JP2013529630A5

JP2013529630A5 -

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Publication number: JP2013529630A5
Authority: JP; Japan
Prior art keywords: phenyl; thieno; pyrimidin; acrylamide; yloxy
Prior art date: 2011-06-20
Legal status : Granted

Application number

JP2013516501A

Other languages

English (en)

Japanese (ja)

Other versions

JP2013529630A (ja

JP5834347B2 (ja

Filing date

2011-06-20

Publication date

2014-07-03

2011-06-20 Application filed filed Critical

2011-06-20 Priority claimed from PCT/KR2011/004482 external-priority patent/WO2011162515A2/en

2013-07-22 Publication of JP2013529630A publication Critical patent/JP2013529630A/ja

2014-07-03 Publication of JP2013529630A5 publication Critical patent/JP2013529630A5/ja

2015-12-16 Application granted granted Critical

2015-12-16 Publication of JP5834347B2 publication Critical patent/JP5834347B2/ja

Status Active legal-status Critical Current

2031-06-20 Anticipated expiration legal-status Critical

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125000000217 alkyl group Chemical group 0.000 claims 38
-1 heterocyclic carboxamides Chemical group 0.000 claims 19
206010028980 Neoplasm Diseases 0.000 claims 13
125000003545 alkoxy group Chemical group 0.000 claims 13
125000000623 heterocyclic group Chemical group 0.000 claims 13
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 8
201000010099 disease Diseases 0.000 claims 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 7
150000001875 compounds Chemical class 0.000 claims 7
230000001404 mediated effect Effects 0.000 claims 7
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 6
208000023275 Autoimmune disease Diseases 0.000 claims 6
201000011510 cancer Diseases 0.000 claims 6
208000027866 inflammatory disease Diseases 0.000 claims 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
125000003282 alkyl amino group Chemical group 0.000 claims 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 4
125000001072 heteroaryl group Chemical group 0.000 claims 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 3
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 3
125000005115 alkyl carbamoyl group Chemical group 0.000 claims 3
125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 3
239000003814 drug Substances 0.000 claims 3
229910052736 halogen Inorganic materials 0.000 claims 3
150000002367 halogens Chemical group 0.000 claims 3
208000032839 leukemia Diseases 0.000 claims 3
239000000203 mixture Substances 0.000 claims 3
125000002950 monocyclic group Chemical group 0.000 claims 3
229910052757 nitrogen Inorganic materials 0.000 claims 3
125000004433 nitrogen atom Chemical group N* 0.000 claims 3
229910052760 oxygen Inorganic materials 0.000 claims 3
150000003839 salts Chemical class 0.000 claims 3
229910052717 sulfur Inorganic materials 0.000 claims 3
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
201000004624 Dermatitis Diseases 0.000 claims 2
102000001301 EGF receptor Human genes 0.000 claims 2
108060006698 EGF receptor Proteins 0.000 claims 2
206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 claims 2
108010019421 Janus Kinase 3 Proteins 0.000 claims 2
208000019693 Lung disease Diseases 0.000 claims 2
201000003793 Myelodysplastic syndrome Diseases 0.000 claims 2
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims 2
102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 claims 2
102100039079 Tyrosine-protein kinase TXK Human genes 0.000 claims 2
208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
239000002246 antineoplastic agent Substances 0.000 claims 2
125000003118 aryl group Chemical group 0.000 claims 2
201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
239000003795 chemical substances by application Substances 0.000 claims 2
230000001684 chronic effect Effects 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 2
239000003112 inhibitor Substances 0.000 claims 2
230000001599 osteoclastic effect Effects 0.000 claims 2
201000008968 osteosarcoma Diseases 0.000 claims 2
125000005499 phosphonyl group Chemical group 0.000 claims 2
239000000126 substance Substances 0.000 claims 2
125000001424 substituent group Chemical group 0.000 claims 2
201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
229940124597 therapeutic agent Drugs 0.000 claims 2
KZIVRCDABPQWEG-VMPITWQZSA-N (e)-4-(dimethylamino)-n-[3-[2-[4-(4-methylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]sulfanylphenyl]but-2-enamide Chemical compound CN(C)C\C=C\C(=O)NC1=CC=CC(SC=2C=3SC=CC=3N=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=2)=C1 KZIVRCDABPQWEG-VMPITWQZSA-N 0.000 claims 1
ZYRHKIILJWFSNA-UHFFFAOYSA-N 1-[4-[[4-[3-(prop-2-enoylamino)phenoxy]thieno[3,2-d]pyrimidin-2-yl]amino]phenyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ZYRHKIILJWFSNA-UHFFFAOYSA-N 0.000 claims 1
