RU2672100C2 - Композиции и способы ингибирования пути jak - Google Patents

Info

Publication number

RU2672100C2

RU2672100C2 RU2015122016A RU2015122016A RU2672100C2 RU 2672100 C2 RU2672100 C2 RU 2672100C2 RU 2015122016 A RU2015122016 A RU 2015122016A RU 2015122016 A RU2015122016 A RU 2015122016A RU 2672100 C2 RU2672100 C2 RU 2672100C2

Authority

RU

Russia

Prior art keywords

ylamino

oxazol

benzo

methyl

fluoro

Prior art date

2010-07-28

Links

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• 238000000034 method Methods 0.000 title claims abstract description 95
• 239000000203 mixture Substances 0.000 title claims description 101
• 230000005764 inhibitory process Effects 0.000 title description 15
• 150000001875 compounds Chemical class 0.000 claims abstract description 402
• 150000003839 salts Chemical class 0.000 claims abstract description 68
• 125000003118 aryl group Chemical group 0.000 claims abstract description 60
• 230000000694 effects Effects 0.000 claims abstract description 57
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 53
• 150000002367 halogens Chemical class 0.000 claims abstract description 49
• 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 claims abstract description 34
• 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 claims abstract description 34
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 12
• ACIMRXKJKQGBGL-UHFFFAOYSA-N N-(2-aminoethyl)-5-chloro-1-naphthalenesulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)NCCN)=CC=CC2=C1Cl ACIMRXKJKQGBGL-UHFFFAOYSA-N 0.000 claims abstract description 11
• UZSSGAOAYPICBZ-SOCHQFKDSA-N Decoyinine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@]1(CO)OC(=C)[C@@H](O)[C@H]1O UZSSGAOAYPICBZ-SOCHQFKDSA-N 0.000 claims abstract description 10
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 6
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 6
• 125000005241 heteroarylamino group Chemical group 0.000 claims abstract description 6
• XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical compound NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-UHFFFAOYSA-N 0.000 claims abstract description 3
• 150000008052 alkyl sulfonates Chemical class 0.000 claims abstract description 3
• 150000001540 azides Chemical class 0.000 claims abstract description 3
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 3
• 125000005228 aryl sulfonate group Chemical group 0.000 claims abstract 2
• -1 pyrrolidinylmethyl Chemical group 0.000 claims description 214
• 125000000217 alkyl group Chemical group 0.000 claims description 185
• 125000004429 atom Chemical group 0.000 claims description 64
• 238000006243 chemical reaction Methods 0.000 claims description 58
• 229910052799 carbon Inorganic materials 0.000 claims description 55
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 125000004432 carbon atom Chemical group C* 0.000 claims description 40
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
• 229910052805 deuterium Inorganic materials 0.000 claims description 31
• 125000001424 substituent group Chemical group 0.000 claims description 30
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 30
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 29
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 29
• 239000008194 pharmaceutical composition Substances 0.000 claims description 29
• 229910052731 fluorine Inorganic materials 0.000 claims description 23
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
• 239000002253 acid Substances 0.000 claims description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
• 125000002091 cationic group Chemical group 0.000 claims description 16
• 230000002401 inhibitory effect Effects 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 125000005605 benzo group Chemical group 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
• ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 12
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
• 150000004675 formic acid derivatives Chemical class 0.000 claims description 10
• 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 10
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
• 239000012634 fragment Substances 0.000 claims description 8
• ITDXRIFHDJKTAA-UHFFFAOYSA-N 3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2OC(=O)NC2=C1 ITDXRIFHDJKTAA-UHFFFAOYSA-N 0.000 claims description 7
