JP2011527667A - ハロ置換ピリミドジアゼピン - Google Patents

Info

Publication number

JP2011527667A

JP2011527667A JP2011513994A JP2011513994A JP2011527667A JP 2011527667 A JP2011527667 A JP 2011527667A JP 2011513994 A JP2011513994 A JP 2011513994A JP 2011513994 A JP2011513994 A JP 2011513994A JP 2011527667 A JP2011527667 A JP 2011527667A

Authority

JP

Japan

Prior art keywords

methyl

tetrahydro

difluoro

pyrimido

oxo

Prior art date

2008-06-18

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• OHXQYFCNXHGKPJ-UHFFFAOYSA-N 1h-pyrimido[5,4-c]diazepine Chemical class N1N=CC=CC2=NC=NC=C12 OHXQYFCNXHGKPJ-UHFFFAOYSA-N 0.000 title 1
• 239000000203 mixture Substances 0.000 claims abstract description 506
• 150000001875 compounds Chemical class 0.000 claims abstract description 73
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims abstract description 6
• 201000010099 disease Diseases 0.000 claims abstract description 6
• 230000000771 oncological effect Effects 0.000 claims abstract description 6
• 206010006187 Breast cancer Diseases 0.000 claims abstract description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 5
• 206010009944 Colon cancer Diseases 0.000 claims abstract description 5
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims abstract description 5
• 206010060862 Prostate cancer Diseases 0.000 claims abstract description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 5
• 208000029742 colonic neoplasm Diseases 0.000 claims abstract description 5
• 201000005202 lung cancer Diseases 0.000 claims abstract description 5
• 208000020816 lung neoplasm Diseases 0.000 claims abstract description 5
• -1 — (CH 2 ) n -aryl Chemical group 0.000 claims description 383
• 125000000217 alkyl group Chemical group 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
• ZKMVETCPEOLGKX-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethylbenzoic acid Chemical compound CCC1=CC(C(O)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 ZKMVETCPEOLGKX-UHFFFAOYSA-N 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
• 125000001153 fluoro group Chemical group F* 0.000 claims description 16
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
• ZSJCKAGQFMQYPN-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=C(F)C=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 ZSJCKAGQFMQYPN-UHFFFAOYSA-N 0.000 claims description 13
• 238000000034 method Methods 0.000 claims description 13
• CMDYKXOHCXFFEY-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-(trifluoromethyl)benzoic acid Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC1=CC=C(C(O)=O)C=C1C(F)(F)F CMDYKXOHCXFFEY-UHFFFAOYSA-N 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• DKKARFAGKSXUOQ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethoxybenzoic acid Chemical compound CCOC1=CC(C(O)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 DKKARFAGKSXUOQ-UHFFFAOYSA-N 0.000 claims description 11
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 claims description 10
• MYXKWQBFWLFLRL-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methylbenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC1=CC=C(C(N)=O)C=C1C MYXKWQBFWLFLRL-UHFFFAOYSA-N 0.000 claims description 10
• APUDYQSELWZNKJ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methylbenzoic acid Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC1=CC=C(C(O)=O)C=C1C APUDYQSELWZNKJ-UHFFFAOYSA-N 0.000 claims description 10
• CRWJVMVXFUPDSV-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCC3)C2=N1 CRWJVMVXFUPDSV-UHFFFAOYSA-N 0.000 claims description 9
• DUMGSMIYUOAUKI-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]benzoic acid Chemical compound N1=C2N(C3CCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC1=CC=C(C(O)=O)C=C1 DUMGSMIYUOAUKI-UHFFFAOYSA-N 0.000 claims description 9
• AYZQTNNTQIVZBF-UHFFFAOYSA-N 4-[(9-cyclopentyl-5-ethyl-7,7-difluoro-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoic acid Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CC)C2=CN=C1NC1=CC=C(C(O)=O)C=C1OC AYZQTNNTQIVZBF-UHFFFAOYSA-N 0.000 claims description 9
• CIFKUDOYFQJFNR-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1NC1=NC=C(NC(=O)C(F)(F)CN2C3CCCC3)C2=N1 CIFKUDOYFQJFNR-UHFFFAOYSA-N 0.000 claims description 9
• PHHUAAGQVSFMPP-UHFFFAOYSA-N 4-[(9-cyclopentyl-5-ethyl-7,7-difluoro-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]benzoic acid Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CC)C2=CN=C1NC1=CC=C(C(O)=O)C=C1 PHHUAAGQVSFMPP-UHFFFAOYSA-N 0.000 claims description 8
• UBNNIDJLSKXXAD-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(NC(=O)C(F)(F)CN2C3CCCC3)C2=N1 UBNNIDJLSKXXAD-UHFFFAOYSA-N 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• BNUJZZKCRYZJRK-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5-propyl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]benzoic acid Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CCC)C2=CN=C1NC1=CC=C(C(O)=O)C=C1 BNUJZZKCRYZJRK-UHFFFAOYSA-N 0.000 claims description 7
• 239000002253 acid Substances 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• HBMAHAVOKSITSJ-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(oxan-4-yl)benzamide Chemical compound N1=C2N(C3CCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C=C1)=CC=C1C(=O)NC1CCOCC1 HBMAHAVOKSITSJ-UHFFFAOYSA-N 0.000 claims description 6
• AVOQOBYXRVYWBE-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-fluorobenzoic acid Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC1=CC=C(C(O)=O)C=C1F AVOQOBYXRVYWBE-UHFFFAOYSA-N 0.000 claims description 6
• SUBIEWLFZOKEFV-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]benzoic acid Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC1=CC=C(C(O)=O)C=C1 SUBIEWLFZOKEFV-UHFFFAOYSA-N 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• ZCBNVAGNECOCMF-UHFFFAOYSA-N tert-butyl 3-[[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]methyl]pyrrolidine-1-carboxylate Chemical compound COC1=CC(C(=O)NCC2CN(CC2)C(=O)OC(C)(C)C)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 ZCBNVAGNECOCMF-UHFFFAOYSA-N 0.000 claims description 6
• WUXFUFZPNVCASY-UHFFFAOYSA-N tert-butyl 4-[3-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]propyl]piperazine-1-carboxylate Chemical compound COC1=CC(C(=O)NCCCN2CCN(CC2)C(=O)OC(C)(C)C)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 WUXFUFZPNVCASY-UHFFFAOYSA-N 0.000 claims description 6
• UVIZGRDPUZKCBS-UHFFFAOYSA-N tert-butyl 4-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]piperidine-1-carboxylate Chemical compound COC1=CC(C(=O)NC2CCN(CC2)C(=O)OC(C)(C)C)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 UVIZGRDPUZKCBS-UHFFFAOYSA-N 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• CXNVFCSEWWAJON-UHFFFAOYSA-N 2-[4-(4-aminopiperidine-1-carbonyl)-2-methoxyanilino]-9-cyclobutyl-7,7-difluoro-5-methyl-8h-pyrimido[4,5-b][1,4]diazepin-6-one Chemical compound COC1=CC(C(=O)N2CCC(N)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCC1 CXNVFCSEWWAJON-UHFFFAOYSA-N 0.000 claims description 5
• IUJQPSWSRGBVJW-UHFFFAOYSA-N 3-chloro-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1NC(=O)C(C=C1Cl)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 IUJQPSWSRGBVJW-UHFFFAOYSA-N 0.000 claims description 5
• WEHVNKBYLJCMMJ-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-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=C1N(C)C(=O)C(F)(F)CN2C1CCC1 WEHVNKBYLJCMMJ-UHFFFAOYSA-N 0.000 claims description 5
• FBOOQQSTUJIFAM-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCC3)C2=N1 FBOOQQSTUJIFAM-UHFFFAOYSA-N 0.000 claims description 5
• ULDARIOAPUUKJG-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-piperidin-4-ylbenzamide Chemical compound COC1=CC(C(=O)NC2CCNCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCC1 ULDARIOAPUUKJG-UHFFFAOYSA-N 0.000 claims description 5
• PMVOUTHKCYEMPQ-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-ethylpiperidin-4-yl)-3-methoxybenzamide Chemical compound C1CN(CC)CCC1NC(=O)C(C=C1OC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCC3)C2=N1 PMVOUTHKCYEMPQ-UHFFFAOYSA-N 0.000 claims description 5
• NFUNSBDLHHIBSL-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1NC(=O)C(C=C1)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCC3)C2=N1 NFUNSBDLHHIBSL-UHFFFAOYSA-N 0.000 claims description 5
