JP2012511563A5 - - Google Patents
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- JP2012511563A5 JP2012511563A5 JP2011540218A JP2011540218A JP2012511563A5 JP 2012511563 A5 JP2012511563 A5 JP 2012511563A5 JP 2011540218 A JP2011540218 A JP 2011540218A JP 2011540218 A JP2011540218 A JP 2011540218A JP 2012511563 A5 JP2012511563 A5 JP 2012511563A5
- Authority
- JP
- Japan
- Prior art keywords
- ureido
- tolyl
- butyl
- tert
- pyrazol
- 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.)
- Pending
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- -1 4- (4- (3- (3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl) ureido) naphthalen-1-yloxy) pyridin-2-yl Chemical group 0.000 claims 37
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
- 239000004202 carbamide Substances 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 230000000155 isotopic effect Effects 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- XZYOKLDOGCKXFU-AREMUKBSSA-N (3r)-n-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-3-(dimethylamino)pyrrolidine-1-carboxamide Chemical compound C1[C@H](N(C)C)CCN1C(=O)NC1=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=CC=N1 XZYOKLDOGCKXFU-AREMUKBSSA-N 0.000 claims 1
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 1
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- RHPOFSSHQSUXCH-UHFFFAOYSA-N 1-(2-methoxyethyl)-3-pyridin-2-ylurea Chemical compound COCCNC(=O)NC1=CC=CC=N1 RHPOFSSHQSUXCH-UHFFFAOYSA-N 0.000 claims 1
- JDSCOPALPVVAMI-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(carbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(N)=O)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 JDSCOPALPVVAMI-UHFFFAOYSA-N 0.000 claims 1
- YTTNMTQRALUGRX-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(carbamoylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC(N)=O)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 YTTNMTQRALUGRX-UHFFFAOYSA-N 0.000 claims 1
- BVFKRRNCUURTOI-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(cyclopropylcarbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)NC4CC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 BVFKRRNCUURTOI-UHFFFAOYSA-N 0.000 claims 1
- DXLIDCWBUAERSC-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(cyclopropylcarbamoylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC(=O)NC4CC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 DXLIDCWBUAERSC-UHFFFAOYSA-N 0.000 claims 1
- HOWYJHYHNQTBNF-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(methylcarbamoylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound CNC(=O)NC1=NC=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=N1 HOWYJHYHNQTBNF-UHFFFAOYSA-N 0.000 claims 1
- XLHTULSCPXKFHD-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(phenylcarbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)NC=4C=CC=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 XLHTULSCPXKFHD-UHFFFAOYSA-N 0.000 claims 1
- WUXMHKROVSEUIG-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(piperidin-4-ylcarbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)NC4CCNCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 WUXMHKROVSEUIG-UHFFFAOYSA-N 0.000 claims 1
- HQCCANAXHHBLJQ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-[(1-methylsulfonylpiperidin-4-yl)carbamoylamino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)NC4CCN(CC4)S(C)(=O)=O)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 HQCCANAXHHBLJQ-UHFFFAOYSA-N 0.000 claims 1
- GKLBOQXVLALWMH-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-[(2-morpholin-4-yl-2-oxoethyl)carbamoylamino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)NCC(=O)N4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 GKLBOQXVLALWMH-UHFFFAOYSA-N 0.000 claims 1
- MDOLZJKXHAXTEF-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-[(2-oxo-2-pyrrolidin-1-ylethyl)carbamoylamino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)NCC(=O)N4CCCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 MDOLZJKXHAXTEF-UHFFFAOYSA-N 0.000 claims 1
- DAJMQZIBLSBHAE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-[[2-(4-methylpiperazin-1-yl)-2-oxoethyl]carbamoylamino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1CN(C)CCN1C(=O)CNC(=O)NC1=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=CC=N1 DAJMQZIBLSBHAE-UHFFFAOYSA-N 0.000 claims 1
- XQQKILZJJJNJBN-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[6-(carbamoylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=CN=C(NC(N)=O)C=3)=CC=2)=CC(C(C)(C)C)=N1 XQQKILZJJJNJBN-UHFFFAOYSA-N 0.000 claims 1
- RHSMFYIHIIADSH-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-naphthalen-1-ylurea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C=CC=2)=CC(C(C)(C)C)=N1 RHSMFYIHIIADSH-UHFFFAOYSA-N 0.000 claims 1