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 7
• 230000003993 interaction Effects 0.000 claims description 7
• OYFMQDVLFYKOPZ-UHFFFAOYSA-N 5-[[2-(4-fluoro-3-methoxy-5-methylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound CC1=C(F)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 OYFMQDVLFYKOPZ-UHFFFAOYSA-N 0.000 claims description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims description 5
• CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 claims description 4
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 3
• 229940092714 benzenesulfonic acid Drugs 0.000 claims description 3
• FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical group CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 claims description 3
• 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
• HMHIINMUADBISS-UHFFFAOYSA-N 2-[4-[[5-methyl-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]phenyl]acetaldehyde Chemical compound N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC=C(CC=O)C=C1 HMHIINMUADBISS-UHFFFAOYSA-N 0.000 claims description 2
• ZBFLAFGUXWQKFQ-UHFFFAOYSA-N 2-anilino-4-[(2-oxo-3H-1,3-benzoxazol-5-yl)amino]pyrimidine-5-carboxylic acid methyl 2,2,2-trifluoroacetate Chemical compound FC(C(=O)OC)(F)F.O=C1OC2=C(N1)C=C(C=C2)NC2=NC(=NC=C2C(=O)O)NC2=CC=CC=C2 ZBFLAFGUXWQKFQ-UHFFFAOYSA-N 0.000 claims description 2
• BOKOUDYMWNXLGH-UHFFFAOYSA-N 5-[(2-anilino-5-chloropyrimidin-4-yl)amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(Cl)=CN=C1NC1=CC=CC=C1 BOKOUDYMWNXLGH-UHFFFAOYSA-N 0.000 claims description 2
• BLKCWNVNVANBHP-UHFFFAOYSA-N 5-[(2-anilino-5-nitropyrimidin-4-yl)amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C([N+](=O)[O-])=CN=C1NC1=CC=CC=C1 BLKCWNVNVANBHP-UHFFFAOYSA-N 0.000 claims description 2
• VYAOXGKPFCICGJ-UHFFFAOYSA-N 5-[[2-(2-fluoro-3-methoxy-4-methylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(C)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1F VYAOXGKPFCICGJ-UHFFFAOYSA-N 0.000 claims description 2
• OKSYUCSOWVGFFQ-UHFFFAOYSA-N 5-[[2-(2-fluoro-3-methoxyanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound COC1=CC=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1F OKSYUCSOWVGFFQ-UHFFFAOYSA-N 0.000 claims description 2
• KSCNGRQEMCGODB-UHFFFAOYSA-N 5-[[2-(2-fluoro-3-methoxyanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound COC1=CC=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C=CN=2)=C1F KSCNGRQEMCGODB-UHFFFAOYSA-N 0.000 claims description 2
• JMQUFKAINVANSW-UHFFFAOYSA-N 5-[[2-(3,5-difluoroanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC(F)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C=CN=2)=C1 JMQUFKAINVANSW-UHFFFAOYSA-N 0.000 claims description 2
• JVBYWYIIGLWBAS-UHFFFAOYSA-N 5-[[2-(3-amino-4-methoxyanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C(N)C(OC)=CC=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 JVBYWYIIGLWBAS-UHFFFAOYSA-N 0.000 claims description 2
• GNTPRUJZPJGVMH-UHFFFAOYSA-N 5-[[2-(3-ethynylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC=CC(C#C)=C1 GNTPRUJZPJGVMH-UHFFFAOYSA-N 0.000 claims description 2
• QCOQSJQNULAJKM-UHFFFAOYSA-N 5-[[2-(4-bromo-2-fluoro-3-methoxyanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound COC1=C(Br)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1F QCOQSJQNULAJKM-UHFFFAOYSA-N 0.000 claims description 2
• HRWLPOMEBUHZLR-UHFFFAOYSA-N 5-[[2-(4-bromo-2-fluoroanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC=C(Br)C=C1F HRWLPOMEBUHZLR-UHFFFAOYSA-N 0.000 claims description 2
• YNKCDAARVJNKSA-UHFFFAOYSA-N 5-[[2-[3-(dimethylamino)-4-methylanilino]-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C(C)C(N(C)C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 YNKCDAARVJNKSA-UHFFFAOYSA-N 0.000 claims description 2
• YSQNLYBWTIBHFU-UHFFFAOYSA-N 5-[[2-[3-(dimethylamino)anilino]-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CN(C)C1=CC=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 YSQNLYBWTIBHFU-UHFFFAOYSA-N 0.000 claims description 2
• ZOLLHYPYOQXTEW-UHFFFAOYSA-N 5-[[2-[4-(dimethylamino)anilino]-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(N(C)C)=CC=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 ZOLLHYPYOQXTEW-UHFFFAOYSA-N 0.000 claims description 2