• XSZUPBHQHPFDSL-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[2-(dimethylamino)ethyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCC3)C2=N1 XSZUPBHQHPFDSL-UHFFFAOYSA-N 0.000 claims description 5
• QXWJUCOMFHDLPF-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[2-(dimethylamino)ethyl]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCC3)C2=N1 QXWJUCOMFHDLPF-UHFFFAOYSA-N 0.000 claims description 5
• PGHBBDMNKBAQNE-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCC3)C2=N1 PGHBBDMNKBAQNE-UHFFFAOYSA-N 0.000 claims description 5
• RRBKFQWILURZSY-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]benzamide Chemical compound C1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCC3)C2=N1 RRBKFQWILURZSY-UHFFFAOYSA-N 0.000 claims description 5
• IVXWOETVECBJHF-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-piperidin-4-ylbenzamide Chemical compound N1=C2N(C3CCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C=C1)=CC=C1C(=O)NC1CCNCC1 IVXWOETVECBJHF-UHFFFAOYSA-N 0.000 claims description 5
• NDUUNZYFHCECHM-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]benzamide Chemical compound N1=C2N(C3CCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC1=CC=C(C(N)=O)C=C1 NDUUNZYFHCECHM-UHFFFAOYSA-N 0.000 claims description 5
• RUOIOJYKNJAUQV-UHFFFAOYSA-N 4-[(9-cyclopentyl-5-ethyl-7,7-difluoro-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CC)C2=CN=C1NC(C(=C1)OC)=CC=C1C(=O)NC1CCN(C)CC1 RUOIOJYKNJAUQV-UHFFFAOYSA-N 0.000 claims description 5
• YQNSTWINJRVYTB-UHFFFAOYSA-N 4-[(9-cyclopentyl-5-ethyl-7,7-difluoro-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-methylbenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CC)C2=CN=C1NC1=CC=C(C(=O)NC)C=C1OC YQNSTWINJRVYTB-UHFFFAOYSA-N 0.000 claims description 5
• MCUKECQUPXGEMT-UHFFFAOYSA-N 4-[(9-cyclopentyl-5-ethyl-7,7-difluoro-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CC)C2=CN=C1NC1=CC=C(C(N)=O)C=C1OC MCUKECQUPXGEMT-UHFFFAOYSA-N 0.000 claims description 5
• KVBRBWXEQBACPD-UHFFFAOYSA-N 4-[(9-cyclopentyl-5-ethyl-7,7-difluoro-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(oxan-4-yl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CC)C2=CN=C1NC(C=C1)=CC=C1C(=O)NC1CCOCC1 KVBRBWXEQBACPD-UHFFFAOYSA-N 0.000 claims description 5
• RHZKFRVTDFPYRR-UHFFFAOYSA-N 4-[(9-cyclopentyl-5-ethyl-7,7-difluoro-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-3-methoxybenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CC)C2=CN=C1NC1=CC=C(C(=O)NCCCN(C)C)C=C1OC RHZKFRVTDFPYRR-UHFFFAOYSA-N 0.000 claims description 5
• FWGVXQRBROHEEF-UHFFFAOYSA-N 4-[(9-cyclopentyl-5-ethyl-7,7-difluoro-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-methylbenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CC)C2=CN=C1NC1=CC=C(C(=O)NC)C=C1 FWGVXQRBROHEEF-UHFFFAOYSA-N 0.000 claims description 5
• VVMNBLKDKMMETH-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(oxan-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCOCC1 VVMNBLKDKMMETH-UHFFFAOYSA-N 0.000 claims description 5
• AVIARCKQBCAZBH-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-methylbenzamide Chemical compound C1=C(F)C(C(=O)NC)=CC(OC)=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 AVIARCKQBCAZBH-UHFFFAOYSA-N 0.000 claims description 5
• ODVBAYANYQNILT-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-piperidin-4-ylbenzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCNCC1 ODVBAYANYQNILT-UHFFFAOYSA-N 0.000 claims description 5
• GQJXXADLKQPPTK-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxybenzamide Chemical compound COC1=CC(C(N)=O)=C(F)C=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 GQJXXADLKQPPTK-UHFFFAOYSA-N 0.000 claims description 5
• WHOINWVKRUBFPQ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-(trifluoromethyl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC1=CC=C(C(N)=O)C=C1C(F)(F)F WHOINWVKRUBFPQ-UHFFFAOYSA-N 0.000 claims description 5
• KSQCIWNAZLUWQK-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethoxy-n-(1-ethylpiperidin-4-yl)benzamide Chemical compound CCOC1=CC(C(=O)NC2CCN(CC)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 KSQCIWNAZLUWQK-UHFFFAOYSA-N 0.000 claims description 5
• HQBLKFSTQFDCHI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound CCOC1=CC(C(=O)NC2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 HQBLKFSTQFDCHI-UHFFFAOYSA-N 0.000 claims description 5
• RDEVSZJYXCOMKE-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethyl-n-(1-ethylpiperidin-4-yl)benzamide Chemical compound C1CN(CC)CCC1NC(=O)C(C=C1CC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 RDEVSZJYXCOMKE-UHFFFAOYSA-N 0.000 claims description 5
• XCXUJMZIPNJQGW-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethyl-n-(1-methylpiperidin-4-yl)benzamide Chemical compound CCC1=CC(C(=O)NC2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 XCXUJMZIPNJQGW-UHFFFAOYSA-N 0.000 claims description 5
• RPFAZEOEDWRAOL-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethyl-n-methylbenzamide Chemical compound CCC1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 RPFAZEOEDWRAOL-UHFFFAOYSA-N 0.000 claims description 5
• OQFJJHMUDNKYGT-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(1-methylazetidin-3-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CN(C)C2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 OQFJJHMUDNKYGT-UHFFFAOYSA-N 0.000 claims description 5
• DJNZZLZKAXGMMC-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-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=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 DJNZZLZKAXGMMC-UHFFFAOYSA-N 0.000 claims description 5
• SSGFRFHOPDHRLJ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(1-phenylethyl)benzamide Chemical compound COC1=CC(C(=O)NC(C)C=2C=CC=CC=2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 SSGFRFHOPDHRLJ-UHFFFAOYSA-N 0.000 claims description 5
• PPSWWWMGJLWMQP-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(2,2,6,6-tetramethylpiperidin-4-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CC(C)(C)NC(C)(C)C2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 PPSWWWMGJLWMQP-UHFFFAOYSA-N 0.000 claims description 5
• REFUJAXKLCTSJG-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(2-piperidin-1-ylethyl)benzamide Chemical compound COC1=CC(C(=O)NCCN2CCCCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 REFUJAXKLCTSJG-UHFFFAOYSA-N 0.000 claims description 5
• BZMPOAXTVCJMPA-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(3-methoxypiperidin-4-yl)benzamide Chemical compound COC1CNCCC1NC(=O)C(C=C1OC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 BZMPOAXTVCJMPA-UHFFFAOYSA-N 0.000 claims description 5
• QWDOEQFTIIFGRO-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-[1-(3-methylsulfonylpropyl)piperidin-4-yl]benzamide Chemical compound COC1=CC(C(=O)NC2CCN(CCCS(C)(=O)=O)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 QWDOEQFTIIFGRO-UHFFFAOYSA-N 0.000 claims description 5
• MUQIJSDCRJKAOW-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-[2-(1-methylpyrrolidin-2-yl)ethyl]benzamide Chemical compound COC1=CC(C(=O)NCCC2N(CCC2)C)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 MUQIJSDCRJKAOW-UHFFFAOYSA-N 0.000 claims description 5
• OFLJIARPXSOEFR-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-[3-(2-oxopyrrolidin-1-yl)propyl]benzamide Chemical compound COC1=CC(C(=O)NCCCN2C(CCC2)=O)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 OFLJIARPXSOEFR-UHFFFAOYSA-N 0.000 claims description 5
• VJZCQHMPYHGUHW-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-[[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound COC1=CC(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 VJZCQHMPYHGUHW-UHFFFAOYSA-N 0.000 claims description 5
• VHFRRQFMCDERFH-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-phenylbenzamide Chemical compound COC1=CC(C(=O)NC=2C=CC=CC=2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 VHFRRQFMCDERFH-UHFFFAOYSA-N 0.000 claims description 5
• SHBWZOHGEVPNGK-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-piperidin-4-ylbenzamide Chemical compound COC1=CC(C(=O)NC2CCNCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 SHBWZOHGEVPNGK-UHFFFAOYSA-N 0.000 claims description 5
