JP2004506736A - タンパク質キナーゼ阻害剤としての縮合ピラゾール誘導体 - Google Patents
タンパク質キナーゼ阻害剤としての縮合ピラゾール誘導体 Download PDFInfo
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- JP2004506736A JP2004506736A JP2002521460A JP2002521460A JP2004506736A JP 2004506736 A JP2004506736 A JP 2004506736A JP 2002521460 A JP2002521460 A JP 2002521460A JP 2002521460 A JP2002521460 A JP 2002521460A JP 2004506736 A JP2004506736 A JP 2004506736A
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- JP
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- Prior art keywords
- alkyl
- formula
- fluorophenyl
- pyridine
- pyrazolo
- 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.)
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- 239000003909 protein kinase inhibitor Substances 0.000 title abstract description 3
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
- 150000003217 pyrazoles Chemical class 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 61
- 239000012453 solvate Substances 0.000 claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims description 398
- -1 hydroxy, oxo, mercapto Chemical class 0.000 claims description 98
- 125000000217 alkyl group Chemical group 0.000 claims description 88
- 238000000034 method Methods 0.000 claims description 79
- 239000002904 solvent Substances 0.000 claims description 61
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 49
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 41
- 102000002569 MAP Kinase Kinase 4 Human genes 0.000 claims description 39
- 108010068304 MAP Kinase Kinase 4 Proteins 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 230000000694 effects Effects 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 230000001404 mediated effect Effects 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 102000004127 Cytokines Human genes 0.000 claims description 24
- 108090000695 Cytokines Proteins 0.000 claims description 24
- 125000004043 oxo group Chemical group O=* 0.000 claims description 24
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 23
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 208000024891 symptom Diseases 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical group C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 claims description 4
- JIIWFBWSAHKMIA-UHFFFAOYSA-N 3-[[4-[2-(4-fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound OCCCNC1=NC=CC(C2=C3C=CC(=CN3N=C2C=2C=CC(F)=CC=2)C(F)(F)F)=N1 JIIWFBWSAHKMIA-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 abstract description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 174
- 239000000203 mixture Substances 0.000 description 137
- 239000007787 solid Substances 0.000 description 112
- 239000000243 solution Substances 0.000 description 109
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 106
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 85
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 70
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 65
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 61
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 55
- 238000006243 chemical reaction Methods 0.000 description 55
- 235000002639 sodium chloride Nutrition 0.000 description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 150000001412 amines Chemical class 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 235000019439 ethyl acetate Nutrition 0.000 description 37
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 36
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 34
