JP5500990B2 - ホスホイノシチド３−キナーゼ阻害剤化合物及び使用方法 - Google Patents

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Publication number

JP5500990B2

JP5500990B2 JP2009540457A JP2009540457A JP5500990B2 JP 5500990 B2 JP5500990 B2 JP 5500990B2 JP 2009540457 A JP2009540457 A JP 2009540457A JP 2009540457 A JP2009540457 A JP 2009540457A JP 5500990 B2 JP5500990 B2 JP 5500990B2

Authority

JP

Japan

Prior art keywords

pyrimidin

morpholinothieno

methyl

aminopyrimidin

amine

Prior art date

2006-12-07

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 150000001875 compounds Chemical class 0.000 title claims description 221
• 238000000034 method Methods 0.000 title description 346
• 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title description 6
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title description 4
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 243
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 130
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 120
• 125000000623 heterocyclic group Chemical group 0.000 claims description 48
• 125000001072 heteroaryl group Chemical group 0.000 claims description 45
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 43
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 38
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 150000003839 salts Chemical class 0.000 claims description 37
• 229920006395 saturated elastomer Polymers 0.000 claims description 32
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
• 229910052801 chlorine Inorganic materials 0.000 claims description 25
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 24
• 229910052794 bromium Inorganic materials 0.000 claims description 24
• 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 23
• 229910052717 sulfur Inorganic materials 0.000 claims description 23
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 21
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• 229910052740 iodine Inorganic materials 0.000 claims description 21
• 229910005965 SO 2 Inorganic materials 0.000 claims description 19
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 16
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 239000012453 solvate Substances 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 15
• 150000001408 amides Chemical class 0.000 claims description 14
• 125000002950 monocyclic group Chemical group 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000006413 ring segment Chemical group 0.000 claims description 9
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 2-amino-2-methylpropanamide Chemical compound CC(C)(N)C(N)=O ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 0.000 claims description 3
• DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 claims description 3
• TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 claims description 3
• MTEZLAATISORQK-UHFFFAOYSA-N 2-methoxyacetamide Chemical compound COCC(N)=O MTEZLAATISORQK-UHFFFAOYSA-N 0.000 claims description 3
• RWQDFZVVBNKZPT-UHFFFAOYSA-N 4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-1-methylsulfonylpiperidin-4-ol Chemical compound C1CN(S(=O)(=O)C)CCC1(O)C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 RWQDFZVVBNKZPT-UHFFFAOYSA-N 0.000 claims description 3
• YBNQSDUPKCXLNG-UHFFFAOYSA-N 5-(7-methyl-4-morpholin-4-yl-6-pyridin-3-ylthieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine Chemical compound N1=C2C(C)=C(C=3C=NC=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 YBNQSDUPKCXLNG-UHFFFAOYSA-N 0.000 claims description 3
• UYTHAKVOHLAZCM-UHFFFAOYSA-N 5-[6-(3-methylsulfonylphenyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridine-3-carboxylic acid Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=C(C=NC=2)C(O)=O)=C1 UYTHAKVOHLAZCM-UHFFFAOYSA-N 0.000 claims description 3
• SCOVPPMAYFSRJK-UHFFFAOYSA-N 5-[6-(4-amino-3-methoxyphenyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=C(N)C(OC)=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 SCOVPPMAYFSRJK-UHFFFAOYSA-N 0.000 claims description 3
• CFFPPNCBRNOBCN-UHFFFAOYSA-N 5-[6-(4-methoxypyridin-3-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound COC1=CC=NC=C1C1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2O1 CFFPPNCBRNOBCN-UHFFFAOYSA-N 0.000 claims description 3
• NFLGVLMLSOSFNW-UHFFFAOYSA-N 5-[6-(4-methoxypyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound COC1=CC=NC=C1C1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 NFLGVLMLSOSFNW-UHFFFAOYSA-N 0.000 claims description 3
• NNKBIAAIUPHMKS-UHFFFAOYSA-N 5-[6-(6-aminopyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound N1=C2C(C)=C(C=3C=NC(N)=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 NNKBIAAIUPHMKS-UHFFFAOYSA-N 0.000 claims description 3
• STJOVQVARSQWAK-UHFFFAOYSA-N 5-[6-[3-(aminomethyl)phenyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound NCC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 STJOVQVARSQWAK-UHFFFAOYSA-N 0.000 claims description 3
• HUNAILOTCSPBKT-UHFFFAOYSA-N 5-[6-[4-(aminomethyl)phenyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=CC(CN)=CC=C1C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 HUNAILOTCSPBKT-UHFFFAOYSA-N 0.000 claims description 3
• BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• XLSTYVRPNMQFHQ-UHFFFAOYSA-N n-[[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 XLSTYVRPNMQFHQ-UHFFFAOYSA-N 0.000 claims description 3
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
• JQJJPCWBCXAEHJ-UHFFFAOYSA-N 1-[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]ethanol Chemical compound CC(O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 JQJJPCWBCXAEHJ-UHFFFAOYSA-N 0.000 claims description 2
• STZLJNQUXJWZSH-UHFFFAOYSA-N 1-[3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]ethanol Chemical compound CC(O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=CC=2)=C1 STZLJNQUXJWZSH-UHFFFAOYSA-N 0.000 claims description 2
• UNRWRQGQPXBNSP-UHFFFAOYSA-N 1-[3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=CC=2)=C1 UNRWRQGQPXBNSP-UHFFFAOYSA-N 0.000 claims description 2
• JTCOKCJNQAKGFG-UHFFFAOYSA-N 2,6-bis(4-methoxypyridin-3-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound COC1=CC=NC=C1C1=CC2=NC(C=3C(=CC=NC=3)OC)=NC(N3CCOCC3)=C2O1 JTCOKCJNQAKGFG-UHFFFAOYSA-N 0.000 claims description 2
• DKOSYNXVLVSAQW-UHFFFAOYSA-N 2-(2-aminopyrimidin-5-yl)-4-morpholin-4-yl-n-(2-piperidin-1-ylethyl)thieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C(=O)NCCN3CCCCC3)C2=N1 DKOSYNXVLVSAQW-UHFFFAOYSA-N 0.000 claims description 2
• QDMHBTZIRSYKIS-UHFFFAOYSA-N 2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)N)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 QDMHBTZIRSYKIS-UHFFFAOYSA-N 0.000 claims description 2
• JOOOGYUIBUUUHV-UHFFFAOYSA-N 2-(2-aminopyrimidin-5-yl)-n-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)NC)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 JOOOGYUIBUUUHV-UHFFFAOYSA-N 0.000 claims description 2
• FFFANAVQQTZXCK-UHFFFAOYSA-N 2-(4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidin-6-yl)propan-2-amine Chemical compound C=12SC(C(C)(N)C)=CC2=NC(C=2C=NC=CC=2)=NC=1N1CCOCC1 FFFANAVQQTZXCK-UHFFFAOYSA-N 0.000 claims description 2
• HSJNCNFEMKDGPU-UHFFFAOYSA-N 2-(4-morpholin-4-yl-2-pyrimidin-5-ylthieno[2,3-d]pyrimidin-6-yl)propan-2-ol Chemical compound N1=C2SC(C(C)(O)C)=CC2=C(N2CCOCC2)N=C1C1=CN=CN=C1 HSJNCNFEMKDGPU-UHFFFAOYSA-N 0.000 claims description 2
• HRORIHPKVXRWON-UHFFFAOYSA-N 2-(4-morpholin-4-yl-2-pyrimidin-5-ylthieno[3,2-d]pyrimidin-6-yl)propan-2-amine Chemical compound C=12SC(C(C)(N)C)=CC2=NC(C=2C=NC=NC=2)=NC=1N1CCOCC1 HRORIHPKVXRWON-UHFFFAOYSA-N 0.000 claims description 2
• FRCPLRQNRJYJSY-UHFFFAOYSA-N 2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carboxamide Chemical compound C=12SC(C(=O)N)=CC2=NC(C=2C=NC(N)=CC=2)=NC=1N1CCOCC1 FRCPLRQNRJYJSY-UHFFFAOYSA-N 0.000 claims description 2
