SI3083625T1 - Pyrimidopyrimidinones, useful as Wee-1 kinase inhibitors - Google Patents
Pyrimidopyrimidinones, useful as Wee-1 kinase inhibitors Download PDFInfo
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- SI3083625T1 SI3083625T1 SI201430580T SI201430580T SI3083625T1 SI 3083625 T1 SI3083625 T1 SI 3083625T1 SI 201430580 T SI201430580 T SI 201430580T SI 201430580 T SI201430580 T SI 201430580T SI 3083625 T1 SI3083625 T1 SI 3083625T1
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- SI
- Slovenia
- Prior art keywords
- methyl
- amino
- dihydropyrimido
- pyrimidin
- phenyl
- Prior art date
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- RLJCWYYOGHGGBV-UHFFFAOYSA-N 1h-pyrimido[5,4-d]pyrimidin-2-one Chemical class C1=NC=C2NC(=O)N=CC2=N1 RLJCWYYOGHGGBV-UHFFFAOYSA-N 0.000 title claims 2
- 229940043355 kinase inhibitor Drugs 0.000 title claims 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
- 206010028980 Neoplasm Diseases 0.000 claims abstract 3
- 201000011510 cancer Diseases 0.000 claims abstract 3
- -1 2,6-dichlorophenyl group Chemical group 0.000 claims 145
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 150000001204 N-oxides Chemical class 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- YFDRYBUJCGOYCQ-WDSKDSINSA-N (1s,4s)-2-methyl-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1N(C)[C@]2([H])CN[C@@]1([H])C2 YFDRYBUJCGOYCQ-WDSKDSINSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- POODCGLTDGRVDY-UHFFFAOYSA-N 2-[4-(1-cyclobutylpiperidin-4-yl)-3-(hydroxymethyl)anilino]-6-(2,6-dichlorophenyl)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C1(CCC1)N1CCC(CC1)C1=C(C=C(C=C1)NC1=NC=C2C(=N1)N(CN(C2=O)C1=C(C=CC=C1Cl)Cl)C)CO POODCGLTDGRVDY-UHFFFAOYSA-N 0.000 claims 1
- ZLUTULCSXWROMX-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)-3-(pyrrolidin-1-ylmethyl)anilino]-6-(2,6-dichlorophenyl)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C(C)(=O)N1CCN(CC1)C1=C(C=C(C=C1)NC1=NC=C2C(=N1)N(CN(C2=O)C1=C(C=CC=C1Cl)Cl)C)CN1CCCC1 ZLUTULCSXWROMX-UHFFFAOYSA-N 0.000 claims 1
- GVWNQNHECMZMEG-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-6-(2,6-dichlorophenyl)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(CN(C2=O)C1=C(C=CC=C1Cl)Cl)C GVWNQNHECMZMEG-UHFFFAOYSA-N 0.000 claims 1
- FTSTXKGYDQGDFO-UHFFFAOYSA-N 2-[4-(4-cyclopropylpiperazin-1-yl)anilino]-6-(2,6-dichlorophenyl)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C1(CC1)N1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(CN(C2=O)C1=C(C=CC=C1Cl)Cl)C FTSTXKGYDQGDFO-UHFFFAOYSA-N 0.000 claims 1
- MPSDZSSVMJBCCW-HOTGVXAUSA-N 2-[4-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-methoxyanilino]-6-(2,6-dichlorophenyl)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound COc1cc(Nc2ncc3C(=O)N(CN(C)c3n2)c2c(Cl)cccc2Cl)ccc1N1C[C@@H]2C[C@H]1CN2 MPSDZSSVMJBCCW-HOTGVXAUSA-N 0.000 claims 1
- ZDZWFQQAICCRME-IRXDYDNUSA-N 2-[4-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-methylanilino]-6-(2,6-dichlorophenyl)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound CN1CN(C(=O)c2cnc(Nc3ccc(N4C[C@@H]5C[C@H]4CN5)c(C)c3)nc12)c1c(Cl)cccc1Cl ZDZWFQQAICCRME-IRXDYDNUSA-N 0.000 claims 1