• BZGCHAYSFFSKTK-UHFFFAOYSA-N 5-[[5-bromo-2-(2-fluoro-3-methoxyanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Br)=CN=2)=C1F BZGCHAYSFFSKTK-UHFFFAOYSA-N 0.000 claims description 2
• DUZMXPNXGJGDQS-UHFFFAOYSA-N 5-[[5-chloro-2-(2,4-difluoro-3-methoxyanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(F)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1F DUZMXPNXGJGDQS-UHFFFAOYSA-N 0.000 claims description 2
• VJCCPKSVAOLCRI-UHFFFAOYSA-N 5-[[5-chloro-2-(2-fluoro-3-methoxyanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1F VJCCPKSVAOLCRI-UHFFFAOYSA-N 0.000 claims description 2
• GENIXLCRLWAHAZ-UHFFFAOYSA-N 5-[[5-chloro-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 GENIXLCRLWAHAZ-UHFFFAOYSA-N 0.000 claims description 2
• BNVYMOWVFHEBJR-UHFFFAOYSA-N 5-[[5-chloro-2-(3,4-dimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(C)=CC=C1NC1=NC=C(Cl)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 BNVYMOWVFHEBJR-UHFFFAOYSA-N 0.000 claims description 2
• XELNVNDCHYKDEC-UHFFFAOYSA-N 5-[[5-chloro-2-(3,5-difluoroanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC(F)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 XELNVNDCHYKDEC-UHFFFAOYSA-N 0.000 claims description 2
• KEMDDOAWMAXOOG-UHFFFAOYSA-N 5-[[5-chloro-2-(3,5-dimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 KEMDDOAWMAXOOG-UHFFFAOYSA-N 0.000 claims description 2
• YHZZPEATIMDJTN-UHFFFAOYSA-N 5-[[5-chloro-2-(3-methoxy-4-methylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 YHZZPEATIMDJTN-UHFFFAOYSA-N 0.000 claims description 2
• HXYFJBBTYSXNHN-UHFFFAOYSA-N 5-[[5-chloro-2-[3-(dimethylamino)-4-methylanilino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C(C)C(N(C)C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 HXYFJBBTYSXNHN-UHFFFAOYSA-N 0.000 claims description 2
• MYLQPUBECGCDRQ-UHFFFAOYSA-N 5-[[5-chloro-2-[3-methoxy-5-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound FC(F)(F)C1=CC(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 MYLQPUBECGCDRQ-UHFFFAOYSA-N 0.000 claims description 2
• ATYYPGKXUVOHPQ-UHFFFAOYSA-N 5-[[5-chloro-2-[4-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(F)(F)F)=CC=C1NC1=NC=C(Cl)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 ATYYPGKXUVOHPQ-UHFFFAOYSA-N 0.000 claims description 2
• BMMXMRZEGJNSHN-UHFFFAOYSA-N 5-[[5-chloro-2-[4-methyl-3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1NC1=NC=C(Cl)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 BMMXMRZEGJNSHN-UHFFFAOYSA-N 0.000 claims description 2
• XIKRLGAXJHDMTA-UHFFFAOYSA-N 5-[[5-ethynyl-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C#C)=CN=2)=C1 XIKRLGAXJHDMTA-UHFFFAOYSA-N 0.000 claims description 2
• QYXDPMBTIORZRQ-UHFFFAOYSA-N 5-[[5-fluoro-2-(2-fluoro-3-methoxyanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1F QYXDPMBTIORZRQ-UHFFFAOYSA-N 0.000 claims description 2
• JZHBAFFHUGUDLQ-UHFFFAOYSA-N 5-[[5-fluoro-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]-2-methylbenzonitrile;formic acid Chemical compound OC=O.C1=C(C#N)C(C)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 JZHBAFFHUGUDLQ-UHFFFAOYSA-N 0.000 claims description 2
• YOOHQYJTDNEQLP-UHFFFAOYSA-N 5-[[5-methyl-2-(n-methylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound N=1C=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=NC=1N(C)C1=CC=CC=C1 YOOHQYJTDNEQLP-UHFFFAOYSA-N 0.000 claims description 2
• LBQMQLOLUKUONZ-UHFFFAOYSA-N 5-[[5-nitro-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(=CN=2)[N+]([O-])=O)=C1 LBQMQLOLUKUONZ-UHFFFAOYSA-N 0.000 claims description 2
• QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 2
• KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims description 2
• MBTOOKBKBYXTCE-UHFFFAOYSA-L disodium;methyl phosphate Chemical compound [Na+].[Na+].COP([O-])([O-])=O MBTOOKBKBYXTCE-UHFFFAOYSA-L 0.000 claims description 2
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 2
• JZFSLMDLIPKTAO-UHFFFAOYSA-N 1,3-dihydroazepin-2-one Chemical compound O=C1CC=CC=CN1 JZFSLMDLIPKTAO-UHFFFAOYSA-N 0.000 claims 2
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 2
• XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 claims 2
• WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 2
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
• VKPJOERCBNIOLN-UHFFFAOYSA-N 1,3-benzoxazole-2-carboxylic acid Chemical class C1=CC=C2OC(C(=O)O)=NC2=C1 VKPJOERCBNIOLN-UHFFFAOYSA-N 0.000 claims 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
