JP6552608B2 - ヒストンデメチラーゼ阻害剤 - Google Patents

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Publication number

JP6552608B2

JP6552608B2 JP2017514615A JP2017514615A JP6552608B2 JP 6552608 B2 JP6552608 B2 JP 6552608B2 JP 2017514615 A JP2017514615 A JP 2017514615A JP 2017514615 A JP2017514615 A JP 2017514615A JP 6552608 B2 JP6552608 B2 JP 6552608B2

Authority

JP

Japan

Prior art keywords

pyrimidin

pharmaceutically acceptable

pyrido

acceptable salt

methyl

Prior art date

2014-09-17

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.)

Expired - Fee Related

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• 108010074870 Histone Demethylases Proteins 0.000 title claims description 39
• 102000008157 Histone Demethylases Human genes 0.000 title claims description 39
• 229940122680 Demethylase inhibitor Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 464
• 150000003839 salts Chemical class 0.000 claims description 306
• -1 1,2,3,4-tetrahydronaphthalenyl Chemical group 0.000 claims description 151
• 239000000203 mixture Substances 0.000 claims description 100
• 125000000217 alkyl group Chemical group 0.000 claims description 93
• 125000003118 aryl group Chemical group 0.000 claims description 62
• 229910052736 halogen Inorganic materials 0.000 claims description 53
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 51
• 125000000623 heterocyclic group Chemical group 0.000 claims description 50
• 125000005843 halogen group Chemical group 0.000 claims description 46
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 45
• 125000001072 heteroaryl group Chemical group 0.000 claims description 41
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 28
• 206010028980 Neoplasm Diseases 0.000 claims description 26
• 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 26
• 125000001153 fluoro group Chemical group F* 0.000 claims description 25
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 201000011510 cancer Diseases 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 230000002401 inhibitory effect Effects 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 17
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• QMOPAFMMLWUTKI-UHFFFAOYSA-N 1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1=CC=C2C(O)=NC=NC2=C1 QMOPAFMMLWUTKI-UHFFFAOYSA-N 0.000 claims description 10
• 125000003282 alkyl amino group Chemical group 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 7
• 125000002757 morpholinyl group Chemical group 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• NVRHIDHPBHNKJX-UHFFFAOYSA-N 2-[4-[N-methyl-3-(4-methylpiperazin-1-yl)anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC(=CC=C1)N1CCN(CC1)C NVRHIDHPBHNKJX-UHFFFAOYSA-N 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• NCRVLFZFQTZIPS-UHFFFAOYSA-N 2-[4-(4-cyclopropyl-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(CC1)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C NCRVLFZFQTZIPS-UHFFFAOYSA-N 0.000 claims description 4
• WLMRSZUYFSTETI-UHFFFAOYSA-N 2-[4-(N-methyl-4-morpholin-4-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC=C(C=C1)N1CCOCC1 WLMRSZUYFSTETI-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• AYNNEVPMDRKQCJ-UHFFFAOYSA-N 2-(1-benzylindazol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N1N=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O AYNNEVPMDRKQCJ-UHFFFAOYSA-N 0.000 claims description 3
• WCSLCBLWILXJIQ-UHFFFAOYSA-N 2-(1-benzylindazol-6-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N1N=CC2=CC=C(C=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O WCSLCBLWILXJIQ-UHFFFAOYSA-N 0.000 claims description 3
