CA3064975A1 - Novel inhibitors of map4k1 - Google Patents

Info

Publication number

CA3064975A1

CA3064975A1 CA3064975A CA3064975A CA3064975A1 CA 3064975 A1 CA3064975 A1 CA 3064975A1 CA 3064975 A CA3064975 A CA 3064975A CA 3064975 A CA3064975 A CA 3064975A CA 3064975 A1 CA3064975 A1 CA 3064975A1

Authority

CA

Canada

Prior art keywords

phenyl

oxy

trifluoromethyl

oxazin

dihydro

Prior art date

2017-05-26

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
• CIPO
• Discuss

• 239000003112 inhibitor Substances 0.000 title abstract description 30
• 238000000034 method Methods 0.000 claims abstract description 186
• 102100028199 Mitogen-activated protein kinase kinase kinase kinase 1 Human genes 0.000 claims abstract description 55
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 52
• 101001059991 Homo sapiens Mitogen-activated protein kinase kinase kinase kinase 1 Proteins 0.000 claims abstract description 42
• 201000010099 disease Diseases 0.000 claims abstract description 30
• 208000035475 disorder Diseases 0.000 claims abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 7
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 7
• 150000001875 compounds Chemical class 0.000 claims description 437
• -1 cyano, hydroxyl Chemical group 0.000 claims description 129
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 97
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 81
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 62
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 25
• 150000001412 amines Chemical class 0.000 claims description 24
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 22
• 125000005843 halogen group Chemical group 0.000 claims description 22
• 239000004202 carbamide Substances 0.000 claims description 19
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 206010028980 Neoplasm Diseases 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
• 201000011510 cancer Diseases 0.000 claims description 10
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 150000002367 halogens Chemical group 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 206010011878 Deafness Diseases 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 208000016354 hearing loss disease Diseases 0.000 claims description 6
• 125000001246 bromo group Chemical group Br* 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 210000004185 liver Anatomy 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical group N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 claims description 4
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
• 230000001404 mediated effect Effects 0.000 claims description 4
• 230000000926 neurological effect Effects 0.000 claims description 4
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 3
• 206010006187 Breast cancer Diseases 0.000 claims description 3
• 208000026310 Breast neoplasm Diseases 0.000 claims description 3
• 206010009944 Colon cancer Diseases 0.000 claims description 3
• 208000032170 Congenital Abnormalities Diseases 0.000 claims description 3
• 206010010356 Congenital anomaly Diseases 0.000 claims description 3
• 206010020751 Hypersensitivity Diseases 0.000 claims description 3
• 206010022491 Insulin resistant diabetes Diseases 0.000 claims description 3
• 208000008589 Obesity Diseases 0.000 claims description 3
• 208000018737 Parkinson disease Diseases 0.000 claims description 3
• 230000007815 allergy Effects 0.000 claims description 3
• 208000006673 asthma Diseases 0.000 claims description 3
• 230000001363 autoimmune Effects 0.000 claims description 3
• 235000010290 biphenyl Nutrition 0.000 claims description 3
• 230000007698 birth defect Effects 0.000 claims description 3
• 231100000895 deafness Toxicity 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
• 230000010370 hearing loss Effects 0.000 claims description 3
• 231100000888 hearing loss Toxicity 0.000 claims description 3
• 230000002757 inflammatory effect Effects 0.000 claims description 3
• 208000028867 ischemia Diseases 0.000 claims description 3
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
• 210000000276 neural tube Anatomy 0.000 claims description 3
• 230000000626 neurodegenerative effect Effects 0.000 claims description 3
• 235000020824 obesity Nutrition 0.000 claims description 3
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
• 125000001424 substituent group Chemical group 0.000 claims description 3
• 208000024827 Alzheimer disease Diseases 0.000 claims description 2
• 208000000044 Amnesia Diseases 0.000 claims description 2
• 206010003571 Astrocytoma Diseases 0.000 claims description 2
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
• 206010014733 Endometrial cancer Diseases 0.000 claims description 2
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 2
• 206010014967 Ependymoma Diseases 0.000 claims description 2
• 208000026139 Memory disease Diseases 0.000 claims description 2
• 206010033128 Ovarian cancer Diseases 0.000 claims description 2
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
• 206010060862 Prostate cancer Diseases 0.000 claims description 2
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
• 206010063837 Reperfusion injury Diseases 0.000 claims description 2
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
• 206010041067 Small cell lung cancer Diseases 0.000 claims description 2
• 208000006011 Stroke Diseases 0.000 claims description 2
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
• 208000009956 adenocarcinoma Diseases 0.000 claims description 2
• 206010003246 arthritis Diseases 0.000 claims description 2
• 201000007455 central nervous system cancer Diseases 0.000 claims description 2
• 208000005017 glioblastoma Diseases 0.000 claims description 2
• 210000003734 kidney Anatomy 0.000 claims description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
• 201000001441 melanoma Diseases 0.000 claims description 2