• GAQLGMAZHNCUEH-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methyl-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1NC(=O)C(C=C1C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 GAQLGMAZHNCUEH-UHFFFAOYSA-N 0.000 claims description 5
• NKWDWRQAIWLVQX-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n,3-dimethylbenzamide Chemical compound CC1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 NKWDWRQAIWLVQX-UHFFFAOYSA-N 0.000 claims description 5
• GGTRXLGNWTVQMQ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-cyclopentylpiperidin-4-yl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CCN(CC2)C2CCCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 GGTRXLGNWTVQMQ-UHFFFAOYSA-N 0.000 claims description 5
• AOGYILPAZJWWEO-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-cyclopropylpiperidin-4-yl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CCN(CC2)C2CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 AOGYILPAZJWWEO-UHFFFAOYSA-N 0.000 claims description 5
• OWBPCPUOKHELBW-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-ethylpiperidin-4-yl)-3-(trifluoromethyl)benzamide Chemical compound C1CN(CC)CCC1NC(=O)C(C=C1C(F)(F)F)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 OWBPCPUOKHELBW-UHFFFAOYSA-N 0.000 claims description 5
• QFLZTKMRVNTGQH-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-ethylpiperidin-4-yl)-3-methoxybenzamide Chemical compound C1CN(CC)CCC1NC(=O)C(C=C1OC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 QFLZTKMRVNTGQH-UHFFFAOYSA-N 0.000 claims description 5
• IDFLZBNSRJTOPH-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-ethylpiperidin-4-yl)-3-methylbenzamide Chemical compound C1CN(CC)CCC1NC(=O)C(C=C1C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 IDFLZBNSRJTOPH-UHFFFAOYSA-N 0.000 claims description 5
• FKHRYUDFWFPNRM-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-methylpiperidin-4-yl)-3-(trifluoromethoxy)benzamide Chemical compound C1CN(C)CCC1NC(=O)C(C=C1OC(F)(F)F)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 FKHRYUDFWFPNRM-UHFFFAOYSA-N 0.000 claims description 5
• AGZWLPUVHFMVLT-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-methylpiperidin-4-yl)-3-propan-2-yloxybenzamide Chemical compound CC(C)OC1=CC(C(=O)NC2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 AGZWLPUVHFMVLT-UHFFFAOYSA-N 0.000 claims description 5
• HTIHGFRFJHRDCL-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(2-ethoxyethyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCOCC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 HTIHGFRFJHRDCL-UHFFFAOYSA-N 0.000 claims description 5
• GQVQPKONQLVQPF-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(3-imidazol-1-ylpropyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN2C=NC=C2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 GQVQPKONQLVQPF-UHFFFAOYSA-N 0.000 claims description 5
• NRXNHAUTZNKJGS-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(4-hydroxybutyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCCO)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 NRXNHAUTZNKJGS-UHFFFAOYSA-N 0.000 claims description 5
• JKYXXSSNVGHEJH-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(oxan-4-yl)-3-(trifluoromethyl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C(=C1)C(F)(F)F)=CC=C1C(=O)NC1CCOCC1 JKYXXSSNVGHEJH-UHFFFAOYSA-N 0.000 claims description 5
• MHVTYJIOWYEMEU-IEBWSBKVSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[(3r,4r)-4-hydroxypyrrolidin-3-yl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)N[C@H]2[C@@H](CNC2)O)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 MHVTYJIOWYEMEU-IEBWSBKVSA-N 0.000 claims description 5
• NCMKGIMDIXOHPG-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[1-(2-fluoroethyl)piperidin-4-yl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CCN(CCF)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 NCMKGIMDIXOHPG-UHFFFAOYSA-N 0.000 claims description 5
• WZCBUMSLQRGNHI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[2-(dimethylamino)ethyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(C(=O)NCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 WZCBUMSLQRGNHI-UHFFFAOYSA-N 0.000 claims description 5
• JJRBPPFLTOPESW-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(4-hydroxypiperidin-1-yl)propyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN2CCC(O)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 JJRBPPFLTOPESW-UHFFFAOYSA-N 0.000 claims description 5
• LRMZEFKMUKWUIH-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)-2,2-dimethylpropyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCC(C)(C)CN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 LRMZEFKMUKWUIH-UHFFFAOYSA-N 0.000 claims description 5
• MMZDWEJLOAGTJA-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-2-fluoro-5-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN(C)C)=C(F)C=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 MMZDWEJLOAGTJA-UHFFFAOYSA-N 0.000 claims description 5
• LYZWISCMBGUXGE-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 LYZWISCMBGUXGE-UHFFFAOYSA-N 0.000 claims description 5
• MHKLTXHSWNNYJZ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN2CCN(CCO)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 MHKLTXHSWNNYJZ-UHFFFAOYSA-N 0.000 claims description 5
• RGMABEIKUYJTJO-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-methyl-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 RGMABEIKUYJTJO-UHFFFAOYSA-N 0.000 claims description 5
• BTDBBVCKFAZCGE-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-piperidin-4-yl-3-(trifluoromethyl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C(=C1)C(F)(F)F)=CC=C1C(=O)NC1CCNCC1 BTDBBVCKFAZCGE-UHFFFAOYSA-N 0.000 claims description 5
• TXZJHBVAUZZCIV-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1NC(=O)C(C=C1)=CC=C1NC1=NC=C(NC(=O)C(F)(F)CN2C3CCCC3)C2=N1 TXZJHBVAUZZCIV-UHFFFAOYSA-N 0.000 claims description 5
• JIJBYSBXCDZJOF-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(oxan-4-yl)benzamide Chemical compound C12=NC(NC=3C=CC(=CC=3)C(=O)NC3CCOCC3)=NC=C2NC(=O)C(F)(F)CN1C1CCCC1 JIJBYSBXCDZJOF-UHFFFAOYSA-N 0.000 claims description 5
• WDWPFFDRGWGKTA-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(NC(=O)C(F)(F)CN2C3CCCC3)C2=N1 WDWPFFDRGWGKTA-UHFFFAOYSA-N 0.000 claims description 5
• SNFFXIKTYVRJJT-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1NC1=NC=C(NC(=O)C(F)(F)CN2C3CCCC3)C2=N1 SNFFXIKTYVRJJT-UHFFFAOYSA-N 0.000 claims description 5
• GPLDKLIAVDXEJD-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5-propyl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CCC)C2=CN=C1NC(C(=C1)OC)=CC=C1C(=O)NC1CCN(C)CC1 GPLDKLIAVDXEJD-UHFFFAOYSA-N 0.000 claims description 5
• YLSMPWWVVOLKEX-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5-propyl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-methylbenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CCC)C2=CN=C1NC1=CC=C(C(=O)NC)C=C1OC YLSMPWWVVOLKEX-UHFFFAOYSA-N 0.000 claims description 5
• TTXPBUDDEYMKHD-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5-propyl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CCC)C2=CN=C1NC1=CC=C(C(N)=O)C=C1OC TTXPBUDDEYMKHD-UHFFFAOYSA-N 0.000 claims description 5
• VMTJUFZAQPHXEE-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5-propyl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-3-methoxybenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CCC)C2=CN=C1NC1=CC=C(C(=O)NCCCN(C)C)C=C1OC VMTJUFZAQPHXEE-UHFFFAOYSA-N 0.000 claims description 5
• FJOUCLBBJFWXSP-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5-propyl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-methylbenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CCC)C2=CN=C1NC1=CC=C(C(=O)NC)C=C1 FJOUCLBBJFWXSP-UHFFFAOYSA-N 0.000 claims description 5
• RJSCKYMFABFIIC-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5-propyl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CCC)C2=CN=C1NC1=CC=C(C(N)=O)C=C1 RJSCKYMFABFIIC-UHFFFAOYSA-N 0.000 claims description 5
• JGXHMSFNMFZFLG-UHFFFAOYSA-N 4-[[9-cyclopentyl-7,7-difluoro-6-oxo-5-(2,2,2-trifluoroethyl)-8h-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=C1N(CC(F)(F)F)C(=O)C(F)(F)CN2C1CCCC1 JGXHMSFNMFZFLG-UHFFFAOYSA-N 0.000 claims description 5
