JP2017535525A5 - - Google Patents
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- Publication number
- JP2017535525A5 JP2017535525A5 JP2017517316A JP2017517316A JP2017535525A5 JP 2017535525 A5 JP2017535525 A5 JP 2017535525A5 JP 2017517316 A JP2017517316 A JP 2017517316A JP 2017517316 A JP2017517316 A JP 2017517316A JP 2017535525 A5 JP2017535525 A5 JP 2017535525A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- phenyl
- amino
- tert
- butyl
- 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 99
- -1 Or H Chemical group 0.000 claims 71
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 60
- 125000005843 halogen group Chemical group 0.000 claims 50
- 150000001875 compounds Chemical class 0.000 claims 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 46
- 125000003545 alkoxy group Chemical group 0.000 claims 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 42
- 125000001424 substituent group Chemical group 0.000 claims 40
- 125000002947 alkylene group Chemical group 0.000 claims 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 31
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims 23
- 125000004043 oxo group Chemical group O=* 0.000 claims 17
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 15
- 125000000304 alkynyl group Chemical group 0.000 claims 14
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 238000006243 chemical reaction Methods 0.000 claims 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 9
- 239000012453 solvate Substances 0.000 claims 9
- 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 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 230000000155 isotopic effect Effects 0.000 claims 7
- 238000009472 formulation Methods 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 5
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 5
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 5
- 235000019260 propionic acid Nutrition 0.000 claims 5
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 239000012634 fragment Substances 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 208000027866 inflammatory disease Diseases 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
- 206010046851 Uveitis Diseases 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 239000004202 carbamide Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 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
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 2
- 206010013774 Dry eye Diseases 0.000 claims 2
- 208000001344 Macular Edema Diseases 0.000 claims 2
- 206010025415 Macular oedema Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 201000005667 central retinal vein occlusion Diseases 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 206010023332 keratitis Diseases 0.000 claims 2
- 201000010666 keratoconjunctivitis Diseases 0.000 claims 2
- 201000010230 macular retinal edema Diseases 0.000 claims 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 2
- 208000004644 retinal vein occlusion Diseases 0.000 claims 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 208000005494 xerophthalmia Diseases 0.000 claims 2
- ZOCFJMSMDAYMGP-UUWRZZSWSA-N (2R)-2-amino-3-[4-[[4-[[4-[4-[5-tert-butyl-N-carbamoyl-3-(methanesulfonamido)-2-methoxyanilino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]amino]phenyl]propanoic acid Chemical compound N[C@@H](C(=O)O)CC1=CC=C(C=C1)NC(C1=C(C=C(C=C1)NC1=NC=CC(=C1)OC1=CC=C(C2=CC=CC=C12)N(C(N)=O)C1=C(C(=CC(=C1)C(C)(C)C)NS(=O)(=O)C)OC)OC)=O ZOCFJMSMDAYMGP-UUWRZZSWSA-N 0.000 claims 1
