CA2961610A1 - Histone demethylase inhibitors - Google Patents

Info

Publication number

CA2961610A1

CA2961610A1 CA2961610A CA2961610A CA2961610A1 CA 2961610 A1 CA2961610 A1 CA 2961610A1 CA 2961610 A CA2961610 A CA 2961610A CA 2961610 A CA2961610 A CA 2961610A CA 2961610 A1 CA2961610 A1 CA 2961610A1

Authority

CA

Canada

Prior art keywords

pyrimidin

pyrido

compound

pharmaceutically acceptable

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 108010074870 Histone Demethylases Proteins 0.000 title claims abstract description 41
• 102000008157 Histone Demethylases Human genes 0.000 title claims abstract description 41
• 239000003112 inhibitor Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 459
• 238000000034 method Methods 0.000 claims abstract description 222
• -1 pyrido[3,4-d]pyrimidin-4-one derivative compounds Chemical class 0.000 claims abstract description 170
• 239000000203 mixture Substances 0.000 claims abstract description 111
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 29
• 201000011510 cancer Diseases 0.000 claims abstract description 21
• 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 18
• 150000003839 salts Chemical class 0.000 claims description 295
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 164
• 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 120
• 125000000217 alkyl group Chemical group 0.000 claims description 73
• 125000003118 aryl group Chemical group 0.000 claims description 61
• 229910052736 halogen Inorganic materials 0.000 claims description 53
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 52
• 125000000623 heterocyclic group Chemical group 0.000 claims description 51
• 125000005843 halogen group Chemical group 0.000 claims description 46
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 43
• 125000001072 heteroaryl group Chemical group 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 31
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 28
• 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
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 230000002401 inhibitory effect Effects 0.000 claims description 18
• 150000002367 halogens Chemical class 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 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 125000003282 alkyl amino group Chemical group 0.000 claims description 10
• 125000006273 (C1-C3) alkyl group Chemical group 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
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 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 4
• 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 4
• 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 4
• AFHPEJCZXXGCJW-UHFFFAOYSA-N 2-[4-(N,3-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)C=1C=C(C=CC=1)C AFHPEJCZXXGCJW-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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
• 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 3
• 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 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
• 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 3
• 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 3
• 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 3
• 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 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
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 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
• RNWQDCMDWCVTKY-UHFFFAOYSA-N 2-[4-[4-(cyclopropylmethoxy)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(CC1)COC1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 RNWQDCMDWCVTKY-UHFFFAOYSA-N 0.000 claims description 3
• QZCUBEQSMWDPAX-UHFFFAOYSA-N 2-[4-[methyl-(2-methylindazol-5-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=CC2=CN(N=C2C=C1)C QZCUBEQSMWDPAX-UHFFFAOYSA-N 0.000 claims description 3