• HWDBPLXCHQEMRD-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-[3-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]propyl]carbamate Chemical compound COC1=CC(C(=O)NCCCNC(=O)OCC2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 HWDBPLXCHQEMRD-UHFFFAOYSA-N 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• ITEZHQFBMXTVNV-UHFFFAOYSA-N methyl 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxybenzoate Chemical compound C1=C(F)C(C(=O)OC)=CC(OC)=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 ITEZHQFBMXTVNV-UHFFFAOYSA-N 0.000 claims description 5
• DVWLYDMAMWHJQE-UHFFFAOYSA-N n-(1-acetylpiperidin-4-yl)-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CCN(CC2)C(C)=O)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 DVWLYDMAMWHJQE-UHFFFAOYSA-N 0.000 claims description 5
• URLSPPAAXZIPQQ-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 URLSPPAAXZIPQQ-UHFFFAOYSA-N 0.000 claims description 5
• ZYZNGWOTBSRQRZ-UHFFFAOYSA-N n-[3-(cyclohexylamino)propyl]-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCNC2CCCCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 ZYZNGWOTBSRQRZ-UHFFFAOYSA-N 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• SRRVBDKOWVGKSP-LJQANCHMSA-N tert-butyl (3r)-3-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]pyrrolidine-1-carboxylate Chemical compound COC1=CC(C(=O)N[C@H]2CN(CC2)C(=O)OC(C)(C)C)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 SRRVBDKOWVGKSP-LJQANCHMSA-N 0.000 claims description 5
• VGFCEGXMJRFFPC-UHFFFAOYSA-N tert-butyl 3-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]azetidine-1-carboxylate Chemical compound COC1=CC(C(=O)NC2CN(C2)C(=O)OC(C)(C)C)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 VGFCEGXMJRFFPC-UHFFFAOYSA-N 0.000 claims description 5
• SDHDTPJXPNWEJQ-UHFFFAOYSA-N tert-butyl 3-[[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]methyl]azetidine-1-carboxylate Chemical compound COC1=CC(C(=O)NCC2CN(C2)C(=O)OC(C)(C)C)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 SDHDTPJXPNWEJQ-UHFFFAOYSA-N 0.000 claims description 5
• XJSVIHIQQOGDKK-UHFFFAOYSA-N 2-[4-(4-aminopiperidine-1-carbonyl)anilino]-9-cyclobutyl-7,7-difluoro-5-methyl-8h-pyrimido[4,5-b][1,4]diazepin-6-one Chemical compound N1=C2N(C3CCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C=C1)=CC=C1C(=O)N1CCC(N)CC1 XJSVIHIQQOGDKK-UHFFFAOYSA-N 0.000 claims description 4
• SOFNFHDUACNLQO-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCC3)C2=N1 SOFNFHDUACNLQO-UHFFFAOYSA-N 0.000 claims description 4
• QHZJGPRXYWGMML-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCC3)C2=N1 QHZJGPRXYWGMML-UHFFFAOYSA-N 0.000 claims description 4
• VGBLKNGMQCWXDU-UHFFFAOYSA-N 4-[(9-cyclopentyl-5-ethyl-7,7-difluoro-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(oxan-4-yl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CC)C2=CN=C1NC(C(=C1)OC)=CC=C1C(=O)NC1CCOCC1 VGBLKNGMQCWXDU-UHFFFAOYSA-N 0.000 claims description 4
• VZUVZFKLXAGIGF-UHFFFAOYSA-N 4-[(9-cyclopentyl-5-ethyl-7,7-difluoro-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CC)C2=CN=C1NC(C=C1)=CC=C1C(=O)NC1CCN(C)CC1 VZUVZFKLXAGIGF-UHFFFAOYSA-N 0.000 claims description 4
• QGVDUOVUPWJDJK-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethoxy-n-(oxan-4-yl)benzamide Chemical compound CCOC1=CC(C(=O)NC2CCOCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 QGVDUOVUPWJDJK-UHFFFAOYSA-N 0.000 claims description 4
• ASJBKOWVWPCRCF-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethyl-n-(oxan-4-yl)benzamide Chemical compound CCC1=CC(C(=O)NC2CCOCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 ASJBKOWVWPCRCF-UHFFFAOYSA-N 0.000 claims description 4
• JEXBNPMDDPNUAM-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethyl-n-piperidin-4-ylbenzamide Chemical compound CCC1=CC(C(=O)NC2CCNCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 JEXBNPMDDPNUAM-UHFFFAOYSA-N 0.000 claims description 4
• IHCXVPRBNKTTST-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(pyridin-2-ylmethyl)benzamide Chemical compound COC1=CC(C(=O)NCC=2N=CC=CC=2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 IHCXVPRBNKTTST-UHFFFAOYSA-N 0.000 claims description 4
• QVIMVYQXQPICTI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-[3-(2-methylpiperidin-1-yl)propyl]benzamide Chemical compound COC1=CC(C(=O)NCCCN2C(CCCC2)C)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 QVIMVYQXQPICTI-UHFFFAOYSA-N 0.000 claims description 4
• VNLUXOVXQNANKP-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-piperidin-1-ylbenzamide Chemical compound COC1=CC(C(=O)NN2CCCCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 VNLUXOVXQNANKP-UHFFFAOYSA-N 0.000 claims description 4
• PMRVLWKZCJBMKA-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methyl-n-(oxan-4-yl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C(=C1)C)=CC=C1C(=O)NC1CCOCC1 PMRVLWKZCJBMKA-UHFFFAOYSA-N 0.000 claims description 4
• OAXMQNLWOHOQLY-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methyl-n-piperidin-4-ylbenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C(=C1)C)=CC=C1C(=O)NC1CCNCC1 OAXMQNLWOHOQLY-UHFFFAOYSA-N 0.000 claims description 4
• BAVKHKJJAGWXBX-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1NC(=O)C(C=C1)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 BAVKHKJJAGWXBX-UHFFFAOYSA-N 0.000 claims description 4
• JMTVQKMGWVDRNW-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(2-hydroxyethyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCO)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 JMTVQKMGWVDRNW-UHFFFAOYSA-N 0.000 claims description 4
• CDDAHMMJPVSGEG-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(3-hydroxypropyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCO)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 CDDAHMMJPVSGEG-UHFFFAOYSA-N 0.000 claims description 4
• GQLVXOANBOXIQA-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[2-(dimethylamino)ethyl]-3-ethylbenzamide Chemical compound CCC1=CC(C(=O)NCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 GQLVXOANBOXIQA-UHFFFAOYSA-N 0.000 claims description 4
• LCBXHJUUUSMVQJ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[2-(dimethylamino)ethyl]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 LCBXHJUUUSMVQJ-UHFFFAOYSA-N 0.000 claims description 4
• QXMRUZQGRPKZTN-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-3-ethylbenzamide Chemical compound CCC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 QXMRUZQGRPKZTN-UHFFFAOYSA-N 0.000 claims description 4
• BUMIHSDPFQCQPU-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 BUMIHSDPFQCQPU-UHFFFAOYSA-N 0.000 claims description 4
• WSGGDYOQRXZPHK-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 WSGGDYOQRXZPHK-UHFFFAOYSA-N 0.000 claims description 4
• WVIKSKULBURUSG-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5-propyl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(oxan-4-yl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CCC)C2=CN=C1NC(C(=C1)OC)=CC=C1C(=O)NC1CCOCC1 WVIKSKULBURUSG-UHFFFAOYSA-N 0.000 claims description 4
• WOXAQOYAOVFVAO-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5-propyl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CCC)C2=CN=C1NC(C=C1)=CC=C1C(=O)NC1CCN(C)CC1 WOXAQOYAOVFVAO-UHFFFAOYSA-N 0.000 claims description 4
• YVEXJBKEHVYNBU-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5-propyl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(oxan-4-yl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CCC)C2=CN=C1NC(C=C1)=CC=C1C(=O)NC1CCOCC1 YVEXJBKEHVYNBU-UHFFFAOYSA-N 0.000 claims description 4
• AOPLBXJWRHSSBY-UHFFFAOYSA-N 4-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]-3-methoxypiperidine-1-carboxylic acid Chemical compound COC1CN(C(O)=O)CCC1NC(=O)C(C=C1OC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 AOPLBXJWRHSSBY-UHFFFAOYSA-N 0.000 claims description 4
• DNKMRTCAQIWEMH-UAPYVXQJSA-N COc1cc(ccc1Nc1ncc2N(C)C(=O)C(F)(F)CN(C3CCCC3)c2n1)C(=O)N[C@H]1CC[C@H](O)CC1 Chemical compound COc1cc(ccc1Nc1ncc2N(C)C(=O)C(F)(F)CN(C3CCCC3)c2n1)C(=O)N[C@H]1CC[C@H](O)CC1 DNKMRTCAQIWEMH-UAPYVXQJSA-N 0.000 claims description 4
• KJJGHYCAQGXSND-UHFFFAOYSA-N benzyl 3-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]-4-methoxypiperidine-1-carboxylate Chemical compound COC1CCN(C(=O)OCC=2C=CC=CC=2)CC1NC(=O)C(C=C1OC)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 KJJGHYCAQGXSND-UHFFFAOYSA-N 0.000 claims description 4
