JP2005508904A - 血管新生阻害剤としてのフロ−及びチエノピリミジン誘導体 - Google Patents

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Publication number

JP2005508904A

JP2005508904A JP2003526926A JP2003526926A JP2005508904A JP 2005508904 A JP2005508904 A JP 2005508904A JP 2003526926 A JP2003526926 A JP 2003526926A JP 2003526926 A JP2003526926 A JP 2003526926A JP 2005508904 A JP2005508904 A JP 2005508904A

Authority

JP

Japan

Prior art keywords

amino

pyrimidine

furo

phenyl

methoxyphenyl

Prior art date

2001-09-11

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.)

Pending

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• Global Dossier
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• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title abstract description 6
• JUQAECQBUNODQP-UHFFFAOYSA-N furo[3,2-d]pyrimidine Chemical compound C1=NC=C2OC=CC2=N1 JUQAECQBUNODQP-UHFFFAOYSA-N 0.000 title abstract description 5
• 229940121369 angiogenesis inhibitor Drugs 0.000 title 1
• 239000004037 angiogenesis inhibitor Substances 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 558
• 150000001875 compounds Chemical class 0.000 claims abstract description 316
• 101000753291 Homo sapiens Angiopoietin-1 receptor Proteins 0.000 claims abstract description 46
• 102100022014 Angiopoietin-1 receptor Human genes 0.000 claims abstract description 44
• 238000011282 treatment Methods 0.000 claims abstract description 17
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
• 229940091171 VEGFR-2 tyrosine kinase inhibitor Drugs 0.000 claims abstract description 5
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 235
• 125000003118 aryl group Chemical group 0.000 claims description 171
• 239000001257 hydrogen Substances 0.000 claims description 130
• 229910052739 hydrogen Inorganic materials 0.000 claims description 130
• 125000001072 heteroaryl group Chemical group 0.000 claims description 119
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 97
• 150000002431 hydrogen Chemical class 0.000 claims description 93
• KQGXYVJZOMKLSA-UHFFFAOYSA-N furo[2,3-d]pyrimidine Chemical compound N1=CN=C2OC=CC2=C1 KQGXYVJZOMKLSA-UHFFFAOYSA-N 0.000 claims description 87
• 150000003839 salts Chemical class 0.000 claims description 78
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
• 239000012453 solvate Substances 0.000 claims description 65
• 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 49
• 125000000623 heterocyclic group Chemical group 0.000 claims description 46
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims description 38
• 230000000694 effects Effects 0.000 claims description 38
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 33
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 33
• 201000010099 disease Diseases 0.000 claims description 33
• 230000033115 angiogenesis Effects 0.000 claims description 30
• BJHCYTJNPVGSBZ-YXSASFKJSA-N 1-[4-[6-amino-5-[(Z)-methoxyiminomethyl]pyrimidin-4-yl]oxy-2-chlorophenyl]-3-ethylurea Chemical compound CCNC(=O)Nc1ccc(Oc2ncnc(N)c2\C=N/OC)cc1Cl BJHCYTJNPVGSBZ-YXSASFKJSA-N 0.000 claims description 29
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 206010028980 Neoplasm Diseases 0.000 claims description 26
• 239000008194 pharmaceutical composition Substances 0.000 claims description 26
• ZGBOTCWLWRJVJR-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(N2C(=C3C=COC3=NC2)N)C=CC=1N(C(=O)N)C1=CC(C(F)(F)F)=CC=C1F ZGBOTCWLWRJVJR-UHFFFAOYSA-N 0.000 claims description 25
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• 201000011510 cancer Diseases 0.000 claims description 22
• 241000124008 Mammalia Species 0.000 claims description 19
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 17
• 239000003795 chemical substances by application Substances 0.000 claims description 16
• 102000009465 Growth Factor Receptors Human genes 0.000 claims description 15
• 108010009202 Growth Factor Receptors Proteins 0.000 claims description 15
• 239000002246 antineoplastic agent Substances 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• 125000004104 aryloxy group Chemical group 0.000 claims description 14
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 11
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 11
• 108091008605 VEGF receptors Proteins 0.000 claims description 11
• 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims description 11
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
• 230000001404 mediated effect Effects 0.000 claims description 10
• 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 9
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 8
• 229940034982 antineoplastic agent Drugs 0.000 claims description 8
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• MXDHMMOFLYOTRT-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-[2-chloro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(N2C(=C3C=COC3=NC2)N)C=CC=1N(C(=O)N)C1=CC(C(F)(F)F)=CC=C1Cl MXDHMMOFLYOTRT-UHFFFAOYSA-N 0.000 claims description 6
• AFUOTDYMXQXSJS-UHFFFAOYSA-N 2-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=NC(N)=C(C=CO2)C2=N1 AFUOTDYMXQXSJS-UHFFFAOYSA-N 0.000 claims description 6
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 6
• XDAMQPRBHUTTCG-UHFFFAOYSA-N 3-bromo-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1N(Br)C(N)=C2C=COC2=N1 XDAMQPRBHUTTCG-UHFFFAOYSA-N 0.000 claims description 6
• 102000001301 EGF receptor Human genes 0.000 claims description 6
• 108060006698 EGF receptor Proteins 0.000 claims description 6
• 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 229940124597 therapeutic agent Drugs 0.000 claims description 6
• ORAVNLCBRIPLMI-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=CC=C1Cl ORAVNLCBRIPLMI-UHFFFAOYSA-N 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• JGYQAOSASDFNCN-UHFFFAOYSA-N 1-[4-(4-amino-2-bromo-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(N2C(=C3C=COC3=NC2Br)N)C=CC=1N(C(=O)N)C1=CC(C(F)(F)F)=CC=C1F JGYQAOSASDFNCN-UHFFFAOYSA-N 0.000 claims description 4
• CTAHQNODWJVCRV-UHFFFAOYSA-N 1-[4-[4-amino-2-(3-cyanophenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound NC1=C2C=COC2=NC(C=2C=C(C=CC=2)C#N)N1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F CTAHQNODWJVCRV-UHFFFAOYSA-N 0.000 claims description 4
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
• PAFMLFYBUZOZHJ-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(=CC=2)N(C)C)C(N)=C2C=COC2=N1 PAFMLFYBUZOZHJ-UHFFFAOYSA-N 0.000 claims description 4
• RUBVBRUXOISIHL-UHFFFAOYSA-N 3-[4-amino-3-[4-(2,3-difluorophenyl)phenyl]-2h-furo[2,3-d]pyrimidin-2-yl]benzenesulfonamide Chemical compound NC1=C2C=COC2=NC(C=2C=C(C=CC=2)S(N)(=O)=O)N1C(C=C1)=CC=C1C1=CC=CC(F)=C1F RUBVBRUXOISIHL-UHFFFAOYSA-N 0.000 claims description 4
• 108091008606 PDGF receptors Proteins 0.000 claims description 4
• 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 claims description 4
• 102100033178 Vascular endothelial growth factor receptor 1 Human genes 0.000 claims description 4
• 102100033179 Vascular endothelial growth factor receptor 3 Human genes 0.000 claims description 4
