JP2013528595A5 - - Google Patents
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- JP2013528595A5 JP2013528595A5 JP2013509305A JP2013509305A JP2013528595A5 JP 2013528595 A5 JP2013528595 A5 JP 2013528595A5 JP 2013509305 A JP2013509305 A JP 2013509305A JP 2013509305 A JP2013509305 A JP 2013509305A JP 2013528595 A5 JP2013528595 A5 JP 2013528595A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxo
- ylamino
- pyridin
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 2- (1-oxo-3,4,6,7,8,9-hexahydropyrido [3,4-b] indolizine-2 (1H) -yl) -6- (4 , 4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl) benzyl Chemical group 0.000 description 72
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 38
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyloxyacetoaldehyde Natural products CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 37
- 229940007550 benzyl acetate Drugs 0.000 description 31
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 28
- 239000007787 solid Substances 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- LLAFSBLYRARBBH-UHFFFAOYSA-N 5-bromo-1-methyl-3-[[5-[4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]pyridin-2-one Chemical compound O=C1N(C)C=C(Br)C=C1NC1=CC=C(N2CCN(CC2)C2COC2)C=N1 LLAFSBLYRARBBH-UHFFFAOYSA-N 0.000 description 3
- NQUTZBLSWYZMAC-UHFFFAOYSA-N 5-bromo-3-[[5-(hydroxymethyl)pyridin-2-yl]amino]-1-methylpyridin-2-one Chemical compound O=C1N(C)C=C(Br)C=C1NC1=CC=C(CO)C=N1 NQUTZBLSWYZMAC-UHFFFAOYSA-N 0.000 description 3
- 102100025137 Early activation antigen CD69 Human genes 0.000 description 3
- 101000934374 Homo sapiens Early activation antigen CD69 Proteins 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002953 preparative HPLC Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GETBAUBPUHGATN-UHFFFAOYSA-N 2-[2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1-one Chemical compound C1=CC=C(N2C(C3=CC=4CCCCC=4N3CC2)=O)C(C)=C1B1OC(C)(C)C(C)(C)O1 GETBAUBPUHGATN-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- BPZRYDSLDUBKLD-UHFFFAOYSA-N 3-chloro-5-[(5-methyl-6,7-dihydro-4h-pyrazolo[1,5-a]pyrazin-2-yl)amino]-1h-pyridazin-6-one Chemical compound C1=C2CN(C)CCN2N=C1NC1=CC(Cl)=NNC1=O BPZRYDSLDUBKLD-UHFFFAOYSA-N 0.000 description 2
- RXULLQCHITUUFS-UHFFFAOYSA-N 5,5-dimethyl-4,6-dihydrocyclopenta[b]thiophene-2-carboxylic acid Chemical compound C1=C(C(O)=O)SC2=C1CC(C)(C)C2 RXULLQCHITUUFS-UHFFFAOYSA-N 0.000 description 2
- PWWBNXXNEUXNKW-UHFFFAOYSA-N 6,6-dimethyl-1,2,5,7-tetrahydrodicyclopenta[3,1-a:3',2'-d]thiophen-3-one Chemical compound O=C1CCC2=C1SC1=C2CC(C)(C)C1 PWWBNXXNEUXNKW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000004159 blood analysis Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