• 230000006984 memory degeneration Effects 0.000 claims description 2
• 208000023060 memory loss Diseases 0.000 claims description 2
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 2
• 230000004792 oxidative damage Effects 0.000 claims description 2
• 201000002528 pancreatic cancer Diseases 0.000 claims description 2
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
• 201000002025 prostate sarcoma Diseases 0.000 claims description 2
• 208000000587 small cell lung carcinoma Diseases 0.000 claims description 2
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 8
• 208000011580 syndromic disease Diseases 0.000 claims 4
• PFIIRRBUELNRIT-UHFFFAOYSA-N 4-chloro-3-[(7,7-dimethyl-6,8-dihydropyrimido[5,4-b][1,4]oxazin-4-yl)oxy]-N-[4-[1-(4-ethylpiperazin-1-yl)ethyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)C(C)N2CCN(CC2)CC)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCC(N2)(C)C PFIIRRBUELNRIT-UHFFFAOYSA-N 0.000 claims 2
• MZVMFHJRXZPZBT-UHFFFAOYSA-N 1-N'-[4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-3-fluorophenyl]-1-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound N1=CN=C(C=2OCCNC=21)OC1=C(C=C(C=C1)N(C(=O)C1(CC1)C(=O)N)C1=CC=C(C=C1)F)F MZVMFHJRXZPZBT-UHFFFAOYSA-N 0.000 claims 1
• CNMJOUAUKAHYRW-SECBINFHSA-N 1-[2-chloro-4-[[(7R)-7-methyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]phenyl]-3-cyclopropylurea Chemical compound ClC1=C(C=CC(=C1)OC1=NC=NC2=C1OC[C@H](N2)C)NC(=O)NC1CC1 CNMJOUAUKAHYRW-SECBINFHSA-N 0.000 claims 1
• UTKNBKBXXHBBIT-UHFFFAOYSA-N 1-[3-chloro-4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)phenyl]-3-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]urea Chemical compound ClC=1C=C(C=CC=1OC1=NC=NC2=C1OCCN2)NC(=O)NC1=CC(=CC(=C1)C(F)(F)F)N1CCN(CC1)C UTKNBKBXXHBBIT-UHFFFAOYSA-N 0.000 claims 1
• GXTMQKHJGOUHMX-UHFFFAOYSA-N 1-[3-chloro-4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound ClC=1C=C(C=CC=1OC1=NC=NC2=C1OCCN2)NC(=O)NC1=CC(=CC=C1)C(F)(F)F GXTMQKHJGOUHMX-UHFFFAOYSA-N 0.000 claims 1
• FAWADDRRVWSJKE-UHFFFAOYSA-N 1-[3-chloro-4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)phenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]urea Chemical compound ClC=1C=C(C=CC=1OC1=NC=NC2=C1OCCN2)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F FAWADDRRVWSJKE-UHFFFAOYSA-N 0.000 claims 1
• QNGNQSWHWNXLNW-UHFFFAOYSA-N 1-[3-chloro-4-[(7,7-dimethyl-6,8-dihydropyrimido[5,4-b][1,4]oxazin-4-yl)oxy]phenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]urea Chemical compound ClC=1C=C(C=CC=1OC1=NC=NC2=C1OCC(N2)(C)C)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F QNGNQSWHWNXLNW-UHFFFAOYSA-N 0.000 claims 1
• XGDQGUQLLPVGCG-QGZVFWFLSA-N 1-[3-chloro-4-[[(7R)-7-methyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]phenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]urea Chemical compound ClC=1C=C(C=CC=1OC1=NC=NC2=C1OC[C@H](N2)C)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F XGDQGUQLLPVGCG-QGZVFWFLSA-N 0.000 claims 1
• BVOJZYIBCFRQOX-UHFFFAOYSA-N 1-[4-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yloxy)phenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]urea Chemical compound O1C2=C(NCC1)N=CC(=C2)OC1=CC=C(C=C1)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F BVOJZYIBCFRQOX-UHFFFAOYSA-N 0.000 claims 1
• FUCUYEJZESTBTA-UHFFFAOYSA-N 1-[4-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)phenyl]-3-(3-ethylsulfonylphenyl)urea Chemical compound O1C2=C(NCC1)N=CC=C2OC1=CC=C(C=C1)NC(=O)NC1=CC(=CC=C1)S(=O)(=O)CC FUCUYEJZESTBTA-UHFFFAOYSA-N 0.000 claims 1
• QPTFNIOCFDLHHA-UHFFFAOYSA-N 1-[4-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)phenyl]-3-(3-methylsulfonylphenyl)urea Chemical compound O1C2=C(NCC1)N=CC=C2OC1=CC=C(C=C1)NC(=O)NC1=CC(=CC=C1)S(=O)(=O)C QPTFNIOCFDLHHA-UHFFFAOYSA-N 0.000 claims 1
• OOEIZDDBADAMEV-UHFFFAOYSA-N 1-[4-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)phenyl]-3-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]urea Chemical compound O1C2=C(NCC1)N=CC=C2OC1=CC=C(C=C1)NC(=O)NC1=CC(=CC(=C1)C(F)(F)F)N1CCN(CC1)C OOEIZDDBADAMEV-UHFFFAOYSA-N 0.000 claims 1
• DQXJLYUMMINNAK-UHFFFAOYSA-N 1-[4-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)phenyl]-3-[3-(4-methylpiperazin-1-yl)-5-methylsulfonylphenyl]urea Chemical compound O1C2=C(NCC1)N=CC=C2OC1=CC=C(C=C1)NC(=O)NC1=CC(=CC(=C1)S(=O)(=O)C)N1CCN(CC1)C DQXJLYUMMINNAK-UHFFFAOYSA-N 0.000 claims 1
• RIDPLZNQPTYOTO-UHFFFAOYSA-N 1-[4-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)phenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]urea Chemical compound O1C2=C(NCC1)N=CC=C2OC1=CC=C(C=C1)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F RIDPLZNQPTYOTO-UHFFFAOYSA-N 0.000 claims 1
• KYZVKGTYDYKCPP-UHFFFAOYSA-N 1-[4-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)phenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-methylsulfonylphenyl]urea Chemical compound O1C2=C(NCC1)N=CC=C2OC1=CC=C(C=C1)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)S(=O)(=O)C KYZVKGTYDYKCPP-UHFFFAOYSA-N 0.000 claims 1
• JNQAOVGJXWFUSZ-UHFFFAOYSA-N 1-[4-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)phenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]urea Chemical compound O1C2=C(NCC1)N=CC=C2OC1=CC=C(C=C1)NC(=O)NC1=CC=C(C=C1)CN1CCN(CC1)CC JNQAOVGJXWFUSZ-UHFFFAOYSA-N 0.000 claims 1
• JSVSKDSIBUMLGT-UHFFFAOYSA-N 1-[4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-2-fluorophenyl]-3-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]urea Chemical compound N1=CN=C(C=2OCCNC=21)OC1=CC(=C(C=C1)NC(=O)NC1=CC(=CC(=C1)C(F)(F)F)N1CCN(CC1)C)F JSVSKDSIBUMLGT-UHFFFAOYSA-N 0.000 claims 1
• PVWJQRZZTWXWCB-UHFFFAOYSA-N 1-[4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-2-fluorophenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]urea Chemical compound N1=CN=C(C=2OCCNC=21)OC1=CC(=C(C=C1)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F)F PVWJQRZZTWXWCB-UHFFFAOYSA-N 0.000 claims 1
