AU2010289353B2 - Compounds as tyrosine kinase modulators - Google Patents
Compounds as tyrosine kinase modulators Download PDFInfo
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- AU2010289353B2 AU2010289353B2 AU2010289353A AU2010289353A AU2010289353B2 AU 2010289353 B2 AU2010289353 B2 AU 2010289353B2 AU 2010289353 A AU2010289353 A AU 2010289353A AU 2010289353 A AU2010289353 A AU 2010289353A AU 2010289353 B2 AU2010289353 B2 AU 2010289353B2
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- Australia
- Prior art keywords
- amino
- carbonyl
- pyridin
- phenoxy
- fluoro
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 111
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 title abstract description 20
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 title abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 150
- 239000000203 mixture Substances 0.000 claims description 139
- 238000000034 method Methods 0.000 claims description 111
- 229910052739 hydrogen Inorganic materials 0.000 claims description 110
- 239000001257 hydrogen Substances 0.000 claims description 110
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 103
- 150000002431 hydrogen Chemical group 0.000 claims description 100
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 97
- -1 Ci-C8 alkyl Chemical group 0.000 claims description 91
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 84
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 81
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 77
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 72
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 59
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 40
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 40
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000001475 halogen functional group Chemical group 0.000 claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 208000002780 macular degeneration Diseases 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical group 0.000 claims description 17
- 125000004104 aryloxy group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 239000004202 carbamide Substances 0.000 claims description 15
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 15
- 206010029113 Neovascularisation Diseases 0.000 claims description 14
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 14
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 14
- 208000004644 retinal vein occlusion Diseases 0.000 claims description 14
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 208000005590 Choroidal Neovascularization Diseases 0.000 claims description 11
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- 230000004770 neurodegeneration Effects 0.000 claims description 11
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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 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 9
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 9
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 9
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 208000026278 immune system disease Diseases 0.000 claims description 9
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 9
- 201000004681 Psoriasis Diseases 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 8
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 230000029663 wound healing Effects 0.000 claims description 8
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- 206010006187 Breast cancer Diseases 0.000 claims description 7