- TWVKPGADTNJSQI-UHFFFAOYSA-N 2-[4-[4-[[6-(2,6-dichlorophenyl)-8-methyl-5-oxo-7H-pyrimido[4,5-d]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]acetic acid hydrochloride Chemical compound Cl.CN1CN(C(=O)c2cnc(Nc3ccc(cc3)N3CCN(CC(O)=O)CC3)nc12)c1c(Cl)cccc1Cl TWVKPGADTNJSQI-UHFFFAOYSA-N 0.000 claims 1
- RJMSAQHOZFUOFX-UHFFFAOYSA-N 2-[4-bromo-3-(methylaminomethyl)anilino]-6-(2,6-dichlorophenyl)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound BrC1=C(C=C(C=C1)NC1=NC=C2C(=N1)N(CN(C2=O)C1=C(C=CC=C1Cl)Cl)C)CNC RJMSAQHOZFUOFX-UHFFFAOYSA-N 0.000 claims 1
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims 1
- WMNTUWBEVOCCIL-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-(3-fluoro-4-piperazin-1-ylanilino)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCNCC1)F)C WMNTUWBEVOCCIL-UHFFFAOYSA-N 0.000 claims 1
- QHBLDARXYVRQPT-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-(3-methoxy-4-piperazin-1-ylanilino)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCNCC1)OC)C QHBLDARXYVRQPT-UHFFFAOYSA-N 0.000 claims 1
- YREZFGSRZATOLT-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-(3-methoxy-4-piperidin-4-ylanilino)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)C1CCNCC1)OC)C YREZFGSRZATOLT-UHFFFAOYSA-N 0.000 claims 1
- QJQUTIICTMGERH-MRXNPFEDSA-N 6-(2,6-dichlorophenyl)-2-[3-(2-hydroxypropan-2-yl)-4-[(3R)-3-methylpiperazin-1-yl]anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1C[C@H](NCC1)C)C(C)(C)O)C QJQUTIICTMGERH-MRXNPFEDSA-N 0.000 claims 1
- KGMYLTSFAPTXIB-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-(ethylaminomethyl)-4-morpholin-4-ylanilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCOCC1)CNCC)C KGMYLTSFAPTXIB-UHFFFAOYSA-N 0.000 claims 1
- FSYWYBWCFILSNX-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-(hydroxymethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)C=1CCNCC=1)CO)C FSYWYBWCFILSNX-UHFFFAOYSA-N 0.000 claims 1
- YMXITXZZVGLRFY-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-(hydroxymethyl)-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)C=1CCN(CC=1)C)CO)C YMXITXZZVGLRFY-UHFFFAOYSA-N 0.000 claims 1
- QLFLZMARLZNPCW-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-(hydroxymethyl)-4-(4-propan-2-ylpiperazin-1-yl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCN(CC1)C(C)C)CO)C QLFLZMARLZNPCW-UHFFFAOYSA-N 0.000 claims 1
- AIHHGFLJFSDSFZ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-(hydroxymethyl)-4-(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CC2CCC(C1)N2C)CO)C AIHHGFLJFSDSFZ-UHFFFAOYSA-N 0.000 claims 1
- LUYCBKWHYHGSMI-GOSISDBHSA-N 6-(2,6-dichlorophenyl)-2-[3-(hydroxymethyl)-4-[(3R)-3-(methoxymethyl)piperazin-1-yl]anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1C[C@@H](NCC1)COC)CO)C LUYCBKWHYHGSMI-GOSISDBHSA-N 0.000 claims 1
- RERWAFRPAAIWBP-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-(hydroxymethyl)-4-morpholin-4-ylanilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCOCC1)CO)C RERWAFRPAAIWBP-UHFFFAOYSA-N 0.000 claims 1
