RU2468027C2 - Ингибиторы фосфоинозитид-3-киназы и способы их применения - Google Patents

Info

Publication number

RU2468027C2

RU2468027C2 RU2009125897/04A RU2009125897A RU2468027C2 RU 2468027 C2 RU2468027 C2 RU 2468027C2 RU 2009125897/04 A RU2009125897/04 A RU 2009125897/04A RU 2009125897 A RU2009125897 A RU 2009125897A RU 2468027 C2 RU2468027 C2 RU 2468027C2

Authority

RU

Russia

Prior art keywords

methyl

pyrimidin

morpholinothieno

amine

morpholino

Prior art date

2006-12-07

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 324
• 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title description 5
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 230
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 45
• 150000003839 salts Chemical class 0.000 claims abstract description 39
• 201000011510 cancer Diseases 0.000 claims abstract description 38
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 26
• 239000002207 metabolite Substances 0.000 claims abstract description 26
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 24
• 239000012453 solvate Substances 0.000 claims abstract description 19
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 19
• 230000000694 effects Effects 0.000 claims abstract description 18
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 17
• 150000002632 lipids Chemical class 0.000 claims abstract description 16
• 108091007960 PI3Ks Proteins 0.000 claims abstract description 13
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 11
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 11
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 11
• 230000001404 mediated effect Effects 0.000 claims abstract description 6
• 102000038030 PI3Ks Human genes 0.000 claims abstract 6
• -1 C 1 - C 6 alkyl Chemical compound 0.000 claims description 233
• 229910052739 hydrogen Inorganic materials 0.000 claims description 100
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 80
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
• 238000011282 treatment Methods 0.000 claims description 39
• 125000000623 heterocyclic group Chemical group 0.000 claims description 37
• 229920006395 saturated elastomer Polymers 0.000 claims description 28
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 27
• 239000003814 drug Substances 0.000 claims description 26
• 239000008194 pharmaceutical composition Substances 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 24
• 241000124008 Mammalia Species 0.000 claims description 21
• 125000000217 alkyl group Chemical group 0.000 claims description 21
• 229910052740 iodine Inorganic materials 0.000 claims description 20
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 20
• 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 description 19
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 229910052801 chlorine Inorganic materials 0.000 claims description 18
• 229910052794 bromium Inorganic materials 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 17
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
• 229910005965 SO 2 Inorganic materials 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 16
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 239000002585 base Substances 0.000 claims description 13
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
• BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 12
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims description 11
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• MUSKXFQCWPMBII-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCNCC2)=C2)C2=N1 MUSKXFQCWPMBII-UHFFFAOYSA-N 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000006413 ring segment Chemical group 0.000 claims description 9
• 230000001225 therapeutic effect Effects 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 6
• AVCJIFBJUREYDX-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCNCC2)=C2)C2=N1 AVCJIFBJUREYDX-UHFFFAOYSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