• GYWVBSDLZQIUKC-UHFFFAOYSA-N 1-[4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-3-methylphenyl]-3-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]urea Chemical compound N1=CN=C(C=2OCCNC=21)OC1=C(C=C(C=C1)NC(=O)NC1=CC(=CC(=C1)C(F)(F)F)N1CCN(CC1)C)C GYWVBSDLZQIUKC-UHFFFAOYSA-N 0.000 claims 1
• KBPRCEKFQCIDEY-UHFFFAOYSA-N 1-[4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-3-methylphenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]urea Chemical compound N1=CN=C(C=2OCCNC=21)OC1=C(C=C(C=C1)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F)C KBPRCEKFQCIDEY-UHFFFAOYSA-N 0.000 claims 1
• BIQJSODOWSKQEW-UHFFFAOYSA-N 1-[4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)phenyl]-3-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]urea Chemical compound N1=CN=C(C=2OCCNC=21)OC1=CC=C(C=C1)NC(=O)NC1=CC(=CC(=C1)C(F)(F)F)N1CCN(CC1)C BIQJSODOWSKQEW-UHFFFAOYSA-N 0.000 claims 1
• FQXLRXLECVAFGD-UHFFFAOYSA-N 1-[4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound N1=CN=C(C=2OCCNC=21)OC1=CC=C(C=C1)NC(=O)NC1=CC(=CC=C1)C(F)(F)F FQXLRXLECVAFGD-UHFFFAOYSA-N 0.000 claims 1
• XZKPMOBCASZGSE-UHFFFAOYSA-N 1-[4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)phenyl]-3-[3-[(4-ethylpiperazin-1-yl)methyl]-5-(trifluoromethyl)phenyl]urea hydrochloride Chemical compound Cl.N1=CN=C(C=2OCCNC=21)OC1=CC=C(C=C1)NC(=O)NC1=CC(=CC(=C1)C(F)(F)F)CN1CCN(CC1)CC XZKPMOBCASZGSE-UHFFFAOYSA-N 0.000 claims 1
• LANCJYAEHAIZLC-UHFFFAOYSA-N 1-[4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)phenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]urea Chemical compound N1=CN=C(C=2OCCNC=21)OC1=CC=C(C=C1)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F LANCJYAEHAIZLC-UHFFFAOYSA-N 0.000 claims 1
• KHMFJWPPLJCLMW-UHFFFAOYSA-N 1-[4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)phenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]urea Chemical compound N1=CN=C(C=2OCCNC=21)OC1=CC=C(C=C1)NC(=O)NC1=CC=C(C=C1)CN1CCN(CC1)CC KHMFJWPPLJCLMW-UHFFFAOYSA-N 0.000 claims 1
• FWBPDSUOMDGNQQ-UHFFFAOYSA-N 1-[4-[(7,7-dimethyl-6,8-dihydropyrimido[5,4-b][1,4]oxazin-4-yl)oxy]-3-fluorophenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]urea Chemical compound CC1(NC2=C(OC1)C(=NC=N2)OC1=C(C=C(C=C1)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F)F)C FWBPDSUOMDGNQQ-UHFFFAOYSA-N 0.000 claims 1
• ZRRDIORNKUHCKZ-UHFFFAOYSA-N 1-[4-[(7,7-dimethyl-6,8-dihydropyrimido[5,4-b][1,4]oxazin-4-yl)oxy]-3-methylphenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]urea Chemical compound CC1(NC2=C(OC1)C(=NC=N2)OC1=C(C=C(C=C1)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F)C)C ZRRDIORNKUHCKZ-UHFFFAOYSA-N 0.000 claims 1
• XEWYXVZOENBTAM-UHFFFAOYSA-N 1-[4-[(7-cyano-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yl)oxy]phenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]urea Chemical compound C(#N)C1=C(C=2OCCNC=2N=C1)OC1=CC=C(C=C1)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F XEWYXVZOENBTAM-UHFFFAOYSA-N 0.000 claims 1
• JQTLMTRXMKOCST-UHFFFAOYSA-N 1-[4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)phenyl]-3-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]urea Chemical compound ClC1=C(C=C(C=C1)NC(=O)NC1=CC(=CC(=C1)C(F)(F)F)N1CCN(CC1)C)OC1=NC=NC2=C1OCCN2 JQTLMTRXMKOCST-UHFFFAOYSA-N 0.000 claims 1
• FSLJRMWPOWDGPQ-UHFFFAOYSA-N 1-[4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)phenyl]-3-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]urea Chemical compound ClC1=C(C=C(C=C1)NC(=O)NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F)OC1=NC=NC2=C1OCCN2 FSLJRMWPOWDGPQ-UHFFFAOYSA-N 0.000 claims 1
• PAXCUEMYDPSBMN-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-cyanophenyl)pyrazol-3-yl]-3-[2-fluoro-4-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-9-yloxy)phenyl]urea Chemical compound C(C)(C)(C)C1=NN(C(=C1)NC(=O)NC1=C(C=C(C=C1)OC1=CC=NC2=C1OCCCN2)F)C1=CC=C(C=C1)C#N PAXCUEMYDPSBMN-UHFFFAOYSA-N 0.000 claims 1
• YSZSQHXCWCMZNH-UHFFFAOYSA-N 2-chloro-5-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C(C=C1)OC1=NC=NC2=C1OCCN2 YSZSQHXCWCMZNH-UHFFFAOYSA-N 0.000 claims 1
• BAWSLSJWZQSFOJ-UHFFFAOYSA-N 3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)-4-methyl-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound O1C2=C(NCC1)N=CC=C2OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=CC=1C BAWSLSJWZQSFOJ-UHFFFAOYSA-N 0.000 claims 1
• WUBUDJJXVLGZOJ-UHFFFAOYSA-N 3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)-4-methyl-N-[3-morpholin-4-yl-5-(trifluoromethyl)phenyl]benzamide Chemical compound O1C2=C(NCC1)N=CC=C2OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCOCC2)C=CC=1C WUBUDJJXVLGZOJ-UHFFFAOYSA-N 0.000 claims 1
• DHEIRGRXFCPTJA-UHFFFAOYSA-N 3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)-N-[3-(4-ethylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound O1C2=C(NCC1)N=CC=C2OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)CC)C=CC=1C DHEIRGRXFCPTJA-UHFFFAOYSA-N 0.000 claims 1
• ZKJYUMNYGMNETR-NRFANRHFSA-N 3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)-N-[3-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound O1C2=C(NCC1)N=CC=C2OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C[C@H](CC2)N(C)C)C=CC=1C ZKJYUMNYGMNETR-NRFANRHFSA-N 0.000 claims 1
• VHJXKGZIAAQRGC-UHFFFAOYSA-N 3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)-N-[3-[(4-ethylpiperazin-1-yl)methyl]-5-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound O1C2=C(NCC1)N=CC=C2OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)CN2CCN(CC2)CC)C=CC=1C VHJXKGZIAAQRGC-UHFFFAOYSA-N 0.000 claims 1
• YCRYYRVQRKOSTG-UHFFFAOYSA-N 3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound O1C2=C(NCC1)N=CC=C2OC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=CC=1C YCRYYRVQRKOSTG-UHFFFAOYSA-N 0.000 claims 1
• YIHOWGNVNNGMMF-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-4-methyl-N-(3-methylsulfonylphenyl)benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC=C2)S(=O)(=O)C)C=CC=1C YIHOWGNVNNGMMF-UHFFFAOYSA-N 0.000 claims 1
