ZA200600385B - Triazolopyrimidine derivatives as glycogen synthase kinase 3 inhibitors - Google Patents
Triazolopyrimidine derivatives as glycogen synthase kinase 3 inhibitors Download PDFInfo
- Publication number
- ZA200600385B ZA200600385B ZA200600385A ZA200600385A ZA200600385B ZA 200600385 B ZA200600385 B ZA 200600385B ZA 200600385 A ZA200600385 A ZA 200600385A ZA 200600385 A ZA200600385 A ZA 200600385A ZA 200600385 B ZA200600385 B ZA 200600385B
- Authority
- ZA
- South Africa
- Prior art keywords
- carboxyl
- cyano
- substituted
- hydroxy
- optionally substituted
- Prior art date
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- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 title description 2
- 239000003572 glycogen synthase kinase 3 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 115
- 125000001424 substituent group Chemical group 0.000 claims description 111
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 88
- -1 cyano, carboxyl Chemical group 0.000 claims description 86
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
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- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
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- 125000000532 dioxanyl group Chemical group 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
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- 125000002541 furyl group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 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
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- 125000002346 iodo group Chemical group I* 0.000 description 1
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- 238000002955 isolation Methods 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
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- 125000005963 oxadiazolidinyl group Chemical group 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
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- 231100000614 poison Toxicity 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical group 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
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- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
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- 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
- C07D487/04—Ortho-condensed systems
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P15/16—Masculine contraceptives
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP0350310 | 2003-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200600385B true ZA200600385B (en) | 2007-05-30 |
Family
ID=34112425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200600385A ZA200600385B (en) | 2003-07-16 | 2006-01-13 | Triazolopyrimidine derivatives as glycogen synthase kinase 3 inhibitors |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US7560458B2 (fr) |
| EP (1) | EP1658292B1 (fr) |
| JP (1) | JP2009514782A (fr) |
| KR (1) | KR20060120393A (fr) |
| CN (1) | CN100404536C (fr) |
| AP (1) | AP2006003486A0 (fr) |
| AR (1) | AR045698A1 (fr) |
| AT (1) | ATE370142T1 (fr) |
| AU (1) | AU2004260738B2 (fr) |
| BR (1) | BRPI0412596A (fr) |
| CA (1) | CA2531333A1 (fr) |
| DE (1) | DE602004008303T2 (fr) |
| DK (1) | DK1658292T3 (fr) |
| EA (1) | EA010109B1 (fr) |
| ES (1) | ES2290754T3 (fr) |
| IL (1) | IL173139A (fr) |
| JO (1) | JO2460B1 (fr) |
| MX (1) | MXPA06000540A (fr) |
| NO (1) | NO20060678L (fr) |
| NZ (1) | NZ545058A (fr) |
| PA (1) | PA8607001A1 (fr) |
| PL (1) | PL1658292T3 (fr) |
| PT (1) | PT1658292E (fr) |
| TW (1) | TW200524935A (fr) |
| WO (1) | WO2005012307A1 (fr) |
| ZA (1) | ZA200600385B (fr) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| MXPA05001096A (es) | 2002-07-29 | 2005-11-23 | Rigel Pharmaceuticals Inc | Metodos para tratamiento o prevencion de enfermedades autoinmunes con compuestos de 2,4-diamino-pirimidina. |
| CN100404536C (zh) * | 2003-07-16 | 2008-07-23 | 詹森药业有限公司 | 作为糖原合酶激酶3抑制剂的***并嘧啶衍生物 |
| KR20120062863A (ko) | 2003-07-30 | 2012-06-14 | 리겔 파마슈티칼스, 인크. | 자가면역 질환의 치료 또는 예방에 사용하기 위한 2,4-피리미딘디아민 화합물 |