CBBLWQNEHXIURV-UHFFFAOYSA-N 2-chloro-n,n-dimethyl-4-[[4-[3-(prop-2-enoylamino)phenoxy]thieno[3,2-d]pyrimidin-2-yl]amino]benzamide Chemical compound C1=C(Cl)C(C(=O)N(C)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 CBBLWQNEHXIURV-UHFFFAOYSA-N 0.000 claims 1
GRGFCLNXIJALEX-UHFFFAOYSA-N 3-methoxy-4-[[4-[3-(prop-2-enoylamino)phenoxy]thieno[3,2-d]pyrimidin-2-yl]amino]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound COC1=CC(C(=O)NCCN2CCCC2)=CC=C1NC(N=C1C=CSC1=1)=NC=1OC1=CC=CC(NC(=O)C=C)=C1 GRGFCLNXIJALEX-UHFFFAOYSA-N 0.000 claims 1
KNWWGBNAUNTSRV-UHFFFAOYSA-N 4-methylpiperazine-1-carboxylic acid Chemical compound CN1CCN(C(O)=O)CC1 KNWWGBNAUNTSRV-UHFFFAOYSA-N 0.000 claims 1
208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 1
206010052613 Allergic bronchitis Diseases 0.000 claims 1
206010049153 Allergic sinusitis Diseases 0.000 claims 1
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208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
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XOJMFJJADYCRTG-UHFFFAOYSA-N C(C)N(CC)CN(C1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N)C2=C(C=CC=C2)OC Chemical compound C(C)N(CC)CN(C1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N)C2=C(C=CC=C2)OC XOJMFJJADYCRTG-UHFFFAOYSA-N 0.000 claims 1
RJWLRBHESYQNRM-UHFFFAOYSA-N C(C)N(CC)CN(C1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N)C2=CC=CC=C2 Chemical compound C(C)N(CC)CN(C1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N)C2=CC=CC=C2 RJWLRBHESYQNRM-UHFFFAOYSA-N 0.000 claims 1
GLWMKEDXXMEHIP-UHFFFAOYSA-N CN(C)CN(C1(C2=C(N=CN1)C=CS2)NC2=C(C=CC=C2)C=CC(=O)N)C2=CC=CC=C2 Chemical compound CN(C)CN(C1(C2=C(N=CN1)C=CS2)NC2=C(C=CC=C2)C=CC(=O)N)C2=CC=CC=C2 GLWMKEDXXMEHIP-UHFFFAOYSA-N 0.000 claims 1
QVNUCNKDLFSBQB-UHFFFAOYSA-N CN(C)CN(C1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N)C2=C(C=CC=C2)C Chemical compound CN(C)CN(C1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N)C2=C(C=CC=C2)C QVNUCNKDLFSBQB-UHFFFAOYSA-N 0.000 claims 1
QDBJCQTVDONXDS-UHFFFAOYSA-N CN(C)CN(C1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N)C2=CC=CC=C2 Chemical compound CN(C)CN(C1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N)C2=CC=CC=C2 QDBJCQTVDONXDS-UHFFFAOYSA-N 0.000 claims 1
GLBPDZLLAFWMRK-UHFFFAOYSA-N COC1(C(C=CC=C1)NC=1N=C(C2=C(N1)C=CS2)OC=2C=C(C=CC2)NC(C=C)=O)C2CCN(CC2)C Chemical compound COC1(C(C=CC=C1)NC=1N=C(C2=C(N1)C=CS2)OC=2C=C(C=CC2)NC(C=C)=O)C2CCN(CC2)C GLBPDZLLAFWMRK-UHFFFAOYSA-N 0.000 claims 1
STPFZICEWAIKAJ-UHFFFAOYSA-N COC1(C(C=CC=C1)NC=1N=C(C2=C(N1)C=CS2)OC=2C=C(C=CC2)NC(C=C)=O)C2CN(CCC2)C Chemical compound COC1(C(C=CC=C1)NC=1N=C(C2=C(N1)C=CS2)OC=2C=C(C=CC2)NC(C=C)=O)C2CN(CCC2)C STPFZICEWAIKAJ-UHFFFAOYSA-N 0.000 claims 1
BYVVAGCTASHFNO-UHFFFAOYSA-N COC1=C(C=CC(=C1)CN1CCCCC1)NC=1N=C(C2=C(N1)C=CS2)NC2=C(C=CC=C2)C=CC(=O)N Chemical compound COC1=C(C=CC(=C1)CN1CCCCC1)NC=1N=C(C2=C(N1)C=CS2)NC2=C(C=CC=C2)C=CC(=O)N BYVVAGCTASHFNO-UHFFFAOYSA-N 0.000 claims 1
ZYTXAKONOOQQMO-UHFFFAOYSA-N CS(=O)(=O)CN(C1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N)C2=CC=CC=C2 Chemical compound CS(=O)(=O)CN(C1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N)C2=CC=CC=C2 ZYTXAKONOOQQMO-UHFFFAOYSA-N 0.000 claims 1
241000222122 Candida albicans Species 0.000 claims 1
206010007134 Candida infections Diseases 0.000 claims 1
206010007559 Cardiac failure congestive Diseases 0.000 claims 1
208000024172 Cardiovascular disease Diseases 0.000 claims 1
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
206010009900 Colitis ulcerative Diseases 0.000 claims 1
208000011231 Crohn disease Diseases 0.000 claims 1
206010012438 Dermatitis atopic Diseases 0.000 claims 1
208000002249 Diabetes Complications Diseases 0.000 claims 1
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OYCYLUXXWQMTDL-UHFFFAOYSA-N FC1(C(C=CC(=C1)N1CCN(CC1)C)NN1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)OC Chemical compound FC1(C(C=CC(=C1)N1CCN(CC1)C)NN1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)OC OYCYLUXXWQMTDL-UHFFFAOYSA-N 0.000 claims 1
JMNVJPUZOXTLEE-UHFFFAOYSA-N FC1(CC=C(C=C1)NN1CN=C2C(=C1NC1=C(C=CC=C1)C=CC(=O)N)SC=C2)N2CCN(CC2)C Chemical compound FC1(CC=C(C=C1)NN1CN=C2C(=C1NC1=C(C=CC=C1)C=CC(=O)N)SC=C2)N2CCN(CC2)C JMNVJPUZOXTLEE-UHFFFAOYSA-N 0.000 claims 1
QKCIGNIAWRHBGH-UHFFFAOYSA-N FC1(CC=C(C=C1)NN1CN=C2C(=C1NC1=C(C=CC=C1)C=CC(=O)N)SC=C2)NC2CCN(CC2)C Chemical compound FC1(CC=C(C=C1)NN1CN=C2C(=C1NC1=C(C=CC=C1)C=CC(=O)N)SC=C2)NC2CCN(CC2)C QKCIGNIAWRHBGH-UHFFFAOYSA-N 0.000 claims 1
QWZLDGCACBGKJH-UHFFFAOYSA-N FC1(CC=C(C=C1)NN1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)CN2CCN(CC2)C Chemical compound FC1(CC=C(C=C1)NN1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)CN2CCN(CC2)C QWZLDGCACBGKJH-UHFFFAOYSA-N 0.000 claims 1
PKNNTBWDXLFIFU-UHFFFAOYSA-N FC1(CC=C(C=C1)NN1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)OC2CCN(CC2)C Chemical compound FC1(CC=C(C=C1)NN1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)OC2CCN(CC2)C PKNNTBWDXLFIFU-UHFFFAOYSA-N 0.000 claims 1