• CQQBUBUDFYGWFV-UHFFFAOYSA-N 2,6-dimethyl-4-[[5-methyl-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]benzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC(C)=C(C#N)C(C)=C1 CQQBUBUDFYGWFV-UHFFFAOYSA-N 0.000 claims 1
• URBRJWZCJZCENQ-UHFFFAOYSA-N 2-[3-methoxy-5-(trifluoromethyl)anilino]-4-[(2-oxo-3H-1,3-benzoxazol-5-yl)amino]pyrimidine-5-carboxylic acid methyl 2,2,2-trifluoroacetate Chemical compound FC(C(=O)OC)(F)F.COC=1C=C(C=C(C1)C(F)(F)F)NC1=NC=C(C(=N1)NC=1C=CC2=C(NC(O2)=O)C1)C(=O)O URBRJWZCJZCENQ-UHFFFAOYSA-N 0.000 claims 1
• XKJMNBXQXFINKX-UHFFFAOYSA-N 2-fluoro-3-[[5-methyl-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]benzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC=CC(C#N)=C1F XKJMNBXQXFINKX-UHFFFAOYSA-N 0.000 claims 1
• QKHQEETZGJUPOR-UHFFFAOYSA-N 2-methoxy-6-methyl-4-[[5-methyl-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]benzoic acid Chemical compound CC1=C(C(O)=O)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 QKHQEETZGJUPOR-UHFFFAOYSA-N 0.000 claims 1
• PEWAIWRUUGVRFE-UHFFFAOYSA-N 3-[[5-chloro-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]-2-fluorobenzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C(C#N)C(F)=C1NC1=NC=C(Cl)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 PEWAIWRUUGVRFE-UHFFFAOYSA-N 0.000 claims 1
• KCUSGANGRWSONG-UHFFFAOYSA-N 4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]-2-(3,4,5-trimethylanilino)pyrimidine-5-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C(O)=O)=CN=2)=C1 KCUSGANGRWSONG-UHFFFAOYSA-N 0.000 claims 1
• TWDWCFOOEHBXTL-UHFFFAOYSA-N 4-[[5-chloro-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]-2,6-dimethylbenzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C#N)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 TWDWCFOOEHBXTL-UHFFFAOYSA-N 0.000 claims 1
• TZBLQBRLXLNABA-UHFFFAOYSA-N 4-[[5-fluoro-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]-2,6-dimethylbenzonitrile Chemical compound CC1=C(C#N)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 TZBLQBRLXLNABA-UHFFFAOYSA-N 0.000 claims 1
• ICIDGNQYUIUUBW-UHFFFAOYSA-N 4-[[5-fluoro-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]-n-propan-2-ylbenzamide;formic acid Chemical compound OC=O.C1=CC(C(=O)NC(C)C)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 ICIDGNQYUIUUBW-UHFFFAOYSA-N 0.000 claims 1
• DYWVLVRCGICTAV-UHFFFAOYSA-N 4-[[5-fluoro-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]-n-propylbenzamide;formic acid Chemical compound OC=O.C1=CC(C(=O)NCCC)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 DYWVLVRCGICTAV-UHFFFAOYSA-N 0.000 claims 1
• FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical compound O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 claims 1
• YLLIKDNBCSMBDD-UHFFFAOYSA-N 5-[(2-amino-5-fluoro-6-phenylpyrimidin-4-yl)amino]-3H-1,3-benzoxazol-2-one Chemical compound C1(=CC=CC=C1)C1=C(C(=NC(=N1)N)NC=1C=CC2=C(NC(O2)=O)C=1)F YLLIKDNBCSMBDD-UHFFFAOYSA-N 0.000 claims 1
• LHBFVVLCZDXDAL-UHFFFAOYSA-N 5-[[2-(2,4-difluoro-3-methoxyanilino)-5-fluoropyrimidin-4-yl]amino]-7-fluoro-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(F)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(F)C=3)C(F)=CN=2)=C1F LHBFVVLCZDXDAL-UHFFFAOYSA-N 0.000 claims 1
• AYPFNIHHENCZOS-UHFFFAOYSA-N 5-[[2-(2,4-difluoro-3-methoxyanilino)-5-fluoropyrimidin-4-yl]amino]-7-methyl-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(F)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(C)C=3)C(F)=CN=2)=C1F AYPFNIHHENCZOS-UHFFFAOYSA-N 0.000 claims 1
• BROZPOZIIOBNNZ-UHFFFAOYSA-N 5-[[2-(2,4-difluoro-3-methoxyanilino)-5-nitropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(F)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(=CN=2)[N+]([O-])=O)=C1F BROZPOZIIOBNNZ-UHFFFAOYSA-N 0.000 claims 1
• WQMZENQZLBGFSR-UHFFFAOYSA-N 5-[[2-(2-fluoro-3,4-dimethoxyanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound FC1=C(OC)C(OC)=CC=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 WQMZENQZLBGFSR-UHFFFAOYSA-N 0.000 claims 1
• GVJPNCTVCUNHMF-UHFFFAOYSA-N 5-[[2-(2-fluoro-4-methoxyanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC(OC)=CC=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 GVJPNCTVCUNHMF-UHFFFAOYSA-N 0.000 claims 1
• WKJGVCNCTBQCBE-UHFFFAOYSA-N 5-[[2-(2-fluoro-5-methoxy-4-methylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1F WKJGVCNCTBQCBE-UHFFFAOYSA-N 0.000 claims 1