• OHZLGNYWJIBNQL-UHFFFAOYSA-N 2-[1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperidin-4-yl]sulfonyl-n,n-dimethylacetamide Chemical compound C1CC(S(=O)(=O)CC(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 OHZLGNYWJIBNQL-UHFFFAOYSA-N 0.000 claims description 4
• WQVHGYBGLRAIKN-UHFFFAOYSA-N 4-[2-(2-methylpyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(C)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 WQVHGYBGLRAIKN-UHFFFAOYSA-N 0.000 claims description 4
• KPKGXPGKYSNSLV-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=C(N)N=CC=3)=NC(N3CCOCC3)=C2S1 KPKGXPGKYSNSLV-UHFFFAOYSA-N 0.000 claims description 4
• RRHMAEWUQQZXRW-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridine-2,6-diamine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=C(N)N=C(N)C=3)=NC(N3CCOCC3)=C2S1 RRHMAEWUQQZXRW-UHFFFAOYSA-N 0.000 claims description 4
• SKMIQINGCMDHAW-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[(4-thiophen-2-ylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(=O)(=O)C=2SC=CC=2)S2)C2=N1 SKMIQINGCMDHAW-UHFFFAOYSA-N 0.000 claims description 4
• SQSSIGUUBPZKBQ-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2O1 SQSSIGUUBPZKBQ-UHFFFAOYSA-N 0.000 claims description 4
• JEHTXQHLTKVUGY-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 JEHTXQHLTKVUGY-UHFFFAOYSA-N 0.000 claims description 4
• RZDHSETVTNFKSF-UHFFFAOYSA-N 6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-yl-2-pyrimidin-5-ylfuro[3,2-d]pyrimidine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC=NC=3)=NC(N3CCOCC3)=C2O1 RZDHSETVTNFKSF-UHFFFAOYSA-N 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• XXADJQIXIXWQNZ-UHFFFAOYSA-N n-methyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 XXADJQIXIXWQNZ-UHFFFAOYSA-N 0.000 claims description 4
• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• KFYZNHXSAWBVIE-HOTGVXAUSA-N (2s)-1-[(3s)-4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-3-methylpiperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C[C@H]1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 KFYZNHXSAWBVIE-HOTGVXAUSA-N 0.000 claims description 3
• MGJSBPBSENBWNX-AWEZNQCLSA-N (2s)-1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 MGJSBPBSENBWNX-AWEZNQCLSA-N 0.000 claims description 3
• ZZRLHKDABGJXHM-AWEZNQCLSA-N (2s)-1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 ZZRLHKDABGJXHM-AWEZNQCLSA-N 0.000 claims description 3
• YOVVNQKCSKSHKT-HNNXBMFYSA-N (2s)-1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 YOVVNQKCSKSHKT-HNNXBMFYSA-N 0.000 claims description 3
• GDAOFGJPAWFAOG-HNNXBMFYSA-N (2s)-1-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2S1 GDAOFGJPAWFAOG-HNNXBMFYSA-N 0.000 claims description 3
• LKGXACWDLPJKHG-HNNXBMFYSA-N (2s)-1-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 LKGXACWDLPJKHG-HNNXBMFYSA-N 0.000 claims description 3
• FJDJDYQNCUOLSQ-INIZCTEOSA-N (2s)-1-[4-[[2-(6-aminopyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 FJDJDYQNCUOLSQ-INIZCTEOSA-N 0.000 claims description 3
• ULXAHCRHGKOQFJ-AWEZNQCLSA-N (2s)-2-amino-1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](N)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 ULXAHCRHGKOQFJ-AWEZNQCLSA-N 0.000 claims description 3
• NZXUDOZLBWGVLI-KRWDZBQOSA-N (2s)-2-hydroxy-1-[4-[(7-methyl-4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2S1 NZXUDOZLBWGVLI-KRWDZBQOSA-N 0.000 claims description 3
• IGMLEPWZACCRCX-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[(7-methyl-4-morpholin-4-yl-2-pyrimidin-5-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC=NC=3)=NC(N3CCOCC3)=C2S1 IGMLEPWZACCRCX-INIZCTEOSA-N 0.000 claims description 3
• SQLXGVDEYHYONY-HNNXBMFYSA-N (2s)-2-hydroxy-1-[4-[[2-(2-methoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)[C@H](C)O)=C2)C2=N1 SQLXGVDEYHYONY-HNNXBMFYSA-N 0.000 claims description 3
