RU2691105C1 - Лекарственные соединения - Google Patents

Info

Publication number

RU2691105C1

RU2691105C1 RU2016123363A RU2016123363A RU2691105C1 RU 2691105 C1 RU2691105 C1 RU 2691105C1 RU 2016123363 A RU2016123363 A RU 2016123363A RU 2016123363 A RU2016123363 A RU 2016123363A RU 2691105 C1 RU2691105 C1 RU 2691105C1

Authority

RU

Russia

Prior art keywords

methyl

amino

dihydropyrimido

phenyl

dichlorophenyl

Prior art date

2013-12-19

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 468
• -1 methoxyphenyl group Chemical group 0.000 claims abstract description 292
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 74
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 48
• 125000005843 halogen group Chemical group 0.000 claims abstract description 42
• 150000003839 salts Chemical class 0.000 claims abstract description 42
• 125000006413 ring segment Chemical group 0.000 claims abstract description 41
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 34
• 201000011510 cancer Diseases 0.000 claims abstract description 33
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 33
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 33
• 125000003277 amino group Chemical group 0.000 claims abstract description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 22
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 21
• 239000003814 drug Substances 0.000 claims abstract description 21
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 21
• 230000000694 effects Effects 0.000 claims abstract description 20
• 229910052805 deuterium Inorganic materials 0.000 claims abstract description 18
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 15
• 229940079593 drug Drugs 0.000 claims abstract description 14
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 5
• 125000004434 sulfur atom Chemical group 0.000 claims abstract description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 4
• 239000001257 hydrogen Substances 0.000 claims abstract description 4
• 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims abstract 6
• 230000001404 mediated effect Effects 0.000 claims abstract 6
• 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims abstract 6
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 3
• 125000005277 alkyl imino group Chemical group 0.000 claims abstract 2
• 125000003375 sulfoxide group Chemical group 0.000 claims abstract 2
• 238000000034 method Methods 0.000 claims description 499
• 125000001424 substituent group Chemical group 0.000 claims description 35
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 31
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 16
• 238000011282 treatment Methods 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 239000003112 inhibitor Substances 0.000 claims description 11
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 10
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 10
• PPGWAKHCMDIJCZ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-(4-piperazin-1-ylanilino)-7h-pyrimido[4,5-d]pyrimidin-5-one Chemical compound N1=C2N(C)CN(C=3C(=CC=CC=3Cl)Cl)C(=O)C2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 PPGWAKHCMDIJCZ-UHFFFAOYSA-N 0.000 claims description 9
• 238000002560 therapeutic procedure Methods 0.000 claims description 9
• 230000002265 prevention Effects 0.000 claims description 8
• 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 description 6
• LBMRQLZAIMKGES-OAHLLOKOSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[4-[(3R)-3-methylpiperazin-1-yl]anilino]-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C[C@@H]1CN(CCN1)C1=CC=C(NC2=NC3=C(C=N2)C(=O)N(CN3C)C2=C(Cl)C=CC=C2Cl)C=C1 LBMRQLZAIMKGES-OAHLLOKOSA-N 0.000 claims description 6
• 102000001253 Protein Kinase Human genes 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 108060006633 protein kinase Proteins 0.000 claims description 6