• NEMMTUDMKUIEIH-UHFFFAOYSA-N 5-[[2-(3,4-diethoxy-2-fluoroanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound FC1=C(OCC)C(OCC)=CC=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 NEMMTUDMKUIEIH-UHFFFAOYSA-N 0.000 claims 1
• HUWBZBKNHFFQRB-UHFFFAOYSA-N 5-[[2-(3,4-dimethoxy-5-methylanilino)-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(OC)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 HUWBZBKNHFFQRB-UHFFFAOYSA-N 0.000 claims 1
• LJYJLNNEDSKUCB-UHFFFAOYSA-N 5-[[2-(3,4-dimethoxy-5-methylanilino)-5-fluoropyrimidin-4-yl]amino]-7-fluoro-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(OC)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(F)C=3)C(F)=CN=2)=C1 LJYJLNNEDSKUCB-UHFFFAOYSA-N 0.000 claims 1
• KEDJNSAGZCTYBO-UHFFFAOYSA-N 5-[[2-(3,4-dimethoxy-5-methylanilino)-5-fluoropyrimidin-4-yl]amino]-7-methyl-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(OC)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(C)C=3)C(F)=CN=2)=C1 KEDJNSAGZCTYBO-UHFFFAOYSA-N 0.000 claims 1
• GLCKZUYTFKFAMK-UHFFFAOYSA-N 5-[[2-(3,5-dimethoxy-4-methylanilino)-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 GLCKZUYTFKFAMK-UHFFFAOYSA-N 0.000 claims 1
• DREQQEMLRUFKMW-UHFFFAOYSA-N 5-[[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]amino]-7-fluoro-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(F)C=3)C(F)=CN=2)=C1 DREQQEMLRUFKMW-UHFFFAOYSA-N 0.000 claims 1
• NTGRYWTYJPJSFJ-UHFFFAOYSA-N 5-[[2-(3-chloro-4,5-dimethoxyanilino)-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.ClC1=C(OC)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 NTGRYWTYJPJSFJ-UHFFFAOYSA-N 0.000 claims 1
• QHDWBLMOMGHAKK-UHFFFAOYSA-N 5-[[2-(3-ethenylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC=CC(C=C)=C1 QHDWBLMOMGHAKK-UHFFFAOYSA-N 0.000 claims 1
• JJYGXMMABJKTPH-UHFFFAOYSA-N 5-[[2-(3-ethoxy-4,5-dimethylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CC1=C(C)C(OCC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 JJYGXMMABJKTPH-UHFFFAOYSA-N 0.000 claims 1
• KUVHOKHWQZUWKO-UHFFFAOYSA-N 5-[[2-(3-fluoro-5-methoxy-4-methylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 KUVHOKHWQZUWKO-UHFFFAOYSA-N 0.000 claims 1
• AVKXPBUFMRDXEH-UHFFFAOYSA-N 5-[[2-(3-hydroxy-4,5-dimethylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 AVKXPBUFMRDXEH-UHFFFAOYSA-N 0.000 claims 1
• HBOCQIHDTUDVTP-UHFFFAOYSA-N 5-[[2-(3-methoxy-4,5-dimethylanilino)-5-methylpyrimidin-4-yl]amino]-3-methyl-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4N(C)C(=O)OC4=CC=3)C(C)=CN=2)=C1 HBOCQIHDTUDVTP-UHFFFAOYSA-N 0.000 claims 1
• COTIWYLHNXISES-UHFFFAOYSA-N 5-[[2-(3-methoxy-4-methylanilino)-5-nitropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(=CN=2)[N+]([O-])=O)=C1 COTIWYLHNXISES-UHFFFAOYSA-N 0.000 claims 1
• FSLCUHMAKWEUES-UHFFFAOYSA-N 5-[[2-(4-acetylanilino)-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.C1=CC(C(=O)C)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 FSLCUHMAKWEUES-UHFFFAOYSA-N 0.000 claims 1
• UMDISBJYUCBPFF-UHFFFAOYSA-N 5-[[2-(4-chloro-3-methoxy-5-methylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(Cl)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 UMDISBJYUCBPFF-UHFFFAOYSA-N 0.000 claims 1
• ZWTTWPXVYXPGTD-UHFFFAOYSA-N 5-[[2-(4-ethyl-2-fluoro-3-methoxyanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=C(OC)C(CC)=CC=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 ZWTTWPXVYXPGTD-UHFFFAOYSA-N 0.000 claims 1
• VROLPBWAQGBYKK-UHFFFAOYSA-N 5-[[2-(4-fluoro-3,5-dimethylanilino)-5-(hydroxymethyl)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(F)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(CO)=CN=2)=C1 VROLPBWAQGBYKK-UHFFFAOYSA-N 0.000 claims 1
• GZCZJWRMRAOXIT-UHFFFAOYSA-N 5-[[2-(4-fluoro-3-hydroxy-5-methylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC(C)=C(F)C(O)=C1 GZCZJWRMRAOXIT-UHFFFAOYSA-N 0.000 claims 1
• HWZZOVQPWBJYQL-UHFFFAOYSA-N 5-[[2-(4-fluoro-3-methoxy-5-methylanilino)-5-(hydroxymethyl)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(F)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(CO)=CN=2)=C1 HWZZOVQPWBJYQL-UHFFFAOYSA-N 0.000 claims 1
• CKLPWGFITVLGCQ-UHFFFAOYSA-N 5-[[2-(4-fluoro-3-methoxy-5-methylanilino)-5-methylpyrimidin-4-yl]amino]-3-methyl-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(F)C(OC)=CC(NC=2N=C(NC=3C=C4N(C)C(=O)OC4=CC=3)C(C)=CN=2)=C1 CKLPWGFITVLGCQ-UHFFFAOYSA-N 0.000 claims 1