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• RRWJKYUSTORXSI-UHFFFAOYSA-N n-[3-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]phenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=CC(NS(C)(=O)=O)=C1 RRWJKYUSTORXSI-UHFFFAOYSA-N 0.000 claims description 4
• KTICBGNIIKMUIL-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-(3,4-dichlorophenyl)cyclopropane-1-carboxamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)C1(C=2C=C(Cl)C(Cl)=CC=2)CC1 KTICBGNIIKMUIL-UHFFFAOYSA-N 0.000 claims description 4
• VBZLKFMUUWQHTF-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-(3-chlorophenyl)cyclopropane-1-carboxamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)C1(C=2C=C(Cl)C=CC=2)CC1 VBZLKFMUUWQHTF-UHFFFAOYSA-N 0.000 claims description 4
• NKQIZMMOPRIAIG-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-[3,5-bis(trifluoromethyl)phenyl]cyclopropane-1-carboxamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)C1(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CC1 NKQIZMMOPRIAIG-UHFFFAOYSA-N 0.000 claims description 4
• OKMPGKNBUISIHZ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-phenylcyclopropane-1-carboxamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)C1(C=2C=CC=CC=2)CC1 OKMPGKNBUISIHZ-UHFFFAOYSA-N 0.000 claims description 4
• RPEGTHCMTXLIRI-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-1-(3,4-dichlorophenyl)cyclopropane-1-carboxamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)C1(C=2C=C(Cl)C(Cl)=CC=2)CC1 RPEGTHCMTXLIRI-UHFFFAOYSA-N 0.000 claims description 4
• XBVNKWWPVWHOSV-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-1-(3-chlorophenyl)cyclopropane-1-carboxamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)C1(C=2C=C(Cl)C=CC=2)CC1 XBVNKWWPVWHOSV-UHFFFAOYSA-N 0.000 claims description 4
• FKMNEFUIORDNRF-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-1-[3,5-bis(trifluoromethyl)phenyl]cyclopropane-1-carboxamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)C1(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CC1 FKMNEFUIORDNRF-UHFFFAOYSA-N 0.000 claims description 4
• SPQYLSSMQINTMH-UHFFFAOYSA-N n-[4-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-chlorobenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(NS(=O)(=O)C=3C=C(Cl)C=CC=3)=CC=2)C(N)=C2C=COC2=N1 SPQYLSSMQINTMH-UHFFFAOYSA-N 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 claims description 4
• WWVNZJFLBWRBLV-MOPGFXCFSA-N (1s,2s)-n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1([C@H]2C[C@@H]2C(=O)NC2=CC=C(C=C2)N2CN=C3SC=CC3=C2N)=CC=CC=C1 WWVNZJFLBWRBLV-MOPGFXCFSA-N 0.000 claims description 3
• TUUMOSUUOPASSP-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]urea Chemical compound CC(=O)C1=CC=CC(NC(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 TUUMOSUUOPASSP-UHFFFAOYSA-N 0.000 claims description 3
• HDNXQDRPZCDVFL-UHFFFAOYSA-N 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[4-(6-methylsulfanyl-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]urea Chemical compound C1N=C2OC(SC)=CC2=CN1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F HDNXQDRPZCDVFL-UHFFFAOYSA-N 0.000 claims description 3
• GTOZZUZZXVICES-UHFFFAOYSA-N 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[4-(6-methylsulfonyl-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]urea Chemical compound C1N=C2OC(S(=O)(=O)C)=CC2=CN1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F GTOZZUZZXVICES-UHFFFAOYSA-N 0.000 claims description 3
• MYZDWSWTKWOSER-UHFFFAOYSA-N 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[4-[6-(methylamino)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]urea Chemical compound C1N=C2OC(NC)=CC2=CN1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F MYZDWSWTKWOSER-UHFFFAOYSA-N 0.000 claims description 3
• QQZULPFIHNYTOA-UHFFFAOYSA-N 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[4-[6-[(2,4,6-trimethoxyphenyl)methylamino]-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]urea Chemical compound COC1=CC(OC)=CC(OC)=C1CNC1=CC2=CN(C=3C=CC(NC(=O)NC=4C(=CC=C(C=4)C(F)(F)F)F)=CC=3)CN=C2O1 QQZULPFIHNYTOA-UHFFFAOYSA-N 0.000 claims description 3
• OXOAJFHRPICLBS-UHFFFAOYSA-N 1-[3-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(2,3-dihydro-1h-inden-5-yl)urea Chemical compound C1=C2CCCC2=CC(NC(=O)NC=2C=CC=C(C=2)N2CN=C3OC=CC3=C2N)=C1 OXOAJFHRPICLBS-UHFFFAOYSA-N 0.000 claims description 3
• RLNHONDFQUYFOW-UHFFFAOYSA-N 1-[3-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(4-chlorophenyl)urea Chemical compound NC1=C2C=COC2=NCN1C(C=1)=CC=CC=1NC(=O)NC1=CC=C(Cl)C=C1 RLNHONDFQUYFOW-UHFFFAOYSA-N 0.000 claims description 3
• XYTKVHCOQZTYAY-UHFFFAOYSA-N 1-[3-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=C(C=CC=2)N2C(=C3C=COC3=NC2)N)=N1 XYTKVHCOQZTYAY-UHFFFAOYSA-N 0.000 claims description 3
• GOVYCWQSJJVYRT-UHFFFAOYSA-N 1-[3-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-butylurea Chemical compound CCCCNC(=O)NC1=CC=CC(N2C(=C3C=COC3=NC2)N)=C1 GOVYCWQSJJVYRT-UHFFFAOYSA-N 0.000 claims description 3
• BWIIJDFGUDXIFD-UHFFFAOYSA-N 1-[3-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-cyclohexylurea Chemical compound NC1=C2C=COC2=NCN1C(C=1)=CC=CC=1NC(=O)NC1CCCCC1 BWIIJDFGUDXIFD-UHFFFAOYSA-N 0.000 claims description 3
• RFNCFWBWVIRYFY-UHFFFAOYSA-N 1-[3-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-phenylurea Chemical compound NC1=C2C=COC2=NCN1C(C=1)=CC=CC=1NC(=O)NC1=CC=CC=C1 RFNCFWBWVIRYFY-UHFFFAOYSA-N 0.000 claims description 3
• BYNSPSCXUJRPAY-UHFFFAOYSA-N 1-[3-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-tert-butylurea Chemical compound CC(C)(C)NC(=O)NC1=CC=CC(N2C(=C3C=COC3=NC2)N)=C1 BYNSPSCXUJRPAY-UHFFFAOYSA-N 0.000 claims description 3
• VKNIANKAHPFXGZ-UHFFFAOYSA-N 1-[3-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=C(C=CC=2)N(C(N)=O)C=2C(=CC=C(C=2)C(F)(F)F)F)C(N)=C2C=COC2=N1 VKNIANKAHPFXGZ-UHFFFAOYSA-N 0.000 claims description 3
• HBRYYKKCWMSFAT-UHFFFAOYSA-N 1-[4-(4-amino-2-bromo-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(2,3-dihydro-1h-inden-5-yl)urea Chemical compound C1=C2CCCC2=CC(NC(=O)NC2=CC=C(C=C2)N2C(Br)N=C3OC=CC3=C2N)=C1 HBRYYKKCWMSFAT-UHFFFAOYSA-N 0.000 claims description 3
• QWRZCQQQNGYKQC-UHFFFAOYSA-N 1-[4-(4-amino-2-chloro-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(3-phenyl-1,2,4-thiadiazol-5-yl)urea Chemical compound NC1=C2C=COC2=NC(Cl)N1C(C=C1)=CC=C1NC(=O)NC(SN=1)=NC=1C1=CC=CC=C1 QWRZCQQQNGYKQC-UHFFFAOYSA-N 0.000 claims description 3
• YGYNDCRWUVVEPS-UHFFFAOYSA-N 1-[4-(4-amino-2-ethenyl-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(N2C(=C3C=COC3=NC2C=C)N)C=CC=1N(C(=O)N)C1=CC(C(F)(F)F)=CC=C1F YGYNDCRWUVVEPS-UHFFFAOYSA-N 0.000 claims description 3
• SWNKSJPABYYHTO-UHFFFAOYSA-N 1-[4-(4-amino-2-iodo-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(N2C(=C3C=COC3=NC2I)N)C=CC=1N(C(=O)N)C1=CC(C(F)(F)F)=CC=C1F SWNKSJPABYYHTO-UHFFFAOYSA-N 0.000 claims description 3
• DXVKUDKKYWXYOY-UHFFFAOYSA-N 1-[4-(4-amino-2-pyridin-3-yl-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C(C(F)(F)F)=CC=C(F)C=1N(C(=O)N)C(C=C1)=CC=C1N(C(=C1C=COC1=N1)N)C1C1=CC=CN=C1 DXVKUDKKYWXYOY-UHFFFAOYSA-N 0.000 claims description 3
