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 PDF

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Publication number: JP2004506736A
Authority: JP; Japan
Prior art keywords: alkyl; formula; fluorophenyl; pyridine; pyrazolo
Prior art date: 2000-08-22
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.): Pending

Application number

JP2002521460A

Other languages

English (en)

Japanese (ja)

Other versions

JP2004506736A5 (2

Inventor

アルベルティ，マイケル，ジョン

ボールドウィン，イアン，ロバート

チュン，ムイ

コックリル，ステュアート

フラック，スティーブン

ハリス，フィリップ，アンソニー

ジュン，デーヴィッド，ケンドール

ペッカム，グレゴリー

ピール，マイケル，ロバート

スタンフォード，ジェニファー，バディアング

スティーヴンス，カーク

ヴィール，ジェームズ，マーヴィン

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Glaxo Group Ltd

Original Assignee

Glaxo Group Ltd

Priority date (The priority date 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 date listed.)

2000-08-22

Filing date

2001-08-22

Publication date

2004-03-04

2000-08-22 Priority claimed from GBGB0020556.7A external-priority patent/GB0020556D0/en

2000-08-22 Priority claimed from GB0020576A external-priority patent/GB0020576D0/en

2001-08-22 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2004-03-04 Publication of JP2004506736A publication Critical patent/JP2004506736A/ja

2008-09-25 Publication of JP2004506736A5 publication Critical patent/JP2004506736A5/ja

Status Pending legal-status Critical Current

Links

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
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
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TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 12
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239000002274 desiccant Substances 0.000 description 11
239000002158 endotoxin Substances 0.000 description 11
229920006008 lipopolysaccharide Polymers 0.000 description 11
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
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 10
206010006895 Cachexia Diseases 0.000 description 10
206010028980 Neoplasm Diseases 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
201000011510 cancer Diseases 0.000 description 10
229910002092 carbon dioxide Inorganic materials 0.000 description 10
230000005764 inhibitory process Effects 0.000 description 10
206010039073 rheumatoid arthritis Diseases 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
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239000000126 substance Substances 0.000 description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
125000004432 carbon atom Chemical group C* 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
208000029742 colonic neoplasm Diseases 0.000 description 9
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239000012442 inert solvent Substances 0.000 description 9
229910052763 palladium Inorganic materials 0.000 description 9
MRHCCLIAKMSZSP-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-3-pyrimidin-4-yl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine Chemical compound ClC=1C=C(C=CC1F)C1=NN2C(C=CC(=C2)C(F)(F)F)=C1C1=NC=NC=C1 MRHCCLIAKMSZSP-UHFFFAOYSA-N 0.000 description 8
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235000019341 magnesium sulphate Nutrition 0.000 description 8
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208000024827 Alzheimer disease Diseases 0.000 description 7
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
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206010058467 Lung neoplasm malignant Diseases 0.000 description 7
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
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238000003556 assay Methods 0.000 description 7
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
239000006071 cream Substances 0.000 description 7
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
229910052731 fluorine Inorganic materials 0.000 description 7
OFZKYQYOBLPIPO-UHFFFAOYSA-N guanidine;hydrate Chemical compound O.NC(N)=N OFZKYQYOBLPIPO-UHFFFAOYSA-N 0.000 description 7
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GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000001228 trophic effect Effects 0.000 description 1
229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 description 1
239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
230000003519 ventilatory effect Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
229930195724 β-lactose Natural products 0.000 description 1

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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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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
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Neurology (AREA)
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Diabetes (AREA)
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Rheumatology (AREA)
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Tropical Medicine & Parasitology (AREA)
Communicable Diseases (AREA)
Cardiology (AREA)
Pulmonology (AREA)
Hematology (AREA)
Orthopedic Medicine & Surgery (AREA)
Oncology (AREA)
Dermatology (AREA)
Urology & Nephrology (AREA)
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JP2002521460A 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 Pending JP2004506736A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
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)

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JP2004506736A true JP2004506736A (ja)	2004-03-04
JP2004506736A5 JP2004506736A5 (2)	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

Country Status (19)

Country	Link
US (1)	US7166597B2 (2)
EP (1)	EP1311507B1 (2)
JP (1)	JP2004506736A (2)
KR (1)	KR20030040419A (2)
AR (1)	AR034261A1 (2)
AT (1)	ATE318814T1 (2)
AU (1)	AU2001282318A1 (2)
BR (1)	BR0113448A (2)
CA (1)	CA2420024A1 (2)
DE (1)	DE60117568T2 (2)
ES (1)	ES2259331T3 (2)
HU (1)	HUP0400757A2 (2)
IL (1)	IL154402A0 (2)
MX (1)	MXPA03001593A (2)
NO (1)	NO20030779L (2)
PE (1)	PE20020506A1 (2)
PL (1)	PL362130A1 (2)
UY (1)	UY26899A1 (2)
WO (1)	WO2002016359A1 (2)

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EP1311507A1 (en)	2003-05-21
AR034261A1 (es)	2004-02-18
ES2259331T3 (es)	2006-10-01
CA2420024A1 (en)	2002-02-28
PE20020506A1 (es)	2002-07-09
WO2002016359A1 (en)	2002-02-28
ATE318814T1 (de)	2006-03-15
BR0113448A (pt)	2003-06-17
US7166597B2 (en)	2007-01-23
EP1311507B1 (en)	2006-03-01
DE60117568D1 (de)	2006-04-27
NO20030779L (no)	2003-04-07
DE60117568T2 (de)	2006-08-24
HUP0400757A2 (hu)	2004-07-28
NO20030779D0 (no)	2003-02-19
US20040053942A1 (en)	2004-03-18
PL362130A1 (en)	2004-10-18
KR20030040419A (ko)	2003-05-22
AU2001282318A1 (en)	2002-03-04
UY26899A1 (es)	2002-03-22
MXPA03001593A (es)	2003-06-04
IL154402A0 (en)	2003-09-17

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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

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