JP2015511245A5 - - Google Patents
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- JP2015511245A5 JP2015511245A5 JP2014558849A JP2014558849A JP2015511245A5 JP 2015511245 A5 JP2015511245 A5 JP 2015511245A5 JP 2014558849 A JP2014558849 A JP 2014558849A JP 2014558849 A JP2014558849 A JP 2014558849A JP 2015511245 A5 JP2015511245 A5 JP 2015511245A5
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- JP
- Japan
- Prior art keywords
- amino
- alkyl
- phenyl
- pyrido
- pyrimidin
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 43
- -1 aryl-C 1-6 -alkyl- Chemical group 0.000 claims 38
- 125000001072 heteroaryl group Chemical group 0.000 claims 34
- 125000003118 aryl group Chemical group 0.000 claims 32
- 125000001475 halogen functional group Chemical group 0.000 claims 32
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 30
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 30
- 150000003839 salts Chemical class 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 125000001424 substituent group Chemical group 0.000 claims 20
- 239000012453 solvate Substances 0.000 claims 18
- 150000002431 hydrogen Chemical class 0.000 claims 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 9
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 3
- 229940095102 methyl benzoate Drugs 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
- AMDZGJIAKLYONC-UHFFFAOYSA-N 2-[4-[[6-(2,6-dichlorophenyl)-8-methyl-5-oxopyrido[4,3-d]pyrimidin-2-yl]amino]phenyl]sulfonyl-n-methylacetamide Chemical compound C1=CC(S(=O)(=O)CC(=O)NC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 AMDZGJIAKLYONC-UHFFFAOYSA-N 0.000 claims 2
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims 2
- MIIKEUZRZIUNFL-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[(1,1-dimethyl-2,3-dihydroisoindol-5-yl)amino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4C(C(NC4)(C)C)=CC=3)N=C2C(C)=CN1C1=C(Cl)C=CC=C1Cl MIIKEUZRZIUNFL-UHFFFAOYSA-N 0.000 claims 2
- JXVVNMLOOWMJPU-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[4-(1-methylpiperidin-4-yl)oxyanilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCC1OC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 JXVVNMLOOWMJPU-UHFFFAOYSA-N 0.000 claims 2
- UPTKQADDXWWLFL-UHFFFAOYSA-N 6-(2-hydroxy-6-methylphenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=CC=CC(O)=C1N1C(=O)C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=C1 UPTKQADDXWWLFL-UHFFFAOYSA-N 0.000 claims 2
- CSBPQHGADOHBPJ-UHFFFAOYSA-N 6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=NC=C2C(=O)NC=CC2=N1 CSBPQHGADOHBPJ-UHFFFAOYSA-N 0.000 claims 2
- SJKPWMYKSVBUNO-UHFFFAOYSA-N 8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)-6-(1,3,5-trimethylpyrazol-4-yl)pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=NN(C)C(C)=C1N1C(=O)C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=C1 SJKPWMYKSVBUNO-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims 2
- YXRWEBGBSHYCEB-UHFFFAOYSA-N 2-[4-(2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl)anilino]-6-(2,6-dichlorophenyl)-8-ethenylpyrido[4,3-d]pyrimidin-5-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4CNCC4C3)N=C2C(C=C)=C1 YXRWEBGBSHYCEB-UHFFFAOYSA-N 0.000 claims 1