- 238000001914 filtration Methods 0.000 description 32
- 230000002829 reductive effect Effects 0.000 description 30
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 30
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 29
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 28
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 28
- VQUNMLKSMQJXNQ-UHFFFAOYSA-N 2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=NN2C=CC=CC2=C1 VQUNMLKSMQJXNQ-UHFFFAOYSA-N 0.000 description 27
- 210000004027 cell Anatomy 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
- 239000000706 filtrate Substances 0.000 description 25
- APLXBSUOWKLNDE-UHFFFAOYSA-N 3-bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-6-carbonitrile Chemical compound C1=CC(F)=CC=C1C1=NN(C=C(C=C2)C#N)C2=C1Br APLXBSUOWKLNDE-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 239000002244 precipitate Substances 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- 238000010992 reflux Methods 0.000 description 23
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 22
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- 150000002500 ions Chemical class 0.000 description 21
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 229960001340 histamine Drugs 0.000 description 17
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- BUAIGJRXIAKFCN-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-pyridin-4-ylpyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=NN(C=CC=C2)C2=C1C1=CC=NC=C1 BUAIGJRXIAKFCN-UHFFFAOYSA-N 0.000 description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000002431 hydrogen Chemical class 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- WBOGWDUAHFGRPJ-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine Chemical compound C1=C(Cl)C(F)=CC=C1C1=NN2C=C(C(F)(F)F)C=CC2=C1 WBOGWDUAHFGRPJ-UHFFFAOYSA-N 0.000 description 13
- KCSLZTLEXIDXPQ-UHFFFAOYSA-N 2-(3-chlorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine Chemical compound N=1N2C=C(C(F)(F)F)C=CC2=CC=1C1=CC=CC(Cl)=C1 KCSLZTLEXIDXPQ-UHFFFAOYSA-N 0.000 description 13
- JNCSHTULCSUMOM-UHFFFAOYSA-N 6-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NN2C=C(C(F)(F)F)C=CC2=C1 JNCSHTULCSUMOM-UHFFFAOYSA-N 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 13
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 12
- LQMKYGJRFOIGOG-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=NN2C=C(C(F)(F)F)C=CC2=C1 LQMKYGJRFOIGOG-UHFFFAOYSA-N 0.000 description 12
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 11
- BZFGKBQHQJVAHS-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(C(F)(F)F)=C1 BZFGKBQHQJVAHS-UHFFFAOYSA-N 0.000 description 10
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
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- 239000000126 substance Substances 0.000 description 10
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- 125000004432 carbon atom Chemical group C* 0.000 description 9
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 7
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- OFZKYQYOBLPIPO-UHFFFAOYSA-N guanidine;hydrate Chemical compound O.NC(N)=N OFZKYQYOBLPIPO-UHFFFAOYSA-N 0.000 description 7
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- ZHKJHQBOAJQXQR-UHFFFAOYSA-N 1H-azirine Chemical compound N1C=C1 ZHKJHQBOAJQXQR-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- 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
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Landscapes
- Health & Medical Sciences (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| GBGB0020556.7A GB0020556D0 (en) | 2000-08-22 | 2000-08-22 | Fused pyrazole derivatives |
