JP2017502033A5 - - Google Patents
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- Publication number
- JP2017502033A5 JP2017502033A5 JP2016541566A JP2016541566A JP2017502033A5 JP 2017502033 A5 JP2017502033 A5 JP 2017502033A5 JP 2016541566 A JP2016541566 A JP 2016541566A JP 2016541566 A JP2016541566 A JP 2016541566A JP 2017502033 A5 JP2017502033 A5 JP 2017502033A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- tert
- butyl
- amino
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000012453 solvate Substances 0.000 claims description 18
- 230000000155 isotopic effect Effects 0.000 claims description 15
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000013066 combination product Substances 0.000 claims description 6
- 229940127555 combination product Drugs 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 76
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 56
- -1 -C (CH 3) 2 -C≡CH Chemical group 0.000 claims 55
- 125000005843 halogen group Chemical group 0.000 claims 36
- 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 33
- 125000003545 alkoxy group Chemical group 0.000 claims 32
- 125000001424 substituent group Chemical group 0.000 claims 31
- 125000000623 heterocyclic group Chemical group 0.000 claims 27
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 27
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 24
- 239000004202 carbamide Substances 0.000 claims 24
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 23
- 229920006395 saturated elastomer Polymers 0.000 claims 22
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 125000002947 alkylene group Chemical group 0.000 claims 19
- 229910052760 oxygen Inorganic materials 0.000 claims 19
- 125000005842 heteroatom Chemical group 0.000 claims 18
- 125000004043 oxo group Chemical group O=* 0.000 claims 17
- 229910052717 sulfur Inorganic materials 0.000 claims 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 7
- 238000006243 chemical reaction Methods 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 3
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- UQPHQMHZGRKBGL-UHFFFAOYSA-N C1COCCN1CCOC2=CC(=CC(=C2)NC3=CC=CC=N3)C(F)(F)F Chemical compound C1COCCN1CCOC2=CC(=CC(=C2)NC3=CC=CC=N3)C(F)(F)F UQPHQMHZGRKBGL-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000015943 Coeliac disease Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 206010064930 age-related macular degeneration Diseases 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 201000005667 central retinal vein occlusion Diseases 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 239000012634 fragment Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000002780 macular degeneration Diseases 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 208000004644 retinal vein occlusion Diseases 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 1
- UDYNZGINEPJGRE-UHFFFAOYSA-N 1-(3-tert-butyl-5-dimethylphosphorylphenyl)-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C=C(C1)P(=O)(C)C)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)OCCOCCOCCOC)OC UDYNZGINEPJGRE-UHFFFAOYSA-N 0.000 claims 1
- VCPDJHZTDNFZAP-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxy-3-methylsulfinylphenyl)-3-[4-[2-(3,5-dimethoxyanilino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)OC)OC)OC)S(=O)C VCPDJHZTDNFZAP-UHFFFAOYSA-N 0.000 claims 1