• PHYNULCBHHKXNF-UHFFFAOYSA-N benzyl 4-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]-3-hydroxypiperidine-1-carboxylate Chemical compound COC1=CC(C(=O)NC2C(CN(CC2)C(=O)OCC=2C=CC=CC=2)O)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 PHYNULCBHHKXNF-UHFFFAOYSA-N 0.000 claims description 4
• XCAYLNUEFMJDPI-UHFFFAOYSA-N benzyl 4-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]-3-methoxypiperidine-1-carboxylate Chemical compound COC1CN(C(=O)OCC=2C=CC=CC=2)CCC1NC(=O)C(C=C1OC)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 XCAYLNUEFMJDPI-UHFFFAOYSA-N 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 201000011510 cancer Diseases 0.000 claims description 4
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• UKNAHZQUOVKSEY-UHFFFAOYSA-N n-(2-aminoethyl)-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCN)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 UKNAHZQUOVKSEY-UHFFFAOYSA-N 0.000 claims description 4
• LNRXIIDKFKDPDK-UHFFFAOYSA-N n-(3-aminopropyl)-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 LNRXIIDKFKDPDK-UHFFFAOYSA-N 0.000 claims description 4
• UTKYNIJOYJVVCV-UHFFFAOYSA-N tert-butyl 4-[3-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]-2-hydroxypropyl]piperazine-1-carboxylate Chemical compound COC1=CC(C(=O)NCC(O)CN2CCN(CC2)C(=O)OC(C)(C)C)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 UTKYNIJOYJVVCV-UHFFFAOYSA-N 0.000 claims description 4
• ZXJQPLDVYSFMMO-UHFFFAOYSA-N tert-butyl 4-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxybenzoyl]amino]piperidine-1-carboxylate Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C(=O)OC(C)(C)C)CC1 ZXJQPLDVYSFMMO-UHFFFAOYSA-N 0.000 claims description 4
• JICWZVNOOVUFPQ-UHFFFAOYSA-N tert-butyl 4-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-(trifluoromethyl)benzoyl]amino]piperidine-1-carboxylate Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C(=C1)C(F)(F)F)=CC=C1C(=O)NC1CCN(C(=O)OC(C)(C)C)CC1 JICWZVNOOVUFPQ-UHFFFAOYSA-N 0.000 claims description 4
• XKMOEYVYJAKVCC-UHFFFAOYSA-N tert-butyl 4-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethylbenzoyl]amino]piperidine-1-carboxylate Chemical compound CCC1=CC(C(=O)NC2CCN(CC2)C(=O)OC(C)(C)C)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 XKMOEYVYJAKVCC-UHFFFAOYSA-N 0.000 claims description 4
• RLJXSWWPBDQRQC-UHFFFAOYSA-N tert-butyl 4-[[4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methylbenzoyl]amino]piperidine-1-carboxylate Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C(=C1)C)=CC=C1C(=O)NC1CCN(C(=O)OC(C)(C)C)CC1 RLJXSWWPBDQRQC-UHFFFAOYSA-N 0.000 claims description 4
• YRJDTCLZCJQGRW-UHFFFAOYSA-N 4-[(9-cyclobutyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(oxan-4-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CCOCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCC1 YRJDTCLZCJQGRW-UHFFFAOYSA-N 0.000 claims description 3
• RYLGNUNRJIFJKD-UHFFFAOYSA-N 4-[(9-cyclopentyl-5-ethyl-7,7-difluoro-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(CC)C2=CN=C1NC1=CC=C(C(N)=O)C=C1 RYLGNUNRJIFJKD-UHFFFAOYSA-N 0.000 claims description 3
• GCUSJAKGEHXMMP-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n,n-dimethylbenzamide Chemical compound COC1=CC(C(=O)N(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 GCUSJAKGEHXMMP-UHFFFAOYSA-N 0.000 claims description 3
• QAEBWIGYZGSZLV-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CC(C)(C)N(C)C(C)(C)C2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 QAEBWIGYZGSZLV-UHFFFAOYSA-N 0.000 claims description 3
• HNYYPGGUOWXBRZ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(2,2,2-trifluoroethyl)benzamide Chemical compound COC1=CC(C(=O)NCC(F)(F)F)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 HNYYPGGUOWXBRZ-UHFFFAOYSA-N 0.000 claims description 3
• GPCOICHTEDRQPJ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(2-morpholin-4-ylethyl)benzamide Chemical compound COC1=CC(C(=O)NCCN2CCOCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 GPCOICHTEDRQPJ-UHFFFAOYSA-N 0.000 claims description 3
• MUYSTFCIYMONGL-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(2-piperazin-1-ylethyl)benzamide Chemical compound COC1=CC(C(=O)NCCN2CCNCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 MUYSTFCIYMONGL-UHFFFAOYSA-N 0.000 claims description 3
• VNJSZNVUAZYRHM-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(2-pyridin-2-ylethyl)benzamide Chemical compound COC1=CC(C(=O)NCCC=2N=CC=CC=2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 VNJSZNVUAZYRHM-UHFFFAOYSA-N 0.000 claims description 3
• HNGGTOIHLQKNLD-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(3-methoxypropyl)benzamide Chemical compound COC1=CC(C(=O)NCCCOC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 HNGGTOIHLQKNLD-UHFFFAOYSA-N 0.000 claims description 3
• IYEVKFRISSVCQZ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(3-morpholin-4-ylpropyl)benzamide Chemical compound COC1=CC(C(=O)NCCCN2CCOCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 IYEVKFRISSVCQZ-UHFFFAOYSA-N 0.000 claims description 3
• CCTSONUJHJYHOL-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(3-piperazin-1-ylpropyl)benzamide Chemical compound COC1=CC(C(=O)NCCCN2CCNCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 CCTSONUJHJYHOL-UHFFFAOYSA-N 0.000 claims description 3
• BVGRFOSUDOWGPJ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound COC1=CC(C(=O)NCCCN2CCCCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 BVGRFOSUDOWGPJ-UHFFFAOYSA-N 0.000 claims description 3
• LMVXOIOZFWFVQH-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(3-pyrrolidin-1-ylpropyl)benzamide Chemical compound COC1=CC(C(=O)NCCCN2CCCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 LMVXOIOZFWFVQH-UHFFFAOYSA-N 0.000 claims description 3
• INRRBJHFKZXWEP-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CC3CCC(N3C)C2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 INRRBJHFKZXWEP-UHFFFAOYSA-N 0.000 claims description 3
• NWBQJXADKGIORI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(thiophen-3-ylmethyl)benzamide Chemical compound COC1=CC(C(=O)NCC2=CSC=C2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 NWBQJXADKGIORI-UHFFFAOYSA-N 0.000 claims description 3
• HNWQTQZVTFKAGZ-MRXNPFEDSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-[(4r)-2-oxopiperidin-4-yl]benzamide Chemical compound COC1=CC(C(=O)N[C@H]2CC(=O)NCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 HNWQTQZVTFKAGZ-MRXNPFEDSA-N 0.000 claims description 3
• HLCDTULFFZETLA-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]benzamide Chemical compound COC1=CC(C(=O)NC2CCN(CC(F)(F)F)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 HLCDTULFFZETLA-UHFFFAOYSA-N 0.000 claims description 3
• LVBNGIACKIUHCF-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-[2-(4-methylpiperazin-1-yl)ethyl]benzamide Chemical compound COC1=CC(C(=O)NCCN2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 LVBNGIACKIUHCF-UHFFFAOYSA-N 0.000 claims description 3
• YSHXGRIXSBLABD-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-[3-(4-methylpiperazin-1-yl)propyl]benzamide Chemical compound COC1=CC(C(=O)NCCCN2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 YSHXGRIXSBLABD-UHFFFAOYSA-N 0.000 claims description 3
• GAOBDFYSUUSEPG-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-[3-(propan-2-ylamino)propyl]benzamide Chemical compound COC1=CC(C(=O)NCCCNC(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 GAOBDFYSUUSEPG-UHFFFAOYSA-N 0.000 claims description 3
• BTQNGTAMCLWLOP-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 BTQNGTAMCLWLOP-UHFFFAOYSA-N 0.000 claims description 3
• KZSITJNQLRUINH-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-propan-2-ylbenzamide Chemical compound COC1=CC(C(=O)NC(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 KZSITJNQLRUINH-UHFFFAOYSA-N 0.000 claims description 3
• AVKAQJDXBSJSPO-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-pyridin-3-ylbenzamide Chemical compound COC1=CC(C(=O)NC=2C=NC=CC=2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 AVKAQJDXBSJSPO-UHFFFAOYSA-N 0.000 claims description 3
• ASFPJTHORZNERZ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-pyridin-4-ylbenzamide Chemical compound COC1=CC(C(=O)NC=2C=CN=CC=2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 ASFPJTHORZNERZ-UHFFFAOYSA-N 0.000 claims description 3
