JP2014528403A5 - - Google Patents
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- Publication number
- JP2014528403A5 JP2014528403A5 JP2014532481A JP2014532481A JP2014528403A5 JP 2014528403 A5 JP2014528403 A5 JP 2014528403A5 JP 2014532481 A JP2014532481 A JP 2014532481A JP 2014532481 A JP2014532481 A JP 2014532481A JP 2014528403 A5 JP2014528403 A5 JP 2014528403A5
- Authority
- JP
- Japan
- Prior art keywords
- butyl
- pyrazol
- urea
- tert
- naphthalen
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 16
- -1 3- (tert-butyl) -1- (p-tolyl) -1H-pyrazol-5-yl Chemical group 0.000 claims 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 6
- 206010006458 Bronchitis chronic Diseases 0.000 claims 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 5
- 201000003883 Cystic fibrosis Diseases 0.000 claims 5
- 206010014561 Emphysema Diseases 0.000 claims 5
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 5
- 208000006673 asthma Diseases 0.000 claims 5
- 206010006451 bronchitis Diseases 0.000 claims 5
- 208000029771 childhood onset asthma Diseases 0.000 claims 5
- 208000007451 chronic bronchitis Diseases 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 230000002265 prevention Effects 0.000 claims 5
- 201000000306 sarcoidosis Diseases 0.000 claims 5
- 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 4
- 206010006187 Breast cancer Diseases 0.000 claims 4
- 208000026310 Breast neoplasm Diseases 0.000 claims 4
- 206010006895 Cachexia Diseases 0.000 claims 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims 4
- 206010009944 Colon cancer Diseases 0.000 claims 4
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 4
- 206010010741 Conjunctivitis Diseases 0.000 claims 4
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 4
- 206010012434 Dermatitis allergic Diseases 0.000 claims 4
- 206010012442 Dermatitis contact Diseases 0.000 claims 4
- 206010027476 Metastases Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 206010033645 Pancreatitis Diseases 0.000 claims 4
- 201000004681 Psoriasis Diseases 0.000 claims 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims 4
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 4
- 201000010105 allergic rhinitis Diseases 0.000 claims 4
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 4
- 201000008937 atopic dermatitis Diseases 0.000 claims 4
- 208000010668 atopic eczema Diseases 0.000 claims 4
- 239000004202 carbamide Substances 0.000 claims 4
- 208000010247 contact dermatitis Diseases 0.000 claims 4
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims 4
- 206010017758 gastric cancer Diseases 0.000 claims 4
- 201000001441 melanoma Diseases 0.000 claims 4
- 230000009401 metastasis Effects 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 206010039083 rhinitis Diseases 0.000 claims 4
- 201000009890 sinusitis Diseases 0.000 claims 4
- 201000011549 stomach cancer Diseases 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 230000005764 inhibitory process Effects 0.000 claims 3
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 3
- 201000008482 osteoarthritis Diseases 0.000 claims 3
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 3
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 2
- 208000017667 Chronic Disease Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 206010062106 Respiratory tract infection viral Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 210000001503 joint Anatomy 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 238000002054 transplantation Methods 0.000 claims 2
- 230000004614 tumor growth Effects 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- UBHCCGHQPDLGDY-UHFFFAOYSA-N 1-[4-(2-anilinopyrimidin-4-yl)oxynaphthalen-1-yl]-3-[5-tert-butyl-2-(4-hydroxyphenyl)pyrazol-3-yl]urea Chemical compound C=1C=C(O)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC(N=1)=CC=NC=1NC1=CC=CC=C1 UBHCCGHQPDLGDY-UHFFFAOYSA-N 0.000 claims 1
- WMEVWPPRBPPTRV-UHFFFAOYSA-N 1-[4-(2-anilinopyrimidin-4-yl)oxynaphthalen-1-yl]-3-[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]urea Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=CC=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 WMEVWPPRBPPTRV-UHFFFAOYSA-N 0.000 claims 1
- DBXJNQABFNNKPN-UHFFFAOYSA-N 1-[4-(2-anilinopyrimidin-4-yl)oxynaphthalen-1-yl]-3-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=CC=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 DBXJNQABFNNKPN-UHFFFAOYSA-N 0.000 claims 1
- YEMXWTXOSTZPEB-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]-3-[4-[2-(4-hydroxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=CC(O)=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 YEMXWTXOSTZPEB-UHFFFAOYSA-N 0.000 claims 1
- NSYKHTWNGWUTST-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(2,4-dihydroxyanilino)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=4C(=CC(O)=CC=4)O)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 NSYKHTWNGWUTST-UHFFFAOYSA-N 0.000 claims 1
- PHWDSIFWTAWWTO-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(2,4-dimethoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OC)=CC=C1NC1=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 PHWDSIFWTAWWTO-UHFFFAOYSA-N 0.000 claims 1