- MFAOSZKHEDBBHJ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxy-3-methylsulfinylphenyl)-3-[4-[2-(3-methoxyanilino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC=C1)OC)OC)S(=O)C MFAOSZKHEDBBHJ-UHFFFAOYSA-N 0.000 claims 1
- IZLRLLYJGJIQME-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxy-3-methylsulfinylphenyl)-3-[4-[2-(pyridin-2-ylmethylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NCC1=NC=CC=C1)OC)S(=O)C IZLRLLYJGJIQME-UHFFFAOYSA-N 0.000 claims 1
- COGAGZKBVNKUKW-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxy-3-methylsulfinylphenyl)-3-[4-[2-[(7-methyl-1H-indazol-5-yl)amino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC=1C=C2C=NNC2=C(C1)C)OC)S(=O)C COGAGZKBVNKUKW-UHFFFAOYSA-N 0.000 claims 1
- OATRTTMQLCPVDR-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxy-3-methylsulfinylphenyl)-3-[4-[2-[3-(2-morpholin-4-ylethoxy)-5-(trifluoromethyl)anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)C(F)(F)F)OCCN1CCOCC1)OC)S(=O)C OATRTTMQLCPVDR-UHFFFAOYSA-N 0.000 claims 1
- XNABWRPORLLVHI-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxy-3-methylsulfinylphenyl)-3-[4-[2-[3-cyano-5-(2-morpholin-4-ylethoxy)anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)OCCN1CCOCC1)C#N)OC)S(=O)C XNABWRPORLLVHI-UHFFFAOYSA-N 0.000 claims 1
- ISTSMZAMIIBAPY-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxy-3-methylsulfinylphenyl)-3-[4-[2-[3-cyano-5-(3-morpholin-4-ylpropoxy)anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)OCCCN1CCOCC1)C#N)OC)S(=O)C ISTSMZAMIIBAPY-UHFFFAOYSA-N 0.000 claims 1
- WUVDZGUGFJPSSF-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxy-3-methylsulfinylphenyl)-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)OCCOCCOCCOC)OC)OC)S(=O)C WUVDZGUGFJPSSF-UHFFFAOYSA-N 0.000 claims 1
- HMXFKOQFBKZEPI-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(1,2-oxazol-4-ylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC=1C=NOC1)OC)P(=O)(C)C HMXFKOQFBKZEPI-UHFFFAOYSA-N 0.000 claims 1
- KZDDBWQFIJBYTD-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=CC2=C(OCCO2)C=C1)OC)P(=O)(C)C KZDDBWQFIJBYTD-UHFFFAOYSA-N 0.000 claims 1
- ZSOXEUNLGBKXMJ-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(2-methoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=C(C=CC=C1)OC)OC)P(=O)(C)C ZSOXEUNLGBKXMJ-UHFFFAOYSA-N 0.000 claims 1
- ZXMIVKUDVFVXFG-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(2-pyrazol-1-ylethylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound N1(N=CC=C1)CCNC1=NC=CC(=N1)OC1=CC=C(C2=CC=CC=C12)NC(=O)NC1=C(C(=CC(=C1)C(C)(C)C)P(=O)(C)C)OC ZXMIVKUDVFVXFG-UHFFFAOYSA-N 0.000 claims 1
- ZLSAOTHLEXBFJL-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(3,4-dimethoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=CC(=C(C=C1)OC)OC)OC)P(=O)(C)C ZLSAOTHLEXBFJL-UHFFFAOYSA-N 0.000 claims 1
- CDHAQCXQRLQAJD-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(3,5-dimethoxyanilino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)OC)OC)OC)P(=O)(C)C CDHAQCXQRLQAJD-UHFFFAOYSA-N 0.000 claims 1
- ZOJJTNITQOBIGV-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(3,5-dimethoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=CC(=CC(=C1)OC)OC)OC)P(=O)(C)C ZOJJTNITQOBIGV-UHFFFAOYSA-N 0.000 claims 1