• WTTHUCMKPFJUBB-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[[2-(2-methoxypyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)[C@H](C)O)=C2C)C2=N1 WTTHUCMKPFJUBB-INIZCTEOSA-N 0.000 claims description 3
• RDDMDXOXILPHJV-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[[2-(6-methoxypyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(OC)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)[C@H](C)O)=C2)C2=N1 RDDMDXOXILPHJV-INIZCTEOSA-N 0.000 claims description 3
• KNPOYYSMPUNDRT-KRWDZBQOSA-N (2s)-2-hydroxy-1-[4-[[2-(6-methoxypyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(OC)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)[C@H](C)O)=C2C)C2=N1 KNPOYYSMPUNDRT-KRWDZBQOSA-N 0.000 claims description 3
• XIWKCPGWKOFCFH-CQSZACIVSA-N (3r)-1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperidin-3-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2C[C@H](O)CCC2)=C2)C2=N1 XIWKCPGWKOFCFH-CQSZACIVSA-N 0.000 claims description 3
• QVOSHIFBEUZNLN-CYBMUJFWSA-N (3r)-1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]pyrrolidin-3-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2C[C@H](O)CC2)=C2)C2=N1 QVOSHIFBEUZNLN-CYBMUJFWSA-N 0.000 claims description 3
• RIYQFVAOFLPASA-UHFFFAOYSA-N 1-[(4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2S1 RIYQFVAOFLPASA-UHFFFAOYSA-N 0.000 claims description 3
• CEZYORZQHDIFJJ-UHFFFAOYSA-N 1-[2-(6-aminopyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-methyl-n'-(1-methylpiperidin-4-yl)methanediamine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2C(C)=C1C(NC)NC1CCN(C)CC1 CEZYORZQHDIFJJ-UHFFFAOYSA-N 0.000 claims description 3
• PLIAPZHBJWSKGH-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)C(=O)CO)S2)C2=N1 PLIAPZHBJWSKGH-UHFFFAOYSA-N 0.000 claims description 3
• GTVUTNRKYBQWNW-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 GTVUTNRKYBQWNW-UHFFFAOYSA-N 0.000 claims description 3
• MRNJOYWRCWTXIR-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxy-2-methylpropan-1-one Chemical compound C1CN(C(=O)C(C)(O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 MRNJOYWRCWTXIR-UHFFFAOYSA-N 0.000 claims description 3
• HCSQBCGHQKUDMP-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methylsulfonylethanone Chemical compound C1CN(C(=O)CS(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 HCSQBCGHQKUDMP-UHFFFAOYSA-N 0.000 claims description 3
• QAXRQZQJYVJBCH-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2C(C)=C1CN1CCN(C(=O)CO)CC1 QAXRQZQJYVJBCH-UHFFFAOYSA-N 0.000 claims description 3
• JAJIGEGBWOJVTR-UHFFFAOYSA-N 1-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)C(=O)CO)S2)C2=N1 JAJIGEGBWOJVTR-UHFFFAOYSA-N 0.000 claims description 3
• YPFFPBKNPHCNIF-UHFFFAOYSA-N 1-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)CO)=C2)C2=N1 YPFFPBKNPHCNIF-UHFFFAOYSA-N 0.000 claims description 3
• WXVYOOBGBIIUOI-UHFFFAOYSA-N 1-[4-[[2-(6-aminopyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2C(C)=C1CN1CCN(C(=O)CO)CC1 WXVYOOBGBIIUOI-UHFFFAOYSA-N 0.000 claims description 3
• ZYSOOUVFIHTRPL-UHFFFAOYSA-N 1-[[2-(2,4-dimethoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1CC1=CC2=NC(C=3C(=NC(OC)=NC=3)OC)=NC(N3CCOCC3)=C2S1 ZYSOOUVFIHTRPL-UHFFFAOYSA-N 0.000 claims description 3
• HBNUHUVUGYDLJB-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-4-(4-chlorophenyl)piperidin-4-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(O)(CC2)C=2C=CC(Cl)=CC=2)=C2)C2=N1 HBNUHUVUGYDLJB-UHFFFAOYSA-N 0.000 claims description 3
• SIDYNERHAYWAOY-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 SIDYNERHAYWAOY-UHFFFAOYSA-N 0.000 claims description 3
• AXPOMZYFYHYHGM-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 AXPOMZYFYHYHGM-UHFFFAOYSA-N 0.000 claims description 3
• IJOCIJHNWGYUGQ-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperidin-4-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(O)CC2)=C2)C2=N1 IJOCIJHNWGYUGQ-UHFFFAOYSA-N 0.000 claims description 3