• BDGGCQQCOJPBLY-UHFFFAOYSA-N 2-(1-benzylindol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O BDGGCQQCOJPBLY-UHFFFAOYSA-N 0.000 claims description 3
• GCMRGFKARWMSAN-UHFFFAOYSA-N 2-(1-benzylindol-6-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O GCMRGFKARWMSAN-UHFFFAOYSA-N 0.000 claims description 3
• XYMCOONDOSQQME-UHFFFAOYSA-N 2-(1-cyclopentylindol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(CCCC1)N1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O XYMCOONDOSQQME-UHFFFAOYSA-N 0.000 claims description 3
• OGJOQXKCDODHAH-UHFFFAOYSA-N 2-(1-methylindol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O OGJOQXKCDODHAH-UHFFFAOYSA-N 0.000 claims description 3
• IJEJFRMSEYJKCB-UHFFFAOYSA-N 2-(2-benzylindazol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N1N=C2C=CC(=CC2=C1)OC=1N=C(C2=C(N=1)C=NC=C2)O IJEJFRMSEYJKCB-UHFFFAOYSA-N 0.000 claims description 3
• BBDTWEHTHUQEHL-UHFFFAOYSA-N 2-(2-benzylindazol-6-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N1N=C2C=C(C=CC2=C1)OC=1N=C(C2=C(N=1)C=NC=C2)O BBDTWEHTHUQEHL-UHFFFAOYSA-N 0.000 claims description 3
• UQBJLMBNRBGNMX-UHFFFAOYSA-N 2-[(1-phenyl-2,3-dihydroindol-5-yl)oxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)N1CCC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O UQBJLMBNRBGNMX-UHFFFAOYSA-N 0.000 claims description 3
• UOHPJYFCEUANGX-UHFFFAOYSA-N 2-[(1-phenyl-3,4-dihydro-2H-quinolin-6-yl)oxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)N1CCCC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O UOHPJYFCEUANGX-UHFFFAOYSA-N 0.000 claims description 3
• VLHMINSNLNRQMU-UHFFFAOYSA-N 2-[1-(2-phenylethyl)indol-5-yl]oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(CC1=CC=CC=C1)N1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O VLHMINSNLNRQMU-UHFFFAOYSA-N 0.000 claims description 3
• YDTRYKRNDCZZPP-UHFFFAOYSA-N 2-[3-(N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C=1C=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=CC=1)C1=CC=CC=C1 YDTRYKRNDCZZPP-UHFFFAOYSA-N 0.000 claims description 3
• ILUHNCDZOBKFNT-UHFFFAOYSA-N 2-[3-[benzyl(methyl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N(C=1C=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=CC=1)C ILUHNCDZOBKFNT-UHFFFAOYSA-N 0.000 claims description 3
• YKNIDCVIHXRDHC-UHFFFAOYSA-N 2-[3-fluoro-4-(N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound FC=1C=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=CC=1N(C1=CC=CC=C1)C YKNIDCVIHXRDHC-UHFFFAOYSA-N 0.000 claims description 3
• XIBIGJJNITZXIB-UHFFFAOYSA-N 2-[4-(2-phenylmorpholin-4-yl)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)C1CN(CCO1)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 XIBIGJJNITZXIB-UHFFFAOYSA-N 0.000 claims description 3
• COBYQVQJCZYEBC-UHFFFAOYSA-N 2-[4-(3-methoxy-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COC=1C=C(C=CC=1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C COBYQVQJCZYEBC-UHFFFAOYSA-N 0.000 claims description 3
• KSZDGLQJEJYGMA-UHFFFAOYSA-N 2-[4-(3-phenylpiperidin-1-yl)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)C1CN(CCC1)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 KSZDGLQJEJYGMA-UHFFFAOYSA-N 0.000 claims description 3
• RQZSATFWCBCUIO-UHFFFAOYSA-N 2-[4-(4-methoxy-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C RQZSATFWCBCUIO-UHFFFAOYSA-N 0.000 claims description 3
• MSRPQWORNNWNAO-UHFFFAOYSA-N 2-[4-(N,4-dimethylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC=C(C=C1)C MSRPQWORNNWNAO-UHFFFAOYSA-N 0.000 claims description 3
• FXOZDODFBPBHLG-UHFFFAOYSA-N 2-[4-(N-ethyl-4-propan-2-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC=C(C=C1)C(C)C FXOZDODFBPBHLG-UHFFFAOYSA-N 0.000 claims description 3
