JP2015524837A5 - - Google Patents
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- JP2015524837A5 JP2015524837A5 JP2015527028A JP2015527028A JP2015524837A5 JP 2015524837 A5 JP2015524837 A5 JP 2015524837A5 JP 2015527028 A JP2015527028 A JP 2015527028A JP 2015527028 A JP2015527028 A JP 2015527028A JP 2015524837 A5 JP2015524837 A5 JP 2015524837A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- amino
- ureido
- oxy
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 36
- 150000001875 compounds Chemical class 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 18
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- 125000002947 alkylene group Chemical group 0.000 claims 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 6
- -1 2-morpholinoethyl Chemical group 0.000 claims 5
- 125000005275 alkylenearyl group Chemical group 0.000 claims 5
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- 201000005667 central retinal vein occlusion Diseases 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 4
- 208000004644 retinal vein occlusion Diseases 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 208000002691 Choroiditis Diseases 0.000 claims 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims 3
- 208000011231 Crohn disease Diseases 0.000 claims 3
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 3
- 206010013774 Dry eye Diseases 0.000 claims 3
- 206010022941 Iridocyclitis Diseases 0.000 claims 3
- 208000003971 Posterior uveitis Diseases 0.000 claims 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 3
- 206010046851 Uveitis Diseases 0.000 claims 3
- 201000004612 anterior uveitis Diseases 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 206010023332 keratitis Diseases 0.000 claims 3
- 201000010666 keratoconjunctivitis Diseases 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 201000007407 panuveitis Diseases 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- YARHUYMJLJCURZ-UHFFFAOYSA-N 3-methoxy-5-[[4-[4-[[2-(4-methylphenyl)-5-propan-2-ylpyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C=1C(C(=O)NCCN2CCOCC2)=CC(OC)=CC=1NC(N=1)=NC=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)C)=NN1C1=CC=C(C)C=C1 YARHUYMJLJCURZ-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims 2
- 208000002177 Cataract Diseases 0.000 claims 2
- 206010010741 Conjunctivitis Diseases 0.000 claims 2
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims 2
- 206010012688 Diabetic retinal oedema Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- 206010064212 Eosinophilic oesophagitis Diseases 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000001344 Macular Edema Diseases 0.000 claims 2
- 206010025415 Macular oedema Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 208000000208 Wet Macular Degeneration Diseases 0.000 claims 2
- 206010064930 age-related macular degeneration Diseases 0.000 claims 2
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 208000029771 childhood onset asthma Diseases 0.000 claims 2
- 208000007451 chronic bronchitis Diseases 0.000 claims 2
- 201000011190 diabetic macular edema Diseases 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 201000000708 eosinophilic esophagitis Diseases 0.000 claims 2
- 208000024908 graft versus host disease Diseases 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 2
- 230000000968 intestinal effect Effects 0.000 claims 2
- 208000002780 macular degeneration Diseases 0.000 claims 2
- 201000010230 macular retinal edema Diseases 0.000 claims 2