• VNTXNDZMPRETAA-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-(2,2,4,4-tetrafluoro-1,3-benzodioxin-5-yl)urea Chemical compound O1C(F)(F)OC(F)(F)C2=C1C=CC=C2N(C(=O)N)C1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 VNTXNDZMPRETAA-UHFFFAOYSA-N 0.000 claims description 3
• KOHJOHQVWNWSAL-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-(2-fluoro-5-methoxyphenyl)urea Chemical compound COC1=CC=C(F)C(N(C(N)=O)C=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 KOHJOHQVWNWSAL-UHFFFAOYSA-N 0.000 claims description 3
• ODAJTPIRCPLQAD-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-[3-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(N2C(=C3C=COC3=NC2)N)C=CC=1N(C(=O)N)C1=CC(F)=CC(C(F)(F)F)=C1 ODAJTPIRCPLQAD-UHFFFAOYSA-N 0.000 claims description 3
• IYMIQGGQCUOTHB-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-phenylthiourea Chemical compound C=1C=C(N2C(=C3C=COC3=NC2)N)C=CC=1N(C(=S)N)C1=CC=CC=C1 IYMIQGGQCUOTHB-UHFFFAOYSA-N 0.000 claims description 3
• VJUMLIDSMNOFKX-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(1,3-benzodioxol-5-yl)urea Chemical compound C1=C2OCOC2=CC(NC(=O)NC2=CC=C(C=C2)N2CN=C3OC=CC3=C2N)=C1 VJUMLIDSMNOFKX-UHFFFAOYSA-N 0.000 claims description 3
• VQIGZHORRWFCIC-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(2,3-dihydro-1h-inden-5-yl)urea Chemical compound C1=C2CCCC2=CC(NC(=O)NC2=CC=C(C=C2)N2CN=C3OC=CC3=C2N)=C1 VQIGZHORRWFCIC-UHFFFAOYSA-N 0.000 claims description 3
• LMMLVTZXEOAIMQ-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(2,5-dimethoxyphenyl)urea Chemical compound COC1=CC=C(OC)C(NC(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 LMMLVTZXEOAIMQ-UHFFFAOYSA-N 0.000 claims description 3
• RMPNKBSUZVZRIX-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(2-chloro-5-nitrophenyl)urea Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)NC1=CC([N+]([O-])=O)=CC=C1Cl RMPNKBSUZVZRIX-UHFFFAOYSA-N 0.000 claims description 3
• PBSUNRBLJMPEEZ-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(2-chlorophenyl)urea Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1Cl PBSUNRBLJMPEEZ-UHFFFAOYSA-N 0.000 claims description 3
• TYUOGSSWMUKRBE-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(3-chlorophenyl)urea Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 TYUOGSSWMUKRBE-UHFFFAOYSA-N 0.000 claims description 3
• RDRJHPJJRKREKK-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(3-cyanophenyl)urea Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C#N)=C1 RDRJHPJJRKREKK-UHFFFAOYSA-N 0.000 claims description 3
• DETRPLRPRUQPOR-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(3-ethylphenyl)urea Chemical compound CCC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 DETRPLRPRUQPOR-UHFFFAOYSA-N 0.000 claims description 3
• CSKDDHHIOIFXQB-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(3-fluorophenyl)urea Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 CSKDDHHIOIFXQB-UHFFFAOYSA-N 0.000 claims description 3
• OZQRRABRCXABSD-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 OZQRRABRCXABSD-UHFFFAOYSA-N 0.000 claims description 3
• SFVPJNHKFXHMST-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(3-phenoxyphenyl)urea Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)NC(C=1)=CC=CC=1OC1=CC=CC=C1 SFVPJNHKFXHMST-UHFFFAOYSA-N 0.000 claims description 3
• POJBUVSLSMPDMG-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 POJBUVSLSMPDMG-UHFFFAOYSA-N 0.000 claims description 3
• VYVJZDSJUBLHFT-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(4-phenoxyphenyl)urea Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 VYVJZDSJUBLHFT-UHFFFAOYSA-N 0.000 claims description 3
• NDEZDZDCRSHYQN-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=N1 NDEZDZDCRSHYQN-UHFFFAOYSA-N 0.000 claims description 3
• BZZAPDQAENQTDD-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-[2,5-bis(trifluoromethyl)phenyl]urea Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1C(F)(F)F BZZAPDQAENQTDD-UHFFFAOYSA-N 0.000 claims description 3
• AGALNXFZAXFLRZ-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 AGALNXFZAXFLRZ-UHFFFAOYSA-N 0.000 claims description 3
• HKQYWHNBYSJBRC-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-[3-(trifluoromethylsulfanyl)phenyl]urea Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(SC(F)(F)F)=C1 HKQYWHNBYSJBRC-UHFFFAOYSA-N 0.000 claims description 3
• SOUVKQGCSWYRBR-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-[4-(dimethylamino)phenyl]urea Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 SOUVKQGCSWYRBR-UHFFFAOYSA-N 0.000 claims description 3
• WEXYRSBLLXJLQS-UHFFFAOYSA-N 1-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-thiophen-2-ylurea Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)NC1=CC=CS1 WEXYRSBLLXJLQS-UHFFFAOYSA-N 0.000 claims description 3
• FOFVAOAQNFZGNF-UHFFFAOYSA-N 1-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-1-[2-chloro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(N2C(=C3C=CSC3=NC2)N)C=CC=1N(C(=O)N)C1=CC(C(F)(F)F)=CC=C1Cl FOFVAOAQNFZGNF-UHFFFAOYSA-N 0.000 claims description 3
• WNMILEGPNBEJDY-UHFFFAOYSA-N 1-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-3-(2,3-dihydro-1h-inden-5-yl)urea Chemical compound C1=C2CCCC2=CC(NC(=O)NC2=CC=C(C=C2)N2CN=C3SC=CC3=C2N)=C1 WNMILEGPNBEJDY-UHFFFAOYSA-N 0.000 claims description 3
• CZIBIGDJYJZIRS-UHFFFAOYSA-N 1-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-3-(2-methylphenyl)urea Chemical compound CC1=CC=CC=C1NC(=O)NC1=CC=C(N2C(=C3C=CSC3=NC2)N)C=C1 CZIBIGDJYJZIRS-UHFFFAOYSA-N 0.000 claims description 3
• QRFFARQAVQOVLR-UHFFFAOYSA-N 1-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-3-(3-ethylphenyl)-1-methylurea Chemical compound CCC1=CC=CC(NC(=O)N(C)C=2C=CC(=CC=2)N2C(=C3C=CSC3=NC2)N)=C1 QRFFARQAVQOVLR-UHFFFAOYSA-N 0.000 claims description 3
• UFJOGSHORNYPHP-UHFFFAOYSA-N 1-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)N2C(=C3C=CSC3=NC2)N)=C1 UFJOGSHORNYPHP-UHFFFAOYSA-N 0.000 claims description 3
• ZHXNHKPXCNSMQF-UHFFFAOYSA-N 1-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]-1-methylurea Chemical compound C=1C=C(N2C(=C3C=CSC3=NC2)N)C=CC=1N(C)C(=O)NC1=CC(C(F)(F)F)=CC=C1F ZHXNHKPXCNSMQF-UHFFFAOYSA-N 0.000 claims description 3
• OQMQEVXYSCBIJS-UHFFFAOYSA-N 1-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F OQMQEVXYSCBIJS-UHFFFAOYSA-N 0.000 claims description 3
• YZRJQMCHBQGTNG-UHFFFAOYSA-N 1-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 YZRJQMCHBQGTNG-UHFFFAOYSA-N 0.000 claims description 3
• LHFSXEPMUARHSJ-UHFFFAOYSA-N 1-[4-(6-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(N2C=C3C=C(N)OC3=NC2)C=CC=1N(C(=O)N)C1=CC(C(F)(F)F)=CC=C1F LHFSXEPMUARHSJ-UHFFFAOYSA-N 0.000 claims description 3
• JQOJBNGGVIZIMZ-UHFFFAOYSA-N 1-[4-[4-(dimethylamino)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound CN(C)C1=C2C=COC2=NCN1C(C=C1)=CC=C1N(C(N)=O)C1=CC(C(F)(F)F)=CC=C1F JQOJBNGGVIZIMZ-UHFFFAOYSA-N 0.000 claims description 3
• MMHFOAUJORKDNA-UHFFFAOYSA-N 1-[4-[4-amino-2-(1,2-dihydroxyethyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound NC1=C2C=COC2=NC(C(O)CO)N1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F MMHFOAUJORKDNA-UHFFFAOYSA-N 0.000 claims description 3