• MTBHUEYKZHSHLG-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-4-methyl-N-[3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C=NC(=C2)C)C=CC=1C MTBHUEYKZHSHLG-UHFFFAOYSA-N 0.000 claims 1
• DIRLXTJOCLFRBB-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-4-methyl-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=CC=1C DIRLXTJOCLFRBB-UHFFFAOYSA-N 0.000 claims 1
• GGEGPLLZIRBDTN-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-4-methyl-N-[3-(4-propan-2-ylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C(C)C)C=CC=1C GGEGPLLZIRBDTN-UHFFFAOYSA-N 0.000 claims 1
• ZVCTZXFTLAZYPE-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-4-methyl-N-[3-(4-propylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)CCC)C=CC=1C ZVCTZXFTLAZYPE-UHFFFAOYSA-N 0.000 claims 1
• QMSJXIRBUXDTBZ-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-4-methyl-N-[3-morpholin-4-yl-5-(trifluoromethyl)phenyl]benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCOCC2)C=CC=1C QMSJXIRBUXDTBZ-UHFFFAOYSA-N 0.000 claims 1
• BSZKJKFYHIANIL-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-4-methyl-N-[4-(trifluoromethyl)phenyl]benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC=C(C=C2)C(F)(F)F)C=CC=1C BSZKJKFYHIANIL-UHFFFAOYSA-N 0.000 claims 1
• CITVUAMROSDODS-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-4-methyl-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)C)C(F)(F)F)C=CC=1C CITVUAMROSDODS-UHFFFAOYSA-N 0.000 claims 1
• ADGCLPBPJAQFMH-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-4-methyl-N-[4-[(4-propan-2-ylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)C(C)C)C(F)(F)F)C=CC=1C ADGCLPBPJAQFMH-UHFFFAOYSA-N 0.000 claims 1
• CUZNMZPITSXYTD-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-(3-ethylsulfonylphenyl)-4-methylbenzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC=C2)S(=O)(=O)CC)C=CC=1C CUZNMZPITSXYTD-UHFFFAOYSA-N 0.000 claims 1
• BVBGYFUTDOBWOD-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[2-fluoro-5-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=C(C=CC(=C2)C(F)(F)F)F)C=CC=1C BVBGYFUTDOBWOD-UHFFFAOYSA-N 0.000 claims 1
• MUQQKJPHZLSHDZ-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(3-hydroxy-3-methylbut-1-ynyl)-5-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C#CC(C)(C)O)C=CC=1C MUQQKJPHZLSHDZ-UHFFFAOYSA-N 0.000 claims 1
• GLMBUGSAYGDGJA-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(3-hydroxyprop-1-ynyl)-5-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C#CCO)C=CC=1C GLMBUGSAYGDGJA-UHFFFAOYSA-N 0.000 claims 1
• DWQKCBOEQNDXOF-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(3-methoxyprop-1-ynyl)-5-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C#CCOC)C=CC=1C DWQKCBOEQNDXOF-UHFFFAOYSA-N 0.000 claims 1
• AYVGRYOLNPRSBP-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(4-ethylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)CC)C=CC=1C AYVGRYOLNPRSBP-UHFFFAOYSA-N 0.000 claims 1
• LGGRNQIYNSOZHE-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=CC=1 LGGRNQIYNSOZHE-UHFFFAOYSA-N 0.000 claims 1
• WEZPPJUVCCMMHU-HXUWFJFHSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C[C@@H](CC2)N(C)C)C=CC=1C WEZPPJUVCCMMHU-HXUWFJFHSA-N 0.000 claims 1
• FUWSFBUPXLBGJN-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(4-ethylpiperazin-1-yl)methyl]-5-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)CN2CCN(CC2)CC)C=CC=1C FUWSFBUPXLBGJN-UHFFFAOYSA-N 0.000 claims 1
• DQQYQIZWXVINOK-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-2-methylbenzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C(=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=CC=1)C DQQYQIZWXVINOK-UHFFFAOYSA-N 0.000 claims 1
• VFCLRFQWIIBSOU-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-(trifluoromethyl)benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=CC=1C(F)(F)F VFCLRFQWIIBSOU-UHFFFAOYSA-N 0.000 claims 1
• WQXBLGBPLHKCQI-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-fluorobenzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=CC=1F WQXBLGBPLHKCQI-UHFFFAOYSA-N 0.000 claims 1
• JMKXLINSAOOMSN-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methoxybenzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=CC=1OC JMKXLINSAOOMSN-UHFFFAOYSA-N 0.000 claims 1
• BBOQEQPHNKPGNT-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=CC=1C BBOQEQPHNKPGNT-UHFFFAOYSA-N 0.000 claims 1
• NISOISZETNYBAH-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-5-(trifluoromethyl)benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C(C=1)C(F)(F)F NISOISZETNYBAH-UHFFFAOYSA-N 0.000 claims 1
• MCXGWFJRGQSVEG-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=CC=1 MCXGWFJRGQSVEG-UHFFFAOYSA-N 0.000 claims 1
• OQDXRWPPJWBCRE-UHFFFAOYSA-N 3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-ylsulfanyl)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound N1=CN=C(C=2OCCNC=21)SC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=CC=1C OQDXRWPPJWBCRE-UHFFFAOYSA-N 0.000 claims 1
• BIVCEERWAPPQMM-UHFFFAOYSA-N 3-[(7,7-dimethyl-6,8-dihydropyrimido[5,4-b][1,4]oxazin-4-yl)oxy]-4-methyl-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound CC1(NC2=C(OC1)C(=NC=N2)OC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=CC=1C)C BIVCEERWAPPQMM-UHFFFAOYSA-N 0.000 claims 1
• SZZMAYHLZUTIMR-UHFFFAOYSA-N 3-[(7,7-dimethyl-6,8-dihydropyrimido[5,4-b][1,4]oxazin-4-yl)oxy]-4-methyl-N-[3-(4-methylpiperazin-1-yl)-5-methylsulfonylphenyl]benzamide Chemical compound CC1(NC2=C(OC1)C(=NC=N2)OC=1C=C(C(=O)NC2=CC(=CC(=C2)S(=O)(=O)C)N2CCN(CC2)C)C=CC=1C)C SZZMAYHLZUTIMR-UHFFFAOYSA-N 0.000 claims 1
• RSGZZCYIOQBLGE-UHFFFAOYSA-N 3-[(7,7-dimethyl-6,8-dihydropyrimido[5,4-b][1,4]oxazin-4-yl)oxy]-N-[4-(4-hydroxybut-1-ynyl)-3-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound CC1(NC2=C(OC1)C(=NC=N2)OC=1C=C(C(=O)NC2=CC(=C(C=C2)C#CCCO)C(F)(F)F)C=CC=1C)C RSGZZCYIOQBLGE-UHFFFAOYSA-N 0.000 claims 1