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000002980 postoperative effect Effects 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 206010039083 rhinitis Diseases 0.000 claims 2
- 201000000306 sarcoidosis Diseases 0.000 claims 2
- 201000009890 sinusitis Diseases 0.000 claims 2
- BOBQDWLSTCDSET-UHFFFAOYSA-N 1-[2-(4-methylphenyl)-5-propan-2-ylpyrazol-3-yl]-3-naphthalen-1-ylurea Chemical compound C(C)(C)C1=NN(C(=C1)NC(NC1=CC=CC2=CC=CC=C12)=O)C1=CC=C(C=C1)C BOBQDWLSTCDSET-UHFFFAOYSA-N 0.000 claims 1
- FGBHWWCXGQAKAZ-UHFFFAOYSA-N 1-[4-[2-[3-methoxy-5-(morpholine-4-carbonyl)anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]-3-[2-(4-methylphenyl)-5-propan-2-ylpyrazol-3-yl]urea Chemical compound C=1C(C(=O)N2CCOCC2)=CC(OC)=CC=1NC(N=1)=NC=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)C)=NN1C1=CC=C(C)C=C1 FGBHWWCXGQAKAZ-UHFFFAOYSA-N 0.000 claims 1
- BANXPZGDYGVXOC-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-[3-(morpholine-4-carbonyl)anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=C(C=CC=4)C(=O)N4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 BANXPZGDYGVXOC-UHFFFAOYSA-N 0.000 claims 1
- OJKGJLKJOICLKA-UHFFFAOYSA-N 2-methoxy-5-[[4-[4-[[2-(4-methylphenyl)-5-propan-2-ylpyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C1=C(C(=O)NCCN2CCOCC2)C(OC)=CC=C1NC(N=1)=NC=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)C)=NN1C1=CC=C(C)C=C1 OJKGJLKJOICLKA-UHFFFAOYSA-N 0.000 claims 1
- QMMSRYDOEGIITQ-UHFFFAOYSA-N 3-[[4-[2,3-dichloro-4-[[2-(4-methylphenyl)-5-propan-2-ylpyrazol-3-yl]carbamoylamino]phenoxy]pyrimidin-2-yl]amino]-5-ethynyl-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C=1C=C(C)C=CC=1N1N=C(C(C)C)C=C1NC(=O)NC(C(=C1Cl)Cl)=CC=C1OC(N=1)=CC=NC=1NC(C=1)=CC(C#C)=CC=1C(=O)NCCN1CCOCC1 QMMSRYDOEGIITQ-UHFFFAOYSA-N 0.000 claims 1
- XCGWAOXDKPENDE-UHFFFAOYSA-N 3-[[4-[2,3-dichloro-4-[[2-(4-methylphenyl)-5-propan-2-ylpyrazol-3-yl]carbamoylamino]phenoxy]pyrimidin-2-yl]amino]-5-ethynylbenzamide Chemical compound C=1C=C(C)C=CC=1N1N=C(C(C)C)C=C1NC(=O)NC(C(=C1Cl)Cl)=CC=C1OC(N=1)=CC=NC=1NC1=CC(C#C)=CC(C(N)=O)=C1 XCGWAOXDKPENDE-UHFFFAOYSA-N 0.000 claims 1
- BWZYTKHNTXQKBP-UHFFFAOYSA-N 3-[[4-[2,3-dichloro-4-[[2-(4-methylphenyl)-5-propan-2-ylpyrazol-3-yl]carbamoylamino]phenoxy]pyrimidin-2-yl]amino]-n-[2-(dimethylamino)ethyl]-5-ethynylbenzamide Chemical compound C=1C=C(C)C=CC=1N1N=C(C(C)C)C=C1NC(=O)NC(C(=C1Cl)Cl)=CC=C1OC(N=1)=CC=NC=1NC1=CC(C#C)=CC(C(=O)NCCN(C)C)=C1 BWZYTKHNTXQKBP-UHFFFAOYSA-N 0.000 claims 1
- PURPJUPEELMKNM-UHFFFAOYSA-N 3-[[4-[2,3-difluoro-4-[[2-(4-methylphenyl)-5-propan-2-ylpyrazol-3-yl]carbamoylamino]phenoxy]pyrimidin-2-yl]amino]-5-ethynyl-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C=1C=C(C)C=CC=1N1N=C(C(C)C)C=C1NC(=O)NC(C(=C1F)F)=CC=C1OC(N=1)=CC=NC=1NC(C=1)=CC(C#C)=CC=1C(=O)NCCN1CCOCC1 PURPJUPEELMKNM-UHFFFAOYSA-N 0.000 claims 1
- WLXUDQMWNQFZOR-UHFFFAOYSA-N 3-[[4-[4-[[2-(4-methoxyphenyl)-5-propan-2-ylpyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-5-methyl-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=C(C=C(C)C=4)C(=O)NCCN4CCOCC4)N=CC=3)=CC=2)=CC(C(C)C)=N1 WLXUDQMWNQFZOR-UHFFFAOYSA-N 0.000 claims 1
- UDVSRXQVDHWZAL-UHFFFAOYSA-N 3-[[4-[4-[[2-(4-methoxyphenyl)-5-propan-2-ylpyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=C(C=CC=4)C(=O)NCCN4CCOCC4)N=CC=3)=CC=2)=CC(C(C)C)=N1 UDVSRXQVDHWZAL-UHFFFAOYSA-N 0.000 claims 1
