JP2013529630A5 - - Google Patents
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- JP2013529630A5 JP2013529630A5 JP2013516501A JP2013516501A JP2013529630A5 JP 2013529630 A5 JP2013529630 A5 JP 2013529630A5 JP 2013516501 A JP2013516501 A JP 2013516501A JP 2013516501 A JP2013516501 A JP 2013516501A JP 2013529630 A5 JP2013529630 A5 JP 2013529630A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- thieno
- pyrimidin
- acrylamide
- yloxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 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
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 208000003950 B-cell lymphoma Diseases 0.000 claims 1
- 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
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- 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
- 201000005569 Gout Diseases 0.000 claims 1
- 206010018634 Gouty Arthritis Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 101001050476 Homo sapiens Tyrosine-protein kinase ITK/TSK Proteins 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims 1
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000007201 Myocardial reperfusion injury Diseases 0.000 claims 1
- GEZLPGGQCUWCPD-UHFFFAOYSA-N N-[3-[2-[4-(3-piperidin-1-ylprop-1-enyl)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(C=CCN4CCCCC4)=CC=3)N=2)=C1 GEZLPGGQCUWCPD-UHFFFAOYSA-N 0.000 claims 1
- 125000000815 N-oxide group Chemical group 0.000 claims 1
- WDCHCSPFFANTFK-UHFFFAOYSA-N N1(C=NC=C1)C1=CC=C(C=C1)NC1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N Chemical compound N1(C=NC=C1)C1=CC=C(C=C1)NC1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N WDCHCSPFFANTFK-UHFFFAOYSA-N 0.000 claims 1
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- OJHKVHQVXIIEGA-UHFFFAOYSA-N N1(CCCC1)CN(C1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N)C2=CC=CC=C2 Chemical compound N1(CCCC1)CN(C1(C2=C(N=CN1)C=CS2)OC2=C(C=CC=C2)C=CC(=O)N)C2=CC=CC=C2 OJHKVHQVXIIEGA-UHFFFAOYSA-N 0.000 claims 1
- BPDXENYDHQSARI-UHFFFAOYSA-N N1(CCCCC1)CN(C1(C2=C(N=CN1)C=CS2)NC2=C(C=CC=C2)C=CC(=O)N)C2=CC=CC=C2 Chemical compound N1(CCCCC1)CN(C1(C2=C(N=CN1)C=CS2)NC2=C(C=CC=C2)C=CC(=O)N)C2=CC=CC=C2 BPDXENYDHQSARI-UHFFFAOYSA-N 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
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- 206010039710 Scleroderma Diseases 0.000 claims 1
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- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 102100023345 Tyrosine-protein kinase ITK/TSK Human genes 0.000 claims 1
- 101710101516 Tyrosine-protein kinase TXK Proteins 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000024780 Urticaria Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 239000000739 antihistaminic agent Substances 0.000 claims 1
- 229940125715 antihistaminic agent Drugs 0.000 claims 1
- 239000013059 antihormonal agent Substances 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 230000002917 arthritic effect Effects 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
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- 208000010668 atopic eczema Diseases 0.000 claims 1
- 208000010928 autoimmune thyroid disease Diseases 0.000 claims 1
- 210000003719 b-lymphocyte Anatomy 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 229940046731 calcineurin inhibitors Drugs 0.000 claims 1
- 201000003984 candidiasis Diseases 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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