CA2804199C - Compositions and methods for inhibition of the jak pathway - Google Patents

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Publication number

CA2804199C

CA2804199C CA2804199A CA2804199A CA2804199C CA 2804199 C CA2804199 C CA 2804199C CA 2804199 A CA2804199 A CA 2804199A CA 2804199 A CA2804199 A CA 2804199A CA 2804199 C CA2804199 C CA 2804199C

Authority

CA

Canada

Prior art keywords

ylamino

oxazol

benzo

methyl

pyrimidin

Prior art date

2010-07-28

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.)

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• 238000000034 method Methods 0.000 title claims abstract description 86
• 239000000203 mixture Substances 0.000 title abstract description 96
• 230000037361 pathway Effects 0.000 title abstract description 37
• 230000005764 inhibitory process Effects 0.000 title abstract description 17
• 150000001875 compounds Chemical class 0.000 claims abstract description 404
• 102000042838 JAK family Human genes 0.000 claims abstract description 84
• 108091082332 JAK family Proteins 0.000 claims abstract description 84
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 133
• -1 -OCH2F Chemical group 0.000 claims description 116
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 82
• 150000003839 salts Chemical class 0.000 claims description 75
• 125000004429 atom Chemical group 0.000 claims description 69
• 239000003795 chemical substances by application Substances 0.000 claims description 64
• 201000010099 disease Diseases 0.000 claims description 53
• 125000005843 halogen group Chemical group 0.000 claims description 52
• 229910052799 carbon Inorganic materials 0.000 claims description 51
• 230000000694 effects Effects 0.000 claims description 50
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 48
• 125000000217 alkyl group Chemical group 0.000 claims description 45
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 125000003118 aryl group Chemical group 0.000 claims description 36
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
• 230000001404 mediated effect Effects 0.000 claims description 32
• 229910052805 deuterium Inorganic materials 0.000 claims description 30
• 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 30
• 239000008194 pharmaceutical composition Substances 0.000 claims description 30
• ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 29
• 208000035475 disorder Diseases 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 28
• 125000004122 cyclic group Chemical group 0.000 claims description 28
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• 229910052731 fluorine Inorganic materials 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 208000023275 Autoimmune disease Diseases 0.000 claims description 20
• 210000001744 T-lymphocyte Anatomy 0.000 claims description 20
• 125000002091 cationic group Chemical group 0.000 claims description 20
• 230000002401 inhibitory effect Effects 0.000 claims description 18
• 206010052779 Transplant rejections Diseases 0.000 claims description 17
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 16
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
• 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 description 12
• 239000008177 pharmaceutical agent Substances 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 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 11
• 125000002619 bicyclic group Chemical group 0.000 claims description 11
• 125000002950 monocyclic group Chemical group 0.000 claims description 11
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 10
• 210000004072 lung Anatomy 0.000 claims description 10
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