- WMAILZJXDPEVNY-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-6-phenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C=CC=CC=3)C=CC2=N1 WMAILZJXDPEVNY-UHFFFAOYSA-N 0.000 claims 1
- DFPKHQPIXTVYBE-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-6-phenylpyrimido[5,4-c][1,8]naphthyridin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C=CC=CC=3)C3=NC=CC=C3C2=N1 DFPKHQPIXTVYBE-UHFFFAOYSA-N 0.000 claims 1
- JCNQHHRWQHCLQK-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-6-phenylpyrimido[5,4-c]quinolin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C=CC=CC=3)C3=CC=CC=C3C2=N1 JCNQHHRWQHCLQK-UHFFFAOYSA-N 0.000 claims 1
- JMYMRWWPXDAHQC-UHFFFAOYSA-N 2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-6-(2,6-dimethylphenyl)-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3C)C)C=C(C)C2=N1 JMYMRWWPXDAHQC-UHFFFAOYSA-N 0.000 claims 1
- PXDTVJDUPULMJX-UHFFFAOYSA-N 2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-6-(2-fluoro-6-methylphenyl)-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3C)F)C=C(C)C2=N1 PXDTVJDUPULMJX-UHFFFAOYSA-N 0.000 claims 1
- WIDVDMOQFQSPCF-UHFFFAOYSA-N 2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-methyl-6-[2-(1,3-oxazol-5-yl)phenyl]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)C=3OC=NC=3)C=C(C)C2=N1 WIDVDMOQFQSPCF-UHFFFAOYSA-N 0.000 claims 1
- DOZVXATWWKJRRW-UHFFFAOYSA-N 2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-methyl-6-naphthalen-1-ylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C4=CC=CC=C4C=CC=3)C=C(C)C2=N1 DOZVXATWWKJRRW-UHFFFAOYSA-N 0.000 claims 1
- PFHXDGVRFUKYMC-UHFFFAOYSA-N 2-[4-[4-[3-(dimethylamino)propyl]piperazin-1-yl]anilino]-6-(2,6-dimethylphenyl)-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(CCCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3C)C)C=C(C)C2=N1 PFHXDGVRFUKYMC-UHFFFAOYSA-N 0.000 claims 1
- BTSIRDYMWZOQJR-UHFFFAOYSA-N 2-[4-[[6-(2,6-dichlorophenyl)-8-methyl-5-oxopyrido[4,3-d]pyrimidin-2-yl]amino]phenyl]sulfanyl-n-methylacetamide Chemical compound C1=CC(SCC(=O)NC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 BTSIRDYMWZOQJR-UHFFFAOYSA-N 0.000 claims 1
- SXIOYKBEPRVZKU-UHFFFAOYSA-N 2-[[2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxo-8-phenylpyrido[4,3-d]pyrimidin-6-yl]methyl]benzonitrile Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(CC=3C(=CC=CC=3)C#N)C=C(C=3C=CC=CC=3)C2=N1 SXIOYKBEPRVZKU-UHFFFAOYSA-N 0.000 claims 1
- XIPFHAWJSGGGPQ-UHFFFAOYSA-N 2-amino-6-(2,6-dichlorophenyl)-8-(1h-imidazol-2-yl)pyrido[4,3-d]pyrimidin-5-one Chemical compound N=1C(N)=NC=C(C2=O)C=1C(C=1NC=CN=1)=CN2C1=C(Cl)C=CC=C1Cl XIPFHAWJSGGGPQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- CQZXDCLATNWQQZ-UHFFFAOYSA-N 6,8-dimethyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C)C=C(C)C2=N1 CQZXDCLATNWQQZ-UHFFFAOYSA-N 0.000 claims 1
- LKCXJVXBLGUQLS-UHFFFAOYSA-N 6-(2,5-dichlorophenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C)=CN1C1=CC(Cl)=CC=C1Cl LKCXJVXBLGUQLS-UHFFFAOYSA-N 0.000 claims 1
- HOUHOTYYSIYDFC-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)amino]-8-(hydroxymethyl)pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C(C)(C)CNCC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(CO)=CN2C1=C(Cl)C=CC=C1Cl HOUHOTYYSIYDFC-UHFFFAOYSA-N 0.000 claims 1
