KR20170048591A - 히스톤 데메틸라제 억제제 - Google Patents

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Publication number

KR20170048591A

KR20170048591A KR1020177009917A KR20177009917A KR20170048591A KR 20170048591 A KR20170048591 A KR 20170048591A KR 1020177009917 A KR1020177009917 A KR 1020177009917A KR 20177009917 A KR20177009917 A KR 20177009917A KR 20170048591 A KR20170048591 A KR 20170048591A

Authority

KR

South Korea

Prior art keywords

pyrimidin

pyrido

pharmaceutically acceptable

phenoxy

acceptable salt

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.)

Withdrawn

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• 108010074870 Histone Demethylases Proteins 0.000 title claims abstract description 42
• 102000008157 Histone Demethylases Human genes 0.000 title claims abstract description 42
• 239000003112 inhibitor Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 419
• -1 pyrido [3,4-d] pyrimidin-4-one derivative compounds Chemical class 0.000 claims abstract description 208
• 238000000034 method Methods 0.000 claims abstract description 127
• 239000000203 mixture Substances 0.000 claims abstract description 103
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 28
• 201000011510 cancer Diseases 0.000 claims abstract description 19
• 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 18
• 238000011282 treatment Methods 0.000 claims abstract description 8
• 150000003839 salts Chemical class 0.000 claims description 291
• 125000000217 alkyl group Chemical group 0.000 claims description 116
• 125000003118 aryl group Chemical group 0.000 claims description 53
• 229910052736 halogen Inorganic materials 0.000 claims description 53
• 125000000623 heterocyclic group Chemical group 0.000 claims description 53
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 51
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 47
• 125000005843 halogen group Chemical group 0.000 claims description 46
• 125000001072 heteroaryl group Chemical group 0.000 claims description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• 239000001257 hydrogen Substances 0.000 claims description 28
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
• 125000001153 fluoro group Chemical group F* 0.000 claims description 25
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 21
• 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 17
• 230000002401 inhibitory effect Effects 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 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 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 125000002757 morpholinyl group Chemical group 0.000 claims description 7
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
• 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 4
• 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
• 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
• 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
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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
• 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 2
• 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 2
• 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 2
• 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 2
• 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 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
• 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 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
• 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 2
• 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 2
• GVRPQGJEOVBHLR-UHFFFAOYSA-N 2-[4-(3-phenylpyrrolidin-1-yl)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)C1CN(CC1)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 GVRPQGJEOVBHLR-UHFFFAOYSA-N 0.000 claims description 2
• GLOALBZJXBQZTJ-UHFFFAOYSA-N 2-[4-(4-chloro-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound ClC1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 GLOALBZJXBQZTJ-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• QMWFMZMUWRTMPB-UHFFFAOYSA-N 2-[4-(4-ethyl-N-methyl-3-morpholin-4-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)C1=C(C=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1)N1CCOCC1 QMWFMZMUWRTMPB-UHFFFAOYSA-N 0.000 claims description 2
• JXJFONPGIZCSTF-UHFFFAOYSA-N 2-[4-(4-ethyl-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)C1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 JXJFONPGIZCSTF-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• CHULWJUZMOFOBC-UHFFFAOYSA-N 2-[4-(4-tert-butyl-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)(C)(C)C1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 CHULWJUZMOFOBC-UHFFFAOYSA-N 0.000 claims description 2
• LEEOBDATXTXUKR-UHFFFAOYSA-N 2-[4-(N,3,4-trimethylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC(=C(C=C1)C)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 LEEOBDATXTXUKR-UHFFFAOYSA-N 0.000 claims description 2
• 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
• 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 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
• 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 2
• XDORTSWZPDOCSE-UHFFFAOYSA-N 2-[4-(N-ethylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)N(C1=CC=CC=C1)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 XDORTSWZPDOCSE-UHFFFAOYSA-N 0.000 claims description 2
• PSGWDEAVBFDQLD-UHFFFAOYSA-N 2-[4-(N-methyl-3-methylsulfonylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC(=CC=C1)S(=O)(=O)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 PSGWDEAVBFDQLD-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• BHGRKCHJTFKAPL-UHFFFAOYSA-N 2-[4-(N-methyl-3-propan-2-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC(=CC=C1)C(C)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 BHGRKCHJTFKAPL-UHFFFAOYSA-N 0.000 claims description 2
• ZRCRZJGBZXETMH-UHFFFAOYSA-N 2-[4-(N-methyl-3-pyrrolidin-1-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC(=CC=C1)N1CCCC1)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 ZRCRZJGBZXETMH-UHFFFAOYSA-N 0.000 claims description 2
• LLNLCLYUPDJSFW-UHFFFAOYSA-N 2-[4-(N-methyl-4-methylsulfonylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(C=C1)S(=O)(=O)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 LLNLCLYUPDJSFW-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• HRHSEEODZSBZOP-UHFFFAOYSA-N 2-[4-(N-methyl-4-propan-2-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(C=C1)C(C)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 HRHSEEODZSBZOP-UHFFFAOYSA-N 0.000 claims description 2
• KZLLBEZKGUJSLV-UHFFFAOYSA-N 2-[4-(N-methyl-4-propan-2-yloxyanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(C=C1)OC(C)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 KZLLBEZKGUJSLV-UHFFFAOYSA-N 0.000 claims description 2
• GGXXSZTWMNHYEJ-UHFFFAOYSA-N 2-[4-(N-methyl-4-propylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(C=C1)CCC)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 GGXXSZTWMNHYEJ-UHFFFAOYSA-N 0.000 claims description 2
• 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
• 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 2
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• QDYGQMNZDDXSGV-UHFFFAOYSA-N 2-[4-[3-(dimethylamino)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C=1C=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=CC=1)C QDYGQMNZDDXSGV-UHFFFAOYSA-N 0.000 claims description 2
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