• JAEWYAMEKSUVPM-UHFFFAOYSA-N 5-[[2-(4-fluoro-3-methoxy-5-methylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.CC1=C(F)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 JAEWYAMEKSUVPM-UHFFFAOYSA-N 0.000 claims 1
• GGKVSHKBQILWRO-UHFFFAOYSA-N 5-[[2-(4-tert-butylanilino)-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 GGKVSHKBQILWRO-UHFFFAOYSA-N 0.000 claims 1
• IYJHSBLERTUKDP-UHFFFAOYSA-N 5-[[2-(naphthalen-2-ylamino)-5-nitropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C2OC(=O)NC2=CC(NC2=NC(NC=3C=C4C=CC=CC4=CC=3)=NC=C2[N+](=O)[O-])=C1 IYJHSBLERTUKDP-UHFFFAOYSA-N 0.000 claims 1
• CFSBKLWTWMHTBC-UHFFFAOYSA-N 5-[[2-[2-fluoro-3,4-bis(2-methoxyethoxy)anilino]-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=C(OCCOC)C(OCCOC)=CC=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 CFSBKLWTWMHTBC-UHFFFAOYSA-N 0.000 claims 1
• QYYITZDBQZKOLN-UHFFFAOYSA-N 5-[[2-[2-fluoro-3-(2-methoxyethoxy)-4-methylanilino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound COCCOC1=C(C)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C=CN=2)=C1F QYYITZDBQZKOLN-UHFFFAOYSA-N 0.000 claims 1
• YOITXWSPDHPUBB-UHFFFAOYSA-N 5-[[2-[3,5-dimethyl-4-(2-morpholin-4-ylethoxy)anilino]-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CC1=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=CC(C)=C1OCCN1CCOCC1 YOITXWSPDHPUBB-UHFFFAOYSA-N 0.000 claims 1
• MUTAUXXWKDPITI-UHFFFAOYSA-N 5-[[2-[3-(diethylamino)-4,5-dimethylanilino]-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.CC1=C(C)C(N(CC)CC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 MUTAUXXWKDPITI-UHFFFAOYSA-N 0.000 claims 1
• VFKZJNPGIPLQCI-UHFFFAOYSA-N 5-[[2-[3-(difluoromethyl)-4-methoxyanilino]-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.C1=C(C(F)F)C(OC)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 VFKZJNPGIPLQCI-UHFFFAOYSA-N 0.000 claims 1
• NWODTCNZENWTOY-UHFFFAOYSA-N 5-[[2-[3-(difluoromethyl)-5-methoxyanilino]-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC(F)C1=CC(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 NWODTCNZENWTOY-UHFFFAOYSA-N 0.000 claims 1
• JEPTVSSWKRQJLD-UHFFFAOYSA-N 5-[[2-[3-(dimethylamino)-4,5-dimethylanilino]-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C)C(N(C)C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 JEPTVSSWKRQJLD-UHFFFAOYSA-N 0.000 claims 1
• YVRYSNGXLGNLFO-UHFFFAOYSA-N 5-[[2-[3-(dimethylamino)-4-methylanilino]-5-nitropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(N(C)C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(=CN=2)[N+]([O-])=O)=C1 YVRYSNGXLGNLFO-UHFFFAOYSA-N 0.000 claims 1
• YUQIJGOQCPKEIM-UHFFFAOYSA-N 5-[[2-[3-methoxy-5-(trifluoromethyl)anilino]-5-nitropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C1=CC(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(=CN=2)[N+]([O-])=O)=C1 YUQIJGOQCPKEIM-UHFFFAOYSA-N 0.000 claims 1
• COUPJNGWDHLZGN-UHFFFAOYSA-N 5-[[2-[4-(aminomethyl)anilino]-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC=C(CN)C=C1 COUPJNGWDHLZGN-UHFFFAOYSA-N 0.000 claims 1
• SLGQVMOAABOCOY-UHFFFAOYSA-N 5-[[2-[4-[1-(cyclopropylamino)ethyl]anilino]-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C=1C=C(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)C=CC=1C(C)NC1CC1 SLGQVMOAABOCOY-UHFFFAOYSA-N 0.000 claims 1
• GMZVMSJYNZWIPD-UHFFFAOYSA-N 5-[[5-(diethylaminomethyl)-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(CN(CC)CC)=CN=C1NC1=CC(C)=C(C)C(C)=C1 GMZVMSJYNZWIPD-UHFFFAOYSA-N 0.000 claims 1
• AAMICGWLGOWTGQ-UHFFFAOYSA-N 5-[[5-(hydroxymethyl)-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(CO)=CN=2)=C1 AAMICGWLGOWTGQ-UHFFFAOYSA-N 0.000 claims 1
• ZCBLRDRYHMWLTJ-UHFFFAOYSA-N 5-[[5-(hydroxymethyl)-2-(3-methoxy-4,5-dimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(CO)=CN=2)=C1 ZCBLRDRYHMWLTJ-UHFFFAOYSA-N 0.000 claims 1
• PTWFXANMNNESDZ-UHFFFAOYSA-N 5-[[5-(piperidin-1-ylmethyl)-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(CN3CCCCC3)=CN=2)=C1 PTWFXANMNNESDZ-UHFFFAOYSA-N 0.000 claims 1
• KPJOYTSBHHLWFP-UHFFFAOYSA-N 5-[[5-(pyrrolidin-1-ylmethyl)-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(CN3CCCC3)=CN=2)=C1 KPJOYTSBHHLWFP-UHFFFAOYSA-N 0.000 claims 1
• OVXUUNUWTFKTOC-UHFFFAOYSA-N 5-[[5-bromo-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Br)=CN=2)=C1 OVXUUNUWTFKTOC-UHFFFAOYSA-N 0.000 claims 1