QFKBQPOIDWAPHD-UHFFFAOYSA-N FC1(CC=C(C=C1)NN1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)OCCN2CCOCC2 Chemical compound FC1(CC=C(C=C1)NN1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)OCCN2CCOCC2 QFKBQPOIDWAPHD-UHFFFAOYSA-N 0.000 claims 1
IQIBBTDLLBDJPC-UHFFFAOYSA-N FC=1C=C(C=CC1N1CCOCC1)NN1CN=C2C(=C1SC1=C(C=CC=C1)C=CC(=O)N)SC=C2 Chemical compound FC=1C=C(C=CC1N1CCOCC1)NN1CN=C2C(=C1SC1=C(C=CC=C1)C=CC(=O)N)SC=C2 IQIBBTDLLBDJPC-UHFFFAOYSA-N 0.000 claims 1
LPYVYAWBJZWXIB-UHFFFAOYSA-N FN(N1CN=C2C(=C1NC1=C(C=CC=C1)C=CC(=O)N)SC=C2)C2=CC=C(C=C2)C2CCN(CC2)C Chemical compound FN(N1CN=C2C(=C1NC1=C(C=CC=C1)C=CC(=O)N)SC=C2)C2=CC=C(C=C2)C2CCN(CC2)C LPYVYAWBJZWXIB-UHFFFAOYSA-N 0.000 claims 1
SGDBDFPYYZYKMS-UHFFFAOYSA-N FN(N1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)C2=CC=C(C=C2)C2CCN(CC2)C Chemical compound FN(N1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)C2=CC=C(C=C2)C2CCN(CC2)C SGDBDFPYYZYKMS-UHFFFAOYSA-N 0.000 claims 1
QYDUJJMQKZROQI-UHFFFAOYSA-N FN(N1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)C2=CC=C(C=C2)C2CN(CCC2)C Chemical compound FN(N1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)C2=CC=C(C=C2)C2CN(CCC2)C QYDUJJMQKZROQI-UHFFFAOYSA-N 0.000 claims 1
KXCNKCFSWFTHLW-UHFFFAOYSA-N FN(N1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)C2=CC=C(C=C2)N2CCC(CC2)N2CCOCC2 Chemical compound FN(N1CN=C2C(=C1OC1=C(C=CC=C1)C=CC(=O)N)SC=C2)C2=CC=C(C=C2)N2CCC(CC2)N2CCOCC2 KXCNKCFSWFTHLW-UHFFFAOYSA-N 0.000 claims 1
DAUFUTYFFYUUDL-UHFFFAOYSA-N FN(N1CN=C2C(=C1SC1=C(C=CC=C1)C=CC(=O)N)SC=C2)C2=CC=C(C=C2)C2CCN(CC2)C Chemical compound FN(N1CN=C2C(=C1SC1=C(C=CC=C1)C=CC(=O)N)SC=C2)C2=CC=C(C=C2)C2CCN(CC2)C DAUFUTYFFYUUDL-UHFFFAOYSA-N 0.000 claims 1
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LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 claims 1
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CJAISBZDOSBBLD-UHFFFAOYSA-N n-[3-[2-[(6-methylsulfinylpyridin-3-yl)amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=NC(S(=O)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 CJAISBZDOSBBLD-UHFFFAOYSA-N 0.000 claims 1
VEWBHTPEKABZKT-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=NC(=CC=3)N3CCOCC3)N=2)=C1 VEWBHTPEKABZKT-UHFFFAOYSA-N 0.000 claims 1
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BKLQMQDSBFDYNM-UHFFFAOYSA-N n-[3-[2-[3-fluoro-4-[(1-methylpiperidin-4-yl)amino]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCC1NC(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 BKLQMQDSBFDYNM-UHFFFAOYSA-N 0.000 claims 1
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CPIZNRFMCCHSKA-UHFFFAOYSA-N n-[3-[2-[3-fluoro-4-[[(1-methylpiperidin-4-yl)amino]methyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCC1NCC(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 CPIZNRFMCCHSKA-UHFFFAOYSA-N 0.000 claims 1
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LFGBSQOCMZPMDP-UHFFFAOYSA-N n-[3-[2-[4-(1-oxo-1,4-thiazinan-4-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(=CC=3)N3CCS(=O)CC3)N=2)=C1 LFGBSQOCMZPMDP-UHFFFAOYSA-N 0.000 claims 1
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USZVADZVLQPDAI-UHFFFAOYSA-N n-[3-[2-[4-(2-hydroxyethyl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=CC(CCO)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 USZVADZVLQPDAI-UHFFFAOYSA-N 0.000 claims 1
RAGHEXWSUJJTGH-UHFFFAOYSA-N n-[3-[2-[4-(2-methoxyethoxy)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=CC(OCCOC)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 RAGHEXWSUJJTGH-UHFFFAOYSA-N 0.000 claims 1
DPGPDMKAPJFOJC-UHFFFAOYSA-N n-[3-[2-[4-(2-methylsulfinylethyl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=CC(CCS(=O)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 DPGPDMKAPJFOJC-UHFFFAOYSA-N 0.000 claims 1
GZQMAEZSOHBECI-UHFFFAOYSA-N n-[3-[2-[4-(2-methylsulfonylethyl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=CC(CCS(=O)(=O)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 GZQMAEZSOHBECI-UHFFFAOYSA-N 0.000 claims 1
LFDFWUWZMDGLIF-UHFFFAOYSA-N n-[3-[2-[4-(2-morpholin-4-ylethoxy)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(OCCN4CCOCC4)=CC=3)N=2)=C1 LFDFWUWZMDGLIF-UHFFFAOYSA-N 0.000 claims 1
TWTDGFCNAHCIDT-UHFFFAOYSA-N n-[3-[2-[4-(2-piperidin-1-ylethyl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(CCN4CCCCC4)=CC=3)N=2)=C1 TWTDGFCNAHCIDT-UHFFFAOYSA-N 0.000 claims 1
UOFSFMMBWORVPO-UHFFFAOYSA-N n-[3-[2-[4-(2-pyrrolidin-1-ylethoxy)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(OCCN4CCCC4)=CC=3)N=2)=C1 UOFSFMMBWORVPO-UHFFFAOYSA-N 0.000 claims 1
OAUYGRWYKKWDGQ-UHFFFAOYSA-N n-[3-[2-[4-(3,4,5-trimethylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1C(C)N(C)C(C)CN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 OAUYGRWYKKWDGQ-UHFFFAOYSA-N 0.000 claims 1