- CMOGZZSEIWVJPZ-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(3,5-dimethylanilino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)C)C)OC)P(=O)(C)C CMOGZZSEIWVJPZ-UHFFFAOYSA-N 0.000 claims 1
- LCWNPJCUHVJNEJ-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(3-dimethylphosphoryl-5-methoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=CC(=CC(=C1)OC)P(=O)(C)C)OC)P(=O)(C)C LCWNPJCUHVJNEJ-UHFFFAOYSA-N 0.000 claims 1
- PMWVLGBEBHDVRO-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(3-fluoro-5-methoxyanilino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)OC)F)OC)P(=O)(C)C PMWVLGBEBHDVRO-UHFFFAOYSA-N 0.000 claims 1
- LNWNZISSSWSPFR-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(3-methoxyanilino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC=C1)OC)OC)P(=O)(C)C LNWNZISSSWSPFR-UHFFFAOYSA-N 0.000 claims 1
- OSEFLDPODJLFNJ-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(3-methoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=CC(=CC=C1)OC)OC)P(=O)(C)C OSEFLDPODJLFNJ-UHFFFAOYSA-N 0.000 claims 1
- CYJRHYSLMRHELZ-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(4-methoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=CC=C(C=C1)OC)OC)P(=O)(C)C CYJRHYSLMRHELZ-UHFFFAOYSA-N 0.000 claims 1
- UBFDBKBPRDRVHH-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(dimethylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)N(C)C)OC)P(=O)(C)C UBFDBKBPRDRVHH-UHFFFAOYSA-N 0.000 claims 1
- XZQTYVLGJRZSGX-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(oxan-4-ylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1CCOCC1)OC)P(=O)(C)C XZQTYVLGJRZSGX-UHFFFAOYSA-N 0.000 claims 1
- VMFBKDNUNVTPGE-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(pyrazin-2-ylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=NC=CN=C1)OC)P(=O)(C)C VMFBKDNUNVTPGE-UHFFFAOYSA-N 0.000 claims 1
- VDXSYHRLAJTEME-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(pyrazin-2-ylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=NC=CN=C1)OC)P(=O)(C)C VDXSYHRLAJTEME-UHFFFAOYSA-N 0.000 claims 1
- QKUJCJHYKSICNQ-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(pyridin-2-ylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=NC=CC=C1)OC)P(=O)(C)C QKUJCJHYKSICNQ-UHFFFAOYSA-N 0.000 claims 1
- FYISVERUOWLPAV-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(pyridin-2-ylmethylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NCC1=NC=CC=C1)OC)P(=O)(C)C FYISVERUOWLPAV-UHFFFAOYSA-N 0.000 claims 1
- PJUSCKOQLSMBPU-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(pyridin-2-ylmethylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NCC1=NC=CC=C1)OC)P(=O)(C)C PJUSCKOQLSMBPU-UHFFFAOYSA-N 0.000 claims 1
- IUGSLDDVTYDVLR-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(pyridin-3-ylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=NC=CC=1)OC)P(=O)(C)C IUGSLDDVTYDVLR-UHFFFAOYSA-N 0.000 claims 1
- XSGGMXMDGHRDNR-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-(pyrimidin-5-ylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC=1C=NC=NC=1)OC)P(=O)(C)C XSGGMXMDGHRDNR-UHFFFAOYSA-N 0.000 claims 1
- FVXZVUYOKYLSPP-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[(1-methylpiperidin-4-yl)amino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1CCN(CC1)C)OC)P(=O)(C)C FVXZVUYOKYLSPP-UHFFFAOYSA-N 0.000 claims 1
- PKYUBPMHYGOYDI-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC=1C=NN(C1)C)OC)P(=O)(C)C PKYUBPMHYGOYDI-UHFFFAOYSA-N 0.000 claims 1