• QRMIOCOQHWTJSH-UHFFFAOYSA-N 1-[4-[4-amino-2-(3-sulfamoylphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C(C(F)(F)F)=CC=C(F)C=1N(C(=O)N)C(C=C1)=CC=C1N(C(=C1C=COC1=N1)N)C1C1=CC=CC(S(N)(=O)=O)=C1 QRMIOCOQHWTJSH-UHFFFAOYSA-N 0.000 claims description 3
• XAGVUMZFBZRSIZ-UHFFFAOYSA-N 1-[4-[4-amino-2-(4-cyanophenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound NC1=C2C=COC2=NC(C=2C=CC(=CC=2)C#N)N1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F XAGVUMZFBZRSIZ-UHFFFAOYSA-N 0.000 claims description 3
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• RSSFLYIMGZANHR-UHFFFAOYSA-N 1-[4-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-1-phenylurea Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(=CC=2)N(C(N)=O)C=2C=CC=CC=2)C(N)=C2C=COC2=N1 RSSFLYIMGZANHR-UHFFFAOYSA-N 0.000 claims description 3
• ZOIWIQLHYOLGSD-UHFFFAOYSA-N 1-[4-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-(4-chlorophenyl)urea Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(NC(=O)NC=3C=CC(Cl)=CC=3)=CC=2)C(N)=C2C=COC2=N1 ZOIWIQLHYOLGSD-UHFFFAOYSA-N 0.000 claims description 3
• WZBVDACTZBKTGY-UHFFFAOYSA-N 1-[4-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-(4-tert-butyl-1,3-thiazol-2-yl)urea Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(NC(=O)NC=3SC=C(N=3)C(C)(C)C)=CC=2)C(N)=C2C=COC2=N1 WZBVDACTZBKTGY-UHFFFAOYSA-N 0.000 claims description 3
• XOUHZRUAPGGMKM-UHFFFAOYSA-N 1-[4-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(NC(=O)NC=3C(=CC=C(C=3)C(F)(F)F)F)=CC=2)C(N)=C2C=COC2=N1 XOUHZRUAPGGMKM-UHFFFAOYSA-N 0.000 claims description 3
• ZDAJSCPPXHZVRK-UHFFFAOYSA-N 1-[4-[4-amino-6-(3-methylsulfanylpropylamino)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1N=C2OC(NCCCSC)=CC2=C(N)N1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F ZDAJSCPPXHZVRK-UHFFFAOYSA-N 0.000 claims description 3
• LBQZYLOUVTXCJC-UHFFFAOYSA-N 1-[4-[4-amino-6-(3-methylsulfinylpropylamino)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1N=C2OC(NCCCS(=O)C)=CC2=C(N)N1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F LBQZYLOUVTXCJC-UHFFFAOYSA-N 0.000 claims description 3
• CTJHEQGOTTURHN-UHFFFAOYSA-N 1-[4-[4-amino-6-(dimethylamino)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1N=C2OC(N(C)C)=CC2=C(N)N1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F CTJHEQGOTTURHN-UHFFFAOYSA-N 0.000 claims description 3
• ITMKJQNZXBVPAW-UHFFFAOYSA-N 1-[4-[4-amino-6-(methylamino)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1N=C2OC(NC)=CC2=C(N)N1C(C=C1)=CC=C1N(C(N)=O)C1=CC(C(F)(F)F)=CC=C1F ITMKJQNZXBVPAW-UHFFFAOYSA-N 0.000 claims description 3
• KAYJWMRVAUTCSK-UHFFFAOYSA-N 1-[4-[4-amino-6-[(2,4,6-trimethoxyphenyl)methylamino]-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound COC1=CC(OC)=CC(OC)=C1CNC1=CC2=C(N)N(C=3C=CC(NC(=O)NC=4C(=CC=C(C=4)C(F)(F)F)F)=CC=3)CN=C2O1 KAYJWMRVAUTCSK-UHFFFAOYSA-N 0.000 claims description 3
• VPYARCYXPLBHIR-UHFFFAOYSA-N 1-[4-[4-amino-6-[2-(dimethylamino)ethylamino]-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1N=C2OC(NCCN(C)C)=CC2=C(N)N1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F VPYARCYXPLBHIR-UHFFFAOYSA-N 0.000 claims description 3
• UEDAMQFZCOVOLM-UHFFFAOYSA-N 1-[4-[4-amino-6-[2-(methanesulfonamido)ethylamino]-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1N=C2OC(NCCNS(=O)(=O)C)=CC2=C(N)N1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F UEDAMQFZCOVOLM-UHFFFAOYSA-N 0.000 claims description 3
• VYFIGEUJYKHJFQ-UHFFFAOYSA-N 1-[4-[6-[2-(dimethylamino)ethylamino]-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1N=C2OC(NCCN(C)C)=CC2=CN1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F VYFIGEUJYKHJFQ-UHFFFAOYSA-N 0.000 claims description 3
• CIGRQDINNYNXQC-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(OC)=CC=2)C(N)=C2C=COC2=N1 CIGRQDINNYNXQC-UHFFFAOYSA-N 0.000 claims description 3
• HOEYQBKIURPHOQ-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-5-methyl-5,6-dihydrofuro[2,3-d]pyrimidin-4-imine Chemical compound C1=CC(OC)=CC=C1C(N(C1=N)C=2C=CC(OC)=CC=2)=NC2=C1C(C)CO2 HOEYQBKIURPHOQ-UHFFFAOYSA-N 0.000 claims description 3
• QQMXCKUPEXBWJR-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-6-methyl-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(OC)=CC=2)C(N)=C2C=C(C)OC2=N1 QQMXCKUPEXBWJR-UHFFFAOYSA-N 0.000 claims description 3
• OFXZUVICJUOYLZ-UHFFFAOYSA-N 2,3-bis(4-methylphenyl)-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(C)=CC=2)C(N)=C2C=COC2=N1 OFXZUVICJUOYLZ-UHFFFAOYSA-N 0.000 claims description 3
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• QDZXXHKVNHCTGS-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-(4-methyl-1,3-thiazol-2-yl)-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=NC(C)=CS1 QDZXXHKVNHCTGS-UHFFFAOYSA-N 0.000 claims description 3
• HOWGOTZEXXCOPG-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-(4-methylsulfonylphenyl)-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=C(S(C)(=O)=O)C=C1 HOWGOTZEXXCOPG-UHFFFAOYSA-N 0.000 claims description 3
• PQDKCODOFJNRQE-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-(6-methoxypyridin-3-yl)-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=C(OC)N=C1 PQDKCODOFJNRQE-UHFFFAOYSA-N 0.000 claims description 3
• KIQQTPQWTHKSMH-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-[4-(trifluoromethoxy)phenyl]-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=C(OC(F)(F)F)C=C1 KIQQTPQWTHKSMH-UHFFFAOYSA-N 0.000 claims description 3
• CSTHVNXYRDECJW-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-naphthalen-1-yl-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=CC2=CC=CC=C12 CSTHVNXYRDECJW-UHFFFAOYSA-N 0.000 claims description 3
• FGBBITJVGPBLCO-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-naphthalen-2-yl-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=C(C=CC=C2)C2=C1 FGBBITJVGPBLCO-UHFFFAOYSA-N 0.000 claims description 3
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• MLBLTSXEMMGWOU-UHFFFAOYSA-N 3-(4-methylphenyl)-2-[4-(trifluoromethyl)phenyl]-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=C(C(F)(F)F)C=C1 MLBLTSXEMMGWOU-UHFFFAOYSA-N 0.000 claims description 3
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• DIEDHHDCQNPWNX-UHFFFAOYSA-N 3-(4-nitrophenyl)-n-phenyl-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(NC=2C=CC=CC=2)=C2C=COC2=NC1 DIEDHHDCQNPWNX-UHFFFAOYSA-N 0.000 claims description 3
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• CFCJKHVJBRAYMM-UHFFFAOYSA-N 3-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]-n-pyridin-4-ylbenzamide Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=CC(C(=O)NC=2C=CN=CC=2)=C1 CFCJKHVJBRAYMM-UHFFFAOYSA-N 0.000 claims description 3
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• UJPQZHWTBATQGO-UHFFFAOYSA-N 3-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=CC(C(O)=O)=C1 UJPQZHWTBATQGO-UHFFFAOYSA-N 0.000 claims description 3
• ZBSSODMCAZELOP-UHFFFAOYSA-N 3-[4-amino-3-(4-naphthalen-1-ylphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]benzenesulfonamide Chemical compound C=1C=C(C=2C3=CC=CC=C3C=CC=2)C=CC=1N1C(N)=C2C=COC2=NC1C1=CC=CC(S(N)(=O)=O)=C1 ZBSSODMCAZELOP-UHFFFAOYSA-N 0.000 claims description 3