HZCIPBLNCBLOBF-UHFFFAOYSA-N n-[3-[2-[4-(3-imidazol-1-ylpyrrolidin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(=CC=3)N3CC(CC3)N3C=NC=C3)N=2)=C1 HZCIPBLNCBLOBF-UHFFFAOYSA-N 0.000 claims 1
ZQERDWVSWRXVDT-UHFFFAOYSA-N n-[3-[2-[4-(4-acetylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ZQERDWVSWRXVDT-UHFFFAOYSA-N 0.000 claims 1
DRRKWGQACUGSNH-UHFFFAOYSA-N n-[3-[2-[4-(4-cyclohexylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(=CC=3)N3CCN(CC3)C3CCCCC3)N=2)=C1 DRRKWGQACUGSNH-UHFFFAOYSA-N 0.000 claims 1
UNORZHQKORNVTK-UHFFFAOYSA-N n-[3-[2-[4-(4-ethylpiperazin-1-yl)-2-methoxyanilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CC)CCN1C(C=C1OC)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 UNORZHQKORNVTK-UHFFFAOYSA-N 0.000 claims 1
XRBKUNFRIBDEGL-UHFFFAOYSA-N n-[3-[2-[4-(4-ethylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 XRBKUNFRIBDEGL-UHFFFAOYSA-N 0.000 claims 1
WKQOGCVNLPSRTD-UHFFFAOYSA-N n-[3-[2-[4-(4-ethylpiperazin-1-yl)sulfonylanilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CC)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 WKQOGCVNLPSRTD-UHFFFAOYSA-N 0.000 claims 1
ODJAXNBMOLBNFX-UHFFFAOYSA-N n-[3-[2-[4-(4-ethylpiperazine-1-carbonyl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CC)CCN1C(=O)C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ODJAXNBMOLBNFX-UHFFFAOYSA-N 0.000 claims 1
YKSRQHPQMDNONR-UHFFFAOYSA-N n-[3-[2-[4-(4-ethylsulfonylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(S(=O)(=O)CC)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 YKSRQHPQMDNONR-UHFFFAOYSA-N 0.000 claims 1
WMSKYJLZQMVBFB-UHFFFAOYSA-N n-[3-[2-[4-(4-hydroxypiperidin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CC(O)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 WMSKYJLZQMVBFB-UHFFFAOYSA-N 0.000 claims 1
IVNBVRMIPSPLOT-UHFFFAOYSA-N n-[3-[2-[4-(4-hydroxypiperidine-1-carbonyl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CC(O)CCN1C(=O)C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 IVNBVRMIPSPLOT-UHFFFAOYSA-N 0.000 claims 1
VNSUCGBWVHAPDD-UHFFFAOYSA-N n-[3-[2-[4-(4-imidazol-1-ylpiperidin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(=CC=3)N3CCC(CC3)N3C=NC=C3)N=2)=C1 VNSUCGBWVHAPDD-UHFFFAOYSA-N 0.000 claims 1
FDMQDKQUTRLUBU-UHFFFAOYSA-N n-[3-[2-[4-(4-methylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 FDMQDKQUTRLUBU-UHFFFAOYSA-N 0.000 claims 1
SDRMNLCRSANCIY-UHFFFAOYSA-N n-[3-[2-[4-(4-methylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]sulfanylphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(SC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 SDRMNLCRSANCIY-UHFFFAOYSA-N 0.000 claims 1
XXQLPJRHXPVITA-UHFFFAOYSA-N n-[3-[2-[4-(4-methylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]sulfinylphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(S(=O)C=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 XXQLPJRHXPVITA-UHFFFAOYSA-N 0.000 claims 1
JFNQKGPYGZNKAR-UHFFFAOYSA-N n-[3-[2-[4-(4-methylpiperazine-1-carbonyl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 JFNQKGPYGZNKAR-UHFFFAOYSA-N 0.000 claims 1
UWYCPGNPOVYYQE-UHFFFAOYSA-N n-[3-[2-[4-(4-methylsulfonylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(S(=O)(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 UWYCPGNPOVYYQE-UHFFFAOYSA-N 0.000 claims 1
PHCRMGUARHGRRY-UHFFFAOYSA-N n-[3-[2-[4-(4-morpholin-4-ylpiperidin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(=CC=3)N3CCC(CC3)N3CCOCC3)N=2)=C1 PHCRMGUARHGRRY-UHFFFAOYSA-N 0.000 claims 1
ZNYQZWGAZMLJOY-UHFFFAOYSA-N n-[3-[2-[4-(4-piperidin-1-ylpiperidin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(=CC=3)N3CCC(CC3)N3CCCCC3)N=2)=C1 ZNYQZWGAZMLJOY-UHFFFAOYSA-N 0.000 claims 1
HDBDASRZBKUFQH-UHFFFAOYSA-N n-[3-[2-[4-(4-propan-2-ylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 HDBDASRZBKUFQH-UHFFFAOYSA-N 0.000 claims 1
HNUGFTKBEBTUIQ-UHFFFAOYSA-N n-[3-[2-[4-(4-pyrrolidin-1-ylpiperidin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(=CC=3)N3CCC(CC3)N3CCCC3)N=2)=C1 HNUGFTKBEBTUIQ-UHFFFAOYSA-N 0.000 claims 1
FHQJBLUAKWFDOG-UHFFFAOYSA-N n-[3-[2-[4-(4-tert-butylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C(C)(C)C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 FHQJBLUAKWFDOG-UHFFFAOYSA-N 0.000 claims 1
PLYLXYBCUZTVLR-UHFFFAOYSA-N n-[3-[2-[4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound CN1CC2CC1CN2C(C=C1)=CC=C1NC(N=C1C=CSC1=1)=NC=1OC1=CC=CC(NC(=O)C=C)=C1 PLYLXYBCUZTVLR-UHFFFAOYSA-N 0.000 claims 1
DEPTWANIEYZJFE-UHFFFAOYSA-N n-[3-[2-[4-(cyclopropylsulfamoyl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(=CC=3)S(=O)(=O)NC3CC3)N=2)=C1 DEPTWANIEYZJFE-UHFFFAOYSA-N 0.000 claims 1
VORFEMDIUABHDK-UHFFFAOYSA-N n-[3-[2-[4-(dimethylamino)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=CC(N(C)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 VORFEMDIUABHDK-UHFFFAOYSA-N 0.000 claims 1
LCIIKOVYESNSLK-UHFFFAOYSA-N n-[3-[2-[4-(methylsulfinylmethyl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=CC(CS(=O)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 LCIIKOVYESNSLK-UHFFFAOYSA-N 0.000 claims 1