• YRGCZVSKUACKQH-UHFFFAOYSA-N 3-[(7,7-dimethyl-6,8-dihydropyrimido[5,4-b][1,4]oxazin-4-yl)oxy]-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound CC1(NC2=C(OC1)C(=NC=N2)OC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=CC=1C)C YRGCZVSKUACKQH-UHFFFAOYSA-N 0.000 claims 1
• AIYUONYKSBONEB-UHFFFAOYSA-N 3-chloro-4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC=1C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=CC=1OC1=NC=NC2=C1OCCN2 AIYUONYKSBONEB-UHFFFAOYSA-N 0.000 claims 1
• USBQXDXRMMLQGL-UHFFFAOYSA-N 3-chloro-4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=CC=1OC1=NC=NC2=C1OCCN2 USBQXDXRMMLQGL-UHFFFAOYSA-N 0.000 claims 1
• JCDIIRZTEHVLQB-UHFFFAOYSA-N 3-chloro-5-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC=1C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C(C=1)OC1=NC=NC2=C1OCCN2 JCDIIRZTEHVLQB-UHFFFAOYSA-N 0.000 claims 1
• LSARLBVTXSPBRR-UHFFFAOYSA-N 4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC1=CC=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=C1 LSARLBVTXSPBRR-UHFFFAOYSA-N 0.000 claims 1
• BIPDTHKUUITCBZ-UHFFFAOYSA-N 4-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound N1=CN=C(C=2OCCNC=21)OC1=CC=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C1 BIPDTHKUUITCBZ-UHFFFAOYSA-N 0.000 claims 1
• APQVWBGCOGGLMK-UHFFFAOYSA-N 4-chloro-3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=C1)OC1=CC=NC2=C1OCCN2 APQVWBGCOGGLMK-UHFFFAOYSA-N 0.000 claims 1
• UAJYMMCSYISWAN-UHFFFAOYSA-N 4-chloro-3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-8-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C1)OC1=CC=NC2=C1OCCN2 UAJYMMCSYISWAN-UHFFFAOYSA-N 0.000 claims 1
• FSNYHGZGZNKJET-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-ylamino)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C1)NC1=NC=NC2=C1OCCN2 FSNYHGZGZNKJET-UHFFFAOYSA-N 0.000 claims 1
• GBYVFBZEMKEBGM-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[2-(1-methylpiperidin-4-yl)oxy-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=C(C=CC(=C2)C(F)(F)F)OC2CCN(CC2)C)C=C1)OC1=NC=NC2=C1OCCN2 GBYVFBZEMKEBGM-UHFFFAOYSA-N 0.000 claims 1
• MQCPYFJWOJSOTB-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[2-fluoro-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=C(C(=CC=C2)C(F)(F)F)F)C=C1)OC1=NC=NC2=C1OCCN2 MQCPYFJWOJSOTB-UHFFFAOYSA-N 0.000 claims 1
• HPIOIHLWLODWEA-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[2-fluoro-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=C(C=CC(=C2)C(F)(F)F)F)C=C1)OC1=NC=NC2=C1OCCN2 HPIOIHLWLODWEA-UHFFFAOYSA-N 0.000 claims 1
• FAIYZLUUURWMLV-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(1,1-dioxo-1,4-thiazinan-4-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCS(CC2)(=O)=O)C=C1)OC1=NC=NC2=C1OCCN2 FAIYZLUUURWMLV-UHFFFAOYSA-N 0.000 claims 1
• UHQMHSDWIJPGES-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(1-methylazetidin-3-yl)oxy-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)OC2CN(C2)C)C=C1)OC1=NC=NC2=C1OCCN2 UHQMHSDWIJPGES-UHFFFAOYSA-N 0.000 claims 1
• OMDVUAPCZODZPV-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(1-methylpiperidin-4-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C2CCN(CC2)C)C=C1)OC1=NC=NC2=C1OCCN2 OMDVUAPCZODZPV-UHFFFAOYSA-N 0.000 claims 1
• HWKJUWZJMCNZCO-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(1-methylpyrazol-4-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C=2C=NN(C=2)C)C=C1)OC1=NC=NC2=C1OCCN2 HWKJUWZJMCNZCO-UHFFFAOYSA-N 0.000 claims 1
• RFJUZGOBEYEVBC-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(1H-pyrazol-4-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound N1N=CC(=C1)C=1C=C(C=C(C=1)C(F)(F)F)NC(C1=CC(=C(C=C1)Cl)OC1=NC=NC2=C1OCCN2)=O RFJUZGOBEYEVBC-UHFFFAOYSA-N 0.000 claims 1
• ZFEUCSBJAAWETN-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(3-hydroxybut-1-ynyl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C#CC(C)O)C=C1)OC1=NC=NC2=C1OCCN2 ZFEUCSBJAAWETN-UHFFFAOYSA-N 0.000 claims 1
• YXYAJINKPFCWNJ-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(3-oxomorpholin-4-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C(COCC2)=O)C=C1)OC1=NC=NC2=C1OCCN2 YXYAJINKPFCWNJ-UHFFFAOYSA-N 0.000 claims 1
• ATIRYRBIUGWYQM-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(4-ethylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)CC)C=C1)OC1=NC=NC2=C1OCCN2 ATIRYRBIUGWYQM-UHFFFAOYSA-N 0.000 claims 1
• ICUWQYYGHYFXCW-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(4-fluoropiperidin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCC(CC2)F)C=C1)OC1=NC=NC2=C1OCCN2 ICUWQYYGHYFXCW-UHFFFAOYSA-N 0.000 claims 1
• AJEUWBBZRVVMDN-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(4-methyl-1,4-diazepan-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CCC2)C)C=C1)OC1=NC=NC2=C1OCCN2 AJEUWBBZRVVMDN-UHFFFAOYSA-N 0.000 claims 1
• QKPTVFSDYXTZLI-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C=NC(=C2)C)C=C1)OC1=NC=NC2=C1OCCN2 QKPTVFSDYXTZLI-UHFFFAOYSA-N 0.000 claims 1
• YVAOPPGWYSALSA-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=C1)OC1=NC=NC2=C1OCCN2 YVAOPPGWYSALSA-UHFFFAOYSA-N 0.000 claims 1
• TXTMPBZWRKUCLD-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(4-methylpiperidin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCC(CC2)C)C=C1)OC1=NC=NC2=C1OCCN2 TXTMPBZWRKUCLD-UHFFFAOYSA-N 0.000 claims 1
• JZRMPTJWXPKYES-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(4-propan-2-ylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C(C)C)C=C1)OC1=NC=NC2=C1OCCN2 JZRMPTJWXPKYES-UHFFFAOYSA-N 0.000 claims 1
• MCBQZMSEQDGXHO-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(4-propylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)CCC)C=C1)OC1=NC=NC2=C1OCCN2 MCBQZMSEQDGXHO-UHFFFAOYSA-N 0.000 claims 1
• JAAPKPRDCFCEKO-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(prop-2-enoylamino)-5-(trifluoromethyl)phenyl]benzamide Chemical compound C(C=C)(=O)NC=1C=C(C=C(C=1)C(F)(F)F)NC(C1=CC(=C(C=C1)Cl)OC1=NC=NC2=C1OCCN2)=O JAAPKPRDCFCEKO-UHFFFAOYSA-N 0.000 claims 1