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• IKHVDKVZJUNFCW-UHFFFAOYSA-N 3-[4-amino-3-(4-pyridin-3-ylphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]benzenesulfonamide Chemical compound NC1=C2C=COC2=NC(C=2C=C(C=CC=2)S(N)(=O)=O)N1C(C=C1)=CC=C1C1=CC=CN=C1 IKHVDKVZJUNFCW-UHFFFAOYSA-N 0.000 claims description 3
• HTZNLTRQVJTJJY-UHFFFAOYSA-N 3-[4-amino-3-[4-(4-ethylsulfonylphenyl)phenyl]-2h-furo[2,3-d]pyrimidin-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C1=CC=C(N2C(=C3C=COC3=NC2C=2C=C(C=CC=2)S(N)(=O)=O)N)C=C1 HTZNLTRQVJTJJY-UHFFFAOYSA-N 0.000 claims description 3
• NWNHGKSPSLTDRU-UHFFFAOYSA-N 3-[4-amino-3-[4-(4-tert-butylphenyl)phenyl]-2h-furo[2,3-d]pyrimidin-2-yl]benzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(N2C(=C3C=COC3=NC2C=2C=C(C=CC=2)S(N)(=O)=O)N)C=C1 NWNHGKSPSLTDRU-UHFFFAOYSA-N 0.000 claims description 3
• FIAUMTNGGXSEQM-UHFFFAOYSA-N 3-[4-amino-3-[4-[2,4-bis(trifluoromethyl)phenyl]phenyl]-2h-furo[2,3-d]pyrimidin-2-yl]benzenesulfonamide Chemical compound NC1=C2C=COC2=NC(C=2C=C(C=CC=2)S(N)(=O)=O)N1C(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1C(F)(F)F FIAUMTNGGXSEQM-UHFFFAOYSA-N 0.000 claims description 3
• SIXWSGNQPCZMHX-UHFFFAOYSA-N 3-[[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]methoxy]benzonitrile Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1COC1=CC=CC(C#N)=C1 SIXWSGNQPCZMHX-UHFFFAOYSA-N 0.000 claims description 3
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• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
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• JJWYPTKIBHWOGN-UHFFFAOYSA-N 4-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=C(C(O)=O)C=C1 JJWYPTKIBHWOGN-UHFFFAOYSA-N 0.000 claims description 3
• RPBOCTIJJDTJJU-UHFFFAOYSA-N 4-[4-amino-3-[4-[[2-fluoro-5-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-2h-furo[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound NC1=C2C=COC2=NC(C=2C=CC(=CC=2)C(O)=O)N1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F RPBOCTIJJDTJJU-UHFFFAOYSA-N 0.000 claims description 3
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• SJAIJEDDCGDCIQ-UHFFFAOYSA-N 4-amino-n-(2-amino-2-oxoethyl)-3-[4-[[2-fluoro-5-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-2h-furo[2,3-d]pyrimidine-2-carboxamide Chemical compound NC(=O)CNC(=O)C1N=C2OC=CC2=C(N)N1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F SJAIJEDDCGDCIQ-UHFFFAOYSA-N 0.000 claims description 3
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• BBZASSJOODWIOA-UHFFFAOYSA-N 4-amino-n-(4-chlorophenyl)-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C(=O)NC1=CC=C(Cl)C=C1 BBZASSJOODWIOA-UHFFFAOYSA-N 0.000 claims description 3
• SOQZEGBLKSJWMT-UHFFFAOYSA-N 4-amino-n-[2-(dimethylamino)ethyl]-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C(=O)NCCN(C)C SOQZEGBLKSJWMT-UHFFFAOYSA-N 0.000 claims description 3
• MCLCFBZGDCPMEV-UHFFFAOYSA-N 4-amino-n-[cyano(phenyl)methyl]-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C(=O)NC(C#N)C1=CC=CC=C1 MCLCFBZGDCPMEV-UHFFFAOYSA-N 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• TZBFOYQMXRPWNJ-UHFFFAOYSA-N 5-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]-2-(methylamino)benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(NC)=CC=C1C1N(C=2C=CC(OC)=CC=2)C(N)=C2C=COC2=N1 TZBFOYQMXRPWNJ-UHFFFAOYSA-N 0.000 claims description 3
• KNUMWMWWSNHXJN-UHFFFAOYSA-N 5-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]-2-chlorobenzamide Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=C(Cl)C(C(N)=O)=C1 KNUMWMWWSNHXJN-UHFFFAOYSA-N 0.000 claims description 3
• QULZLVYPYZVZTD-UHFFFAOYSA-N 5-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]-2-fluorobenzamide Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=C(F)C(C(N)=O)=C1 QULZLVYPYZVZTD-UHFFFAOYSA-N 0.000 claims description 3
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 3
• 101000851018 Homo sapiens Vascular endothelial growth factor receptor 1 Proteins 0.000 claims description 3
• 101000851030 Homo sapiens Vascular endothelial growth factor receptor 3 Proteins 0.000 claims description 3
• ZDHVVJJQHJAWDS-UHFFFAOYSA-N NC1=C2C(=NC(N1C1=CC=C(C=C1)C1=CC=C(C(=C1)F)C1=CC=CC=C1)C1=CC(=CC=C1)S(N)(=O)=O)OC=C2 Chemical compound NC1=C2C(=NC(N1C1=CC=C(C=C1)C1=CC=C(C(=C1)F)C1=CC=CC=C1)C1=CC(=CC=C1)S(N)(=O)=O)OC=C2 ZDHVVJJQHJAWDS-UHFFFAOYSA-N 0.000 claims description 3
• 108010090091 TIE-2 Receptor Proteins 0.000 claims description 3
• 102000012753 TIE-2 Receptor Human genes 0.000 claims description 3
• NTINMSZGTOMNSQ-UHFFFAOYSA-N [3-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=CC(C(=O)N2CCN(C)CC2)=C1 NTINMSZGTOMNSQ-UHFFFAOYSA-N 0.000 claims description 3
• PWZQVBMRHWYOOA-UHFFFAOYSA-N [3-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=CC(NC(N)=O)=C1 PWZQVBMRHWYOOA-UHFFFAOYSA-N 0.000 claims description 3
• YEOUOPIWYFZQIN-UHFFFAOYSA-N [4-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]methanol Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(CO)=CC=2)C(N)=C2C=COC2=N1 YEOUOPIWYFZQIN-UHFFFAOYSA-N 0.000 claims description 3
• YYUSNFQUICEPKI-UHFFFAOYSA-N [4-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]urea Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(NC(N)=O)=CC=2)C(N)=C2C=COC2=N1 YYUSNFQUICEPKI-UHFFFAOYSA-N 0.000 claims description 3
• XQFRJSMZILRJHB-UHFFFAOYSA-N [4-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=C(C(=O)N2CCOCC2)C=C1 XQFRJSMZILRJHB-UHFFFAOYSA-N 0.000 claims description 3
• AFXIIASKYISKSY-UHFFFAOYSA-N [4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)methanone Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C(=O)N1CC2=CC(OC)=C(OC)C=C2CC1 AFXIIASKYISKSY-UHFFFAOYSA-N 0.000 claims description 3
• PRQLBXXAAPISEY-UHFFFAOYSA-N benzyl n-[3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-4-yl]carbamate Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)OCC=2C=CC=CC=2)=C2C=COC2=NC1 PRQLBXXAAPISEY-UHFFFAOYSA-N 0.000 claims description 3
• 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• NPMSLZBBVKCONS-UHFFFAOYSA-N ethyl 2-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(C2N(C(N)=C3C=COC3=N2)C=2C=CC(OC)=CC=2)=N1 NPMSLZBBVKCONS-UHFFFAOYSA-N 0.000 claims description 3
• RNBVNEFECGSALY-UHFFFAOYSA-N ethyl 4-amino-2,3-bis(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidine-6-carboxylate Chemical compound N1=C2OC(C(=O)OCC)=CC2=C(N)N(C=2C=CC(OC)=CC=2)C1C1=CC=C(OC)C=C1 RNBVNEFECGSALY-UHFFFAOYSA-N 0.000 claims description 3
• WAVJYYRQTYEFJB-UHFFFAOYSA-N methyl 3-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)-n-carbamoylanilino]benzoate Chemical compound COC(=O)C1=CC=CC(N(C(N)=O)C=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 WAVJYYRQTYEFJB-UHFFFAOYSA-N 0.000 claims description 3
• MNKKPEQUYUBALT-UHFFFAOYSA-N methyl 3-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C2N(C(N)=C3C=COC3=N2)C=2C=CC(OC)=CC=2)=C1 MNKKPEQUYUBALT-UHFFFAOYSA-N 0.000 claims description 3