• SSFOPOHRZSSUQX-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]propan-2-ol Chemical compound N1=C2SC(C(C)(O)C)=CC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 SSFOPOHRZSSUQX-UHFFFAOYSA-N 0.000 claims description 2
• CJBGFSHPSSBVSP-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-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=NC(N)=NC=2)=NC=1N1CCOCC1 CJBGFSHPSSBVSP-UHFFFAOYSA-N 0.000 claims description 2
• WPNRKIVRSBIGDL-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-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=NC(N)=NC=2)=NC=1N1CCOCC1 WPNRKIVRSBIGDL-UHFFFAOYSA-N 0.000 claims description 2
• LEXMMFPAPDGYGZ-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-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=NC(N)=NC=2)=NC=1N1CCOCC1 LEXMMFPAPDGYGZ-UHFFFAOYSA-N 0.000 claims description 2
• LJBFUTAAMCZTJC-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound N1=C2C(C)=C(C(C)(C)O)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 LJBFUTAAMCZTJC-UHFFFAOYSA-N 0.000 claims description 2
• MSWMBTHTDZMWTH-UHFFFAOYSA-N 2-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]propan-2-ol Chemical compound N1=C2SC(C(C)(O)C)=CC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 MSWMBTHTDZMWTH-UHFFFAOYSA-N 0.000 claims description 2
• QZXFDKGGZDXUTC-UHFFFAOYSA-N 2-[2-(6-aminopyridin-3-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=NC(N)=CC=2)=NC=1N1CCOCC1 QZXFDKGGZDXUTC-UHFFFAOYSA-N 0.000 claims description 2
• MUICFZZLNRQLQU-UHFFFAOYSA-N 2-[2-(6-fluoropyridin-3-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=NC(F)=CC=2)=NC=1N1CCOCC1 MUICFZZLNRQLQU-UHFFFAOYSA-N 0.000 claims description 2
• GXYQTVDEWXBDTL-UHFFFAOYSA-N 2-[2-[5-(1-hydroxyethyl)pyridin-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound CC(O)C1=CN=CC(C=2N=C3C=C(SC3=C(N3CCOCC3)N=2)C(C)(C)O)=C1 GXYQTVDEWXBDTL-UHFFFAOYSA-N 0.000 claims description 2
• OCDOXXKPNNLSKA-UHFFFAOYSA-N 2-[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 OCDOXXKPNNLSKA-UHFFFAOYSA-N 0.000 claims description 2
• GZQAGBHJMFWGAA-UHFFFAOYSA-N 2-[3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=CC=2)=C1 GZQAGBHJMFWGAA-UHFFFAOYSA-N 0.000 claims description 2
• QMVQCDUOSQCAST-UHFFFAOYSA-N 2-amino-n-[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]acetamide Chemical compound NCC(=O)NC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 QMVQCDUOSQCAST-UHFFFAOYSA-N 0.000 claims description 2
• GUJQCDKORSVMPO-UHFFFAOYSA-N 2-amino-n-[3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]acetamide Chemical compound NCC(=O)NC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=CC=2)=C1 GUJQCDKORSVMPO-UHFFFAOYSA-N 0.000 claims description 2
• QOTAFYAAQZCGBQ-AWEZNQCLSA-N 3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-[(2s)-2-hydroxypropyl]benzamide Chemical compound C[C@H](O)CNC(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 QOTAFYAAQZCGBQ-AWEZNQCLSA-N 0.000 claims description 2
• NKCIHOYBIIYJHO-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]benzoic acid Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(C=CC=3)C(O)=O)C2=N1 NKCIHOYBIIYJHO-UHFFFAOYSA-N 0.000 claims description 2
• PYVJKVQNKORFPI-HNNXBMFYSA-N 3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-[(2s)-2-hydroxypropyl]benzamide Chemical compound C[C@H](O)CNC(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=CC=2)=C1 PYVJKVQNKORFPI-HNNXBMFYSA-N 0.000 claims description 2
• CGOQFMJDDZEPJM-UHFFFAOYSA-N 3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=CC=2)=C1 CGOQFMJDDZEPJM-UHFFFAOYSA-N 0.000 claims description 2
• WHUXHCLMAXJPPF-UHFFFAOYSA-N 3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]benzoic acid Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(C=CC=3)C(O)=O)C2=N1 WHUXHCLMAXJPPF-UHFFFAOYSA-N 0.000 claims description 2
• QIWFQQFUUHNPMZ-UHFFFAOYSA-N 3-[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]propan-1-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(CCCO)C=CC=3)C2=N1 QIWFQQFUUHNPMZ-UHFFFAOYSA-N 0.000 claims description 2
• CYVGTZYRUFYIBE-UHFFFAOYSA-N 4-[2-(2-methoxypyrimidin-5-yl)-6-(3-methylsulfonylphenyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(C=CC=3)S(C)(=O)=O)C2=N1 CYVGTZYRUFYIBE-UHFFFAOYSA-N 0.000 claims description 2
• BYCJWGUCKYVYNS-UHFFFAOYSA-N 4-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[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=NC(N)=CC=2)=C1 BYCJWGUCKYVYNS-UHFFFAOYSA-N 0.000 claims description 2
• AWOMHHDSQMURJZ-UHFFFAOYSA-N 4-[6-(3-methylsulfonylphenyl)-2-pyridin-3-ylthieno[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=NC=CC=2)=C1 AWOMHHDSQMURJZ-UHFFFAOYSA-N 0.000 claims description 2
• XHSPIZKMGQPENT-UHFFFAOYSA-N 4-[6-(4-methoxypyridin-3-yl)-2-pyrimidin-5-ylthieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=NC=C1C1=CC2=C(N3CCOCC3)N=C(C=3C=NC=NC=3)N=C2S1 XHSPIZKMGQPENT-UHFFFAOYSA-N 0.000 claims description 2
• JLYPQNULHVBDCY-UHFFFAOYSA-N 4-[7-methyl-6-(3-methylsulfonylphenyl)-2-pyrimidin-5-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound N1=C2C(C)=C(C=3C=C(C=CC=3)S(C)(=O)=O)SC2=C(N2CCOCC2)N=C1C1=CN=CN=C1 JLYPQNULHVBDCY-UHFFFAOYSA-N 0.000 claims description 2
• WBQXCCZOJJBHBH-UHFFFAOYSA-N 4-morpholin-4-yl-2,6-dipyridin-3-ylfuro[3,2-d]pyrimidine Chemical compound C1COCCN1C1=NC(C=2C=NC=CC=2)=NC2=C1OC(C=1C=NC=CC=1)=C2 WBQXCCZOJJBHBH-UHFFFAOYSA-N 0.000 claims description 2
• NZTNKULXGWVEAW-UHFFFAOYSA-N 5-(4-morpholin-4-yl-6-phenylthieno[3,2-d]pyrimidin-2-yl)pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=CC=CC=3)C2=N1 NZTNKULXGWVEAW-UHFFFAOYSA-N 0.000 claims description 2
• KUEPXHQMEJKPTQ-UHFFFAOYSA-N 5-(4-morpholin-4-yl-6-pyridin-3-ylthieno[3,2-d]pyrimidin-2-yl)pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=NC=CC=3)C2=N1 KUEPXHQMEJKPTQ-UHFFFAOYSA-N 0.000 claims description 2
• YGUVTYJZJBZWNH-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(6-morpholin-4-ylpyridin-3-yl)thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=NC(=CC=3)N3CCOCC3)C2=N1 YGUVTYJZJBZWNH-UHFFFAOYSA-N 0.000 claims description 2
• CSQMKQQKCNTYNZ-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(6-piperazin-1-ylpyridin-3-yl)thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=NC(=CC=3)N3CCNCC3)C2=N1 CSQMKQQKCNTYNZ-UHFFFAOYSA-N 0.000 claims description 2
• JIHMSTBHDIXJIX-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[3-(2h-tetrazol-5-yl)phenyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(C=CC=3)C=3NN=NN=3)C2=N1 JIHMSTBHDIXJIX-UHFFFAOYSA-N 0.000 claims description 2
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• CICUCFROOXMJTE-UHFFFAOYSA-N 5-[6-(3,5-dimethyl-1,2-oxazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound CC1=NOC(C)=C1C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 CICUCFROOXMJTE-UHFFFAOYSA-N 0.000 claims description 2
• XRTJHURWFZREQG-UHFFFAOYSA-N 5-[6-(3-aminophenyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=CC=2)=C1 XRTJHURWFZREQG-UHFFFAOYSA-N 0.000 claims description 2
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• RLQYKCMSWPBXJL-UHFFFAOYSA-N 5-[6-(3-chlorophenyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(Cl)C=CC=3)C2=N1 RLQYKCMSWPBXJL-UHFFFAOYSA-N 0.000 claims description 2
• DXJFCVFLFNHIDB-UHFFFAOYSA-N 5-[6-(3-methoxyphenyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound COC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=CC=2)=C1 DXJFCVFLFNHIDB-UHFFFAOYSA-N 0.000 claims description 2
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• FGERISPBTGOLRH-UHFFFAOYSA-N 5-[6-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=CC=C1C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 FGERISPBTGOLRH-UHFFFAOYSA-N 0.000 claims description 2
• ZNUWWFZQVFEJNV-NSCUHMNNSA-N 5-[6-[(e)-3-methoxyprop-1-enyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C=12SC(/C=C/COC)=CC2=NC(C=2C=NC(N)=CC=2)=NC=1N1CCOCC1 ZNUWWFZQVFEJNV-NSCUHMNNSA-N 0.000 claims description 2