| CA2533320A1 (fr) * | 2003-08-15 | 2006-02-24 | Novartis Ag | 2, 4-pyrimidine diamines utiles dans le cadre du traitement de maladies neoplasiques, de troubles inflammatoires et de troubles du systeme immunitaire |
| NZ546611A (en) * | 2003-09-18 | 2010-02-26 | Conforma Therapeutics Corp | Novel heterocyclic compounds as HSP90-inhibitors |
| CA2580787A1 (fr) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Derives heterocycliques et utilisation de ceux-ci comme agents therapeutiques |
| CN101083992A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 抑制人硬脂酰CoA去饱和酶的哒嗪衍生物 |
| AR051092A1 (es) | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa |
| TW200626138A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
| EP2269610A3 (fr) | 2004-09-20 | 2011-03-09 | Xenon Pharmaceuticals Inc. | Dérivés hétérocycliques et leur utilisation en tant qu'inhibiteurs de la stearoyl-coa desaturase |
| AU2005286648A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| MX2007003327A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos, y su uso como mediadores de estearoil-coa desaturasa. |
| DE602005023333D1 (de) | 2004-10-15 | 2010-10-14 | Takeda Pharmaceutical | Kinaseinhibitoren |
| MX2007005159A (es) * | 2004-10-29 | 2007-06-26 | Tibotec Pharm Ltd | Derivados de pirimidina biciclicos inhibidores del vih. |
| WO2006076442A2 (fr) * | 2005-01-14 | 2006-07-20 | Janssen Pharmaceutica N.V. | Derives de triazolopyrimidine |
| CA2618646A1 (fr) | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Derives aminothiazole utilises en tant qu'inhibiteurs de la stearoyle-coa desaturase humaine |
| WO2006133426A2 (fr) | 2005-06-08 | 2006-12-14 | Rigel Pharmaceuticals, Inc. | Compositions et procedes d'inhibition de la voie jak |
| US20070203161A1 (en) | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| US7678363B2 (en) | 2005-08-26 | 2010-03-16 | Braincells Inc | Methods of treating psychiatric conditions comprising administration of muscarinic agents in combination with SSRIs |
| EP2258359A3 (fr) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenèse par modulation des récepteurs muscariniques avec sabcomeline |
| US8119655B2 (en) * | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| EP1940389A2 (fr) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation de la neurogenese par inhibition de la pde |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US8962643B2 (en) | 2006-02-24 | 2015-02-24 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the JAK pathway |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP2021000A2 (fr) | 2006-05-09 | 2009-02-11 | Braincells, Inc. | Neurogenèse par modulation de l'angiotensine |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| GEP20135728B (en) | 2006-10-09 | 2013-01-25 | Takeda Pharmaceuticals Co | Kinase inhibitors |
| TWI444379B (zh) | 2007-06-29 | 2014-07-11 | Sunesis Pharmaceuticals Inc | 有用於作為Ｒａｆ激酶抑制劑之化合物 |
| CA2694284A1 (fr) * | 2007-06-29 | 2009-01-08 | Jennifer Cossrow | Composes heterocycliques utiles en tant qu'inhibiteurs de la kinase raf |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| JP5607241B2 (ja) | 2010-05-21 | 2014-10-15 | ケミリア・エービー | 新規ピリミジン誘導体 |
| WO2012127032A1 (fr) | 2011-03-24 | 2012-09-27 | Chemilia Ab | Nouveaux dérivés de pyrimidine |
| CN104066734B (zh) * | 2012-01-28 | 2017-03-29 | 默克专利股份公司 | ***并[4,5‑d]嘧啶衍生物 |
| CA2866450C (fr) | 2012-03-07 | 2020-02-18 | Merck Patent Gmbh | Derives de triazolopyrazine |
| US9617266B2 (en) | 2013-03-05 | 2017-04-11 | Merck Patent Gmbh | Imidazopyrimidine derivatives |
| WO2014135244A1 (fr) * | 2013-03-05 | 2014-09-12 | Merck Patent Gmbh | Dérivés de triazolo[4,5-d]pyrimidine pour le traitement de maladies telles que le cancer |
| CA2911259A1 (fr) | 2013-05-06 | 2014-11-13 | Merck Patent Gmbh | Macrocycles utilises en tant qu'inhibiteurs de kinases |
| EP3226861A2 (fr) * | 2014-12-05 | 2017-10-11 | Centre National de la Recherche Scientifique (CNRS) | Composés pour le traitement de la mucoviscidose |
| WO2017035528A1 (fr) | 2015-08-27 | 2017-03-02 | Nantneuro, Llc | Triazolopyridines et triazolopyrimidines qui abaissent la p-tau induite par le stress |