- RMNHCNRLPDKPEY-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[(2-methyltriazol-4-yl)amino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=NN(N=C1)C)OC)P(=O)(C)C RMNHCNRLPDKPEY-UHFFFAOYSA-N 0.000 claims 1
- UNZNAJIUSWOADN-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[(2-methyltriazol-4-yl)amino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=NN(N=C1)C)OC)P(=O)(C)C UNZNAJIUSWOADN-UHFFFAOYSA-N 0.000 claims 1
- NZCDZOUZHSNTTN-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[(2-oxo-1,3-dihydroindol-6-yl)amino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=CC=C2CC(NC2=C1)=O)OC)P(=O)(C)C NZCDZOUZHSNTTN-UHFFFAOYSA-N 0.000 claims 1
- SQTVPCJHGCELRZ-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[(3-oxo-1,2-dihydroisoindol-5-yl)amino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC=1C=C2C(NCC2=CC=1)=O)OC)P(=O)(C)C SQTVPCJHGCELRZ-UHFFFAOYSA-N 0.000 claims 1
- UZRIDTFIIDOBLB-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[(5-methoxypyridin-3-yl)amino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=NC=C(C=1)OC)OC)P(=O)(C)C UZRIDTFIIDOBLB-UHFFFAOYSA-N 0.000 claims 1
- DATNVJMWIKFHGB-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[(7-methyl-1H-indazol-5-yl)amino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC=1C=C2C=NNC2=C(C=1)C)OC)P(=O)(C)C DATNVJMWIKFHGB-UHFFFAOYSA-N 0.000 claims 1
- LHGZMJBASKEVJS-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[3-(dimethylsulfamoyl)-5-methoxyanilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=C(C=C(C=1)OC)S(=O)(=O)N(C)C)=O)OC)P(=O)(C)C LHGZMJBASKEVJS-UHFFFAOYSA-N 0.000 claims 1
- KXMYGYOLZHGXGW-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[3-methoxy-4-(4-methylpiperazine-1-carbonyl)anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=C(C=C1)C(=O)N1CCN(CC1)C)OC)OC)P(=O)(C)C KXMYGYOLZHGXGW-UHFFFAOYSA-N 0.000 claims 1
- DHSZWTFDQUUKJT-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)OCCOCCOCCOC)OC)OC)P(=O)(C)C DHSZWTFDQUUKJT-UHFFFAOYSA-N 0.000 claims 1
- WBBZJXHOJATBAX-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=CC(=CC(=C1)OCCOCCOCCOC)OC)OC)P(=O)(C)C WBBZJXHOJATBAX-UHFFFAOYSA-N 0.000 claims 1
- IEMKOBYQSRDPTC-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[3-methoxy-5-[methyl(3-morpholin-4-ylpropyl)sulfamoyl]anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)S(N(CCCN1CCOCC1)C)(=O)=O)OC)OC)P(=O)(C)C IEMKOBYQSRDPTC-UHFFFAOYSA-N 0.000 claims 1
- SKFXDJPTJSNQFF-OAQYLSRUSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[[(3R)-oxolan-3-yl]amino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)N[C@H]1COCC1)OC)P(=O)(C)C SKFXDJPTJSNQFF-OAQYLSRUSA-N 0.000 claims 1
- SKFXDJPTJSNQFF-NRFANRHFSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[2-[[(3S)-oxolan-3-yl]amino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)N[C@@H]1COCC1)OC)P(=O)(C)C SKFXDJPTJSNQFF-NRFANRHFSA-N 0.000 claims 1
- VHWVIZQDQIIAGK-UHFFFAOYSA-N 1-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)-3-[4-[6-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC=NC(=C1)NC1=CC(=CC(=C1)OCCOCCOCCOC)OC)OC)P(=O)(C)C VHWVIZQDQIIAGK-UHFFFAOYSA-N 0.000 claims 1
- UHIRRHIZJMTBGU-UHFFFAOYSA-N 1-[4-[2-(benzylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]-3-(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)urea Chemical compound C(C1=CC=CC=C1)NC1=NC=CC(=N1)OC1=CC=C(C2=CC=CC=C12)NC(=O)NC1=C(C(=CC(=C1)C(C)(C)C)P(=O)(C)C)OC UHIRRHIZJMTBGU-UHFFFAOYSA-N 0.000 claims 1