- DWAGBOQUQKNUHT-MUUNZHRXSA-N (2R)-2-amino-3-[[4-[[4-[4-[5-tert-butyl-N-carbamoyl-3-(methanesulfonamido)-2-methoxyanilino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]amino]propanoic acid Chemical compound N[C@@H](C(=O)O)CNC(C1=C(C=C(C=C1)NC1=NC=CC(=C1)OC1=CC=C(C2=CC=CC=C12)N(C(N)=O)C1=C(C(=CC(=C1)C(C)(C)C)NS(=O)(=O)C)OC)OC)=O DWAGBOQUQKNUHT-MUUNZHRXSA-N 0.000 claims 1
- AOZXYQKAJCPDOO-GDLZYMKVSA-N (2R)-2-amino-4-[[4-[[4-[4-[5-tert-butyl-N-carbamoyl-3-(methanesulfonamido)-2-methoxyanilino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]amino]butanoic acid Chemical compound N[C@@H](C(=O)O)CCNC(C1=C(C=C(C=C1)NC1=NC=CC(=C1)OC1=CC=C(C2=CC=CC=C12)N(C(N)=O)C1=C(C(=CC(=C1)C(C)(C)C)NS(=O)(=O)C)OC)OC)=O AOZXYQKAJCPDOO-GDLZYMKVSA-N 0.000 claims 1
- LEMGLZFWAXQIGI-SSEXGKCCSA-N (2R)-2-amino-5-[[4-[[4-[4-[5-tert-butyl-N-carbamoyl-3-(methanesulfonamido)-2-methoxyanilino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]amino]pentanoic acid Chemical compound N[C@@H](C(=O)O)CCCNC(C1=C(C=C(C=C1)NC1=NC=CC(=C1)OC1=CC=C(C2=CC=CC=C12)N(C(N)=O)C1=C(C(=CC(=C1)C(C)(C)C)NS(=O)(=O)C)OC)OC)=O LEMGLZFWAXQIGI-SSEXGKCCSA-N 0.000 claims 1
- PQGBEXCOCSZOSC-WJOKGBTCSA-N (2R)-2-amino-6-[[4-[[4-[4-[5-tert-butyl-N-carbamoyl-3-(methanesulfonamido)-2-methoxyanilino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]amino]hexanoic acid Chemical compound N[C@@H](C(=O)O)CCCCNC(C1=C(C=C(C=C1)NC1=NC=CC(=C1)OC1=CC=C(C2=CC=CC=C12)N(C(N)=O)C1=C(C(=CC(=C1)C(C)(C)C)NS(=O)(=O)C)OC)OC)=O PQGBEXCOCSZOSC-WJOKGBTCSA-N 0.000 claims 1
- YBESOBZDUWRXFW-JGCGQSQUSA-N (2R)-2-amino-7-[[4-[[4-[4-[5-tert-butyl-N-carbamoyl-3-(methanesulfonamido)-2-methoxyanilino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]amino]heptanoic acid Chemical compound N[C@@H](C(=O)O)CCCCCNC(C1=C(C=C(C=C1)NC1=NC=CC(=C1)OC1=CC=C(C2=CC=CC=C12)N(C(N)=O)C1=C(C(=CC(=C1)C(C)(C)C)NS(=O)(=O)C)OC)OC)=O YBESOBZDUWRXFW-JGCGQSQUSA-N 0.000 claims 1
- AYJYLAXRYVTNJG-XIFFEERXSA-N (2S)-1-[4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]pyrrolidine-2-carboxylic acid 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)NC1=CC(=C(C(=O)N2[C@@H](CCC2)C(=O)O)C=C1)OC)=O)OC)NS(=O)(=O)C AYJYLAXRYVTNJG-XIFFEERXSA-N 0.000 claims 1
- ZOCFJMSMDAYMGP-UMSFTDKQSA-N (2S)-2-amino-3-[4-[[4-[[4-[4-[5-tert-butyl-N-carbamoyl-3-(methanesulfonamido)-2-methoxyanilino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]amino]phenyl]propanoic acid Chemical compound N[C@H](C(=O)O)CC1=CC=C(C=C1)NC(C1=C(C=C(C=C1)NC1=NC=CC(=C1)OC1=CC=C(C2=CC=CC=C12)N(C(N)=O)C1=C(C(=CC(=C1)C(C)(C)C)NS(=O)(=O)C)OC)OC)=O ZOCFJMSMDAYMGP-UMSFTDKQSA-N 0.000 claims 1
- DWAGBOQUQKNUHT-NDEPHWFRSA-N (2S)-2-amino-3-[[4-[[4-[4-[5-tert-butyl-N-carbamoyl-3-(methanesulfonamido)-2-methoxyanilino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]amino]propanoic acid Chemical compound N[C@H](C(=O)O)CNC(C1=C(C=C(C=C1)NC1=NC=CC(=C1)OC1=CC=C(C2=CC=CC=C12)N(C(N)=O)C1=C(C(=CC(=C1)C(C)(C)C)NS(=O)(=O)C)OC)OC)=O DWAGBOQUQKNUHT-NDEPHWFRSA-N 0.000 claims 1
- AOZXYQKAJCPDOO-LJAQVGFWSA-N (2S)-2-amino-4-[[4-[[4-[4-[5-tert-butyl-N-carbamoyl-3-(methanesulfonamido)-2-methoxyanilino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]amino]butanoic acid Chemical compound N[C@H](C(=O)O)CCNC(C1=C(C=C(C=C1)NC1=NC=CC(=C1)OC1=CC=C(C2=CC=CC=C12)N(C(N)=O)C1=C(C(=CC(=C1)C(C)(C)C)NS(=O)(=O)C)OC)OC)=O AOZXYQKAJCPDOO-LJAQVGFWSA-N 0.000 claims 1