• MDVXQXZPKARDMY-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(propanoylamino)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)NC(CC)=O)C=C1)OC1=NC=NC2=C1OCCN2 MDVXQXZPKARDMY-UHFFFAOYSA-N 0.000 claims 1
• REUNAGMSWPLATN-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC=C2)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 REUNAGMSWPLATN-UHFFFAOYSA-N 0.000 claims 1
• DMJSXYDBWJZPNP-CQSZACIVSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(2R)-2-methylpiperazin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2[C@@H](CNCC2)C)C=C1)OC1=NC=NC2=C1OCCN2 DMJSXYDBWJZPNP-CQSZACIVSA-N 0.000 claims 1
• UKBAWGLUJZLBBF-GASCZTMLSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C[C@H](O[C@H](C2)C)C)C=C1)OC1=NC=NC2=C1OCCN2 UKBAWGLUJZLBBF-GASCZTMLSA-N 0.000 claims 1
• QUKXDTOZHKXHEW-HNNXBMFYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(2S)-2,4-dimethylpiperazin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2[C@H](CN(CC2)C)C)C=C1)OC1=NC=NC2=C1OCCN2 QUKXDTOZHKXHEW-HNNXBMFYSA-N 0.000 claims 1
• DMJSXYDBWJZPNP-AWEZNQCLSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(2S)-2-methylpiperazin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2[C@H](CNCC2)C)C=C1)OC1=NC=NC2=C1OCCN2 DMJSXYDBWJZPNP-AWEZNQCLSA-N 0.000 claims 1
• XBBYMOJTVZKWAD-GOSISDBHSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C[C@@H](CC2)N(C)C)C=C1)OC1=NC=NC2=C1OCCN2 XBBYMOJTVZKWAD-GOSISDBHSA-N 0.000 claims 1
• WHNOAOOFTKMCKM-OAHLLOKOSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(3R)-3-fluoropyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C[C@@H](CC2)F)C=C1)OC1=NC=NC2=C1OCCN2 WHNOAOOFTKMCKM-OAHLLOKOSA-N 0.000 claims 1
• DNESKSIWSSZKBU-QGZVFWFLSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(3R)-3-hydroxypyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C[C@@H](CC2)O)C=C1)OC1=NC=NC2=C1OCCN2 DNESKSIWSSZKBU-QGZVFWFLSA-N 0.000 claims 1
• JSOJSXZWIHUZIO-PFEQFJNWSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(3R)-3-methylpiperazin-1-yl]-5-(trifluoromethyl)phenyl]benzamide hydrochloride Chemical compound Cl.C[C@@H]1CN(CCN1)c1cc(NC(=O)c2ccc(Cl)c(Oc3ncnc4NCCOc34)c2)cc(c1)C(F)(F)F JSOJSXZWIHUZIO-PFEQFJNWSA-N 0.000 claims 1
• OUHMTEKEKORDKN-HNNXBMFYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(3S)-3,4-dimethylpiperazin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C[C@@H](N(CC2)C)C)C=C1)OC1=NC=NC2=C1OCCN2 OUHMTEKEKORDKN-HNNXBMFYSA-N 0.000 claims 1
• XBBYMOJTVZKWAD-SFHVURJKSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C[C@H](CC2)N(C)C)C=C1)OC1=NC=NC2=C1OCCN2 XBBYMOJTVZKWAD-SFHVURJKSA-N 0.000 claims 1
• WHNOAOOFTKMCKM-HNNXBMFYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(3S)-3-fluoropyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C[C@H](CC2)F)C=C1)OC1=NC=NC2=C1OCCN2 WHNOAOOFTKMCKM-HNNXBMFYSA-N 0.000 claims 1
• DNESKSIWSSZKBU-KRWDZBQOSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(3S)-3-hydroxypyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C[C@H](CC2)O)C=C1)OC1=NC=NC2=C1OCCN2 DNESKSIWSSZKBU-KRWDZBQOSA-N 0.000 claims 1
• JSOJSXZWIHUZIO-UQKRIMTDSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(3S)-3-methylpiperazin-1-yl]-5-(trifluoromethyl)phenyl]benzamide hydrochloride Chemical compound Cl.C[C@H]1CN(CCN1)c1cc(NC(=O)c2ccc(Cl)c(Oc3ncnc4NCCOc34)c2)cc(c1)C(F)(F)F JSOJSXZWIHUZIO-UQKRIMTDSA-N 0.000 claims 1
• MNPQCAORICRYMX-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(4-ethylpiperazin-1-yl)methyl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)CN2CCN(CC2)CC)C=C1)OC1=NC=NC2=C1OCCN2 MNPQCAORICRYMX-UHFFFAOYSA-N 0.000 claims 1
• JZRRQVSSRUCAEI-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(dimethylamino)methyl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)CN(C)C)C=C1)OC1=NC=NC2=C1OCCN2 JZRRQVSSRUCAEI-UHFFFAOYSA-N 0.000 claims 1
• LIRFQYJNDVWWOA-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[(propan-2-ylamino)methyl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)CNC(C)C)C=C1)OC1=NC=NC2=C1OCCN2 LIRFQYJNDVWWOA-UHFFFAOYSA-N 0.000 claims 1
• WUCDZEFCMAPKAJ-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[2-(dimethylamino)ethyl-methylamino]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N(C)CCN(C)C)C=C1)OC1=NC=NC2=C1OCCN2 WUCDZEFCMAPKAJ-UHFFFAOYSA-N 0.000 claims 1
• UZDJNBVCJFAWQE-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[3-(dimethylamino)azetidin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CC(C2)N(C)C)C=C1)OC1=NC=NC2=C1OCCN2 UZDJNBVCJFAWQE-UHFFFAOYSA-N 0.000 claims 1
• QADYYHXGIGBGJJ-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[4-(dimethylamino)piperidin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCC(CC2)N(C)C)C=C1)OC1=NC=NC2=C1OCCN2 QADYYHXGIGBGJJ-UHFFFAOYSA-N 0.000 claims 1
• WXLVPHOQCZKNRV-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[4-(oxetan-3-yl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C2COC2)C=C1)OC1=NC=NC2=C1OCCN2 WXLVPHOQCZKNRV-UHFFFAOYSA-N 0.000 claims 1
• HROAUNYIIPBXJU-FQEVSTJZSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[[(3S)-3-(dimethylamino)pyrrolidin-1-yl]methyl]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)CN2C[C@H](CC2)N(C)C)C=C1)OC1=NC=NC2=C1OCCN2 HROAUNYIIPBXJU-FQEVSTJZSA-N 0.000 claims 1
• RCDILPCTLLECGB-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-[[2-(dimethylamino)acetyl]amino]-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)NC(CN(C)C)=O)C=C1)OC1=NC=NC2=C1OCCN2 RCDILPCTLLECGB-UHFFFAOYSA-N 0.000 claims 1
• NJASNFKVUYXULM-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-fluoro-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)F)C=C1)OC1=NC=NC2=C1OCCN2 NJASNFKVUYXULM-UHFFFAOYSA-N 0.000 claims 1
• FMFXKKXRGUHBEV-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[3-morpholin-4-yl-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCOCC2)C=C1)OC1=NC=NC2=C1OCCN2 FMFXKKXRGUHBEV-UHFFFAOYSA-N 0.000 claims 1
