TW200523249A - Novel heteroaryl derivative - Google Patents
Novel heteroaryl derivative Download PDFInfo
- Publication number
- TW200523249A TW200523249A TW093121149A TW93121149A TW200523249A TW 200523249 A TW200523249 A TW 200523249A TW 093121149 A TW093121149 A TW 093121149A TW 93121149 A TW93121149 A TW 93121149A TW 200523249 A TW200523249 A TW 200523249A
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- substituted
- heteroaryl
- mmol
- ring
- Prior art date
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- 125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 89
- 150000003839 salts Chemical class 0.000 claims abstract description 59
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 45
- 229940002612 prodrug Drugs 0.000 claims abstract description 39
- 239000000651 prodrug Substances 0.000 claims abstract description 39
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 125000000732 arylene group Chemical group 0.000 claims abstract description 5
- -1 heteroaryl compound Chemical class 0.000 claims description 213
- 150000001875 compounds Chemical class 0.000 claims description 197
- 238000000034 method Methods 0.000 claims description 119
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
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- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000003233 pyrroles Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000002473 indoazoles Chemical group 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 150000003852 triazoles Chemical group 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 230000000979 retarding effect Effects 0.000 claims 2
- JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 150000003937 benzamidines Chemical class 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000001273 butane Substances 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 239000000571 coke Substances 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
- 125000005156 substituted alkylene group Chemical group 0.000 claims 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 abstract description 4
- 125000005549 heteroarylene group Chemical group 0.000 abstract description 2
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- 239000002904 solvent Substances 0.000 description 89
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 84
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 83
- 238000005481 NMR spectroscopy Methods 0.000 description 82
- 239000012044 organic layer Substances 0.000 description 71
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 66
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- 101150041968 CDC13 gene Proteins 0.000 description 62
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
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- 238000003756 stirring Methods 0.000 description 50
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- 235000002639 sodium chloride Nutrition 0.000 description 44
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 238000010898 silica gel chromatography Methods 0.000 description 31
- 239000002585 base Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- 235000019341 magnesium sulphate Nutrition 0.000 description 23
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- 239000007864 aqueous solution Substances 0.000 description 20
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- 125000003277 amino group Chemical group 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
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- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
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- FKXMWPFESIFWMS-UHFFFAOYSA-N (4-methylphenyl)methanone Chemical compound CC1=CC=C([C+]=O)C=C1 FKXMWPFESIFWMS-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
-
- 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrrole Compounds (AREA)
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| JP2003274684 | 2003-07-15 |
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| MX (1) | MXPA06000539A (enExample) |
| TW (1) | TW200523249A (enExample) |
| WO (1) | WO2005012245A1 (enExample) |
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| JPWO2006075638A1 (ja) * | 2005-01-14 | 2008-06-12 | 大日本住友製薬株式会社 | 新規ヘテロアリール誘導体 |
| US20060241073A1 (en) * | 2005-04-20 | 2006-10-26 | Wanders Ronaldus J A | Means and methods for counteracting fatty acid accumulation |