- LEMGLZFWAXQIGI-PMERELPUSA-N (2S)-2-amino-5-[[4-[[4-[4-[5-tert-butyl-N-carbamoyl-3-(methanesulfonamido)-2-methoxyanilino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]amino]pentanoic acid Chemical compound N[C@H](C(=O)O)CCCNC(C1=C(C=C(C=C1)NC1=NC=CC(=C1)OC1=CC=C(C2=CC=CC=C12)N(C(N)=O)C1=C(C(=CC(=C1)C(C)(C)C)NS(=O)(=O)C)OC)OC)=O LEMGLZFWAXQIGI-PMERELPUSA-N 0.000 claims 1
- QPGCITMMYJSDJZ-BHVANESWSA-N (2S)-6-[[4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]amino]-2-(dimethylamino)hexanoic acid 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(=O)NCCCC[C@@H](C(=O)O)N(C)C)C=C1)OC)OC)NS(=O)(=O)C QPGCITMMYJSDJZ-BHVANESWSA-N 0.000 claims 1
- IJVWDCLNTNHFJJ-XIFFEERXSA-N (2S)-6-[[4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoyl]amino]-2-(methylamino)hexanoic acid 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(=O)NCCCC[C@@H](C(=O)O)NC)C=C1)OC)OC)NS(=O)(=O)C IJVWDCLNTNHFJJ-XIFFEERXSA-N 0.000 claims 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims 1
- VIKJWJNKFSMTEX-UHFFFAOYSA-N 1-[5-tert-butyl-2-methoxy-3-(sulfamoylmethyl)phenyl]-3-[4-[2-[4-[3-hydroxy-2,2-bis(hydroxymethyl)propyl]sulfonyl-3-methoxyanilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)CS(=O)(=O)N)OC)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=C(C=C1)S(=O)(=O)CC(CO)(CO)CO)OC VIKJWJNKFSMTEX-UHFFFAOYSA-N 0.000 claims 1
- MJISMUKSKIOBSE-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-(3-methoxy-4-methylsulfinylanilino)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)S(=O)C)OC)OC)NS(=O)(=O)C MJISMUKSKIOBSE-UHFFFAOYSA-N 0.000 claims 1
- HPGFYCRREHYBHF-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-(3-methoxy-4-methylsulfonylanilino)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)S(=O)(=O)C)OC)OC)NS(=O)(=O)C HPGFYCRREHYBHF-UHFFFAOYSA-N 0.000 claims 1
- XDRNEDQVVYUWQX-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-(3-methoxy-4-sulfamoylanilino)pyrimidin-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=NC(=NC=C1)NC1=CC(=C(C=C1)S(=O)(=O)N)OC)=O)OC)NS(=O)(=O)C XDRNEDQVVYUWQX-UHFFFAOYSA-N 0.000 claims 1
- AJJZMNCMJRGQGR-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-cyano-4-(2-morpholin-4-ylethoxy)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)OCCN1CCOCC1)C#N)OC)NS(=O)(=O)C AJJZMNCMJRGQGR-UHFFFAOYSA-N 0.000 claims 1
- IEIZPHDIRQTHFS-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-cyano-4-(3-morpholin-4-ylpropoxy)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)OCCCN1CCOCC1)C#N)OC)NS(=O)(=O)C IEIZPHDIRQTHFS-UHFFFAOYSA-N 0.000 claims 1
- BWLAJBHRTXMPDA-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-4-(2-morpholin-4-ylethylsulfonyl)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)S(=O)(=O)CCN1CCOCC1)OC)OC)NS(=O)(=O)C BWLAJBHRTXMPDA-UHFFFAOYSA-N 0.000 claims 1
- ZIQLKKLODNSOQM-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-4-(2-oxopyridin-1-yl)anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NS(=O)(=O)C)OC)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=C(C=C1)N1C(C=CC=C1)=O)OC ZIQLKKLODNSOQM-UHFFFAOYSA-N 0.000 claims 1
- GQEMZEYJTRONFH-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-4-[3-(4-methylpiperazin-1-yl)propylsulfonyl]anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C(C)(C)(C)C=1C=C(C(=C(C=1)NS(=O)(=O)C)OC)NC(=O)NC1=CC=C(C2=CC=CC=C12)OC1=CC(=NC=C1)NC1=CC(=C(C=C1)S(=O)(=O)CCCN1CCN(CC1)C)OC GQEMZEYJTRONFH-UHFFFAOYSA-N 0.000 claims 1
