JP2012514601A5 - - Google Patents
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- JP2012514601A5 JP2012514601A5 JP2011544638A JP2011544638A JP2012514601A5 JP 2012514601 A5 JP2012514601 A5 JP 2012514601A5 JP 2011544638 A JP2011544638 A JP 2011544638A JP 2011544638 A JP2011544638 A JP 2011544638A JP 2012514601 A5 JP2012514601 A5 JP 2012514601A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimido
- diazepine
- methyl
- methoxy
- phenylamino
- 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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- -1 carbocycle Chemical group 0.000 claims 38
- 125000000217 alkyl group Chemical group 0.000 claims 34
- 125000003118 aryl group Chemical group 0.000 claims 27
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 21
- 125000001072 heteroaryl group Chemical group 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000000547 substituted alkyl group Chemical group 0.000 claims 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 11
- 150000002148 esters Chemical class 0.000 claims 9
- 239000000651 prodrug Substances 0.000 claims 9
- 229940002612 prodrug Drugs 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- PKVNVXXWANAAFP-UHFFFAOYSA-N 1,7-dihydro-1,4-diazepin-6-one Chemical compound O=C1CNC=CN=C1 PKVNVXXWANAAFP-UHFFFAOYSA-N 0.000 claims 3
- AZQDLBJZOAHSAZ-UHFFFAOYSA-N 1,7-dihydrodiazepin-6-one Chemical compound O=C1CNN=CC=C1 AZQDLBJZOAHSAZ-UHFFFAOYSA-N 0.000 claims 3
- 101000950687 Homo sapiens Mitogen-activated protein kinase 7 Proteins 0.000 claims 3
- 102100037805 Mitogen-activated protein kinase 7 Human genes 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- BUBBBFSEOYHUQA-UHFFFAOYSA-N 2,5-dihydrooxazepin-6-one Chemical compound O1NC=CCC(C1)=O BUBBBFSEOYHUQA-UHFFFAOYSA-N 0.000 claims 2
- VVPYTOVXFOGRIN-UHFFFAOYSA-N 2-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=CC=C4C(=O)N(C)C3=CN=2)C(OC)=CC=1N(CC1)CCC1N1CCN(C)CC1 VVPYTOVXFOGRIN-UHFFFAOYSA-N 0.000 claims 2
- LZNDHLKMOBVBFV-UHFFFAOYSA-N 4-[(2-cyclopentyl-9-methyl-8-oxo-2,9,12,14-tetrazatricyclo[8.4.0.03,7]tetradeca-1(14),10,12-trien-13-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC=C1NC1=NC=C(N(C)C(=O)C2C(CCC2)N2C3CCCC3)C2=N1 LZNDHLKMOBVBFV-UHFFFAOYSA-N 0.000 claims 2
- 101100268648 Mus musculus Abl1 gene Proteins 0.000 claims 2
- QAPAJIZPZGWAND-UHFFFAOYSA-N XMD8-92 Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=CC=C4C(=O)N(C)C3=CN=2)C(OCC)=CC=1N1CCC(O)CC1 QAPAJIZPZGWAND-UHFFFAOYSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims 1
- NFNBVXVXMQZSGB-UHFFFAOYSA-N 11-cyclopentyl-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5-methylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C1=CC=CC=C1N2C1CCCC1 NFNBVXVXMQZSGB-UHFFFAOYSA-N 0.000 claims 1
- JGVXSQJYBQAPAE-UHFFFAOYSA-N 11-ethyl-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5-methylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound N1=C2N(CC)C3=CC=CC=C3C(=O)N(C)C2=CN=C1NC(C(=C1)OC)=CC=C1N1CCN(C)CC1 JGVXSQJYBQAPAE-UHFFFAOYSA-N 0.000 claims 1
- ASAFHHFHFUCJHM-UHFFFAOYSA-N 11-methyl-2-[4-(4-methylpiperazin-1-yl)-2-propan-2-yloxyanilino]-5h-pyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=CC=C4C(=O)NC3=CN=2)C(OC(C)C)=CC=1N1CCN(C)CC1 ASAFHHFHFUCJHM-UHFFFAOYSA-N 0.000 claims 1