• NWWGQFKDWMWTBL-UHFFFAOYSA-N 2-[4-[methyl-(5-methylpyridin-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=C(C=C1)C NWWGQFKDWMWTBL-UHFFFAOYSA-N 0.000 claims description 3
• UCLABKYGVIGHCE-OAHLLOKOSA-N 2-[4-[methyl-[(1R)-1-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)[C@H](C)C1=CC=CC=C1 UCLABKYGVIGHCE-OAHLLOKOSA-N 0.000 claims description 3
• UCLABKYGVIGHCE-HNNXBMFYSA-N 2-[4-[methyl-[(1S)-1-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)[C@@H](C)C1=CC=CC=C1 UCLABKYGVIGHCE-HNNXBMFYSA-N 0.000 claims description 3
• JJOMOXGDZFYMTA-UHFFFAOYSA-N 4-[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(N(C)C3=CC=C(C#N)C=C3)C=C1)C=NC=C2 JJOMOXGDZFYMTA-UHFFFAOYSA-N 0.000 claims description 3
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• MZTOMHWPTIFQHO-UHFFFAOYSA-N 2-[4-[3-[2-(dimethylamino)ethoxy]-4-ethyl-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(CCOC=1C=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=CC=1CC)C MZTOMHWPTIFQHO-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• BXVXQVVEVQBYAJ-UHFFFAOYSA-N 2-[4-[4-(2,2-dimethylpropoxy)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CC(COC1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1)(C)C BXVXQVVEVQBYAJ-UHFFFAOYSA-N 0.000 claims description 2
• WTKZKLMYONREEV-UHFFFAOYSA-N 2-[4-[4-(dimethylamino)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1)C WTKZKLMYONREEV-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• PEMGIHULNQGIMC-UHFFFAOYSA-N 2-[4-[N-methyl-3-(4-methyl-3-oxopiperazin-1-yl)anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound OC=1C2=C(N=C(N=1)OC1=CC=C(N(C)C=3C=C(C=CC=3)N3CC(N(CC3)C)=O)C=C1)C=NC=C2 PEMGIHULNQGIMC-UHFFFAOYSA-N 0.000 claims description 2
• OFRHQBQIVJZXJZ-UHFFFAOYSA-N 2-[4-[N-methyl-3-(trifluoromethyl)anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC(=CC=C1)C(F)(F)F)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 OFRHQBQIVJZXJZ-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• DCEPDRIEVVJKJY-UHFFFAOYSA-N 2-[4-[N-methyl-3-[methyl-(1-methylpiperidin-4-yl)amino]anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC(=CC=C1)N(C1CCN(CC1)C)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 DCEPDRIEVVJKJY-UHFFFAOYSA-N 0.000 claims description 2
• WQGWRPIKYVWCHC-UHFFFAOYSA-N 2-[4-[N-methyl-4-(1,1,1-trifluoropropan-2-yl)anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(C=C1)C(C(F)(F)F)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 WQGWRPIKYVWCHC-UHFFFAOYSA-N 0.000 claims description 2
• NZDMNKPYIPRUIY-UHFFFAOYSA-N 2-[4-[N-methyl-4-[1-(trifluoromethyl)cyclopropyl]anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(C=C1)C1(CC1)C(F)(F)F)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 NZDMNKPYIPRUIY-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• XRQUHCROKXDNHO-UHFFFAOYSA-N 2-[4-[methyl-(2-morpholin-4-ylpyridin-4-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=CC(=NC=C1)N1CCOCC1 XRQUHCROKXDNHO-UHFFFAOYSA-N 0.000 claims description 2
• SVKJXEWRSYIWNQ-UHFFFAOYSA-N 2-[4-[methyl-(6-propan-2-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(=CC=1)C(C)C SVKJXEWRSYIWNQ-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
• 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 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• PZELMUUIFIOJPX-UHFFFAOYSA-N 2-[4-[(5-ethylpyridin-2-yl)-methylamino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound 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 PZELMUUIFIOJPX-UHFFFAOYSA-N 0.000 claims 1
• QWMWXIHAUXGUJC-UHFFFAOYSA-N 2-[4-[3-(3-aminopiperidin-1-yl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound NC1CN(CCC1)C=1C=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=CC=1 QWMWXIHAUXGUJC-UHFFFAOYSA-N 0.000 claims 1
• LVCZMBLSEHDLOU-UHFFFAOYSA-N 2-[4-[3-(4-aminopiperidin-1-yl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound NC1CCN(CC1)C=1C=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=CC=1 LVCZMBLSEHDLOU-UHFFFAOYSA-N 0.000 claims 1