• RPZUXIKKLVCPGM-UHFFFAOYSA-N methyl 3-[[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]sulfamoyl]thiophene-2-carboxylate Chemical compound S1C=CC(S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1C(=O)OC RPZUXIKKLVCPGM-UHFFFAOYSA-N 0.000 claims description 3
• UXKNXKRWXZFMLL-UHFFFAOYSA-N methyl 5-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]-2-(methylamino)benzoate Chemical compound C1=C(C(=O)OC)C(NC)=CC=C1C1N(C=2C=CC(OC)=CC=2)C(N)=C2C=COC2=N1 UXKNXKRWXZFMLL-UHFFFAOYSA-N 0.000 claims description 3
• HRNXGXLYLPQVFK-UHFFFAOYSA-N methyl 5-[[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]sulfamoyl]-4-methoxythiophene-3-carboxylate Chemical compound COC(=O)C1=CSC(S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1OC HRNXGXLYLPQVFK-UHFFFAOYSA-N 0.000 claims description 3
• MKPJBAZILXUFOI-UHFFFAOYSA-N n,n-dimethyl-3-(4-nitrophenyl)-2h-furo[2,3-d]pyrimidin-4-amine Chemical compound CN(C)C1=C2C=COC2=NCN1C1=CC=C([N+]([O-])=O)C=C1 MKPJBAZILXUFOI-UHFFFAOYSA-N 0.000 claims description 3
• KPRBAGCTESMZGW-UHFFFAOYSA-N n-[3-(4-aminofuro[2,3-d]pyrimidin-2-yl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2N=C3OC=CC3=C(N)N=2)=C1 KPRBAGCTESMZGW-UHFFFAOYSA-N 0.000 claims description 3
• UNSBAWQWKPVKHC-UHFFFAOYSA-N n-[3-[4-[4-amino-2-(3-sulfamoylphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C=CC(=CC=2)N2C(=C3C=COC3=NC2C=2C=C(C=CC=2)S(N)(=O)=O)N)=C1 UNSBAWQWKPVKHC-UHFFFAOYSA-N 0.000 claims description 3
• WEQIATPCRNAGKE-UHFFFAOYSA-N n-[3-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=C(NC(C)=O)C=CC=2)C(N)=C2C=COC2=N1 WEQIATPCRNAGKE-UHFFFAOYSA-N 0.000 claims description 3
• PIQYKXSGSCMKSU-UHFFFAOYSA-N n-[3-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]phenyl]-2-morpholin-4-ylethanesulfonamide Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=CC(NS(=O)(=O)CCN2CCOCC2)=C1 PIQYKXSGSCMKSU-UHFFFAOYSA-N 0.000 claims description 3
• HYJCNPOOFCYASW-UHFFFAOYSA-N n-[3-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=CC(NC(C)=O)=C1 HYJCNPOOFCYASW-UHFFFAOYSA-N 0.000 claims description 3
• ZKWZRARHIUSSOP-UHFFFAOYSA-N n-[3-[4-amino-3-[4-(3-fluorophenyl)phenyl]-2h-furo[2,3-d]pyrimidin-2-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C2N(C(N)=C3C=COC3=N2)C=2C=CC(=CC=2)C=2C=C(F)C=CC=2)=C1 ZKWZRARHIUSSOP-UHFFFAOYSA-N 0.000 claims description 3
• ACBNMVBOHZFURU-UHFFFAOYSA-N n-[3-[[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]methoxy]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1COC1=CC=CC(NC(C)=O)=C1 ACBNMVBOHZFURU-UHFFFAOYSA-N 0.000 claims description 3
• IJRRCIFWIOFKDY-UHFFFAOYSA-N n-[4-(4-amino-2-pyridin-3-yl-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,3-dichlorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NC(C=2C=NC=CC=2)N1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl IJRRCIFWIOFKDY-UHFFFAOYSA-N 0.000 claims description 3
• JCQYZIBHCNDINQ-UHFFFAOYSA-N n-[4-(4-amino-2-pyridin-3-yl-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-fluorobenzamide Chemical compound NC1=C2C=COC2=NC(C=2C=NC=CC=2)N1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1 JCQYZIBHCNDINQ-UHFFFAOYSA-N 0.000 claims description 3
• AKVWSORXUZGPPZ-UHFFFAOYSA-N n-[4-(4-amino-2-pyridin-3-yl-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-fluorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NC(C=2C=NC=CC=2)N1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1 AKVWSORXUZGPPZ-UHFFFAOYSA-N 0.000 claims description 3
• WRRGLLFAKNAYQN-UHFFFAOYSA-N n-[4-(4-amino-2-pyridin-3-yl-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]thiophene-2-sulfonamide Chemical compound NC1=C2C=COC2=NC(C=2C=NC=CC=2)N1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CS1 WRRGLLFAKNAYQN-UHFFFAOYSA-N 0.000 claims description 3
• GKJYBAQFCDMZNI-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1,2-dimethylimidazole-4-sulfonamide Chemical compound CN1C(C)=NC(S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 GKJYBAQFCDMZNI-UHFFFAOYSA-N 0.000 claims description 3
• BLXVFVSURRLUSL-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-(4-methylphenyl)methanesulfonamide Chemical compound C1=CC(C)=CC=C1CS(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 BLXVFVSURRLUSL-UHFFFAOYSA-N 0.000 claims description 3
• PMOKHVQPBDEOEA-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-[2-chloro-5-(trifluoromethyl)phenyl]methanesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)CC1=CC(C(F)(F)F)=CC=C1Cl PMOKHVQPBDEOEA-UHFFFAOYSA-N 0.000 claims description 3
• XXTLWOVKNPERCA-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]methanesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)CC1=CC(C(F)(F)F)=CC=C1F XXTLWOVKNPERCA-UHFFFAOYSA-N 0.000 claims description 3
• HVDYOWZSRCANJU-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]cyclopropane-1-carboxamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)C1(C=2C=C(C=CC=2)C(F)(F)F)CC1 HVDYOWZSRCANJU-UHFFFAOYSA-N 0.000 claims description 3
• AOJGGTGYMNRHQL-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,1,3-benzothiadiazole-4-sulfonamide Chemical compound C1=CC2=NSN=C2C(S(=O)(=O)NC2=CC=C(C=C2)N2CN=C3OC=CC3=C2N)=C1 AOJGGTGYMNRHQL-UHFFFAOYSA-N 0.000 claims description 3
• FZHWTZYRGXTQNT-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,1,3-benzoxadiazole-4-sulfonamide Chemical compound C1=CC2=NON=C2C(S(=O)(=O)NC2=CC=C(C=C2)N2CN=C3OC=CC3=C2N)=C1 FZHWTZYRGXTQNT-UHFFFAOYSA-N 0.000 claims description 3
• NHJCVLGVMUFBKO-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,3,5,6-tetramethylbenzenesulfonamide Chemical compound CC1=CC(C)=C(C)C(S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1C NHJCVLGVMUFBKO-UHFFFAOYSA-N 0.000 claims description 3
• HXHQGGQLAIRAOS-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,3-dichlorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl HXHQGGQLAIRAOS-UHFFFAOYSA-N 0.000 claims description 3
• CYHLOTTUXVPZDU-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,3-dihydro-1,4-benzodioxine-6-sulfonamide Chemical compound O1CCOC2=CC(S(=O)(=O)NC3=CC=C(C=C3)N3CN=C4OC=CC4=C3N)=CC=C21 CYHLOTTUXVPZDU-UHFFFAOYSA-N 0.000 claims description 3
• OMTCJSOGTVPKNM-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 OMTCJSOGTVPKNM-UHFFFAOYSA-N 0.000 claims description 3
• UFKACPBYEDIPGN-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,4-dichloro-5-methylbenzenesulfonamide Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1Cl UFKACPBYEDIPGN-UHFFFAOYSA-N 0.000 claims description 3
• VGIZLNJLPFTMEX-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,4-dichlorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1Cl VGIZLNJLPFTMEX-UHFFFAOYSA-N 0.000 claims description 3
• BJPDVAATMKZWBN-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,5-dibromo-3,6-difluorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=C(F)C(Br)=CC(F)=C1Br BJPDVAATMKZWBN-UHFFFAOYSA-N 0.000 claims description 3
• RPRLMMBRUXKWRW-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,5-dichlorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC=C1Cl RPRLMMBRUXKWRW-UHFFFAOYSA-N 0.000 claims description 3
• KJPSVQCQVBURPN-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,5-dimethoxybenzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 KJPSVQCQVBURPN-UHFFFAOYSA-N 0.000 claims description 3