- LHBAORXBTTWPDF-UHFFFAOYSA-N 2-[2-ethoxy-4-(4-hydroxypiperidin-1-yl)anilino]-5-methyl-9-phenyl-7,8-dihydropyrimido[4,5-b][1,4]diazepin-6-one Chemical compound CCOC1=CC(N2CCC(O)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)CCN2C1=CC=CC=C1 LHBAORXBTTWPDF-UHFFFAOYSA-N 0.000 claims 1
- DDTPGANIPBKTNU-UHFFFAOYSA-N 2-[2-methoxy-4-(4-methyl-1-piperazinyl)anilino]-5,11-dimethyl-6-pyrimido[4,5-b][1,4]benzodiazepinone Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=CC=C4C(=O)N(C)C3=CN=2)C(OC)=CC=1N1CCN(C)CC1 DDTPGANIPBKTNU-UHFFFAOYSA-N 0.000 claims 1
- KXCGZEPWZFXPSC-UHFFFAOYSA-N 2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-4,11-dimethyl-5h-pyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=CC=C4C(=O)NC3=C(C)N=2)C(OC)=CC=1N1CCN(C)CC1 KXCGZEPWZFXPSC-UHFFFAOYSA-N 0.000 claims 1
- OXTSNXXVWGKOMB-UHFFFAOYSA-N 2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-4,5,11-trimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=CC=C4C(=O)N(C)C3=C(C)N=2)C(OC)=CC=1N1CCN(C)CC1 OXTSNXXVWGKOMB-UHFFFAOYSA-N 0.000 claims 1
- WBPCKVJWZORAAO-UHFFFAOYSA-N 2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5,11-dihydropyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3NC4=CC=CC=C4C(=O)NC3=CN=2)C(OC)=CC=1N1CCN(C)CC1 WBPCKVJWZORAAO-UHFFFAOYSA-N 0.000 claims 1
- NYHLZQOMTUZDHV-UHFFFAOYSA-N 2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5,8,11-trimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=C(C)C=C4C(=O)N(C)C3=CN=2)C(OC)=CC=1N1CCN(C)CC1 NYHLZQOMTUZDHV-UHFFFAOYSA-N 0.000 claims 1
- YYTFTZONXCQXLW-UHFFFAOYSA-N 2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5-methyl-11-propan-2-ylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C(C)C)C4=CC=CC=C4C(=O)N(C)C3=CN=2)C(OC)=CC=1N1CCN(C)CC1 YYTFTZONXCQXLW-UHFFFAOYSA-N 0.000 claims 1
- GTCWEOILNAZCDT-UHFFFAOYSA-N 2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5-methyl-11h-pyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3NC4=CC=CC=C4C(=O)N(C)C3=CN=2)C(OC)=CC=1N1CCN(C)CC1 GTCWEOILNAZCDT-UHFFFAOYSA-N 0.000 claims 1
- NTRCYAXJQIZACU-UHFFFAOYSA-N 2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5-methylpyrimido[4,5-b][1,4]benzothiazepin-6-one Chemical compound C=1C=C(NC=2N=C3SC4=CC=CC=C4C(=O)N(C)C3=CN=2)C(OC)=CC=1N1CCN(C)CC1 NTRCYAXJQIZACU-UHFFFAOYSA-N 0.000 claims 1
- OGHDOVJGVKNHRQ-UHFFFAOYSA-N 2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5h-pyrimido[4,5-b][1,4]benzothiazepin-6-one Chemical compound C=1C=C(NC=2N=C3SC4=CC=CC=C4C(=O)NC3=CN=2)C(OC)=CC=1N1CCN(C)CC1 OGHDOVJGVKNHRQ-UHFFFAOYSA-N 0.000 claims 1
- KBULREVCYROFNX-UHFFFAOYSA-N 2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-8,11-dimethyl-5h-pyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=C(C)C=C4C(=O)NC3=CN=2)C(OC)=CC=1N1CCN(C)CC1 KBULREVCYROFNX-UHFFFAOYSA-N 0.000 claims 1
- HQHQZEUABJAAMZ-UHFFFAOYSA-N 2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-9-phenyl-7,8-dihydro-5h-pyrimido[4,5-b][1,4]diazepin-6-one Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1NC(=O)CCN2C1=CC=CC=C1 HQHQZEUABJAAMZ-UHFFFAOYSA-N 0.000 claims 1