- RGUUKEMJOZEWCO-UHFFFAOYSA-N 1-[5-tert-butyl-2-methoxy-3-(2-morpholin-4-yl-2-oxoethyl)phenyl]-3-[4-[2-(3-methoxyanilino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC=C1)OC)OC)CC(=O)N1CCOCC1 RGUUKEMJOZEWCO-UHFFFAOYSA-N 0.000 claims 1
- UYBFGBPGWZDBPF-UHFFFAOYSA-N 1-[5-tert-butyl-2-methoxy-3-(methylsulfonylmethyl)phenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)OCCOCCOCCOC)OC)OC)CS(=O)(=O)C UYBFGBPGWZDBPF-UHFFFAOYSA-N 0.000 claims 1
- ZBEDFVWDQXBYHG-UHFFFAOYSA-N 1-[5-tert-butyl-3-(dimethylphosphorylmethoxy)-2-methoxyphenyl]-3-[4-[2-(3,5-dimethoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=CC(=CC(=C1)OC)OC)OC)OCP(=O)(C)C ZBEDFVWDQXBYHG-UHFFFAOYSA-N 0.000 claims 1
- SUCOEVXSLGWMLL-UHFFFAOYSA-N 1-[5-tert-butyl-3-(dimethylphosphorylmethoxy)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=NC(=NC=C1)NC1=CC(=CC(=C1)OCCOCCOCCOC)OC)OC)OCP(=O)(C)C SUCOEVXSLGWMLL-UHFFFAOYSA-N 0.000 claims 1
- KDECLMGBTBGDLA-UHFFFAOYSA-N 1-[5-tert-butyl-3-(dimethylphosphorylmethyl)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)OCCOCCOCCOC)OC)OC)CP(=O)(C)C KDECLMGBTBGDLA-UHFFFAOYSA-N 0.000 claims 1
- OVSKYGSFWWLHDK-UHFFFAOYSA-N 2-[5-tert-butyl-2-methoxy-3-[[4-[2-(3-methoxyanilino)pyridin-4-yl]oxynaphthalen-1-yl]carbamoylamino]phenyl]-N,N-dimethylacetamide Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)CC(=O)N(C)C)OC)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC=C1)OC OVSKYGSFWWLHDK-UHFFFAOYSA-N 0.000 claims 1
- YEJMNHVCRNVQKA-UHFFFAOYSA-N 2-[5-tert-butyl-2-methoxy-3-[[4-[2-(3-methoxyanilino)pyridin-4-yl]oxynaphthalen-1-yl]carbamoylamino]phenyl]acetamide Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)CC(=O)N)OC)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC=C1)OC YEJMNHVCRNVQKA-UHFFFAOYSA-N 0.000 claims 1
- HKLXOYSAWIZPRF-UHFFFAOYSA-N 2-[5-tert-butyl-3-[[4-[2-(3,5-dimethoxyanilino)pyridin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-2-methoxyphenyl]acetamide Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)CC(=O)N)OC)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=CC(=C1)OC)OC HKLXOYSAWIZPRF-UHFFFAOYSA-N 0.000 claims 1
- ZWBFERVFLYUUSC-UHFFFAOYSA-N 3-[[4-[4-[(5-tert-butyl-2-methoxy-3-methylsulfinylphenyl)carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxy-N-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]benzamide Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=C(C(=O)NCCOCCOCCOC)C=C(C1)OC)=O)OC)S(=O)C ZWBFERVFLYUUSC-UHFFFAOYSA-N 0.000 claims 1
- ZZOHRDNQKJSEFE-UHFFFAOYSA-N 3-[[4-[4-[(5-tert-butyl-2-methoxy-3-methylsulfinylphenyl)carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxybenzamide Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=C(C(=O)N)C=C(C1)OC)=O)OC)S(=O)C ZZOHRDNQKJSEFE-UHFFFAOYSA-N 0.000 claims 1
- NNCSGAQSWJJHTN-UHFFFAOYSA-N 3-[[4-[4-[(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-ethynyl-N-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]benzamide Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=C(C(=O)NCCOCCOCCOC)C=C(C1)C#C)=O)OC)P(=O)(C)C NNCSGAQSWJJHTN-UHFFFAOYSA-N 0.000 claims 1
- NFMGRLANJRZACE-UHFFFAOYSA-N 3-[[4-[4-[(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxybenzamide Chemical compound NC(=O)C1=CC(OC)=CC(NC=2N=CC=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(C=C(C=4)C(C)(C)C)P(C)(C)=O)OC)=CC=3)C=2)=C1 NFMGRLANJRZACE-UHFFFAOYSA-N 0.000 claims 1