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• AQTJNMUVTLTNOV-UHFFFAOYSA-N [3-[2-(2-aminopyrimidin-5-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=NC(N)=NC=2)=C1 AQTJNMUVTLTNOV-UHFFFAOYSA-N 0.000 claims description 2
• XSRFFAWQIVNMCZ-UHFFFAOYSA-N [3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(C=CC=3)C(=O)N3CCOCC3)C2=N1 XSRFFAWQIVNMCZ-UHFFFAOYSA-N 0.000 claims description 2
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• KSBIEZQIEIRQNZ-UHFFFAOYSA-N [3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]methanol Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(CO)C=CC=3)C2=N1 KSBIEZQIEIRQNZ-UHFFFAOYSA-N 0.000 claims description 2
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• AXUDSNUGOKBGLV-UHFFFAOYSA-N [4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 AXUDSNUGOKBGLV-UHFFFAOYSA-N 0.000 claims description 2
• MONKPUWNDLARGA-UHFFFAOYSA-N [4-[2-(6-aminopyridin-3-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=C(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=CC=2)C=C1 MONKPUWNDLARGA-UHFFFAOYSA-N 0.000 claims description 2
• KSCHQDFDXDEJCN-UHFFFAOYSA-N [4-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 KSCHQDFDXDEJCN-UHFFFAOYSA-N 0.000 claims description 2
• PLUHBBRVTOIVHL-UHFFFAOYSA-N [4-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]methanol Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=CC(CO)=CC=3)C2=N1 PLUHBBRVTOIVHL-UHFFFAOYSA-N 0.000 claims description 2
• WWTATOVKZWWIIS-UHFFFAOYSA-N [5-[6-(3-methylsulfonylphenyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-yl]urea Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(NC(N)=O)=CC=2)=C1 WWTATOVKZWWIIS-UHFFFAOYSA-N 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
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• PAOZCFNRUBDYFK-UHFFFAOYSA-N n-[2-(4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidin-6-yl)propan-2-yl]benzamide Chemical compound C=1C2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2SC=1C(C)(C)NC(=O)C1=CC=CC=C1 PAOZCFNRUBDYFK-UHFFFAOYSA-N 0.000 claims description 2
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• USKNCKUBWODWMV-UHFFFAOYSA-N n-[2-[2-(2-aminopyrimidin-5-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=NC(N)=NC=2)=C1 USKNCKUBWODWMV-UHFFFAOYSA-N 0.000 claims description 2
• OKXNNRJCUOLWCV-UHFFFAOYSA-N n-[2-[2-(2-aminopyrimidin-5-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=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 OKXNNRJCUOLWCV-UHFFFAOYSA-N 0.000 claims description 2
• DGSNJDGQBHRZMZ-UHFFFAOYSA-N n-[2-[2-(2-aminopyrimidin-5-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=NC(N)=NC=2)=NC=1N1CCOCC1 DGSNJDGQBHRZMZ-UHFFFAOYSA-N 0.000 claims description 2
• QPYZSLNZTZPPKP-UHFFFAOYSA-N n-[2-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-yl]benzamide Chemical compound C=1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2SC=1C(C)(C)NC(=O)C1=CC=CC=C1 QPYZSLNZTZPPKP-UHFFFAOYSA-N 0.000 claims description 2
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• AMKIUFPHDYUIKK-UHFFFAOYSA-N n-[2-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-yl]benzamide Chemical compound C=1C2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2SC=1C(C)(C)NC(=O)C1=CC=CC=C1 AMKIUFPHDYUIKK-UHFFFAOYSA-N 0.000 claims description 2
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• QDYBYDWNYXRFEH-UHFFFAOYSA-N n-[3-[2-(2-aminopyrimidin-5-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=NC(N)=NC=2)=C1 QDYBYDWNYXRFEH-UHFFFAOYSA-N 0.000 claims description 2
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• UAEYUHMTWJZTNM-UHFFFAOYSA-N n-[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 UAEYUHMTWJZTNM-UHFFFAOYSA-N 0.000 claims description 2
• YKAYBUOTAQIABA-UHFFFAOYSA-N n-[3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=CC=2)=C1 YKAYBUOTAQIABA-UHFFFAOYSA-N 0.000 claims description 2
• RCZFODPCSPTOKE-UHFFFAOYSA-N n-[5-[6-(3-methylsulfonylphenyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(C=CC=3)S(C)(=O)=O)C2=N1 RCZFODPCSPTOKE-UHFFFAOYSA-N 0.000 claims description 2
• ZUQFMBAWPLAVCZ-UHFFFAOYSA-N n-[5-[6-(4-methoxypyridin-3-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidin-2-yl]pyridin-2-yl]acetamide Chemical compound COC1=CC=NC=C1C1=CC2=NC(C=3C=NC(NC(C)=O)=CC=3)=NC(N3CCOCC3)=C2O1 ZUQFMBAWPLAVCZ-UHFFFAOYSA-N 0.000 claims description 2
• DDLXJSVPZRZYRE-UHFFFAOYSA-N n-[5-[6-(4-methoxypyridin-3-yl)-4-morpholin-4-ylfuro[3,2-d]pyrimidin-2-yl]pyridin-2-yl]formamide Chemical compound COC1=CC=NC=C1C1=CC2=NC(C=3C=NC(NC=O)=CC=3)=NC(N3CCOCC3)=C2O1 DDLXJSVPZRZYRE-UHFFFAOYSA-N 0.000 claims description 2
• PDHQULOSIKFSND-UHFFFAOYSA-N n-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]-n-methylacetamide Chemical compound N1=C2SC(CN(C)C(C)=O)=CC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 PDHQULOSIKFSND-UHFFFAOYSA-N 0.000 claims description 2
• ARVHUQVRGROBOS-UHFFFAOYSA-N n-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]-n-methylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C)CC(SC1=N2)=CC1=C(N1CCOCC1)N=C2C1=CN=C(N)N=C1 ARVHUQVRGROBOS-UHFFFAOYSA-N 0.000 claims description 2
• ZIFIRDPRHHFJRU-UHFFFAOYSA-N n-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]-n-methylpyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)N(C)CC(SC1=N2)=CC1=C(N1CCOCC1)N=C2C1=CN=C(N)N=C1 ZIFIRDPRHHFJRU-UHFFFAOYSA-N 0.000 claims description 2
• DKOSOGVKRDREBS-UHFFFAOYSA-N n-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-2-hydroxy-n-methylacetamide Chemical compound C=12SC(CN(C)C(=O)CO)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 DKOSOGVKRDREBS-UHFFFAOYSA-N 0.000 claims description 2
• MQWKMQFFGKOSHT-UHFFFAOYSA-N n-[[2-(2-aminopyrimidin-5-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=NC(N)=NC=2)=NC=1N1CCOCC1 MQWKMQFFGKOSHT-UHFFFAOYSA-N 0.000 claims description 2
• BQIFXGYWHHKPCK-UHFFFAOYSA-N n-[[2-(2-aminopyrimidin-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=NC(N)=NC=2)=NC=1N1CCOCC1 BQIFXGYWHHKPCK-UHFFFAOYSA-N 0.000 claims description 2
• CHEFOPSRHOYRME-UHFFFAOYSA-N n-[[2-(2-aminopyrimidin-5-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=NC(N)=NC=1)=NC=2N1CCOCC1 CHEFOPSRHOYRME-UHFFFAOYSA-N 0.000 claims description 2
• CFPCFVBFTMZGKT-UHFFFAOYSA-N n-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylacetamide Chemical compound N1=C2C(C)=C(CN(C)C(C)=O)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 CFPCFVBFTMZGKT-UHFFFAOYSA-N 0.000 claims description 2
• AUOMQQOGGICEBY-UHFFFAOYSA-N n-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]-n-methylacetamide Chemical compound N1=C2SC(CN(C)C(C)=O)=CC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 AUOMQQOGGICEBY-UHFFFAOYSA-N 0.000 claims description 2
• VEQZBZGODTXASJ-UHFFFAOYSA-N n-[[2-(6-aminopyridin-3-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=NC(N)=CC=2)=NC=1N1CCOCC1 VEQZBZGODTXASJ-UHFFFAOYSA-N 0.000 claims description 2
• JNAFNOLZQMSDMW-UHFFFAOYSA-N n-[[2-(6-aminopyridin-3-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=NC(N)=CC=1)=NC=2N1CCOCC1 JNAFNOLZQMSDMW-UHFFFAOYSA-N 0.000 claims description 2
• VZLMSFCEAAGHDH-UHFFFAOYSA-N n-[[2-(6-aminopyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylacetamide Chemical compound N1=C2C(C)=C(CN(C)C(C)=O)SC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 VZLMSFCEAAGHDH-UHFFFAOYSA-N 0.000 claims description 2
• WRFJQROBFZZAEC-UHFFFAOYSA-N n-[[2-(6-aminopyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C)CC(=C(C1=N2)C)SC1=C(N1CCOCC1)N=C2C1=CC=C(N)N=C1 WRFJQROBFZZAEC-UHFFFAOYSA-N 0.000 claims description 2
• OWPGGPXPIRCIBN-UHFFFAOYSA-N n-[[2-(6-aminopyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylmethanesulfonamide Chemical compound N1=C2C(C)=C(CN(C)S(C)(=O)=O)SC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 OWPGGPXPIRCIBN-UHFFFAOYSA-N 0.000 claims description 2
• CGWXHZDPZQDSDX-UHFFFAOYSA-N n-[[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]methyl]-2-hydroxyacetamide Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(CNC(=O)CO)C=CC=3)C2=N1 CGWXHZDPZQDSDX-UHFFFAOYSA-N 0.000 claims description 2
