RU2437888C2 - Ингибиторы фосфоинозитид-3-киназы и содержащие их фармацевтические композиции - Google Patents

Info

Publication number

RU2437888C2

RU2437888C2 RU2008145662/04A RU2008145662A RU2437888C2 RU 2437888 C2 RU2437888 C2 RU 2437888C2 RU 2008145662/04 A RU2008145662/04 A RU 2008145662/04A RU 2008145662 A RU2008145662 A RU 2008145662A RU 2437888 C2 RU2437888 C2 RU 2437888C2

Authority

RU

Russia

Prior art keywords

indazol

morpholinothieno

pyrimidin

pyrimidine

methyl

Prior art date

2006-04-26

Links

• Espacenet
• Global Dossier
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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 4
• 239000003112 inhibitor Substances 0.000 title 1
• 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title 1
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract 49
• -1 thiopyranyl Chemical group 0.000 claims abstract 47
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 18
• 125000000217 alkyl group Chemical group 0.000 claims abstract 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 18
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract 14
• 229910052799 carbon Inorganic materials 0.000 claims abstract 10
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract 10
• 150000002632 lipids Chemical class 0.000 claims abstract 10
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract 10
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract 9
• 102000020233 phosphotransferase Human genes 0.000 claims abstract 9
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract 8
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract 8
• 230000000694 effects Effects 0.000 claims abstract 8
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract 7
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract 7
• 125000004452 carbocyclyl group Chemical group 0.000 claims abstract 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract 6
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract 4
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract 4
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract 3
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 3
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract 2
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims abstract 2
• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims abstract 2
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims abstract 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract 2
• 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 2
• 125000000304 alkynyl group Chemical group 0.000 claims abstract 2
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract 2
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract 2
• 239000000203 mixture Substances 0.000 claims abstract 2
• 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
• 125000006413 ring segment Chemical group 0.000 claims abstract 2
• 150000003839 salts Chemical class 0.000 claims abstract 2
• 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
• 125000000335 thiazolyl group Chemical group 0.000 claims abstract 2
• 150000003852 triazoles Chemical class 0.000 claims abstract 2
• OXPJULAQXGHXMG-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(phenoxymethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1COC1=CC=CC=C1 OXPJULAQXGHXMG-UHFFFAOYSA-N 0.000 claims description 3
• SDAQMUGYAHYOTK-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(pyridin-2-ylmethoxymethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1COCC1=CC=CC=N1 SDAQMUGYAHYOTK-UHFFFAOYSA-N 0.000 claims description 3
• SNVYLDINYINJBQ-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(pyridin-3-ylmethoxymethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1COCC1=CC=CN=C1 SNVYLDINYINJBQ-UHFFFAOYSA-N 0.000 claims description 3
• SUUPOLANUWSKJH-UHFFFAOYSA-N 3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n,n-dimethylpropanamide Chemical compound C=12SC(CCC(=O)N(C)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 SUUPOLANUWSKJH-UHFFFAOYSA-N 0.000 claims description 2
• RUYRUQRDGRFBMV-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(methylsulfonylmethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(CS(=O)(=O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 RUYRUQRDGRFBMV-UHFFFAOYSA-N 0.000 claims description 2
• USBBZDKANYQYJR-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(phenylmethoxymethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1COCC1=CC=CC=C1 USBBZDKANYQYJR-UHFFFAOYSA-N 0.000 claims description 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
• 102000038030 PI3Ks Human genes 0.000 claims 3
• 108091007960 PI3Ks Proteins 0.000 claims 3
• 239000003937 drug carrier Substances 0.000 claims 3
• 230000002401 inhibitory effect Effects 0.000 claims 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
• 125000004193 piperazinyl group Chemical group 0.000 claims 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
• PCFRKLDFVDAEFU-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-yl-6-phenylfuro[3,2-d]pyrimidine Chemical compound C1COCCN1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1OC(C=1C=CC=CC=1)=C2 PCFRKLDFVDAEFU-UHFFFAOYSA-N 0.000 claims 2
• YKEDKDPZBFWVGS-UHFFFAOYSA-N 2-[2-(2-methyl-1h-imidazo[4,5-b]pyridin-6-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]propan-2-ol Chemical compound C=1N=C2NC(C)=NC2=CC=1C(N=C1SC(=CC1=1)C(C)(C)O)=NC=1N1CCOCC1 YKEDKDPZBFWVGS-UHFFFAOYSA-N 0.000 claims 2
• FFWWPZCGHGDPFH-UHFFFAOYSA-N 2-[4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl]propan-2-ol Chemical compound N1=C(C=2C=C3C=CNC3=NC=2)N=C2SC(C(C)(O)C)=CC2=C1N1CCOCC1 FFWWPZCGHGDPFH-UHFFFAOYSA-N 0.000 claims 2
• UTIBOKQOUFWJBY-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(pyridin-4-ylmethoxymethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1COCC1=CC=NC=C1 UTIBOKQOUFWJBY-UHFFFAOYSA-N 0.000 claims 2
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
• 125000004411 C5-C6 heterocyclyl group Chemical group 0.000 claims 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
• 241000124008 Mammalia Species 0.000 claims 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
• ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 2
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 2
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
• 125000002757 morpholinyl group Chemical group 0.000 claims 2
• JSRNAKDXAPQVRG-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]acetamide Chemical compound C=12SC(CNC(=O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 JSRNAKDXAPQVRG-UHFFFAOYSA-N 0.000 claims 2
• ZVDDUFKZPHXCSI-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NCC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 ZVDDUFKZPHXCSI-UHFFFAOYSA-N 0.000 claims 2
• NSTMDEWDLPFQQT-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NCC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 NSTMDEWDLPFQQT-UHFFFAOYSA-N 0.000 claims 2