- 208000026310 Breast neoplasm Diseases 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 7
- 206010009944 Colon cancer Diseases 0.000 claims description 7
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 7
- 206010058202 Cystoid macular oedema Diseases 0.000 claims description 7
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- 208000010412 Glaucoma Diseases 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 7
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 7
- 208000001344 Macular Edema Diseases 0.000 claims description 7
- 201000010183 Papilledema Diseases 0.000 claims description 7
- 206010038389 Renal cancer Diseases 0.000 claims description 7
- 206010038886 Retinal oedema Diseases 0.000 claims description 7
- 230000033115 angiogenesis Effects 0.000 claims description 7
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- 208000019425 cirrhosis of liver Diseases 0.000 claims description 7
- 201000010206 cystoid macular edema Diseases 0.000 claims description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
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- 208000024519 eye neoplasm Diseases 0.000 claims description 7
- 230000002489 hematologic effect Effects 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
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- 201000005202 lung cancer Diseases 0.000 claims description 7
- 208000020816 lung neoplasm Diseases 0.000 claims description 7
- ZVSMCBXMMPTXPB-UHFFFAOYSA-N methyl 5-[4-[3-[(3-methylfuran-2-carbonyl)amino]anilino]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C1=CNC(C=2N=CC=C(NC=3C=C(NC(=O)C4=C(C=CO4)C)C=CC=3)C=2)=C1 ZVSMCBXMMPTXPB-UHFFFAOYSA-N 0.000 claims description 7
- 201000008106 ocular cancer Diseases 0.000 claims description 7
- 208000037803 restenosis Diseases 0.000 claims description 7
- 201000011195 retinal edema Diseases 0.000 claims description 7
- 208000032253 retinal ischemia Diseases 0.000 claims description 7
- IYDSQQHYVCHBKZ-UHFFFAOYSA-N 5-[4-[3-[(2-fluoro-5-methylphenyl)carbamoyl]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylic acid Chemical compound CC1=CC=C(F)C(NC(=O)C=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(O)=O)C=CC=2)=C1 IYDSQQHYVCHBKZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 claims description 5
- UYGRGONQGJGYDY-UHFFFAOYSA-N 2-fluoropiperidine Chemical compound FC1CCCCN1 UYGRGONQGJGYDY-UHFFFAOYSA-N 0.000 claims description 5
- OQDXZZHGQBFAKM-UHFFFAOYSA-N 2-fluoropyrrolidine Chemical compound FC1CCCN1 OQDXZZHGQBFAKM-UHFFFAOYSA-N 0.000 claims description 5
- NMDGZSOTLLTSKB-UHFFFAOYSA-N 3-methyl-n-[4-[2-(1h-pyrrol-2-yl)pyridin-4-yl]oxyphenyl]furan-2-carboxamide Chemical compound C1=COC(C(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=CC=3)=CC=2)=C1C NMDGZSOTLLTSKB-UHFFFAOYSA-N 0.000 claims description 5
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- LOASYNCSCBFHTC-UHFFFAOYSA-N 5-[4-[3-[(3-methylfuran-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylic acid Chemical compound C1=COC(C(=O)NC=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(O)=O)C=CC=2)=C1C LOASYNCSCBFHTC-UHFFFAOYSA-N 0.000 claims description 5
- BDTDDTOUVUTYCH-UHFFFAOYSA-N 5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylic acid Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(O)=O)=CC=2)=C1 BDTDDTOUVUTYCH-UHFFFAOYSA-N 0.000 claims description 5
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 5