• SRVFJAQAMZHQOF-UHFFFAOYSA-N n-[[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]methyl]methanesulfonamide Chemical compound CS(=O)(=O)NCC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 SRVFJAQAMZHQOF-UHFFFAOYSA-N 0.000 claims description 2
• CIQIKSBUMWJUKO-UHFFFAOYSA-N n-[[3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]methyl]methanesulfonamide Chemical compound N1=C2C(C)=C(C=3C=C(CNS(C)(=O)=O)C=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 CIQIKSBUMWJUKO-UHFFFAOYSA-N 0.000 claims description 2
• HJMWGWBQPVNDCN-UHFFFAOYSA-N n-[[4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]methyl]-2-hydroxyacetamide Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=CC(CNC(=O)CO)=CC=3)C2=N1 HJMWGWBQPVNDCN-UHFFFAOYSA-N 0.000 claims description 2
• UVSHJJHPKLWWKF-UHFFFAOYSA-N n-methyl-5-[6-(3-methylsulfonylphenyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridine-3-carboxamide Chemical compound CNC(=O)C1=CN=CC(C=2N=C3C=C(SC3=C(N3CCOCC3)N=2)C=2C=C(C=CC=2)S(C)(=O)=O)=C1 UVSHJJHPKLWWKF-UHFFFAOYSA-N 0.000 claims description 2
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 4
• WKJOQYHMXRVQDK-UHFFFAOYSA-N 2-(dimethylamino)acetamide Chemical compound CN(C)CC(N)=O WKJOQYHMXRVQDK-UHFFFAOYSA-N 0.000 claims 2
• MBUYEGCZHFNABJ-UHFFFAOYSA-N 2-[2-(2,4-dimethoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C(C)(C)O)C2=N1 MBUYEGCZHFNABJ-UHFFFAOYSA-N 0.000 claims 2
• AGYLMYICLGPSDB-UHFFFAOYSA-N 5-[6-(methylaminomethyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=12SC(CNC)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 AGYLMYICLGPSDB-UHFFFAOYSA-N 0.000 claims 2
• YWRRZECRLSCTIO-UHFFFAOYSA-N 5-[6-[2-(4-methylsulfonylpiperazin-1-yl)propan-2-yl]-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)(C)N1CCN(S(C)(=O)=O)CC1 YWRRZECRLSCTIO-UHFFFAOYSA-N 0.000 claims 2
• SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical compound CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 claims 2
• FABZXXJETVNBBX-UHFFFAOYSA-N n-(hydrazinecarbonyl)acetamide Chemical compound CC(=O)NC(=O)NN FABZXXJETVNBBX-UHFFFAOYSA-N 0.000 claims 2
• NLNWOQUJUFMOEN-UHFFFAOYSA-N n-[[2-(2,4-dimethoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylacetamide Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN(C)C(C)=O)=C2)C2=N1 NLNWOQUJUFMOEN-UHFFFAOYSA-N 0.000 claims 2
• ROQIFXIWCHTSHW-UHFFFAOYSA-N n-[[2-(2,4-dimethoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylmethanesulfonamide Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN(C)S(C)(=O)=O)=C2)C2=N1 ROQIFXIWCHTSHW-UHFFFAOYSA-N 0.000 claims 2
• XGQPAHFEOKKHEF-UHFFFAOYSA-N n-[[2-(2-amino-1,3-thiazol-5-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=2SC(N)=NC=2)=NC=1N1CCOCC1 XGQPAHFEOKKHEF-UHFFFAOYSA-N 0.000 claims 2
• XDPITACJYINWFA-CQSZACIVSA-N (2r)-1-[3-[2-(2-aminopyrimidin-5-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=NC(N)=NC=2)=C1 XDPITACJYINWFA-CQSZACIVSA-N 0.000 claims 1
• SBOVBYGGJMETCV-OAHLLOKOSA-N (2r)-1-[3-[2-(6-aminopyridin-3-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=NC(N)=CC=2)=C1 SBOVBYGGJMETCV-OAHLLOKOSA-N 0.000 claims 1
• XDPITACJYINWFA-AWEZNQCLSA-N (2s)-1-[3-[2-(2-aminopyrimidin-5-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=NC(N)=NC=2)=C1 XDPITACJYINWFA-AWEZNQCLSA-N 0.000 claims 1
• SBOVBYGGJMETCV-HNNXBMFYSA-N (2s)-1-[3-[2-(6-aminopyridin-3-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=NC(N)=CC=2)=C1 SBOVBYGGJMETCV-HNNXBMFYSA-N 0.000 claims 1
• XRMGJUMPNOHAMB-ZDUSSCGKSA-N (2s)-1-[4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-4-hydroxypiperidin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCC1(O)C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 XRMGJUMPNOHAMB-ZDUSSCGKSA-N 0.000 claims 1
• IQOMAVAQHKMHAH-ZDUSSCGKSA-N (2s)-n-[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-2-hydroxypropanamide Chemical compound C[C@H](O)C(=O)NC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 IQOMAVAQHKMHAH-ZDUSSCGKSA-N 0.000 claims 1
• SCMGGWQUEKJNCA-AWEZNQCLSA-N (2s)-n-[3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-2-hydroxypropanamide Chemical compound C[C@H](O)C(=O)NC1=CC=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)=C1 SCMGGWQUEKJNCA-AWEZNQCLSA-N 0.000 claims 1
• GWWMJUSDTAVOCZ-AWEZNQCLSA-N (2s)-n-[3-[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-2-hydroxypropanamide Chemical compound C[C@H](O)C(=O)NC1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=CC=2)=C1 GWWMJUSDTAVOCZ-AWEZNQCLSA-N 0.000 claims 1
• GEWBBXFVPCPBLS-HNNXBMFYSA-N (2s)-n-[[3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]methyl]-2-hydroxypropanamide Chemical compound C[C@H](O)C(=O)NCC1=CC=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)=C1 GEWBBXFVPCPBLS-HNNXBMFYSA-N 0.000 claims 1
• BTYKVIATSNHDTK-UHFFFAOYSA-N 1-[4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-4-hydroxypiperidin-1-yl]-2-hydroxy-2-methylpropan-1-one Chemical compound C1CN(C(=O)C(C)(O)C)CCC1(O)C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 BTYKVIATSNHDTK-UHFFFAOYSA-N 0.000 claims 1
• CDPRWGBBNIAGAZ-UHFFFAOYSA-N 1-[4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-4-hydroxypiperidin-1-yl]-2-hydroxyethanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C3(O)CCN(CC3)C(=O)CO)C2=N1 CDPRWGBBNIAGAZ-UHFFFAOYSA-N 0.000 claims 1
• GJXXTPLSZKIDAX-UHFFFAOYSA-N 1-[4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-4-hydroxypiperidin-1-yl]-2-methylsulfonylethanone Chemical compound C1CN(C(=O)CS(=O)(=O)C)CCC1(O)C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 GJXXTPLSZKIDAX-UHFFFAOYSA-N 0.000 claims 1
• WBDXQPPFBGQJOX-UHFFFAOYSA-N 1-[4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]piperidin-3-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(N=CC=3)N3CC(O)CCC3)C2=N1 WBDXQPPFBGQJOX-UHFFFAOYSA-N 0.000 claims 1
• CFUJRCAQDGGZQO-UHFFFAOYSA-N 1-[4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]piperidin-4-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(N=CC=3)N3CCC(O)CC3)C2=N1 CFUJRCAQDGGZQO-UHFFFAOYSA-N 0.000 claims 1
• JQNSIRMESBCWPF-UHFFFAOYSA-N 1-[4-[3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]benzoyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(=O)C1=CC=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)=C1 JQNSIRMESBCWPF-UHFFFAOYSA-N 0.000 claims 1
• LRXYQDHNHRGAMA-UHFFFAOYSA-N 1-[5-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]piperidin-4-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=NC(=CC=3)N3CCC(O)CC3)C2=N1 LRXYQDHNHRGAMA-UHFFFAOYSA-N 0.000 claims 1
• OPCHCIJTWXUYEK-UHFFFAOYSA-N 1-[[4-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]thiophen-2-yl]methyl]pyrrolidin-3-ol Chemical compound N1=C2C(C)=C(C=3C=C(CN4CC(O)CC4)SC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 OPCHCIJTWXUYEK-UHFFFAOYSA-N 0.000 claims 1
• MIYNUPHGPIOAET-UHFFFAOYSA-N 1-ethyl-3-[5-[6-(2-hydroxypropan-2-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-yl]urea Chemical compound C1=NC(NC(=O)NCC)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C(C)(C)O)C2=N1 MIYNUPHGPIOAET-UHFFFAOYSA-N 0.000 claims 1
• YKISPRDNOSAEGE-UHFFFAOYSA-N 1-n-[5-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]-2-methylpropane-1,2-diamine Chemical compound N1=C2C(C)=C(C=3C=NC(NCC(C)(C)N)=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 YKISPRDNOSAEGE-UHFFFAOYSA-N 0.000 claims 1
• OVWHMFUVUHAJIY-UHFFFAOYSA-N 2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-amine Chemical compound C=12SC(N)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 OVWHMFUVUHAJIY-UHFFFAOYSA-N 0.000 claims 1
• QCKBFWGHBUJCJN-UHFFFAOYSA-N 2-(4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidin-6-yl)propan-2-ol Chemical compound C=12SC(C(C)(O)C)=CC2=NC(C=2C=NC=CC=2)=NC=1N1CCOCC1 QCKBFWGHBUJCJN-UHFFFAOYSA-N 0.000 claims 1
• JJALFTHLLNWBCV-UHFFFAOYSA-N 2-[2-(2-amino-1,3-thiazol-5-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=2SC(N)=NC=2)=NC=1N1CCOCC1 JJALFTHLLNWBCV-UHFFFAOYSA-N 0.000 claims 1