- MIUBKIYRAXCJIU-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)amino]-8-ethenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C=C2C(C)(C)CNCC2=CC=1NC(N=1)=NC=C(C2=O)C=1C(C=C)=CN2C1=C(Cl)C=CC=C1Cl MIUBKIYRAXCJIU-UHFFFAOYSA-N 0.000 claims 1
- ASWALLSSOKXUQL-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)amino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4C(C(CNC4)(C)C)=CC=3)N=C2C(C)=CN1C1=C(Cl)C=CC=C1Cl ASWALLSSOKXUQL-UHFFFAOYSA-N 0.000 claims 1
- CMEQFADKTUIHOO-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxopyrido[4,3-d]pyrimidine-8-carbaldehyde Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C=O)C2=N1 CMEQFADKTUIHOO-UHFFFAOYSA-N 0.000 claims 1
- YDMNUKRSAVGCQM-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-(4-methylpiperazin-1-yl)anilino]-8-[(2,2,2-trifluoroethylamino)methyl]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(CNCC(F)(F)F)C2=N1 YDMNUKRSAVGCQM-UHFFFAOYSA-N 0.000 claims 1
- HXZJOJDQTHEMAD-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[2-(dimethylamino)ethylamino]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(NCCN(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 HXZJOJDQTHEMAD-UHFFFAOYSA-N 0.000 claims 1
- VEISEJCVUWRJGG-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[2-(dimethylamino)ethylsulfanyl]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(SCCN(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 VEISEJCVUWRJGG-UHFFFAOYSA-N 0.000 claims 1
- LRGODSVHKJTERV-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-(fluoromethyl)pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(CF)C2=N1 LRGODSVHKJTERV-UHFFFAOYSA-N 0.000 claims 1
- GWDGQFOINGYQNX-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-ethenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C=C)C2=N1 GWDGQFOINGYQNX-UHFFFAOYSA-N 0.000 claims 1
- MCRKRMLKCMUFDV-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 MCRKRMLKCMUFDV-UHFFFAOYSA-N 0.000 claims 1
- CUNXQDQMSJICOC-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(CCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 CUNXQDQMSJICOC-UHFFFAOYSA-N 0.000 claims 1
- RGBZKKMZCHLFNC-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-[3-(dimethylamino)propyl]piperazin-1-yl]anilino]-8-(fluoromethyl)pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(CCCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(CF)C2=N1 RGBZKKMZCHLFNC-UHFFFAOYSA-N 0.000 claims 1
- TZDQYQGVRAIVRG-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-[3-(dimethylamino)propyl]piperazin-1-yl]anilino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(CCCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C)C2=N1 TZDQYQGVRAIVRG-UHFFFAOYSA-N 0.000 claims 1
- KHVRFRVIMHYRKA-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[[2-(dimethylamino)-2,3-dihydro-1h-inden-5-yl]amino]-8-(fluoromethyl)pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1C(CF)=CN2C1=C(Cl)C=CC=C1Cl KHVRFRVIMHYRKA-UHFFFAOYSA-N 0.000 claims 1
- FPKNDQJSHUPUFU-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[[2-(dimethylamino)-2,3-dihydro-1h-inden-5-yl]amino]-8-(hydroxymethyl)pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1C(CO)=CN2C1=C(Cl)C=CC=C1Cl FPKNDQJSHUPUFU-UHFFFAOYSA-N 0.000 claims 1