• RMFRBTUIRARYSZ-UHFFFAOYSA-N 5-[[5-chloro-2-(2-fluoro-3,4-dimethoxyanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=C(OC)C(OC)=CC=C1NC1=NC=C(Cl)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 RMFRBTUIRARYSZ-UHFFFAOYSA-N 0.000 claims 1
• ROPTYKBVEBINSV-UHFFFAOYSA-N 5-[[5-chloro-2-(2-fluoro-3-methoxy-4-methylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound COC1=C(C)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1F ROPTYKBVEBINSV-UHFFFAOYSA-N 0.000 claims 1
• VLECTBJEUXXLQO-UHFFFAOYSA-N 5-[[5-chloro-2-(2-fluoro-4-methoxyanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC(OC)=CC=C1NC1=NC=C(Cl)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 VLECTBJEUXXLQO-UHFFFAOYSA-N 0.000 claims 1
• YJVHNPACTUFWTO-UHFFFAOYSA-N 5-[[5-chloro-2-(3-chloro-5-fluoroanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound FC1=CC(Cl)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 YJVHNPACTUFWTO-UHFFFAOYSA-N 0.000 claims 1
• MBFYWTCTJXNXMA-UHFFFAOYSA-N 5-[[5-chloro-2-(3-ethoxy-4,5-dimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CC1=C(C)C(OCC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 MBFYWTCTJXNXMA-UHFFFAOYSA-N 0.000 claims 1
• HJDNERITBHSIQC-UHFFFAOYSA-N 5-[[5-chloro-2-(3-methoxy-4,5-dimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound CC1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 HJDNERITBHSIQC-UHFFFAOYSA-N 0.000 claims 1
• ORBXGUMDIAQKRZ-UHFFFAOYSA-N 5-[[5-chloro-2-(4-ethyl-2-fluoro-3-methoxyanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=C(OC)C(CC)=CC=C1NC1=NC=C(Cl)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 ORBXGUMDIAQKRZ-UHFFFAOYSA-N 0.000 claims 1
• XKNVREXZUMXOKI-UHFFFAOYSA-N 5-[[5-chloro-2-[2-fluoro-3-(2-methoxyethoxy)-4-methylanilino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COCCOC1=C(C)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1F XKNVREXZUMXOKI-UHFFFAOYSA-N 0.000 claims 1
• HQZQNGPAMGTLPX-UHFFFAOYSA-N 5-[[5-chloro-2-[3-(diethylamino)-4,5-dimethylanilino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound CC1=C(C)C(N(CC)CC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 HQZQNGPAMGTLPX-UHFFFAOYSA-N 0.000 claims 1
• POLNHIPOHBFNGV-UHFFFAOYSA-N 5-[[5-chloro-2-[3-(dimethylamino)-4,5-dimethylanilino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C)C(N(C)C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 POLNHIPOHBFNGV-UHFFFAOYSA-N 0.000 claims 1
• UMLVVHPQYZPUOP-UHFFFAOYSA-N 5-[[5-chloro-2-[3-(ethylamino)-4,5-dimethylanilino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.CC1=C(C)C(NCC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 UMLVVHPQYZPUOP-UHFFFAOYSA-N 0.000 claims 1
• MEDJFAMZPLGSJI-UHFFFAOYSA-N 5-[[5-fluoro-2-(2-fluoro-5-methoxy-4-methylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1F MEDJFAMZPLGSJI-UHFFFAOYSA-N 0.000 claims 1
• JHQZBABCLVFFOB-UHFFFAOYSA-N 5-[[5-fluoro-2-(2-fluoro-5-methoxyanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound COC1=CC=C(F)C(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 JHQZBABCLVFFOB-UHFFFAOYSA-N 0.000 claims 1
• PEXMFLWVCUGKCK-UHFFFAOYSA-N 5-[[5-fluoro-2-(3-fluoro-5-methoxy-4-methylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 PEXMFLWVCUGKCK-UHFFFAOYSA-N 0.000 claims 1
• DXUIJJIHRUCPGC-UHFFFAOYSA-N 5-[[5-fluoro-2-(3-fluoro-5-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C=1C(F)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=CC=1N1CCOCC1 DXUIJJIHRUCPGC-UHFFFAOYSA-N 0.000 claims 1
• ZAZJNSZVNNDZJS-UHFFFAOYSA-N 5-[[5-fluoro-2-(3-methoxy-4,5-dimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 ZAZJNSZVNNDZJS-UHFFFAOYSA-N 0.000 claims 1
• KHZDBVDMSAMEMZ-UHFFFAOYSA-N 5-[[5-fluoro-2-(3-methoxy-4,5-dimethylanilino)pyrimidin-4-yl]amino]-7-methyl-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(C)C=3)C(F)=CN=2)=C1 KHZDBVDMSAMEMZ-UHFFFAOYSA-N 0.000 claims 1
• TWHUNGUPDQPYLV-UHFFFAOYSA-N 5-[[5-fluoro-2-(3-methoxy-4-pyridin-4-ylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.COC1=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=CC=C1C1=CC=NC=C1 TWHUNGUPDQPYLV-UHFFFAOYSA-N 0.000 claims 1
• UCWSGAMXMRLDEX-UHFFFAOYSA-N 5-[[5-fluoro-2-(3-methoxy-5-methylanilino)pyrimidin-4-yl]amino]-7-methyl-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(C)C=3)C(F)=CN=2)=C1 UCWSGAMXMRLDEX-UHFFFAOYSA-N 0.000 claims 1