• RABOWVBQXMWRQH-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]pyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NCC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 RABOWVBQXMWRQH-UHFFFAOYSA-N 0.000 claims 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
• JMXRKVAGXKMIPZ-LLVKDONJSA-N (1r)-1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidin-6-yl]ethanol Chemical compound C=12OC([C@H](O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 JMXRKVAGXKMIPZ-LLVKDONJSA-N 0.000 claims 1
• VIOPFQOZMDFRIZ-LLVKDONJSA-N (1r)-1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]ethanol Chemical compound C=12SC([C@H](O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 VIOPFQOZMDFRIZ-LLVKDONJSA-N 0.000 claims 1
• JMXRKVAGXKMIPZ-NSHDSACASA-N (1s)-1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidin-6-yl]ethanol Chemical compound C=12OC([C@@H](O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 JMXRKVAGXKMIPZ-NSHDSACASA-N 0.000 claims 1
• VIOPFQOZMDFRIZ-NSHDSACASA-N (1s)-1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]ethanol Chemical compound C=12SC([C@@H](O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 VIOPFQOZMDFRIZ-NSHDSACASA-N 0.000 claims 1
• RKVSZDRDBKKPAP-MRXNPFEDSA-N (2r)-1-[3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]sulfonylpropan-2-ol Chemical compound C[C@@H](O)CS(=O)(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 RKVSZDRDBKKPAP-MRXNPFEDSA-N 0.000 claims 1
• RKVSZDRDBKKPAP-INIZCTEOSA-N (2s)-1-[3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]sulfonylpropan-2-ol Chemical compound C[C@H](O)CS(=O)(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 RKVSZDRDBKKPAP-INIZCTEOSA-N 0.000 claims 1
• DUCDTCHVXCKKRX-INIZCTEOSA-N (2s)-1-[3-[7-methyl-4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl]phenyl]sulfonylpropan-2-ol Chemical compound C[C@H](O)CS(=O)(=O)C1=CC=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=C3C=CNC3=NC=2)C)=C1 DUCDTCHVXCKKRX-INIZCTEOSA-N 0.000 claims 1
• CUYITMLSLMYMHZ-ZDUSSCGKSA-N (2s)-1-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methylamino]propan-2-ol Chemical compound C=12SC(CNC[C@@H](O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 CUYITMLSLMYMHZ-ZDUSSCGKSA-N 0.000 claims 1
• BTXLWOORFZYYQO-HNNXBMFYSA-N (2s)-2-hydroxy-n-[3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]propanamide Chemical compound C[C@H](O)C(=O)NC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 BTXLWOORFZYYQO-HNNXBMFYSA-N 0.000 claims 1
• UYVMVHJNWHTYSN-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methanone Chemical compound C1CC(O)CCN1C(=O)C1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 UYVMVHJNWHTYSN-UHFFFAOYSA-N 0.000 claims 1
• WAEOVUWCYLULQY-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methanone Chemical compound C1CC(O)CCN1C(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 WAEOVUWCYLULQY-UHFFFAOYSA-N 0.000 claims 1
• VIURXCVRUARQCR-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-[3-[7-methyl-4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl]phenyl]methanone Chemical compound N1=C(C=2C=C3C=CNC3=NC=2)N=C2C(C)=C(C=3C=C(C=CC=3)C(=O)N3CCC(O)CC3)SC2=C1N1CCOCC1 VIURXCVRUARQCR-UHFFFAOYSA-N 0.000 claims 1
• HOWCYUAEDIVXNE-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[3-[4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(C=2SC3=NC(=NC(=C3C=2)N2CCOCC2)C=2C=C3C=CNC3=NC=2)=C1 HOWCYUAEDIVXNE-UHFFFAOYSA-N 0.000 claims 1
• ZKFUDKPHKURGQZ-UHFFFAOYSA-N 1-(diethylamino)-2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound C=12SC(C(C)(O)CN(CC)CC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 ZKFUDKPHKURGQZ-UHFFFAOYSA-N 0.000 claims 1
• JMXRKVAGXKMIPZ-UHFFFAOYSA-N 1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidin-6-yl]ethanol Chemical compound C=12OC(C(O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 JMXRKVAGXKMIPZ-UHFFFAOYSA-N 0.000 claims 1
• JYYZJYRXKDZPCT-UHFFFAOYSA-N 1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]-3-(4-methylsulfonylpiperazin-1-yl)propan-2-one Chemical compound C1CN(S(=O)(=O)C)CCN1CC(=O)CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 JYYZJYRXKDZPCT-UHFFFAOYSA-N 0.000 claims 1
• NGGWNTYJNZWBMJ-UHFFFAOYSA-N 1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]ethanol Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2SC(C(O)C)=CC2=C1N1CCOCC1 NGGWNTYJNZWBMJ-UHFFFAOYSA-N 0.000 claims 1
• ONWMYODREYYYMH-UHFFFAOYSA-N 1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-2-methylpropan-2-ol Chemical compound C=12SC(CC(C)(O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 ONWMYODREYYYMH-UHFFFAOYSA-N 0.000 claims 1
• LSJWZUXCIJQWLS-UHFFFAOYSA-N 1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n,n-dimethylmethanamine Chemical compound C=12SC(CN(C)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 LSJWZUXCIJQWLS-UHFFFAOYSA-N 0.000 claims 1
• NCWLVFNJIPBEOJ-UHFFFAOYSA-N 1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-methylmethanamine Chemical compound C=12SC(CNC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 NCWLVFNJIPBEOJ-UHFFFAOYSA-N 0.000 claims 1
• DSGDVGKDWAMYTM-UHFFFAOYSA-N 1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]cyclobutan-1-ol Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1C1(O)CCC1 DSGDVGKDWAMYTM-UHFFFAOYSA-N 0.000 claims 1
• BKLQJXVOFOBSNX-UHFFFAOYSA-N 1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 BKLQJXVOFOBSNX-UHFFFAOYSA-N 0.000 claims 1
• HWFXCRFJUMYUFM-UHFFFAOYSA-N 1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]sulfonylpiperidin-4-ol Chemical compound C1CC(O)CCN1S(=O)(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 HWFXCRFJUMYUFM-UHFFFAOYSA-N 0.000 claims 1
• PNHATHRYVLOEIR-UHFFFAOYSA-N 1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]sulfonylpyrrolidin-3-ol Chemical compound C1C(O)CCN1S(=O)(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 PNHATHRYVLOEIR-UHFFFAOYSA-N 0.000 claims 1
• GROBNFFBQIRGSZ-UHFFFAOYSA-N 1-[4-(4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)-2,3-dihydroindol-1-yl]ethanone Chemical compound CC(=O)N1CCC2=C1C=CC=C2C(N=C1C=CSC1=1)=NC=1N1CCOCC1 GROBNFFBQIRGSZ-UHFFFAOYSA-N 0.000 claims 1
• CRCSKZIPKQHVOI-UHFFFAOYSA-N 1-[4-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidine-6-carbonyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(=O)C1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 CRCSKZIPKQHVOI-UHFFFAOYSA-N 0.000 claims 1
• KUUKIIAOCWZYSX-UHFFFAOYSA-N 1-[4-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]sulfonylpiperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1S(=O)(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 KUUKIIAOCWZYSX-UHFFFAOYSA-N 0.000 claims 1
• LJKVWBKQZFRWPY-UHFFFAOYSA-N 1-[4-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carbonyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 LJKVWBKQZFRWPY-UHFFFAOYSA-N 0.000 claims 1
• YCBDEZWXCLZIOY-UHFFFAOYSA-N 1-[4-hydroxy-4-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1(O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 YCBDEZWXCLZIOY-UHFFFAOYSA-N 0.000 claims 1