- DPNYEFODFDMYDL-UHFFFAOYSA-N 1-benzyl-3-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)NCC=4C=CC=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 DPNYEFODFDMYDL-UHFFFAOYSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- SGHDEYQIMDEDSS-UHFFFAOYSA-N 2-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]carbamoylamino]-n-methylacetamide Chemical compound C1=NC(NC(=O)NCC(=O)NC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 SGHDEYQIMDEDSS-UHFFFAOYSA-N 0.000 claims 1
- HGYVVJZWXGWXPT-UHFFFAOYSA-N 2-methoxy-n-[4-[4-[[2-(4-methylphenyl)-5-propan-2-ylpyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 HGYVVJZWXGWXPT-UHFFFAOYSA-N 0.000 claims 1
- OKEWJDJWTSMGKA-UHFFFAOYSA-N 3-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-1,1-dimethylurea Chemical compound C1=NC(NC(=O)N(C)C)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 OKEWJDJWTSMGKA-UHFFFAOYSA-N 0.000 claims 1
- SZVBINLROMAAJO-UHFFFAOYSA-N 3-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=NC=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=N1 SZVBINLROMAAJO-UHFFFAOYSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 206010012434 Dermatitis allergic Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 125000003047 N-acetyl group Chemical group 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 208000029771 childhood onset asthma Diseases 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- DMUQGBCYZATOMY-UHFFFAOYSA-N n-[2-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-oxoethyl]-3-morpholin-4-ylpropanamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)CNC(=O)CCN4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 DMUQGBCYZATOMY-UHFFFAOYSA-N 0.000 claims 1
- CRTSPNMFWCENOV-UHFFFAOYSA-N n-[2-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-oxoethyl]morpholine-4-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)CNC(=O)N4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 CRTSPNMFWCENOV-UHFFFAOYSA-N 0.000 claims 1
- UPBBOCRQZZBDGZ-UHFFFAOYSA-N n-[2-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-oxoethyl]oxane-4-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)CNC(=O)C4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 UPBBOCRQZZBDGZ-UHFFFAOYSA-N 0.000 claims 1
- QBTIJQJNAFHVLA-UHFFFAOYSA-N n-[2-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-oxoethyl]pyridine-4-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)CNC(=O)C=4C=CN=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 QBTIJQJNAFHVLA-UHFFFAOYSA-N 0.000 claims 1
- QGSYDPHSISRRKJ-UHFFFAOYSA-N n-[4-[4-[[5-(1-hydroxy-2-methylpropan-2-yl)-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)CO)C=3C=CC(C)=CC=3)=CC=2)=C1 QGSYDPHSISRRKJ-UHFFFAOYSA-N 0.000 claims 1
- SEXCAXGEWGCFFE-UHFFFAOYSA-N n-[4-[4-[[5-ethyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C=1C=C(C)C=CC=1N1N=C(CC)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC1=CC=NC(NC(=O)COC)=C1 SEXCAXGEWGCFFE-UHFFFAOYSA-N 0.000 claims 1
- AVUUHIYJPTWYNX-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 AVUUHIYJPTWYNX-UHFFFAOYSA-N 0.000 claims 1
- OFVXXPNLFUKQTB-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-4-methylpiperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=CC=N1 OFVXXPNLFUKQTB-UHFFFAOYSA-N 0.000 claims 1
- PFGPXCHWPKIYPY-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]morpholine-4-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)N4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 PFGPXCHWPKIYPY-UHFFFAOYSA-N 0.000 claims 1
- HPVNUUMLMRFDNP-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]oxane-4-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)C4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 HPVNUUMLMRFDNP-UHFFFAOYSA-N 0.000 claims 1
- INZJHXPSKMNVOB-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]piperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)N4CCCCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 INZJHXPSKMNVOB-UHFFFAOYSA-N 0.000 claims 1
- JOPZSFGHCVMVBH-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]pyrrolidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)N4CCCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 JOPZSFGHCVMVBH-UHFFFAOYSA-N 0.000 claims 1
- NXEJIGOGROPCLK-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]-2-methoxyacetamide Chemical compound COCC(=O)NC1=NC=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=N1 NXEJIGOGROPCLK-UHFFFAOYSA-N 0.000 claims 1
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- 2009-12-11 EP EP09771766.4A patent/EP2370429B1/en active Active
- 2009-12-11 KR KR1020117015760A patent/KR20110094130A/ko not_active Ceased
- 2009-12-11 BR BRPI0922962A patent/BRPI0922962A2/pt not_active IP Right Cessation
- 2009-12-11 CN CN200980156810.3A patent/CN102333770B/zh not_active Expired - Fee Related
- 2009-12-11 AU AU2009326148A patent/AU2009326148B2/en not_active Ceased
- 2009-12-11 AU AU2009326149A patent/AU2009326149B2/en not_active Ceased
- 2009-12-11 JP JP2011540218A patent/JP2012511563A/ja active Pending
- 2009-12-11 EP EP09768546.5A patent/EP2370428B1/en active Active
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2014
- 2014-09-16 JP JP2014187591A patent/JP5959587B2/ja active Active
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