• VLZNQQJFEDMMIZ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 VLZNQQJFEDMMIZ-UHFFFAOYSA-N 0.000 claims description 3
• XPKIADKBUUPSBL-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(2-hydroxy-3-piperazin-1-ylpropyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCC(O)CN2CCNCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 XPKIADKBUUPSBL-UHFFFAOYSA-N 0.000 claims description 3
• CRQJRUCZEVKRND-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(furan-3-ylmethyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCC2=COC=C2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 CRQJRUCZEVKRND-UHFFFAOYSA-N 0.000 claims description 3
• KIXZXNODEAFUAR-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[(3,5-dichlorophenyl)methyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCC=2C=C(Cl)C=C(Cl)C=2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 KIXZXNODEAFUAR-UHFFFAOYSA-N 0.000 claims description 3
• ZYAZPEKBRUKQJS-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[2-(1h-indol-3-yl)ethyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCC=2C3=CC=CC=C3NC=2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 ZYAZPEKBRUKQJS-UHFFFAOYSA-N 0.000 claims description 3
• NUUFTAWVCPDSTE-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[2-(dimethylamino)ethyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 NUUFTAWVCPDSTE-UHFFFAOYSA-N 0.000 claims description 3
• OZTBNNQBOHWSGL-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-cyclopropyl-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 OZTBNNQBOHWSGL-UHFFFAOYSA-N 0.000 claims description 3
• VBFQMIXSLOAOFT-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-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=C1NC(=O)C(F)(F)CN2C1CCCC1 VBFQMIXSLOAOFT-UHFFFAOYSA-N 0.000 claims description 3
• WEFHVUWCANKDBA-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(oxan-4-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CCOCC2)=CC=C1NC(N=C12)=NC=C1NC(=O)C(F)(F)CN2C1CCCC1 WEFHVUWCANKDBA-UHFFFAOYSA-N 0.000 claims description 3
• FVTQIVPBYWNZJV-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NC=C(NC(=O)C(F)(F)CN2C3CCCC3)C2=N1 FVTQIVPBYWNZJV-UHFFFAOYSA-N 0.000 claims description 3
• OLCDDJZSGLELBF-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC=C1NC1=NC=C(NC(=O)C(F)(F)CN2C3CCCC3)C2=N1 OLCDDJZSGLELBF-UHFFFAOYSA-N 0.000 claims description 3
• GDPYAUCFLCWOIV-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1NC1=NC=C(NC(=O)C(F)(F)CN2C3CCCC3)C2=N1 GDPYAUCFLCWOIV-UHFFFAOYSA-N 0.000 claims description 3
• HJGMRAKQWLKWMH-UHFFFAOYSA-N 8-methyl-8-azabicyclo[3.2.1]octan-3-amine Chemical group C1C(N)CC2CCC1N2C HJGMRAKQWLKWMH-UHFFFAOYSA-N 0.000 claims description 3
• WSPVFFIWYNLVAR-UHFFFAOYSA-N 9-cyclopentyl-7,7-difluoro-2-[2-methoxy-4-(4-methylpiperazine-1-carbonyl)anilino]-5-methyl-8h-pyrimido[4,5-b][1,4]diazepin-6-one Chemical compound COC1=CC(C(=O)N2CCN(C)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 WSPVFFIWYNLVAR-UHFFFAOYSA-N 0.000 claims description 3
• FJUIIVZFSXTVTL-UHFFFAOYSA-N 9-cyclopentyl-7,7-difluoro-2-[2-methoxy-4-(morpholine-4-carbonyl)anilino]-5-methyl-8h-pyrimido[4,5-b][1,4]diazepin-6-one Chemical compound COC1=CC(C(=O)N2CCOCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 FJUIIVZFSXTVTL-UHFFFAOYSA-N 0.000 claims description 3
• YGIQYQOTXRBFNT-UHFFFAOYSA-N 9-cyclopentyl-7,7-difluoro-2-[2-methoxy-4-(piperidine-1-carbonyl)anilino]-5-methyl-8h-pyrimido[4,5-b][1,4]diazepin-6-one Chemical compound COC1=CC(C(=O)N2CCCCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 YGIQYQOTXRBFNT-UHFFFAOYSA-N 0.000 claims description 3
• BXQWIISLBIAIBL-UHFFFAOYSA-N COC1=CC(C(=O)NC2CCOCC2)=CC=C1NC(N=C12)NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 Chemical compound COC1=CC(C(=O)NC2CCOCC2)=CC=C1NC(N=C12)NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 BXQWIISLBIAIBL-UHFFFAOYSA-N 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• GQQIMHYTWZYXRD-UHFFFAOYSA-N n-(2-anilinoethyl)-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCNC=2C=CC=CC=2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 GQQIMHYTWZYXRD-UHFFFAOYSA-N 0.000 claims description 3
• YORMABKAWXREKJ-MSOLQXFVSA-N n-[(1s,2r)-2-carbamoylcyclopentyl]-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)N[C@@H]2[C@@H](CCC2)C(N)=O)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 YORMABKAWXREKJ-MSOLQXFVSA-N 0.000 claims description 3
• PMSBBZYMFIXRRY-HSZRJFAPSA-N n-[(3r)-1-benzylpyrrolidin-3-yl]-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)N[C@H]2CN(CC=3C=CC=CC=3)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 PMSBBZYMFIXRRY-HSZRJFAPSA-N 0.000 claims description 3
• PMSBBZYMFIXRRY-QHCPKHFHSA-N n-[(3s)-1-benzylpyrrolidin-3-yl]-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)N[C@@H]2CN(CC=3C=CC=CC=3)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 PMSBBZYMFIXRRY-QHCPKHFHSA-N 0.000 claims description 3
• LTXYXSPAWRYBHE-UHFFFAOYSA-N n-[1-(2-amino-2-methylpropanoyl)piperidin-4-yl]-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CCN(CC2)C(=O)C(C)(C)N)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 LTXYXSPAWRYBHE-UHFFFAOYSA-N 0.000 claims description 3
• DFZLKACBKLZYPV-UHFFFAOYSA-N n-[2-(1,3-benzodioxol-5-yl)ethyl]-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCC=2C=C3OCOC3=CC=2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 DFZLKACBKLZYPV-UHFFFAOYSA-N 0.000 claims description 3
• JRQQKDFKPKOJMQ-UHFFFAOYSA-N n-benzyl-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCC=2C=CC=CC=2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 JRQQKDFKPKOJMQ-UHFFFAOYSA-N 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• IVLIBVDZIYFXBZ-UHFFFAOYSA-N 1-(cyclopropylmethyl)piperazine Chemical group C1CNCCN1CC1CC1 IVLIBVDZIYFXBZ-UHFFFAOYSA-N 0.000 claims description 2
• CLTNVISMFUXTBB-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(2-methoxyethyl)benzamide Chemical compound COC1=CC(C(=O)NCCOC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 CLTNVISMFUXTBB-UHFFFAOYSA-N 0.000 claims description 2
• SGURCXCFSYTOBV-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[2-(dimethylamino)ethyl]-3-ethoxybenzamide Chemical compound CCOC1=CC(C(=O)NCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 SGURCXCFSYTOBV-UHFFFAOYSA-N 0.000 claims description 2
• PLUVZWFMFVKRHA-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-3-ethoxybenzamide Chemical compound CCOC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 PLUVZWFMFVKRHA-UHFFFAOYSA-N 0.000 claims description 2
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000001188 haloalkyl group Chemical group 0.000 claims description 2
• QKTDZSUFSULVBU-UHFFFAOYSA-N n-(cyclohexylmethyl)-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCC2CCCCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 QKTDZSUFSULVBU-UHFFFAOYSA-N 0.000 claims description 2
• CYPURHFPZAURSP-UHFFFAOYSA-N n-cyclohexyl-4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CCCCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 CYPURHFPZAURSP-UHFFFAOYSA-N 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• 230000001225 therapeutic effect Effects 0.000 claims description 2
• 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 11
• PKZWKPAABMRORY-UHFFFAOYSA-N 4-[(7,7-dichloro-9-cyclopentyl-5-methyl-6-oxo-8h-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=C1N(C)C(=O)C(Cl)(Cl)CN2C1CCCC1 PKZWKPAABMRORY-UHFFFAOYSA-N 0.000 claims 1
• CUGXNMGSBCPUMK-UHFFFAOYSA-N 4-[(7,7-difluoro-5-methyl-6-oxo-9-propan-2-yl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C=1C=C(NC=2N=C3N(C(C)C)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 CUGXNMGSBCPUMK-UHFFFAOYSA-N 0.000 claims 1
• ARNDJWGIBIQISZ-UHFFFAOYSA-N 4-[(7,7-difluoro-5-methyl-6-oxo-9-propan-2-yl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(oxan-4-yl)benzamide Chemical compound C=1C=C(NC=2N=C3N(C(C)C)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCOCC1 ARNDJWGIBIQISZ-UHFFFAOYSA-N 0.000 claims 1
• HUPWVZNKIAVJMW-UHFFFAOYSA-N 4-[(7,7-difluoro-5-methyl-6-oxo-9-propan-2-yl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C(C)C)C2=N1 HUPWVZNKIAVJMW-UHFFFAOYSA-N 0.000 claims 1
