JP2010524970A5 - - Google Patents
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- JP2010524970A5 JP2010524970A5 JP2010504274A JP2010504274A JP2010524970A5 JP 2010524970 A5 JP2010524970 A5 JP 2010524970A5 JP 2010504274 A JP2010504274 A JP 2010504274A JP 2010504274 A JP2010504274 A JP 2010504274A JP 2010524970 A5 JP2010524970 A5 JP 2010524970A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- pyrazol
- phenyl
- fluoro
- 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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- -1 benzothiazolonyl Chemical group 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 27
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 4
- MOPYDXKEUIINQL-UHFFFAOYSA-N 1-(3-cyclopentyl-1,2-oxazol-5-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3ON=C(C=3)C3CCCC3)=CC=2)=CC=N1 MOPYDXKEUIINQL-UHFFFAOYSA-N 0.000 claims description 2
- TUGJVLAYGXSREI-UHFFFAOYSA-N 1-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-[3-(1-methylcyclopentyl)-1,2-oxazol-5-yl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3ON=C(C=3)C3(C)CCCC3)=CC=2)=CC=N1 TUGJVLAYGXSREI-UHFFFAOYSA-N 0.000 claims description 2
- 206010027476 Metastases Diseases 0.000 claims description 2
- 230000009401 metastasis Effects 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 25
- 125000000217 alkyl group Chemical group 0.000 claims 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 13
- 239000004202 carbamide Substances 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 12
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 claims 4
- 108091000080 Phosphotransferase Proteins 0.000 claims 4
- 102000004441 bcr-abl Fusion Proteins Human genes 0.000 claims 4
- 108010056708 bcr-abl Fusion Proteins Proteins 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 102000020233 phosphotransferase Human genes 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 2
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims 2
- RZQSHGDKNQMMEF-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3ON=C(C=3)C(C)(C)C)=CC=2)=CC=N1 RZQSHGDKNQMMEF-UHFFFAOYSA-N 0.000 claims 2
- PLMLRBKZJBGMQM-UHFFFAOYSA-N 1-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-(1-propan-2-ylimidazol-4-yl)urea Chemical compound CC(C)N1C=NC(NC(=O)NC=2C(=CC(OC=3C=C(N=CC=3)C3=CN(C)N=C3)=CC=2)F)=C1 PLMLRBKZJBGMQM-UHFFFAOYSA-N 0.000 claims 2
- WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 claims 2
- 206010014950 Eosinophilia Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 102000001253 Protein Kinase Human genes 0.000 claims 2
- 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 claims 2
- 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 2
- 102000037865 fusion proteins Human genes 0.000 claims 2
- 108020001507 fusion proteins Proteins 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 231100000590 oncogenic Toxicity 0.000 claims 2
- 230000002246 oncogenic effect Effects 0.000 claims 2
- 108060006633 protein kinase Proteins 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- OIXYDOADTRFMGN-UHFFFAOYSA-N 1-(1,2-benzoxazol-3-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3C4=CC=CC=C4ON=3)=CC=2)=CC=N1 OIXYDOADTRFMGN-UHFFFAOYSA-N 0.000 claims 1