• LJKAYKGKAQGNPE-UHFFFAOYSA-N 1-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 LJKAYKGKAQGNPE-UHFFFAOYSA-N 0.000 claims description 3
• FCXXOULHNFAWKH-UHFFFAOYSA-N 1-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 FCXXOULHNFAWKH-UHFFFAOYSA-N 0.000 claims description 3
• NLPRUSAMPUFZQG-UHFFFAOYSA-N 2-(2-methoxypyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(OC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 NLPRUSAMPUFZQG-UHFFFAOYSA-N 0.000 claims description 3
• HGWXCIFBYQHGBF-UHFFFAOYSA-N 2-(5-methoxypyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound COC1=CN=CC(C=2N=C3C=C(CN4CCN(CC4)S(C)(=O)=O)OC3=C(N3CCOCC3)N=2)=C1 HGWXCIFBYQHGBF-UHFFFAOYSA-N 0.000 claims description 3
• LWYDLVVUGDVCAV-UHFFFAOYSA-N 2-[1-[(4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1CC1=CC2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2S1 LWYDLVVUGDVCAV-UHFFFAOYSA-N 0.000 claims description 3
• MRHDCTNTTCVSRM-UHFFFAOYSA-N 2-[1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperidin-4-yl]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CCO)CC2)=C2)C2=N1 MRHDCTNTTCVSRM-UHFFFAOYSA-N 0.000 claims description 3
• ULZSSABCROOAPR-UHFFFAOYSA-N 2-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-n,2-dimethylpropanamide Chemical compound C1CN(C(C)(C)C(=O)NC)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 ULZSSABCROOAPR-UHFFFAOYSA-N 0.000 claims description 3
• UARUXLCKYYGGRR-UHFFFAOYSA-N 2-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-n,n-dimethylacetamide Chemical compound C1CN(CC(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 UARUXLCKYYGGRR-UHFFFAOYSA-N 0.000 claims description 3
• WZLIWPAFBLTQAC-UHFFFAOYSA-N 2-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CCO)CC2)=C2)C2=N1 WZLIWPAFBLTQAC-UHFFFAOYSA-N 0.000 claims description 3
• OIUAUQDHOHXBMJ-UHFFFAOYSA-N 2-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-n,2-dimethylpropanamide Chemical compound C1CN(C(C)(C)C(=O)NC)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 OIUAUQDHOHXBMJ-UHFFFAOYSA-N 0.000 claims description 3
• UZYHCKYMPAEGBW-UHFFFAOYSA-N 2-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-n,n-dimethylacetamide Chemical compound C1CN(CC(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 UZYHCKYMPAEGBW-UHFFFAOYSA-N 0.000 claims description 3
• JBVDQAPQHIKIKX-UHFFFAOYSA-N 2-[[5-[4-morpholin-4-yl-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl]pyridin-2-yl]amino]ethanol Chemical compound C1=NC(NCCO)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCNCC2)=C2)C2=N1 JBVDQAPQHIKIKX-UHFFFAOYSA-N 0.000 claims description 3
• KEQQXXKVAMIDJA-UHFFFAOYSA-N 2-amino-1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methylpropan-1-one Chemical compound C1CN(C(=O)C(C)(N)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 KEQQXXKVAMIDJA-UHFFFAOYSA-N 0.000 claims description 3
• WPQVRPJKRLJRFD-UHFFFAOYSA-N 2-amino-1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CN)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 WPQVRPJKRLJRFD-UHFFFAOYSA-N 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• GIJHJAVPKRWPOL-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 GIJHJAVPKRWPOL-UHFFFAOYSA-N 0.000 claims description 3
• MVOZNHCFXWOPKC-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 MVOZNHCFXWOPKC-UHFFFAOYSA-N 0.000 claims description 3
• IHMUZMAUSSWGBN-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-6-[(4-methylsulfonylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)S(C)(=O)=O)=C2)C2=N1 IHMUZMAUSSWGBN-UHFFFAOYSA-N 0.000 claims description 3
• RMWGJAFXJZVMMY-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-6-[(4-piperidin-1-ylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)N2CCCCC2)=C2)C2=N1 RMWGJAFXJZVMMY-UHFFFAOYSA-N 0.000 claims description 3
• SMUWUMKBYKUINP-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-7-methyl-6-[(4-methylsulfonylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)S(C)(=O)=O)=C2C)C2=N1 SMUWUMKBYKUINP-UHFFFAOYSA-N 0.000 claims description 3
