JP2017529346A5 - - Google Patents
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- Publication number
- JP2017529346A5 JP2017529346A5 JP2017514615A JP2017514615A JP2017529346A5 JP 2017529346 A5 JP2017529346 A5 JP 2017529346A5 JP 2017514615 A JP2017514615 A JP 2017514615A JP 2017514615 A JP2017514615 A JP 2017514615A JP 2017529346 A5 JP2017529346 A5 JP 2017529346A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- pharmaceutically acceptable
- acceptable salt
- pyrido
- phenoxy
- 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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- 150000003839 salts Chemical class 0.000 claims 120
- 150000001875 compounds Chemical class 0.000 claims 118
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000001153 fluoro group Chemical group F* 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000004452 carbocyclyl group Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- -1 1,2,3,4-tetrahydronaphthalenyl Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 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 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 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
- 239000003814 drug Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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
- 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 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
- 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 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
- 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 1
- 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 1
- 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 1
- 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 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
- 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 1
- 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 1
- 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 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
- 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 1
- 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 1
- 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 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
- 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 1
- 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 1
- 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 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
- 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 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
- 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 1
- 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 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
- 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 1
- 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 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
- 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 1
- 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 1
- 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 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
- 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 1
- 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 1
- 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 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
- 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 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
- 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 1
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- 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 1
- 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 1
- 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 1
- 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 1
- 102000008157 Histone Demethylases Human genes 0.000 claims 1
- 108010074870 Histone Demethylases Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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| US62/051,691 | 2014-09-17 | ||
| PCT/US2015/050432 WO2016044429A1 (en) | 2014-09-17 | 2015-09-16 | Histone demethylase inhibitors |
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| JP2017529346A JP2017529346A (ja) | 2017-10-05 |
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| SG (1) | SG11201702147TA (https=) |
| WO (1) | WO2016044429A1 (https=) |
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| HRP20171609T1 (hr) | 2013-03-15 | 2017-12-15 | Quanticel Pharmaceuticals Inc | Inhibitori histon demetilaze |