- WZCXCGYRJFAUJB-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylpyrazol-4-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C(C)(C)C)C(C)=C1NC(=O)NC(C(=C1)F)=CC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 WZCXCGYRJFAUJB-UHFFFAOYSA-N 0.000 claims 1
- VHIIRLFZGKOCAT-UHFFFAOYSA-N 1-(1-tert-butyl-5-oxopyrrolidin-3-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC3CC(=O)N(C3)C(C)(C)C)=CC=2)=CC=N1 VHIIRLFZGKOCAT-UHFFFAOYSA-N 0.000 claims 1
- OKANEFWFFOQCOY-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC3=CN(N=C3)C(C)(C)C)=CC=2)=CC=N1 OKANEFWFFOQCOY-UHFFFAOYSA-N 0.000 claims 1
- AOKJFTJXOUPFCI-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[3-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C(=CC(NC(=O)NC3=CN(N=C3)C(C)(C)C)=CC=2)F)=CC=N1 AOKJFTJXOUPFCI-UHFFFAOYSA-N 0.000 claims 1
- YYWLWSJATUBJHA-UHFFFAOYSA-N 1-(1-tert-butylpyrrol-3-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC3=CN(C=C3)C(C)(C)C)=CC=2)=CC=N1 YYWLWSJATUBJHA-UHFFFAOYSA-N 0.000 claims 1
- UZEJBYLOJSDQJB-UHFFFAOYSA-N 1-(1-tert-butylpyrrolidin-3-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC3CN(CC3)C(C)(C)C)=CC=2)=CC=N1 UZEJBYLOJSDQJB-UHFFFAOYSA-N 0.000 claims 1
- RAXYBCRQJCLRJF-UHFFFAOYSA-N 1-(2-tert-butyl-1,3-oxazol-5-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3OC(=NC=3)C(C)(C)C)=CC=2)=CC=N1 RAXYBCRQJCLRJF-UHFFFAOYSA-N 0.000 claims 1
- MECHJMNKGLQSDE-UHFFFAOYSA-N 1-(2-tert-butyl-4-piperazin-1-ylpyrimidin-5-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3C(=NC(=NC=3)C(C)(C)C)N3CCNCC3)=CC=2)=CC=N1 MECHJMNKGLQSDE-UHFFFAOYSA-N 0.000 claims 1
- ITCUXGLPRALAAJ-UHFFFAOYSA-N 1-(5-cyclopropyl-2-methylpyrazol-3-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3N(N=C(C=3)C3CC3)C)=CC=2)=CC=N1 ITCUXGLPRALAAJ-UHFFFAOYSA-N 0.000 claims 1
- GDMLUYQBRWHUBV-UHFFFAOYSA-N 1-(5-ethylpyridin-3-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound CCC1=CN=CC(NC(=O)NC=2C(=CC(OC=3C=C(N=CC=3)C3=CN(C)N=C3)=CC=2)F)=C1 GDMLUYQBRWHUBV-UHFFFAOYSA-N 0.000 claims 1
- KUAHADRSEWBNCU-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylfuran-3-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C(=CC(OC=3C=C(N=CC=3)C3=CN(C)N=C3)=CC=2)F)=C1C KUAHADRSEWBNCU-UHFFFAOYSA-N 0.000 claims 1
- POVFQPPIWYXHLE-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[2,3-difluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C(=C(F)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C)=CC=2)F)=CC=N1 POVFQPPIWYXHLE-UHFFFAOYSA-N 0.000 claims 1
- MXSREEOVTBWPOB-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[2-fluoro-3-methyl-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=CC(NC(=O)NC=2N(N=C(C=2)C(C)(C)C)C)=C(F)C(C)=C1OC(C=1)=CC=NC=1C=1C=NN(C)C=1 MXSREEOVTBWPOB-UHFFFAOYSA-N 0.000 claims 1
- IMRUJSFGRQOTSM-UHFFFAOYSA-N 1-(6-fluoro-1,3-benzothiazol-2-yl)-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3SC4=CC(F)=CC=C4N=3)=CC=2)=CC=N1 IMRUJSFGRQOTSM-UHFFFAOYSA-N 0.000 claims 1
- HJTHOCNMJVYLOO-UHFFFAOYSA-N 1-[1-tert-butyl-5-(trifluoromethyl)pyrazol-4-yl]-3-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC3=C(N(N=C3)C(C)(C)C)C(F)(F)F)=CC=2)=CC=N1 HJTHOCNMJVYLOO-UHFFFAOYSA-N 0.000 claims 1
- BHEYRAWNMWGPIN-UHFFFAOYSA-N 1-[2-fluoro-3-methyl-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-(3-propan-2-yl-1,2-oxazol-5-yl)urea Chemical compound O1N=C(C(C)C)C=C1NC(=O)NC(C(=C1C)F)=CC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 BHEYRAWNMWGPIN-UHFFFAOYSA-N 0.000 claims 1