• PJVOYUWADIMQGS-UHFFFAOYSA-N 4-[2-(2-methoxypyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 PJVOYUWADIMQGS-UHFFFAOYSA-N 0.000 claims description 3
• ROBOHVCWTXKHPA-UHFFFAOYSA-N 4-[2-(4-methoxypyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 ROBOHVCWTXKHPA-UHFFFAOYSA-N 0.000 claims description 3
• ZQNSBNNBKUAHQY-UHFFFAOYSA-N 4-[2-(5-methoxypyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CN=CC(C=2N=C3SC(CN4CCN(CC4)S(C)(=O)=O)=CC3=C(N3CCOCC3)N=2)=C1 ZQNSBNNBKUAHQY-UHFFFAOYSA-N 0.000 claims description 3
• FQBRBHJXPDPTMX-UHFFFAOYSA-N 4-[2-(5-methoxypyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CN=CC(C=2N=C3C=C(CN4CCN(CC4)S(C)(=O)=O)SC3=C(N3CCOCC3)N=2)=C1 FQBRBHJXPDPTMX-UHFFFAOYSA-N 0.000 claims description 3
• PQPDIEJGAJTKCA-UHFFFAOYSA-N 4-[2-(6-methoxypyridin-3-yl)-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(OC)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCNCC2)=C2)C2=N1 PQPDIEJGAJTKCA-UHFFFAOYSA-N 0.000 claims description 3
• VUVVTPJFRGJXNC-UHFFFAOYSA-N 4-[2-(6-methylpyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(C)=CC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 VUVVTPJFRGJXNC-UHFFFAOYSA-N 0.000 claims description 3
• IQFSJRGDAKCWRU-UHFFFAOYSA-N 4-[2-(6-methylpyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(C)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 IQFSJRGDAKCWRU-UHFFFAOYSA-N 0.000 claims description 3
• NJTGIYXYNQGPGK-UHFFFAOYSA-N 4-[2-(6-methylpyridin-3-yl)-6-[(4-piperidin-1-ylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(C)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)N2CCCCC2)=C2)C2=N1 NJTGIYXYNQGPGK-UHFFFAOYSA-N 0.000 claims description 3
• NUSKUCOIXWODFL-UHFFFAOYSA-N 4-[2-(furan-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C3=COC=C3)=NC(N3CCOCC3)=C2S1 NUSKUCOIXWODFL-UHFFFAOYSA-N 0.000 claims description 3
• HCNVPRLUBQHBEE-UHFFFAOYSA-N 4-[2-pyridin-3-yl-6-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2SC=1CN(CC1)CCC1N1CCCC1 HCNVPRLUBQHBEE-UHFFFAOYSA-N 0.000 claims description 3
• JJCBDPDTQFUJRN-UHFFFAOYSA-N 4-[6-(piperazin-1-ylmethyl)-2-(2-propan-2-ylimidazol-1-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound CC(C)C1=NC=CN1C1=NC(N2CCOCC2)=C(SC(CN2CCNCC2)=C2)C2=N1 JJCBDPDTQFUJRN-UHFFFAOYSA-N 0.000 claims description 3
• WNSHWFIWDBSVRK-UHFFFAOYSA-N 4-[6-[(3-methylsulfonylpyrrolidin-1-yl)methyl]-2-pyridin-3-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1C(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2S1 WNSHWFIWDBSVRK-UHFFFAOYSA-N 0.000 claims description 3
• UTMALWLPHKIDJL-UHFFFAOYSA-N 4-[6-[(4-cyclopropylsulfonylpiperazin-1-yl)methyl]-2-(2,4-dimethoxypyrimidin-5-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C2CC2)=C2)C2=N1 UTMALWLPHKIDJL-UHFFFAOYSA-N 0.000 claims description 3
• PHKGASRBZCIRNM-UHFFFAOYSA-N 4-[6-[(4-methylpiperazin-1-yl)methyl]-2-pyridin-3-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC1=CC2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2S1 PHKGASRBZCIRNM-UHFFFAOYSA-N 0.000 claims description 3
• HMAZVRLQZNSGFG-UHFFFAOYSA-N 4-[6-[(4-methylpiperazin-1-yl)methyl]-2-pyrimidin-5-ylthieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC=NC=3)N=C2S1 HMAZVRLQZNSGFG-UHFFFAOYSA-N 0.000 claims description 3
• MVKHQXRMYFALFZ-UHFFFAOYSA-N 4-[6-[(4-methylpiperazin-1-yl)methyl]-2-pyrimidin-5-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC1=CC2=NC(C=3C=NC=NC=3)=NC(N3CCOCC3)=C2S1 MVKHQXRMYFALFZ-UHFFFAOYSA-N 0.000 claims description 3
• GFHJARDRYPZJCJ-UHFFFAOYSA-N 4-[6-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]-2-(2,4-dimethoxypyrimidin-5-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C=2C=CC=CC=2)=C2)C2=N1 GFHJARDRYPZJCJ-UHFFFAOYSA-N 0.000 claims description 3