• VQQAFMHEFAJKQS-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,5-dimethylbenzenesulfonamide Chemical compound CC1=CC=C(C)C(S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 VQQAFMHEFAJKQS-UHFFFAOYSA-N 0.000 claims description 3
• ALCFJLIVEOYYNV-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,6-dichloro-4-(trifluoromethyl)benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ALCFJLIVEOYYNV-UHFFFAOYSA-N 0.000 claims description 3
• PDCMXIWLZWPJFO-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2,6-dichlorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=C(Cl)C=CC=C1Cl PDCMXIWLZWPJFO-UHFFFAOYSA-N 0.000 claims description 3
• SHWMNSKTLKCIFR-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2-(2,5-dichlorothiophen-3-yl)sulfonylacetamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)CS(=O)(=O)C=1C=C(Cl)SC=1Cl SHWMNSKTLKCIFR-UHFFFAOYSA-N 0.000 claims description 3
• ARDNMOUVCDSGLJ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 ARDNMOUVCDSGLJ-UHFFFAOYSA-N 0.000 claims description 3
• BVKFBHFTWUUBFI-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2-(5-chlorothiophen-2-yl)sulfonylacetamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)CS(=O)(=O)C1=CC=C(Cl)S1 BVKFBHFTWUUBFI-UHFFFAOYSA-N 0.000 claims description 3
• YVWUVDOODZQECZ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)acetamide Chemical compound N=1C(CC(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C(C)OC=1C1=CC=CC=C1 YVWUVDOODZQECZ-UHFFFAOYSA-N 0.000 claims description 3
• ZCMRZWMCJIELBT-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2-(trifluoromethoxy)benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F ZCMRZWMCJIELBT-UHFFFAOYSA-N 0.000 claims description 3
• MWMYSMFKRWCECF-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2-[3,5-bis(trifluoromethyl)phenyl]acetamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 MWMYSMFKRWCECF-UHFFFAOYSA-N 0.000 claims description 3
• ASFIEKIKHKWGET-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2-chloro-4-cyanobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(C#N)C=C1Cl ASFIEKIKHKWGET-UHFFFAOYSA-N 0.000 claims description 3
• XWCNSXCBVOWMHD-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2-chloro-4-fluorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1Cl XWCNSXCBVOWMHD-UHFFFAOYSA-N 0.000 claims description 3
• HVYKYBQMFBVCGQ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2-methoxy-5-methylbenzenesulfonamide Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 HVYKYBQMFBVCGQ-UHFFFAOYSA-N 0.000 claims description 3
• WCRUSTALBFFSDZ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2-nitro-4-(trifluoromethyl)benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O WCRUSTALBFFSDZ-UHFFFAOYSA-N 0.000 claims description 3
• UUVVYUKEFHBYSY-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2-phenylethenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C=CC1=CC=CC=C1 UUVVYUKEFHBYSY-UHFFFAOYSA-N 0.000 claims description 3
• ONPWMTDLHMVPHA-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-2-thiophen-2-ylacetamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NC(=O)CC1=CC=CS1 ONPWMTDLHMVPHA-UHFFFAOYSA-N 0.000 claims description 3
• WRDYKKOGBRLDRP-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3,4-dichlorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 WRDYKKOGBRLDRP-UHFFFAOYSA-N 0.000 claims description 3
• OUKLEZFAYRWDPL-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3,5-bis(trifluoromethyl)benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OUKLEZFAYRWDPL-UHFFFAOYSA-N 0.000 claims description 3
• SLIYYLGMIZXYBI-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3,5-dichloro-2-hydroxybenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1O SLIYYLGMIZXYBI-UHFFFAOYSA-N 0.000 claims description 3
• ORMAVYBVKTUJPD-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3,5-dichlorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 ORMAVYBVKTUJPD-UHFFFAOYSA-N 0.000 claims description 3
• RVXLIIALODATIJ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3,5-dimethoxybenzenesulfonamide Chemical compound COC1=CC(OC)=CC(S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 RVXLIIALODATIJ-UHFFFAOYSA-N 0.000 claims description 3
• QTKHWQOXWVBBOV-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 QTKHWQOXWVBBOV-UHFFFAOYSA-N 0.000 claims description 3
• WQGYQDBZOIIFPF-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(4-chlorophenoxy)benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(C=1)=CC=CC=1OC1=CC=C(Cl)C=C1 WQGYQDBZOIIFPF-UHFFFAOYSA-N 0.000 claims description 3
• XXDLDBLAXRSNEH-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-(4-chlorophenyl)benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(C=1)=CC=CC=1C1=CC=C(Cl)C=C1 XXDLDBLAXRSNEH-UHFFFAOYSA-N 0.000 claims description 3
• DNUSPZXOEXOYQO-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-chloro-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 DNUSPZXOEXOYQO-UHFFFAOYSA-N 0.000 claims description 3
• BDNIRSHAMIQERM-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-chloro-4-fluorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(F)C(Cl)=C1 BDNIRSHAMIQERM-UHFFFAOYSA-N 0.000 claims description 3
• CEDNEVGJGIZPFI-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-chlorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1 CEDNEVGJGIZPFI-UHFFFAOYSA-N 0.000 claims description 3
• PEISDGASLOBFMH-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-fluorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 PEISDGASLOBFMH-UHFFFAOYSA-N 0.000 claims description 3
• VATPILHYLCPXAJ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-methoxybenzenesulfonamide Chemical compound COC1=CC=CC(S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 VATPILHYLCPXAJ-UHFFFAOYSA-N 0.000 claims description 3
• QZVKWHSULSUOSH-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4,5-dichlorothiophene-2-sulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(Cl)=C(Cl)S1 QZVKWHSULSUOSH-UHFFFAOYSA-N 0.000 claims description 3
• ALWFXJGYDJIBRC-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-(3,4-dichlorophenoxy)benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 ALWFXJGYDJIBRC-UHFFFAOYSA-N 0.000 claims description 3
• NZVDVJZJDHFYLI-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-(3,4-dichlorophenyl)benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C(Cl)=C1 NZVDVJZJDHFYLI-UHFFFAOYSA-N 0.000 claims description 3
• IVHSJCOJJOLZJZ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-(3,5-dichlorophenoxy)benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 IVHSJCOJJOLZJZ-UHFFFAOYSA-N 0.000 claims description 3
• ANZHDZDOZXQIQZ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-(benzenesulfonyl)thiophene-2-sulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(SC=1)=CC=1S(=O)(=O)C1=CC=CC=C1 ANZHDZDOZXQIQZ-UHFFFAOYSA-N 0.000 claims description 3
• FHFJWWUQAPNLKP-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-(trifluoromethoxy)benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 FHFJWWUQAPNLKP-UHFFFAOYSA-N 0.000 claims description 3