• 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 10
• 239000003085 diluting agent Substances 0.000 claims description 9
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 150000002367 halogens Chemical class 0.000 claims description 9
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 8
• 206010013774 Dry eye Diseases 0.000 claims description 8
• 208000010412 Glaucoma Diseases 0.000 claims description 8
• BVMWIXWOIGJRGE-UHFFFAOYSA-N NP(O)=O Chemical group NP(O)=O BVMWIXWOIGJRGE-UHFFFAOYSA-N 0.000 claims description 8
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 208000003556 Dry Eye Syndromes Diseases 0.000 claims description 7
• 102000000551 Syk Kinase Human genes 0.000 claims description 7
• 108010016672 Syk Kinase Proteins 0.000 claims description 7
• 239000011734 sodium Substances 0.000 claims description 7
• WCYWZMWISLQXQU-FIBGUPNXSA-N trideuteriomethane Chemical compound [2H][C]([2H])[2H] WCYWZMWISLQXQU-FIBGUPNXSA-N 0.000 claims description 7
• 208000027930 type IV hypersensitivity disease Diseases 0.000 claims description 7
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
• 210000004185 liver Anatomy 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
• 206010053613 Type IV hypersensitivity reaction Diseases 0.000 claims description 5
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
• 230000001419 dependent effect Effects 0.000 claims description 5
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 5
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 5
• 239000003018 immunosuppressive agent Substances 0.000 claims description 5
• 210000003734 kidney Anatomy 0.000 claims description 5
• 229910052708 sodium Inorganic materials 0.000 claims description 5
• 206010046851 Uveitis Diseases 0.000 claims description 4
• 239000000969 carrier Substances 0.000 claims description 4
• 210000002216 heart Anatomy 0.000 claims description 4
• 229960003444 immunosuppressant agent Drugs 0.000 claims description 4
• 230000001861 immunosuppressant effect Effects 0.000 claims description 4
• 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 3
• 241001303601 Rosacea Species 0.000 claims description 3
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 3
• 208000024998 atopic conjunctivitis Diseases 0.000 claims description 3
• CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 claims description 3
• 201000004700 rosacea Diseases 0.000 claims description 3
• ULHJGWARLNOYFU-UHFFFAOYSA-N 3-[[4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=O)C1=CC=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C=CN=2)=C1 ULHJGWARLNOYFU-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• BVPHLYQMKCCPLT-UHFFFAOYSA-N 4-[[4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(=O)N)=CC=C1NC1=NC=CC(NC=2C=C3NC(=O)OC3=CC=2)=N1 BVPHLYQMKCCPLT-UHFFFAOYSA-N 0.000 claims description 2
• HLUBTMFTYPLFLH-UHFFFAOYSA-N 4-[[5-chloro-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(=O)N)=CC=C1NC1=NC=C(Cl)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 HLUBTMFTYPLFLH-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• RZMMXZOLXNRTPJ-UHFFFAOYSA-N 4-[[5-nitro-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(=O)N)=CC=C1NC1=NC=C([N+]([O-])=O)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 RZMMXZOLXNRTPJ-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
• 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 description 2
• 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 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
• 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 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