• JCIDTLQMRLRRBZ-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-(1-ethylpiperidin-4-yl)oxy-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)OC2CCN(CC2)CC)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 JCIDTLQMRLRRBZ-UHFFFAOYSA-N 0.000 claims 1
• LTZBVZZLBZDQFE-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-(4-ethylpiperazine-1-carbonyl)-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)C(=O)N2CCN(CC2)CC)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 LTZBVZZLBZDQFE-UHFFFAOYSA-N 0.000 claims 1
• BZTMOEQAOXGGKF-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-(4-methylpiperazin-1-yl)-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)N2CCN(CC2)C)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 BZTMOEQAOXGGKF-UHFFFAOYSA-N 0.000 claims 1
• RCJINMHSCHVPIX-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-(morpholin-4-ylmethyl)-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCOCC2)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 RCJINMHSCHVPIX-UHFFFAOYSA-N 0.000 claims 1
• PSLLMSGLAFZHLN-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-(piperazin-1-ylmethyl)-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCNCC2)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 PSLLMSGLAFZHLN-UHFFFAOYSA-N 0.000 claims 1
• URZAXZVUXBZBEU-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC=C(C=C2)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 URZAXZVUXBZBEU-UHFFFAOYSA-N 0.000 claims 1
• YGTTUUUXJWQEOG-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-2-methylbenzamide Chemical compound ClC1=C(C(=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C1)C)OC1=NC=NC2=C1OCCN2 YGTTUUUXJWQEOG-UHFFFAOYSA-N 0.000 claims 1
• RJLSJLNTTGPIAJ-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 RJLSJLNTTGPIAJ-UHFFFAOYSA-N 0.000 claims 1
• HXJIOMIMUCXUHI-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-methylphenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C)C=C1)OC1=NC=NC2=C1OCCN2 HXJIOMIMUCXUHI-UHFFFAOYSA-N 0.000 claims 1
• OOJAOHJQCWHXAR-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-methylsulfonylphenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)S(=O)(=O)C)C=C1)OC1=NC=NC2=C1OCCN2 OOJAOHJQCWHXAR-UHFFFAOYSA-N 0.000 claims 1
• ZXYVKLLKHMKMPI-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC=C(C=C2)CN2CCN(CC2)CC)C=C1)OC1=NC=NC2=C1OCCN2 ZXYVKLLKHMKMPI-UHFFFAOYSA-N 0.000 claims 1
• OJBBXAKUNLQKNT-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)C)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 OJBBXAKUNLQKNT-UHFFFAOYSA-N 0.000 claims 1
• WDGYMSYEVAFPSB-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-methylpiperidin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCC(CC2)C)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 WDGYMSYEVAFPSB-UHFFFAOYSA-N 0.000 claims 1
• BFRUHANPYRZCOY-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-propan-2-ylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)C(C)C)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 BFRUHANPYRZCOY-UHFFFAOYSA-N 0.000 claims 1
• OSDUMUOIJAWOIQ-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[(4-propylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CCC)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 OSDUMUOIJAWOIQ-UHFFFAOYSA-N 0.000 claims 1
• LHTSPBSKNKIJDY-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[2-(dimethylamino)ethoxy]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)OCCN(C)C)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 LHTSPBSKNKIJDY-UHFFFAOYSA-N 0.000 claims 1
• JAYMEGJLSFOFPQ-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[2-(dimethylamino)ethylcarbamoyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C(=O)NCCN(C)C)C=C2)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 JAYMEGJLSFOFPQ-UHFFFAOYSA-N 0.000 claims 1
• WBMFWVVBPBPCCO-LJQANCHMSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[[(3R)-3-(dimethylamino)pyrrolidin-1-yl]methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2C[C@@H](CC2)N(C)C)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 WBMFWVVBPBPCCO-LJQANCHMSA-N 0.000 claims 1
• STOKFSGOPWNIDD-GOSISDBHSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[[(3R)-3-(methylamino)pyrrolidin-1-yl]methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2C[C@@H](CC2)NC)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 STOKFSGOPWNIDD-GOSISDBHSA-N 0.000 claims 1
• WBMFWVVBPBPCCO-IBGZPJMESA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[[(3S)-3-(dimethylamino)pyrrolidin-1-yl]methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2C[C@H](CC2)N(C)C)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 WBMFWVVBPBPCCO-IBGZPJMESA-N 0.000 claims 1
• STOKFSGOPWNIDD-SFHVURJKSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[[(3S)-3-(methylamino)pyrrolidin-1-yl]methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2C[C@H](CC2)NC)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 STOKFSGOPWNIDD-SFHVURJKSA-N 0.000 claims 1
• WBMFWVVBPBPCCO-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-[[3-(dimethylamino)pyrrolidin-1-yl]methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CC(CC2)N(C)C)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 WBMFWVVBPBPCCO-UHFFFAOYSA-N 0.000 claims 1
• FYAXGAIBMXRRCN-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-morpholin-4-yl-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)N2CCOCC2)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 FYAXGAIBMXRRCN-UHFFFAOYSA-N 0.000 claims 1
• IVZVJHSKQODKDU-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[4-piperazin-1-yl-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)N2CCNCC2)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 IVZVJHSKQODKDU-UHFFFAOYSA-N 0.000 claims 1
• AUJHHJJJIJAKBX-UHFFFAOYSA-N 4-chloro-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)-N-[6-methyl-5-(trifluoromethyl)pyridin-3-yl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC=2C=NC(=C(C=2)C(F)(F)F)C)C=C1)OC1=NC=NC2=C1OCCN2 AUJHHJJJIJAKBX-UHFFFAOYSA-N 0.000 claims 1