• GVFNCHSPHFHNSD-UHFFFAOYSA-N 2-[4-(N-methyl-3-morpholin-4-yl-4-propan-2-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)(C)C1=C(C=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C)N1CCOCC1 GVFNCHSPHFHNSD-UHFFFAOYSA-N 0.000 claims description 3
• WBUXXLSZHBPOSW-UHFFFAOYSA-N 2-[4-(N-methyl-3-morpholin-4-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC(=CC=C1)N1CCOCC1 WBUXXLSZHBPOSW-UHFFFAOYSA-N 0.000 claims description 3
• YELYEKBMSXCDGL-UHFFFAOYSA-N 2-[4-(N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC=CC=C1 YELYEKBMSXCDGL-UHFFFAOYSA-N 0.000 claims description 3
• NZCOKNORNALEMH-UHFFFAOYSA-N 2-[4-[4-(1-aminopropan-2-yl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound NCC(C)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C NZCOKNORNALEMH-UHFFFAOYSA-N 0.000 claims description 3
• IDWQEMVQZNXZTI-UHFFFAOYSA-N 2-[4-[4-(1-cyclopropylethyl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(CC1)C(C)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C IDWQEMVQZNXZTI-UHFFFAOYSA-N 0.000 claims description 3
• BPAPEWQJFYHACY-UHFFFAOYSA-N 2-[4-[4-(1-methoxyethyl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COC(C)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C BPAPEWQJFYHACY-UHFFFAOYSA-N 0.000 claims description 3
• RCKIYJJKTLSRJU-UHFFFAOYSA-N 2-[4-[4-(1-methoxypropan-2-yl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COCC(C)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C RCKIYJJKTLSRJU-UHFFFAOYSA-N 0.000 claims description 3
• AGYQLVALDYCWPB-UHFFFAOYSA-N 2-[4-[4-(4-aminopiperidin-1-yl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound NC1CCN(CC1)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C AGYQLVALDYCWPB-UHFFFAOYSA-N 0.000 claims description 3
• VAYGMXWSYWYQSI-UHFFFAOYSA-N 2-[4-[4-[4-(dimethylamino)butan-2-yl]-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(CCC(C)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C)C VAYGMXWSYWYQSI-UHFFFAOYSA-N 0.000 claims description 3
• PCTBZMTVWLMJTL-UHFFFAOYSA-N 2-[4-[4-propan-2-yl-N-(2,2,2-trifluoroethyl)anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)(C)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)CC(F)(F)F PCTBZMTVWLMJTL-UHFFFAOYSA-N 0.000 claims description 3
• HIEXVOBPEWWGJY-UHFFFAOYSA-N 2-[4-[N-methyl-3-[(4-methylpiperazin-1-yl)methyl]anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC(=CC=C1)CN1CCN(CC1)C HIEXVOBPEWWGJY-UHFFFAOYSA-N 0.000 claims description 3
• CNQMUOQMQVAVEI-UHFFFAOYSA-N 2-[4-[benzyl(methyl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C CNQMUOQMQVAVEI-UHFFFAOYSA-N 0.000 claims description 3
• VJRRSIKXEUZPHL-UHFFFAOYSA-N 2-[4-[methyl(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)CC1CCCC2=CC=CC=C12 VJRRSIKXEUZPHL-UHFFFAOYSA-N 0.000 claims description 3
• VXWMVXOIQLLKMN-UHFFFAOYSA-N 2-[4-[methyl(2-phenylethyl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)CCC1=CC=CC=C1 VXWMVXOIQLLKMN-UHFFFAOYSA-N 0.000 claims description 3
• VKDUSQPGXRXKMN-UHFFFAOYSA-N 2-[4-[methyl(pyridin-2-yl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=NC=CC=C1 VKDUSQPGXRXKMN-UHFFFAOYSA-N 0.000 claims description 3
• LOXXKWYLDXNARO-UHFFFAOYSA-N 2-[4-[methyl-(5-morpholin-4-ylpyridin-3-yl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C=1C=NC=C(C=1)N1CCOCC1 LOXXKWYLDXNARO-UHFFFAOYSA-N 0.000 claims description 3
• XKBXFTPKURQNCU-UHFFFAOYSA-N 2-[4-[methyl-(5-propan-2-ylpyridin-2-yl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)(C)C=1C=CC(=NC=1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C XKBXFTPKURQNCU-UHFFFAOYSA-N 0.000 claims description 3
• QUZXIZKHOQCCRY-UHFFFAOYSA-N 3-[4-[N-methyl-4-[(4-oxo-3H-pyrido[3,4-d]pyrimidin-2-yl)oxy]anilino]phenyl]butanenitrile Chemical compound OC=1C2=C(N=C(N=1)OC1=CC=C(C=C1)N(C1=CC=C(C=C1)C(CC#N)C)C)C=NC=C2 QUZXIZKHOQCCRY-UHFFFAOYSA-N 0.000 claims description 3
