JP2013523803A5 - - Google Patents
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- Publication number
- JP2013523803A5 JP2013523803A5 JP2013503179A JP2013503179A JP2013523803A5 JP 2013523803 A5 JP2013523803 A5 JP 2013523803A5 JP 2013503179 A JP2013503179 A JP 2013503179A JP 2013503179 A JP2013503179 A JP 2013503179A JP 2013523803 A5 JP2013523803 A5 JP 2013523803A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- ureido
- butyl
- tert
- alkyl
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 56
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 229920006395 saturated elastomer Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- -1 n- propyl Chemical group 0.000 claims 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- BAAZNQMHGAJUKC-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-hydroxyphenyl)pyrazol-3-yl]-3-[4-[2-(methylcarbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=NC(NC(=O)NC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(O)=CC=3)=CC=2)=C1 BAAZNQMHGAJUKC-UHFFFAOYSA-N 0.000 claims 1
- UXSYOKKSKHTJCG-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]-3-[2,3-dimethyl-4-[2-(methylcarbamoylamino)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NC(NC(=O)NC)=CC(OC=2C(=C(C)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(OC)=CC=3)=CC=2)C)=C1 UXSYOKKSKHTJCG-UHFFFAOYSA-N 0.000 claims 1
- RAJPOWOOQITCKX-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]-3-[2,3-dimethyl-4-[[2-(methylcarbamoylamino)pyridin-4-yl]methoxy]phenyl]urea Chemical compound C1=NC(NC(=O)NC)=CC(COC=2C(=C(C)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(OC)=CC=3)=CC=2)C)=C1 RAJPOWOOQITCKX-UHFFFAOYSA-N 0.000 claims 1
- REMRQAOIHZTZTB-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]-3-[4-[2-(cyclopropylcarbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(OC)=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 REMRQAOIHZTZTB-UHFFFAOYSA-N 0.000 claims 1
- HOCYOIBNXANDRC-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]-3-[4-[2-(methylcarbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=NC(NC(=O)NC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(OC)=CC=3)=CC=2)=C1 HOCYOIBNXANDRC-UHFFFAOYSA-N 0.000 claims 1
- FXHRTJVOUZTXKW-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(ethylcarbamoylamino)pyridine-4-carbonyl]naphthalen-1-yl]urea Chemical compound C1=NC(NC(=O)NCC)=CC(C(=O)C=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 FXHRTJVOUZTXKW-UHFFFAOYSA-N 0.000 claims 1
- KNWDOMXCLISYFK-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[[2-(ethylcarbamoylamino)pyridin-4-yl]methyl]naphthalen-1-yl]urea Chemical compound C1=NC(NC(=O)NCC)=CC(CC=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 KNWDOMXCLISYFK-UHFFFAOYSA-N 0.000 claims 1
- QCQFJYFNNAVHMV-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylsulfonylphenyl)pyrazol-3-yl]-3-[4-[2-(carbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC1=CC=NC(NC(N)=O)=C1 QCQFJYFNNAVHMV-UHFFFAOYSA-N 0.000 claims 1
- CEDVHDWQBBGGJQ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylsulfonylphenyl)pyrazol-3-yl]-3-[4-[2-(methylcarbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=NC(NC(=O)NC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(=CC=3)S(C)(=O)=O)=CC=2)=C1 CEDVHDWQBBGGJQ-UHFFFAOYSA-N 0.000 claims 1
- XEWJIUDGHQKAPZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methoxypyridin-3-yl)pyrazol-3-yl]-3-[2,3-dimethyl-4-[2-(methylcarbamoylamino)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NC(NC(=O)NC)=CC(OC=2C(=C(C)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(OC)=CC=3)=CC=2)C)=C1 XEWJIUDGHQKAPZ-UHFFFAOYSA-N 0.000 claims 1
- ZXPAZNSFKLHNLZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methoxypyridin-3-yl)pyrazol-3-yl]-3-[2,3-dimethyl-4-[[2-(methylcarbamoylamino)pyridin-4-yl]methoxy]phenyl]urea Chemical compound C1=NC(NC(=O)NC)=CC(COC=2C(=C(C)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(OC)=CC=3)=CC=2)C)=C1 ZXPAZNSFKLHNLZ-UHFFFAOYSA-N 0.000 claims 1
- FUDOCSOWCGXJEP-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-oxo-1h-pyridin-3-yl)pyrazol-3-yl]-3-[2,3-dimethyl-4-[2-(methylcarbamoylamino)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NC(NC(=O)NC)=CC(OC=2C(=C(C)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(O)=CC=3)=CC=2)C)=C1 FUDOCSOWCGXJEP-UHFFFAOYSA-N 0.000 claims 1