• HMLURENDJQQGCM-UHFFFAOYSA-N 1-benzothiophene;pyridine Chemical compound C1=CC=NC=C1.C1=CC=C2SC=CC2=C1 HMLURENDJQQGCM-UHFFFAOYSA-N 0.000 claims 1
• HOCCUNWGIYBWLU-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-yl-n-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2SC(C(=O)NCC(F)(F)F)=CC2=C1N1CCOCC1 HOCCUNWGIYBWLU-UHFFFAOYSA-N 0.000 claims 1
• JLVNYYWPIGRCTI-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-yl-n-(2,2,2-trifluoroethyl)thieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)NCC(F)(F)F)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 JLVNYYWPIGRCTI-UHFFFAOYSA-N 0.000 claims 1
• WRVFYDGHHSFFOC-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-yl-n-(2-morpholin-4-ylethyl)thieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1C(=O)NCCN1CCOCC1 WRVFYDGHHSFFOC-UHFFFAOYSA-N 0.000 claims 1
• HCZPBIDLAMVEBA-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-yl-n-(2-piperidin-1-ylethyl)thieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1C(=O)NCCN1CCCCC1 HCZPBIDLAMVEBA-UHFFFAOYSA-N 0.000 claims 1
• BHHHJNHPYSCFFH-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-yl-n-(2-piperidin-1-ylethyl)thieno[3,2-d]pyrimidine-6-sulfonamide Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1S(=O)(=O)NCCN1CCCCC1 BHHHJNHPYSCFFH-UHFFFAOYSA-N 0.000 claims 1
• SMIDKUYBKUDRKB-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-yl-n-phenylthieno[3,2-d]pyrimidin-6-amine Chemical compound C1COCCN1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1SC(NC=1C=CC=CC=1)=C2 SMIDKUYBKUDRKB-UHFFFAOYSA-N 0.000 claims 1
• ALOKKKPXBWDBSD-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-yl-n-phenylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1C(=O)NC1=CC=CC=C1 ALOKKKPXBWDBSD-UHFFFAOYSA-N 0.000 claims 1
• LGCKOOIOBWJBMG-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-yl-n-propan-2-ylthieno[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2SC(C(=O)NC(C)C)=CC2=C1N1CCOCC1 LGCKOOIOBWJBMG-UHFFFAOYSA-N 0.000 claims 1
• DRBJFZFLAJGRGA-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-yl-n-pyridin-2-ylthieno[3,2-d]pyrimidin-6-amine Chemical compound C1COCCN1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1SC(NC=1N=CC=CC=1)=C2 DRBJFZFLAJGRGA-UHFFFAOYSA-N 0.000 claims 1
• DLXYBNXLFJZKBH-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-yl-n-pyridin-3-ylthieno[3,2-d]pyrimidin-6-amine Chemical compound C1COCCN1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1SC(NC=1C=NC=CC=1)=C2 DLXYBNXLFJZKBH-UHFFFAOYSA-N 0.000 claims 1
• NIWKVJGJUJPBGK-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12OC(C(=O)N)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 NIWKVJGJUJPBGK-UHFFFAOYSA-N 0.000 claims 1
• UQEQBQDBQZQCJB-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2SC(C(=O)N)=CC2=C1N1CCOCC1 UQEQBQDBQZQCJB-UHFFFAOYSA-N 0.000 claims 1
• XNCSTYGCHDBACY-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidine-6-carboxylic acid Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2SC(C(=O)O)=CC2=C1N1CCOCC1 XNCSTYGCHDBACY-UHFFFAOYSA-N 0.000 claims 1
• FKOYCKMQWGADTH-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-amine Chemical compound C=12SC(N)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 FKOYCKMQWGADTH-UHFFFAOYSA-N 0.000 claims 1
• WWZAVDWPNSVWNN-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carbonitrile Chemical compound C=12SC(C#N)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 WWZAVDWPNSVWNN-UHFFFAOYSA-N 0.000 claims 1
• YBGBXFWZMOYLQD-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)N)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 YBGBXFWZMOYLQD-UHFFFAOYSA-N 0.000 claims 1
• FDDMBVCMOPBZFJ-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-6-(3-methylsulfonylphenyl)-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound CS(=O)(=O)C1=CC=CC(C=2OC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 FDDMBVCMOPBZFJ-UHFFFAOYSA-N 0.000 claims 1
• FHCJMLRUTSNNQI-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-6-(4-methoxypyridin-3-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound COC1=CC=NC=C1C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2O1 FHCJMLRUTSNNQI-UHFFFAOYSA-N 0.000 claims 1
• KWWCMVDYTRYWPH-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n,n-dimethyl-4-morpholin-4-ylthieno[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2SC(C(=O)N(C)C)=CC2=C1N1CCOCC1 KWWCMVDYTRYWPH-UHFFFAOYSA-N 0.000 claims 1
• BKDRTCOHEUFZFY-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n,n-dimethyl-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)N(C)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 BKDRTCOHEUFZFY-UHFFFAOYSA-N 0.000 claims 1
• FKIKJMKVWSALDP-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n,n-dimethyl-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-sulfonamide Chemical compound C=12SC(S(=O)(=O)N(C)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 FKIKJMKVWSALDP-UHFFFAOYSA-N 0.000 claims 1
• RDTCXYIQCWNFSK-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n-(2-methoxyethyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)NCCOC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 RDTCXYIQCWNFSK-UHFFFAOYSA-N 0.000 claims 1
• INXCTOSJLMMDFQ-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n-(2-methylpropyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)NCC(C)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 INXCTOSJLMMDFQ-UHFFFAOYSA-N 0.000 claims 1
• GUHFQJKAUMYZSE-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n-(2-methylpropyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-sulfonamide Chemical compound C=12SC(S(=O)(=O)NCC(C)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 GUHFQJKAUMYZSE-UHFFFAOYSA-N 0.000 claims 1
• TYQMLTKFRJHHEU-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n-(2-methylsulfonylethyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)NCCS(=O)(=O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 TYQMLTKFRJHHEU-UHFFFAOYSA-N 0.000 claims 1
• UAMBYKACPJDLSI-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n-(3-methoxypropyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-sulfonamide Chemical compound C=12SC(S(=O)(=O)NCCCOC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 UAMBYKACPJDLSI-UHFFFAOYSA-N 0.000 claims 1
• ZNFNHTKIPYOTTI-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n-methyl-4-morpholin-4-ylfuro[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12OC(C(=O)NC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 ZNFNHTKIPYOTTI-UHFFFAOYSA-N 0.000 claims 1
• LWGYLFNPXUGWPI-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n-methyl-4-morpholin-4-ylthieno[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2SC(C(=O)NC)=CC2=C1N1CCOCC1 LWGYLFNPXUGWPI-UHFFFAOYSA-N 0.000 claims 1
• SSCACCUKDLQYBG-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)NC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 SSCACCUKDLQYBG-UHFFFAOYSA-N 0.000 claims 1