• JPZXRQGJYOJDFA-UHFFFAOYSA-N 4-[7-methyl-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-pyridin-3-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC=CC=3)N=C2C(C)=C1CN1CCN(S(C)(=O)=O)CC1 JPZXRQGJYOJDFA-UHFFFAOYSA-N 0.000 claims description 3
• VXLUOMZPIYNTSE-UHFFFAOYSA-N 4-[[2-(2,4-dimethoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)N(C)C)=C2)C2=N1 VXLUOMZPIYNTSE-UHFFFAOYSA-N 0.000 claims description 3
• QCHQMXYRZYEEFG-UHFFFAOYSA-N 4-[[2-(2,4-dimethoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-sulfonamide Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)N(C)C)=C2)C2=N1 QCHQMXYRZYEEFG-UHFFFAOYSA-N 0.000 claims description 3
• QUHQRCBLMCILHT-UHFFFAOYSA-N 4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 QUHQRCBLMCILHT-UHFFFAOYSA-N 0.000 claims description 3
• KVUGKSFPGCRSDK-UHFFFAOYSA-N 4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-sulfonamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 KVUGKSFPGCRSDK-UHFFFAOYSA-N 0.000 claims description 3
• OEZDMRPXEPUYML-UHFFFAOYSA-N 4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CC1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 OEZDMRPXEPUYML-UHFFFAOYSA-N 0.000 claims description 3
• UKRUOQNFXYOKIM-UHFFFAOYSA-N 4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 UKRUOQNFXYOKIM-UHFFFAOYSA-N 0.000 claims description 3
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• RXPGTCGBAIHVGH-UHFFFAOYSA-N 4-[2-(5-methylpyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=CN=CC(C=2N=C3SC(CN4CCN(CC4)S(C)(=O)=O)=CC3=C(N3CCOCC3)N=2)=C1 RXPGTCGBAIHVGH-UHFFFAOYSA-N 0.000 claims description 2
• AIIRVAMJYVIOSH-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-(5-phenylpyridin-3-yl)thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=C(C=NC=3)C=3C=CC=CC=3)N=C2S1 AIIRVAMJYVIOSH-UHFFFAOYSA-N 0.000 claims description 2
• JAKBHHSTZDBLEK-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-(6-phenylpyridin-3-yl)thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(=CC=3)C=3C=CC=CC=3)N=C2S1 JAKBHHSTZDBLEK-UHFFFAOYSA-N 0.000 claims description 2
• MYQJAHDGCGXUSC-UHFFFAOYSA-N 4-[7-methyl-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-pyrimidin-5-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC=NC=3)N=C2C(C)=C1CN1CCN(S(C)(=O)=O)CC1 MYQJAHDGCGXUSC-UHFFFAOYSA-N 0.000 claims description 2
• RGMUGYGAAFQRTP-UHFFFAOYSA-N 4-methoxy-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 RGMUGYGAAFQRTP-UHFFFAOYSA-N 0.000 claims description 2
• BBUYLOWGHXSUAL-UHFFFAOYSA-N 4-methyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound CC1=CC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 BBUYLOWGHXSUAL-UHFFFAOYSA-N 0.000 claims description 2
• XAZDYPNMXGDMSA-UHFFFAOYSA-N 4-methyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound CC1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 XAZDYPNMXGDMSA-UHFFFAOYSA-N 0.000 claims description 2
• DLXNRTLGDLCEIM-AWEZNQCLSA-N 5-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(N)=NC=2)=NC2=C1SC(CN1CCN(CC1)S(C)(=O)=O)=C2 DLXNRTLGDLCEIM-AWEZNQCLSA-N 0.000 claims description 2
• MYVFDCQGKGXZCT-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[(4-morpholin-4-ylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)N2CCOCC2)=C2)C2=N1 MYVFDCQGKGXZCT-UHFFFAOYSA-N 0.000 claims description 2
• HAKHICFQWUJUER-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[(4-piperidin-1-ylpiperidin-1-yl)methyl]thieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCC(CC2)N2CCCCC2)S2)C2=N1 HAKHICFQWUJUER-UHFFFAOYSA-N 0.000 claims description 2
• GLTYAIKNDHECEG-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[[4-(morpholin-4-ylmethyl)piperidin-1-yl]methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CN3CCOCC3)CC2)=C2)C2=N1 GLTYAIKNDHECEG-UHFFFAOYSA-N 0.000 claims description 2
• LONYAZSIXKELDN-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[[4-(piperidin-1-ylmethyl)piperidin-1-yl]methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CN3CCCCC3)CC2)=C2)C2=N1 LONYAZSIXKELDN-UHFFFAOYSA-N 0.000 claims description 2