- CCMZSBCQYGJFPI-UHFFFAOYSA-N ethyl 1-(2-aminoethyl)-4,5,6,7-tetrahydroindole-2-carboxylate Chemical compound C1CCCC2=C1C=C(C(=O)OCC)N2CCN CCMZSBCQYGJFPI-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- GTUGJXYPIUJIIH-UHFFFAOYSA-N 1,2,5,6,7,8-hexahydrocyclopenta[b][1]benzothiol-3-one Chemical compound C1CCCC2=C1C(CCC1=O)=C1S2 GTUGJXYPIUJIIH-UHFFFAOYSA-N 0.000 description 1
- IFPMZBBHBZQTOV-UHFFFAOYSA-N 1,3,5-trinitro-2-(2,4,6-trinitrophenyl)-4-[2,4,6-trinitro-3-(2,4,6-trinitrophenyl)phenyl]benzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C=2C(=C(C=3C(=CC(=CC=3[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)C(=CC=2[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)=C1[N+]([O-])=O IFPMZBBHBZQTOV-UHFFFAOYSA-N 0.000 description 1
- SDRFVMSRWNLLPY-UHFFFAOYSA-N 1-(2-amino-6,7-dihydro-4h-pyrazolo[1,5-a]pyrazin-5-yl)ethanone Chemical compound C1N(C(=O)C)CCN2N=C(N)C=C21 SDRFVMSRWNLLPY-UHFFFAOYSA-N 0.000 description 1
- PUDTYWHXPVNAAK-UHFFFAOYSA-N 1-(2-nitro-6,7-dihydro-4h-pyrazolo[1,5-a]pyrazin-5-yl)ethanone Chemical compound C1N(C(=O)C)CCN2N=C([N+]([O-])=O)C=C21 PUDTYWHXPVNAAK-UHFFFAOYSA-N 0.000 description 1
- APRJBQHMWFCVLV-UHFFFAOYSA-N 1-(6-aminopyridin-3-yl)azetidin-3-ol Chemical compound C1=NC(N)=CC=C1N1CC(O)C1 APRJBQHMWFCVLV-UHFFFAOYSA-N 0.000 description 1
- DMCQIHOQXHPIGF-UHFFFAOYSA-N 1-(6-nitropyridin-3-yl)azetidin-3-ol Chemical compound C1C(O)CN1C1=CC=C([N+]([O-])=O)N=C1 DMCQIHOQXHPIGF-UHFFFAOYSA-N 0.000 description 1
- HSFQRBCNMTWGGA-UHFFFAOYSA-N 1-cyclopropyl-3-nitropyrazole Chemical compound N1=C([N+](=O)[O-])C=CN1C1CC1 HSFQRBCNMTWGGA-UHFFFAOYSA-N 0.000 description 1
- STMPPAXSPFYJIM-UHFFFAOYSA-N 1-cyclopropylpyrazol-3-amine Chemical compound N1=C(N)C=CN1C1CC1 STMPPAXSPFYJIM-UHFFFAOYSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- AWWVMSHRMDPPCV-UHFFFAOYSA-N 1-methyl-3-(pyrimidin-4-ylamino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one Chemical compound O=C1N(C)C=C(B2OC(C)(C)C(C)(C)O2)C=C1NC1=CC=NC=N1 AWWVMSHRMDPPCV-UHFFFAOYSA-N 0.000 description 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 1
- NNFGBZPUPIKCAT-UHFFFAOYSA-N 2,2,2-trichloro-1-(4,5,6,7-tetrahydro-1h-indol-2-yl)ethanone Chemical compound C1CCCC2=C1C=C(C(=O)C(Cl)(Cl)Cl)N2 NNFGBZPUPIKCAT-UHFFFAOYSA-N 0.000 description 1
- TVDMPQXVNSYDLI-UHFFFAOYSA-N 2-(3-bromo-2-methylphenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1-one Chemical compound CC1=C(Br)C=CC=C1N1C(=O)C2=CC(CCCC3)=C3N2CC1 TVDMPQXVNSYDLI-UHFFFAOYSA-N 0.000 description 1
- ZLQRJCPSFOIWAD-UHFFFAOYSA-N 2-(3-bromo-2-methylphenyl)-3,4-dihydropyrazino[1,2-a]indol-1-one Chemical compound CC1=C(Br)C=CC=C1N1C(=O)C2=CC3=CC=CC=C3N2CC1 ZLQRJCPSFOIWAD-UHFFFAOYSA-N 0.000 description 1