• CQGVZXXBDFUOHQ-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-sulfonamide Chemical compound C=12SC(S(=O)(=O)NC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 CQGVZXXBDFUOHQ-UHFFFAOYSA-N 0.000 claims 1
• RIGJAZFHROFODF-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-n-methylsulfonyl-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)NS(=O)(=O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 RIGJAZFHROFODF-UHFFFAOYSA-N 0.000 claims 1
• RVAVFLAGEMAGCV-UHFFFAOYSA-N 2-(1h-indol-4-yl)-n-(2-methoxyethyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)NCCOC)=CC2=NC(C=2C=3C=CNC=3C=CC=2)=NC=1N1CCOCC1 RVAVFLAGEMAGCV-UHFFFAOYSA-N 0.000 claims 1
• QDXYIFDFRQUYRJ-UHFFFAOYSA-N 2-(4-morpholin-4-yl-2-quinolin-3-ylthieno[2,3-d]pyrimidin-6-yl)propan-2-ol Chemical compound N1=C(C=2C=C3C=CC=CC3=NC=2)N=C2SC(C(C)(O)C)=CC2=C1N1CCOCC1 QDXYIFDFRQUYRJ-UHFFFAOYSA-N 0.000 claims 1
• SAGKGTRXWNMVQJ-UHFFFAOYSA-N 2-(4-morpholin-4-yl-2-quinolin-3-ylthieno[3,2-d]pyrimidin-6-yl)propan-2-ol Chemical compound C=12SC(C(C)(O)C)=CC2=NC(C=2C=C3C=CC=CC3=NC=2)=NC=1N1CCOCC1 SAGKGTRXWNMVQJ-UHFFFAOYSA-N 0.000 claims 1
• CZZWHEQOSGGGBN-UHFFFAOYSA-N 2-(dimethylamino)-n-[3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]acetamide Chemical compound CN(C)CC(=O)NC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 CZZWHEQOSGGGBN-UHFFFAOYSA-N 0.000 claims 1
• WKJOQYHMXRVQDK-UHFFFAOYSA-N 2-(dimethylamino)acetamide Chemical compound CN(C)CC(N)=O WKJOQYHMXRVQDK-UHFFFAOYSA-N 0.000 claims 1
• FTKOJEJLOFKOHM-UHFFFAOYSA-N 2-[1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]sulfonylpiperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1S(=O)(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 FTKOJEJLOFKOHM-UHFFFAOYSA-N 0.000 claims 1
• IFSUIBXAHWRRLD-UHFFFAOYSA-N 2-[2-(1h-imidazo[4,5-b]pyridin-6-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound C=12SC(C(C)(O)C)=CC2=NC(C=2C=C3NC=NC3=NC=2)=NC=1N1CCOCC1 IFSUIBXAHWRRLD-UHFFFAOYSA-N 0.000 claims 1
• IPOHTGJEHGKOPX-UHFFFAOYSA-N 2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound C=12OC(C(C)(O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 IPOHTGJEHGKOPX-UHFFFAOYSA-N 0.000 claims 1
• UDTBHUGAUFWRRH-UHFFFAOYSA-N 2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]propan-2-ol Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2SC(C(C)(O)C)=CC2=C1N1CCOCC1 UDTBHUGAUFWRRH-UHFFFAOYSA-N 0.000 claims 1
• VILXMSHZYWBRPI-UHFFFAOYSA-N 2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-1,3-dimethoxypropan-2-ol Chemical compound C=12SC(C(O)(COC)COC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 VILXMSHZYWBRPI-UHFFFAOYSA-N 0.000 claims 1
• PERYMLMYBGAEAE-UHFFFAOYSA-N 2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-1-methoxypropan-2-ol Chemical compound C=12SC(C(C)(O)COC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 PERYMLMYBGAEAE-UHFFFAOYSA-N 0.000 claims 1
• YWMSDMTVEOEPFB-UHFFFAOYSA-N 2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]ethanol Chemical compound C=12SC(CCO)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 YWMSDMTVEOEPFB-UHFFFAOYSA-N 0.000 claims 1
• VARNVCFXTDKYGZ-UHFFFAOYSA-N 2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-amine Chemical compound C=12SC(C(C)(N)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 VARNVCFXTDKYGZ-UHFFFAOYSA-N 0.000 claims 1
• KYBJEPGFZBUXMW-UHFFFAOYSA-N 2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound C=12SC(C(C)(O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 KYBJEPGFZBUXMW-UHFFFAOYSA-N 0.000 claims 1
• TZKPJZZXKNAKRA-UHFFFAOYSA-N 2-[2-(1h-indol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound C=12SC(C(C)(O)C)=CC2=NC(C=2C=3C=CNC=3C=CC=2)=NC=1N1CCOCC1 TZKPJZZXKNAKRA-UHFFFAOYSA-N 0.000 claims 1
• OVKKSLJAZQJVGU-UHFFFAOYSA-N 2-[2-(1h-indol-6-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound C=12SC(C(C)(O)C)=CC2=NC(C=2C=C3NC=CC3=CC=2)=NC=1N1CCOCC1 OVKKSLJAZQJVGU-UHFFFAOYSA-N 0.000 claims 1
• QHLSLQBAQLNCKK-UHFFFAOYSA-N 2-[2-(2-methyl-1h-imidazo[4,5-b]pyridin-6-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound C=1N=C2NC(C)=NC2=CC=1C(N=C1C=C(SC1=1)C(C)(C)O)=NC=1N1CCOCC1 QHLSLQBAQLNCKK-UHFFFAOYSA-N 0.000 claims 1
• NSJBGAITKKJFCI-UHFFFAOYSA-N 2-[2-[[5-[7-methyl-4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]amino]ethoxy]ethanol Chemical compound N1=C(C=2C=C3C=CNC3=NC=2)N=C2C(C)=C(C=3C=NC(NCCOCCO)=CC=3)SC2=C1N1CCOCC1 NSJBGAITKKJFCI-UHFFFAOYSA-N 0.000 claims 1
• WMAVDUZEBKWJIO-UHFFFAOYSA-N 2-[4-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]sulfonylpiperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1S(=O)(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 WMAVDUZEBKWJIO-UHFFFAOYSA-N 0.000 claims 1
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• NBFZWXNPLNBPPB-UHFFFAOYSA-N 3-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 NBFZWXNPLNBPPB-UHFFFAOYSA-N 0.000 claims 1
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• LCFDEBGLEMGHBK-UHFFFAOYSA-N 3-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methylamino]-n,n-dimethylpropane-1-sulfonamide Chemical compound C=12SC(CNCCCS(=O)(=O)N(C)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 LCFDEBGLEMGHBK-UHFFFAOYSA-N 0.000 claims 1
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• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
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• KLIQKWLIFSOOQC-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(3-methoxypropylsulfonylmethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(CS(=O)(=O)CCCOC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 KLIQKWLIFSOOQC-UHFFFAOYSA-N 0.000 claims 1
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• RCTVICMXHIQSIZ-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(3-morpholin-4-ylprop-1-ynyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1CC#CC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 RCTVICMXHIQSIZ-UHFFFAOYSA-N 0.000 claims 1
• YAGBWYDWEROTGK-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(3-pyrrolidin-1-ylprop-1-ynyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CCCN1CC#CC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 YAGBWYDWEROTGK-UHFFFAOYSA-N 0.000 claims 1
• XDHDCRCCSVQZFV-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(4-methoxy-1-methylpiperidin-4-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1C1(OC)CCN(C)CC1 XDHDCRCCSVQZFV-UHFFFAOYSA-N 0.000 claims 1
• DLSJNHFRWWVXIB-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(4-methoxypyridin-3-yl)-7-methylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=NC=C1C1=C(C)C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 DLSJNHFRWWVXIB-UHFFFAOYSA-N 0.000 claims 1
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• XPRXKQFDUTUXHX-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(4-methoxypyridin-3-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=NC=C1C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 XPRXKQFDUTUXHX-UHFFFAOYSA-N 0.000 claims 1