• 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 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
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 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
• 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 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
• LPJSGIBWNPXPJX-UHFFFAOYSA-N 5-[[2-[3-(ethylamino)-4,5-dimethylanilino]-5-methylpyrimidin-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(C)=CN=2)=C1 LPJSGIBWNPXPJX-UHFFFAOYSA-N 0.000 claims description 2
• 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 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
• 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 description 2
• 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 description 2
• 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 description 2
• 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 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
• BEEMSVKKXCONKT-UHFFFAOYSA-N 5-[[5-bromo-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Br)=CN=2)=C1 BEEMSVKKXCONKT-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
• 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 description 2
• 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 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
• ZFYSYKRCYOUDGE-UHFFFAOYSA-N 5-[[5-chloro-2-(3-chloro-5-fluoroanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.FC1=CC(Cl)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(Cl)=CN=2)=C1 ZFYSYKRCYOUDGE-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• VPPRBIQUABUKSB-UHFFFAOYSA-N 5-[[5-chloro-2-[2-fluoro-3,4-bis(2-methoxyethoxy)anilino]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(OCCOC)C(OCCOC)=CC=C1NC1=NC=C(Cl)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 VPPRBIQUABUKSB-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• AEQXTASGRDDEQY-UHFFFAOYSA-N 5-[[5-chloro-2-[3-(diethylamino)-4,5-dimethylanilino]pyrimidin-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(Cl)=CN=2)=C1 AEQXTASGRDDEQY-UHFFFAOYSA-N 0.000 claims description 2
• 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 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
• 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 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
• 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
• 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 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
• ABOOBVBGPKLURH-UHFFFAOYSA-N 5-[[5-methyl-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-7-(piperazin-1-ylmethyl)-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(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(CN4CCNCC4)C=3)C(C)=CN=2)=C1 ABOOBVBGPKLURH-UHFFFAOYSA-N 0.000 claims description 2
• ZKRUHYBDTRDFJI-UHFFFAOYSA-N 5-[[5-methyl-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-7-(pyrrolidin-1-ylmethyl)-3h-1,3-benzoxazol-2-one Chemical compound CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(CN4CCCC4)C=3)C(C)=CN=2)=C1 ZKRUHYBDTRDFJI-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
• LLJAJYPWOPNTTR-UHFFFAOYSA-N 7-(diethylaminomethyl)-5-[[5-methyl-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.C=1C=2NC(=O)OC=2C(CN(CC)CC)=CC=1NC(C(=CN=1)C)=NC=1NC1=CC(C)=C(C)C(C)=C1 LLJAJYPWOPNTTR-UHFFFAOYSA-N 0.000 claims description 2
• MHADEGJBEHVPLK-UHFFFAOYSA-N 7-[(4-methylpiperazin-1-yl)methyl]-5-[[5-methyl-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1CN(C)CCN1CC1=CC(NC=2C(=CN=C(NC=3C=C(C)C(C)=C(C)C=3)N=2)C)=CC2=C1OC(=O)N2 MHADEGJBEHVPLK-UHFFFAOYSA-N 0.000 claims description 2