• SFWTVVNNVHWDEE-UHFFFAOYSA-N 2-[2-(2-amino-4-methylpyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound CC1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C(C)(C)O)C2=N1 SFWTVVNNVHWDEE-UHFFFAOYSA-N 0.000 claims 1
• HDUPBTUZOHRKEL-JTQLQIEISA-N 2-[2-(2-aminopyrimidin-5-yl)-4-[(3s)-3-methylmorpholin-4-yl]thieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(N)=NC=2)=NC2=C1SC(C(C)(C)O)=C2 HDUPBTUZOHRKEL-JTQLQIEISA-N 0.000 claims 1
• RPZINZUTWTXPMJ-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylfuro[2,3-d]pyrimidin-6-yl]propan-2-ol Chemical compound N1=C2OC(C(C)(O)C)=CC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 RPZINZUTWTXPMJ-UHFFFAOYSA-N 0.000 claims 1
• CAIRAYAGJVFNJL-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C(O)(C(F)(F)F)C(F)(F)F)C2=N1 CAIRAYAGJVFNJL-UHFFFAOYSA-N 0.000 claims 1
• GBQONBBYGWTFQA-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-1,1,1-trifluoropropan-2-ol Chemical compound C=12SC(C(O)(C)C(F)(F)F)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 GBQONBBYGWTFQA-UHFFFAOYSA-N 0.000 claims 1
• FKMZKMXVMCJFMF-UHFFFAOYSA-N 2-[2-(2-fluoropyridin-3-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(=NC=CC=2)F)=NC=1N1CCOCC1 FKMZKMXVMCJFMF-UHFFFAOYSA-N 0.000 claims 1
• JIQLQXPFKHZJMS-UHFFFAOYSA-N 2-[2-(2-methoxypyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound COC1=NC=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C(C)(C)O)C2=N1 JIQLQXPFKHZJMS-UHFFFAOYSA-N 0.000 claims 1
• ADQWQXVODRNIAZ-UHFFFAOYSA-N 2-[2-(2-methoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]propan-2-ol Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(S2)C(C)(C)O)C2=N1 ADQWQXVODRNIAZ-UHFFFAOYSA-N 0.000 claims 1
• BIRVWRXTVMFKJP-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound COC1=CC=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C(C)(C)O)C2=N1 BIRVWRXTVMFKJP-UHFFFAOYSA-N 0.000 claims 1
• OFOPMDHCNHLIHI-UHFFFAOYSA-N 2-[2-(5-methoxypyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound COC1=CN=CC(C=2N=C3C=C(SC3=C(N3CCOCC3)N=2)C(C)(C)O)=C1 OFOPMDHCNHLIHI-UHFFFAOYSA-N 0.000 claims 1
• RQMUNSIPGNPBDE-UHFFFAOYSA-N 2-[2-(6-methoxypyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound C1=NC(OC)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C(C)(C)O)C2=N1 RQMUNSIPGNPBDE-UHFFFAOYSA-N 0.000 claims 1
• UIYMGHRKDVJVHS-UHFFFAOYSA-N 2-[2-[2-(methylamino)pyrimidin-5-yl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]propan-2-ol Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(S2)C(C)(C)O)C2=N1 UIYMGHRKDVJVHS-UHFFFAOYSA-N 0.000 claims 1
• XVLDIBUOTAUZJA-UHFFFAOYSA-N 2-[2-[2-(methylamino)pyrimidin-5-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C(C)(C)O)C2=N1 XVLDIBUOTAUZJA-UHFFFAOYSA-N 0.000 claims 1
• GAUUZXLGYPZCJK-UHFFFAOYSA-N 2-[2-[3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]anilino]ethoxy]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(NCCOCCO)C=CC=3)C2=N1 GAUUZXLGYPZCJK-UHFFFAOYSA-N 0.000 claims 1
• YZWATYVZXHOIIX-UHFFFAOYSA-N 2-[2-[4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]anilino]ethoxy]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=CC(NCCOCCO)=CC=3)C2=N1 YZWATYVZXHOIIX-UHFFFAOYSA-N 0.000 claims 1
• PMSGKCWNQPCNFT-UHFFFAOYSA-N 2-[2-[5-(hydroxymethyl)pyridin-3-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=C(CO)C=NC=2)=NC=1N1CCOCC1 PMSGKCWNQPCNFT-UHFFFAOYSA-N 0.000 claims 1
• BWUSRRFBMMUUGV-UHFFFAOYSA-N 2-[2-[5-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]oxyethoxy]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=NC(OCCOCCO)=CC=3)C2=N1 BWUSRRFBMMUUGV-UHFFFAOYSA-N 0.000 claims 1
• HZLQCVHWPYZGQH-UHFFFAOYSA-N 2-[2-[6-(methylamino)pyridin-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]propan-2-ol Chemical compound C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C(C)(C)O)C2=N1 HZLQCVHWPYZGQH-UHFFFAOYSA-N 0.000 claims 1
• CIUDVHXWRVTBBP-UHFFFAOYSA-N 2-[2-[[5-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]amino]ethoxy]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=NC(NCCOCCO)=CC=3)C2=N1 CIUDVHXWRVTBBP-UHFFFAOYSA-N 0.000 claims 1
• PIJJHJXIXTUHEH-UHFFFAOYSA-N 2-[2-[[5-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]amino]ethoxy]ethanol Chemical compound N1=C2C(C)=C(C=3C=NC(NCCOCCO)=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 PIJJHJXIXTUHEH-UHFFFAOYSA-N 0.000 claims 1
• URXYNRIPNFRKRP-UHFFFAOYSA-N 2-[3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenoxy]ethanol Chemical compound N1=C2C(C)=C(C=3C=C(OCCO)C=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 URXYNRIPNFRKRP-UHFFFAOYSA-N 0.000 claims 1
• QFWUBDJINHQUTQ-UHFFFAOYSA-N 2-[3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-1-(4-hydroxypiperidin-1-yl)ethanone Chemical compound N1=C2C(C)=C(C=3C=C(CC(=O)N4CCC(O)CC4)C=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 QFWUBDJINHQUTQ-UHFFFAOYSA-N 0.000 claims 1
• KSQKUBWNPUAQLA-UHFFFAOYSA-N 2-[3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1CN(C)CCN1C(=O)CC1=CC=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)=C1 KSQKUBWNPUAQLA-UHFFFAOYSA-N 0.000 claims 1
• UCNUGWSJPLYMKJ-UHFFFAOYSA-N 2-[3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-1-morpholin-4-ylethanone Chemical compound N1=C2C(C)=C(C=3C=C(CC(=O)N4CCOCC4)C=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 UCNUGWSJPLYMKJ-UHFFFAOYSA-N 0.000 claims 1
• NUMUPOHDJSPVIC-UHFFFAOYSA-N 2-[3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]acetic acid Chemical compound N1=C2C(C)=C(C=3C=C(CC(O)=O)C=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 NUMUPOHDJSPVIC-UHFFFAOYSA-N 0.000 claims 1
• BKEQFQSQGONJAN-UHFFFAOYSA-N 2-[4-[5-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]piperazin-1-yl]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=NC(=CC=3)N3CCN(CCO)CC3)C2=N1 BKEQFQSQGONJAN-UHFFFAOYSA-N 0.000 claims 1
• GNRDONFECLQYAQ-UHFFFAOYSA-N 2-[5-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-1,2,4-oxadiazol-3-yl]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3ON=C(CCO)N=3)C2=N1 GNRDONFECLQYAQ-UHFFFAOYSA-N 0.000 claims 1
• UWWLZUOSCJIVMA-UHFFFAOYSA-N 2-[5-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-1,2,4-oxadiazol-3-yl]propan-2-ol Chemical compound CC(C)(O)C1=NOC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=N1 UWWLZUOSCJIVMA-UHFFFAOYSA-N 0.000 claims 1
• MZATUCQGRYAFHO-UHFFFAOYSA-N 2-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]amino]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(NCCO)=C2)C2=N1 MZATUCQGRYAFHO-UHFFFAOYSA-N 0.000 claims 1
• XOSWDBDNTPQLCC-UHFFFAOYSA-N 2-[[4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]amino]propan-1-ol Chemical compound C1=NC(NC(CO)C)=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 XOSWDBDNTPQLCC-UHFFFAOYSA-N 0.000 claims 1
• MMYLQEWVVMLZEE-UHFFFAOYSA-N 2-[[5-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]amino]-1-morpholin-4-ylethanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=NC(NCC(=O)N4CCOCC4)=CC=3)C2=N1 MMYLQEWVVMLZEE-UHFFFAOYSA-N 0.000 claims 1
• HMWDUMACQJNETM-UHFFFAOYSA-N 2-[[5-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]amino]propan-1-ol Chemical compound C1=NC(NC(CO)C)=CC=C1C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 HMWDUMACQJNETM-UHFFFAOYSA-N 0.000 claims 1
• HVEGVRCFACUULP-UHFFFAOYSA-N 2-[[5-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]amino]-1-morpholin-4-ylethanone Chemical compound N1=C2C(C)=C(C=3C=NC(NCC(=O)N4CCOCC4)=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 HVEGVRCFACUULP-UHFFFAOYSA-N 0.000 claims 1
• MAGKYUHLXNMQJY-UHFFFAOYSA-N 2-amino-1-[4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-4-hydroxypiperidin-1-yl]-2-methylpropan-1-one Chemical compound C1CN(C(=O)C(C)(N)C)CCC1(O)C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 MAGKYUHLXNMQJY-UHFFFAOYSA-N 0.000 claims 1