• GIMVQGMRVBRNLM-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(4-methylpiperazin-1-yl)sulfonylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 GIMVQGMRVBRNLM-UHFFFAOYSA-N 0.000 claims 1
• MONDJTSTNHPMQP-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(4-methylsulfonylphenyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 MONDJTSTNHPMQP-UHFFFAOYSA-N 0.000 claims 1
• JFLITDAGHACDHY-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(4-methylsulfonylpiperazin-1-yl)sulfonylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1S(=O)(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 JFLITDAGHACDHY-UHFFFAOYSA-N 0.000 claims 1
• UIOKQIDDKFTTPO-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(6-morpholin-4-ylpyridin-3-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=CC=C(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)C=N1 UIOKQIDDKFTTPO-UHFFFAOYSA-N 0.000 claims 1
• XVGVRYRNKLUWCP-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(methoxymethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(COC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 XVGVRYRNKLUWCP-UHFFFAOYSA-N 0.000 claims 1
• ZNDZHZSAEBKIFF-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(pyrazol-1-ylmethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=CC=NN1CC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 ZNDZHZSAEBKIFF-UHFFFAOYSA-N 0.000 claims 1
• WSHIYMFHSNIBIR-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-(pyridin-3-yloxymethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1COC1=CC=CN=C1 WSHIYMFHSNIBIR-UHFFFAOYSA-N 0.000 claims 1
• GFGLIVBBQQFKCY-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(1-methylpiperidin-4-ylidene)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCC1=CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 GFGLIVBBQQFKCY-UHFFFAOYSA-N 0.000 claims 1
• IIVNSBQQAJSHHY-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(2-methylimidazol-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound CC1=NC=CN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 IIVNSBQQAJSHHY-UHFFFAOYSA-N 0.000 claims 1
• DFLLILUQHRVESY-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(5-methylsulfonyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1C2CN(S(=O)(=O)C)CC2CN1CC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 DFLLILUQHRVESY-UHFFFAOYSA-N 0.000 claims 1
• ZHZNRUQJXPLVPO-ONEGZZNKSA-N 4-[2-(1h-indazol-4-yl)-6-[(e)-3-methoxyprop-1-enyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(/C=C/COC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 ZHZNRUQJXPLVPO-ONEGZZNKSA-N 0.000 claims 1
• GDVXXRKFYMDOSS-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[1-(4-methylsulfonylpiperazin-1-yl)ethyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1C(C)N1CCN(S(C)(=O)=O)CC1 GDVXXRKFYMDOSS-UHFFFAOYSA-N 0.000 claims 1
• BPRVEWDTGCDGPT-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[2-(4-methylsulfonylpiperazin-1-yl)ethyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CCC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 BPRVEWDTGCDGPT-UHFFFAOYSA-N 0.000 claims 1
• WZEMCHCPNXFMIV-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[2-(4-methylsulfonylpiperazin-1-yl)propan-2-yl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1C(C)(C)N1CCN(S(C)(=O)=O)CC1 WZEMCHCPNXFMIV-UHFFFAOYSA-N 0.000 claims 1
• MKJMAHCPYVPVMP-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[3-(4-methylpiperazin-1-yl)prop-1-ynyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC#CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 MKJMAHCPYVPVMP-UHFFFAOYSA-N 0.000 claims 1
• CTWOVQPATIUQCL-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[3-(morpholin-4-ylmethyl)phenyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=CC=1CN1CCOCC1 CTWOVQPATIUQCL-UHFFFAOYSA-N 0.000 claims 1
• NGVJMWAVEDAYMS-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 NGVJMWAVEDAYMS-UHFFFAOYSA-N 0.000 claims 1
• PRWMGVLMVPVIMK-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[3-[(4-methylsulfonylpiperazin-1-yl)methyl]phenyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 PRWMGVLMVPVIMK-UHFFFAOYSA-N 0.000 claims 1
• XPJGNKLLWVDSJB-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-methylsulfonylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(S(=O)(=O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 XPJGNKLLWVDSJB-UHFFFAOYSA-N 0.000 claims 1
• CSDWDEBIVURUIB-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-methylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 CSDWDEBIVURUIB-UHFFFAOYSA-N 0.000 claims 1
• LINPTOPIXQGUON-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-phenylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1SC(C=1C=CC=CC=1)=C2 LINPTOPIXQGUON-UHFFFAOYSA-N 0.000 claims 1
• OPTQQZDVUHANCK-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-propylsulfonylthieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2SC(S(=O)(=O)CCC)=CC2=C1N1CCOCC1 OPTQQZDVUHANCK-UHFFFAOYSA-N 0.000 claims 1
• KCQUVHOWDIPJMY-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-pyridin-3-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1SC(C=1C=NC=CC=1)=C2 KCQUVHOWDIPJMY-UHFFFAOYSA-N 0.000 claims 1
• ISJSOSWFDBKPKH-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-pyridin-4-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1SC(C=1C=CN=CC=1)=C2 ISJSOSWFDBKPKH-UHFFFAOYSA-N 0.000 claims 1
• GZNWNSWUGCPFDU-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-pyrimidin-5-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1SC(C=1C=NC=NC=1)=C2 GZNWNSWUGCPFDU-UHFFFAOYSA-N 0.000 claims 1
• OMJFVWRGUNMBSO-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-7-methyl-6-(3-methylsulfonylphenyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2C(C)=C(C=3C=C(C=CC=3)S(C)(=O)=O)SC2=C1N1CCOCC1 OMJFVWRGUNMBSO-UHFFFAOYSA-N 0.000 claims 1
• GXJBABITGPOFCK-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1SC=C2 GXJBABITGPOFCK-UHFFFAOYSA-N 0.000 claims 1
• UXVQKIONVNQABP-UHFFFAOYSA-N 4-[2-(1h-indazol-6-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC(C=2C=C3NN=CC3=CC=2)=NC2=C1SC=C2 UXVQKIONVNQABP-UHFFFAOYSA-N 0.000 claims 1
• BRGOZBMFZJEZOD-UHFFFAOYSA-N 4-[2-(1h-indol-4-yl)-6-(2-methylsulfonylethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(CCS(=O)(=O)C)=CC2=NC(C=2C=3C=CNC=3C=CC=2)=NC=1N1CCOCC1 BRGOZBMFZJEZOD-UHFFFAOYSA-N 0.000 claims 1
• BBAJVIVTBPZDOE-UHFFFAOYSA-N 4-[2-(1h-indol-4-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC(C=2C=3C=CNC=3C=CC=2)=NC2=C1SC=C2 BBAJVIVTBPZDOE-UHFFFAOYSA-N 0.000 claims 1
• UAYRLHUHRPLSPY-UHFFFAOYSA-N 4-[2-(1h-indol-5-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC(C=2C=C3C=CNC3=CC=2)=NC2=C1SC=C2 UAYRLHUHRPLSPY-UHFFFAOYSA-N 0.000 claims 1
• FACVJLFKESEKSB-UHFFFAOYSA-N 4-[2-(1h-indol-6-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC(C=2C=C3NC=CC3=CC=2)=NC2=C1SC=C2 FACVJLFKESEKSB-UHFFFAOYSA-N 0.000 claims 1
• KDHQHMPWDHZZED-UHFFFAOYSA-N 4-[2-(2-methylbenzimidazol-1-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound CC1=NC2=CC=CC=C2N1C(N=C1C=CSC1=1)=NC=1N1CCOCC1 KDHQHMPWDHZZED-UHFFFAOYSA-N 0.000 claims 1