• TTYNFJCBLKZKDQ-UHFFFAOYSA-N 4-chloro-3-[(2-chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl)oxy]-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C1)OC1=NC(=NC2=C1OCCN2)Cl TTYNFJCBLKZKDQ-UHFFFAOYSA-N 0.000 claims 1
• DKDIQTWXTAHUJT-UHFFFAOYSA-N 4-chloro-3-[(7,7-dimethyl-6,8-dihydropyrimido[5,4-b][1,4]oxazin-4-yl)oxy]-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=C1)OC1=NC=NC2=C1OCC(N2)(C)C DKDIQTWXTAHUJT-UHFFFAOYSA-N 0.000 claims 1
• OWMHTPRUOAVCIS-UHFFFAOYSA-N 4-chloro-3-[(7,7-dimethyl-6,8-dihydropyrimido[5,4-b][1,4]oxazin-4-yl)oxy]-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCC(N2)(C)C OWMHTPRUOAVCIS-UHFFFAOYSA-N 0.000 claims 1
• MQBSRJFRFQDQQD-UHFFFAOYSA-N 4-chloro-3-[(8-methyl-6,7-dihydropyrimido[5,4-b][1,4]oxazin-4-yl)oxy]-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=C1)OC1=NC=NC2=C1OCCN2C MQBSRJFRFQDQQD-UHFFFAOYSA-N 0.000 claims 1
• HJJXDMTZWAYPRZ-OAHLLOKOSA-N 4-chloro-3-[[(6R)-6-methyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=C1)OC1=NC=NC2=C1O[C@@H](CN2)C HJJXDMTZWAYPRZ-OAHLLOKOSA-N 0.000 claims 1
• HJJXDMTZWAYPRZ-HNNXBMFYSA-N 4-chloro-3-[[(6S)-6-methyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=C1)OC1=NC=NC2=C1O[C@H](CN2)C HJJXDMTZWAYPRZ-HNNXBMFYSA-N 0.000 claims 1
• APMXICVETZEJGI-GOSISDBHSA-N 4-chloro-3-[[(7R)-7-(morpholin-4-ylmethyl)-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]-N-[3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC=C2)C(F)(F)F)C=C1)OC1=NC=NC2=C1OC[C@H](N2)CN1CCOCC1 APMXICVETZEJGI-GOSISDBHSA-N 0.000 claims 1
• QXIRIQBYDFTLFW-JOCHJYFZSA-N 4-chloro-3-[[(7R)-7-[(dimethylamino)methyl]-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C1)OC1=NC=NC2=C1OC[C@H](N2)CN(C)C QXIRIQBYDFTLFW-JOCHJYFZSA-N 0.000 claims 1
• MOZRBQJHEBMJPD-HXUWFJFHSA-N 4-chloro-3-[[(7R)-7-ethyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C1)OC1=NC=NC2=C1OC[C@H](N2)CC MOZRBQJHEBMJPD-HXUWFJFHSA-N 0.000 claims 1
• VOOCDSOHUPLQOE-OAHLLOKOSA-N 4-chloro-3-[[(7R)-7-methyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]-N-[2-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=C(C=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=C1)OC1=NC=NC2=C1OC[C@H](N2)C VOOCDSOHUPLQOE-OAHLLOKOSA-N 0.000 claims 1
• FJYHCFGNLODCAL-OAHLLOKOSA-N 4-chloro-3-[[(7R)-7-methyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=C1)OC1=NC=NC2=C1OC[C@H](N2)C FJYHCFGNLODCAL-OAHLLOKOSA-N 0.000 claims 1
• YXYQSTYHQBWILL-MRXNPFEDSA-N 4-chloro-3-[[(7R)-7-methyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]-N-[3-(4-methylpiperazin-1-yl)phenyl]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC=C2)N2CCN(CC2)C)C=C1)OC1=NC=NC2=C1OC[C@H](N2)C YXYQSTYHQBWILL-MRXNPFEDSA-N 0.000 claims 1
• ZTKVDSGHPGUTTQ-UHFFFAOYSA-N 4-chloro-N-[3-(1,4-diazepan-1-yl)-5-(trifluoromethyl)phenyl]-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)benzamide hydrochloride Chemical compound Cl.FC(F)(F)c1cc(NC(=O)c2ccc(Cl)c(Oc3ncnc4NCCOc34)c2)cc(c1)N1CCCNCC1 ZTKVDSGHPGUTTQ-UHFFFAOYSA-N 0.000 claims 1
• MZWLTWVPAUCAAU-UHFFFAOYSA-N 4-chloro-N-[3-(1-cyanocyclopropyl)phenyl]-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC=C2)C2(CC2)C#N)C=C1)OC1=NC=NC2=C1OCCN2 MZWLTWVPAUCAAU-UHFFFAOYSA-N 0.000 claims 1
• VQAKOJIINIDPDT-UHFFFAOYSA-N 4-chloro-N-[3-(2-cyanopropan-2-yl)phenyl]-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC=C2)C(C)(C)C#N)C=C1)OC1=NC=NC2=C1OCCN2 VQAKOJIINIDPDT-UHFFFAOYSA-N 0.000 claims 1
• VIKDAZDOSRHAGP-UHFFFAOYSA-N 4-chloro-N-[3-(4,4-difluoropiperidin-1-yl)-5-(trifluoromethyl)phenyl]-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCC(CC2)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 VIKDAZDOSRHAGP-UHFFFAOYSA-N 0.000 claims 1
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• RNKFWXYHLREHNI-QFIPXVFZSA-N 4-chloro-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]-3-[[(7R)-7-propan-2-yl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=C1)OC1=NC=NC2=C1OC[C@H](N2)C(C)C RNKFWXYHLREHNI-QFIPXVFZSA-N 0.000 claims 1
• RNKFWXYHLREHNI-JOCHJYFZSA-N 4-chloro-N-[3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]-3-[[(7S)-7-propan-2-yl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2CCN(CC2)C)C=C1)OC1=NC=NC2=C1OC[C@@H](N2)C(C)C RNKFWXYHLREHNI-JOCHJYFZSA-N 0.000 claims 1
• ROCATEASYLSFSQ-AKXYIILFSA-N 4-chloro-N-[3-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-5-(trifluoromethyl)phenyl]-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)benzamide hydrochloride Chemical compound Cl.FC(F)(F)c1cc(NC(=O)c2ccc(Cl)c(Oc3ncnc4NCCOc34)c2)cc(c1)N1C[C@@H]2C[C@H]1CN2 ROCATEASYLSFSQ-AKXYIILFSA-N 0.000 claims 1
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• YDHVQITWUJHSFC-UHFFFAOYSA-N 4-chloro-N-[3-cyano-5-(trifluoromethyl)phenyl]-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C#N)C=C1)OC1=NC=NC2=C1OCCN2 YDHVQITWUJHSFC-UHFFFAOYSA-N 0.000 claims 1
• MDGCEBXWGCIZPO-UHFFFAOYSA-N 4-chloro-N-[4-(2-cyanopropan-2-yl)-3-(trifluoromethyl)phenyl]-3-(7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yloxy)benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)C(C)(C)C#N)C(F)(F)F)C=C1)OC1=NC=NC2=C1OCCN2 MDGCEBXWGCIZPO-UHFFFAOYSA-N 0.000 claims 1
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• KQTKUHCLDMJDGS-UHFFFAOYSA-N 4-chloro-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-3-[(5-oxo-7,8-dihydro-6H-pyrido[2,3-d]pyrimidin-4-yl)oxy]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C1)OC=1C2=C(N=CN=1)NCCC2=O KQTKUHCLDMJDGS-UHFFFAOYSA-N 0.000 claims 1
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• ZOJXULQJPAPAES-KRWDZBQOSA-N 4-chloro-N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-3-[[(7S)-7-methyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-yl]oxy]benzamide Chemical compound ClC1=C(C=C(C(=O)NC2=CC(=C(C=C2)CN2CCN(CC2)CC)C(F)(F)F)C=C1)OC1=NC=NC2=C1OC[C@@H](N2)C ZOJXULQJPAPAES-KRWDZBQOSA-N 0.000 claims 1
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