- XNKJFJJPOSELAO-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[[2-(dimethylamino)-2,3-dihydro-1h-inden-5-yl]amino]-8-ethenylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1C(C=C)=CN2C1=C(Cl)C=CC=C1Cl XNKJFJJPOSELAO-UHFFFAOYSA-N 0.000 claims 1
- ALMUSLUKAWFXQQ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[[2-(dimethylamino)-2,3-dihydro-1h-inden-5-yl]amino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C2CC(N(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1C(C)=CN2C1=C(Cl)C=CC=C1Cl ALMUSLUKAWFXQQ-UHFFFAOYSA-N 0.000 claims 1
- YPUAYOIIVMBLGA-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[[2-[2-(dimethylamino)ethyl]-1,3-dihydroisoindol-5-yl]amino]-8-methylpyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C2CN(CCN(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1C(C)=CN2C1=C(Cl)C=CC=C1Cl YPUAYOIIVMBLGA-UHFFFAOYSA-N 0.000 claims 1
- NFXWJHGRCDFSTE-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(1-hydroxyethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C2C(C(O)C)=CN1C1=C(Cl)C=CC=C1Cl NFXWJHGRCDFSTE-UHFFFAOYSA-N 0.000 claims 1
- UYXHKNZXQUASFC-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(1h-imidazol-2-yl)-2-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4CCNCC4=CC=3)N=C2C(C=2NC=CN=2)=C1 UYXHKNZXQUASFC-UHFFFAOYSA-N 0.000 claims 1
- JEBLLDTYWCQIIF-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(1h-imidazol-2-yl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C=C(C=3NC=CN=3)C2=N1 JEBLLDTYWCQIIF-UHFFFAOYSA-N 0.000 claims 1
- ORPPVRBOTBKNJV-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(difluoromethyl)-2-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CCNCC4=CC=3)N=C2C(C(F)F)=CN1C1=C(Cl)C=CC=C1Cl ORPPVRBOTBKNJV-UHFFFAOYSA-N 0.000 claims 1
- ZEDRBKISKNUZRX-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-(difluoromethyl)-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1C2=CN=C(NC=3C=C4CNCCC4=CC=3)N=C2C(C(F)F)=CN1C1=C(Cl)C=CC=C1Cl ZEDRBKISKNUZRX-UHFFFAOYSA-N 0.000 claims 1
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| GB201703881D0 (en) * | 2017-03-10 | 2017-04-26 | Almac Discovery Ltd | Pharmaceutical compounds |
| US20200108074A1 (en) | 2017-03-31 | 2020-04-09 | Seattle Genetics, Inc. | Combinations of chk1- and wee1- inhibitors |
| EP3652174A4 (en) * | 2017-07-13 | 2021-06-30 | Syros Pharmaceuticals, Inc. | TAM KINASE INHIBITORS |
| CN109422754A (zh) * | 2017-08-24 | 2019-03-05 | 上海迪诺医药科技有限公司 | 吡唑并[3,4-d]嘧啶-3-酮衍生物、其药物组合物及应用 |
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| KR102697799B1 (ko) | 2019-03-22 | 2024-08-23 | 쇼우야오 홀딩스 (베이징) 코., 엘티디. | Wee1 억제제 및 이의 제조 및 용도 |
| MX2021012418A (es) | 2019-04-09 | 2021-11-12 | Nuvation Bio Inc | Compuestos heterociclicos y sus usos. |
| PT3964510T (pt) | 2019-04-30 | 2024-07-29 | Wuxi Biocity Biopharmaceutics Co Ltd | Forma cristalina do composto inibidor de wee1 e sua utilização |
| CN115397827B (zh) * | 2020-03-27 | 2024-03-15 | 贝达药业股份有限公司 | Fgfr4抑制剂的盐型、晶型及其用途 |
| US20230159540A1 (en) | 2020-06-17 | 2023-05-25 | Wigen Biomedicine Technology (shanghai) Co., Ltd. | PYRAZOLO[3,4-d]PYRIMIDIN-3-ONE DERIVATIVE AS WEE-1 INHIBITOR |