• NWQVDRDUGDSIMW-UHFFFAOYSA-N 5-[[5-fluoro-2-(3-methylsulfonylanilino)pyrimidin-4-yl]amino]-7-methyl-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=2NC(=O)OC=2C(C)=CC=1NC(C(=CN=1)F)=NC=1NC1=CC=CC(S(C)(=O)=O)=C1 NWQVDRDUGDSIMW-UHFFFAOYSA-N 0.000 claims 1
• GNDHRBINUQZCFN-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-fluoro-3-methoxy-5-methylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(F)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 GNDHRBINUQZCFN-UHFFFAOYSA-N 0.000 claims 1
• XBUMMSLSFKLLIF-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-fluoro-3-methoxy-5-methylanilino)pyrimidin-4-yl]amino]-7-methyl-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(F)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(C)C=3)C(F)=CN=2)=C1 XBUMMSLSFKLLIF-UHFFFAOYSA-N 0.000 claims 1
• RYFZBRREBQSYRQ-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-fluoro-3-methylsulfonylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(F)C(S(=O)(=O)C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 RYFZBRREBQSYRQ-UHFFFAOYSA-N 0.000 claims 1
• QNOFZZUSWVWIKG-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-fluoro-3-methylsulfonylanilino)pyrimidin-4-yl]amino]-7-methyl-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=2NC(=O)OC=2C(C)=CC=1NC(C(=CN=1)F)=NC=1NC1=CC=C(F)C(S(C)(=O)=O)=C1 QNOFZZUSWVWIKG-UHFFFAOYSA-N 0.000 claims 1
• PJSFYGWRDRCBIJ-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-fluoro-3-pyridin-3-ylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(F)=CN=C1NC(C=1)=CC=C(F)C=1C1=CC=CN=C1 PJSFYGWRDRCBIJ-UHFFFAOYSA-N 0.000 claims 1
• CZTRBCDKVZGMAM-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-fluoro-3-pyridin-4-ylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(F)=CN=C1NC(C=1)=CC=C(F)C=1C1=CC=NC=C1 CZTRBCDKVZGMAM-UHFFFAOYSA-N 0.000 claims 1
• CAEAKBSFASJTNI-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-methoxy-3-methylanilino)pyrimidin-4-yl]amino]-7-methyl-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(OC)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=C(C)C=2)=N1 CAEAKBSFASJTNI-UHFFFAOYSA-N 0.000 claims 1
• WEPVLKXHUAGGPU-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-methoxy-3-pyridin-3-ylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.COC1=CC=C(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)C=C1C1=CC=CN=C1 WEPVLKXHUAGGPU-UHFFFAOYSA-N 0.000 claims 1
• XWRRTJFJLBCAMT-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-methoxy-3-pyridin-4-ylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.COC1=CC=C(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)C=C1C1=CC=NC=C1 XWRRTJFJLBCAMT-UHFFFAOYSA-N 0.000 claims 1
• GSDUCFHWKMQUSG-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-methoxyanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 GSDUCFHWKMQUSG-UHFFFAOYSA-N 0.000 claims 1
• KWKQAHGTZVWORD-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-methyl-3-methylsulfonylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(S(C)(=O)=O)C(C)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 KWKQAHGTZVWORD-UHFFFAOYSA-N 0.000 claims 1
• VBVDSBUIMQLWLW-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-methyl-3-pyridin-3-ylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound CC1=CC=C(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)C=C1C1=CC=CN=C1 VBVDSBUIMQLWLW-UHFFFAOYSA-N 0.000 claims 1
• ZGCZJVPJRQRDNE-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-methyl-3-pyridin-4-ylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound CC1=CC=C(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)C=C1C1=CC=NC=C1 ZGCZJVPJRQRDNE-UHFFFAOYSA-N 0.000 claims 1
• KIYPEMMSKNWKEE-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-methylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 KIYPEMMSKNWKEE-UHFFFAOYSA-N 0.000 claims 1
• SQIMBNBBTOWRQC-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-propan-2-ylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(C)C)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 SQIMBNBBTOWRQC-UHFFFAOYSA-N 0.000 claims 1
• IHEPMBVCENAQTA-UHFFFAOYSA-N 5-[[5-fluoro-2-[2-fluoro-3-(2-methoxyethoxy)-4-methylanilino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COCCOC1=C(C)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1F IHEPMBVCENAQTA-UHFFFAOYSA-N 0.000 claims 1
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