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- NKTLRPAMUNWXJM-UHFFFAOYSA-N methyl 5-[4-[3-[(2-fluoro-5-methylphenyl)carbamoyl]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C1=CNC(C=2N=CC=C(OC=3C=C(C=CC=3)C(=O)NC=3C(=CC=C(C)C=3)F)C=2)=C1 NKTLRPAMUNWXJM-UHFFFAOYSA-N 0.000 claims description 5
- UONKVPSAMIUNOO-UHFFFAOYSA-N methyl 5-[4-[3-[(3-methylfuran-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C1=CNC(C=2N=CC=C(OC=3C=C(NC(=O)C4=C(C=CO4)C)C=CC=3)C=2)=C1 UONKVPSAMIUNOO-UHFFFAOYSA-N 0.000 claims description 5
- CBWFTSSODXUPJM-UHFFFAOYSA-N methyl 5-[4-[4-fluoro-3-[(3-methylfuran-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C1=CNC(C=2N=CC=C(OC=3C=C(NC(=O)C4=C(C=CO4)C)C(F)=CC=3)C=2)=C1 CBWFTSSODXUPJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 5
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 5
- HAFZJKPULUETJM-UHFFFAOYSA-N 2,3-dihydroxypropyl 5-[4-[3-[(3-methylfuran-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound C1=COC(C(=O)NC=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)OCC(O)CO)C=CC=2)=C1C HAFZJKPULUETJM-UHFFFAOYSA-N 0.000 claims description 4
- PZDHDXJQAMOBKZ-UHFFFAOYSA-N 2-hydroxyethyl 5-[4-[3-[(3-methylfuran-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound C1=COC(C(=O)NC=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)OCCO)C=CC=2)=C1C PZDHDXJQAMOBKZ-UHFFFAOYSA-N 0.000 claims description 4
- VLJVJTAAVYMOSM-UHFFFAOYSA-N 4-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-2-carboxylic acid Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3C=C(NC=3)C(O)=O)=CC=2)=C1 VLJVJTAAVYMOSM-UHFFFAOYSA-N 0.000 claims description 4
- NXUSKSUIDVFHMV-UHFFFAOYSA-N 5-[4-[3-[(3-methylfuran-2-carbonyl)amino]anilino]pyridin-2-yl]-1h-pyrrole-3-carboxylic acid Chemical compound C1=COC(C(=O)NC=2C=C(NC=3C=C(N=CC=3)C=3NC=C(C=3)C(O)=O)C=CC=2)=C1C NXUSKSUIDVFHMV-UHFFFAOYSA-N 0.000 claims description 4
- BNQPYLKCEUFMIL-UHFFFAOYSA-N 5-[4-[3-[(3-methylphenyl)carbamoyl]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylic acid Chemical compound CC1=CC=CC(NC(=O)C=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(O)=O)C=CC=2)=C1 BNQPYLKCEUFMIL-UHFFFAOYSA-N 0.000 claims description 4
- ZMSJBZUCLZSJBD-UHFFFAOYSA-N 5-[4-[3-[(3-methylthiophene-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylic acid Chemical compound C1=CSC(C(=O)NC=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(O)=O)C=CC=2)=C1C ZMSJBZUCLZSJBD-UHFFFAOYSA-N 0.000 claims description 4
- KDBPYQOSBQXORE-MHZLTWQESA-N 5-o-tert-butyl 1-o-methyl (2s)-2-[[5-[4-[3-fluoro-4-[(3-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carbonyl]amino]pentanedioate Chemical compound CC(C)(C)OC(=O)CC[C@@H](C(=O)OC)NC(=O)C1=CNC(C=2N=CC=C(OC=3C=C(F)C(NC(=O)NC=4C=C(C)C=CC=4)=CC=3)C=2)=C1 KDBPYQOSBQXORE-MHZLTWQESA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-L glutarate(2-) Chemical compound [O-]C(=O)CCCC([O-])=O JFCQEDHGNNZCLN-UHFFFAOYSA-L 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- XZQJQYSDFRPEAO-UHFFFAOYSA-N methyl 4-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-2-carboxylate Chemical compound N1C(C(=O)OC)=CC(C=2N=CC=C(OC=3C=CC(NC(=O)NC=4C(=CC=C(C)C=4)F)=CC=3)C=2)=C1 XZQJQYSDFRPEAO-UHFFFAOYSA-N 0.000 claims description 4
- LCQAKDPWORVUFI-UHFFFAOYSA-N methyl 5-[4-[3-[(3-methylphenyl)carbamoyl]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C1=CNC(C=2N=CC=C(OC=3C=C(C=CC=3)C(=O)NC=3C=C(C)C=CC=3)C=2)=C1 LCQAKDPWORVUFI-UHFFFAOYSA-N 0.000 claims description 4