TUBJUJIZDHZLMR-UHFFFAOYSA-N n-[3-[2-[4-(morpholin-4-ylmethyl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(CN4CCOCC4)=CC=3)N=2)=C1 TUBJUJIZDHZLMR-UHFFFAOYSA-N 0.000 claims 1
ROMKXEZIKSINRH-UHFFFAOYSA-N n-[3-[2-[4-(morpholine-4-carbonyl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(=CC=3)C(=O)N3CCOCC3)N=2)=C1 ROMKXEZIKSINRH-UHFFFAOYSA-N 0.000 claims 1
PIHHEWBQYVPQMZ-UHFFFAOYSA-N n-[3-[2-[4-(piperidin-1-ylmethyl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(CN4CCCCC4)=CC=3)N=2)=C1 PIHHEWBQYVPQMZ-UHFFFAOYSA-N 0.000 claims 1
MIZUJQFZBOMIEQ-UHFFFAOYSA-N n-[3-[2-[4-[(1-methylpiperidin-4-yl)amino]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCC1NC(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 MIZUJQFZBOMIEQ-UHFFFAOYSA-N 0.000 claims 1
FHNRAMZUCHQETC-UHFFFAOYSA-N n-[3-[2-[4-[(1-methylpiperidin-4-yl)sulfamoyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCC1NS(=O)(=O)C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 FHNRAMZUCHQETC-UHFFFAOYSA-N 0.000 claims 1
KPXFKOSXFMFWSF-UHFFFAOYSA-N n-[3-[2-[4-[(1-propan-2-ylpiperidin-4-yl)sulfamoyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C(C)C)CCC1NS(=O)(=O)C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 KPXFKOSXFMFWSF-UHFFFAOYSA-N 0.000 claims 1
RUKRDPXODWVRSI-CALCHBBNSA-N n-[3-[2-[4-[(2r,6s)-2,6-dimethylmorpholin-4-yl]-3-fluoroanilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 RUKRDPXODWVRSI-CALCHBBNSA-N 0.000 claims 1
XQVJJRBGGMDFCB-NRFANRHFSA-N n-[3-[2-[4-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1[C@@H](N(C)C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 XQVJJRBGGMDFCB-NRFANRHFSA-N 0.000 claims 1
RWGWSFWBNHFPIT-UHFFFAOYSA-N n-[3-[2-[4-[(4-ethylpiperazin-1-yl)methyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CC)CCN1CC(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 RWGWSFWBNHFPIT-UHFFFAOYSA-N 0.000 claims 1
WNRARNWBCIPKBI-UHFFFAOYSA-N n-[3-[2-[4-[(4-hydroxypiperidin-1-yl)methyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CC(O)CCN1CC(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 WNRARNWBCIPKBI-UHFFFAOYSA-N 0.000 claims 1
WJLPNIAIXXQTOM-UHFFFAOYSA-N n-[3-[2-[4-[(4-methylpiperazin-1-yl)methyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 WJLPNIAIXXQTOM-UHFFFAOYSA-N 0.000 claims 1
BVAOHNJUORKMHK-UHFFFAOYSA-N n-[3-[2-[4-[(4-morpholin-4-ylpiperidin-1-yl)methyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(CN4CCC(CC4)N4CCOCC4)=CC=3)N=2)=C1 BVAOHNJUORKMHK-UHFFFAOYSA-N 0.000 claims 1
BNHRCKBPHHCGRB-UHFFFAOYSA-N n-[3-[2-[4-[(dimethylamino)methyl]-3-fluoroanilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=C(F)C(CN(C)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 BNHRCKBPHHCGRB-UHFFFAOYSA-N 0.000 claims 1
AKLFIBVZWHENGA-VOTSOKGWSA-N n-[3-[2-[4-[(e)-3-(dimethylamino)prop-1-enyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=CC(/C=C/CN(C)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 AKLFIBVZWHENGA-VOTSOKGWSA-N 0.000 claims 1
ZHPNGVZRPNOBTI-UHFFFAOYSA-N n-[3-[2-[4-[1-(4-ethylpiperazin-1-yl)ethyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CC)CCN1C(C)C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ZHPNGVZRPNOBTI-UHFFFAOYSA-N 0.000 claims 1
IFZVYCZOSRCPHX-UHFFFAOYSA-N n-[3-[2-[4-[2-(4-ethylpiperazin-1-yl)acetyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CC)CCN1CC(=O)C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 IFZVYCZOSRCPHX-UHFFFAOYSA-N 0.000 claims 1
QJOFRWWBOBOBJZ-UHFFFAOYSA-N n-[3-[2-[4-[2-(4-ethylpiperazin-1-yl)ethyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CC)CCN1CCC(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 QJOFRWWBOBOBJZ-UHFFFAOYSA-N 0.000 claims 1
BEDINJYHAGCMSS-UHFFFAOYSA-N n-[3-[2-[4-[2-(4-ethylsulfonylpiperazin-1-yl)ethyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(S(=O)(=O)CC)CCN1CCC(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 BEDINJYHAGCMSS-UHFFFAOYSA-N 0.000 claims 1
QFTNOFKKXOCPCR-UHFFFAOYSA-N n-[3-[2-[4-[2-(4-methylpiperazin-1-yl)ethylamino]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1CCNC(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 QFTNOFKKXOCPCR-UHFFFAOYSA-N 0.000 claims 1
NLQKLPFYLIXUJS-UHFFFAOYSA-N n-[3-[2-[4-[2-(diethylamino)ethoxy]-3-fluoroanilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=C(F)C(OCCN(CC)CC)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 NLQKLPFYLIXUJS-UHFFFAOYSA-N 0.000 claims 1
MSTGVMBRJCYTHE-UHFFFAOYSA-N n-[3-[2-[4-[2-(diethylamino)ethoxy]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 MSTGVMBRJCYTHE-UHFFFAOYSA-N 0.000 claims 1
UXIVABWVJBVFRX-UHFFFAOYSA-N n-[3-[2-[4-[2-(dimethylamino)ethoxy]-3-fluoroanilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=C(F)C(OCCN(C)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 UXIVABWVJBVFRX-UHFFFAOYSA-N 0.000 claims 1