• YJFSIFQUYPPIPT-UHFFFAOYSA-N 7-[(dimethylamino)methyl]-5-[[5-methyl-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.C=1C=2NC(=O)OC=2C(CN(C)C)=CC=1NC(C(=CN=1)C)=NC=1NC1=CC(C)=C(C)C(C)=C1 YJFSIFQUYPPIPT-UHFFFAOYSA-N 0.000 claims description 2
• 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
• 150000001540 azides Chemical class 0.000 claims description 2
• ZRHCRAIVTOEDTD-UHFFFAOYSA-N methyl 2-(2,4-difluoro-3-methoxyanilino)-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidine-5-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C(=O)OC)=CN=C1NC1=CC=C(F)C(OC)=C1F ZRHCRAIVTOEDTD-UHFFFAOYSA-N 0.000 claims description 2
• YDDSESZOKYMUKP-UHFFFAOYSA-N methyl 2-(3-methoxy-4,5-dimethylanilino)-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidine-5-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C(=O)OC)=CN=C1NC1=CC(C)=C(C)C(OC)=C1 YDDSESZOKYMUKP-UHFFFAOYSA-N 0.000 claims description 2
• WMCIBLJIHULGLZ-UHFFFAOYSA-N methyl 2-(3-methoxy-4-methylanilino)-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidine-5-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C(=O)OC)=CN=C1NC1=CC=C(C)C(OC)=C1 WMCIBLJIHULGLZ-UHFFFAOYSA-N 0.000 claims description 2
• IMJZNRBKRFCBTC-UHFFFAOYSA-N methyl 2-(4-carbamoylanilino)-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidine-5-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C(=O)OC)=CN=C1NC1=CC=C(C(N)=O)C=C1 IMJZNRBKRFCBTC-UHFFFAOYSA-N 0.000 claims description 2
• AVOJLSCUURMSPL-UHFFFAOYSA-N methyl 2-(4-fluoro-3,5-dimethylanilino)-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidine-5-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C(=O)OC)=CN=C1NC1=CC(C)=C(F)C(C)=C1 AVOJLSCUURMSPL-UHFFFAOYSA-N 0.000 claims description 2
• OHCPSBQCCLBHGV-UHFFFAOYSA-N methyl 2-(4-fluoro-3-methoxy-5-methylanilino)-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidine-5-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C(=O)OC)=CN=C1NC1=CC(C)=C(F)C(OC)=C1 OHCPSBQCCLBHGV-UHFFFAOYSA-N 0.000 claims description 2
• BTBFLTHSGSQXNF-UHFFFAOYSA-N methyl 2-[3-(dimethylamino)-4-methylanilino]-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidine-5-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C(=O)OC)=CN=C1NC1=CC=C(C)C(N(C)C)=C1 BTBFLTHSGSQXNF-UHFFFAOYSA-N 0.000 claims description 2
• KJXXLUHGCDCROD-UHFFFAOYSA-N methyl 2-[3-methoxy-5-(trifluoromethyl)anilino]-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidine-5-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C(=O)OC)=CN=C1NC1=CC(OC)=CC(C(F)(F)F)=C1 KJXXLUHGCDCROD-UHFFFAOYSA-N 0.000 claims description 2
• GLBRHNCVISMDSG-UHFFFAOYSA-N methyl 2-anilino-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidine-5-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C(=O)OC)=CN=C1NC1=CC=CC=C1 GLBRHNCVISMDSG-UHFFFAOYSA-N 0.000 claims description 2
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 15
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 3
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
• 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 1
• XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical compound NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-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
• VRUSPGNUHFUEQI-UHFFFAOYSA-N 3-[[5-fluoro-4-[(7-fluoro-2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(F)C=3)C(F)=CN=2)=C1 VRUSPGNUHFUEQI-UHFFFAOYSA-N 0.000 claims 1
• IANOZUTZODAJSM-UHFFFAOYSA-N 3-methyl-5-[[5-methyl-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-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=C4N(C)C(=O)OC4=CC=3)C(C)=CN=2)=C1 IANOZUTZODAJSM-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
• 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