- NLEKABKQRTTZQM-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-(hydroxymethyl)-4-piperazin-1-ylanilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCNCC1)CO)C NLEKABKQRTTZQM-UHFFFAOYSA-N 0.000 claims 1
- VLSTVCLRRXOTDJ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-(hydroxymethyl)-4-piperidin-1-ylanilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCCCC1)CO)C VLSTVCLRRXOTDJ-UHFFFAOYSA-N 0.000 claims 1
- XCCUNKZLGDBUDS-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-(methoxymethyl)-4-piperazin-1-ylanilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCNCC1)COC)C XCCUNKZLGDBUDS-UHFFFAOYSA-N 0.000 claims 1
- PBMOGRDBNXYTKG-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-[(dimethylamino)methyl]-4-(1,1-dioxo-1,4-thiazinan-4-yl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCS(CC1)(=O)=O)CN(C)C)C PBMOGRDBNXYTKG-UHFFFAOYSA-N 0.000 claims 1
- CPYGWIHTHJOPLM-HDICACEKSA-N 6-(2,6-dichlorophenyl)-2-[3-[(dimethylamino)methyl]-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1C[C@@H](O[C@@H](C1)C)C)CN(C)C)C CPYGWIHTHJOPLM-HDICACEKSA-N 0.000 claims 1
- VDHTVEOKJVXWRR-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-[(dimethylamino)methyl]-4-morpholin-4-ylanilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCOCC1)CN(C)C)C VDHTVEOKJVXWRR-UHFFFAOYSA-N 0.000 claims 1
- FULAUYGMXLNYKP-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-[2-(dimethylamino)-1-hydroxyethyl]anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=CC=C1)C(CN(C)C)O)C FULAUYGMXLNYKP-UHFFFAOYSA-N 0.000 claims 1
- ZGOROSLDYMDTIU-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-(1,1-dioxo-1,4-thiazinan-4-yl)-3-(methylaminomethyl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCS(CC1)(=O)=O)CNC)C ZGOROSLDYMDTIU-UHFFFAOYSA-N 0.000 claims 1
- KMQLDJJMLMAAJT-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-(3,3-dimethylpiperazin-1-yl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1CC(NCC1)(C)C)C KMQLDJJMLMAAJT-UHFFFAOYSA-N 0.000 claims 1
- QARMPXIUYRAGLB-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-(4,4-difluoropiperidin-1-yl)-3-(methylaminomethyl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCC(CC1)(F)F)CNC)C QARMPXIUYRAGLB-UHFFFAOYSA-N 0.000 claims 1
- AAKMZAPERHRRQH-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-(4,4-difluoropiperidin-1-yl)-3-[(dimethylamino)methyl]anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCC(CC1)(F)F)CN(C)C)C AAKMZAPERHRRQH-UHFFFAOYSA-N 0.000 claims 1
- OTZUTQFGFIDOJK-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-(4-ethylpiperazin-1-yl)-3-(hydroxymethyl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCN(CC1)CC)CO)C OTZUTQFGFIDOJK-UHFFFAOYSA-N 0.000 claims 1
- HBOJJBPKOUDXCN-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-(4-ethylpiperazin-1-yl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1CCN(CC1)CC)C HBOJJBPKOUDXCN-UHFFFAOYSA-N 0.000 claims 1
- JOZMUYGWCBSIHQ-CALCHBBNSA-N 6-(2,6-dichlorophenyl)-2-[4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-(methylaminomethyl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1C[C@@H](O[C@@H](C1)C)C)CNC)C JOZMUYGWCBSIHQ-CALCHBBNSA-N 0.000 claims 1