• YFVQUSNMBHWKEY-UHFFFAOYSA-N 4-[3-(1h-indazol-4-yl)-6-[2-(4-methylsulfonylpiperazin-1-yl)propyl]-2h-thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(C)(=O)=O)CCN1C(C)CC(SC1=2)=CC1=NCN(C=1C=3C=NNC=3C=CC=1)C=2N1CCOCC1 YFVQUSNMBHWKEY-UHFFFAOYSA-N 0.000 claims 1
• DOYCWLGESOTTIQ-UHFFFAOYSA-N 4-[4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl]-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=C3C=CNC3=NC=2)=C1 DOYCWLGESOTTIQ-UHFFFAOYSA-N 0.000 claims 1
• ZNLQHFWSBQWQAA-UHFFFAOYSA-N 4-[6-(2-fluoropyridin-3-yl)-2-(1h-indazol-4-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound FC1=NC=CC=C1C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 ZNLQHFWSBQWQAA-UHFFFAOYSA-N 0.000 claims 1
• DPTOUGCBGLJTEU-UHFFFAOYSA-N 4-[6-(3,4-dimethoxyphenyl)-2-(1h-indazol-4-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 DPTOUGCBGLJTEU-UHFFFAOYSA-N 0.000 claims 1
• RAJPSTNLUWNLEK-UHFFFAOYSA-N 4-[6-(3-methylsulfonylphenyl)-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC3=NC(=NC(=C3C=2)N2CCOCC2)C=2C=C3C=CNC3=NC=2)=C1 RAJPSTNLUWNLEK-UHFFFAOYSA-N 0.000 claims 1
• WVVVIUYWEYKSBO-UHFFFAOYSA-N 4-[6-(3-methylsulfonylphenyl)-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=C3C=CNC3=NC=2)=C1 WVVVIUYWEYKSBO-UHFFFAOYSA-N 0.000 claims 1
• WJPSFJLYFDPZQL-UHFFFAOYSA-N 4-[6-(6-fluoropyridin-3-yl)-2-(1h-indazol-4-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(F)=CC=C1C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 WJPSFJLYFDPZQL-UHFFFAOYSA-N 0.000 claims 1
• ZRVDTETZMKGCJC-UHFFFAOYSA-N 4-[6-(6-morpholin-4-ylpyridin-3-yl)-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=CC=C(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=C3C=CNC3=NC=2)C=N1 ZRVDTETZMKGCJC-UHFFFAOYSA-N 0.000 claims 1
• ZFXWZPQVEOYLAR-UHFFFAOYSA-N 4-[6-(imidazol-1-ylmethyl)-2-(1h-indazol-4-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=CN=CN1CC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 ZFXWZPQVEOYLAR-UHFFFAOYSA-N 0.000 claims 1
• YVXPBURFHIOTBL-UHFFFAOYSA-N 4-[6-chloro-2-(1h-indazol-4-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(Cl)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 YVXPBURFHIOTBL-UHFFFAOYSA-N 0.000 claims 1
• XCYRTOCPTYYHAF-UHFFFAOYSA-N 4-[6-phenyl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC(C=2C=C3C=CNC3=NC=2)=NC2=C1SC(C=1C=CC=CC=1)=C2 XCYRTOCPTYYHAF-UHFFFAOYSA-N 0.000 claims 1
• MREAPSSQNXBNMY-UHFFFAOYSA-N 4-[7-methyl-2-(2-methyl-1h-imidazo[4,5-b]pyridin-6-yl)-6-(3-methylsulfonylphenyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1N=C2NC(C)=NC2=CC=1C(N=C1C(C)=C(SC1=1)C=2C=C(C=CC=2)S(C)(=O)=O)=NC=1N1CCOCC1 MREAPSSQNXBNMY-UHFFFAOYSA-N 0.000 claims 1
• CFPVHCXCHOSYFZ-UHFFFAOYSA-N 4-[7-methyl-6-(3-methylsulfonylphenyl)-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound N1=C(C=2C=C3C=CNC3=NC=2)N=C2C(C)=C(C=3C=C(C=CC=3)S(C)(=O)=O)SC2=C1N1CCOCC1 CFPVHCXCHOSYFZ-UHFFFAOYSA-N 0.000 claims 1
• TZHQPMLOFDDRBR-UHFFFAOYSA-N 4-[7-methyl-6-phenyl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound N1=C(C=2C=C3C=CNC3=NC=2)N=C2C(C)=C(C=3C=CC=CC=3)SC2=C1N1CCOCC1 TZHQPMLOFDDRBR-UHFFFAOYSA-N 0.000 claims 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
• KPHKNRARMUEJAE-UHFFFAOYSA-N 5-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-methylpyridine-3-carboxamide Chemical compound CNC(=O)C1=CN=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 KPHKNRARMUEJAE-UHFFFAOYSA-N 0.000 claims 1
• ITOUAJPKDVQNOM-UHFFFAOYSA-N 5-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 ITOUAJPKDVQNOM-UHFFFAOYSA-N 0.000 claims 1
• DRBYPXKWMNCJND-UHFFFAOYSA-N 5-[7-methyl-4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl]-n-(2-morpholin-4-ylethyl)pyridin-2-amine Chemical compound N1=C(C=2C=C3C=CNC3=NC=2)N=C2C(C)=C(C=3C=NC(NCCN4CCOCC4)=CC=3)SC2=C1N1CCOCC1 DRBYPXKWMNCJND-UHFFFAOYSA-N 0.000 claims 1
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• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims 1
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims 1
• 239000004146 Propane-1,2-diol Substances 0.000 claims 1
• 102000001253 Protein Kinase Human genes 0.000 claims 1
• CGDNBRSICATCCM-UHFFFAOYSA-N [1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]sulfonylpiperidin-2-yl]methanol Chemical compound OCC1CCCCN1S(=O)(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 CGDNBRSICATCCM-UHFFFAOYSA-N 0.000 claims 1
• LOLXTZFSJNCISR-UHFFFAOYSA-N [1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]sulfonylpiperidin-3-yl]methanol Chemical compound C1C(CO)CCCN1S(=O)(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 LOLXTZFSJNCISR-UHFFFAOYSA-N 0.000 claims 1
• XVOPDJREVPGIQS-UHFFFAOYSA-N [1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]sulfonylpiperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1S(=O)(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 XVOPDJREVPGIQS-UHFFFAOYSA-N 0.000 claims 1
• ZCIUQVOMAJPLDW-UHFFFAOYSA-N [2-(1h-indazol-4-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidin-6-yl]-(4-methylsulfonylpiperazin-1-yl)methanone Chemical compound C1CN(S(=O)(=O)C)CCN1C(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2O1 ZCIUQVOMAJPLDW-UHFFFAOYSA-N 0.000 claims 1
• OGOFABAHCDUSAR-UHFFFAOYSA-N [2-(1h-indazol-4-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidin-6-yl]methanol Chemical compound C=12OC(CO)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 OGOFABAHCDUSAR-UHFFFAOYSA-N 0.000 claims 1
• MSHJILGQTIPLTK-UHFFFAOYSA-N [2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 MSHJILGQTIPLTK-UHFFFAOYSA-N 0.000 claims 1
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• DXLJYJMTRJPOMK-UHFFFAOYSA-N [2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 DXLJYJMTRJPOMK-UHFFFAOYSA-N 0.000 claims 1
• SMRKCXPZXJWDQL-UHFFFAOYSA-N [2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-(4-methylsulfanylphenyl)methanol Chemical compound C1=CC(SC)=CC=C1C(O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 SMRKCXPZXJWDQL-UHFFFAOYSA-N 0.000 claims 1
• FYJKODWVFKPWDM-UHFFFAOYSA-N [2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-(4-methylsulfonylphenyl)methanol Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 FYJKODWVFKPWDM-UHFFFAOYSA-N 0.000 claims 1
• NAHOMCUIZWCREX-UHFFFAOYSA-N [2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-(4-methylsulfonylpiperazin-1-yl)methanone Chemical compound C1CN(S(=O)(=O)C)CCN1C(=O)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 NAHOMCUIZWCREX-UHFFFAOYSA-N 0.000 claims 1
• XQQQHUIJLNSUDW-UHFFFAOYSA-N [2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1C(=O)N(CC1)CCC1N1CCCC1 XQQQHUIJLNSUDW-UHFFFAOYSA-N 0.000 claims 1
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• JUZFJHWWBIFJDN-UHFFFAOYSA-N [3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 JUZFJHWWBIFJDN-UHFFFAOYSA-N 0.000 claims 1
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• 239000002671 adjuvant Substances 0.000 claims 1
• 150000001412 amines Chemical class 0.000 claims 1