- AMXSBDZACGANLM-UHFFFAOYSA-N methyl 5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C1=CNC(C=2N=CC=C(OC=3C=CC(NC(=O)NC=4C(=CC=C(C)C=4)F)=CC=3)C=2)=C1 AMXSBDZACGANLM-UHFFFAOYSA-N 0.000 claims description 4
- SFZCLRIMYNSHKV-UHFFFAOYSA-N n-(2,3-dihydroxypropyl)-5-[4-[3-[(3-methylfuran-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxamide Chemical compound C1=COC(C(=O)NC=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NCC(O)CO)C=CC=2)=C1C SFZCLRIMYNSHKV-UHFFFAOYSA-N 0.000 claims description 4
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- NFWAVSQGBXCTHM-HXUWFJFHSA-N 1-(2-fluoro-5-methylphenyl)-3-[4-[2-[4-[(3r)-3-hydroxypyrrolidine-1-carbonyl]-1h-pyrrol-2-yl]pyridin-4-yl]oxyphenyl]urea Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)N3C[C@H](O)CC3)=CC=2)=C1 NFWAVSQGBXCTHM-HXUWFJFHSA-N 0.000 claims description 3
- ZDWXFWNFQRHKKX-UHFFFAOYSA-N 2-hydroxyethyl 5-[4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound OCCOC(=O)C1=CNC(C=2N=CC=C(OC=3C=CC(NC(=O)NC=4C=C(C(Cl)=CC=4)C(F)(F)F)=CC=3)C=2)=C1 ZDWXFWNFQRHKKX-UHFFFAOYSA-N 0.000 claims description 3
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- GPEMPWCWCBURCR-UHFFFAOYSA-N 4-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-n-methyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)NC)=CC(C=2N=CC=C(OC=3C=CC(NC(=O)NC=4C(=CC=C(C)C=4)F)=CC=3)C=2)=C1 GPEMPWCWCBURCR-UHFFFAOYSA-N 0.000 claims description 3
- CDVOVVMOSZWTNG-UHFFFAOYSA-N 4-[s-methyl-n-[5-[4-[4-[(3-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carbonyl]sulfonimidoyl]butanoic acid Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)N=S(C)(=O)CCCC(O)=O)=CC=2)=C1 CDVOVVMOSZWTNG-UHFFFAOYSA-N 0.000 claims description 3
- KUYVWUAGELSGSE-UHFFFAOYSA-N 5-[4-[3-[(2-fluoro-5-methylphenyl)carbamoyl]phenoxy]pyridin-2-yl]-n-hydroxy-1h-pyrrole-3-carboxamide Chemical compound CC1=CC=C(F)C(NC(=O)C=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NO)C=CC=2)=C1 KUYVWUAGELSGSE-UHFFFAOYSA-N 0.000 claims description 3
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- RQTUJEVHUXNSJU-UHFFFAOYSA-N 5-[4-[3-fluoro-4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylic acid Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C(=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(O)=O)=CC=2)F)=C1 RQTUJEVHUXNSJU-UHFFFAOYSA-N 0.000 claims description 3
- COYINHYXPZWRFV-UHFFFAOYSA-N 5-[4-[3-fluoro-4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-n-hydroxy-1h-pyrrole-3-carboxamide Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C(=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NO)=CC=2)F)=C1 COYINHYXPZWRFV-UHFFFAOYSA-N 0.000 claims description 3
- STWRTVHIAAFEFU-UHFFFAOYSA-N 5-[4-[4-fluoro-3-[(3-methylfuran-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylic acid Chemical compound C1=COC(C(=O)NC=2C(=CC=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(O)=O)C=2)F)=C1C STWRTVHIAAFEFU-UHFFFAOYSA-N 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 239000006196 drop Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 239000000499 gel Substances 0.000 claims description 3
- 239000007943 implant Substances 0.000 claims description 3
- CPHLNZWLTXURLV-UHFFFAOYSA-N methyl 2-[[5-[4-[2-fluoro-5-[(2-fluoro-5-methylphenyl)carbamoyl]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carbonyl]amino]acetate Chemical compound COC(=O)CNC(=O)C1=CNC(C=2N=CC=C(OC=3C(=CC=C(C=3)C(=O)NC=3C(=CC=C(C)C=3)F)F)C=2)=C1 CPHLNZWLTXURLV-UHFFFAOYSA-N 0.000 claims description 3