- YSSBYWFFOQLHDZ-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-4-[methyl(2-morpholin-4-ylethyl)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(=C(C=C1)S(N(CCN1CCOCC1)C)(=O)=O)OC)OC)NS(=O)(=O)C YSSBYWFFOQLHDZ-UHFFFAOYSA-N 0.000 claims 1
- VYVXFOXJTIGIHY-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-4-[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(=C(C=C1)S(N(CCCN1CCOCC1)C)(=O)=O)OC)OC)NS(=O)(=O)C VYVXFOXJTIGIHY-UHFFFAOYSA-N 0.000 claims 1
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- CNHBGMQLPQLUDC-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-hydroxybenzoic acid 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(=O)O)C=C1)O)OC)NS(=O)(=O)C CNHBGMQLPQLUDC-UHFFFAOYSA-N 0.000 claims 1
- PTMVPXQFPYJIMN-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-(1-methylpiperidin-4-yl)benzamide 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(=O)NC2CCN(CC2)C)C=C1)OC)OC)NS(=O)(=O)C PTMVPXQFPYJIMN-UHFFFAOYSA-N 0.000 claims 1
- RNSWIRKBAOEBLQ-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-(2-methyl-2-morpholin-4-ylpropyl)benzamide 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(=O)NCC(C)(N2CCOCC2)C)C=C1)OC)OC)NS(=O)(=O)C RNSWIRKBAOEBLQ-UHFFFAOYSA-N 0.000 claims 1
- LVONFGJJWNUDSA-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-(2-morpholin-4-yl-2-oxoethyl)benzamide 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(=O)NCC(=O)N2CCOCC2)C=C1)OC)OC)NS(=O)(=O)C LVONFGJJWNUDSA-UHFFFAOYSA-N 0.000 claims 1
- BPROBXOFSXWRJR-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-(2-morpholin-4-ylethyl)benzamide 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)NC1=CC(=C(C(=O)NCCN2CCOCC2)C=C1)OC)=O)OC)NS(=O)(=O)C BPROBXOFSXWRJR-UHFFFAOYSA-N 0.000 claims 1
- VWMYXPSMDHDIET-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-(2-piperazin-1-ylethyl)benzamide 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(=O)NCCN2CCNCC2)C=C1)OC)OC)NS(=O)(=O)C VWMYXPSMDHDIET-UHFFFAOYSA-N 0.000 claims 1
- SDIVAOWWTUDXMT-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-(2-piperidin-1-ylethyl)benzamide 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(=O)NCCN2CCCCC2)C=C1)OC)OC)NS(=O)(=O)C SDIVAOWWTUDXMT-UHFFFAOYSA-N 0.000 claims 1
- CCTCNNMOJWHFIA-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-(2-piperidin-4-ylethyl)benzamide 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)NC1=CC(=C(C(=O)NCCC2CCNCC2)C=C1)OC)=O)OC)NS(=O)(=O)C CCTCNNMOJWHFIA-UHFFFAOYSA-N 0.000 claims 1
- VAHNHSHKGOVRRS-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-(2-pyrrolidin-1-ylethyl)benzamide 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(=O)NCCN2CCCC2)C=C1)OC)OC)NS(=O)(=O)C VAHNHSHKGOVRRS-UHFFFAOYSA-N 0.000 claims 1
- XZONPFGSXMCDND-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-(2-thiomorpholin-4-ylethyl)benzamide 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(=O)NCCN2CCSCC2)C=C1)OC)OC)NS(=O)(=O)C XZONPFGSXMCDND-UHFFFAOYSA-N 0.000 claims 1
- HMBIOLBRLKAILX-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-(3-morpholin-4-ylpropyl)benzamide 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(=O)NCCCN2CCOCC2)C=C1)OC)OC)NS(=O)(=O)C HMBIOLBRLKAILX-UHFFFAOYSA-N 0.000 claims 1
- CSXDRRLHZJWOOX-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-(4-morpholin-4-ylbutyl)benzamide 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(=O)NCCCCN2CCOCC2)C=C1)OC)OC)NS(=O)(=O)C CSXDRRLHZJWOOX-UHFFFAOYSA-N 0.000 claims 1