• 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 description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• PPGWAKHCMDIJCZ-FNHLFAINSA-N 2,2-dideuterio-3-(2,6-dichlorophenyl)-1-methyl-7-(4-piperazin-1-ylanilino)pyrimido[4,5-d]pyrimidin-4-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1C(N(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1CCNCC1)C)([2H])[2H] PPGWAKHCMDIJCZ-FNHLFAINSA-N 0.000 claims description 4
• GPODLJVUNGVXNJ-UHFFFAOYSA-N 2-[4-(3,8-diazabicyclo[3.2.1]octan-3-yl)anilino]-6-(2,6-dichlorophenyl)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C12CN(CC(CC1)N2)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(CN(C2=O)C1=C(C=CC=C1Cl)Cl)C GPODLJVUNGVXNJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 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 description 4
• UFIXLFHFBVKERS-OAHLLOKOSA-N 6-(2,6-dichlorophenyl)-2-[3-(hydroxymethyl)-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)CO)C UFIXLFHFBVKERS-OAHLLOKOSA-N 0.000 claims description 4
• 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 description 4
• KVQJFGGAQBGGCB-MRXNPFEDSA-N 6-(2,6-dichlorophenyl)-2-[3-(methoxymethyl)-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)COC)C KVQJFGGAQBGGCB-MRXNPFEDSA-N 0.000 claims description 4
• ZOKGXCGRFOEAGH-CQSZACIVSA-N 6-(2,6-dichlorophenyl)-2-[3-fluoro-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)F)C ZOKGXCGRFOEAGH-CQSZACIVSA-N 0.000 claims description 4
• AZJPOVYLWJNKEO-HNNXBMFYSA-N 6-(2,6-dichlorophenyl)-2-[3-fluoro-4-[(3S)-3-(hydroxymethyl)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)CO)F)C AZJPOVYLWJNKEO-HNNXBMFYSA-N 0.000 claims description 4
• ZFBXHAQPRJKCAF-KRWDZBQOSA-N 6-(2,6-dichlorophenyl)-2-[4-[(2S)-2-(hydroxymethyl)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)N1[C@@H](CNCC1)CO)C ZFBXHAQPRJKCAF-KRWDZBQOSA-N 0.000 claims description 4
• 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 description 4
• 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 description 4
• 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 description 4
• KUKFNHWJTHJNND-KRWDZBQOSA-N 6-(2,6-dichlorophenyl)-2-[4-[(3S)-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-KRWDZBQOSA-N 0.000 claims description 4
• IUUBRYQHJICSNC-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-7,8-dimethyl-2-(4-piperazin-1-ylanilino)-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1C(N(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1CCNCC1)C)C IUUBRYQHJICSNC-UHFFFAOYSA-N 0.000 claims description 4
• DYMIHMMQKGYANV-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC=C2CCNCC2=C1)C DYMIHMMQKGYANV-UHFFFAOYSA-N 0.000 claims description 4
• DQPLNKURCKBGJN-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-(4-piperidin-4-ylanilino)-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)C DQPLNKURCKBGJN-UHFFFAOYSA-N 0.000 claims description 4
• MNKSIPFQQMPRHB-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-(4-piperidin-4-yloxyanilino)-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)OC1CCNCC1)C MNKSIPFQQMPRHB-UHFFFAOYSA-N 0.000 claims description 4
• FAIFKBRNZILADG-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[3-(methylaminomethyl)-4-morpholin-4-ylanilino]-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound CNCC1=C(C=CC(NC2=NC3=C(C=N2)C(=O)N(CN3C)C2=C(Cl)C=CC=C2Cl)=C1)N1CCOCC1 FAIFKBRNZILADG-UHFFFAOYSA-N 0.000 claims description 4
• WIBUEQHFXZMHSQ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[4-(3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl)anilino]-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C12COCC(CN(C1)C1=CC=C(C=C1)NC1=NC=C3C(=N1)N(CN(C3=O)C1=C(C=CC=C1Cl)Cl)C)N2 WIBUEQHFXZMHSQ-UHFFFAOYSA-N 0.000 claims description 4
• ZZMUGJXRVBUPIZ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[4-(methylsulfonimidoyl)anilino]-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)S(=O)(=N)C)C ZZMUGJXRVBUPIZ-UHFFFAOYSA-N 0.000 claims description 4