- FADJGHQDAILALR-UHFFFAOYSA-N methyl 4-[4-[3-[(3-methylfuran-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-2-carboxylate Chemical compound N1C(C(=O)OC)=CC(C=2N=CC=C(OC=3C=C(NC(=O)C4=C(C=CO4)C)C=CC=3)C=2)=C1 FADJGHQDAILALR-UHFFFAOYSA-N 0.000 claims description 3
- SDTGPMXXWXOVJB-UHFFFAOYSA-N methyl 5-[4-[3-[(3-methylthiophene-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C1=CNC(C=2N=CC=C(OC=3C=C(NC(=O)C4=C(C=CS4)C)C=CC=3)C=2)=C1 SDTGPMXXWXOVJB-UHFFFAOYSA-N 0.000 claims description 3
- ATGRYYMJIAYDSA-UHFFFAOYSA-N methyl 5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenyl]sulfanylpyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C1=CNC(C=2N=CC=C(SC=3C=CC(NC(=O)NC=4C(=CC=C(C)C=4)F)=CC=3)C=2)=C1 ATGRYYMJIAYDSA-UHFFFAOYSA-N 0.000 claims description 3
- FARCUXOVRVSRLQ-UHFFFAOYSA-N n-(2-fluoro-5-methylphenyl)-3-[2-[4-(3-hydroxypyrrolidine-1-carbonyl)-1h-pyrrol-2-yl]pyridin-4-yl]oxybenzamide Chemical compound CC1=CC=C(F)C(NC(=O)C=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)N3CC(O)CC3)C=CC=2)=C1 FARCUXOVRVSRLQ-UHFFFAOYSA-N 0.000 claims description 3
- IBHVLWYGIJLFTH-LJQANCHMSA-N n-[3-[2-[4-[(3r)-3-hydroxypyrrolidine-1-carbonyl]-1h-pyrrol-2-yl]pyridin-4-yl]oxyphenyl]-3-methylfuran-2-carboxamide Chemical compound C1=COC(C(=O)NC=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)N3C[C@H](O)CC3)C=CC=2)=C1C IBHVLWYGIJLFTH-LJQANCHMSA-N 0.000 claims description 3
- IBHVLWYGIJLFTH-IBGZPJMESA-N n-[3-[2-[4-[(3s)-3-hydroxypyrrolidine-1-carbonyl]-1h-pyrrol-2-yl]pyridin-4-yl]oxyphenyl]-3-methylfuran-2-carboxamide Chemical compound C1=COC(C(=O)NC=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)N3C[C@@H](O)CC3)C=CC=2)=C1C IBHVLWYGIJLFTH-IBGZPJMESA-N 0.000 claims description 3
- NEJUEWNKNYUPHN-UHFFFAOYSA-N n-hydroxy-5-[4-[3-[(3-methylfuran-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxamide Chemical compound C1=COC(C(=O)NC=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NO)C=CC=2)=C1C NEJUEWNKNYUPHN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- NWPTXSZKCKXBNX-UHFFFAOYSA-N 1-(2-fluoro-5-methylphenyl)-3-[4-[2-(1h-pyrrol-2-yl)pyridin-4-yl]oxyphenyl]urea Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=CC=3)=CC=2)=C1 NWPTXSZKCKXBNX-UHFFFAOYSA-N 0.000 claims description 2
- VXDJEEXCCGWNJZ-UHFFFAOYSA-N 1-[2-fluoro-4-[2-[4-(3-hydroxypiperidine-1-carbonyl)-1h-pyrrol-2-yl]pyridin-4-yl]oxyphenyl]-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2C(=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)N3CC(O)CCC3)=CC=2)F)=C1 VXDJEEXCCGWNJZ-UHFFFAOYSA-N 0.000 claims description 2
- NATCVTPFVHNWNK-UHFFFAOYSA-N 1-[4-[2-[4-(azetidine-1-carbonyl)-1h-pyrrol-2-yl]pyridin-4-yl]oxyphenyl]-3-(2-fluoro-5-methylphenyl)urea Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)N3CCC3)=CC=2)=C1 NATCVTPFVHNWNK-UHFFFAOYSA-N 0.000 claims description 2
- ZBUMGFFYJJLQLI-UHFFFAOYSA-N 1-[4-[2-amino-6-(1h-pyrrol-2-yl)pyridin-4-yl]oxyphenyl]-3-(2-fluoro-5-methylphenyl)urea Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=C(N)C=3)C=3NC=CC=3)=CC=2)=C1 ZBUMGFFYJJLQLI-UHFFFAOYSA-N 0.000 claims description 2
- GNOLTAIPEDJTSV-UHFFFAOYSA-N 1-[5-[4-[3-fluoro-4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carbonyl]pyrrolidine-3-carboxylic acid Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C(=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)N3CC(CC3)C(O)=O)=CC=2)F)=C1 GNOLTAIPEDJTSV-UHFFFAOYSA-N 0.000 claims description 2
- HOGCJPPMBAIRFC-UHFFFAOYSA-N 1-[5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carbonyl]pyrrolidine-3-carboxylic acid Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)N3CC(CC3)C(O)=O)=CC=2)=C1 HOGCJPPMBAIRFC-UHFFFAOYSA-N 0.000 claims description 2