• BWUXABKTZMTAQE-UHFFFAOYSA-N 3-[N-methyl-4-[(4-oxo-3H-pyrido[3,4-d]pyrimidin-2-yl)oxy]anilino]benzonitrile Chemical compound OC=1C2=C(N=C(N=1)OC1=CC=C(C=C1)N(C=1C=C(C#N)C=CC=1)C)C=NC=C2 BWUXABKTZMTAQE-UHFFFAOYSA-N 0.000 claims description 3
• VEMHOQINGBWINF-UHFFFAOYSA-N N-methyl-N-[4-[(4-oxo-3H-pyrido[3,4-d]pyrimidin-2-yl)oxy]phenyl]-2-phenylacetamide Chemical compound OC=1C2=C(N=C(N=1)OC1=CC=C(C=C1)N(C(CC1=CC=CC=C1)=O)C)C=NC=C2 VEMHOQINGBWINF-UHFFFAOYSA-N 0.000 claims description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
• DOBZVGBVNPHCFT-UHFFFAOYSA-N 2-(1-phenylindol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)N1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O DOBZVGBVNPHCFT-UHFFFAOYSA-N 0.000 claims description 2
• AVPBNCDXCUBCFD-UHFFFAOYSA-N 2-(1-piperidin-4-ylindol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1CCC(CC1)N1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O AVPBNCDXCUBCFD-UHFFFAOYSA-N 0.000 claims description 2
• LPQYVJZVLPGAOE-UHFFFAOYSA-N 2-[1-(oxan-4-yl)indol-5-yl]oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound O1CCC(CC1)N1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O LPQYVJZVLPGAOE-UHFFFAOYSA-N 0.000 claims description 2
• GGHUFCYASQYURN-UHFFFAOYSA-N 2-[4-(2-fluoro-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC2=NC3=CN=CC=C3C(O)=N2)C=C1)C1=CC=CC=C1F GGHUFCYASQYURN-UHFFFAOYSA-N 0.000 claims description 2
• WPXNVAPMYMQGFE-UHFFFAOYSA-N 2-[4-(3-chloro-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound ClC=1C=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=CC=1 WPXNVAPMYMQGFE-UHFFFAOYSA-N 0.000 claims description 2
• KPJXVEMQMLXZMH-UHFFFAOYSA-N 2-[4-(3-fluoro-N,4-dimethylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound FC=1C=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=CC=1C KPJXVEMQMLXZMH-UHFFFAOYSA-N 0.000 claims description 2
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• YUXHMEBKBLTENB-UHFFFAOYSA-N 2-[4-(N,4-dimethyl-3-morpholin-4-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC(=C(C=C1)C)N1CCOCC1)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 YUXHMEBKBLTENB-UHFFFAOYSA-N 0.000 claims description 2
• ZKEGBXDAIMDIEU-UHFFFAOYSA-N 2-[4-(N-cyclobutyl-4-propan-2-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(CCC1)N(C1=CC=C(C=C1)C(C)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 ZKEGBXDAIMDIEU-UHFFFAOYSA-N 0.000 claims description 2
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• KPGKMXVEAKUCQD-UHFFFAOYSA-N 2-[4-(N-methyl-4-pyrrolidin-1-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(C=C1)N1CCCC1)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 KPGKMXVEAKUCQD-UHFFFAOYSA-N 0.000 claims description 2
• MOGTYGUBYMTHOM-UHFFFAOYSA-N 2-[4-[(3,3-dimethyl-2H-1-benzofuran-6-yl)-methylamino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC2=NC3=CN=CC=C3C(O)=N2)C=C1)C1=CC=C2C(OCC2(C)C)=C1 MOGTYGUBYMTHOM-UHFFFAOYSA-N 0.000 claims description 2
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• XYLNOUNFHNFTKV-UHFFFAOYSA-N 2-[4-[2,3-dihydro-1H-inden-1-ylmethyl(methyl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(CCC2=CC=CC=C12)CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C XYLNOUNFHNFTKV-UHFFFAOYSA-N 0.000 claims description 2
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• GDOMYKIRVKAYCH-UHFFFAOYSA-N 2-[4-[N-methyl-4-(4-methylpiperazin-1-yl)anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(C=C1)N1CCN(CC1)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 GDOMYKIRVKAYCH-UHFFFAOYSA-N 0.000 claims description 2
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