• LBMRQLZAIMKGES-HNNXBMFYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[4-[(3S)-3-methylpiperazin-1-yl]anilino]-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C[C@H]1CN(CCN1)C1=CC=C(NC2=NC3=C(C=N2)C(=O)N(CN3C)C2=C(Cl)C=CC=C2Cl)C=C1 LBMRQLZAIMKGES-HNNXBMFYSA-N 0.000 claims description 4
• LMZQNYTZDCZDNB-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-2-[4-[3-(trifluoromethyl)piperazin-1-yl]anilino]-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(F)(F)F)C LMZQNYTZDCZDNB-UHFFFAOYSA-N 0.000 claims description 4
• XLLRCHIYUAZPPN-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-methyl-7-phenyl-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1C(N(C2=NC(=NC=C2C1=O)NC1=CC=C2CCNCC2=C1)C)C1=CC=CC=C1 XLLRCHIYUAZPPN-UHFFFAOYSA-N 0.000 claims description 4
• QZRCPZQLJJSRKH-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-8-methyl-2-(4-piperazin-1-ylanilino)-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound ClC1=C(C(=CC=C1)F)N1CN(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1CCNCC1)C QZRCPZQLJJSRKH-UHFFFAOYSA-N 0.000 claims description 4
• ZSQBZADJUMJJAA-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(4-piperazin-1-ylanilino)-2,7,11,13-tetrazatricyclo[7.4.0.02,6]trideca-1(13),9,11-trien-8-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1C2N(C3=C(C1=O)C=NC(=N3)NC1=CC=C(C=C1)N1CCNCC1)CCC2 ZSQBZADJUMJJAA-UHFFFAOYSA-N 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• ZYBNOUONCCPKEN-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)-3-(methylaminomethyl)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)CNC ZYBNOUONCCPKEN-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• RSZDSSUZZYDOFU-RDJZCZTQSA-N 2-[4-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]anilino]-6-(2,6-dichlorophenyl)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound CN1CN(C(=O)c2cnc(Nc3ccc(cc3)N3C[C@@H]4C[C@H]3CN4)nc12)c1c(Cl)cccc1Cl RSZDSSUZZYDOFU-RDJZCZTQSA-N 0.000 claims description 3
• SAZDTUOVUDPTJS-IBGZPJMESA-N 2-[4-[(9aS)-3,4,6,7,9,9a-hexahydro-1H-pyrazino[2,1-c][1,4]oxazin-8-yl]-3-(hydroxymethyl)anilino]-6-(2,6-dichlorophenyl)-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]2COCCN2CC1)CO)C SAZDTUOVUDPTJS-IBGZPJMESA-N 0.000 claims description 3
• TXSMTMZSKXXHFO-UHFFFAOYSA-N 2-[4-[4-(2-aminoacetyl)piperazin-1-yl]anilino]-6-(2,6-dichlorophenyl)-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound NCC(=O)N1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(CN(C2=O)C1=C(C=CC=C1Cl)Cl)C TXSMTMZSKXXHFO-UHFFFAOYSA-N 0.000 claims description 3
• ZLUXROJDIBWCSL-UHFFFAOYSA-N 5-[[6-(2,6-dichlorophenyl)-8-methyl-5-oxo-7H-pyrimido[4,5-d]pyrimidin-2-yl]amino]-2-piperazin-1-ylbenzonitrile Chemical compound ClC1=C(C(=CC=C1)Cl)N1CN(C2=NC(=NC=C2C1=O)NC1=CC(=C(C=C1)N1CCNCC1)C#N)C ZLUXROJDIBWCSL-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• SAVKMENYJBWNHC-CQSZACIVSA-N 6-(2,6-dichlorophenyl)-2-[2-fluoro-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=C(C=C(C=C1)N1C[C@H](NCC1)C)F)C SAVKMENYJBWNHC-CQSZACIVSA-N 0.000 claims description 3
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• 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
• WXPACIAVXGHKPJ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-(hydroxymethyl)-4-(1-methylpiperidin-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)C1CCN(CC1)C)CO)C WXPACIAVXGHKPJ-UHFFFAOYSA-N 0.000 claims 1
• ICUCQOGIMUELDJ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-(hydroxymethyl)-4-(3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl)anilino]-8-methyl-7H-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C12COCC(CN(C1)C1=C(C=C(C=C1)NC1=NC=C3C(=N1)N(CN(C3=O)C1=C(C=CC=C1Cl)Cl)C)CO)N2 ICUCQOGIMUELDJ-UHFFFAOYSA-N 0.000 claims 1
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• RXFFNESXLYNPLX-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-(hydroxymethyl)-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)CO)C RXFFNESXLYNPLX-UHFFFAOYSA-N 0.000 claims 1
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• 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
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