- FMPCVWJDAXDAGO-UHFFFAOYSA-N 3-[[4-[4-[(5-tert-butyl-3-dimethylphosphoryl-2-methoxyphenyl)carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-methyl-5-[(4-methylpiperazin-1-yl)methyl]benzamide Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=C(C(=O)NC)C=C(C1)CN1CCN(CC1)C)=O)OC)P(=O)(C)C FMPCVWJDAXDAGO-UHFFFAOYSA-N 0.000 claims 1
- BWYBMYLWQUNHOD-UHFFFAOYSA-N 3-[[4-[4-[[3-(2-amino-2-oxoethyl)-5-tert-butyl-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxybenzamide Chemical compound NC(CC=1C(=C(C=C(C1)C(C)(C)C)NC(NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=C(C(=O)N)C=C(C1)OC)=O)OC)=O BWYBMYLWQUNHOD-UHFFFAOYSA-N 0.000 claims 1
- SWXHUJWGBIVLTE-UHFFFAOYSA-N 3-[[4-[4-[[3-(2-amino-2-oxoethyl)-5-tert-butyl-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-[3-hydroxy-2,2-bis(hydroxymethyl)propyl]-5-methoxybenzamide Chemical compound NC(CC=1C(=C(C=C(C1)C(C)(C)C)NC(NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=C(C(=O)NCC(CO)(CO)CO)C=C(C1)OC)=O)OC)=O SWXHUJWGBIVLTE-UHFFFAOYSA-N 0.000 claims 1
- MYCMOLBEOQHIBA-UHFFFAOYSA-N 3-[[4-[4-[[3-(acetamidomethyl)-5-tert-butyl-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxybenzamide Chemical compound C(C)(=O)NCC=1C(=C(C=C(C1)C(C)(C)C)NC(NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=C(C(=O)N)C=C(C1)OC)=O)OC MYCMOLBEOQHIBA-UHFFFAOYSA-N 0.000 claims 1
- UDFUHXXSMWLHAD-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-3-(1,3-dihydroxypropan-2-yloxy)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxybenzamide Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=C(C(=O)N)C=C(C1)OC)=O)OC)OC(CO)CO UDFUHXXSMWLHAD-UHFFFAOYSA-N 0.000 claims 1
- MXYIYYSFYXHLSZ-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-3-(2-hydroxyethoxy)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxybenzamide Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=C(C(=O)N)C=C(C1)OC)=O)OC)OCCO MXYIYYSFYXHLSZ-UHFFFAOYSA-N 0.000 claims 1
- GRWHPARMDNQEJW-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-3-[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxybenzamide Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=C(C(=O)N)C=C(C1)OC)=O)OC)OCC(CO)(CO)CO GRWHPARMDNQEJW-UHFFFAOYSA-N 0.000 claims 1
- FPWCREKHIZDTGO-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-3-[[[2-(dimethylamino)acetyl]amino]methyl]-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxy-N-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]benzamide Chemical compound C(C)(C)(C)C=1C=C(C(=C(C1)NC(NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC=1C=C(C(=O)NCCOCCOCCOC)C=C(C1)OC)=O)OC)CNC(CN(C)C)=O FPWCREKHIZDTGO-UHFFFAOYSA-N 0.000 claims 1
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| PT3357919T (pt) | 2014-02-14 | 2020-02-20 | Respivert Ltd | Compostos heterocíclicos aromáticos como compostos antiinflamatórios |
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| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
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Family Cites Families (61)
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| EP1028953A1 (en) | 1997-11-03 | 2000-08-23 | Boehringer Ingelheim Pharmaceuticals Inc. | Aromatic heterocyclic compounds as anti-inflammatory agents |