• LPHCLCMKBSJBDO-UHFFFAOYSA-N 5-[[2-(1,3-dihydro-2-benzofuran-5-ylamino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)NC2=CC(NC2=NC(NC=3C=C4COCC4=CC=3)=NC=C2C)=C1 LPHCLCMKBSJBDO-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
• 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 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
• 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 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
• GTMYMSIHFKBDPV-UHFFFAOYSA-N 5-[[2-(3-methoxy-4,5-dimethylanilino)-5-methylpyrimidin-4-yl]amino]-7-methyl-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(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(C)C=3)C(C)=CN=2)=C1 GTMYMSIHFKBDPV-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
• 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
• 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
• FPXZBGCWCQPXEV-UHFFFAOYSA-N 5-[[2-(4-fluoro-3-methoxy-5-methylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;sulfuric acid Chemical compound OS(O)(=O)=O.CC1=C(F)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 FPXZBGCWCQPXEV-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
• KDJCOZKHECFPBB-UHFFFAOYSA-N 5-[[2-[2-fluoro-3-(2-methoxyethoxy)-4-methylanilino]-5-methylpyrimidin-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(C)=CN=2)=C1F KDJCOZKHECFPBB-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
• 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
• 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
• BEEQJJFPNMIRDP-UHFFFAOYSA-N 5-[[2-[4-[1-(cyclopropylamino)ethyl]anilino]-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.C=1C=C(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)C=CC=1C(C)NC1CC1 BEEQJJFPNMIRDP-UHFFFAOYSA-N 0.000 claims 1
• VPGJITKTYNWGFP-UHFFFAOYSA-N 5-[[5-[(4-methylpiperazin-1-yl)methyl]-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1CN(C)CCN1CC(C(=N1)NC=2C=C3NC(=O)OC3=CC=2)=CN=C1NC1=CC(C)=C(C)C(C)=C1 VPGJITKTYNWGFP-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
• 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 1
• 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 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
• 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 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
• 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 1
• 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 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
• HYSCOLCJYCPNSG-UHFFFAOYSA-N 5-[[5-fluoro-2-(4-methoxyanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.C1=CC(OC)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 HYSCOLCJYCPNSG-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
• KUCUJYUEAZVWMJ-UHFFFAOYSA-N 5-[[5-fluoro-2-[(1-methyl-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C2CCCC(=O)N(C)C2=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 KUCUJYUEAZVWMJ-UHFFFAOYSA-N 0.000 claims 1
• HSMCDWUOVAKZOA-UHFFFAOYSA-N 5-[[5-fluoro-2-[(1-oxo-2,3-dihydro-2-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.C1=CCNC(=O)C=2C1=CC(NC1=NC=C(C(=N1)NC=1C=C3NC(=O)OC3=CC=1)F)=CC=2 HSMCDWUOVAKZOA-UHFFFAOYSA-N 0.000 claims 1
• JFQFNBKGQYGQNQ-UHFFFAOYSA-N 5-[[5-fluoro-2-[(1-oxo-3,4-dihydro-2h-isoquinolin-6-yl)amino]pyrimidin-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=C4CCNC(=O)C4=CC=3)=NC=C2F)=C1 JFQFNBKGQYGQNQ-UHFFFAOYSA-N 0.000 claims 1
• WBIWWVFTJXAWQZ-UHFFFAOYSA-N 5-[[5-fluoro-2-[(2-methyl-1-oxo-3h-2-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.O=C1N(C)CC=CC2=CC(NC=3N=C(NC=4C=C5NC(=O)OC5=CC=4)C(F)=CN=3)=CC=C21 WBIWWVFTJXAWQZ-UHFFFAOYSA-N 0.000 claims 1
• RNZXZERQJNNPBU-UHFFFAOYSA-N 5-[[5-fluoro-2-[(2-oxo-1,3,4,5-tetrahydro-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C(=O)CCCC2=CC(NC3=NC=C(C(=N3)NC=3C=C4NC(=O)OC4=CC=3)F)=CC=C21 RNZXZERQJNNPBU-UHFFFAOYSA-N 0.000 claims 1