• CGUQRBSJOVUGDB-UHFFFAOYSA-N 2-amino-1-[4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-4-hydroxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN)CCC1(O)C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 CGUQRBSJOVUGDB-UHFFFAOYSA-N 0.000 claims 1
• DGSOCBZFBYRRPI-UHFFFAOYSA-N 2-methoxy-n-[5-[7-methyl-6-(3-methylsulfonylphenyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)COC)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2C)C=3C=C(C=CC=3)S(C)(=O)=O)C2=N1 DGSOCBZFBYRRPI-UHFFFAOYSA-N 0.000 claims 1
• VLJAOHUEFFSGNO-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]oxetan-3-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(S2)C3(O)COC3)C2=N1 VLJAOHUEFFSGNO-UHFFFAOYSA-N 0.000 claims 1
• XALAUGGFRRAFRQ-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-(2-hydroxyethyl)benzamide Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(C=CC=3)C(=O)NCCO)C2=N1 XALAUGGFRRAFRQ-UHFFFAOYSA-N 0.000 claims 1
• LIQVUXZTANNLQC-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-(2-methoxyethyl)benzamide Chemical compound COCCNC(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 LIQVUXZTANNLQC-UHFFFAOYSA-N 0.000 claims 1
• WBSPYZORNGLUDX-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-[2-(dimethylamino)ethyl]benzamide Chemical compound CN(C)CCNC(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 WBSPYZORNGLUDX-UHFFFAOYSA-N 0.000 claims 1
• WBYOINDIFRDDKC-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]oxetan-3-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C3(O)COC3)C2=N1 WBYOINDIFRDDKC-UHFFFAOYSA-N 0.000 claims 1
• FXNGJMWZTQMXOG-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-(2,3-dihydroxypropyl)-n-methylbenzamide Chemical compound OCC(O)CN(C)C(=O)C1=CC=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)=C1 FXNGJMWZTQMXOG-UHFFFAOYSA-N 0.000 claims 1
• ANAJFZPKBIIRNQ-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-(2,3-dihydroxypropyl)benzamide Chemical compound N1=C2C(C)=C(C=3C=C(C=CC=3)C(=O)NCC(O)CO)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 ANAJFZPKBIIRNQ-UHFFFAOYSA-N 0.000 claims 1
• XCVQKFLYPSRGAK-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-(2-hydroxyethyl)benzamide Chemical compound N1=C2C(C)=C(C=3C=C(C=CC=3)C(=O)NCCO)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 XCVQKFLYPSRGAK-UHFFFAOYSA-N 0.000 claims 1
• JVBUEWGWXXONQO-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-(2-methoxyethyl)benzamide Chemical compound COCCNC(=O)C1=CC=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)=C1 JVBUEWGWXXONQO-UHFFFAOYSA-N 0.000 claims 1
• QJUCFQDHNIWCFE-AWEZNQCLSA-N 3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-[(2s)-2-hydroxypropyl]benzamide Chemical compound C[C@H](O)CNC(=O)C1=CC=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)=C1 QJUCFQDHNIWCFE-AWEZNQCLSA-N 0.000 claims 1
• QPNWGBQVRDJLMD-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-[2-(dimethylamino)ethyl]benzamide Chemical compound CN(C)CCNC(=O)C1=CC=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)=C1 QPNWGBQVRDJLMD-UHFFFAOYSA-N 0.000 claims 1
• WYGWJBAYKZBVNY-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]benzoic acid Chemical compound N1=C2C(C)=C(C=3C=C(C=CC=3)C(O)=O)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 WYGWJBAYKZBVNY-UHFFFAOYSA-N 0.000 claims 1
• CEHPNGCLOMPCNY-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenol Chemical compound N1=C2C(C)=C(C=3C=C(O)C=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 CEHPNGCLOMPCNY-UHFFFAOYSA-N 0.000 claims 1
• STHSTIIJKJGPKZ-UHFFFAOYSA-N 3-[[5-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]-methylamino]propane-1,2-diol Chemical compound C1=NC(N(CC(O)CO)C)=CC=C1C1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 STHSTIIJKJGPKZ-UHFFFAOYSA-N 0.000 claims 1
• QUOFDIMUWKZUAC-UHFFFAOYSA-N 3-[[5-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]pyridin-2-yl]amino]propane-1,2-diol Chemical compound N1=C2C(C)=C(C=3C=NC(NCC(O)CO)=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 QUOFDIMUWKZUAC-UHFFFAOYSA-N 0.000 claims 1
• MZORXXCJMRQFMH-UHFFFAOYSA-N 4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[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=NC(N)=NC=2)=C1 MZORXXCJMRQFMH-UHFFFAOYSA-N 0.000 claims 1
• DLKZUBINSTZQQU-UHFFFAOYSA-N 4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-1-methylpiperidin-4-ol Chemical compound C1CN(C)CCC1(O)C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 DLKZUBINSTZQQU-UHFFFAOYSA-N 0.000 claims 1
• GTWOYITYFOPWRK-UHFFFAOYSA-N 4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-(2-hydroxyethyl)-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCO)=CC=C1C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 GTWOYITYFOPWRK-UHFFFAOYSA-N 0.000 claims 1
• SVJJOPUPKWGCAT-UHFFFAOYSA-N 4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]piperidin-4-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C3(O)CCNCC3)C2=N1 SVJJOPUPKWGCAT-UHFFFAOYSA-N 0.000 claims 1
• DDKUREMPQDNBOJ-UHFFFAOYSA-N 4-[2-(dimethylamino)ethyl]piperazine-1-carbaldehyde Chemical compound CN(C)CCN1CCN(C=O)CC1 DDKUREMPQDNBOJ-UHFFFAOYSA-N 0.000 claims 1
• MGFPAVWAEGIUAY-UHFFFAOYSA-N 4-[7-methyl-6-(3-methylsulfonylphenyl)-2-pyridazin-3-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound N1=C2C(C)=C(C=3C=C(C=CC=3)S(C)(=O)=O)SC2=C(N2CCOCC2)N=C1C1=CC=CN=N1 MGFPAVWAEGIUAY-UHFFFAOYSA-N 0.000 claims 1
• LGASZEGELMNESJ-UHFFFAOYSA-N 5-(4-morpholin-4-yl-6-phenylthieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=CC=CC=3)C2=N1 LGASZEGELMNESJ-UHFFFAOYSA-N 0.000 claims 1
• SPXDVJSXODORHE-UHFFFAOYSA-N 5-(6,7-dimethyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine Chemical compound N1=C2C(C)=C(C)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 SPXDVJSXODORHE-UHFFFAOYSA-N 0.000 claims 1
• HUAKZDFLUWCHHY-UHFFFAOYSA-N 5-(6-methyl-4-morpholin-4-yl-2-thiophen-2-ylthieno[3,2-d]pyrimidin-7-yl)pyrimidin-2-amine Chemical compound CC=1SC2=C(N3CCOCC3)N=C(C=3SC=CC=3)N=C2C=1C1=CN=C(N)N=C1 HUAKZDFLUWCHHY-UHFFFAOYSA-N 0.000 claims 1
• RSJFWACCANTLLB-UHFFFAOYSA-N 5-(6-methyl-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl)pyrimidin-2-amine Chemical compound N1=C2SC(C)=CC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 RSJFWACCANTLLB-UHFFFAOYSA-N 0.000 claims 1
• GTVGPBQGUPCTKG-UHFFFAOYSA-N 5-(6-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine Chemical compound C=12SC(C)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 GTVGPBQGUPCTKG-UHFFFAOYSA-N 0.000 claims 1
• HNZMQRYKDXSETP-UHFFFAOYSA-N 5-(7-methyl-4-morpholin-4-yl-6-phenylthieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine Chemical compound N1=C2C(C)=C(C=3C=CC=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 HNZMQRYKDXSETP-UHFFFAOYSA-N 0.000 claims 1
• FFKAROCKAZYIJI-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound CC(C)C1=NOC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=N1 FFKAROCKAZYIJI-UHFFFAOYSA-N 0.000 claims 1
• QHUGEOGVGXEHAH-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)thieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3ON=C(N=3)C=3C=NC=CC=3)C2=N1 QHUGEOGVGXEHAH-UHFFFAOYSA-N 0.000 claims 1
• VSGIHOKIOMRSMN-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(4-morpholin-4-ylphenyl)thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=CC(=CC=3)N3CCOCC3)C2=N1 VSGIHOKIOMRSMN-UHFFFAOYSA-N 0.000 claims 1
• VAUKQNODUWGGGJ-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[2-(2-morpholin-4-ylethylamino)pyridin-4-yl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(NCCN4CCOCC4)N=CC=3)C2=N1 VAUKQNODUWGGGJ-UHFFFAOYSA-N 0.000 claims 1
• SGFCVFYHQYDTKR-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3ON=C(N=3)C=3C=CC(=CC=3)C(F)(F)F)C2=N1 SGFCVFYHQYDTKR-UHFFFAOYSA-N 0.000 claims 1
• RHFJLSIXMVHPLE-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[4-(2-morpholin-4-ylethylamino)phenyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=CC(NCCN4CCOCC4)=CC=3)C2=N1 RHFJLSIXMVHPLE-UHFFFAOYSA-N 0.000 claims 1