- RDPJTBRKUFEHIT-UHFFFAOYSA-N 1-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-(1-propan-2-ylpyrazol-4-yl)urea Chemical compound C1=NN(C(C)C)C=C1NC(=O)NC(C(=C1)F)=CC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 RDPJTBRKUFEHIT-UHFFFAOYSA-N 0.000 claims 1
- OLKFQIHEAGKDJA-UHFFFAOYSA-N 1-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-(2-methyl-5-propan-2-ylpyrazol-3-yl)urea Chemical compound CN1N=C(C(C)C)C=C1NC(=O)NC(C(=C1)F)=CC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 OLKFQIHEAGKDJA-UHFFFAOYSA-N 0.000 claims 1
- QSGWEIPTQPDIHO-UHFFFAOYSA-N 1-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-(5-fluoropyridin-3-yl)urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3C=C(F)C=NC=3)=CC=2)=CC=N1 QSGWEIPTQPDIHO-UHFFFAOYSA-N 0.000 claims 1
- WXSZBMMGPZMAKP-UHFFFAOYSA-N 1-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-(5-methylpyridin-3-yl)urea Chemical compound CC1=CN=CC(NC(=O)NC=2C(=CC(OC=3C=C(N=CC=3)C3=CN(C)N=C3)=CC=2)F)=C1 WXSZBMMGPZMAKP-UHFFFAOYSA-N 0.000 claims 1
- VHQWYXXXWOACMW-UHFFFAOYSA-N 1-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-[2-(1-methylpyrazol-4-yl)-5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3C(=NC=C(C=3)C(F)(F)F)C3=CN(C)N=C3)=CC=2)=CC=N1 VHQWYXXXWOACMW-UHFFFAOYSA-N 0.000 claims 1
- FBEAEYZRUGTMAE-UHFFFAOYSA-N 1-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-[2-oxo-5-(trifluoromethyl)-1h-pyridin-3-yl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3C(NC=C(C=3)C(F)(F)F)=O)=CC=2)=CC=N1 FBEAEYZRUGTMAE-UHFFFAOYSA-N 0.000 claims 1
- YVTOXJOUJNHPPX-UHFFFAOYSA-N 1-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-[3-(trifluoromethyl)-1,2-oxazol-5-yl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3ON=C(C=3)C(F)(F)F)=CC=2)=CC=N1 YVTOXJOUJNHPPX-UHFFFAOYSA-N 0.000 claims 1
- KSEKQUGMORYJTO-UHFFFAOYSA-N 1-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3C=C(C=CC=3)C(F)(F)F)=CC=2)=CC=N1 KSEKQUGMORYJTO-UHFFFAOYSA-N 0.000 claims 1
- MJPXHZIAAFESFT-UHFFFAOYSA-N 1-[2-fluoro-4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=C(F)C(NC(=O)NC=3C=C(C=NC=3)C(F)(F)F)=CC=2)=CC=N1 MJPXHZIAAFESFT-UHFFFAOYSA-N 0.000 claims 1
- FYOHTYMQNCLLLZ-UHFFFAOYSA-N 1-[4-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxyphenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=CC(NC(=O)NC=3C=C(C=NC=3)C(F)(F)F)=CC=2)=CC=N1 FYOHTYMQNCLLLZ-UHFFFAOYSA-N 0.000 claims 1
- IELZFJBBJXHQIN-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)pyridine Chemical compound C1=NN(C)C=C1C1=CC=CC=N1 IELZFJBBJXHQIN-UHFFFAOYSA-N 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 201000004569 Blindness Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 108091008794 FGF receptors Proteins 0.000 claims 1
- 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims 1
- 101100533890 Hypocrea jecorina (strain QM6a) sor3 gene Proteins 0.000 claims 1
- 101100533874 Hypocrea jecorina (strain QM6a) sor5 gene Proteins 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010027406 Mesothelioma Diseases 0.000 claims 1
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 claims 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 1
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 1
- 208000022873 Ocular disease Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010033701 Papillary thyroid cancer Diseases 0.000 claims 1