- CHXDAMYYTDOXGJ-UHFFFAOYSA-N 1-o-tert-butyl 2-o-methyl 4-[6-amino-4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]pyrrole-1,2-dicarboxylate Chemical compound CC(C)(C)OC(=O)N1C(C(=O)OC)=CC(C=2N=C(N)C=C(OC=3C=CC(NC(=O)NC=4C(=CC=C(C)C=4)F)=CC=3)C=2)=C1 CHXDAMYYTDOXGJ-UHFFFAOYSA-N 0.000 claims description 2
- SHDKGZPSIAIFTD-UHFFFAOYSA-N 2-[[4-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]thiophene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3C=C(SC=3)C(=O)NCC(O)=O)=CC=2)=C1 SHDKGZPSIAIFTD-UHFFFAOYSA-N 0.000 claims description 2
- BHOKICBHDXFHEH-UHFFFAOYSA-N 2-[[5-[4-[3-fluoro-4-[(3-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carbonyl]amino]acetic acid Chemical compound CC1=CC=CC(NC(=O)NC=2C(=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NCC(O)=O)=CC=2)F)=C1 BHOKICBHDXFHEH-UHFFFAOYSA-N 0.000 claims description 2
- UQBDOYHNSMFRPN-UHFFFAOYSA-N 2-hydroxyethyl 5-[4-[3-[(3-methylthiophene-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound C1=CSC(C(=O)NC=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)OCCO)C=CC=2)=C1C UQBDOYHNSMFRPN-UHFFFAOYSA-N 0.000 claims description 2
- LDZCJDGPCDLDBR-UHFFFAOYSA-N 2-methoxyethyl 5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound COCCOC(=O)C1=CNC(C=2N=CC=C(OC=3C=CC(NC(=O)NC=4C(=CC=C(C)C=4)F)=CC=3)C=2)=C1 LDZCJDGPCDLDBR-UHFFFAOYSA-N 0.000 claims description 2
- RFGSSZOLBKALKW-UHFFFAOYSA-N 3-[[5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carbonyl]amino]propanoic acid Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NCCC(O)=O)=CC=2)=C1 RFGSSZOLBKALKW-UHFFFAOYSA-N 0.000 claims description 2
- PZDZHZATHQOKCG-UHFFFAOYSA-N 4-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-n,n-dimethyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)N(C)C)=CC(C=2N=CC=C(OC=3C=CC(NC(=O)NC=4C(=CC=C(C)C=4)F)=CC=3)C=2)=C1 PZDZHZATHQOKCG-UHFFFAOYSA-N 0.000 claims description 2
- CJHIKUXWIQORDE-UHFFFAOYSA-N 4-[[5-[4-[3-fluoro-4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carbonyl]amino]butanoic acid Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C(=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NCCCC(O)=O)=CC=2)F)=C1 CJHIKUXWIQORDE-UHFFFAOYSA-N 0.000 claims description 2
- LNTWWMOOPMLARL-UHFFFAOYSA-N 4-[[5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carbonyl]amino]butanoic acid Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NCCCC(O)=O)=CC=2)=C1 LNTWWMOOPMLARL-UHFFFAOYSA-N 0.000 claims description 2
- QCDCLZAHLBMSPB-UHFFFAOYSA-N 4-fluoro-n-(2-fluoro-5-methylphenyl)-3-[2-[4-(3-hydroxypiperidine-1-carbonyl)-1h-pyrrol-2-yl]pyridin-4-yl]oxybenzamide Chemical compound CC1=CC=C(F)C(NC(=O)C=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)N3CC(O)CCC3)C(F)=CC=2)=C1 QCDCLZAHLBMSPB-UHFFFAOYSA-N 0.000 claims description 2
- OZDSCFUWIKCNMS-UHFFFAOYSA-N 5-[4-[2-fluoro-4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylic acid Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=C(F)C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(O)=O)=CC=2)=C1 OZDSCFUWIKCNMS-UHFFFAOYSA-N 0.000 claims description 2
- AWKDINURSDINTB-UHFFFAOYSA-N 5-[4-[2-fluoro-5-[(2-fluoro-5-methylphenyl)carbamoyl]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylic acid Chemical compound CC1=CC=C(F)C(NC(=O)C=2C=C(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(O)=O)C(F)=CC=2)=C1 AWKDINURSDINTB-UHFFFAOYSA-N 0.000 claims description 2