| GB0020576A GB0020576D0 (en) | 2000-08-22 | 2000-08-22 | Fused pyrazole derivatives |
| PCT/GB2001/003783 WO2002016359A1 (en) | 2000-08-22 | 2001-08-22 | Fused pyrazole derivatives being protein kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004506736A true JP2004506736A (ja) | 2004-03-04 |
| JP2004506736A5 JP2004506736A5 (cg-RX-API-DMAC7.html) | 2008-09-25 |
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| JP2002521460A Pending JP2004506736A (ja) | 2000-08-22 | 2001-08-22 | タンパク質キナーゼ阻害剤としての縮合ピラゾール誘導体 |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2011526910A (ja) * | 2008-06-30 | 2011-10-20 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 置換ピリミジン誘導体の製造方法 |
| JP2012502099A (ja) * | 2008-09-11 | 2012-01-26 | ブリストル−マイヤーズ スクイブ カンパニー | Ｃ型肝炎の治療のための化合物 |
| JP2012527461A (ja) * | 2009-05-19 | 2012-11-08 | ダウ アグロサイエンシィズ エルエルシー | 真菌を防除するための化合物および方法 |
| JP2013519696A (ja) * | 2010-02-18 | 2013-05-30 | アルミラル・ソシエダッド・アノニマ | Ｊａｋ阻害剤としてのピラゾール誘導体 |
| JP2013189479A (ja) * | 2006-06-06 | 2013-09-26 | Medicinova Inc | 置換ピラゾロ［１，５−ａ］ピリジン化合物およびその使用方法 |
| JP2014528961A (ja) * | 2011-10-06 | 2014-10-30 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | ヘテロシクリルピリ（ミ）ジニルピラゾール |
| JP2016505529A (ja) * | 2012-11-19 | 2016-02-25 | アイアールエム・リミテッド・ライアビリティ・カンパニーＩｒｍ，Ｌｌｃ | 寄生虫病の処置のための化合物および組成物 |
| JP2016539977A (ja) * | 2013-12-09 | 2016-12-22 | ユーシービー バイオファルマ エスピーアールエル | Ｔｎｆ活性のモジュレーターとしてのピラゾロピリジン誘導体 |
| JP2017500362A (ja) * | 2013-12-26 | 2017-01-05 | イグナイタ インコーポレイテッド | ピラゾロ［１，５−ａ］ピリジン誘導体およびその使用方法 |
| JP2019517517A (ja) * | 2016-06-02 | 2019-06-24 | セルジーン コーポレイション | 動物及びヒトの抗マラリア薬 |
| JP2019517500A (ja) * | 2016-06-02 | 2019-06-24 | セルジーン コーポレイション | 動物及びヒトの抗トリパノソーマならびに抗リーシュマニア薬 |
Families Citing this family (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| ES2245380T3 (es) | 2000-12-15 | 2006-01-01 | Glaxo Group Limited | Pirazolopiridinas. |
| DE60112330T2 (de) | 2000-12-15 | 2006-04-13 | Glaxo Group Ltd., Greenford | Pyrazolopyridinderivate |
| US7153855B2 (en) | 2001-03-08 | 2006-12-26 | Smithkline Beecham Corporation | Pyrazolopyridinyl pyrimidine therapeutic compounds |
| US7034030B2 (en) | 2001-03-30 | 2006-04-25 | Smithkline Beecham Corporation | Pyralopyridines, process for their preparation and use as therapeutic compounds |
| GB0108770D0 (en) | 2001-04-06 | 2001-05-30 | Eisai London Res Lab Ltd | Inhibitors |
| ATE332301T1 (de) | 2001-04-10 | 2006-07-15 | Smithkline Beecham Corp | Antivirale pyrazolopyridin verbindungen |
| US6962914B2 (en) | 2001-04-27 | 2005-11-08 | Smithkline Beecham Corporation | Pyrazolopyridinyl pyridine and pyrimidine therapeutic compounds |
| SK287857B6 (sk) | 2001-05-24 | 2012-01-04 | Eli Lilly And Company | Novel pyrrole derivatives as pharmaceutical agents |
| DE60214179T2 (de) | 2001-06-21 | 2007-01-04 | Smithkline Beecham Corp. | Imidazo-1,2-A/Pyriden-Derivate zur Prophylaxe und Behandlung von Herpes-Infektionen |
| JPWO2003020313A1 (ja) * | 2001-09-04 | 2004-12-16 | 小野薬品工業株式会社 | スフィンゴシン−１−リン酸受容体調節剤からなる呼吸器疾患治療剤 |
| ES2262893T3 (es) | 2001-10-05 | 2006-12-01 | Smithkline Beecham Corporation | Derivados de imidazo-piridina para su uso en el tratamiento de infeccion virica por herpes. |
| GB0124936D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124933D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124941D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124939D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124938D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124934D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124931D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124932D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