- UDMGPKXTQNCFIO-UHFFFAOYSA-N 2-[2-methoxy-4-(4-methylpiperazine-1-carbonyl)anilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=CC=C4C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)N1CCN(C)CC1 UDMGPKXTQNCFIO-UHFFFAOYSA-N 0.000 claims 1
- XYKSVLLNDQRZDK-UHFFFAOYSA-N 2-[2-methoxy-5-[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]anilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C1=C(NC=2N=C3N(C)C4=CC=CC=C4C(=O)N(C)C3=CN=2)C(OC)=CC=C1C(=O)N(CC1)CCC1N1CCN(C)CC1 XYKSVLLNDQRZDK-UHFFFAOYSA-N 0.000 claims 1
- YSFFGUHMDPYPAW-UHFFFAOYSA-N 2-[4-(4-hydroxypiperidin-1-yl)-2-methoxyanilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=CC=C4C(=O)N(C)C3=CN=2)C(OC)=CC=1N1CCC(O)CC1 YSFFGUHMDPYPAW-UHFFFAOYSA-N 0.000 claims 1
- NPRYKZQCTXZUKH-UHFFFAOYSA-N 2-[4-(4-hydroxypiperidin-1-yl)-2-propan-2-yloxyanilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=CC=C4C(=O)N(C)C3=CN=2)C(OC(C)C)=CC=1N1CCC(O)CC1 NPRYKZQCTXZUKH-UHFFFAOYSA-N 0.000 claims 1
- NGXGUOYOCNOKJO-UHFFFAOYSA-N 2-[4-(4-hydroxypiperidin-1-yl)-2-propan-2-yloxyanilino]-5-methyl-9-phenyl-7,8-dihydropyrimido[4,5-b][1,4]diazepin-6-one Chemical compound CC(C)OC1=CC(N2CCC(O)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)CCN2C1=CC=CC=C1 NGXGUOYOCNOKJO-UHFFFAOYSA-N 0.000 claims 1
- RUSIEYRQPZZDCO-UHFFFAOYSA-N 2-[4-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-2-methoxyanilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=CC=C4C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)N1CCN(CCO)CC1 RUSIEYRQPZZDCO-UHFFFAOYSA-N 0.000 claims 1
- YMOOMBLIPWGVAG-UHFFFAOYSA-N 2-[[5-(4-hydroxypiperidin-1-yl)pyridin-2-yl]amino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound N1=C2N(C)C3=CC=CC=C3C(=O)N(C)C2=CN=C1NC(N=C1)=CC=C1N1CCC(O)CC1 YMOOMBLIPWGVAG-UHFFFAOYSA-N 0.000 claims 1
- FMJVGPKPZYQCHQ-UHFFFAOYSA-N 2-cyclopentyl-13-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-9-methyl-2,9,12,14-tetrazatricyclo[8.4.0.03,7]tetradeca-1(14),10,12-trien-8-one Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C1CCCC1N2C1CCCC1 FMJVGPKPZYQCHQ-UHFFFAOYSA-N 0.000 claims 1
- FWCFYOYWYWAYRZ-UHFFFAOYSA-N 2-cyclopentyl-13-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]-9-methyl-2,9,12,14-tetrazatricyclo[8.4.0.03,7]tetradeca-1(14),10,12-trien-8-one Chemical compound COC1=CC(N2CCC(CC2)N2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C1CCCC1N2C1CCCC1 FWCFYOYWYWAYRZ-UHFFFAOYSA-N 0.000 claims 1
- YXQSBQOOYOWCJL-UHFFFAOYSA-N 3-[(5,11-dimethyl-6-oxopyrimido[4,5-b][1,4]benzodiazepin-2-yl)amino]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1NC1=NC=C(N(C)C(=O)C=2C(=CC=CC=2)N2C)C2=N1 YXQSBQOOYOWCJL-UHFFFAOYSA-N 0.000 claims 1
- WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 claims 1
- XBWVKVCSCJYKTP-UHFFFAOYSA-N 4-[(2-cyclopentyl-9-methyl-8-oxo-2,9,12,14-tetrazatricyclo[8.4.0.03,7]tetradeca-1(14),10,12-trien-13-yl)amino]-3-methoxy-N-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C2C(CCC2)N2C3CCCC3)C2=N1 XBWVKVCSCJYKTP-UHFFFAOYSA-N 0.000 claims 1
- REFAILJSNNDVNL-UHFFFAOYSA-N 4-[(2-cyclopentyl-9-methyl-8-oxo-2,9,12,14-tetrazatricyclo[8.4.0.03,7]tetradeca-1(14),10,12-trien-13-yl)amino]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1NC1=NC=C(N(C)C(=O)C2C(CCC2)N2C3CCCC3)C2=N1 REFAILJSNNDVNL-UHFFFAOYSA-N 0.000 claims 1