• JWCXYAVDRNDFPO-UHFFFAOYSA-N 4-[(7,7-difluoro-5-methyl-6-oxo-9-propan-2-yl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C(C)C)C2=N1 JWCXYAVDRNDFPO-UHFFFAOYSA-N 0.000 claims 1
• QUXFDKQTHXTQKE-UHFFFAOYSA-N 4-[(7,7-difluoro-5-methyl-6-oxo-9-propan-2-yl-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C(C)C)C2=N1 QUXFDKQTHXTQKE-UHFFFAOYSA-N 0.000 claims 1
• FGRHPASIBCUARJ-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-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=C1N(C)C(=O)C(F)(F)CN2C1CCCCC1 FGRHPASIBCUARJ-UHFFFAOYSA-N 0.000 claims 1
• FBTDYGMLBQDGIM-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(1-methylsulfonylpiperidin-4-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CCN(CC2)S(C)(=O)=O)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCCC1 FBTDYGMLBQDGIM-UHFFFAOYSA-N 0.000 claims 1
• ZGWQLOBGRDTDNI-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-(oxan-4-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CCOCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCCC1 ZGWQLOBGRDTDNI-UHFFFAOYSA-N 0.000 claims 1
• DNJPAXPYOSESEY-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCCC3)C2=N1 DNJPAXPYOSESEY-UHFFFAOYSA-N 0.000 claims 1
• SUPNECRXMVETSH-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-n-piperidin-4-ylbenzamide Chemical compound COC1=CC(C(=O)NC2CCNCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCCC1 SUPNECRXMVETSH-UHFFFAOYSA-N 0.000 claims 1
• AGLAFVGBYPTFSF-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCCC3)C2=N1 AGLAFVGBYPTFSF-UHFFFAOYSA-N 0.000 claims 1
• ZJJQPFRCTQEAIS-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCCC3)C2=N1 ZJJQPFRCTQEAIS-UHFFFAOYSA-N 0.000 claims 1
• HRGFYVLLNOAVFY-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-ethylpiperidin-4-yl)-3-methoxybenzamide Chemical compound C1CN(CC)CCC1NC(=O)C(C=C1OC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCCC3)C2=N1 HRGFYVLLNOAVFY-UHFFFAOYSA-N 0.000 claims 1
• YLADGQXKSNCGKS-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-ethylpiperidin-4-yl)benzamide Chemical compound C1CN(CC)CCC1NC(=O)C(C=C1)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCCC3)C2=N1 YLADGQXKSNCGKS-UHFFFAOYSA-N 0.000 claims 1
• GCXJBVYDGVPBCS-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1NC(=O)C(C=C1)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCCC3)C2=N1 GCXJBVYDGVPBCS-UHFFFAOYSA-N 0.000 claims 1
• PXLYQMIBLQYWRP-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(oxan-4-yl)benzamide Chemical compound N1=C2N(C3CCCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C=C1)=CC=C1C(=O)NC1CCOCC1 PXLYQMIBLQYWRP-UHFFFAOYSA-N 0.000 claims 1
• RKYMNZOWUOTBEK-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[1-(2,2-difluoroethyl)piperidin-4-yl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CCN(CC(F)F)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCCC1 RKYMNZOWUOTBEK-UHFFFAOYSA-N 0.000 claims 1
• FDEAOXUCYSKSBH-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[1-(2-hydroxyethyl)piperidin-4-yl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CCN(CCO)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCCC1 FDEAOXUCYSKSBH-UHFFFAOYSA-N 0.000 claims 1
• ZXIMKXCWMIZHHX-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[2-(dimethylamino)ethyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCCC3)C2=N1 ZXIMKXCWMIZHHX-UHFFFAOYSA-N 0.000 claims 1
• XBGZEXDIOCODLL-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[2-(dimethylamino)ethyl]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCCC3)C2=N1 XBGZEXDIOCODLL-UHFFFAOYSA-N 0.000 claims 1
• SDGSPTXHFKBIOR-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCCC3)C2=N1 SDGSPTXHFKBIOR-UHFFFAOYSA-N 0.000 claims 1
• RKVOJGVAISIHDB-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]benzamide Chemical compound C1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCCC3)C2=N1 RKVOJGVAISIHDB-UHFFFAOYSA-N 0.000 claims 1
• SFEDOHDRAWCOEB-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCCC3)C2=N1 SFEDOHDRAWCOEB-UHFFFAOYSA-N 0.000 claims 1
• GKPMVOVWWOBSJA-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-piperidin-4-ylbenzamide Chemical compound N1=C2N(C3CCCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C=C1)=CC=C1C(=O)NC1CCNCC1 GKPMVOVWWOBSJA-UHFFFAOYSA-N 0.000 claims 1
• OJNVHXMLCTZNGV-UHFFFAOYSA-N 4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]benzamide Chemical compound N1=C2N(C3CCCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC1=CC=C(C(N)=O)C=C1 OJNVHXMLCTZNGV-UHFFFAOYSA-N 0.000 claims 1
• SKEBOOPGDXDDDN-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2,5-difluoro-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1NC(=O)C(C(=C1)F)=CC(F)=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 SKEBOOPGDXDDDN-UHFFFAOYSA-N 0.000 claims 1
• JTFLRWFVYXSAOS-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2,5-difluoro-n-(oxan-4-yl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C(=C1)F)=CC(F)=C1C(=O)NC1CCOCC1 JTFLRWFVYXSAOS-UHFFFAOYSA-N 0.000 claims 1
• VDWGTPLOWNWQGN-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2,5-difluoro-n-methylbenzamide Chemical compound C1=C(F)C(C(=O)NC)=CC(F)=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 VDWGTPLOWNWQGN-UHFFFAOYSA-N 0.000 claims 1
• JHDSUJPDQFZEKI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2,5-difluoro-n-piperidin-4-ylbenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C(=C1)F)=CC(F)=C1C(=O)NC1CCNCC1 JHDSUJPDQFZEKI-UHFFFAOYSA-N 0.000 claims 1
• JXKCARWDXKMBGI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2,5-difluorobenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC1=CC(F)=C(C(N)=O)C=C1F JXKCARWDXKMBGI-UHFFFAOYSA-N 0.000 claims 1
• LUYHDUGQYPBZGP-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2,5-difluorobenzoic acid Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC1=CC(F)=C(C(O)=O)C=C1F LUYHDUGQYPBZGP-UHFFFAOYSA-N 0.000 claims 1
• FXGCQVSPPRYQAM-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethoxy-n-methylbenzamide Chemical compound CCOC1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 FXGCQVSPPRYQAM-UHFFFAOYSA-N 0.000 claims 1
• HLUONFKZMLAYCY-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethoxy-n-piperidin-4-ylbenzamide Chemical compound CCOC1=CC(C(=O)NC2CCNCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 HLUONFKZMLAYCY-UHFFFAOYSA-N 0.000 claims 1
• JCNZRYVEUXJGCI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-ethoxybenzamide Chemical compound CCOC1=CC(C(N)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 JCNZRYVEUXJGCI-UHFFFAOYSA-N 0.000 claims 1
• WZBUBWITXSQWLR-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-fluoro-n-(oxan-4-yl)benzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C(=C1)F)=CC=C1C(=O)NC1CCOCC1 WZBUBWITXSQWLR-UHFFFAOYSA-N 0.000 claims 1
• DLSFXYQPELZWEZ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-fluoro-n-methylbenzamide Chemical compound FC1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 DLSFXYQPELZWEZ-UHFFFAOYSA-N 0.000 claims 1
• YWWBXCRLCNKINB-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-fluoro-n-piperidin-4-ylbenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC(C(=C1)F)=CC=C1C(=O)NC1CCNCC1 YWWBXCRLCNKINB-UHFFFAOYSA-N 0.000 claims 1
• MAKAIJXKQUTJTJ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-fluorobenzamide Chemical compound N1=C2N(C3CCCC3)CC(F)(F)C(=O)N(C)C2=CN=C1NC1=CC=C(C(N)=O)C=C1F MAKAIJXKQUTJTJ-UHFFFAOYSA-N 0.000 claims 1
• NPPHMOYTHILRBX-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-ethylpiperidin-4-yl)-2,5-difluorobenzamide Chemical compound C1CN(CC)CCC1NC(=O)C(C(=C1)F)=CC(F)=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 NPPHMOYTHILRBX-UHFFFAOYSA-N 0.000 claims 1
• ZOJWJHKYZDEFMQ-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-ethylpiperidin-4-yl)-3-fluorobenzamide Chemical compound C1CN(CC)CCC1NC(=O)C(C=C1F)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 ZOJWJHKYZDEFMQ-UHFFFAOYSA-N 0.000 claims 1
• KLODPNJUOYRALG-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[2-(dimethylamino)ethyl]-2,5-difluorobenzamide Chemical compound C1=C(F)C(C(=O)NCCN(C)C)=CC(F)=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 KLODPNJUOYRALG-UHFFFAOYSA-N 0.000 claims 1
• SAZVLMGBIDCDFM-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-2,5-difluorobenzamide Chemical compound C1=C(F)C(C(=O)NCCCN(C)C)=CC(F)=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 SAZVLMGBIDCDFM-UHFFFAOYSA-N 0.000 claims 1