- CZNVSHUEQYXNKX-UHFFFAOYSA-N 3-[[4-[4-[[2-(4-methylphenyl)-5-propan-2-ylpyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n-(2-morpholin-4-ylethyl)-5-(trifluoromethyl)benzamide Chemical compound C=1C=C(C)C=CC=1N1N=C(C(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC(N=1)=CC=NC=1NC(C=C(C=1)C(F)(F)F)=CC=1C(=O)NCCN1CCOCC1 CZNVSHUEQYXNKX-UHFFFAOYSA-N 0.000 claims 1
- DQLUUNQMRQJPAL-UHFFFAOYSA-N 3-[[4-[4-[[2-(4-methylphenyl)-5-propan-2-ylpyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C=1C=C(C)C=CC=1N1N=C(C(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC(N=1)=CC=NC=1NC(C=1)=CC=CC=1C(=O)NCCN1CCOCC1 DQLUUNQMRQJPAL-UHFFFAOYSA-N 0.000 claims 1
- ZOBKJVAECISXJA-UHFFFAOYSA-N 3-[[4-[4-[[5-cyclopropyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-5-methoxy-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C=1C(C(=O)NCCN2CCOCC2)=CC(OC)=CC=1NC(N=1)=NC=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C2CC2)=NN1C1=CC=C(C)C=C1 ZOBKJVAECISXJA-UHFFFAOYSA-N 0.000 claims 1
- KKBSRZBNVASLTJ-UHFFFAOYSA-N 3-[[4-[4-[[5-ethyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-5-methoxy-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C=1C=C(C)C=CC=1N1N=C(CC)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC(N=1)=CC=NC=1NC(C=1)=CC(OC)=CC=1C(=O)NCCN1CCOCC1 KKBSRZBNVASLTJ-UHFFFAOYSA-N 0.000 claims 1
- RIGZTRRKOZWKPG-SANMLTNESA-N 3-[[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-5-ethynyl-n-[(2s)-1-methoxypropan-2-yl]benzamide Chemical compound C#CC1=CC(C(=O)N[C@@H](C)COC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4N(N=C(C=4)C(C)(C)C)C=4C=CC(OC)=CC=4)=CC=3)C=CN=2)=C1 RIGZTRRKOZWKPG-SANMLTNESA-N 0.000 claims 1
- HHONORFVXLXKEB-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-5-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=C(C=C(OC)C=4)C(N)=O)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 HHONORFVXLXKEB-UHFFFAOYSA-N 0.000 claims 1
- BEMAXRGCROABFF-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n-propylbenzamide Chemical compound CCCNC(=O)C1=CC=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4N(N=C(C=4)C(C)(C)C)C=4C=CC(OC)=CC=4)=CC=3)C=CN=2)=C1 BEMAXRGCROABFF-UHFFFAOYSA-N 0.000 claims 1
- VWGMFKBQYRNIIN-PMERELPUSA-N 3-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-5-ethynyl-n-[(2s)-1-morpholin-4-ylpropan-2-yl]benzamide Chemical compound C([C@H](C)NC(=O)C=1C=C(C=C(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4N(N=C(C=4)C(C)(C)C)C=4C=CC(C)=CC=4)=CC=3)C=CN=2)C=1)C#C)N1CCOCC1 VWGMFKBQYRNIIN-PMERELPUSA-N 0.000 claims 1
- URRPWKVYUYOQBW-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-5-methylbenzamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=C(C=C(C)C=4)C(N)=O)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 URRPWKVYUYOQBW-UHFFFAOYSA-N 0.000 claims 1
- XZCLCFIAUCVNJF-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4N(N=C(C=4)C(C)(C)C)C=4C=CC(C)=CC=4)=CC=3)C=CN=2)=C1 XZCLCFIAUCVNJF-UHFFFAOYSA-N 0.000 claims 1
- JTERLHICJVJIRK-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n-(2-hydroxyethyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCCO)C=C1NC1=NC=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=N1 JTERLHICJVJIRK-UHFFFAOYSA-N 0.000 claims 1
- LHYKFLNJIXCRLM-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n-(2-hydroxyethyl)-5-methoxybenzamide Chemical compound OCCNC(=O)C1=CC(OC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4N(N=C(C=4)C(C)(C)C)C=4C=CC(C)=CC=4)=CC=3)C=CN=2)=C1 LHYKFLNJIXCRLM-UHFFFAOYSA-N 0.000 claims 1