• MTXBGSWXNCHNGU-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[6-(2-morpholin-4-ylethoxy)pyridin-3-yl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=NC(OCCN4CCOCC4)=CC=3)C2=N1 MTXBGSWXNCHNGU-UHFFFAOYSA-N 0.000 claims 1
• RDBDHLFFLKBQNW-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[6-(2-morpholin-4-ylethylamino)pyridin-3-yl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=NC(NCCN4CCOCC4)=CC=3)C2=N1 RDBDHLFFLKBQNW-UHFFFAOYSA-N 0.000 claims 1
• SUPIFJHKLLIGBH-UHFFFAOYSA-N 5-[6-(2-methoxypropan-2-yl)-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(S2)C(C)(C)OC)C2=N1 SUPIFJHKLLIGBH-UHFFFAOYSA-N 0.000 claims 1
• RYXZQCFXIAKXCP-UHFFFAOYSA-N 5-[6-(2-methoxypropan-2-yl)-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(S2)C(C)(C)OC)C2=N1 RYXZQCFXIAKXCP-UHFFFAOYSA-N 0.000 claims 1
• CBLOVEBQPRPWJT-UHFFFAOYSA-N 5-[6-(2-methoxypropan-2-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound N1=C2SC(C(C)(C)OC)=CC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 CBLOVEBQPRPWJT-UHFFFAOYSA-N 0.000 claims 1
• CBFNGPQLGPBHMO-UHFFFAOYSA-N 5-[6-(2-methoxypropan-2-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]-n-methylpyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C(C)(C)OC)C2=N1 CBFNGPQLGPBHMO-UHFFFAOYSA-N 0.000 claims 1
• BRCOIQMZYMWNIS-UHFFFAOYSA-N 5-[6-(2-methoxypropan-2-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=12SC(C(C)(C)OC)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 BRCOIQMZYMWNIS-UHFFFAOYSA-N 0.000 claims 1
• WTBLRERGVZKNLX-UHFFFAOYSA-N 5-[6-(2-methylsulfonylpyridin-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(S(=O)(=O)C)=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 WTBLRERGVZKNLX-UHFFFAOYSA-N 0.000 claims 1
• XMRWJHOMBPOEIG-UHFFFAOYSA-N 5-[6-(3,4-dihydro-1h-isoquinolin-2-ylmethyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CC3=CC=CC=C3CC2)=C2)C2=N1 XMRWJHOMBPOEIG-UHFFFAOYSA-N 0.000 claims 1
• CLAHVNGNNQNCOF-UHFFFAOYSA-N 5-[6-(3-aminophenyl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound N1=C2C(C)=C(C=3C=C(N)C=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 CLAHVNGNNQNCOF-UHFFFAOYSA-N 0.000 claims 1
• IENORIRXMJJWAW-UHFFFAOYSA-N 5-[6-(3-methoxyoxetan-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]-n-methylpyridin-2-amine Chemical compound C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C3(COC3)OC)C2=N1 IENORIRXMJJWAW-UHFFFAOYSA-N 0.000 claims 1
• QFYZZVWRTOQFME-UHFFFAOYSA-N 5-[6-(3-methoxyoxetan-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]-n-methylpyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C3(COC3)OC)C2=N1 QFYZZVWRTOQFME-UHFFFAOYSA-N 0.000 claims 1
• KBTBHOPRFNFYOA-UHFFFAOYSA-N 5-[6-(3-methoxyoxetan-3-yl)-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=1C1(OC)COC1 KBTBHOPRFNFYOA-UHFFFAOYSA-N 0.000 claims 1
• BKLACXKAUGUPCO-UHFFFAOYSA-N 5-[6-(6-methoxypyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 BKLACXKAUGUPCO-UHFFFAOYSA-N 0.000 claims 1
• MTWBPVKVFQBKBZ-UHFFFAOYSA-N 5-[6-[(2-methoxyethylamino)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=12SC(CNCCOC)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 MTWBPVKVFQBKBZ-UHFFFAOYSA-N 0.000 claims 1
• JANRIQFKAZRPPS-UHFFFAOYSA-N 5-[6-[(3-methoxypropylamino)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=12SC(CNCCCOC)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 JANRIQFKAZRPPS-UHFFFAOYSA-N 0.000 claims 1
• BXOPCNIANXGNNG-UHFFFAOYSA-N 5-[6-[2-(2-methoxyethylamino)pyridin-4-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(NCCOC)=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 BXOPCNIANXGNNG-UHFFFAOYSA-N 0.000 claims 1
• KFKSRLMLPWRYPQ-UHFFFAOYSA-N 5-[6-[2-(dimethylamino)propan-2-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=12SC(C(C)(C)N(C)C)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 KFKSRLMLPWRYPQ-UHFFFAOYSA-N 0.000 claims 1
• KEKNROFFHOYRAX-UHFFFAOYSA-N 5-[6-[2-[2-methoxyethyl(methyl)amino]pyridin-4-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N(C)CCOC)=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 KEKNROFFHOYRAX-UHFFFAOYSA-N 0.000 claims 1
• CVNQBEOLHYNWGS-UHFFFAOYSA-N 5-[6-[3-(1-methyltetrazol-5-yl)phenyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound CN1N=NN=C1C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 CVNQBEOLHYNWGS-UHFFFAOYSA-N 0.000 claims 1
• ZBOBRSGPVGRITK-UHFFFAOYSA-N 5-[6-[3-(aminomethyl)phenyl]-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound N1=C2C(C)=C(C=3C=C(CN)C=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 ZBOBRSGPVGRITK-UHFFFAOYSA-N 0.000 claims 1
• LZFPPLIZZLLZKD-UHFFFAOYSA-N 5-[6-[5-(2-aminopropan-2-yl)-1,2,4-oxadiazol-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound O1C(C(C)(N)C)=NC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=N1 LZFPPLIZZLLZKD-UHFFFAOYSA-N 0.000 claims 1
• UOTPJPKEUVDDQC-UHFFFAOYSA-N 5-[6-[5-(methylsulfonylmethyl)-1,2,4-oxadiazol-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound O1C(CS(=O)(=O)C)=NC(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=N1 UOTPJPKEUVDDQC-UHFFFAOYSA-N 0.000 claims 1
• VLJFUKQOPLDKRP-UHFFFAOYSA-N 5-[6-[6-(1,1-dioxo-1,4-thiazinan-4-yl)pyridin-3-yl]-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical class N1=C2C(C)=C(C=3C=NC(=CC=3)N3CCS(=O)(=O)CC3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 VLJFUKQOPLDKRP-UHFFFAOYSA-N 0.000 claims 1
• AYTAEDJAQSGXKD-UHFFFAOYSA-N 5-[6-[6-(2-methoxyethylamino)pyridin-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(NCCOC)=CC=C1C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 AYTAEDJAQSGXKD-UHFFFAOYSA-N 0.000 claims 1
• DENJOWGFFZAVMU-UHFFFAOYSA-N 5-[6-[6-(2-methylsulfonylethylamino)pyridin-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(NCCS(=O)(=O)C)=CC=C1C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 DENJOWGFFZAVMU-UHFFFAOYSA-N 0.000 claims 1
• PVLVYMWFYSFIHB-IYBDPMFKSA-N 5-[6-[6-[(2r,6s)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical class C1[C@@H](C)O[C@@H](C)CN1C1=CC=C(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)C=N1 PVLVYMWFYSFIHB-IYBDPMFKSA-N 0.000 claims 1
• LPGZCOISZAOCTC-UHFFFAOYSA-N 5-[6-[6-[2-methoxyethyl(methyl)amino]pyridin-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N(C)CCOC)=CC=C1C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 LPGZCOISZAOCTC-UHFFFAOYSA-N 0.000 claims 1
• CZVBYFAURRZYPY-UHFFFAOYSA-N 5-[6-[6-[bis(2-methoxyethyl)amino]pyridin-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N(CCOC)CCOC)=CC=C1C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 CZVBYFAURRZYPY-UHFFFAOYSA-N 0.000 claims 1
• BNZWQUQWTNMQHK-UHFFFAOYSA-N 5-[6-[[(2,4-difluorophenyl)methyl-methylamino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=1C=C(F)C=C(F)C=1CN(C)CC(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 BNZWQUQWTNMQHK-UHFFFAOYSA-N 0.000 claims 1
• VPGCVISELYMUHN-UHFFFAOYSA-N 5-[6-[[2-methoxyethyl(methyl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=12SC(CN(C)CCOC)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 VPGCVISELYMUHN-UHFFFAOYSA-N 0.000 claims 1
• ZYLWLKUWLUVOOI-UHFFFAOYSA-N 5-[6-[[benzyl(methyl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=1C=CC=CC=1CN(C)CC(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 ZYLWLKUWLUVOOI-UHFFFAOYSA-N 0.000 claims 1
• CCNGHKIBXHTEQH-UHFFFAOYSA-N 5-[6-[[methyl(2-methylsulfonylethyl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=12SC(CN(CCS(C)(=O)=O)C)=CC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 CCNGHKIBXHTEQH-UHFFFAOYSA-N 0.000 claims 1
• INVKFJHZEQGYKB-UHFFFAOYSA-N 5-[7-methyl-4-(4-morpholin-4-yl-2-piperazin-2-ylsulfonylphenyl)thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound N1=C2C(C)=CSC2=C(C=2C(=CC(=CC=2)N2CCOCC2)S(=O)(=O)C2NCCNC2)N=C1C1=CN=C(N)N=C1 INVKFJHZEQGYKB-UHFFFAOYSA-N 0.000 claims 1
• QPPGZJLFRDWVNO-UHFFFAOYSA-N 5-[7-methyl-4-morpholin-4-yl-6-[3-(2-morpholin-4-ylethoxy)phenyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound N1=C2C(C)=C(C=3C=C(OCCN4CCOCC4)C=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 QPPGZJLFRDWVNO-UHFFFAOYSA-N 0.000 claims 1