- YBQBWKIOPABUPG-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[(1-methylpiperidin-4-yl)methyl]benzamide 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(=O)NCC2CCN(CC2)C)C=C1)OC)OC)NS(=O)(=O)C YBQBWKIOPABUPG-UHFFFAOYSA-N 0.000 claims 1
- ACJJZJPVAWLTQD-MUUNZHRXSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[(2R)-1-[2-(2-methoxyethoxy)ethoxy]propan-2-yl]benzamide 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(=O)N[C@@H](COCCOCCOC)C)C=C1)OC)OC)NS(=O)(=O)C ACJJZJPVAWLTQD-MUUNZHRXSA-N 0.000 claims 1
- ACJJZJPVAWLTQD-NDEPHWFRSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[(2S)-1-[2-(2-methoxyethoxy)ethoxy]propan-2-yl]benzamide 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(=O)N[C@H](COCCOCCOC)C)C=C1)OC)OC)NS(=O)(=O)C ACJJZJPVAWLTQD-NDEPHWFRSA-N 0.000 claims 1
- ZORBJIAADRKZOH-MHZLTWQESA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[(2S)-1-morpholin-4-ylpropan-2-yl]benzamide 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(=O)N[C@H](CN2CCOCC2)C)C=C1)OC)OC)NS(=O)(=O)C ZORBJIAADRKZOH-MHZLTWQESA-N 0.000 claims 1
- HJDQNNIRKWGQGL-JBQSSDAJSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzamide 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)NC1=CC(=C(C(=O)NC[C@@H]([C@@H]([C@@H](CO)O)O)O)C=C1)OC)=O)OC)NS(=O)(=O)C HJDQNNIRKWGQGL-JBQSSDAJSA-N 0.000 claims 1
- FCHGXFUOVXKORC-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[2-(1,4-oxazepan-4-yl)ethyl]benzamide 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(=O)NCCN2CCOCCC2)C=C1)OC)OC)NS(=O)(=O)C FCHGXFUOVXKORC-UHFFFAOYSA-N 0.000 claims 1
- FSRFRWLXYSIGBM-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[2-(1-methylpiperidin-4-yl)ethyl]benzamide 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(=O)NCCC2CCN(CC2)C)C=C1)OC)OC)NS(=O)(=O)C FSRFRWLXYSIGBM-UHFFFAOYSA-N 0.000 claims 1
- XGPWEWYVVPYSIL-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[2-(4-methyl-1,4-diazepan-1-yl)ethyl]benzamide 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(=O)NCCN2CCN(CCC2)C)C=C1)OC)OC)NS(=O)(=O)C XGPWEWYVVPYSIL-UHFFFAOYSA-N 0.000 claims 1
- OOJSOQNVMKPFMZ-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[2-(4-propan-2-ylpiperazin-1-yl)ethyl]benzamide 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)NC1=CC(=C(C(=O)NCCN2CCN(CC2)C(C)C)C=C1)OC)=O)OC)NS(=O)(=O)C OOJSOQNVMKPFMZ-UHFFFAOYSA-N 0.000 claims 1
- KDSZOXKIGJOWQA-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]benzamide 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)NC1=CC(=C(C(=O)NCCOCCOCCOC)C=C1)OC)=O)OC)NS(=O)(=O)C KDSZOXKIGJOWQA-UHFFFAOYSA-N 0.000 claims 1
- RPCKPOCOYDJRME-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[2-[2-methoxyethyl(methyl)amino]ethyl]benzamide 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(=O)NCCN(C)CCOC)C=C1)OC)OC)NS(=O)(=O)C RPCKPOCOYDJRME-UHFFFAOYSA-N 0.000 claims 1
- YXGPQZLIIOQQAZ-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[3-(1,4-oxazepan-4-yl)propyl]benzamide 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(=O)NCCCN2CCOCCC2)C=C1)OC)OC)NS(=O)(=O)C YXGPQZLIIOQQAZ-UHFFFAOYSA-N 0.000 claims 1
- JDAQJEHWJCXAFI-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-[3-(4-methylpiperazin-1-yl)propyl]benzamide 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(=O)NCCCN2CCN(CC2)C)C=C1)OC)OC)NS(=O)(=O)C JDAQJEHWJCXAFI-UHFFFAOYSA-N 0.000 claims 1