| AU2022265032A1 (en) | 2021-04-30 | 2023-11-16 | Wigen Biomedicine Technology (shanghai) Co., Ltd. | Fused ring compound as wee-1 inhibitor, and preparation method therefor and use thereof |
| AU2022287033B2 (en) * | 2021-06-04 | 2025-04-17 | Aprea Therapeutics, Inc. | Pyridopyrimidine derivatives useful as wee1 kinase inhibitors |
| CN116462687B (zh) | 2022-01-18 | 2025-01-07 | 江苏天士力帝益药业有限公司 | Wee1抑制剂及其制备和用途 |
| IL315441A (en) | 2022-03-07 | 2024-11-01 | Debiopharm Int Sa | Treatment methods for small cell lung cancer |
| CN117402162A (zh) | 2022-07-13 | 2024-01-16 | 江苏天士力帝益药业有限公司 | Wee1抑制剂及其制备和用途 |
| TW202519221A (zh) | 2023-09-14 | 2025-05-16 | 瑞士商德彪製藥國際公司 | Ｗｅｅ１抑制劑及ｐｋｍｙｔ１抑制劑之組合 |
| WO2025133381A2 (en) | 2023-12-22 | 2025-06-26 | Debiopharm International S.A. | Methods of treating solid tumors |
| WO2025186213A1 (en) | 2024-03-04 | 2025-09-12 | Debiopharm International S.A. | Combination of a wee1 inhibitor and a topoisomerase 1 inhibitor |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5633003A (en) * | 1994-03-31 | 1997-05-27 | Cantor; Jerome O. | Use of intratracheally administered hyaluronic acid to ameliorate emphysema |
| JP2003528101A (ja) * | 2000-03-06 | 2003-09-24 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | ５−アルキルピリド［２，３−ｄ］ピリミジンチロシンキナーゼ阻害剤 |
| US20080255162A1 (en) * | 2004-05-04 | 2008-10-16 | Warner-Lambert Company Llc | Pyrrolyl Substituted Pyrido[2,3-D]Pyrimidin-7-Ones and Derivatives Thereof as Therapeutic Agents |
| ATE439361T1 (de) * | 2006-01-31 | 2009-08-15 | Hoffmann La Roche | 7h-pyridoä3,4-düpyrimidin-8-one, ihre herstellung und ihre verwendung als proteinkinaseinhibitoren |
| AR060635A1 (es) * | 2006-04-27 | 2008-07-02 | Banyu Pharma Co Ltd | Derivados de 1,2-dihidro-3h-pirazolo[3,4-d]pirimidin-3-ona, composiciones farmaceuticas que los comprenden y su uso en el tratamiento del cancer |
| EP2330909B1 (en) * | 2008-08-12 | 2013-09-18 | GlaxoSmithKline LLC | Chemical compounds |
| AU2009321867B2 (en) * | 2008-12-01 | 2015-12-10 | Merck Patent Gmbh | 2,5-Diamino-substituted pyrido[4,3-d]pyrimidines as autotaxin inhibitors against cancer |
| WO2010067888A1 (en) * | 2008-12-12 | 2010-06-17 | Banyu Pharmaceutical Co.,Ltd. | Dihydropyrimidopyrimidine derivatives |
| WO2011053861A1 (en) * | 2009-10-29 | 2011-05-05 | Genosco | Kinase inhibitors |
| CA2881279C (en) * | 2012-08-07 | 2020-07-07 | Merck Patent Gmbh | Pyridopyrimidine derivatives as protein kinase inhibitors |
| GB201306610D0 (en) * | 2013-04-11 | 2013-05-29 | Almac Discovery Ltd | Pharmaceutical compounds |
-
2013
- 2013-02-22 US US13/773,906 patent/US9718821B2/en active Active
- 2013-02-22 CN CN201380021182.4A patent/CN104271576A/zh active Pending
- 2013-02-22 ES ES13707095.9T patent/ES2606640T3/es active Active
- 2013-02-22 JP JP2014558849A patent/JP2015511245A/ja active Pending
- 2013-02-22 EP EP13707095.9A patent/EP2817308B1/en not_active Not-in-force
- 2013-02-22 MX MX2014010176A patent/MX2014010176A/es unknown
- 2013-02-22 CA CA2864142A patent/CA2864142A1/en not_active Abandoned
- 2013-02-22 WO PCT/US2013/027265 patent/WO2013126656A1/en not_active Ceased
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