• OAPCYKISWMHBPL-UHFFFAOYSA-N 5-[7-methyl-4-morpholin-4-yl-6-[3-(morpholin-4-ylmethyl)phenyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound N1=C2C(C)=C(C=3C=C(CN4CCOCC4)C=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 OAPCYKISWMHBPL-UHFFFAOYSA-N 0.000 claims 1
• FYRWSEVFABLPOF-UHFFFAOYSA-N 5-[7-methyl-4-morpholin-4-yl-6-[6-(2-morpholin-4-ylethylamino)pyridin-3-yl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound N1=C2C(C)=C(C=3C=NC(NCCN4CCOCC4)=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 FYRWSEVFABLPOF-UHFFFAOYSA-N 0.000 claims 1
• LYZNCDFDLSPYPY-UHFFFAOYSA-N 5-[7-methyl-6-(2-methylsulfonylphenyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound N1=C2C(C)=C(C=3C(=CC=CC=3)S(C)(=O)=O)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 LYZNCDFDLSPYPY-UHFFFAOYSA-N 0.000 claims 1
• CEGGBJSKQYSDQL-UHFFFAOYSA-N 5-[7-methyl-6-(4-methylsulfonylphenyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound N1=C2C(C)=C(C=3C=CC(=CC=3)S(C)(=O)=O)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 CEGGBJSKQYSDQL-UHFFFAOYSA-N 0.000 claims 1
• AJCVHFJENCXVBR-UHFFFAOYSA-N 5-[7-methyl-6-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CC1=CC=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)=C1 AJCVHFJENCXVBR-UHFFFAOYSA-N 0.000 claims 1
• LNDHDXQQWWHANQ-UHFFFAOYSA-N 5-[7-methyl-6-[5-[(4-methylpiperazin-1-yl)methyl]thiophen-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CC1=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)=CS1 LNDHDXQQWWHANQ-UHFFFAOYSA-N 0.000 claims 1
• BYKZIWOFCPEKQE-UHFFFAOYSA-N 5-[7-methyl-6-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical class C1CN(C)CCN1C1=CC=C(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)C=N1 BYKZIWOFCPEKQE-UHFFFAOYSA-N 0.000 claims 1
• IPALKWNVUGSKPO-UHFFFAOYSA-N C1COCCN1C2=NC=NC3=C2SC(C3)(C4=C(N=CC=C4)N)C5=CC=CC=C5CCCO Chemical compound C1COCCN1C2=NC=NC3=C2SC(C3)(C4=C(N=CC=C4)N)C5=CC=CC=C5CCCO IPALKWNVUGSKPO-UHFFFAOYSA-N 0.000 claims 1
• RJJACCVSBSWNRN-UHFFFAOYSA-N CNCC1=CC2=C(N=C(N=C2N2CCOCC2)C=2C=NC(=CC=2)C)S1 Chemical compound CNCC1=CC2=C(N=C(N=C2N2CCOCC2)C=2C=NC(=CC=2)C)S1 RJJACCVSBSWNRN-UHFFFAOYSA-N 0.000 claims 1
• BKTDPYVBBLOQJW-UHFFFAOYSA-N CS(=O)(=O)CCNC1=NC=CC(=C1)C2(NC3=C(C(=N2)N4CCOCC4)SC=C3)C5=NC(=NC=C5)N Chemical compound CS(=O)(=O)CCNC1=NC=CC(=C1)C2(NC3=C(C(=N2)N4CCOCC4)SC=C3)C5=NC(=NC=C5)N BKTDPYVBBLOQJW-UHFFFAOYSA-N 0.000 claims 1
• PVCJKHHOXFKFRP-UHFFFAOYSA-N N-acetylethanolamine Chemical compound CC(=O)NCCO PVCJKHHOXFKFRP-UHFFFAOYSA-N 0.000 claims 1
• SWNFVQLQCNTBMQ-VIFPVBQESA-N [2-(2-aminopyrimidin-5-yl)-4-[(3s)-3-methylmorpholin-4-yl]thieno[3,2-d]pyrimidin-6-yl]methanol Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(N)=NC=2)=NC2=C1SC(CO)=C2 SWNFVQLQCNTBMQ-VIFPVBQESA-N 0.000 claims 1
• UJJPXLNQQSUKDD-UHFFFAOYSA-N [2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-(3-methylsulfonylphenyl)methanol Chemical compound CS(=O)(=O)C1=CC=CC(C(O)C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 UJJPXLNQQSUKDD-UHFFFAOYSA-N 0.000 claims 1
• GUJZRRGUWKGDEC-UHFFFAOYSA-N [2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C1=CC=CC(C(=O)C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)=C1 GUJZRRGUWKGDEC-UHFFFAOYSA-N 0.000 claims 1
• WYDHIBOQVQAHOX-UHFFFAOYSA-N [2-(2-aminopyrimidin-5-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=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 WYDHIBOQVQAHOX-UHFFFAOYSA-N 0.000 claims 1
• BTZGOUDSHGSFPW-UHFFFAOYSA-N [2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-(4-methylsulfonylphenyl)methanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 BTZGOUDSHGSFPW-UHFFFAOYSA-N 0.000 claims 1
• HIQNVGHHPXBIGW-UHFFFAOYSA-N [2-[2-(dimethylamino)pyrimidin-5-yl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methanol Chemical compound C1=NC(N(C)C)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CO)S2)C2=N1 HIQNVGHHPXBIGW-UHFFFAOYSA-N 0.000 claims 1
• XMQUCBMDKZRPMS-UHFFFAOYSA-N [3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(C=2SC3=NC(=NC(=C3C=2)N2CCOCC2)C=2C=NC(N)=NC=2)=C1 XMQUCBMDKZRPMS-UHFFFAOYSA-N 0.000 claims 1
• WLAYUAPZLNYGDA-UHFFFAOYSA-N [3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-(3-hydroxypyrrolidin-1-yl)methanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(C=CC=3)C(=O)N3CC(O)CC3)C2=N1 WLAYUAPZLNYGDA-UHFFFAOYSA-N 0.000 claims 1
• CRKSYBDFYKJOMD-UHFFFAOYSA-N [3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-(4-hydroxypiperidin-1-yl)methanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(C=CC=3)C(=O)N3CCC(O)CC3)C2=N1 CRKSYBDFYKJOMD-UHFFFAOYSA-N 0.000 claims 1
• ZORHTBOXMMRPPV-UHFFFAOYSA-N [3-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-[4-(2-hydroxyethyl)piperazin-1-yl]methanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(C=CC=3)C(=O)N3CCN(CCO)CC3)C2=N1 ZORHTBOXMMRPPV-UHFFFAOYSA-N 0.000 claims 1
• WSPVMONUSVZUKH-UHFFFAOYSA-N [3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-(4-hydroxypiperidin-1-yl)methanone Chemical compound N1=C2C(C)=C(C=3C=C(C=CC=3)C(=O)N3CCC(O)CC3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 WSPVMONUSVZUKH-UHFFFAOYSA-N 0.000 claims 1
• NXFDDILCQZFXOX-UHFFFAOYSA-N [3-[2-(2-aminopyrimidin-5-yl)-7-methyl-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(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)=C1 NXFDDILCQZFXOX-UHFFFAOYSA-N 0.000 claims 1
• WAVVAEBAVMUFKV-UHFFFAOYSA-N [3-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl]-[4-(1,3-thiazol-2-yl)piperazin-1-yl]methanone Chemical compound N1=C2C(C)=C(C=3C=C(C=CC=3)C(=O)N3CCN(CC3)C=3SC=CN=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 WAVVAEBAVMUFKV-UHFFFAOYSA-N 0.000 claims 1
• RKUQYUSQDAZUPJ-UHFFFAOYSA-N [4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-2-chlorophenyl]-(4-hydroxypiperidin-1-yl)methanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=C2)C=3C=C(Cl)C(C(=O)N4CCC(O)CC4)=CC=3)C2=N1 RKUQYUSQDAZUPJ-UHFFFAOYSA-N 0.000 claims 1
• XQVRRBDTFDJDER-UHFFFAOYSA-N [4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-2-chlorophenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)C=C1Cl XQVRRBDTFDJDER-UHFFFAOYSA-N 0.000 claims 1
• UGPYTYFCQXWAPJ-UHFFFAOYSA-N [4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-3-methylphenyl]-(4-hydroxypiperidin-1-yl)methanone Chemical compound CC1=CC(C(=O)N2CCC(O)CC2)=CC=C1C(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 UGPYTYFCQXWAPJ-UHFFFAOYSA-N 0.000 claims 1
• GOEKWEDTLBKBFS-UHFFFAOYSA-N [4-[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-3-methylphenyl]-morpholin-4-ylmethanone Chemical compound CC1=CC(C(=O)N2CCOCC2)=CC=C1C(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 GOEKWEDTLBKBFS-UHFFFAOYSA-N 0.000 claims 1
• VHNSDNQRHUMXDS-UHFFFAOYSA-N [4-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]phenyl] piperidine-1-carboxylate Chemical compound N1=C2C(C)=C(C=3C=CC(OC(=O)N4CCCCC4)=CC=3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 VHNSDNQRHUMXDS-UHFFFAOYSA-N 0.000 claims 1
• UTESMFVMKISQOI-UHFFFAOYSA-N [4-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]thiophen-2-yl]-(4-hydroxypiperidin-1-yl)methanone Chemical compound N1=C2C(C)=C(C=3C=C(SC=3)C(=O)N3CCC(O)CC3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 UTESMFVMKISQOI-UHFFFAOYSA-N 0.000 claims 1
• RRQVRWUUXHOCGI-UHFFFAOYSA-N [4-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]thiophen-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC(C2=C(C3=NC(=NC(=C3S2)N2CCOCC2)C=2C=NC(N)=NC=2)C)=CS1 RRQVRWUUXHOCGI-UHFFFAOYSA-N 0.000 claims 1
• GIRRLFWAEYIBOO-UHFFFAOYSA-N [4-[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]thiophen-2-yl]-morpholin-4-ylmethanone Chemical compound N1=C2C(C)=C(C=3C=C(SC=3)C(=O)N3CCOCC3)SC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 GIRRLFWAEYIBOO-UHFFFAOYSA-N 0.000 claims 1
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