| ATE532770T1 (de) | 2006-09-05 | 2011-11-15 | Kyowa Hakko Kirin Co Ltd | Imidazolderivat |
| WO2008157537A2 (en) * | 2007-06-19 | 2008-12-24 | Ironwood Pharmaceuticals, Inc | Compositions and methods of use for treating or preventing lipid related disorders |
| CN102202662A (zh) * | 2008-10-31 | 2011-09-28 | 大日本住友制药株式会社 | 抗糖尿病剂 |
| JPWO2010110440A1 (ja) | 2009-03-26 | 2012-10-04 | 大日本住友製薬株式会社 | 新規認知機能障害治療剤 |
| TW201105337A (en) * | 2009-07-01 | 2011-02-16 | Dainippon Sumitomo Pharma Co | Medicine derived from a combination of SGLT1-inhibitor and insulin sensitizer |
| CA2787785C (en) | 2010-01-28 | 2018-03-06 | President And Fellows Of Harvard College | Compositions and methods for enhancing proteasome activity |
| WO2012007500A2 (de) | 2010-07-15 | 2012-01-19 | Bayer Cropscience Ag | Neue heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| WO2012154967A1 (en) | 2011-05-12 | 2012-11-15 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
| WO2013138600A1 (en) * | 2012-03-16 | 2013-09-19 | Rosen Eliot M | Radioprotector compounds |
| US9849135B2 (en) | 2013-01-25 | 2017-12-26 | President And Fellows Of Harvard College | USP14 inhibitors for treating or preventing viral infections |
| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
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|---|---|---|---|---|
| DE2752361A1 (de) * | 1977-11-24 | 1979-06-07 | Troponwerke Gmbh & Co Kg | Neue indolderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| WO1998040385A1 (en) * | 1997-03-07 | 1998-09-17 | Novo Nordisk A/S | 4,5,6,7-TETRAHYDRO-THIENO[3,2-c]PYRIDINE DERIVATIVES, THEIR PREPARATION AND USE |
| US6177443B1 (en) | 1997-03-07 | 2001-01-23 | Novo Nordisk A/S | 4,5,6,7-tetrahydro-thieno[3, 2-C]pyridine derivatives, their preparation and use |
| AU2001258784A1 (en) | 2000-05-22 | 2001-12-03 | Takeda Chemical Industries Ltd. | Tyrosine phosphatase inhibitors |
| JP2002121186A (ja) * | 2000-05-22 | 2002-04-23 | Takeda Chem Ind Ltd | チロシンホスファターゼ阻害剤 |
| SK17342002A3 (sk) * | 2000-06-26 | 2004-06-08 | Pfizer Products Inc. | Derivát pyrolo[2,3-d]pyrimidínu ako činidlo potlačujúce imunitu |
| WO2002085851A1 (en) * | 2001-04-19 | 2002-10-31 | Sumitomo Pharmaceuticals Company, Limited | Pyrrole derivative |
| JP2003171275A (ja) | 2001-12-11 | 2003-06-17 | Sumitomo Pharmaceut Co Ltd | ＰＰＡＲδアゴニスト |
| AU2003284479A1 (en) * | 2002-11-28 | 2004-06-18 | Sumitomo Pharmaceuticals Co., Ltd. | Novel heteroaryl derivative |
-
2004
- 2004-07-13 WO PCT/JP2004/010282 patent/WO2005012245A1/ja not_active Ceased
- 2004-07-13 MX MXPA06000539A patent/MXPA06000539A/es active IP Right Grant
- 2004-07-13 ES ES04747746T patent/ES2383895T3/es not_active Expired - Lifetime
- 2004-07-13 AT AT04747746T patent/ATE556051T1/de active
- 2004-07-13 KR KR1020067000907A patent/KR101086654B1/ko not_active Expired - Fee Related
- 2004-07-13 EP EP04747746A patent/EP1647546B1/en not_active Expired - Lifetime
- 2004-07-13 CA CA2531064A patent/CA2531064C/en not_active Expired - Fee Related
- 2004-07-13 CN CNB2004800262352A patent/CN100516041C/zh not_active Expired - Fee Related
- 2004-07-13 US US10/563,361 patent/US7425642B2/en not_active Expired - Fee Related
- 2004-07-13 JP JP2005512472A patent/JP4820169B2/ja not_active Expired - Fee Related
- 2004-07-15 TW TW093121149A patent/TW200523249A/zh not_active IP Right Cessation
-
2008
- 2008-07-15 US US12/173,792 patent/US20080306275A1/en not_active Abandoned
-
2011
- 2011-07-07 JP JP2011151138A patent/JP2011251974A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20060194857A1 (en) | 2006-08-31 |
| JP4820169B2 (ja) | 2011-11-24 |
| EP1647546B1 (en) | 2012-05-02 |
| EP1647546A4 (en) | 2008-07-23 |
| KR20060040681A (ko) | 2006-05-10 |
| CN1849303A (zh) | 2006-10-18 |
| ES2383895T3 (es) | 2012-06-27 |
| CA2531064C (en) | 2012-05-22 |
| JP2011251974A (ja) | 2011-12-15 |
| ATE556051T1 (de) | 2012-05-15 |
| JPWO2005012245A1 (ja) | 2006-09-14 |
| MXPA06000539A (es) | 2006-03-30 |
| US20080306275A1 (en) | 2008-12-11 |
| KR101086654B1 (ko) | 2011-11-24 |
| EP1647546A1 (en) | 2006-04-19 |
| CA2531064A1 (en) | 2005-02-10 |
| WO2005012245A1 (ja) | 2005-02-10 |
| CN100516041C (zh) | 2009-07-22 |
| US7425642B2 (en) | 2008-09-16 |
| HK1087409A1 (en) | 2006-10-13 |
| TWI331142B (enExample) | 2010-10-01 |
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