• NSPNACLUIZEWKW-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-[3-(dimethylamino)propyl]-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 NSPNACLUIZEWKW-UHFFFAOYSA-N 0.000 claims 1
• PNFWQWFXIKTIPN-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2,3-difluoro-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1NC(=O)C(C(=C1F)F)=CC=C1NC1=NC=C(NC(=O)C(F)(F)CN2C3CCCC3)C2=N1 PNFWQWFXIKTIPN-UHFFFAOYSA-N 0.000 claims 1
• IKZDOPRZUPWTHM-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2,3-difluoro-n-methylbenzamide Chemical compound FC1=C(F)C(C(=O)NC)=CC=C1NC1=NC=C(NC(=O)C(F)(F)CN2C3CCCC3)C2=N1 IKZDOPRZUPWTHM-UHFFFAOYSA-N 0.000 claims 1
• KOXGESDGCSTWOK-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-6-oxo-5,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl)amino]-n-(1-ethylpiperidin-4-yl)-2,3-difluorobenzamide Chemical compound C1CN(CC)CCC1NC(=O)C(C(=C1F)F)=CC=C1NC1=NC=C(NC(=O)C(F)(F)CN2C3CCCC3)C2=N1 KOXGESDGCSTWOK-UHFFFAOYSA-N 0.000 claims 1
• FZORPKVINHUJOU-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(2-phenoxyethyl)-8h-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=C1N(C)C(=O)C(F)(F)CN2CCOC1=CC=CC=C1 FZORPKVINHUJOU-UHFFFAOYSA-N 0.000 claims 1
• XJDFPABNFMGUQZ-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(2-phenylethyl)-8h-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=C1N(C)C(=O)C(F)(F)CN2CCC1=CC=CC=C1 XJDFPABNFMGUQZ-UHFFFAOYSA-N 0.000 claims 1
• TUQMYIJNTSGUGF-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(2-phenylethyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxy-n-(oxan-4-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CCOCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2CCC1=CC=CC=C1 TUQMYIJNTSGUGF-UHFFFAOYSA-N 0.000 claims 1
• PSUBGYPXALNCMG-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(2-phenylethyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2CCC=3C=CC=CC=3)C2=N1 PSUBGYPXALNCMG-UHFFFAOYSA-N 0.000 claims 1
• XSDGPZQANIZACZ-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(2-phenylethyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2CCC=3C=CC=CC=3)C2=N1 XSDGPZQANIZACZ-UHFFFAOYSA-N 0.000 claims 1
• PCPAXXKTKQUPHR-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(2-phenylethyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2CCC=3C=CC=CC=3)C2=N1 PCPAXXKTKQUPHR-UHFFFAOYSA-N 0.000 claims 1
• NGAFYUZTCNBCGI-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(2-phenylethyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-n-[3-(dimethylamino)propyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2CCC=3C=CC=CC=3)C2=N1 NGAFYUZTCNBCGI-UHFFFAOYSA-N 0.000 claims 1
• KVBACVCSBJSAER-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(2-thiophen-2-ylethyl)-8h-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=C1N(C)C(=O)C(F)(F)CN2CCC1=CC=CS1 KVBACVCSBJSAER-UHFFFAOYSA-N 0.000 claims 1
• DGGHCJPFKMNPAU-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(2-thiophen-2-ylethyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxy-n-(oxan-4-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CCOCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2CCC1=CC=CS1 DGGHCJPFKMNPAU-UHFFFAOYSA-N 0.000 claims 1
• JSFTXPUPTJTYTB-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(2-thiophen-2-ylethyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2CCC=3SC=CC=3)C2=N1 JSFTXPUPTJTYTB-UHFFFAOYSA-N 0.000 claims 1
• KMWJCCMWYIKRNP-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(2-thiophen-2-ylethyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2CCC=3SC=CC=3)C2=N1 KMWJCCMWYIKRNP-UHFFFAOYSA-N 0.000 claims 1
• MNHDFLRMCRZSOS-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(2-thiophen-2-ylethyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-n-[3-(dimethylamino)propyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2CCC=3SC=CC=3)C2=N1 MNHDFLRMCRZSOS-UHFFFAOYSA-N 0.000 claims 1
• QIMBUKMFWMBEHR-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(3-phenylpropyl)-8h-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=C1N(C)C(=O)C(F)(F)CN2CCCC1=CC=CC=C1 QIMBUKMFWMBEHR-UHFFFAOYSA-N 0.000 claims 1
• PHXLWWFFQDNSSE-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(3-phenylpropyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxy-n-(oxan-4-yl)benzamide Chemical compound COC1=CC(C(=O)NC2CCOCC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2CCCC1=CC=CC=C1 PHXLWWFFQDNSSE-UHFFFAOYSA-N 0.000 claims 1
• DMMUXYAYHYDDLV-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(3-phenylpropyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2CCCC=3C=CC=CC=3)C2=N1 DMMUXYAYHYDDLV-UHFFFAOYSA-N 0.000 claims 1
• UXZZINQYOKUPEO-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(3-phenylpropyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2CCCC=3C=CC=CC=3)C2=N1 UXZZINQYOKUPEO-UHFFFAOYSA-N 0.000 claims 1
• XXIJBRADQSRHDK-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(3-phenylpropyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2CCCC=3C=CC=CC=3)C2=N1 XXIJBRADQSRHDK-UHFFFAOYSA-N 0.000 claims 1
• GHTYTXXJOCCCQB-UHFFFAOYSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-(3-phenylpropyl)-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-n-[3-(dimethylamino)propyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2CCCC=3C=CC=CC=3)C2=N1 GHTYTXXJOCCCQB-UHFFFAOYSA-N 0.000 claims 1
• AVYWETQIOGLARX-FUHWJXTLSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-[(1r,2s)-2-phenylcyclopropyl]-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2[C@H]3[C@@H](C3)C=3C=CC=CC=3)C2=N1 AVYWETQIOGLARX-FUHWJXTLSA-N 0.000 claims 1
• IXGLPNQCLBXUHO-FUHWJXTLSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-[(1r,2s)-2-phenylcyclopropyl]-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2[C@H]3[C@@H](C3)C=3C=CC=CC=3)C2=N1 IXGLPNQCLBXUHO-FUHWJXTLSA-N 0.000 claims 1
• IWZPVFATWJHPPC-JTHBVZDNSA-N 4-[[7,7-difluoro-5-methyl-6-oxo-9-[(1r,2s)-2-phenylcyclopropyl]-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-n-[3-(dimethylamino)propyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2[C@H]3[C@@H](C3)C=3C=CC=CC=3)C2=N1 IWZPVFATWJHPPC-JTHBVZDNSA-N 0.000 claims 1
• GLTMSDBAMFENHK-UHFFFAOYSA-N 4-[[7,7-difluoro-9-[(4-methoxyphenyl)methyl]-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl]amino]-3-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1=CC(OC)=CC=C1CN1C2=NC(NC=3C(=CC(=CC=3)C(=O)NC3CCN(C)CC3)OC)=NC=C2N(C)C(=O)C(F)(F)C1 GLTMSDBAMFENHK-UHFFFAOYSA-N 0.000 claims 1
• USPFWUYOJAKGOU-PLQXJYEYSA-N C1CN([C@@H]2CC[C@@H](CC2)NC(=O)C=2C=C(C(=CC=2)NC=2N=C3N(C(C)C)CC(F)(F)C(=O)N(C)C3=CN=2)OC)CCN1CC1CC1 Chemical compound C1CN([C@@H]2CC[C@@H](CC2)NC(=O)C=2C=C(C(=CC=2)NC=2N=C3N(C(C)C)CC(F)(F)C(=O)N(C)C3=CN=2)OC)CCN1CC1CC1 USPFWUYOJAKGOU-PLQXJYEYSA-N 0.000 claims 1
• USPFWUYOJAKGOU-SOAUALDESA-N C1CN([C@H]2CC[C@@H](CC2)NC(=O)C=2C=C(C(=CC=2)NC=2N=C3N(C(C)C)CC(F)(F)C(=O)N(C)C3=CN=2)OC)CCN1CC1CC1 Chemical compound C1CN([C@H]2CC[C@@H](CC2)NC(=O)C=2C=C(C(=CC=2)NC=2N=C3N(C(C)C)CC(F)(F)C(=O)N(C)C3=CN=2)OC)CCN1CC1CC1 USPFWUYOJAKGOU-SOAUALDESA-N 0.000 claims 1
• FWZMTAVQGNDTNM-WMPKNSHKSA-N COC1=CC(C(=O)N[C@@H]2CC[C@@H](CC2)N2CCN(CC3CC3)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 Chemical compound COC1=CC(C(=O)N[C@@H]2CC[C@@H](CC2)N2CCN(CC3CC3)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 FWZMTAVQGNDTNM-WMPKNSHKSA-N 0.000 claims 1
• FWZMTAVQGNDTNM-DIVCQZSQSA-N COC1=CC(C(=O)N[C@@H]2CC[C@H](CC2)N2CCN(CC3CC3)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 Chemical compound COC1=CC(C(=O)N[C@@H]2CC[C@H](CC2)N2CCN(CC3CC3)CC2)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCC1 FWZMTAVQGNDTNM-DIVCQZSQSA-N 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 claims 1
• RUGAMBHGZUMJLN-UHFFFAOYSA-N methyl 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2,3-difluorobenzoate Chemical compound FC1=C(F)C(C(=O)OC)=CC=C1NC1=NC=C(N(C)C(=O)C(F)(F)CN2C3CCCC3)C2=N1 RUGAMBHGZUMJLN-UHFFFAOYSA-N 0.000 claims 1
• AROXHAPNPSUGBQ-UHFFFAOYSA-N tert-butyl 4-[[4-[(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoyl]amino]piperidine-1-carboxylate Chemical compound COC1=CC(C(=O)NC2CCN(CC2)C(=O)OC(C)(C)C)=CC=C1NC(N=C12)=NC=C1N(C)C(=O)C(F)(F)CN2C1CCCCC1 AROXHAPNPSUGBQ-UHFFFAOYSA-N 0.000 claims 1
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