- ZIWJUDIEIITPBX-UHFFFAOYSA-N 5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxamide Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(N)=O)=CC=2)=C1 ZIWJUDIEIITPBX-UHFFFAOYSA-N 0.000 claims description 2
- IHGRRQDGJVUJSZ-UHFFFAOYSA-N 5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-n-(3-hydroxypropyl)-1h-pyrrole-3-carboxamide Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NCCCO)=CC=2)=C1 IHGRRQDGJVUJSZ-UHFFFAOYSA-N 0.000 claims description 2
- URFHWIMCQUTTHF-UHFFFAOYSA-N 5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-n-(3-morpholin-4-ylpropyl)-1h-pyrrole-3-carboxamide Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NCCCN3CCOCC3)=CC=2)=C1 URFHWIMCQUTTHF-UHFFFAOYSA-N 0.000 claims description 2
- ALTMKUMFQMSEFD-UHFFFAOYSA-N 5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-n-[4-(hydroxyamino)-4-oxobutyl]-1h-pyrrole-3-carboxamide Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NCCCC(=O)NO)=CC=2)=C1 ALTMKUMFQMSEFD-UHFFFAOYSA-N 0.000 claims description 2
- JYJKNIHQZXCKPB-UHFFFAOYSA-N 5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-n-hydroxy-1h-pyrrole-3-carboxamide Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NO)=CC=2)=C1 JYJKNIHQZXCKPB-UHFFFAOYSA-N 0.000 claims description 2
- DLBILCXJYLWFEI-UHFFFAOYSA-N 5-[4-[4-[(3-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(N)=O)=CC=2)=C1 DLBILCXJYLWFEI-UHFFFAOYSA-N 0.000 claims description 2
- QLJWNTHEJPFKDE-UHFFFAOYSA-N 5-[4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylic acid Chemical compound OC(=O)C1=CNC(C=2N=CC=C(OC=3C=CC(NC(=O)NC=4C=C(C(Cl)=CC=4)C(F)(F)F)=CC=3)C=2)=C1 QLJWNTHEJPFKDE-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- YYWASWTZUARRCQ-LJAQVGFWSA-N methyl (2s)-1-[2-[[5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carbonyl]amino]ethyl]pyrrolidine-2-carboxylate Chemical compound COC(=O)[C@@H]1CCCN1CCNC(=O)C1=CNC(C=2N=CC=C(OC=3C=CC(NC(=O)NC=4C(=CC=C(C)C=4)F)=CC=3)C=2)=C1 YYWASWTZUARRCQ-LJAQVGFWSA-N 0.000 claims description 2
- GDVIJPSACXJPNX-UHFFFAOYSA-N methyl 5-[4-[2-fluoro-4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C1=CNC(C=2N=CC=C(OC=3C(=CC(NC(=O)NC=4C(=CC=C(C)C=4)F)=CC=3)F)C=2)=C1 GDVIJPSACXJPNX-UHFFFAOYSA-N 0.000 claims description 2
- QMTUQSYQTDJUEC-UHFFFAOYSA-N methyl 5-[4-[3-fluoro-4-[(3-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C1=CNC(C=2N=CC=C(OC=3C=C(F)C(NC(=O)NC=4C=C(C)C=CC=4)=CC=3)C=2)=C1 QMTUQSYQTDJUEC-UHFFFAOYSA-N 0.000 claims description 2
- QJAIWFQXMXEWND-UHFFFAOYSA-N n-(2,3-dihydroxypropyl)-5-[4-[4-[(3-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NCC(O)CO)=CC=2)=C1 QJAIWFQXMXEWND-UHFFFAOYSA-N 0.000 claims description 2
- IQGOAXWKSXBKRE-UHFFFAOYSA-N n-[4-(2,3-dihydroxypropylamino)-4-oxobutyl]-5-[4-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxamide Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NCCCC(=O)NCC(O)CO)=CC=2)=C1 IQGOAXWKSXBKRE-UHFFFAOYSA-N 0.000 claims description 2
- DBWLZXDWSDEPMX-UHFFFAOYSA-N n-ethyl-5-[4-[3-[(3-methylfuran-2-carbonyl)amino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxamide Chemical compound CCNC(=O)C1=CNC(C=2N=CC=C(OC=3C=C(NC(=O)C4=C(C=CO4)C)C=CC=3)C=2)=C1 DBWLZXDWSDEPMX-UHFFFAOYSA-N 0.000 claims description 2
- PXZFHUFQTMBXSX-UHFFFAOYSA-N n-ethyl-5-[4-[3-fluoro-4-[(3-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxamide Chemical compound CCNC(=O)C1=CNC(C=2N=CC=C(OC=3C=C(F)C(NC(=O)NC=4C=C(C)C=CC=4)=CC=3)C=2)=C1 PXZFHUFQTMBXSX-UHFFFAOYSA-N 0.000 claims description 2