| EP1158985B1 (en) | 1999-01-13 | 2011-12-28 | Bayer HealthCare LLC | OMEGA-CARBOXY ARYL SUBSTITUTED DIPHENYL UREAS AS p38 KINASE INHIBITORS |
| EP1140840B1 (en) | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
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| ATE278674T1 (de) | 1999-03-12 | 2004-10-15 | Boehringer Ingelheim Pharma | Heterocyklischer harnstoff und verwandte verbindungen als entzündungshemmende mittel |
| CA2374737C (en) | 1999-07-09 | 2008-02-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | Novel process for synthesis of heteroaryl-substituted urea compounds |
| EP1232150B1 (en) * | 1999-11-16 | 2007-10-10 | Boehringer Ingelheim Pharmaceuticals Inc. | Urea derivatives as anti-inflammatory agents |
| US6525046B1 (en) | 2000-01-18 | 2003-02-25 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds as antiinflammatory agents |
| US6492529B1 (en) | 2000-01-18 | 2002-12-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Bis pyrazole-1H-pyrazole intermediates and their synthesis |
| WO2002083628A1 (en) | 2001-04-13 | 2002-10-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1,4-disubstituted benzo-fused compounds |
| WO2002083642A1 (en) | 2001-04-13 | 2002-10-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as anti-inflammatory agents |
| JP2004530690A (ja) * | 2001-05-16 | 2004-10-07 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 抗炎症性薬剤として有用なジアリールウレア誘導体 |
| EP1395561A1 (en) | 2001-05-25 | 2004-03-10 | Boehringer Ingelheim Pharmaceuticals Inc. | Carbamate and oxamide compounds as inhibitors of cytokine production |
| WO2003005999A2 (en) | 2001-07-11 | 2003-01-23 | Boehringer Ingelheim Pharmaceuticals, Inc. | Methods of treating cytokine mediated diseases |
| SI1478358T1 (sl) | 2002-02-11 | 2013-09-30 | Bayer Healthcare Llc | Sorafenib tozilat za zdravljenje bolezni, značilnih po abnormalni angiogenezi |
| US20040023961A1 (en) | 2002-02-11 | 2004-02-05 | Bayer Corporation | Aryl ureas with raf kinase and angiogenisis inhibiting activity |
| EP1480973B1 (en) | 2002-02-25 | 2008-02-13 | Boehringer Ingelheim Pharmaceuticals Inc. | 1,4-disubstituted benzofused cycloalkyl urea compounds useful in treating cytokine mediated diseases |
| PE20040522A1 (es) | 2002-05-29 | 2004-09-28 | Novartis Ag | Derivados de diarilurea dependientes de la cinasa de proteina |
| EP1549621A1 (en) | 2002-08-08 | 2005-07-06 | Boehringer Ingelheim Pharmaceuticals Inc. | Fluorinated phenyl-naphthalenyl-urea compounds as inhibitors of cytokines involved in inflammatory processes |
| WO2004113352A1 (en) | 2003-06-19 | 2004-12-29 | Amedis Pharmaceuticals Ltd. | Silylated heterocyclylurea derivatives as cytokine-inhibitors |
| WO2005005396A1 (en) | 2003-06-30 | 2005-01-20 | Boehringer Ingelheim Pharmaceuticals, Inc. | Process of making di-aryl urea compounds |
| CA2536293A1 (en) | 2003-08-22 | 2005-03-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Methods of treating copd and pulmonary hypertension |
| WO2005023761A2 (en) | 2003-09-11 | 2005-03-17 | Kemia, Inc. | Cytokine inhibitors |
| WO2005044825A1 (en) | 2003-10-21 | 2005-05-19 | Amedis Pharmaceuticals Ltd. | Silicon compounds and their use |
| GB0327734D0 (en) * | 2003-11-28 | 2003-12-31 | Novartis Ag | Organic compounds |
| PE20051046A1 (es) | 2003-11-28 | 2006-01-11 | Novartis Ag | Derivados de diaril-urea en el tratamiento de enfermedades dependientes de la quinasa de proteina |