- NSDKCCVCMVMJRG-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-methyl-N-(2-morpholin-4-ylethyl)benzamide 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(=O)N(CCN2CCOCC2)C)C=C1)OC)OC)NS(=O)(=O)C NSDKCCVCMVMJRG-UHFFFAOYSA-N 0.000 claims 1
- IHCLBOWQUVPHBB-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-methyl-N-(3-morpholin-4-ylpropyl)benzamide 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(=O)N(CCCN2CCOCC2)C)C=C1)OC)OC)NS(=O)(=O)C IHCLBOWQUVPHBB-UHFFFAOYSA-N 0.000 claims 1
- IPRGOVMOQCIUFP-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxy-N-methyl-N-[3-(1-oxo-1,4-thiazinan-4-yl)propyl]benzamide Chemical compound COc1cc(Nc2cc(Oc3ccc(NC(=O)Nc4cc(cc(NS(C)(=O)=O)c4OC)C(C)(C)C)c4ccccc34)ccn2)ccc1C(=O)N(C)CCCN1CCS(=O)CC1 IPRGOVMOQCIUFP-UHFFFAOYSA-N 0.000 claims 1
- GSLXENOGEBTETR-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzenesulfinic acid 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)S(=O)O)OC)OC)NS(=O)(=O)C GSLXENOGEBTETR-UHFFFAOYSA-N 0.000 claims 1
- QFXFIEVXAUEHEV-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methoxybenzoic acid 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)NC1=CC(=C(C(=O)O)C=C1)OC)=O)OC)NS(=O)(=O)C QFXFIEVXAUEHEV-UHFFFAOYSA-N 0.000 claims 1
- WZYIHGAMAIMVCI-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methylsulfanylbenzoic acid 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(=O)O)C=C1)SC)OC)NS(=O)(=O)C WZYIHGAMAIMVCI-UHFFFAOYSA-N 0.000 claims 1
- MTYINUZPDJUOMY-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methylsulfinylbenzoic acid 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(=O)O)C=C1)S(=O)C)OC)NS(=O)(=O)C MTYINUZPDJUOMY-UHFFFAOYSA-N 0.000 claims 1
- PFQXOQZQISAOCR-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-2-methylsulfonylbenzoic acid 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(=O)O)C=C1)S(=O)(=O)C)OC)NS(=O)(=O)C PFQXOQZQISAOCR-UHFFFAOYSA-N 0.000 claims 1
- OMWLIGUYAXHRNW-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-(2-hydroxyethyl)-2-methoxybenzamide 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)NC1=CC(=C(C(=O)NCCO)C=C1)OC)=O)OC)NS(=O)(=O)C OMWLIGUYAXHRNW-UHFFFAOYSA-N 0.000 claims 1
- DQGNRAHSEYSADB-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-(2-morpholin-4-ylethyl)benzamide 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(=O)NCCN2CCOCC2)C=C1)OC)NS(=O)(=O)C DQGNRAHSEYSADB-UHFFFAOYSA-N 0.000 claims 1
- AEQLIHRFVYSWGR-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-methoxybenzamide 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)NC1=CC(=C(C(=O)NC(CO)(CO)CO)C=C1)OC)=O)OC)NS(=O)(=O)C AEQLIHRFVYSWGR-UHFFFAOYSA-N 0.000 claims 1
- HNQXGEIEMKYOPM-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-[2-(1,1-dioxo-1,4-thiazinan-4-yl)ethyl]-2-methoxybenzamide 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(=O)NCCN2CCS(CC2)(=O)=O)C=C1)OC)OC)NS(=O)(=O)C HNQXGEIEMKYOPM-UHFFFAOYSA-N 0.000 claims 1
- QZJSWFQYYYAROL-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-[2-(2-hydroxyethoxy)ethyl]-2-methoxybenzamide 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)NC1=CC(=C(C(=O)NCCOCCO)C=C1)OC)=O)OC)NS(=O)(=O)C QZJSWFQYYYAROL-UHFFFAOYSA-N 0.000 claims 1
- AXTJOSYSBHOKSD-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-[2-(3,3-dimethylmorpholin-4-yl)ethyl]-2-methoxybenzamide 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(=O)NCCN2C(COCC2)(C)C)C=C1)OC)OC)NS(=O)(=O)C AXTJOSYSBHOKSD-UHFFFAOYSA-N 0.000 claims 1