- TXLZRMRCAWLPKZ-UHFFFAOYSA-N 3-[4-[4-[[5-tert-butyl-2-(4-hydroxyphenyl)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(O)=CC=3)=CC=2)=C1 TXLZRMRCAWLPKZ-UHFFFAOYSA-N 0.000 claims 1
- CGYNVARIYRLGPV-UHFFFAOYSA-N 3-[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-1,1-dimethylurea Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)N(C)C)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 CGYNVARIYRLGPV-UHFFFAOYSA-N 0.000 claims 1
- QLCOCTLVZFWKRP-UHFFFAOYSA-N 3-[4-[4-[[5-tert-butyl-2-(4-methylsulfonylphenyl)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(=CC=3)S(C)(=O)=O)=CC=2)=C1 QLCOCTLVZFWKRP-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
- 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
- 206010014561 Emphysema Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000015634 Rectal Neoplasms Diseases 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
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 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
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 208000029771 childhood onset asthma Diseases 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 208000010247 contact dermatitis Diseases 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
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000000155 isotopic effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 claims 1
- NOVWYWPZOJAODC-UHFFFAOYSA-N n-[4-[4-[(2,5-diphenylpyrazol-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=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)=C1 NOVWYWPZOJAODC-UHFFFAOYSA-N 0.000 claims 1
- SPZXTRXIPUADKG-UHFFFAOYSA-N n-[4-[4-[(5-tert-butyl-2-thiophen-2-ylpyrazol-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=3SC=CC=3)=CC=2)=C1 SPZXTRXIPUADKG-UHFFFAOYSA-N 0.000 claims 1
- PDUPWPQJHADVSR-UHFFFAOYSA-N n-[4-[4-[[2-(4-aminophenyl)-5-tert-butylpyrazol-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(N)=CC=3)=CC=2)=C1 PDUPWPQJHADVSR-UHFFFAOYSA-N 0.000 claims 1
- OOVJKYSJTMRXCK-UHFFFAOYSA-N n-[4-[4-[[5-(1-adamantyl)-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)C34CC5CC(CC(C5)C3)C4)C=3C=CC(C)=CC=3)=CC=2)=C1 OOVJKYSJTMRXCK-UHFFFAOYSA-N 0.000 claims 1
- GKDITMSSYMDGEE-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3,4-dichlorophenyl)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=C(Cl)C(Cl)=CC=3)=CC=2)=C1 GKDITMSSYMDGEE-UHFFFAOYSA-N 0.000 claims 1
- DEORIXCEYCRSSH-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3,4-dimethoxyphenyl)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=C(OC)C(OC)=CC=3)=CC=2)=C1 DEORIXCEYCRSSH-UHFFFAOYSA-N 0.000 claims 1
- YVPZFRVWTNGMDX-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3,5-dimethoxyphenyl)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=C(OC)C=C(OC)C=3)=CC=2)=C1 YVPZFRVWTNGMDX-UHFFFAOYSA-N 0.000 claims 1
- SIEQNPMZCSPWBA-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3-chloro-4-hydroxyphenyl)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=C(Cl)C(O)=CC=3)=CC=2)=C1 SIEQNPMZCSPWBA-UHFFFAOYSA-N 0.000 claims 1
- UDVGHGVLKNJSGE-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3-chloro-4-hydroxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]morpholine-4-carboxamide Chemical compound C=1C=C(O)C(Cl)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC(C=1)=CC=NC=1NC(=O)N1CCOCC1 UDVGHGVLKNJSGE-UHFFFAOYSA-N 0.000 claims 1
- MUXUVQHJDDBLAQ-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3-chloro-4-methoxyphenyl)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=C(Cl)C(OC)=CC=3)=CC=2)=C1 MUXUVQHJDDBLAQ-UHFFFAOYSA-N 0.000 claims 1
- SONLMYWONGIPSC-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3-hydroxyphenyl)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=C(O)C=CC=3)=CC=2)=C1 SONLMYWONGIPSC-UHFFFAOYSA-N 0.000 claims 1
- KZHKFNGYOQGDGC-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3-methoxyphenyl)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=C(OC)C=CC=3)=CC=2)=C1 KZHKFNGYOQGDGC-UHFFFAOYSA-N 0.000 claims 1
- LNUAWYSLDCYQNG-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-chlorophenyl)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(Cl)=CC=3)=CC=2)=C1 LNUAWYSLDCYQNG-UHFFFAOYSA-N 0.000 claims 1
- XCORBYUCTBFULC-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-hydroxyphenyl)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(O)=CC=3)=CC=2)=C1 XCORBYUCTBFULC-UHFFFAOYSA-N 0.000 claims 1