- ZUIVDEOQMZTGIX-UHFFFAOYSA-N 2-(3-nitropyrazol-1-yl)ethanamine Chemical compound NCCN1C=CC([N+]([O-])=O)=N1 ZUIVDEOQMZTGIX-UHFFFAOYSA-N 0.000 description 1
- KAGPWRFUPZWOQR-UHFFFAOYSA-N 2-[2-(3-nitropyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound N1=C([N+](=O)[O-])C=CN1CCN1C(=O)C2=CC=CC=C2C1=O KAGPWRFUPZWOQR-UHFFFAOYSA-N 0.000 description 1
- ZKOJUMGOQCYDLQ-UHFFFAOYSA-N 2-[2-(hydroxymethyl)-3-[1-methyl-5-[(5-morpholin-4-ylpyridin-2-yl)amino]-6-oxopyridin-3-yl]phenyl]-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1-one Chemical compound O=C1N(C)C=C(C=2C(=C(N3C(C4=CC=5CCCCC=5N4CC3)=O)C=CC=2)CO)C=C1NC(N=C1)=CC=C1N1CCOCC1 ZKOJUMGOQCYDLQ-UHFFFAOYSA-N 0.000 description 1
- YGJCUJMTRWOQLU-UHFFFAOYSA-N 2-[2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3,4-dihydropyrazino[1,2-a]indol-1-one Chemical compound C1=CC=C(N2C(C=3N(C4=CC=CC=C4C=3)CC2)=O)C(C)=C1B1OC(C)(C)C(C)(C)O1 YGJCUJMTRWOQLU-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- JSYAQLZSGHPSJD-UHFFFAOYSA-N 3,3-dimethylcyclopentan-1-one Chemical compound CC1(C)CCC(=O)C1 JSYAQLZSGHPSJD-UHFFFAOYSA-N 0.000 description 1
- PYBZOKKIIZKLSV-UHFFFAOYSA-N 3,4,5,6,7,8-hexahydro-2h-[1]benzothiolo[2,3-c]pyridin-1-one Chemical compound C1CCCC2=C1C(CCNC1=O)=C1S2 PYBZOKKIIZKLSV-UHFFFAOYSA-N 0.000 description 1
- BNXCMQVRHKYDAX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2h-pyrido[3,4-b]indolizin-1-one Chemical compound C1=C2CCCCN2C2=C1C(=O)NCC2 BNXCMQVRHKYDAX-UHFFFAOYSA-N 0.000 description 1
- KRRWBFJXTNMYOZ-UHFFFAOYSA-N 3,4-dihydro-2h-pyrazino[1,2-a]indol-1-one Chemical compound C1=CC=C2N3CCNC(=O)C3=CC2=C1 KRRWBFJXTNMYOZ-UHFFFAOYSA-N 0.000 description 1
- LNVJQIHAUHVGEV-UHFFFAOYSA-N 3,5-dibromo-1-methylpyrazin-2-one Chemical compound CN1C=C(Br)N=C(Br)C1=O LNVJQIHAUHVGEV-UHFFFAOYSA-N 0.000 description 1
- AOJAJTJZSBVNPU-UHFFFAOYSA-N 3,5-dibromo-1-methylpyridin-2-one Chemical compound CN1C=C(Br)C=C(Br)C1=O AOJAJTJZSBVNPU-UHFFFAOYSA-N 0.000 description 1
- XOTZUPSSMGMVLB-UHFFFAOYSA-N 3-[(1,5-dimethylpyrazol-3-yl)amino]-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one Chemical compound CN1C(C)=CC(NC=2C(N(C)C=C(C=2)B2OC(C)(C)C(C)(C)O2)=O)=N1 XOTZUPSSMGMVLB-UHFFFAOYSA-N 0.000 description 1
- XFELGOWJIGMTJD-UHFFFAOYSA-N 3-[(5-acetyl-6,7-dihydro-4h-pyrazolo[1,5-a]pyrazin-2-yl)amino]-5-bromo-1-methylpyridin-2-one Chemical compound C1=C2CN(C(=O)C)CCN2N=C1NC1=CC(Br)=CN(C)C1=O XFELGOWJIGMTJD-UHFFFAOYSA-N 0.000 description 1
- WDXJWQVKAWNBLO-UHFFFAOYSA-N 3-[[5-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl)pyridin-2-yl]amino]-1-methylpyridin-2-one Chemical compound C1N(CC2C1CNC2)C=1C=CC(=NC=1)NC=1C(N(C=CC=1)C)=O WDXJWQVKAWNBLO-UHFFFAOYSA-N 0.000 description 1