- KORCVBOCKBZMRD-MRXNPFEDSA-N 6-(2,6-dichlorophenyl)-2-[4-[(3R)-3,4-dimethylpiperazin-1-yl]anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1C[C@H](N(CC1)C)C)C KORCVBOCKBZMRD-MRXNPFEDSA-N 0.000 claims 1
- IUGRQCZGRNMZFV-MRXNPFEDSA-N 6-(2,6-dichlorophenyl)-2-[4-[(3R)-3-(hydroxymethyl)piperazin-1-yl]anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound CN1CN(C(=O)C2=C1N=C(NC1=CC=C(C=C1)N1CCN[C@@H](CO)C1)N=C2)C1=C(Cl)C=CC=C1Cl IUGRQCZGRNMZFV-MRXNPFEDSA-N 0.000 claims 1
- KUKFNHWJTHJNND-QGZVFWFLSA-N 6-(2,6-dichlorophenyl)-2-[4-[(3R)-3-(methoxymethyl)piperazin-1-yl]anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1C[C@@H](NCC1)COC)C KUKFNHWJTHJNND-QGZVFWFLSA-N 0.000 claims 1
- IXALLEROHFSSQQ-QGZVFWFLSA-N 6-(2,6-dichlorophenyl)-2-[4-[(3R)-3-methylpiperazin-1-yl]anilino]-8-(1-methylpyrazol-3-yl)-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1C[C@H](NCC1)C)C1=NN(C=C1)C IXALLEROHFSSQQ-QGZVFWFLSA-N 0.000 claims 1
- SWSGSQSHDZNOAH-IYBDPMFKSA-N 6-(2,6-dichlorophenyl)-2-[4-[(3R,5S)-3,5-dimethylpiperazin-1-yl]anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1C[C@H](N[C@H](C1)C)C)C SWSGSQSHDZNOAH-IYBDPMFKSA-N 0.000 claims 1
- IAXXZTIEOKTWAU-CALCHBBNSA-N 6-(2,6-dichlorophenyl)-2-[4-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-3-(hydroxymethyl)anilino]-8-ethyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1C[C@@H](N[C@@H](C1)C)C)CO)CC IAXXZTIEOKTWAU-CALCHBBNSA-N 0.000 claims 1
- WKVHJAMEXDRNPG-IYBDPMFKSA-N 6-(2,6-dichlorophenyl)-2-[4-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-3-(hydroxymethyl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1C[C@@H](N[C@@H](C1)C)C)CO)C WKVHJAMEXDRNPG-IYBDPMFKSA-N 0.000 claims 1
- DRTNGDRJMJDMGG-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[4-[2-(dimethylamino)acetyl]piperazin-1-yl]-3-(hydroxymethyl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCN(CC1)C(CN(C)C)=O)CO)C DRTNGDRJMJDMGG-UHFFFAOYSA-N 0.000 claims 1
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- NFMXSRRNFZGGLX-ROUUACIJSA-N 6-(2-chlorophenyl)-2-[4-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-methylanilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound CN1CN(C(=O)c2cnc(Nc3ccc(N4C[C@@H]5C[C@H]4CN5)c(C)c3)nc12)c1ccccc1Cl NFMXSRRNFZGGLX-ROUUACIJSA-N 0.000 claims 1
- ACWWOMUHDKZSOX-CALCHBBNSA-N 6-(2-chlorophenyl)-2-[4-[(3S,5R)-3,5-dimethylpiperazin-1-yl]anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C=CC=C1)N1CN(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1C[C@@H](N[C@@H](C1)C)C)C ACWWOMUHDKZSOX-CALCHBBNSA-N 0.000 claims 1
- YTNWMEBETLPQIB-UHFFFAOYSA-N 7,8-dihydro-6h-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C1=NC=C2C(=O)NCNC2=N1 YTNWMEBETLPQIB-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 229910052805 deuterium Inorganic materials 0.000 claims 1
- 125000004431 deuterium atom Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 102000020233 phosphotransferase Human genes 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1322602.2A GB201322602D0 (en) | 2013-12-19 | 2013-12-19 | Pharmaceutical compounds |
| EP14815843.9A EP3083625B1 (en) | 2013-12-19 | 2014-12-19 | Pyrimidopyrimidinones useful as wee-1 kinase inhibitors |