• ILQQXJRIRUBOGR-UHFFFAOYSA-N 2-[4-[4-(1-hydroxy-2-methylpropan-2-yl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound OCC(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 ILQQXJRIRUBOGR-UHFFFAOYSA-N 0.000 claims 1
• LTSJEPZXATVUOB-UHFFFAOYSA-N 2-[4-[4-(1-methoxy-2-methylpropan-2-yl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COCC(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 LTSJEPZXATVUOB-UHFFFAOYSA-N 0.000 claims 1
• ZALRKEUZTAWETR-UHFFFAOYSA-N 2-[4-[4-(2-hydroxypropan-2-yl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound OC(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 ZALRKEUZTAWETR-UHFFFAOYSA-N 0.000 claims 1
• JJSFOQOUHMAFLT-UHFFFAOYSA-N 2-[4-[4-(3,6-dihydro-2H-pyran-4-yl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound O1CCC(=CC1)C1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 JJSFOQOUHMAFLT-UHFFFAOYSA-N 0.000 claims 1
• GNLRAKTZEOBREI-UHFFFAOYSA-N 2-[4-[4-(4-aminobutan-2-yl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound NCCC(C)C1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 GNLRAKTZEOBREI-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• BRPMHVOFOJZGFY-UHFFFAOYSA-N 2-[4-[4-(cyclopropylmethyl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(CC1)CC1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 BRPMHVOFOJZGFY-UHFFFAOYSA-N 0.000 claims 1
• KEHMGHAAOPORBT-MRXNPFEDSA-N 2-[4-[4-[(2R)-butan-2-yl]-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C[C@H](CC)C1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 KEHMGHAAOPORBT-MRXNPFEDSA-N 0.000 claims 1
• KEHMGHAAOPORBT-INIZCTEOSA-N 2-[4-[4-[(2S)-butan-2-yl]-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C[C@@H](CC)C1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 KEHMGHAAOPORBT-INIZCTEOSA-N 0.000 claims 1
• SRKPNTNGEWKNIK-UHFFFAOYSA-N 2-[4-[4-[1-(2-methoxyethylamino)propan-2-yl]-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COCCNCC(C)C1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 SRKPNTNGEWKNIK-UHFFFAOYSA-N 0.000 claims 1
• DALZREFYBLXCFJ-UHFFFAOYSA-N 2-[4-[4-[1-[2-methoxyethyl(methyl)amino]propan-2-yl]-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COCCN(CC(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 DALZREFYBLXCFJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• CNBPHWUAZQNWQK-UHFFFAOYSA-N 2-[4-[4-ethyl-3-(2-methoxyethoxy)-N-methylanilino]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)OCCOC CNBPHWUAZQNWQK-UHFFFAOYSA-N 0.000 claims 1
• HFKUHUUSLPEHMF-UHFFFAOYSA-N 2-[4-[4-ethyl-N-methyl-3-(4-methylpiperazin-1-yl)anilino]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)N1CCN(CC1)C HFKUHUUSLPEHMF-UHFFFAOYSA-N 0.000 claims 1
• NBKFMLMGWXDBAZ-UHFFFAOYSA-N 2-[4-[N,3-dimethyl-5-(4-methylpiperazin-1-yl)anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC(=CC(=C1)N1CCN(CC1)C)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 NBKFMLMGWXDBAZ-UHFFFAOYSA-N 0.000 claims 1
• OPJXGSSNEIRHII-UHFFFAOYSA-N 2-[4-[N,4-dimethyl-3-(4-methylpiperazin-1-yl)anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC(=C(C=C1)C)N1CCN(CC1)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 OPJXGSSNEIRHII-UHFFFAOYSA-N 0.000 claims 1
• QDTKUEFKNNPUCQ-UHFFFAOYSA-N 2-[4-[N-(2-methoxyethyl)-4-propan-2-ylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COCCN(C1=CC=C(C=C1)C(C)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 QDTKUEFKNNPUCQ-UHFFFAOYSA-N 0.000 claims 1
• KNDXAVOTPBNGOB-UHFFFAOYSA-N 2-[4-[N-(oxolan-3-yl)-4-propan-2-ylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound O1CC(CC1)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 KNDXAVOTPBNGOB-UHFFFAOYSA-N 0.000 claims 1
• JDCPXUZUPWDZNX-UHFFFAOYSA-N 2-[4-[N-methyl-3-(4-methyl-1,4-diazepan-1-yl)anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC(=CC=C1)N1CCN(CCC1)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 JDCPXUZUPWDZNX-UHFFFAOYSA-N 0.000 claims 1
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