• VATXPWUSMHYFAO-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CN3CCCC3)CC2)=C2)C2=N1 VATXPWUSMHYFAO-UHFFFAOYSA-N 0.000 claims description 2
• XAKDBNRKMHTIQJ-UHFFFAOYSA-N 5-[6-[(3-methylsulfonylpyrrolidin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1C(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 XAKDBNRKMHTIQJ-UHFFFAOYSA-N 0.000 claims description 2
• AGAMOTDTIREVOD-UHFFFAOYSA-N 5-[6-[(4-aminopiperidin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(N)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 AGAMOTDTIREVOD-UHFFFAOYSA-N 0.000 claims description 2
• BENDHOSIDINEPF-UHFFFAOYSA-N 5-[6-[(4-ethylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)CC)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 BENDHOSIDINEPF-UHFFFAOYSA-N 0.000 claims description 2
• QNAXBDCTZPSFNK-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]-3-nitropyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=C(C(N)=NC=3)[N+]([O-])=O)N=C2S1 QNAXBDCTZPSFNK-UHFFFAOYSA-N 0.000 claims description 2
• GKYHFVUKIYFTPC-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C(=NC(N)=NC=3)C(F)(F)F)N=C2S1 GKYHFVUKIYFTPC-UHFFFAOYSA-N 0.000 claims description 2
• XIOIAXABIAUOGX-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]-n-propan-2-ylpyrimidin-2-amine Chemical compound C1=NC(NC(C)C)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 XIOIAXABIAUOGX-UHFFFAOYSA-N 0.000 claims description 2
• YIWVVQLJSFLOHM-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-3-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=C(N)C=NC=3)N=C2S1 YIWVVQLJSFLOHM-UHFFFAOYSA-N 0.000 claims description 2
• PPCQFSHMYVOBGA-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C(=NC(N)=NC=3)C(F)(F)F)=NC(N3CCOCC3)=C2S1 PPCQFSHMYVOBGA-UHFFFAOYSA-N 0.000 claims description 2
• ARWPKQOWZCGWIH-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]-n-propan-2-ylpyrimidin-2-amine Chemical compound C1=NC(NC(C)C)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 ARWPKQOWZCGWIH-UHFFFAOYSA-N 0.000 claims description 2
• QJGPVKUDSVMVMX-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridine-2-carbonitrile Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(=CC=3)C#N)=NC(N3CCOCC3)=C2S1 QJGPVKUDSVMVMX-UHFFFAOYSA-N 0.000 claims description 2
• KLXMMRLIIXNDSN-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperidin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 KLXMMRLIIXNDSN-UHFFFAOYSA-N 0.000 claims description 2
• LXMMDYVJBRLVMA-UHFFFAOYSA-N 5-[6-[1-(4-methylsulfonylpiperazin-1-yl)ethyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C=1C2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2SC=1C(C)N1CCN(S(C)(=O)=O)CC1 LXMMDYVJBRLVMA-UHFFFAOYSA-N 0.000 claims description 2
• MSQKBCBWQOJOOP-UHFFFAOYSA-N 5-[6-[1-(4-methylsulfonylpiperazin-1-yl)ethyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2SC=1C(C)N1CCN(S(C)(=O)=O)CC1 MSQKBCBWQOJOOP-UHFFFAOYSA-N 0.000 claims description 2
• GXUKMJRZDYTFCK-UHFFFAOYSA-N 5-[6-[[(1-cyclohexylpiperidin-4-yl)-methylamino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C2CCCCC2)CCC1N(C)CC(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 GXUKMJRZDYTFCK-UHFFFAOYSA-N 0.000 claims description 2
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• OUIMVIGCCHFMQH-UHFFFAOYSA-N 5-[6-[[(1-ethylpiperidin-4-yl)-methylamino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(CC)CCC1N(C)CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 OUIMVIGCCHFMQH-UHFFFAOYSA-N 0.000 claims description 2
• INKCZPNCPOGEGV-UHFFFAOYSA-N 5-[6-[[(1-methylpiperidin-4-yl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1NCC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 INKCZPNCPOGEGV-UHFFFAOYSA-N 0.000 claims description 2
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• OCGWHYISYLSYHR-UHFFFAOYSA-N 5-[6-[[3-(dimethylamino)pyrrolidin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1C(N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 OCGWHYISYLSYHR-UHFFFAOYSA-N 0.000 claims description 2