- 108010051742 Platelet-Derived Growth Factor beta Receptor Proteins 0.000 claims 1
- 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 206010064930 age-related macular degeneration Diseases 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000003310 benzodiazepinyl group Chemical group N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims 1
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000016097 disease of metabolism Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 206010020718 hyperplasia Diseases 0.000 claims 1
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-
2008
- 2008-04-18 CA CA002678639A patent/CA2678639A1/en not_active Abandoned
- 2008-04-18 AU AU2008242767A patent/AU2008242767A1/en not_active Abandoned
- 2008-04-18 US US12/105,350 patent/US20080269254A1/en not_active Abandoned
- 2008-04-18 CA CA002684949A patent/CA2684949A1/en not_active Abandoned
- 2008-04-18 CA CA002684666A patent/CA2684666A1/en not_active Abandoned
- 2008-04-18 MX MX2009011343A patent/MX2009011343A/es not_active Application Discontinuation
- 2008-04-18 BR BRPI0807717-7A2A patent/BRPI0807717A2/pt not_active IP Right Cessation
- 2008-04-18 EP EP08746294A patent/EP2146717A4/en not_active Withdrawn
- 2008-04-18 US US12/105,376 patent/US20080261961A1/en not_active Abandoned
- 2008-04-18 JP JP2010504274A patent/JP2010524970A/ja active Pending
- 2008-04-18 WO PCT/US2008/060867 patent/WO2008131253A1/en not_active Ceased
- 2008-04-18 CA CA002684950A patent/CA2684950A1/en active Pending
- 2008-04-18 BR BRPI0810094-2A2A patent/BRPI0810094A2/pt not_active IP Right Cessation
- 2008-04-18 EP EP08746306A patent/EP2146718A4/en not_active Withdrawn
- 2008-04-18 AU AU2008251723A patent/AU2008251723A1/en not_active Abandoned
- 2008-04-18 SG SG2012053559A patent/SG183054A1/en unknown
- 2008-04-18 WO PCT/US2008/060855 patent/WO2008140895A1/en not_active Ceased
- 2008-04-18 WO PCT/US2008/060896 patent/WO2008131276A1/en not_active Ceased
- 2008-04-18 JP JP2010504293A patent/JP2010524974A/ja active Pending
- 2008-04-18 EP EP12153098A patent/EP2481736A1/en not_active Withdrawn
- 2008-04-18 CN CN2008800085252A patent/CN101878031A/zh active Pending
- 2008-04-18 KR KR1020097017379A patent/KR20100014811A/ko not_active Withdrawn
- 2008-04-18 KR KR1020097024209A patent/KR20100017184A/ko not_active Withdrawn
- 2008-04-18 AU AU2008242697A patent/AU2008242697A1/en not_active Abandoned
- 2008-04-18 EA EA200970700A patent/EA200970700A1/ru unknown
- 2008-04-18 CN CN200880020714A patent/CN101801383A/zh active Pending
- 2008-04-18 MX MX2009009066A patent/MX2009009066A/es not_active Application Discontinuation
- 2008-04-18 RU RU2009142851/15A patent/RU2009142851A/ru not_active Application Discontinuation
- 2008-04-18 US US12/105,302 patent/US20080269267A1/en not_active Abandoned
- 2008-04-18 EP EP08746333A patent/EP2148677A4/en not_active Withdrawn
- 2008-04-18 US US12/105,408 patent/US8143293B2/en not_active Expired - Fee Related
- 2008-04-18 AU AU2008242720A patent/AU2008242720A1/en not_active Abandoned
- 2008-04-18 WO PCT/US2008/060833 patent/WO2008131227A1/en not_active Ceased
- 2008-04-18 EP EP08746279A patent/EP2146716A4/en not_active Withdrawn
-
2009
- 2009-10-20 IL IL201650A patent/IL201650A0/en unknown
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