- QCFCYTRQICLOAN-UHFFFAOYSA-N n-methyl-5-[4-[4-[(3-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxamide Chemical compound CNC(=O)C1=CNC(C=2N=CC=C(OC=3C=CC(NC(=O)NC=4C=C(C)C=CC=4)=CC=3)C=2)=C1 QCFCYTRQICLOAN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-M prolinate Chemical compound [O-]C(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-M 0.000 claims 2
- BZRWMATYFFIEGO-UHFFFAOYSA-N 1-(2-fluoro-5-methylphenyl)-3-[4-[2-(1h-pyrrol-2-yl)pyridin-4-yl]phenyl]urea Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(=CC=2)C=2C=C(N=CC=2)C=2NC=CC=2)=C1 BZRWMATYFFIEGO-UHFFFAOYSA-N 0.000 claims 1
- SGUHQCHNFGIZSH-UHFFFAOYSA-N 1-(2-fluoro-5-methylphenyl)-3-[4-[2-(1h-pyrrol-3-yl)pyridin-4-yl]phenyl]urea Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(=CC=2)C=2C=C(N=CC=2)C2=CNC=C2)=C1 SGUHQCHNFGIZSH-UHFFFAOYSA-N 0.000 claims 1
- NOXFSIVDACCZOV-HXUWFJFHSA-N 1-[2-fluoro-4-[2-[4-[(3r)-3-hydroxypyrrolidine-1-carbonyl]-1h-pyrrol-2-yl]pyridin-4-yl]oxyphenyl]-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2C(=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)N3C[C@H](O)CC3)=CC=2)F)=C1 NOXFSIVDACCZOV-HXUWFJFHSA-N 0.000 claims 1
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- BQXJKTNDTCAOCP-UHFFFAOYSA-N n-hydroxy-5-[4-[4-[(3-methylphenyl)carbamoylamino]phenoxy]pyridin-2-yl]-1h-pyrrole-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(OC=3C=C(N=CC=3)C=3NC=C(C=3)C(=O)NO)=CC=2)=C1 BQXJKTNDTCAOCP-UHFFFAOYSA-N 0.000 description 1
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- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
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- QGMRQYFBGABWDR-UHFFFAOYSA-N sodium;5-ethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)NC1=O QGMRQYFBGABWDR-UHFFFAOYSA-N 0.000 description 1
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- GZHLCAQAPVGBJE-UHFFFAOYSA-N tert-butyl n-[4-(2-chloropyridin-4-yl)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C1=CC=NC(Cl)=C1 GZHLCAQAPVGBJE-UHFFFAOYSA-N 0.000 description 1
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- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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Landscapes
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Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23960309P | 2009-09-03 | 2009-09-03 | |
| US61/239,603 | 2009-09-03 | ||
| US30661610P | 2010-02-22 | 2010-02-22 | |
| US61/306,616 | 2010-02-22 | ||
| US35669910P | 2010-06-21 | 2010-06-21 | |
| US61/356,699 | 2010-06-21 | ||
| US36053110P | 2010-07-01 | 2010-07-01 | |
| US61/360,531 | 2010-07-01 | ||
| PCT/US2010/047800 WO2011028995A1 (en) | 2009-09-03 | 2010-09-03 | Compounds as tyrosine kinase modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2010289353A1 AU2010289353A1 (en) | 2012-03-29 |
| AU2010289353B2 true AU2010289353B2 (en) | 2016-12-08 |
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| Application Number | Title | Priority Date | Filing Date |
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| AU2010289353A Ceased AU2010289353B2 (en) | 2009-09-03 | 2010-09-03 | Compounds as tyrosine kinase modulators |
| AU2010289359A Abandoned AU2010289359A1 (en) | 2009-09-03 | 2010-09-03 | Compounds as tyrosine kinase modulators |
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- 2010-09-03 KR KR1020127008527A patent/KR20120047313A/ko not_active Withdrawn
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- 2010-09-03 AU AU2010289359A patent/AU2010289359A1/en not_active Abandoned
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