- GJVOUJIAGSXPAY-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-hydroxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]pyrrolidine-1-carboxamide Chemical compound C=1C=C(O)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC(C=1)=CC=NC=1NC(=O)N1CCCC1 GJVOUJIAGSXPAY-UHFFFAOYSA-N 0.000 claims 1
- YUWFIAFUXFJDSK-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-hydroxyacetamide Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)CO)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 YUWFIAFUXFJDSK-UHFFFAOYSA-N 0.000 claims 1
- ACGOXIBULCMWDN-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)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(OC)=CC=3)=CC=2)=C1 ACGOXIBULCMWDN-UHFFFAOYSA-N 0.000 claims 1
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- PNELWARZRKUBQR-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]morpholine-4-carboxamide Chemical compound C1=CC(OC)=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 PNELWARZRKUBQR-UHFFFAOYSA-N 0.000 claims 1
- UUSMBDZMBKUGSR-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]pyrrolidine-1-carboxamide Chemical compound C1=CC(OC)=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 UUSMBDZMBKUGSR-UHFFFAOYSA-N 0.000 claims 1
- JWQPLLQYCQUFNM-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalene-1-carbonyl]pyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(C(=O)C=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 JWQPLLQYCQUFNM-UHFFFAOYSA-N 0.000 claims 1
- QEQJMKODCWIMAU-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylsulfanylphenyl)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(SC)=CC=3)=CC=2)=C1 QEQJMKODCWIMAU-UHFFFAOYSA-N 0.000 claims 1
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- XCJUKXAWFBFKDY-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylsulfonylphenyl)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(=CC=3)S(C)(=O)=O)=CC=2)=CC=N1 XCJUKXAWFBFKDY-UHFFFAOYSA-N 0.000 claims 1
- MVBMAFBEMMLDKV-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylthiophen-2-yl)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=3SC=C(C)C=3)=CC=2)=C1 MVBMAFBEMMLDKV-UHFFFAOYSA-N 0.000 claims 1
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- DRJCTBLDJCCETA-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-[4-(methanesulfonamido)phenyl]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(NS(C)(=O)=O)=CC=3)=CC=2)=C1 DRJCTBLDJCCETA-UHFFFAOYSA-N 0.000 claims 1
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- UMYVLHJHBAEUEE-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-[4-(trifluoromethoxy)phenyl]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(OC(F)(F)F)=CC=3)=CC=2)=C1 UMYVLHJHBAEUEE-UHFFFAOYSA-N 0.000 claims 1
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- NXERXVHEQFSTEQ-UHFFFAOYSA-N n-[6-[4-[[5-tert-butyl-2-(4-methylsulfonylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-4-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(=CC=3)S(C)(=O)=O)=CC=2)=N1 NXERXVHEQFSTEQ-UHFFFAOYSA-N 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
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- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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| PCT/GB2011/050706 WO2011124930A1 (en) | 2010-04-08 | 2011-04-08 | P38 map kinase inhibitors |
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| GB0905955D0 (en) | 2009-04-06 | 2009-05-20 | Respivert Ltd | Novel compounds |
| 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 |
| GB201005589D0 (en) | 2010-04-01 | 2010-05-19 | Respivert Ltd | Novel compounds |
| JP5787976B2 (ja) | 2010-04-08 | 2015-09-30 | レスピバート・リミテツド | Ｐ３８ｍａｐキナーゼ阻害剤としてのピラゾリルウレア |
| GB201010193D0 (en) | 2010-06-17 | 2010-07-21 | Respivert Ltd | Medicinal use |
| WO2011158044A2 (en) | 2010-06-17 | 2011-12-22 | Respivert Limited | Respiratory formulations and compounds for use therein |
| KR101995274B1 (ko) | 2011-10-03 | 2019-07-02 | 레스피버트 리미티드 | P38 map 키나제 저해제인 1-피라졸릴-3-(4-((2-아닐리노피리미딘-4-일)옥시)나프탈렌-1-일) 우레아 |
| 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 |
| UA115320C2 (uk) * | 2011-12-09 | 2017-10-25 | К'Єзі Фармачеутічі С.П.А. | Інгібітори кінази |
| MY167216A (en) * | 2011-12-09 | 2018-08-14 | Chiesi Farm Spa | Kinase inhibitors |
| GB201214750D0 (en) | 2012-08-17 | 2012-10-03 | Respivert Ltd | Compounds |
| US20150225373A1 (en) * | 2012-08-29 | 2015-08-13 | Respivert Limited | Kinase inhibitors |