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- 2001-08-22 JP JP2002521460A patent/JP2004506736A/ja active Pending
- 2001-08-22 EP EP01960928A patent/EP1311507B1/en not_active Expired - Lifetime
- 2001-08-22 KR KR10-2003-7002634A patent/KR20030040419A/ko not_active Withdrawn
- 2001-08-22 DE DE60117568T patent/DE60117568T2/de not_active Expired - Fee Related
- 2001-08-22 PL PL36213001A patent/PL362130A1/xx not_active Application Discontinuation
- 2001-08-22 WO PCT/GB2001/003783 patent/WO2002016359A1/en not_active Ceased
- 2001-08-22 MX MXPA03001593A patent/MXPA03001593A/es unknown
- 2001-08-22 CA CA002420024A patent/CA2420024A1/en not_active Abandoned
- 2001-08-22 AU AU2001282318A patent/AU2001282318A1/en not_active Abandoned
- 2001-08-22 AT AT01960928T patent/ATE318814T1/de not_active IP Right Cessation
- 2001-08-22 HU HU0400757A patent/HUP0400757A2/hu unknown
- 2001-08-22 IL IL15440201A patent/IL154402A0/xx unknown
- 2001-08-22 BR BR0113448-5A patent/BR0113448A/pt not_active Application Discontinuation
- 2001-08-22 US US10/362,146 patent/US7166597B2/en not_active Expired - Fee Related
- 2001-08-22 UY UY26899A patent/UY26899A1/es unknown
- 2001-08-22 AR ARP010104007A patent/AR034261A1/es unknown
- 2001-08-22 ES ES01960928T patent/ES2259331T3/es not_active Expired - Lifetime
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013189479A (ja) * | 2006-06-06 | 2013-09-26 | Medicinova Inc | 置換ピラゾロ［１，５−ａ］ピリジン化合物およびその使用方法 |
| JP2011526910A (ja) * | 2008-06-30 | 2011-10-20 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 置換ピリミジン誘導体の製造方法 |
| JP2012502099A (ja) * | 2008-09-11 | 2012-01-26 | ブリストル−マイヤーズ スクイブ カンパニー | Ｃ型肝炎の治療のための化合物 |
| JP2012527461A (ja) * | 2009-05-19 | 2012-11-08 | ダウ アグロサイエンシィズ エルエルシー | 真菌を防除するための化合物および方法 |
| JP2013519696A (ja) * | 2010-02-18 | 2013-05-30 | アルミラル・ソシエダッド・アノニマ | Ｊａｋ阻害剤としてのピラゾール誘導体 |
| JP2014528961A (ja) * | 2011-10-06 | 2014-10-30 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | ヘテロシクリルピリ（ミ）ジニルピラゾール |
| JP2016505529A (ja) * | 2012-11-19 | 2016-02-25 | アイアールエム・リミテッド・ライアビリティ・カンパニーＩｒｍ，Ｌｌｃ | 寄生虫病の処置のための化合物および組成物 |
| JP2016539977A (ja) * | 2013-12-09 | 2016-12-22 | ユーシービー バイオファルマ エスピーアールエル | Ｔｎｆ活性のモジュレーターとしてのピラゾロピリジン誘導体 |
| JP2017500362A (ja) * | 2013-12-26 | 2017-01-05 | イグナイタ インコーポレイテッド | ピラゾロ［１，５−ａ］ピリジン誘導体およびその使用方法 |
| JP2019517517A (ja) * | 2016-06-02 | 2019-06-24 | セルジーン コーポレイション | 動物及びヒトの抗マラリア薬 |
| JP2019517500A (ja) * | 2016-06-02 | 2019-06-24 | セルジーン コーポレイション | 動物及びヒトの抗トリパノソーマならびに抗リーシュマニア薬 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20040053942A1 (en) | 2004-03-18 |
| WO2002016359A1 (en) | 2002-02-28 |
| ES2259331T3 (es) | 2006-10-01 |
| HUP0400757A2 (hu) | 2004-07-28 |
| EP1311507B1 (en) | 2006-03-01 |
| IL154402A0 (en) | 2003-09-17 |
| BR0113448A (pt) | 2003-06-17 |
| PE20020506A1 (es) | 2002-07-09 |
| NO20030779D0 (no) | 2003-02-19 |
| NO20030779L (no) | 2003-04-07 |
| EP1311507A1 (en) | 2003-05-21 |
| CA2420024A1 (en) | 2002-02-28 |
| AR034261A1 (es) | 2004-02-18 |
| AU2001282318A1 (en) | 2002-03-04 |
| UY26899A1 (es) | 2002-03-22 |
| ATE318814T1 (de) | 2006-03-15 |
| MXPA03001593A (es) | 2003-06-04 |
| US7166597B2 (en) | 2007-01-23 |
| DE60117568T2 (de) | 2006-08-24 |
| PL362130A1 (en) | 2004-10-18 |
| KR20030040419A (ko) | 2003-05-22 |
| DE60117568D1 (de) | 2006-04-27 |
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