| CA2564355C (en) | 2004-05-07 | 2012-07-03 | Amgen Inc. | Protein kinase modulators and method of use |
| US20060035893A1 (en) | 2004-08-07 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders |
| GB0423554D0 (en) | 2004-10-22 | 2004-11-24 | Cancer Rec Tech Ltd | Therapeutic compounds |
| TW200740820A (en) | 2005-07-05 | 2007-11-01 | Takeda Pharmaceuticals Co | Fused heterocyclic derivatives and use thereof |
| PE20070795A1 (es) | 2005-10-28 | 2007-08-24 | Lilly Co Eli | Compuestos pirazol-urea-heterociclicos como inhibidores de cinasa |
| TW200804349A (en) | 2005-12-23 | 2008-01-16 | Kalypsys Inc | Novel substituted pyrimidinyloxy ureas as inhibitors of protein kinases |
| DE602007010038D1 (de) | 2006-12-22 | 2010-12-02 | Hoffmann La Roche | Pyrimidylderivate als proteinkinaseinhibitoren |
| 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 |
| JP5546823B2 (ja) | 2009-09-30 | 2014-07-09 | 小林製薬株式会社 | 薬剤付着用具セット |
| GB0921730D0 (en) | 2009-12-11 | 2010-01-27 | Respivert Ltd | Method of treatment |
| GB0921731D0 (en) | 2009-12-11 | 2010-01-27 | Respivert Ltd | Theraputic uses |
| GB201005589D0 (en) | 2010-04-01 | 2010-05-19 | Respivert Ltd | Novel compounds |
| US9024041B2 (en) | 2010-04-08 | 2015-05-05 | Respivert Ltd. | P38 MAP kinase inhibitors |
| 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 |
| GB201010196D0 (en) | 2010-06-17 | 2010-07-21 | Respivert Ltd | Methods |
| WO2011158044A2 (en) | 2010-06-17 | 2011-12-22 | Respivert Limited | Respiratory formulations and compounds for use therein |
| 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 |
| 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 |
| UA115320C2 (uk) | 2011-12-09 | 2017-10-25 | К'Єзі Фармачеутічі С.П.А. | Інгібітори кінази |
| GB201214750D0 (en) | 2012-08-17 | 2012-10-03 | Respivert Ltd | Compounds |
| US20150225373A1 (en) | 2012-08-29 | 2015-08-13 | Respivert Limited | Kinase inhibitors |
| EP2890460B1 (en) | 2012-08-29 | 2017-02-22 | Respivert Limited | Kinase inhibitors |
| US9783556B2 (en) | 2012-08-29 | 2017-10-10 | 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 |
| WO2014140582A1 (en) | 2013-03-14 | 2014-09-18 | Respivert Limited | Kinase inhibitors |
| EP2981534B1 (en) | 2013-04-02 | 2017-07-19 | Topivert Pharma Limited | Kinase inhibitors based upon n-alkyl pyrazoles |
| AU2014246866B2 (en) | 2013-04-02 | 2018-05-10 | Oxular Acquisitions Limited | Kinase inhibitor |
| 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 |
| EP3201189A1 (en) | 2014-10-01 | 2017-08-09 | Respivert Limited | N-phenyl-3-quinazolin-6-yl-benzamide derivatives as p38 kinase inhibitors |
-
2014
- 2014-12-19 CA CA2934199A patent/CA2934199A1/en not_active Abandoned
- 2014-12-19 WO PCT/GB2014/053781 patent/WO2015092423A1/en not_active Ceased
- 2014-12-19 CN CN201480069332.3A patent/CN106029651A/zh active Pending
- 2014-12-19 CN CN202111067810.5A patent/CN113717162A/zh active Pending
- 2014-12-19 AU AU2014369449A patent/AU2014369449B2/en not_active Ceased
- 2014-12-19 US US15/105,912 patent/US9890185B2/en not_active Expired - Fee Related
- 2014-12-19 JP JP2016541566A patent/JP6514703B2/ja not_active Expired - Fee Related
- 2014-12-19 EP EP14815839.7A patent/EP3083604A1/en not_active Withdrawn
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