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• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
• 230000005764 inhibitory process Effects 0.000 claims 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
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• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
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• ZOPSPVOZYWKCJS-UHFFFAOYSA-N n-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]acetamide Chemical compound C=12SC(NC(=O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 ZOPSPVOZYWKCJS-UHFFFAOYSA-N 0.000 claims 1
• QNLNTELZALDRKM-UHFFFAOYSA-N n-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 QNLNTELZALDRKM-UHFFFAOYSA-N 0.000 claims 1
• HKAOBTGSVCUELW-UHFFFAOYSA-N n-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propanamide Chemical compound C=12SC(NC(=O)CC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 HKAOBTGSVCUELW-UHFFFAOYSA-N 0.000 claims 1
• HJXHQGHFTGSJOK-UHFFFAOYSA-N n-[2-(dimethylamino)-2-oxoethyl]-2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)NCC(=O)N(C)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 HJXHQGHFTGSJOK-UHFFFAOYSA-N 0.000 claims 1
• HLYXPODSMFLKJN-UHFFFAOYSA-N n-[2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 HLYXPODSMFLKJN-UHFFFAOYSA-N 0.000 claims 1
• JXRMAJJAKSGZET-UHFFFAOYSA-N n-[2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-yl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC(C)(C)C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 JXRMAJJAKSGZET-UHFFFAOYSA-N 0.000 claims 1
• BMOVDQUGLQDPOV-UHFFFAOYSA-N n-[2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-yl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC(C)(C)C1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 BMOVDQUGLQDPOV-UHFFFAOYSA-N 0.000 claims 1
• ZTRKBTZJFRRCAS-UHFFFAOYSA-N n-[2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-yl]acetamide Chemical compound C=12SC(C(C)(C)NC(=O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 ZTRKBTZJFRRCAS-UHFFFAOYSA-N 0.000 claims 1
• WTYHQVYOZDBNRV-UHFFFAOYSA-N n-[2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-yl]benzamide Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1C(C)(C)NC(=O)C1=CC=CC=C1 WTYHQVYOZDBNRV-UHFFFAOYSA-N 0.000 claims 1
• PUGFDZBXEJEBLD-UHFFFAOYSA-N n-[2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-yl]methanesulfonamide Chemical compound C=12SC(C(C)(NS(C)(=O)=O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 PUGFDZBXEJEBLD-UHFFFAOYSA-N 0.000 claims 1
• KZXRGXVPZJQWHC-UHFFFAOYSA-N n-[2-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-yl]pyridine-3-carboxamide Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1C(C)(C)NC(=O)C1=CC=CN=C1 KZXRGXVPZJQWHC-UHFFFAOYSA-N 0.000 claims 1
• DTMFFSITJJNBIH-UHFFFAOYSA-N n-[3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidin-6-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2OC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 DTMFFSITJJNBIH-UHFFFAOYSA-N 0.000 claims 1
• WNSMZRZEYUEEOQ-UHFFFAOYSA-N n-[3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidin-6-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2OC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 WNSMZRZEYUEEOQ-UHFFFAOYSA-N 0.000 claims 1
• NLVSATOETWMLEB-UHFFFAOYSA-N n-[3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2SC3=NC(=NC(=C3C=2)N2CCOCC2)C=2C=3C=NNC=3C=CC=2)=C1 NLVSATOETWMLEB-UHFFFAOYSA-N 0.000 claims 1
• IOFPTEMGEPNPAI-UHFFFAOYSA-N n-[3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-2-methoxyacetamide Chemical compound COCC(=O)NC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 IOFPTEMGEPNPAI-UHFFFAOYSA-N 0.000 claims 1
• OEAFFLWWBWLOPU-UHFFFAOYSA-N n-[3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-n-methylacetamide Chemical compound CC(=O)N(C)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 OEAFFLWWBWLOPU-UHFFFAOYSA-N 0.000 claims 1
• ZVHZSNKNTKEEHU-UHFFFAOYSA-N n-[3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 ZVHZSNKNTKEEHU-UHFFFAOYSA-N 0.000 claims 1
• YYTJHTLEZIMJSV-UHFFFAOYSA-N n-[3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 YYTJHTLEZIMJSV-UHFFFAOYSA-N 0.000 claims 1
• OBHTYXZOTKNGQZ-UHFFFAOYSA-N n-[3-[2-(1h-indazol-4-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=3C=NNC=3C=CC=2)C)=C1 OBHTYXZOTKNGQZ-UHFFFAOYSA-N 0.000 claims 1
• TYKDMCBSMADXCT-UHFFFAOYSA-N n-[3-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methylamino]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(NCC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 TYKDMCBSMADXCT-UHFFFAOYSA-N 0.000 claims 1
• XHHQPDIIKLSWGG-UHFFFAOYSA-N n-[3-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methylamino]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(NCC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 XHHQPDIIKLSWGG-UHFFFAOYSA-N 0.000 claims 1
• YEKCIGIILJVPAN-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]-n-methylacetamide Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2SC(CN(C)C(C)=O)=CC2=C1N1CCOCC1 YEKCIGIILJVPAN-UHFFFAOYSA-N 0.000 claims 1
• GWFIJUKVPLESNQ-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-1-(3-methoxyphenyl)-n-methylmethanamine Chemical compound COC1=CC=CC(CN(C)CC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 GWFIJUKVPLESNQ-UHFFFAOYSA-N 0.000 claims 1
• WQYLVVXCKBTNFS-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-1h-pyrazol-5-amine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1CNC1=CC=NN1 WQYLVVXCKBTNFS-UHFFFAOYSA-N 0.000 claims 1
• BRDAIOVATLRXRI-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NCC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 BRDAIOVATLRXRI-UHFFFAOYSA-N 0.000 claims 1
• QEJCCYYDBLSDCO-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-2-(4-methoxyphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NCC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 QEJCCYYDBLSDCO-UHFFFAOYSA-N 0.000 claims 1
• MOTJUNPNVGOULU-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-2-(methanesulfonamido)acetamide Chemical compound C=12SC(CNC(=O)CNS(=O)(=O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 MOTJUNPNVGOULU-UHFFFAOYSA-N 0.000 claims 1
• HDDLCQGWIICNBM-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-2-methoxy-n-(sulfonylmethyl)ethanamine Chemical compound C=12SC(CN(CCOC)C=S(=O)=O)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 HDDLCQGWIICNBM-UHFFFAOYSA-N 0.000 claims 1
• PAFOPKCPMIBOPH-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-2-methoxy-n-methylacetamide Chemical compound C=12SC(CN(C)C(=O)COC)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 PAFOPKCPMIBOPH-UHFFFAOYSA-N 0.000 claims 1
• FOTMTFMUZHDKCF-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-2-methylsulfonylethanamine Chemical compound C=12SC(CNCCS(=O)(=O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 FOTMTFMUZHDKCF-UHFFFAOYSA-N 0.000 claims 1
• SLXPMTGNBXEIBN-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-2-morpholin-4-yl-n-(sulfonylmethyl)ethanamine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1CN(C=S(=O)=O)CCN1CCOCC1 SLXPMTGNBXEIBN-UHFFFAOYSA-N 0.000 claims 1