| PCT/GB2014/053793 WO2015092431A1 (en) | 2013-12-19 | 2014-12-19 | Pyrimidopyrimidinones useful as wee-1 kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI3083625T1 true SI3083625T1 (en) | 2018-03-30 |
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|---|---|---|---|
| SI201430580T SI3083625T1 (en) | 2013-12-19 | 2014-12-19 | Pyrimidopyrimidinones, useful as Wee-1 kinase inhibitors |
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| HR (1) | HRP20180080T1 (enExample) |
| HU (1) | HUE037908T2 (enExample) |
| IL (1) | IL245672B (enExample) |
| LT (1) | LT3083625T (enExample) |
| MX (1) | MX371108B (enExample) |
| NO (1) | NO3083625T3 (enExample) |
| NZ (1) | NZ720178A (enExample) |
| PL (1) | PL3083625T3 (enExample) |
| PT (1) | PT3083625T (enExample) |
| RS (1) | RS56731B1 (enExample) |
| RU (1) | RU2691105C1 (enExample) |
| SG (1) | SG11201603814TA (enExample) |
| SI (1) | SI3083625T1 (enExample) |
| SM (1) | SMT201800020T1 (enExample) |
| WO (1) | WO2015092431A1 (enExample) |
| ZA (1) | ZA201603337B (enExample) |
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| CN108137593B (zh) * | 2015-04-21 | 2021-01-05 | 上海交通大学医学院附属瑞金医院 | 蛋白激酶抑制剂的制备和用途 |
| AU2016344040B2 (en) * | 2015-11-01 | 2020-12-10 | The Regents Of The University Of Colorado, A Body Corporate | Wee 1 kinase inhibitors and methods of making and using the same |
| CA3043945A1 (en) | 2016-11-16 | 2018-05-24 | Sui Xiong Cai | 8,9-dihydroimidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6h)-ones |
| EP3564232B1 (en) | 2016-12-27 | 2022-01-26 | Riken | Bmp-signal-inhibiting compound |
| JP6717457B2 (ja) * | 2017-01-23 | 2020-07-01 | シージャーズォアン サガシティ ニュー ドラッグ デベロップメント カンパニー リミテッド | Ｗｅｅ１阻害剤としての１，２−ジヒドロ−３Ｈ−ピラゾロ［３，４−ｄ］ピリミジン−３−オン誘導体 |
| GB201703881D0 (en) * | 2017-03-10 | 2017-04-26 | Almac Discovery Ltd | Pharmaceutical compounds |
| KR20190130621A (ko) | 2017-03-31 | 2019-11-22 | 시애틀 지네틱스, 인크. | Chk1 저해제와 wee1 저해제의 조합물 |
| WO2019011228A1 (zh) * | 2017-07-10 | 2019-01-17 | 上海瑛派药业有限公司 | 咪唑并[1,2-b]嘧啶并[4,5-d]哒嗪-5(6H)-酮类化合物及其应用 |
| 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 |
| CA3078945A1 (en) | 2017-10-09 | 2019-04-18 | Nuvation Bo Inc. | Heterocyclic compounds and uses thereof |
| EP3694861A4 (en) | 2017-10-09 | 2021-05-19 | Nuvation Bio Inc. | HETEROCYCLIC COMPOUNDS AND USES THEREOF |
| EP3712150B1 (en) | 2017-11-01 | 2024-06-12 | Wuxi Biocity Biopharmaceutics Co., Ltd. | Macrocyclic compound serving as wee1 inhibitor and applications thereof |
| CA3088997A1 (en) | 2018-02-28 | 2019-09-06 | The Regents Of The University Of Colorado, A Body Corporate | Wee1 kinase inhibitors and methods of treating cancer using the same |
| WO2020063788A1 (zh) * | 2018-09-27 | 2020-04-02 | 贝达药业股份有限公司 | Fgfr4抑制剂及其应用 |
| JP7481336B2 (ja) | 2018-10-26 | 2024-05-10 | ウーシー・バイオシティ・バイオファーマシューティクス・カンパニー・リミテッド | Ｗｅｅ１阻害剤としてのピリミドピラゾロン類誘導体及びその使用 |
| EP3902805A4 (en) | 2018-12-28 | 2023-03-01 | SPV Therapeutics Inc. | CYCLINE-DEPENDENT KINASE INHIBITORS |
| CN113614087B (zh) | 2019-03-22 | 2023-06-02 | 首药控股(北京)股份有限公司 | Wee1抑制剂及其制备和用途 |
| JP2022526831A (ja) | 2019-04-09 | 2022-05-26 | ニューベイション・バイオ・インコーポレイテッド | ヘテロ環式化合物およびその使用 |