VGUALUXEUUXVOU-UHFFFAOYSA-N n-[3-[2-[4-[2-(dimethylamino)ethoxy]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 VGUALUXEUUXVOU-UHFFFAOYSA-N 0.000 claims 1
MTTLWNDXDJSOSH-UHFFFAOYSA-N n-[3-[2-[4-[2-(dimethylamino)ethyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=CC(CCN(C)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 MTTLWNDXDJSOSH-UHFFFAOYSA-N 0.000 claims 1
UJQKIEWKHLIGOC-UHFFFAOYSA-N n-[3-[2-[4-[2-(dimethylamino)ethylamino]-3,5-difluoroanilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=C(F)C(NCCN(C)C)=C(F)C=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 UJQKIEWKHLIGOC-UHFFFAOYSA-N 0.000 claims 1
LSAILEYADMCUMS-UHFFFAOYSA-N n-[3-[2-[4-[2-(dimethylamino)ethylamino]-3-fluoroanilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=C(F)C(NCCN(C)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 LSAILEYADMCUMS-UHFFFAOYSA-N 0.000 claims 1
ZTZHWTVWPBXDPA-UHFFFAOYSA-N n-[3-[2-[4-[2-(dimethylamino)ethylamino]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=CC(NCCN(C)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ZTZHWTVWPBXDPA-UHFFFAOYSA-N 0.000 claims 1
GCSFWYGODSJAIO-UHFFFAOYSA-N n-[3-[2-[4-[2-(dimethylamino)ethylsulfamoyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1=CC(S(=O)(=O)NCCN(C)C)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 GCSFWYGODSJAIO-UHFFFAOYSA-N 0.000 claims 1
CZXZSMXDPYMBCU-UHFFFAOYSA-N n-[3-[2-[4-[2-[(1-methylpiperidin-4-yl)amino]-2-oxoethyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCC1NC(=O)CC(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 CZXZSMXDPYMBCU-UHFFFAOYSA-N 0.000 claims 1
NBFHBAAQCBELRC-UHFFFAOYSA-N n-[3-[2-[4-[3-(methylamino)pyrrolidine-1-carbonyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1C(NC)CCN1C(=O)C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 NBFHBAAQCBELRC-UHFFFAOYSA-N 0.000 claims 1
NGDFPGCUNSZJLP-UHFFFAOYSA-N n-[3-[2-[4-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCC1N1CCN(C=2C=CC(NC=3N=C4C=CSC4=C(OC=4C=C(NC(=O)C=C)C=CC=4)N=3)=CC=2)CC1 NGDFPGCUNSZJLP-UHFFFAOYSA-N 0.000 claims 1
LHNVHIKKOQNOEQ-UHFFFAOYSA-N n-[3-[2-[4-[4-(1-methylpiperidin-4-yl)piperazine-1-carbonyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCC1N1CCN(C(=O)C=2C=CC(NC=3N=C4C=CSC4=C(OC=4C=C(NC(=O)C=C)C=CC=4)N=3)=CC=2)CC1 LHNVHIKKOQNOEQ-UHFFFAOYSA-N 0.000 claims 1
MOJXPKHLRNMLSL-UHFFFAOYSA-N n-[3-[2-[4-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CC(F)(F)F)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 MOJXPKHLRNMLSL-UHFFFAOYSA-N 0.000 claims 1
BWCZXAJVWXOBOQ-UHFFFAOYSA-N n-[3-[2-[4-[4-(2,2-difluoroethyl)piperazin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CC(F)F)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 BWCZXAJVWXOBOQ-UHFFFAOYSA-N 0.000 claims 1
ITKPZRDXQACKHU-UHFFFAOYSA-N n-[3-[2-[4-[4-(2-fluoroethyl)piperazin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CCF)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ITKPZRDXQACKHU-UHFFFAOYSA-N 0.000 claims 1
DYBXDSIUDRTQCB-UHFFFAOYSA-N n-[3-[2-[4-[4-(2-hydroxyacetyl)piperazin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C(=O)CO)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 DYBXDSIUDRTQCB-UHFFFAOYSA-N 0.000 claims 1
MTDDJUIATSIVAY-UHFFFAOYSA-N n-[3-[2-[4-[4-(2-hydroxyethyl)piperazin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CCO)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 MTDDJUIATSIVAY-UHFFFAOYSA-N 0.000 claims 1
ACEHACURALCMLJ-UHFFFAOYSA-N n-[3-[2-[4-[4-(2-hydroxyethyl)piperidin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CC(CCO)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ACEHACURALCMLJ-UHFFFAOYSA-N 0.000 claims 1
UWEVULWNUVFDGD-UHFFFAOYSA-N n-[3-[2-[4-[4-(2-methoxyethyl)piperazin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CCOC)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 UWEVULWNUVFDGD-UHFFFAOYSA-N 0.000 claims 1
HYFCVPUUKBHRLR-UHFFFAOYSA-N n-[3-[2-[4-[4-(dimethylamino)piperidin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 HYFCVPUUKBHRLR-UHFFFAOYSA-N 0.000 claims 1
ANSCOPFJFYTCMS-UHFFFAOYSA-N n-[3-[2-[4-[4-(dimethylsulfamoyl)piperazin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ANSCOPFJFYTCMS-UHFFFAOYSA-N 0.000 claims 1
ANHUCFWHUCHOIZ-UHFFFAOYSA-N n-[3-[2-[4-[4-(hydroxymethyl)piperidin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CC(CO)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ANHUCFWHUCHOIZ-UHFFFAOYSA-N 0.000 claims 1
MZWONPIPVJKSMI-UHFFFAOYSA-N n-[3-[2-[4-[4-(morpholine-4-carbonyl)piperazin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(=CC=3)N3CCN(CC3)C(=O)N3CCOCC3)N=2)=C1 MZWONPIPVJKSMI-UHFFFAOYSA-N 0.000 claims 1
UOGJCLDBCGVJTI-UHFFFAOYSA-N n-[3-[2-[4-[4-(piperidin-1-ylmethyl)piperidin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(=CC=3)N3CCC(CN4CCCCC4)CC3)N=2)=C1 UOGJCLDBCGVJTI-UHFFFAOYSA-N 0.000 claims 1