- ONVRBAWIVFIJHQ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(2,5-dimethylanilino)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=4C(=CC=C(C)C=4)C)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 ONVRBAWIVFIJHQ-UHFFFAOYSA-N 0.000 claims 1
- FTOGPTPILJXAPZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(2-chloro-4-hydroxyanilino)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=4C(=CC(O)=CC=4)Cl)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 FTOGPTPILJXAPZ-UHFFFAOYSA-N 0.000 claims 1
- KPHLJVDHJFLLFQ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(2-fluoro-4-hydroxyanilino)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=4C(=CC(O)=CC=4)F)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 KPHLJVDHJFLLFQ-UHFFFAOYSA-N 0.000 claims 1
- YSCGLTBNMHIWFZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(2-fluoroanilino)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=4C(=CC=CC=4)F)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 YSCGLTBNMHIWFZ-UHFFFAOYSA-N 0.000 claims 1
- OKZIGNXMBPUUKU-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(2-methoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC=CC=C1NC1=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 OKZIGNXMBPUUKU-UHFFFAOYSA-N 0.000 claims 1
- IHAAICCNNPXTHZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(2-methylanilino)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=4C(=CC=CC=4)C)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 IHAAICCNNPXTHZ-UHFFFAOYSA-N 0.000 claims 1
- AUNDYKNGIPQOPL-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(2-propan-2-ylanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound CC(C)C1=CC=CC=C1NC1=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 AUNDYKNGIPQOPL-UHFFFAOYSA-N 0.000 claims 1
- KNRZDHNOISHOGX-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(3,4-dimethoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=C(OC)C(OC)=CC=C1NC1=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 KNRZDHNOISHOGX-UHFFFAOYSA-N 0.000 claims 1
- VOHADHHZHANGKB-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(3-chloro-4-methoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=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 VOHADHHZHANGKB-UHFFFAOYSA-N 0.000 claims 1
- PDEVFPKHVTXCFJ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(3-fluoro-4-hydroxyanilino)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=4C=C(F)C(O)=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 PDEVFPKHVTXCFJ-UHFFFAOYSA-N 0.000 claims 1
- QJGQXNFWEATZQP-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(3-fluoroanilino)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=4C=C(F)C=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 QJGQXNFWEATZQP-UHFFFAOYSA-N 0.000 claims 1
- HICTUWNTIGIPDG-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(3-hydroxy-4-methylanilino)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=4C=C(O)C(C)=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 HICTUWNTIGIPDG-UHFFFAOYSA-N 0.000 claims 1
- HFJAHIJCNYORLF-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(3-hydroxyanilino)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=4C=C(O)C=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 HFJAHIJCNYORLF-UHFFFAOYSA-N 0.000 claims 1
- DQXDDNKSKQUYFA-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(3-methoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4N(N=C(C=4)C(C)(C)C)C=4C=CC(C)=CC=4)=CC=3)C=CN=2)=C1 DQXDDNKSKQUYFA-UHFFFAOYSA-N 0.000 claims 1
- CKGGLZNZJRZRTM-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(3-methylanilino)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=4C=C(C)C=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 CKGGLZNZJRZRTM-UHFFFAOYSA-N 0.000 claims 1
- HAKVAEKWYIEPSR-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(4-chloro-2-methylanilino)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=4C(=CC(Cl)=CC=4)C)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 HAKVAEKWYIEPSR-UHFFFAOYSA-N 0.000 claims 1
- CTDYPDKXAYTBGR-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(4-ethoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(OCC)=CC=C1NC1=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 CTDYPDKXAYTBGR-UHFFFAOYSA-N 0.000 claims 1
- VBXDFGPLWMFEQW-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(4-fluoroanilino)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=4C=CC(F)=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 VBXDFGPLWMFEQW-UHFFFAOYSA-N 0.000 claims 1
- JLWQAVMMXAMIFK-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(4-hydroxy-2-methylanilino)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=4C(=CC(O)=CC=4)C)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 JLWQAVMMXAMIFK-UHFFFAOYSA-N 0.000 claims 1
- VPQXOTKFLVTQBB-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(4-hydroxy-3-methoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=C(O)C(OC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4N(N=C(C=4)C(C)(C)C)C=4C=CC(C)=CC=4)=CC=3)C=CN=2)=C1 VPQXOTKFLVTQBB-UHFFFAOYSA-N 0.000 claims 1
- VFDXVDLISMVQFY-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(4-hydroxyanilino)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=4C=CC(O)=CC=4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 VFDXVDLISMVQFY-UHFFFAOYSA-N 0.000 claims 1