| US11203576B2 (en) * | 2016-03-11 | 2021-12-21 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Aurora kinase and Janus kinase inhibitors for prevention of graft versus host disease |
| AU2020218366A1 (en) | 2019-02-08 | 2021-09-16 | Frequency Therapeutics, Inc. | Valproic acid compounds and Wnt agonists for treating ear disorders |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5962594A (ja) * | 1982-09-30 | 1984-04-10 | Ss Pharmaceut Co Ltd | ３，５―ジ置換―トリアゾロピリミジン誘導体 |
| US20020040031A1 (en) * | 2000-07-07 | 2002-04-04 | Glasky Michelle S. | Methods for prevention of accumulation of amyloid beta peptide in the central nervous system |
| US6737085B2 (en) * | 2000-11-01 | 2004-05-18 | Tokiwa Phytochemical Co., Ltd. | Apocynum venetum extract for use as antidepressant |
| WO2002050073A1 (fr) * | 2000-12-19 | 2002-06-27 | Smithkline Beecham P.L.C. | Pyrazolo[3,4-c]pyridine en tant qu'inhibiteurs de gsk-3 |
| CN100404536C (zh) * | 2003-07-16 | 2008-07-23 | 詹森药业有限公司 | 作为糖原合酶激酶3抑制剂的***并嘧啶衍生物 |
-
2004
- 2004-07-12 CN CNB2004800201486A patent/CN100404536C/zh not_active Expired - Fee Related
- 2004-07-12 JP JP2006519926A patent/JP2009514782A/ja not_active Withdrawn
- 2004-07-12 WO PCT/EP2004/051455 patent/WO2005012307A1/fr active IP Right Grant
- 2004-07-12 AP AP2006003486A patent/AP2006003486A0/xx unknown
- 2004-07-12 KR KR1020057024541A patent/KR20060120393A/ko not_active Application Discontinuation
- 2004-07-12 AU AU2004260738A patent/AU2004260738B2/en not_active Ceased
- 2004-07-12 AT AT04766189T patent/ATE370142T1/de active
- 2004-07-12 CA CA002531333A patent/CA2531333A1/fr not_active Abandoned
- 2004-07-12 DE DE602004008303T patent/DE602004008303T2/de active Active
- 2004-07-12 US US10/564,844 patent/US7560458B2/en not_active Expired - Fee Related
- 2004-07-12 MX MXPA06000540A patent/MXPA06000540A/es active IP Right Grant
- 2004-07-12 EA EA200600258A patent/EA010109B1/ru not_active IP Right Cessation
- 2004-07-12 BR BRPI0412596-7A patent/BRPI0412596A/pt not_active IP Right Cessation
- 2004-07-12 NZ NZ545058A patent/NZ545058A/en unknown
- 2004-07-12 JO JO200496A patent/JO2460B1/en active
- 2004-07-12 DK DK04766189T patent/DK1658292T3/da active
- 2004-07-12 ES ES04766189T patent/ES2290754T3/es active Active
- 2004-07-12 PL PL04766189T patent/PL1658292T3/pl unknown
- 2004-07-12 EP EP04766189A patent/EP1658292B1/fr active Active
- 2004-07-12 PT PT04766189T patent/PT1658292E/pt unknown
- 2004-07-15 PA PA20048607001A patent/PA8607001A1/es unknown
- 2004-07-15 AR ARP040102496A patent/AR045698A1/es not_active Application Discontinuation
- 2004-07-15 TW TW093121066A patent/TW200524935A/zh unknown
-
2006
- 2006-01-12 IL IL173139A patent/IL173139A/en not_active IP Right Cessation
- 2006-01-13 ZA ZA200600385A patent/ZA200600385B/en unknown
- 2006-02-10 NO NO20060678A patent/NO20060678L/no not_active Application Discontinuation
-
2008
- 2008-09-16 US US12/211,361 patent/US20090036471A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| PT1658292E (pt) | 2007-10-25 |
| PA8607001A1 (es) | 2005-05-10 |
| IL173139A (en) | 2010-04-29 |
| EP1658292B1 (fr) | 2007-08-15 |
| DK1658292T3 (da) | 2007-11-12 |
| AU2004260738A1 (en) | 2005-02-10 |
| EA200600258A1 (ru) | 2006-06-30 |
| EP1658292A1 (fr) | 2006-05-24 |
| DE602004008303T2 (de) | 2008-05-08 |
| AP2006003486A0 (en) | 2006-02-28 |
| CN1823068A (zh) | 2006-08-23 |
| US7560458B2 (en) | 2009-07-14 |
| KR20060120393A (ko) | 2006-11-27 |
| EA010109B1 (ru) | 2008-06-30 |
| NZ545058A (en) | 2008-05-30 |
| AR045698A1 (es) | 2005-11-09 |
| CA2531333A1 (fr) | 2005-02-10 |
| DE602004008303D1 (de) | 2007-09-27 |
| TW200524935A (en) | 2005-08-01 |
| WO2005012307A1 (fr) | 2005-02-10 |
| ATE370142T1 (de) | 2007-09-15 |
| ES2290754T3 (es) | 2008-02-16 |
| US20090036471A1 (en) | 2009-02-05 |
| NO20060678L (no) | 2006-02-10 |
| AU2004260738B2 (en) | 2009-07-16 |
| CN100404536C (zh) | 2008-07-23 |
| MXPA06000540A (es) | 2006-03-30 |
| JO2460B1 (en) | 2009-01-20 |
| BRPI0412596A (pt) | 2006-09-19 |
| IL173139A0 (en) | 2006-06-11 |
| US20060205721A1 (en) | 2006-09-14 |
| PL1658292T3 (pl) | 2008-01-31 |
| JP2009514782A (ja) | 2009-04-09 |
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