- UWFBOHBKNSNRKL-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-[2-(4,4-difluoropiperidin-1-yl)ethyl]-2-methoxybenzamide 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(=O)NCCN2CCC(CC2)(F)F)C=C1)OC)OC)NS(=O)(=O)C UWFBOHBKNSNRKL-UHFFFAOYSA-N 0.000 claims 1
- CTZGLAIDGKCQCG-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-[2-(4-ethylpiperazin-1-yl)ethyl]-2-methoxybenzamide 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)NC1=CC(=C(C(=O)NCCN2CCN(CC2)CC)C=C1)OC)=O)OC)NS(=O)(=O)C CTZGLAIDGKCQCG-UHFFFAOYSA-N 0.000 claims 1
- UKRQSOVKWNILEE-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-[2-(4-fluoropiperidin-1-yl)ethyl]-2-methoxybenzamide 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(=O)NCCN2CCC(CC2)F)C=C1)OC)OC)NS(=O)(=O)C UKRQSOVKWNILEE-UHFFFAOYSA-N 0.000 claims 1
- NRUYGXKCLKFQSF-UHFFFAOYSA-N 4-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-[2-(4-hydroxy-1-methylpiperidin-4-yl)ethyl]-2-methoxybenzamide Chemical compound COC1=C(C=CC(NC2=NC=CC(OC3=CC=C(NC(=O)NC4=C(OC)C(NS(C)(=O)=O)=CC(=C4)C(C)(C)C)C4=CC=CC=C34)=C2)=C1)C(=O)NCCC1(O)CCN(C)CC1 NRUYGXKCLKFQSF-UHFFFAOYSA-N 0.000 claims 1
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| GB201010196D0 (en) | 2010-06-17 | 2010-07-21 | Respivert Ltd | Methods |
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-
2015
- 2015-09-30 MA MA040774A patent/MA40774A/fr unknown
- 2015-09-30 MA MA040775A patent/MA40775A/fr unknown
- 2015-10-01 WO PCT/GB2015/052877 patent/WO2016051188A1/en not_active Ceased
- 2015-10-01 CN CN201580053462.2A patent/CN107001274A/zh active Pending
- 2015-10-01 EA EA201790658A patent/EA035478B1/ru not_active IP Right Cessation
- 2015-10-01 JP JP2017517315A patent/JP6662863B2/ja not_active Expired - Fee Related
- 2015-10-01 BR BR112017005531A patent/BR112017005531A2/pt not_active Application Discontinuation
- 2015-10-01 WO PCT/GB2015/052876 patent/WO2016051187A1/en not_active Ceased
- 2015-10-01 AU AU2015326543A patent/AU2015326543B2/en not_active Ceased
- 2015-10-01 KR KR1020177010961A patent/KR20170063783A/ko not_active Withdrawn
- 2015-10-01 US US14/872,807 patent/US9499486B2/en not_active Expired - Fee Related
- 2015-10-01 KR KR1020177011685A patent/KR20170057445A/ko not_active Ceased
- 2015-10-01 JP JP2017517316A patent/JP6608918B2/ja not_active Expired - Fee Related
- 2015-10-01 BR BR112017006073A patent/BR112017006073A2/pt not_active Application Discontinuation
- 2015-10-01 US US14/872,527 patent/US9751837B2/en not_active Expired - Fee Related
- 2015-10-01 CA CA2961870A patent/CA2961870A1/en active Pending
- 2015-10-01 AU AU2015326614A patent/AU2015326614B2/en not_active Ceased
- 2015-10-01 EA EA201790660A patent/EA032694B1/ru not_active IP Right Cessation
- 2015-10-01 EP EP15782017.6A patent/EP3201179A1/en not_active Withdrawn
- 2015-10-01 MX MX2017004129A patent/MX373658B/es active IP Right Grant
- 2015-10-01 EP EP15782018.4A patent/EP3201180A1/en not_active Withdrawn
- 2015-10-01 MX MX2017004128A patent/MX2017004128A/es unknown
- 2015-10-01 CN CN201580053439.3A patent/CN106999478A/zh active Pending
-
2016
- 2016-10-12 US US15/291,359 patent/US9822076B2/en not_active Expired - Fee Related
-
2017
- 2017-05-24 US US15/604,258 patent/US10125100B2/en active Active
-
2018
- 2018-07-13 US US16/035,502 patent/US10392346B2/en active Active
-
2019
- 2019-07-10 US US16/508,253 patent/US10941115B2/en not_active Expired - Fee Related
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