| US9643965B2 (en) | 2014-09-17 | 2017-05-09 | Celgene Quantical Research, Inc. | Histone demethylase inhibitors |
| JP6970681B2 (ja) * | 2016-03-15 | 2021-11-24 | セルジーン クオンティセル リサーチ，インク． | ヒストンデメチラーゼ阻害剤 |
| US10150754B2 (en) | 2016-04-19 | 2018-12-11 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| SI3546456T1 (sl) | 2016-11-28 | 2022-04-29 | Teijin Pharma Limited | Kristal derivata pirido(3,4-D)pirimidina ali njegovega solvata |
| US11040973B2 (en) | 2017-03-29 | 2021-06-22 | Purdue Research Foundation | Inhibitors of kinase networks and uses thereof |
| WO2020113094A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| EP4074317A1 (en) | 2021-04-14 | 2022-10-19 | Bayer AG | Phosphorus derivatives as novel sos1 inhibitors |
| CN115368252B (zh) * | 2022-09-19 | 2024-01-12 | 西北农林科技大学 | 一种4-胺基酚类衍生物及应用 |
| CN116253712B (zh) * | 2023-03-27 | 2025-05-02 | 昆山市第一人民医院 | 5,6,7-三甲氧基-2,3-二氢喹啉类化合物、药物组合物及用途 |
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| EP1447405A4 (en) * | 2001-10-17 | 2005-01-12 | Kirin Brewery | CHINOLIN OR CHINAZOLINE DERIVATIVES THAT PREVENT THE AUTOPHOSPHORYLATION OF RECEPTORS FOR THE FIBROBLAST GROWTH FACTOR |
| AU2003218215A1 (en) * | 2002-03-15 | 2003-09-29 | Vertex Pharmaceuticals, Inc. | Azolylaminoazines as inhibitors of protein kinases |
| CA2527017A1 (en) * | 2003-05-27 | 2004-12-09 | Pfizer Products Inc. | Quinazolines and pyrido [3,4-d] pyrimidines as receptor tyrosine kinase inhibitors |
| US7544677B2 (en) * | 2004-08-23 | 2009-06-09 | Merck & Co., Inc. | Inhibitors of Akt activity |
| FR2876103B1 (fr) | 2004-10-01 | 2008-02-22 | Aventis Pharma Sa | Nouveaux derives bis-azaindoles, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de kinases |
| EP2061772A4 (en) | 2006-09-11 | 2011-06-29 | Curis Inc | MULTIFUNCTIONAL SMALL MOLECULES AS PROLIFERATION-ACTIVE ACTIVE SUBSTANCES |
| TW200922590A (en) | 2007-09-10 | 2009-06-01 | Curis Inc | VEGFR inhibitors containing a zinc binding moiety |
| JP5552608B2 (ja) | 2012-04-27 | 2014-07-16 | 株式会社ソフイア | 遊技機 |
| RS55764B1 (sr) | 2012-10-02 | 2017-07-31 | Gilead Sciences | Inhibitori histonskih demetilaza |
| US8969343B2 (en) | 2012-12-19 | 2015-03-03 | Quanticel Pharmaceuticals, Inc. | Histone demethylase inhibitors |
| WO2014100818A1 (en) | 2012-12-21 | 2014-06-26 | Quanticel Pharmaceuticals, Inc. | Histone demethylase inhibitors |
| JP6320506B2 (ja) | 2013-03-12 | 2018-05-09 | セルジーン クオンティセル リサーチ，インク． | ヒストンデメチラーゼ阻害剤 |
| HRP20171609T1 (hr) | 2013-03-15 | 2017-12-15 | Quanticel Pharmaceuticals Inc | Inhibitori histon demetilaze |
| WO2014144850A1 (en) | 2013-03-15 | 2014-09-18 | Genentech, Inc. | Methods of treating cancer and preventing cancer drug resistance |
| AR100997A1 (es) | 2014-06-25 | 2016-11-16 | Quanticel Pharmaceuticals Inc | Derivados de piridina como inhibidores de histona demetilasa |
| US9643965B2 (en) * | 2014-09-17 | 2017-05-09 | Celgene Quantical Research, Inc. | Histone demethylase inhibitors |
| US10030017B2 (en) | 2014-09-17 | 2018-07-24 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| JP6970681B2 (ja) | 2016-03-15 | 2021-11-24 | セルジーン クオンティセル リサーチ，インク． | ヒストンデメチラーゼ阻害剤 |
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2015
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- 2015-09-16 EP EP18181949.1A patent/EP3453710B1/en active Active
- 2015-09-16 CA CA2961610A patent/CA2961610A1/en not_active Abandoned
- 2015-09-16 SG SG11201702147TA patent/SG11201702147TA/en unknown
- 2015-09-16 AU AU2015317806A patent/AU2015317806A1/en not_active Abandoned
- 2015-09-16 KR KR1020177009917A patent/KR20170048591A/ko not_active Withdrawn
- 2015-09-16 ES ES15842574T patent/ES2910226T3/es active Active
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- 2015-09-16 JP JP2017514615A patent/JP6552608B2/ja not_active Expired - Fee Related
- 2015-09-16 EP EP15842574.4A patent/EP3193601B1/en not_active Not-in-force
- 2015-09-16 MX MX2017003466A patent/MX2017003466A/es unknown
- 2015-09-16 BR BR112017005511A patent/BR112017005511A2/pt not_active Application Discontinuation
- 2015-09-16 WO PCT/US2015/050432 patent/WO2016044429A1/en not_active Ceased
- 2015-09-16 CN CN201580061425.6A patent/CN107205391A/zh active Pending
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2017
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- 2017-05-05 US US15/588,561 patent/US10112940B2/en active Active
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2018
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2020
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2024
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