| EP3952879A4 (en) * | 2019-04-09 | 2023-01-04 | Nuvation Bio Inc. | HETEROCYCLIC COMPOUNDS AND THEIR USES |
| EP3952878A4 (en) * | 2019-04-09 | 2023-01-04 | Nuvation Bio Inc. | HETEROCYCLIC COMPOUNDS AND THEIR USES |
| LT3964510T (lt) | 2019-04-30 | 2024-08-12 | Wuxi Biocity Biopharmaceutics Co., Ltd. | Wee1 inhibitorinio junginio kristalinė forma ir jos panaudojimas |
| CN112142763B (zh) * | 2019-06-28 | 2024-01-26 | 上海医药集团股份有限公司 | 一种吡唑酮并嘧啶类化合物、其制备方法及应用 |
| AU2021290701A1 (en) | 2020-06-17 | 2023-02-02 | Wigen Biomedicine Technology (shanghai) Co., Ltd. | Pyrazolo(3,4-d)pyrimidine-3-ketone derivative as Wee-1 inhibitor |
| WO2022072336A1 (en) * | 2020-10-01 | 2022-04-07 | University Of Washington | Drug-like molecules and methods for the therapeutic targeting of microrna-21 |
| US12551584B1 (en) | 2020-12-07 | 2026-02-17 | Actinium Pharmaceuticals, Inc. | Lewis Y radioimmunotherapy for the treatment of cancer |
| MX2023007244A (es) * | 2020-12-18 | 2023-06-29 | Glaxosmithkline Ip Dev Ltd | Compuestos quimicos utiles para inhibir los canales de sodio activados por voltaje de nav1.8 y tratar las enfermedades mediadas por nav1.8. |
| EP4263540A1 (en) * | 2020-12-18 | 2023-10-25 | GlaxoSmithKline Intellectual Property Development Limited | Nitrogen containing 2,3-dihydroquinazolinone compounds as nav1.8 inhibitors |
| EP4332104A4 (en) | 2021-04-30 | 2025-04-16 | Wigen Biomedicine Technology (Shanghai) Co., Ltd. | Fused ring compound as a WEE-1 inhibitor, as well as production process and use thereof |
| EP4361153A4 (en) | 2021-06-25 | 2025-07-02 | Korea Res Inst Chemical Tech | NOVEL BIFUNCTIONAL HETEROCYCLIC COMPOUND HAVING BTK DEGRADATION FUNCTION VIA UBIQUITIN PROTEASOME PATHWAY, AND USE THEREOF |
| 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 |
| CN116836184B (zh) * | 2022-03-25 | 2025-07-25 | 药雅科技(上海)有限公司 | Wee1激酶抑制剂的制备及其应用 |
| WO2023217201A2 (zh) * | 2022-05-10 | 2023-11-16 | 杭州德睿智药科技有限公司 | 作为Wee1抑制剂的新型嘧啶并杂环类新化合物及其应用 |
| 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 |
| WO2025101691A1 (en) | 2023-11-08 | 2025-05-15 | Exelixis, Inc. | Methods for treating cancer using compounds that inhibit pkmyt1 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7504396B2 (en) | 2003-06-24 | 2009-03-17 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
| EP1727819A1 (en) | 2004-03-15 | 2006-12-06 | F.Hoffmann-La Roche Ag | Novel dichloro-phenyl-pyrido¬2,3-d|pyrimidine derivatives, their manufacture and use as pharmaceutical agents |
| FR2896246B1 (fr) | 2006-01-13 | 2008-08-15 | Sanofi Aventis Sa | Derives de pyrido-pyrimidone, leur preparation, leur application en therapeutique. |
| PE20080695A1 (es) | 2006-04-27 | 2008-06-28 | Banyu Pharma Co Ltd | Derivados de dihidropirazolopirimidinona como inhibidores de quinasa weel |
| JP5411847B2 (ja) | 2007-04-25 | 2014-02-12 | Ｍｓｄ株式会社 | Ｗｅｅｌキナーゼインヒビターとしてのジヒドロピラゾロピリミジノン誘導体の多形 |
| PL2168966T3 (pl) | 2007-06-15 | 2017-06-30 | Msd K.K. | Pochodna bicykloaniliny |
| EP2213673B1 (en) | 2007-10-23 | 2013-06-05 | Msd K.K. | Pyridone-substituted-dihydropyrazolopyrimidinone derivative |