| US9783556B2 (en) | 2012-08-29 | 2017-10-10 | Respivert Limited | Kinase inhibitors |
| EP2890460B1 (en) | 2012-08-29 | 2017-02-22 | Respivert Limited | Kinase inhibitors |
| GB201215357D0 (en) | 2012-08-29 | 2012-10-10 | Respivert Ltd | Compounds |
| US9732063B2 (en) | 2012-11-16 | 2017-08-15 | Respivert Limited | Kinase inhibitors |
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| PL3417851T3 (pl) | 2013-09-09 | 2020-12-14 | Peloton Therapeutics, Inc. | Etery arylowe i ich zastosowanie |
| GB201320732D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Methods of chemical synthesis |
| GB201320729D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| CA2934199A1 (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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| US10512626B2 (en) | 2015-03-11 | 2019-12-24 | Peloton Therapeautics, Inc. | Compositions for use in treating glioblastoma |
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| WO2016144825A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Aromatic compounds and uses thereof |
| WO2016168510A1 (en) | 2015-04-17 | 2016-10-20 | Peloton Therapeutics, Inc. | Combination therapy of a hif-2-alpha inhibitor and an immunotherapeutic agent and uses thereof |
| EA201892213A1 (ru) | 2016-04-06 | 2019-05-31 | Топайверт Фарма Лимитед | Ингибиторы киназ |
| CA3121202A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN110041173A (zh) * | 2019-05-10 | 2019-07-23 | 贵州医科大学 | 一种新的白藜芦醇及其衍生物合成方法及应用 |
| CA3140017A1 (en) * | 2019-07-19 | 2021-01-28 | Aurore HICK | Polyaromatic urea derivatives and their use in the treatment of muscle diseases |
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| UA73492C2 (en) | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| ATE278674T1 (de) | 1999-03-12 | 2004-10-15 | Boehringer Ingelheim Pharma | Heterocyklischer harnstoff und verwandte verbindungen als entzündungshemmende mittel |
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| EA012119B1 (ru) | 2004-08-12 | 2009-08-28 | Пфайзер Инк. | ПРОИЗВОДНЫЕ ТРИАЗОЛОПИРИДИНСУЛЬФАНИЛА В КАЧЕСТВЕ ИНГИБИТОРОВ p38 MAP КИНАЗЫ |
| CA2592118C (en) | 2004-12-23 | 2015-11-17 | Deciphera Pharmaceuticals, Llc | Urea derivatives as enzyme modulators |
| GB0500435D0 (en) | 2005-01-10 | 2005-02-16 | Novartis Ag | Organic compounds |
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| US20110195110A1 (en) | 2005-12-01 | 2011-08-11 | Roger Smith | Urea compounds useful in the treatment of cancer |
| CN101437512A (zh) | 2006-01-27 | 2009-05-20 | 阿雷生物药品公司 | 葡萄糖激酶活化剂 |
| JP2009525279A (ja) | 2006-01-30 | 2009-07-09 | アイアールエム・リミテッド・ライアビリティ・カンパニー | Ｐｐａｒモジュレーターとしてのスピロイミダゾール誘導体 |
| CA2640665A1 (en) | 2006-02-10 | 2007-08-16 | Pfizer Products Inc. | Pyridinone pyrazole urea and pyrimidinone pyrazole urea derivatives |
| AR065858A1 (es) | 2007-03-29 | 2009-07-08 | Sanofi Aventis | Metodo para preparar el inhibidor de triptasa [ 4-(5-aminoetil-2-fluoro-fenil)-piperidin-1-il]-(4-bromo-3-metil-5-propoxi-tiofen-2-il)-metanona. |
| WO2008125014A1 (fr) | 2007-04-13 | 2008-10-23 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. | Composés d'urée, leurs procédés de préparation et leurs utilisations pharmaceutiques |
| NZ586418A (en) | 2007-12-19 | 2012-09-28 | Cancer Rec Tech Ltd | Pyrido[2,3-b]pyrazine-8-substituted compounds and their use |
| EP3147281A1 (en) | 2008-03-17 | 2017-03-29 | Ambit Biosciences Corporation | Quinazoline derivatives as raf kinase modulators and methods of use thereof |
| GB0818033D0 (en) | 2008-10-02 | 2008-11-05 | Respivert Ltd | Novel compound |
| JP2012504591A (ja) | 2008-10-02 | 2012-02-23 | レスピバート・リミテツド | ｐ３８ＭＡＰキナーゼ阻害剤 |
| MX2011006219A (es) | 2008-12-11 | 2011-06-28 | Respivert Ltd | Inhibidores de la proteina cinasa activada por el mitogeno p38. |
| GB0905955D0 (en) | 2009-04-06 | 2009-05-20 | Respivert Ltd | Novel compounds |
| GB0921730D0 (en) | 2009-12-11 | 2010-01-27 | Respivert Ltd | Method of treatment |
| GB201005589D0 (en) | 2010-04-01 | 2010-05-19 | Respivert Ltd | Novel compounds |
| JP5787976B2 (ja) | 2010-04-08 | 2015-09-30 | レスピバート・リミテツド | Ｐ３８ｍａｐキナーゼ阻害剤としてのピラゾリルウレア |
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2011
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- 2011-04-08 WO PCT/GB2011/050706 patent/WO2011124930A1/en not_active Ceased
- 2011-04-08 EP EP11729448.8A patent/EP2556068B1/en active Active
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