• BSLKSUJKWSCGQO-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 BSLKSUJKWSCGQO-UHFFFAOYSA-N 0.000 claims 1
• VHCHGAHSRJZYKY-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-3-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=CC(NCC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 VHCHGAHSRJZYKY-UHFFFAOYSA-N 0.000 claims 1
• JSLZFIHIJSRJNR-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-3-methylsulfonylpropan-1-amine Chemical compound C=12SC(CNCCCS(=O)(=O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 JSLZFIHIJSRJNR-UHFFFAOYSA-N 0.000 claims 1
• CXLVQGATPPPJKZ-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-4-methoxyaniline Chemical compound C1=CC(OC)=CC=C1NCC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 CXLVQGATPPPJKZ-UHFFFAOYSA-N 0.000 claims 1
• AJOKQLNVCBVCPH-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NCC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 AJOKQLNVCBVCPH-UHFFFAOYSA-N 0.000 claims 1
• YQNJMWSXISDJTL-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-4-morpholin-4-ylaniline Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1CNC(C=C1)=CC=C1N1CCOCC1 YQNJMWSXISDJTL-UHFFFAOYSA-N 0.000 claims 1
• DDNXFUFIIVAIJD-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-6-methoxypyridin-3-amine Chemical compound C1=NC(OC)=CC=C1NCC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 DDNXFUFIIVAIJD-UHFFFAOYSA-N 0.000 claims 1
• CLJFVIIPYSNVBT-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-6-morpholin-4-ylpyridin-3-amine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1CNC(C=N1)=CC=C1N1CCOCC1 CLJFVIIPYSNVBT-UHFFFAOYSA-N 0.000 claims 1
• FNOBKJZAYWXARK-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-(1-methylpyrrolidin-3-yl)methanesulfonamide Chemical compound C1N(C)CCC1N(S(C)(=O)=O)CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 FNOBKJZAYWXARK-UHFFFAOYSA-N 0.000 claims 1
• XEFGTXIRCDZICI-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(C)CC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 XEFGTXIRCDZICI-UHFFFAOYSA-N 0.000 claims 1
• QFLFELVEHGJZRD-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methyl-3-morpholin-4-ylpropane-1-sulfonamide Chemical compound C1COCCN1CCCS(=O)(=O)N(C)CC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 QFLFELVEHGJZRD-UHFFFAOYSA-N 0.000 claims 1
• VGKRNNPCRRTVDX-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylacetamide Chemical compound C=12SC(CN(C)C(C)=O)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 VGKRNNPCRRTVDX-UHFFFAOYSA-N 0.000 claims 1
• VERXNRDKAMESJG-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C)CC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 VERXNRDKAMESJG-UHFFFAOYSA-N 0.000 claims 1
• QWOQOLJMHPKEPG-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylmethanesulfonamide Chemical compound C=12SC(CN(C)S(C)(=O)=O)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 QWOQOLJMHPKEPG-UHFFFAOYSA-N 0.000 claims 1
• GDBWYDAADJKVFR-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]aniline Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1CNC1=CC=CC=C1 GDBWYDAADJKVFR-UHFFFAOYSA-N 0.000 claims 1
• QNVPPKICOLKECD-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]cyclopropanesulfonamide Chemical compound C1CC1S(=O)(=O)NCC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 QNVPPKICOLKECD-UHFFFAOYSA-N 0.000 claims 1
• YGKCZWOYHXKHIM-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]methanesulfonamide Chemical compound C=12SC(CNS(=O)(=O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 YGKCZWOYHXKHIM-UHFFFAOYSA-N 0.000 claims 1
• COLQZMFADBIQIF-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]morpholine-4-carboxamide Chemical compound C1COCCN1C(=O)NCC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 COLQZMFADBIQIF-UHFFFAOYSA-N 0.000 claims 1
• XFFDHPDURJDESH-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]pyridin-3-amine Chemical compound C=1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1CNC1=CC=CN=C1 XFFDHPDURJDESH-UHFFFAOYSA-N 0.000 claims 1
• ZXRVOALNDVUFNX-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)NCC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 ZXRVOALNDVUFNX-UHFFFAOYSA-N 0.000 claims 1
• RLDSTQNQAQESLX-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylacetamide Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2C(C)=C(CN(C)C(C)=O)SC2=C1N1CCOCC1 RLDSTQNQAQESLX-UHFFFAOYSA-N 0.000 claims 1
• UKAWYOAEIQZFEL-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylmethanesulfonamide Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2C(C)=C(CN(C)S(C)(=O)=O)SC2=C1N1CCOCC1 UKAWYOAEIQZFEL-UHFFFAOYSA-N 0.000 claims 1
• JHZWLWGOVYIQKW-UHFFFAOYSA-N n-[[2-(1h-indol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methyl-3-morpholin-4-ylpropane-1-sulfonamide Chemical compound C1COCCN1CCCS(=O)(=O)N(C)CC(SC1=2)=CC1=NC(C=1C=3C=CNC=3C=CC=1)=NC=2N1CCOCC1 JHZWLWGOVYIQKW-UHFFFAOYSA-N 0.000 claims 1
• BDYGRJQKNJPGMF-UHFFFAOYSA-N n-[[2-(1h-indol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylacetamide Chemical compound C=12SC(CN(C)C(C)=O)=CC2=NC(C=2C=3C=CNC=3C=CC=2)=NC=1N1CCOCC1 BDYGRJQKNJPGMF-UHFFFAOYSA-N 0.000 claims 1
• MOTBSPARVVDJOU-UHFFFAOYSA-N n-[[2-(1h-indol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylmethanesulfonamide Chemical compound C=12SC(CN(C)S(C)(=O)=O)=CC2=NC(C=2C=3C=CNC=3C=CC=2)=NC=1N1CCOCC1 MOTBSPARVVDJOU-UHFFFAOYSA-N 0.000 claims 1
• FBKQKZUNVMVVCX-UHFFFAOYSA-N n-[[2-(1h-indol-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylacetamide Chemical compound C=12SC(CN(C)C(C)=O)=CC2=NC(C=2C=C3C=CNC3=CC=2)=NC=1N1CCOCC1 FBKQKZUNVMVVCX-UHFFFAOYSA-N 0.000 claims 1
• CYFAGQCCUKPQGK-UHFFFAOYSA-N n-[[3-[4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl]phenyl]methyl]methanesulfonamide Chemical compound CS(=O)(=O)NCC1=CC=CC(C=2SC3=NC(=NC(=C3C=2)N2CCOCC2)C=2C=C3C=CNC3=NC=2)=C1 CYFAGQCCUKPQGK-UHFFFAOYSA-N 0.000 claims 1
• AABMTFMWGJXKIT-UHFFFAOYSA-N n-[[3-[7-methyl-4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl]phenyl]methyl]methanesulfonamide Chemical compound N1=C(C=2C=C3C=CNC3=NC=2)N=C2C(C)=C(C=3C=C(CNS(C)(=O)=O)C=CC=3)SC2=C1N1CCOCC1 AABMTFMWGJXKIT-UHFFFAOYSA-N 0.000 claims 1
• OHVNLFCAHUKGFE-UHFFFAOYSA-N n-cyclopropyl-2-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methylamino]acetamide Chemical compound C1CC1NC(=O)CNCC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 OHVNLFCAHUKGFE-UHFFFAOYSA-N 0.000 claims 1
• MTJYUWQSOPNLPR-UHFFFAOYSA-N n-ethyl-2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2SC(C(=O)NCC)=CC2=C1N1CCOCC1 MTJYUWQSOPNLPR-UHFFFAOYSA-N 0.000 claims 1
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• JRSPQCFFSWGXFZ-UHFFFAOYSA-N n-ethyl-3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]benzamide Chemical compound CCNC(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 JRSPQCFFSWGXFZ-UHFFFAOYSA-N 0.000 claims 1
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