derivatives and their use as pesticides |
| JPH0961961A (ja) * | 1995-08-21 | 1997-03-07 | Fuji Photo Film Co Ltd | 熱現像感光材料 |
| CO4950519A1 (es) | 1997-02-13 | 2000-09-01 | Novartis Ag | Ftalazinas, preparaciones farmaceuticas que las comprenden y proceso para su preparacion |
| EP0875512A3 (en) | 1997-04-16 | 1999-04-07 | Fabrica Espanola De Productos Quimicos Y Farmaceuticos, S.A. (Faes) | New naphthylpiperazine derivatives with antipsychotic activity |
| EP1180514A4 (en) * | 1999-04-09 | 2003-02-26 | Meiji Seika Kaisha | NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS AND BENAMID DERIVATIVES, AND THEIR MEDICINAL PRODUCTS |
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2001
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2002
- 2002-07-30 EA EA200400283A patent/EA006645B1/ru not_active IP Right Cessation
- 2002-07-30 SI SI200230738T patent/SI1427708T1/sl unknown
- 2002-07-30 PL PL02368440A patent/PL368440A1/xx not_active Application Discontinuation
- 2002-07-30 ES ES02758416T patent/ES2315385T3/es not_active Expired - Lifetime
- 2002-07-30 US US10/486,463 patent/US7432263B2/en not_active Expired - Fee Related
- 2002-07-30 NZ NZ531310A patent/NZ531310A/en unknown
- 2002-07-30 MX MXPA04000905A patent/MXPA04000905A/es unknown
- 2002-07-30 CA CA002455759A patent/CA2455759A1/en not_active Abandoned
- 2002-07-30 EP EP02758416A patent/EP1427708B1/en not_active Expired - Lifetime
- 2002-07-30 WO PCT/EP2002/008544 patent/WO2003014090A1/en active IP Right Grant
- 2002-07-30 DE DE60228857T patent/DE60228857D1/de not_active Expired - Fee Related
- 2002-07-30 CZ CZ2004305A patent/CZ2004305A3/cs unknown
- 2002-07-30 AT AT02758416T patent/ATE407928T1/de not_active IP Right Cessation
- 2002-07-30 PT PT02758416T patent/PT1427708E/pt unknown
- 2002-07-30 IL IL15984302A patent/IL159843A0/xx unknown
- 2002-07-30 BR BR0211807-6A patent/BR0211807A/pt not_active IP Right Cessation
- 2002-07-30 CN CNA2007101101264A patent/CN101085759A/zh active Pending
- 2002-07-30 JP JP2003519040A patent/JP2005501085A/ja not_active Abandoned
- 2002-07-30 KR KR10-2004-7001814A patent/KR20040029400A/ko not_active Application Discontinuation
- 2002-07-30 DK DK02758416T patent/DK1427708T3/da active
- 2002-07-30 CN CNA028154193A patent/CN1538960A/zh active Pending
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2004
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- 2004-02-18 ZA ZA200401316A patent/ZA200401316B/en unknown
- 2004-03-03 CO CO04019499A patent/CO5560573A2/es not_active Application Discontinuation
Also Published As
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|---|---|
| CN101085759A (zh) | 2007-12-12 |
| IL159843A0 (en) | 2004-06-20 |
| CA2455759A1 (en) | 2003-02-20 |
| BR0211807A (pt) | 2004-09-21 |
| NO20040547L (no) | 2004-03-03 |
| ATE407928T1 (de) | 2008-09-15 |
| WO2003014090A1 (en) | 2003-02-20 |
| SI1427708T1 (sl) | 2008-12-31 |
| KR20040029400A (ko) | 2004-04-06 |
| US7432263B2 (en) | 2008-10-07 |
| EP1427708B1 (en) | 2008-09-10 |
| CZ2004305A3 (cs) | 2004-08-18 |
| CO5560573A2 (es) | 2005-09-30 |
| CN1538960A (zh) | 2004-10-20 |
| EA200400283A1 (ru) | 2004-08-26 |
| JP2005501085A (ja) | 2005-01-13 |
| EP1427708A1 (en) | 2004-06-16 |
| MXPA04000905A (es) | 2004-04-02 |
| PL368440A1 (en) | 2005-03-21 |
| PT1427708E (pt) | 2008-11-20 |
| DE60228857D1 (de) | 2008-10-23 |
| US20050020583A1 (en) | 2005-01-27 |
| US20030073692A1 (en) | 2003-04-17 |
| ES2315385T3 (es) | 2009-04-01 |
| NZ531310A (en) | 2006-02-24 |
| EA006645B1 (ru) | 2006-02-24 |
| DK1427708T3 (da) | 2008-11-24 |
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