- AIRVOCDKJXGJQV-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(4-methoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(OC)=CC=C1NC1=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 AIRVOCDKJXGJQV-UHFFFAOYSA-N 0.000 claims 1
- CXRISVPNMXQWAR-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(4-methylanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1NC1=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 CXRISVPNMXQWAR-UHFFFAOYSA-N 0.000 claims 1
- 208000014085 Chronic respiratory disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 230000000840 anti-viral effect Effects 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000005713 exacerbation Effects 0.000 claims 1
- 230000012010 growth Effects 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 208000018937 joint inflammation Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 claims 1
- 229960003752 oseltamivir Drugs 0.000 claims 1
- 229960002194 oseltamivir phosphate Drugs 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229960001028 zanamivir Drugs 0.000 claims 1
- ARAIBEBZBOPLMB-UFGQHTETSA-N zanamivir Chemical compound CC(=O)N[C@@H]1[C@@H](N=C(N)N)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ARAIBEBZBOPLMB-UFGQHTETSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11183688.8 | 2011-10-03 | ||
| EP11183688.8A EP2578582A1 (en) | 2011-10-03 | 2011-10-03 | 1-Pyrazolyl-3-(4-((2-anilinopyrimidin-4-yl)oxy)napththalen-1-yl)ureas as p38 MAP kinase inhibitors |
| PCT/GB2012/052444 WO2013050756A1 (en) | 2011-10-03 | 2012-10-03 | L-pyrazolyl-3- (4- ( (2 -anilinopyrimidin- 4 - yl) oxy) napththalen- 1 - yl) ureas as p3i map kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014528403A JP2014528403A (ja) | 2014-10-27 |
| JP2014528403A5 true JP2014528403A5 (enExample) | 2015-10-08 |
| JP6023204B2 JP6023204B2 (ja) | 2016-11-09 |
Family
ID=47018246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014532481A Active JP6023204B2 (ja) | 2011-10-03 | 2012-10-03 | ｐ３ｉＭＡＰキナーゼ阻害剤としてのｌ−ピラゾリル−３−（４−（（２−アニリノピリミジン−４−イル）オキシ）ナフタレン−１−イル）尿素 |
Country Status (4)
| Country | Link |
|---|---|
| US (5) | US9475796B2 (enExample) |
| EP (2) | EP2578582A1 (enExample) |
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| AU2008337286B2 (en) | 2007-12-19 | 2014-08-07 | Cancer Research Technology Limited | Pyrido[2,3-b]pyrazine-8-substituted compounds and their use |
| JP5760010B2 (ja) | 2010-02-01 | 2015-08-05 | キャンサー・リサーチ・テクノロジー・リミテッド | １−（５−ｔｅｒｔ−ブチル−２−フェニル−２Ｈ−ピラゾール−３−イル）−３−［２−フルオロ−４−（１−メチル−２−オキソ−２，３−ジヒドロ−１Ｈ−イミダゾ［４，５−Ｂ］ピリジン−７−イルオキシ）−フェニル］−尿素および関連化合物ならびに治療におけるそれらの使用 |
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| GB201214750D0 (en) | 2012-08-17 | 2012-10-03 | Respivert Ltd | Compounds |
| GB201215357D0 (en) * | 2012-08-29 | 2012-10-10 | Respivert Ltd | Compounds |
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| US20150210722A1 (en) | 2012-08-29 | 2015-07-30 | Respivert Limited | Kinase inhibitors |
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| GB201320732D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Methods of chemical synthesis |
| WO2015092423A1 (en) | 2013-12-20 | 2015-06-25 | Respivert Limited | Urea derivatives useful as kinase inhibitors |
| PT3357919T (pt) | 2014-02-14 | 2020-02-20 | Respivert Ltd | Compostos heterocíclicos aromáticos como compostos antiinflamatórios |
| MA40774A (fr) | 2014-10-01 | 2017-08-08 | Respivert Ltd | Dérivés de diaryle-urée en tant qu'inhibiteurs de kinase p38 |
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| US20200087390A1 (en) | 2016-12-21 | 2020-03-19 | Amgen Inc. | Anti-tnf alpha antibody formulations |
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| EP2578582A1 (en) * | 2011-10-03 | 2013-04-10 | Respivert Limited | 1-Pyrazolyl-3-(4-((2-anilinopyrimidin-4-yl)oxy)napththalen-1-yl)ureas as p38 MAP kinase inhibitors |
| GB201214750D0 (en) | 2012-08-17 | 2012-10-03 | Respivert Ltd | Compounds |
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| GB201215357D0 (en) | 2012-08-29 | 2012-10-10 | Respivert Ltd | Compounds |
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| WO2014140582A1 (en) | 2013-03-14 | 2014-09-18 | Respivert Limited | Kinase inhibitors |
| BR112015024671A2 (pt) | 2013-04-02 | 2017-07-18 | Respivert Ltd | derivados de ureia úteis como inibidores de quinase |
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-
2011
- 2011-10-03 EP EP11183688.8A patent/EP2578582A1/en not_active Ceased
-
2012
- 2012-10-03 WO PCT/GB2012/052444 patent/WO2013050756A1/en not_active Ceased
- 2012-10-03 EP EP12772382.3A patent/EP2763983B1/en active Active
- 2012-10-03 US US14/349,356 patent/US9475796B2/en active Active
- 2012-10-03 JP JP2014532481A patent/JP6023204B2/ja active Active
-
2016
- 2016-09-08 US US15/259,505 patent/US9724347B2/en active Active
-
2017
- 2017-06-29 US US15/636,730 patent/US9993478B2/en active Active
-
2018
- 2018-03-19 US US15/925,384 patent/US10238658B2/en active Active
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2019
- 2019-02-26 US US16/285,560 patent/US10813932B2/en active Active
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