• YSDTZSHLIDUVAR-UHFFFAOYSA-N 5-[6-[[4-(1-methylimidazol-4-yl)piperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound CN1C=NC(N2CCN(CC=3SC4=C(N5CCOCC5)N=C(N=C4C=3)C=3C=NC(N)=NC=3)CC2)=C1 YSDTZSHLIDUVAR-UHFFFAOYSA-N 0.000 claims description 2
• HLMPRTQAPWALRQ-UHFFFAOYSA-N 5-[6-[[4-(2-fluorophenyl)sulfonylpiperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C=2C(=CC=CC=2)F)=C2)C2=N1 HLMPRTQAPWALRQ-UHFFFAOYSA-N 0.000 claims description 2
• GBPYWUWBMVSNOW-UHFFFAOYSA-N 5-[6-[[4-(3-fluorophenyl)sulfonylpiperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C=2C=C(F)C=CC=2)=C2)C2=N1 GBPYWUWBMVSNOW-UHFFFAOYSA-N 0.000 claims description 2
• CVDAHJKPBXYZQA-UHFFFAOYSA-N 5-[6-[[4-(4-fluorophenyl)sulfonylpiperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C=2C=CC(F)=CC=2)=C2)C2=N1 CVDAHJKPBXYZQA-UHFFFAOYSA-N 0.000 claims description 2
• KMIUWCIFVPEEGN-UHFFFAOYSA-N 5-[6-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C=2C=CC=CC=2)=C2)C2=N1 KMIUWCIFVPEEGN-UHFFFAOYSA-N 0.000 claims description 2
• IGLWKUBDMFFSTC-UHFFFAOYSA-N 5-[6-[[4-(dimethylamino)piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 IGLWKUBDMFFSTC-UHFFFAOYSA-N 0.000 claims description 2
• NAJCYIQZNNQLCB-UHFFFAOYSA-N 5-[6-[[4-(methylsulfonylmethylsulfonyl)piperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)CS(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 NAJCYIQZNNQLCB-UHFFFAOYSA-N 0.000 claims description 2
• DGLGCGPYLBJRJL-UHFFFAOYSA-N 5-[6-[[4-(methylsulfonylmethylsulfonyl)piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(S(=O)(=O)CS(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 DGLGCGPYLBJRJL-UHFFFAOYSA-N 0.000 claims description 2
• XXXDXUAYTCKDGU-UHFFFAOYSA-N 5-[6-[[4-[(2-methylimidazol-1-yl)methyl]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound CC1=NC=CN1CC1CCN(CC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)CC1 XXXDXUAYTCKDGU-UHFFFAOYSA-N 0.000 claims description 2
• BVYXLHAJABVQID-INIZCTEOSA-N 5-[6-[[4-[(2s)-2-hydroxypropanoyl]piperazin-1-yl]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridine-2-carbonitrile Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(=CC=3)C#N)N=C2S1 BVYXLHAJABVQID-INIZCTEOSA-N 0.000 claims description 2
• GXCDYWNDIOWCQC-KRWDZBQOSA-N 5-[6-[[4-[(2s)-2-hydroxypropanoyl]piperazin-1-yl]methyl]-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridine-2-carbonitrile Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC(=CC=3)C#N)=NC(N3CCOCC3)=C2S1 GXCDYWNDIOWCQC-KRWDZBQOSA-N 0.000 claims description 2
• SLMUEYZNQYLTMG-UHFFFAOYSA-N 5-[6-[[4-[(dimethylamino)methyl]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(CN(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 SLMUEYZNQYLTMG-UHFFFAOYSA-N 0.000 claims description 2
• MGJWLSYXZOXKKR-UHFFFAOYSA-N 5-[6-[[4-[2-methoxyethyl(methyl)amino]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]-n-methylpyridin-2-amine Chemical compound C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCC(CC2)N(C)CCOC)S2)C2=N1 MGJWLSYXZOXKKR-UHFFFAOYSA-N 0.000 claims description 2
• ZOXZHRXUZMKVHK-UHFFFAOYSA-N 5-[6-[[4-[2-methoxyethyl(methyl)amino]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]-n-methylpyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCC(CC2)N(C)CCOC)S2)C2=N1 ZOXZHRXUZMKVHK-UHFFFAOYSA-N 0.000 claims description 2
• XPMGSADFXIYUEJ-UHFFFAOYSA-N 5-[6-[[4-[2-methoxyethyl(methyl)amino]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CC(N(C)CCOC)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2S1 XPMGSADFXIYUEJ-UHFFFAOYSA-N 0.000 claims description 2
• AKCJZNUYQJPJET-UHFFFAOYSA-N 5-[6-[[4-[2-methoxyethyl(methyl)amino]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(N(C)CCOC)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 AKCJZNUYQJPJET-UHFFFAOYSA-N 0.000 claims description 2
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