- MJZRBOOLNAVMCD-UHFFFAOYSA-N 3-[[5-(azetidin-3-yl)pyridin-2-yl]amino]-5-bromo-1-methylpyridin-2-one Chemical compound O=C1N(C)C=C(Br)C=C1NC1=CC=C(C2CNC2)C=N1 MJZRBOOLNAVMCD-UHFFFAOYSA-N 0.000 description 1
- VJNCMJYHLJHIAB-UHFFFAOYSA-N 3-[[5-[2-(dimethylamino)ethyl-methylamino]pyridin-2-yl]amino]-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one Chemical compound N1=CC(N(C)CCN(C)C)=CC=C1NC1=CC(B2OC(C)(C)C(C)(C)O2)=CN(C)C1=O VJNCMJYHLJHIAB-UHFFFAOYSA-N 0.000 description 1
- CRHMGYDPTGWUAB-UHFFFAOYSA-N 3-chloro-1-(4,5,6,7-tetrahydro-1-benzothiophen-2-yl)propan-1-one Chemical compound C1CCCC2=C1C=C(C(=O)CCCl)S2 CRHMGYDPTGWUAB-UHFFFAOYSA-N 0.000 description 1
- LWTOCVPMOQGEPT-UHFFFAOYSA-N 3-chloro-1-(5,5-dimethyl-4,6-dihydrocyclopenta[b]thiophen-2-yl)propan-1-one Chemical compound C1=C(C(=O)CCCl)SC2=C1CC(C)(C)C2 LWTOCVPMOQGEPT-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- OKLIEGCIVWTOOG-UHFFFAOYSA-N 5-(3-methylazetidin-1-yl)pyridin-2-amine Chemical compound C1C(C)CN1C1=CC=C(N)N=C1 OKLIEGCIVWTOOG-UHFFFAOYSA-N 0.000 description 1
- SXYAZAKTHNMXDO-UHFFFAOYSA-N 5-bromo-1-methyl-3-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)pyrazin-2-one Chemical compound O=C1N(C)C=C(Br)N=C1NC1=CC=C(CNCC2)C2=C1 SXYAZAKTHNMXDO-UHFFFAOYSA-N 0.000 description 1
- QOUXBOVRJMECBY-UHFFFAOYSA-N 5-bromo-1-methyl-3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridin-2-one Chemical compound O=C1N(C)C=C(Br)C=C1NC1=NN2CCNCC2=C1 QOUXBOVRJMECBY-UHFFFAOYSA-N 0.000 description 1
- WZOBUZVEDGWKQO-UHFFFAOYSA-N 5-bromo-1-methyl-3-(4-piperazin-1-ylanilino)pyrazin-2-one Chemical compound O=C1N(C)C=C(Br)N=C1NC1=CC=C(N2CCNCC2)C=C1 WZOBUZVEDGWKQO-UHFFFAOYSA-N 0.000 description 1
- KSMAGFGRTLPTFE-UHFFFAOYSA-N 5-bromo-1-methyl-3-(pyrimidin-4-ylamino)pyridin-2-one Chemical compound O=C1N(C)C=C(Br)C=C1NC1=CC=NC=N1 KSMAGFGRTLPTFE-UHFFFAOYSA-N 0.000 description 1
- IGQYTTAQKUJOJS-UHFFFAOYSA-N 5-bromo-1-methyl-3-[(2-methyl-3,4-dihydro-1h-isoquinolin-6-yl)amino]pyridin-2-one Chemical compound C=1C=C2CN(C)CCC2=CC=1NC1=CC(Br)=CN(C)C1=O IGQYTTAQKUJOJS-UHFFFAOYSA-N 0.000 description 1
- GBWOALMVIWGORY-UHFFFAOYSA-N 5-bromo-1-methyl-3-[(5-methyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)amino]pyridin-2-one Chemical compound S1C=2CN(C)CCC=2N=C1NC1=CC(Br)=CN(C)C1=O GBWOALMVIWGORY-UHFFFAOYSA-N 0.000 description 1
- DBVDTDKSUZISME-UHFFFAOYSA-N 5-bromo-1-methyl-3-[(5-piperazin-1-ylpyridin-2-yl)amino]pyridin-2-one Chemical compound O=C1N(C)C=C(Br)C=C1NC1=CC=C(N2CCNCC2)C=N1 DBVDTDKSUZISME-UHFFFAOYSA-N 0.000 description 1
- AUBFHHIXSVGTMN-UHFFFAOYSA-N 5-bromo-1-methyl-3-[4-[4-(oxetan-3-yl)piperazin-1-yl]anilino]pyrazin-2-one Chemical compound O=C1N(C)C=C(Br)N=C1NC1=CC=C(N2CCN(CC2)C2COC2)C=C1 AUBFHHIXSVGTMN-UHFFFAOYSA-N 0.000 description 1
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