• HUVQIFXDUJBESK-UHFFFAOYSA-N 5-[[5-fluoro-2-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)amino]pyrimidin-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=C4CCC(=O)NC4=CC=3)=NC=C2F)=C1 HUVQIFXDUJBESK-UHFFFAOYSA-N 0.000 claims 1
• CWBPCZOPZSAPOY-UHFFFAOYSA-N 5-[[5-fluoro-2-[(5-oxo-6,7,8,9-tetrahydrobenzo[7]annulen-2-yl)amino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.C1CCCC(=O)C=2C1=CC(NC1=NC=C(C(=N1)NC=1C=C3NC(=O)OC3=CC=1)F)=CC=2 CWBPCZOPZSAPOY-UHFFFAOYSA-N 0.000 claims 1
• UDBVOVPVELQKBE-UHFFFAOYSA-N 5-[[5-fluoro-2-[(7-oxo-5,6,8,9-tetrahydrobenzo[7]annulen-3-yl)amino]pyrimidin-4-yl]amino]-3H-1,3-benzoxazol-2-one formic acid Chemical compound OC=O.OC=O.Fc1cnc(Nc2ccc3CCC(=O)CCc3c2)nc1Nc1ccc2oc(=O)[nH]c2c1 UDBVOVPVELQKBE-UHFFFAOYSA-N 0.000 claims 1
• OSQOUTSCKJPZMB-UHFFFAOYSA-N 5-[[5-fluoro-2-[(7-pyrrolidin-1-yl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-3-yl)amino]pyrimidin-4-yl]amino]-3H-1,3-benzoxazol-2-one formic acid Chemical compound OC=O.OC=O.Fc1cnc(Nc2ccc3CCC(CCc3c2)N2CCCC2)nc1Nc1ccc2oc(=O)[nH]c2c1 OSQOUTSCKJPZMB-UHFFFAOYSA-N 0.000 claims 1
• WIZRBYQINNOORW-UHFFFAOYSA-N 5-[[5-fluoro-2-[3-(fluoromethyl)-5-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(CF)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 WIZRBYQINNOORW-UHFFFAOYSA-N 0.000 claims 1
• AMIYKASADLETER-UHFFFAOYSA-N 5-[[5-fluoro-2-[3-fluoro-5-(4-methylpiperazin-1-yl)anilino]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.C1CN(C)CCN1C1=CC(F)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 AMIYKASADLETER-UHFFFAOYSA-N 0.000 claims 1
• KZYVIYYNJZQSKZ-UHFFFAOYSA-N 5-[[5-fluoro-2-[3-methoxy-5-(trifluoromethyl)anilino]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.FC(F)(F)C1=CC(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(C)C=3)C(F)=CN=2)=C1 KZYVIYYNJZQSKZ-UHFFFAOYSA-N 0.000 claims 1
• YZUVBQMPPBKGDU-OLGQORCHSA-N 5-[[5-fluoro-2-[[(4z)-2-methyl-1-oxo-3,6-dihydro-2-benzazocin-9-yl]amino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;formic acid Chemical compound OC=O.C1=C2C(=O)N(C)C\C=C/CC2=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 YZUVBQMPPBKGDU-OLGQORCHSA-N 0.000 claims 1
• MYJJPCQFOUOANK-UHFFFAOYSA-N 5-[[5-methyl-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-7-(piperidin-1-ylmethyl)-3h-1,3-benzoxazol-2-one Chemical compound CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(CN4CCCCC4)C=3)C(C)=CN=2)=C1 MYJJPCQFOUOANK-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• HVXFMODEEXXGSR-UHFFFAOYSA-N 5-[[5-methyl-2-[(1-oxo-3h-2-benzofuran-5-yl)amino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)NC2=CC(NC2=NC(NC=3C=C4COC(=O)C4=CC=3)=NC=C2C)=C1 HVXFMODEEXXGSR-UHFFFAOYSA-N 0.000 claims 1
• HOSGMIPJIISPNQ-UHFFFAOYSA-N 5-[[5-methyl-2-[(3-oxo-1,2-dihydroisoindol-5-yl)amino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)NC2=CC(NC2=NC(NC=3C=C4C(=O)NCC4=CC=3)=NC=C2C)=C1 HOSGMIPJIISPNQ-UHFFFAOYSA-N 0.000 claims 1
• YYWLPIYQOFDPTB-UHFFFAOYSA-N 5-[[5-methyl-2-[(3-oxo-1h-2-benzofuran-5-yl)amino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)NC2=CC(NC2=NC(NC=3C=C4C(=O)OCC4=CC=3)=NC=C2C)=C1 YYWLPIYQOFDPTB-UHFFFAOYSA-N 0.000 claims 1
• DYFCHMMPQXMIMI-UHFFFAOYSA-N 5-[[5-methyl-2-[(7-methyl-1-oxo-3h-2-benzofuran-4-yl)amino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)NC2=CC(NC=2C(C)=CN=C(N=2)NC2=CC=C(C=3C(=O)OCC=32)C)=C1 DYFCHMMPQXMIMI-UHFFFAOYSA-N 0.000 claims 1
• YZJYFHDRGFODCL-UHFFFAOYSA-N 5-[[5-methyl-2-[(7-methyl-3-oxo-1h-2-benzofuran-5-yl)amino]pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)NC2=CC(NC=2C(C)=CN=C(N=2)NC=2C=C(C=3COC(=O)C=3C=2)C)=C1 YZJYFHDRGFODCL-UHFFFAOYSA-N 0.000 claims 1