COOSSIHKRGQMLZ-UHFFFAOYSA-N n-[3-[2-[4-[4-[(dimethylamino)methyl]piperidin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CC(CN(C)C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 COOSSIHKRGQMLZ-UHFFFAOYSA-N 0.000 claims 1
WOFBBWFYUIGWRK-UHFFFAOYSA-N n-[3-[2-[4-[4-[2-(dimethylamino)acetyl]piperazin-1-yl]-3-fluoroanilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C(=O)CN(C)C)CCN1C(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 WOFBBWFYUIGWRK-UHFFFAOYSA-N 0.000 claims 1
GZHDEPFUGDNQBR-UHFFFAOYSA-N n-[3-[2-[4-[4-[2-(dimethylamino)acetyl]piperazin-1-yl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C(=O)CN(C)C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 GZHDEPFUGDNQBR-UHFFFAOYSA-N 0.000 claims 1
HMNHICZIPDCXOI-UHFFFAOYSA-N n-[3-[2-[4-[[3-(dimethylamino)pyrrolidin-1-yl]methyl]-3-fluoroanilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1C(N(C)C)CCN1CC(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 HMNHICZIPDCXOI-UHFFFAOYSA-N 0.000 claims 1
XUHZHQCRUUGYQF-UHFFFAOYSA-N n-[3-[2-[4-[[3-(dimethylamino)pyrrolidin-1-yl]methyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1C(N(C)C)CCN1CC(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 XUHZHQCRUUGYQF-UHFFFAOYSA-N 0.000 claims 1
QBHALGIZEXFTBS-UHFFFAOYSA-N n-[3-[2-[4-[[4-(1-methylpiperidin-4-yl)piperazin-1-yl]methyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCC1N1CCN(CC=2C=CC(NC=3N=C4C=CSC4=C(OC=4C=C(NC(=O)C=C)C=CC=4)N=3)=CC=2)CC1 QBHALGIZEXFTBS-UHFFFAOYSA-N 0.000 claims 1
GHGUSSUBRUYXOQ-UHFFFAOYSA-N n-[3-[2-[4-[[4-(cyclopropylmethyl)piperazin-1-yl]methyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(CN4CCN(CC5CC5)CC4)=CC=3)N=2)=C1 GHGUSSUBRUYXOQ-UHFFFAOYSA-N 0.000 claims 1
ZOIAUCPWBVPLQX-UHFFFAOYSA-N n-[3-[2-[4-[[4-(dimethylamino)piperidin-1-yl]methyl]-3-fluoroanilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CC(N(C)C)CCN1CC(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ZOIAUCPWBVPLQX-UHFFFAOYSA-N 0.000 claims 1
SWOPJQKTHDPAEL-UHFFFAOYSA-N n-[3-[2-[4-[[4-(dimethylamino)piperidin-1-yl]methyl]anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CC(N(C)C)CCN1CC(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 SWOPJQKTHDPAEL-UHFFFAOYSA-N 0.000 claims 1
XBZKAICZTBMLEA-UHFFFAOYSA-N n-[3-[2-[[1-[2-(dimethylamino)acetyl]-2,3-dihydroindol-5-yl]amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=1C=C2N(C(=O)CN(C)C)CCC2=CC=1NC(N=C1C=CSC1=1)=NC=1OC1=CC=CC(NC(=O)C=C)=C1 XBZKAICZTBMLEA-UHFFFAOYSA-N 0.000 claims 1
CKPUFSSNDGJRRO-UHFFFAOYSA-N n-[3-[2-[[5-[4-(2-hydroxyethyl)piperazin-1-yl]pyridin-2-yl]amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CCO)CCN1C(C=N1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 CKPUFSSNDGJRRO-UHFFFAOYSA-N 0.000 claims 1
SEDUBYZRQPXZAD-UHFFFAOYSA-N n-[3-[2-[[6-(2-piperidin-1-ylethylamino)pyridin-3-yl]amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=NC(NCCN4CCCCC4)=CC=3)N=2)=C1 SEDUBYZRQPXZAD-UHFFFAOYSA-N 0.000 claims 1
DIFRWOOHSXTTPR-UHFFFAOYSA-N n-[3-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 DIFRWOOHSXTTPR-UHFFFAOYSA-N 0.000 claims 1
OPSIOPMXERWSOG-UHFFFAOYSA-N n-[3-[2-[[6-(4-piperidin-1-ylpiperidin-1-yl)pyridin-3-yl]amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=NC(=CC=3)N3CCC(CC3)N3CCCCC3)N=2)=C1 OPSIOPMXERWSOG-UHFFFAOYSA-N 0.000 claims 1
OHGDUDXLXPRWKQ-UHFFFAOYSA-N n-[3-[2-[[6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyridin-3-yl]amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=NC(=CC=3)N3CCC(CC3)N3CCCC3)N=2)=C1 OHGDUDXLXPRWKQ-UHFFFAOYSA-N 0.000 claims 1
OPQNUUJJQNBGFG-UHFFFAOYSA-N n-[3-[2-[[6-[(1-propan-2-ylpiperidin-4-yl)amino]pyridin-3-yl]amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C(C)C)CCC1NC(N=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 OPQNUUJJQNBGFG-UHFFFAOYSA-N 0.000 claims 1
COOVKSWTUVHVNZ-UHFFFAOYSA-N n-[3-[2-[[6-[(4-methylpiperazin-1-yl)methyl]pyridin-3-yl]amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1CC(N=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 COOVKSWTUVHVNZ-UHFFFAOYSA-N 0.000 claims 1
PLGOXYSOTOBVDJ-UHFFFAOYSA-N n-[3-[2-[[6-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]pyridin-3-yl]amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCC1N1CCN(C=2N=CC(NC=3N=C4C=CSC4=C(OC=4C=C(NC(=O)C=C)C=CC=4)N=3)=CC=2)CC1 PLGOXYSOTOBVDJ-UHFFFAOYSA-N 0.000 claims 1
GWNLZXMQHOUQLR-UHFFFAOYSA-N n-[3-[2-[[6-[4-(dimethylamino)piperidin-1-yl]pyridin-3-yl]amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CC(N(C)C)CCN1C(N=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 GWNLZXMQHOUQLR-UHFFFAOYSA-N 0.000 claims 1
ZWVKEJGYVZTDOP-UHFFFAOYSA-N n-[3-[2-[[6-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]pyridin-3-yl]amino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(CCN(C)C)CCN1C(N=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ZWVKEJGYVZTDOP-UHFFFAOYSA-N 0.000 claims 1
BEFPYAYUCSNYES-UHFFFAOYSA-N n-[3-[[2-[4-(1-methylpiperidin-3-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]amino]phenyl]prop-2-enamide Chemical compound C1N(C)CCCC1C(C=C1)=CC=C1NC1=NC(NC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 BEFPYAYUCSNYES-UHFFFAOYSA-N 0.000 claims 1