- OHZMBBAXCDRXLC-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n-[2-(dimethylamino)ethyl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCCN(C)C)C=C1NC1=NC=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=N1 OHZMBBAXCDRXLC-UHFFFAOYSA-N 0.000 claims 1
- OCGMYHIDTHTZSV-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n-[2-(dimethylamino)ethyl]-5-methoxybenzamide Chemical compound CN(C)CCNC(=O)C1=CC(OC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4N(N=C(C=4)C(C)(C)C)C=4C=CC(C)=CC=4)=CC=3)C=CN=2)=C1 OCGMYHIDTHTZSV-UHFFFAOYSA-N 0.000 claims 1
- GHRBLHUQTOTLMU-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4N(N=C(C=4)C(C)(C)C)C=4C=CC(C)=CC=4)=CC=3)C=CN=2)=C1 GHRBLHUQTOTLMU-UHFFFAOYSA-N 0.000 claims 1
- HOBGSWDBYMRRJR-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-(4-methylthiophen-2-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CSC(N2C(=CC(=N2)C(C)(C)C)NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=C(C=CC=4)C(=O)NCCN4CCOCC4)N=CC=3)=CC=2)=C1 HOBGSWDBYMRRJR-UHFFFAOYSA-N 0.000 claims 1
- GAJUUQYPFUJQCH-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-(6-methoxypyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-5-ethynyl-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C1=NC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=C(C=C(C=4)C#C)C(=O)NCCN4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 GAJUUQYPFUJQCH-UHFFFAOYSA-N 0.000 claims 1
- DTYGFXKVLYKJLW-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-(6-methoxypyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-5-methoxy-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C=1C(C(=O)NCCN2CCOCC2)=CC(OC)=CC=1NC(N=1)=NC=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(OC)N=C1 DTYGFXKVLYKJLW-UHFFFAOYSA-N 0.000 claims 1
- LMFUUSCWSNKGAY-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-2-[4-(dimethylamino)phenyl]pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-5-ethynyl-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C1=CC(N(C)C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=C(C=C(C=4)C#C)C(=O)NCCN4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 LMFUUSCWSNKGAY-UHFFFAOYSA-N 0.000 claims 1
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| US20060036220A1 (en) * | 2003-01-22 | 2006-02-16 | Kohji Kawahara | Percutaneous absorption preparation for treating ophthalmic disease, use thereof and method for migration of ophthalmic remedy into topical tissue in eye |
| AU2008337286B2 (en) | 2007-12-19 | 2014-08-07 | Cancer Research Technology Limited | Pyrido[2,3-b]pyrazine-8-substituted compounds and their use |
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2012
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- 2013-08-16 BR BR112015003218A patent/BR112015003218A2/pt not_active IP Right Cessation
- 2013-08-16 CN CN201380054166.5A patent/CN105073725A/zh active Pending
- 2013-08-16 US US14/422,158 patent/US9701670B2/en not_active Expired - Fee Related
- 2013-08-16 WO PCT/GB2013/052184 patent/WO2014027209A1/en not_active Ceased
- 2013-08-16 CA CA2881914A patent/CA2881914A1/en not_active Abandoned
- 2013-08-16 MX MX2015002044A patent/MX2015002044A/es unknown
- 2013-08-16 AU AU2013303922A patent/AU2013303922A1/en not_active Abandoned
- 2013-08-16 EA EA201590391A patent/EA025393B1/ru not_active IP Right Cessation
- 2013-08-16 KR KR1020157006554A patent/KR20150056777A/ko not_active Withdrawn
- 2013-08-16 US US13/969,328 patent/US20140057915A1/en not_active Abandoned
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