| CA2745970A1 (en) | 2008-12-12 | 2010-06-17 | Msd K.K. | Dihydropyrimidopyrimidine derivative |
| EP2376494A4 (en) | 2008-12-12 | 2012-07-11 | Msd Kk | DIHYDROPYRIMIDOPYRIMIDINDERIVATE |
| US8637536B2 (en) * | 2010-12-06 | 2014-01-28 | Glaxo Group Limited | Pyrimidinone compounds for use in the treatment of diseases or conditions mediated by Lp-PLA2 |
| AR084515A1 (es) | 2010-12-22 | 2013-05-22 | Merz Pharma Gmbh & Co Kgaa | Derivados heterociclicos nitrogenados, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento de enfermedades asociadas al sistema nervioso central tales como parkinson y alzheimer, entre otras |
| TWI532742B (zh) | 2011-02-28 | 2016-05-11 | 艾伯維有限公司 | 激酶之三環抑制劑 |
| EP2731953A1 (en) | 2011-07-15 | 2014-05-21 | Abbvie Inc. | Tricyclic inhibitors of kinases useful for the treatment of proliferative diseases |
| WO2013013031A1 (en) | 2011-07-19 | 2013-01-24 | Abbvie Inc. | Pyridazino [4, 5 -d] pyrimidin- (6h) -one inhibitors of wee - 1 kinase |
| JP2014530867A (ja) | 2011-10-20 | 2014-11-20 | アッヴィ・インコーポレイテッド | キナーゼのピリドピリミジノン阻害剤 |
| EP2817308B1 (en) | 2012-02-23 | 2016-09-07 | AbbVie Inc. | Pyridopyrimidinone inhibitors of kinases |
| CN102816164A (zh) * | 2012-08-31 | 2012-12-12 | 北京理工大学 | 一种合成7-氨基-2,3-二氢嘧啶[4,5-d]嘧啶-4(1H)-酮的方法 |
-
2013
- 2013-12-19 GB GBGB1322602.2A patent/GB201322602D0/en not_active Ceased
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2014
- 2014-12-19 ES ES14815843.9T patent/ES2650013T3/es active Active
- 2014-12-19 US US15/105,869 patent/US9850247B2/en active Active
- 2014-12-19 KR KR1020167019551A patent/KR102405462B1/ko active Active
- 2014-12-19 HU HUE14815843A patent/HUE037908T2/hu unknown
- 2014-12-19 JP JP2016541294A patent/JP6437559B2/ja active Active
- 2014-12-19 CA CA2933755A patent/CA2933755C/en active Active
- 2014-12-19 MX MX2016007801A patent/MX371108B/es active IP Right Grant
- 2014-12-19 NZ NZ720178A patent/NZ720178A/en unknown
- 2014-12-19 HR HRP20180080TT patent/HRP20180080T1/hr unknown
- 2014-12-19 SG SG11201603814TA patent/SG11201603814TA/en unknown
- 2014-12-19 RS RS20171338A patent/RS56731B1/sr unknown
- 2014-12-19 BR BR112016014151-2A patent/BR112016014151B1/pt active IP Right Grant
- 2014-12-19 SM SM20180020T patent/SMT201800020T1/it unknown
- 2014-12-19 NO NO14815843A patent/NO3083625T3/no unknown
- 2014-12-19 WO PCT/GB2014/053793 patent/WO2015092431A1/en not_active Ceased
- 2014-12-19 LT LTEP14815843.9T patent/LT3083625T/lt unknown
- 2014-12-19 PT PT148158439T patent/PT3083625T/pt unknown
- 2014-12-19 CN CN201480069437.9A patent/CN105829315B/zh active Active
- 2014-12-19 PL PL14815843T patent/PL3083625T3/pl unknown
- 2014-12-19 DK DK14815843.9T patent/DK3083625T3/en active
- 2014-12-19 AU AU2014369457A patent/AU2014369457B2/en active Active
- 2014-12-19 SI SI201430580T patent/SI3083625T1/en unknown
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- 2014-12-19 RU RU2016123363A patent/RU2691105C1/ru active
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2016
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2018
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