ZTHVSMUBNJKEMY-UHFFFAOYSA-N n-[3-[[2-[4-(1-methylpiperidin-4-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]amino]phenyl]prop-2-enamide Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC1=NC(NC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ZTHVSMUBNJKEMY-UHFFFAOYSA-N 0.000 claims 1
WJQUALAYEOVEER-UHFFFAOYSA-N n-[3-[[2-[4-(4-ethylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]amino]phenyl]prop-2-enamide Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(NC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 WJQUALAYEOVEER-UHFFFAOYSA-N 0.000 claims 1
LUNNHPIHWNYMDF-UHFFFAOYSA-N n-[3-[[2-[4-(4-methylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]amino]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(NC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 LUNNHPIHWNYMDF-UHFFFAOYSA-N 0.000 claims 1
INYLGZXWICJCNB-UHFFFAOYSA-N n-[3-[[2-[4-(4-propan-2-ylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]amino]phenyl]prop-2-enamide Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC1=NC(NC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 INYLGZXWICJCNB-UHFFFAOYSA-N 0.000 claims 1
ICWBOKDWEYPDBE-UHFFFAOYSA-N n-[3-[[2-[4-[2-(4-methylpiperazin-1-yl)ethyl]anilino]thieno[3,2-d]pyrimidin-4-yl]amino]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1CCC(C=C1)=CC=C1NC1=NC(NC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ICWBOKDWEYPDBE-UHFFFAOYSA-N 0.000 claims 1
ZPFHPQTXDIXLAM-UHFFFAOYSA-N n-[3-[[2-[4-[2-(dimethylamino)ethoxy]anilino]thieno[3,2-d]pyrimidin-4-yl]amino]phenyl]prop-2-enamide Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(NC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 ZPFHPQTXDIXLAM-UHFFFAOYSA-N 0.000 claims 1
UIAHCCPZIYODSZ-UHFFFAOYSA-N n-[3-[[2-[4-[2-(dimethylamino)ethyl]anilino]thieno[3,2-d]pyrimidin-4-yl]amino]phenyl]prop-2-enamide Chemical compound C1=CC(CCN(C)C)=CC=C1NC1=NC(NC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 UIAHCCPZIYODSZ-UHFFFAOYSA-N 0.000 claims 1
WHYKPQZPZZTXML-UHFFFAOYSA-N n-[3-[[2-[4-[3-(dimethylamino)propoxy]anilino]thieno[3,2-d]pyrimidin-4-yl]amino]phenyl]prop-2-enamide Chemical compound C1=CC(OCCCN(C)C)=CC=C1NC1=NC(NC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 WHYKPQZPZZTXML-UHFFFAOYSA-N 0.000 claims 1
FUIUIKRJPKFFLC-UHFFFAOYSA-N n-[4-[[4-[3-(prop-2-enoylamino)phenoxy]thieno[3,2-d]pyrimidin-2-yl]amino]phenyl]-3-pyrrolidin-1-ylpropanamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3SC=CC=3N=C(NC=3C=CC(NC(=O)CCN4CCCC4)=CC=3)N=2)=C1 FUIUIKRJPKFFLC-UHFFFAOYSA-N 0.000 claims 1
WZGQRRGEZWDOIA-UHFFFAOYSA-N n-[4-fluoro-3-[2-[4-(4-methylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C(=CC=C(NC(=O)C=C)C=2)F)=C(SC=C2)C2=N1 WZGQRRGEZWDOIA-UHFFFAOYSA-N 0.000 claims 1
MMHDCKVDIIMOTJ-UHFFFAOYSA-N n-[4-fluoro-3-[[2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]amino]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC=C1NC1=NC(NC=2C(=CC=C(NC(=O)C=C)C=2)F)=C(SC=C2)C2=N1 MMHDCKVDIIMOTJ-UHFFFAOYSA-N 0.000 claims 1
CAZNOIGZOMUAFG-UHFFFAOYSA-N n-[4-fluoro-3-[[2-[4-(4-methylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]amino]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(NC=2C(=CC=C(NC(=O)C=C)C=2)F)=C(SC=C2)C2=N1 CAZNOIGZOMUAFG-UHFFFAOYSA-N 0.000 claims 1
DZPFGPRUVJQRDP-UHFFFAOYSA-N n-[4-methoxy-3-[2-[4-(4-methylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound COC1=CC=C(NC(=O)C=C)C=C1OC1=NC(NC=2C=CC(=CC=2)N2CCN(C)CC2)=NC2=C1SC=C2 DZPFGPRUVJQRDP-UHFFFAOYSA-N 0.000 claims 1
LRQGGNMSAKGHEN-UHFFFAOYSA-N n-[4-methyl-3-[2-[4-(4-methylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C(=CC=C(NC(=O)C=C)C=2)C)=C(SC=C2)C2=N1 LRQGGNMSAKGHEN-UHFFFAOYSA-N 0.000 claims 1
XOAWGOIGVWIXFT-UHFFFAOYSA-N n-methyl-4-[[4-[3-(prop-2-enoylamino)phenoxy]thieno[3,2-d]pyrimidin-2-yl]amino]benzamide Chemical compound C1=CC(C(=O)NC)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(SC=C2)C2=N1 XOAWGOIGVWIXFT-UHFFFAOYSA-N 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
210000000056 organ Anatomy 0.000 claims 1
201000008482 osteoarthritis Diseases 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
230000002265 prevention Effects 0.000 claims 1
201000003651 pulmonary sarcoidosis Diseases 0.000 claims 1
206010039073 rheumatoid arthritis Diseases 0.000 claims 1
229920006395 saturated elastomer Polymers 0.000 claims 1
201000005671 spondyloarthropathy Diseases 0.000 claims 1
230000003637 steroidlike Effects 0.000 claims 1
125000003107 substituted aryl group Chemical group 0.000 claims 1
150000003512 tertiary amines Chemical class 0.000 claims 1
229940044693 topoisomerase inhibitor Drugs 0.000 claims 1
238000002689 xenotransplantation Methods 0.000 claims 1

JP2013516501A 2010-06-23 2011-06-20 チロシンキナーゼ活性阻害作用を有する新規な縮合ピリミジン誘導体 Active JP5834347B2 (ja)