- WSLOEKAMNQLCHA-UHFFFAOYSA-N 4-[(5,11-dimethyl-6-oxopyrimido[4,5-b][1,4]benzodiazepin-2-yl)amino]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1NC1=NC=C(N(C)C(=O)C=2C(=CC=CC=2)N2C)C2=N1 WSLOEKAMNQLCHA-UHFFFAOYSA-N 0.000 claims 1
- JFRNFMQDZRWAQB-UHFFFAOYSA-N 4-[(9-cyclopentyl-5-methyl-6-oxo-7,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)CCN2C1CCCC1 JFRNFMQDZRWAQB-UHFFFAOYSA-N 0.000 claims 1
- YPTCBEGMGVTHLV-UHFFFAOYSA-N 4-[(9-cyclopentyl-6-oxo-7,8-dihydro-5h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1NC(=O)CCN2C1CCCC1 YPTCBEGMGVTHLV-UHFFFAOYSA-N 0.000 claims 1
- 102100022681 40S ribosomal protein S27 Human genes 0.000 claims 1
- HGOKWKGWPGOSCA-UHFFFAOYSA-N 5-ethyl-2-[4-(4-hydroxypiperidin-1-yl)-2-methoxyanilino]-11-methylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound N1=C2N(C)C3=CC=CC=C3C(=O)N(CC)C2=CN=C1NC(C(=C1)OC)=CC=C1N1CCC(O)CC1 HGOKWKGWPGOSCA-UHFFFAOYSA-N 0.000 claims 1
- UJDYKWMGSWQRHC-UHFFFAOYSA-N 5-ethyl-2-[[5-(4-hydroxypiperidin-1-yl)pyridin-2-yl]amino]-11-methylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound N1=C2N(C)C3=CC=CC=C3C(=O)N(CC)C2=CN=C1NC(N=C1)=CC=C1N1CCC(O)CC1 UJDYKWMGSWQRHC-UHFFFAOYSA-N 0.000 claims 1
- NGLWEPBNFIVDCQ-UHFFFAOYSA-N 6-[(2-cyclopentyl-9-methyl-8-oxo-2,9,12,14-tetrazatricyclo[8.4.0.03,7]tetradeca-1(14),10,12-trien-13-yl)amino]-N-methylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C2C(CCC2)N2C3CCCC3)C2=N1 NGLWEPBNFIVDCQ-UHFFFAOYSA-N 0.000 claims 1
- MUKRTRBUCKPVNQ-UHFFFAOYSA-N 8-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-11-methyl-5h-pyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=C(Cl)C=C4C(=O)NC3=CN=2)C(OC)=CC=1N1CCN(C)CC1 MUKRTRBUCKPVNQ-UHFFFAOYSA-N 0.000 claims 1
- VHGSQSKYNALGRI-UHFFFAOYSA-N 8-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=C(Cl)C=C4C(=O)N(C)C3=CN=2)C(OC)=CC=1N1CCN(C)CC1 VHGSQSKYNALGRI-UHFFFAOYSA-N 0.000 claims 1
- RHSOYHKODVPGTH-UHFFFAOYSA-N 9-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC(Cl)=CC=C4C(=O)N(C)C3=CN=2)C(OC)=CC=1N1CCN(C)CC1 RHSOYHKODVPGTH-UHFFFAOYSA-N 0.000 claims 1
- ACHCMXBSPWFSTG-UHFFFAOYSA-N 9-cyclopentyl-2-[2-ethoxy-4-(4-hydroxypiperidin-1-yl)anilino]-5-ethyl-7,8-dihydropyrimido[4,5-b][1,4]diazepin-6-one Chemical compound CCOC1=CC(N2CCC(O)CC2)=CC=C1NC(N=C12)=NC=C1N(CC)C(=O)CCN2C1CCCC1 ACHCMXBSPWFSTG-UHFFFAOYSA-N 0.000 claims 1
- JPPAAAXZOZVWJV-UHFFFAOYSA-N 9-cyclopentyl-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5,8-dimethyl-7,8-dihydropyrimido[4,5-b][1,4]diazepin-6-one Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)CC(C)N2C1CCCC1 JPPAAAXZOZVWJV-UHFFFAOYSA-N 0.000 claims 1
- OJWZTBKXQCIUGC-UHFFFAOYSA-N 9-cyclopentyl-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-8-methyl-7,8-dihydro-5h-pyrimido[4,5-b][1,4]diazepin-6-one Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1NC(=O)CC(C)N2C1CCCC1 OJWZTBKXQCIUGC-UHFFFAOYSA-N 0.000 claims 1
- DIKJXQJRGJEYBE-UHFFFAOYSA-N 9-cyclopentyl-2-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]-5,8-dimethyl-7,8-dihydropyrimido[4,5-b][1,4]diazepin-6-one Chemical compound COC1=CC(N2CCC(CC2)N2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)CC(C)N2C1CCCC1 DIKJXQJRGJEYBE-UHFFFAOYSA-N 0.000 claims 1
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