• ZSJZPVKDVHLLMY-AATRIKPKSA-N 7-[(e)-3-chloroprop-1-enyl]-5-[[5-methyl-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=C(\C=C\CCl)C=3)C(C)=CN=2)=C1 ZSJZPVKDVHLLMY-AATRIKPKSA-N 0.000 claims 1
• ZNHZNSCHDZWEAO-UHFFFAOYSA-N 7-[[5-fluoro-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]-4h-1,4-benzoxazin-3-one;formic acid Chemical compound OC=O.C1=C2OC(=O)NC2=CC(NC2=NC(NC=3C=C4OCC(=O)NC4=CC=3)=NC=C2F)=C1 ZNHZNSCHDZWEAO-UHFFFAOYSA-N 0.000 claims 1
• KMEVTQVOMLOYES-UHFFFAOYSA-N 7-fluoro-5-[[2-(3-methoxy-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(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(F)C=3)C(C)=CN=2)=C1 KMEVTQVOMLOYES-UHFFFAOYSA-N 0.000 claims 1
• FJZFFJAKWGAWTA-UHFFFAOYSA-N 7-fluoro-5-[[5-fluoro-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=C(F)C=3)C(F)=CN=2)=C1 FJZFFJAKWGAWTA-UHFFFAOYSA-N 0.000 claims 1
• WESSJCNTHNGGTB-UHFFFAOYSA-N 7-fluoro-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=C(F)C=3)C(F)=CN=2)=C1 WESSJCNTHNGGTB-UHFFFAOYSA-N 0.000 claims 1
• WEWCWKAJOYGRDO-UHFFFAOYSA-N 7-fluoro-5-[[5-fluoro-2-(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.COC1=CC(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(F)C=3)C(F)=CN=2)=C1 WEWCWKAJOYGRDO-UHFFFAOYSA-N 0.000 claims 1
• YGCUTTDUTLEFBV-UHFFFAOYSA-N 7-fluoro-5-[[5-fluoro-2-(4-fluoro-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=C(F)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(F)C=3)C(F)=CN=2)=C1 YGCUTTDUTLEFBV-UHFFFAOYSA-N 0.000 claims 1
• IGPSEQFSCWPGTM-UHFFFAOYSA-N 7-fluoro-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=C(F)C=3)C(F)=CN=2)=C1 IGPSEQFSCWPGTM-UHFFFAOYSA-N 0.000 claims 1
• OMUNJMWWNCOIJV-UHFFFAOYSA-N 7-fluoro-5-[[5-fluoro-2-(4-methoxy-3-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=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=C(F)C=2)=N1 OMUNJMWWNCOIJV-UHFFFAOYSA-N 0.000 claims 1
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
• 125000005228 aryl sulfonate group Chemical group 0.000 claims 1
• XNZCFHMQDLFWGI-UHFFFAOYSA-N benzenesulfonic acid;5-[[2-(3-methoxy-4,5-dimethylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound OS(=O)(=O)C1=CC=CC=C1.CC1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 XNZCFHMQDLFWGI-UHFFFAOYSA-N 0.000 claims 1
• OEUXVZVZRYDDMX-UHFFFAOYSA-N benzenesulfonic acid;5-[[2-(4-fluoro-3-methoxy-5-methylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound OS(=O)(=O)C1=CC=CC=C1.CC1=C(F)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 OEUXVZVZRYDDMX-UHFFFAOYSA-N 0.000 claims 1
• VUECYGSDPQKPGL-UHFFFAOYSA-N calcium;[5-[[2-(4-fluoro-3-methoxy-5-methylanilino)-5-methylpyrimidin-4-yl]amino]-2-oxo-1,3-benzoxazol-3-yl]methyl dihydrogen phosphate Chemical compound [Ca].CC1=C(F)C(OC)=CC(NC=2N=C(NC=3C=C4N(COP(O)(O)=O)C(=O)OC4=CC=3)C(C)=CN=2)=C1 VUECYGSDPQKPGL-UHFFFAOYSA-N 0.000 claims 1
• ZXWKJDUTEZLFEW-UHFFFAOYSA-L disodium;[5-[[2-(3-methoxy-4,5-dimethylanilino)-5-methylpyrimidin-4-yl]amino]-2-oxo-1,3-benzoxazol-3-yl]methyl phosphate Chemical compound [Na+].[Na+].CC1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4N(COP([O-])([O-])=O)C(=O)OC4=CC=3)C(C)=CN=2)=C1 ZXWKJDUTEZLFEW-UHFFFAOYSA-L 0.000 claims 1
• YEWZQCDRZRYAEB-UHFFFAOYSA-M ditert-butyl phosphate Chemical compound CC(C)(C)OP([O-])(=O)OC(C)(C)C YEWZQCDRZRYAEB-UHFFFAOYSA-M 0.000 claims 1
• RBCYEWAKRACRDC-UHFFFAOYSA-N ethyl 2-methoxy-6-methyl-4-[[5-methyl-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]benzoate Chemical compound C1=C(OC)C(C(=O)OCC)=C(C)C=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 RBCYEWAKRACRDC-UHFFFAOYSA-N 0.000 claims 1
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