• TVVWEOATBWXLHL-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-[(2-chloro-1,3-thiazol-5-yl)methoxy]benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1OCC1=CN=C(Cl)S1 TVVWEOATBWXLHL-UHFFFAOYSA-N 0.000 claims description 3
• KXSQOMIHFXIVFD-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-bromo-2,5-difluorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(F)=C(Br)C=C1F KXSQOMIHFXIVFD-UHFFFAOYSA-N 0.000 claims description 3
• OAFVCUDMPFKYJL-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-bromo-2-(trifluoromethoxy)benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(Br)C=C1OC(F)(F)F OAFVCUDMPFKYJL-UHFFFAOYSA-N 0.000 claims description 3
• IJSXOVPJIGZCNB-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-bromo-2-ethylbenzenesulfonamide Chemical compound CCC1=CC(Br)=CC=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 IJSXOVPJIGZCNB-UHFFFAOYSA-N 0.000 claims description 3
• LUQHYHACNPKZKA-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-butoxybenzenesulfonamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 LUQHYHACNPKZKA-UHFFFAOYSA-N 0.000 claims description 3
• FWOSHVAJQRZKQO-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-butylbenzenesulfonamide Chemical compound C1=CC(CCCC)=CC=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 FWOSHVAJQRZKQO-UHFFFAOYSA-N 0.000 claims description 3
• UUPYUAHXXYLLLI-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-chloro-2,1,3-benzoxadiazole-7-sulfonamide Chemical compound C1=C(Cl)C2=NON=C2C(S(=O)(=O)NC2=CC=C(C=C2)N2CN=C3OC=CC3=C2N)=C1 UUPYUAHXXYLLLI-UHFFFAOYSA-N 0.000 claims description 3
• FKHCUNBDXPFVAJ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-cyanobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(C#N)C=C1 FKHCUNBDXPFVAJ-UHFFFAOYSA-N 0.000 claims description 3
• IMZBXDBTYUUGLZ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-ethylbenzenesulfonamide Chemical compound C1=CC(CC)=CC=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 IMZBXDBTYUUGLZ-UHFFFAOYSA-N 0.000 claims description 3
• PRJOBNHRRLCGML-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-fluorobenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1 PRJOBNHRRLCGML-UHFFFAOYSA-N 0.000 claims description 3
• MLRFIWLQMUTQAQ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 MLRFIWLQMUTQAQ-UHFFFAOYSA-N 0.000 claims description 3
• MXGZABPTHSACLN-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-phenyldiazenylbenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1N=NC1=CC=CC=C1 MXGZABPTHSACLN-UHFFFAOYSA-N 0.000 claims description 3
• FQVRRGBDAHVLKV-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-propan-2-ylbenzenesulfonamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 FQVRRGBDAHVLKV-UHFFFAOYSA-N 0.000 claims description 3
• SAPRKZVJYILSAO-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 SAPRKZVJYILSAO-UHFFFAOYSA-N 0.000 claims description 3
• WRAKHMRMCPFALM-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-pyridin-2-yloxybenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=N1 WRAKHMRMCPFALM-UHFFFAOYSA-N 0.000 claims description 3
• CDKFNRUOLRXSAF-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-pyridin-4-yloxybenzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=NC=C1 CDKFNRUOLRXSAF-UHFFFAOYSA-N 0.000 claims description 3
• YWPMAQZLZCWHCK-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-4-tert-butylbenzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 YWPMAQZLZCWHCK-UHFFFAOYSA-N 0.000 claims description 3
• RHKOPIQSWYAPMC-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-(1,2-oxazol-3-yl)thiophene-2-sulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(S1)=CC=C1C=1C=CON=1 RHKOPIQSWYAPMC-UHFFFAOYSA-N 0.000 claims description 3
• XJFNHGZOMMEQSH-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-(2-methyl-1,3-thiazol-4-yl)thiophene-2-sulfonamide Chemical compound S1C(C)=NC(C=2SC(=CC=2)S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=C1 XJFNHGZOMMEQSH-UHFFFAOYSA-N 0.000 claims description 3
• ARKSVRRPDYGRKC-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-(2-methylsulfanylpyrimidin-4-yl)thiophene-2-sulfonamide Chemical compound CSC1=NC=CC(C=2SC(=CC=2)S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=N1 ARKSVRRPDYGRKC-UHFFFAOYSA-N 0.000 claims description 3
• YECVNWFEJZXICF-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-(4-cyano-1-methyl-5-methylsulfanylpyrazol-3-yl)thiophene-2-sulfonamide Chemical compound CN1C(SC)=C(C#N)C(C=2SC(=CC=2)S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)=N1 YECVNWFEJZXICF-UHFFFAOYSA-N 0.000 claims description 3
• CVADHWLDXLNWSG-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-(thiadiazol-4-yl)thiophene-2-sulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(S1)=CC=C1C1=CSN=N1 CVADHWLDXLNWSG-UHFFFAOYSA-N 0.000 claims description 3
• UWPCNQRXOOQZQM-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]thiophene-2-sulfonamide Chemical compound C1=C(C(F)(F)F)N(C)N=C1C1=CC=C(S(=O)(=O)NC=2C=CC(=CC=2)N2C(=C3C=COC3=NC2)N)S1 UWPCNQRXOOQZQM-UHFFFAOYSA-N 0.000 claims description 3
• BQYCLMQBMFBMJA-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-[5-(trifluoromethyl)-1,2-oxazol-3-yl]thiophene-2-sulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(S1)=CC=C1C=1C=C(C(F)(F)F)ON=1 BQYCLMQBMFBMJA-UHFFFAOYSA-N 0.000 claims description 3
• JANFVTXYJGLQNC-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-[5-(trifluoromethyl)pyridin-2-yl]sulfonylthiophene-2-sulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(S1)=CC=C1S(=O)(=O)C1=CC=C(C(F)(F)F)C=N1 JANFVTXYJGLQNC-UHFFFAOYSA-N 0.000 claims description 3
• ITVMTZOMNVHKCE-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-[[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methyl]thiophene-2-sulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(S1)=CC=C1CC1=NC=C(C(F)(F)F)C=C1Cl ITVMTZOMNVHKCE-UHFFFAOYSA-N 0.000 claims description 3
• WEKYPMKUCPXMEE-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-bromo-2-methoxybenzenesulfonamide Chemical compound COC1=CC=C(Br)C=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 WEKYPMKUCPXMEE-UHFFFAOYSA-N 0.000 claims description 3
• QMDSSGHTAZNRAN-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-bromo-6-chloropyridine-3-sulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CN=C(Cl)C(Br)=C1 QMDSSGHTAZNRAN-UHFFFAOYSA-N 0.000 claims description 3
• BZSHYDYUUOYHSW-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-bromothiophene-2-sulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(Br)S1 BZSHYDYUUOYHSW-UHFFFAOYSA-N 0.000 claims description 3
• AKVYPNQLSSZFOX-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-chloro-1,3-dimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(Cl)=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 AKVYPNQLSSZFOX-UHFFFAOYSA-N 0.000 claims description 3
• VBSIACPEQTXNAN-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-chloro-2,1,3-benzoxadiazole-4-sulfonamide Chemical compound C1=CC2=NON=C2C(S(=O)(=O)NC2=CC=C(C=C2)N2CN=C3OC=CC3=C2N)=C1Cl VBSIACPEQTXNAN-UHFFFAOYSA-N 0.000 claims description 3
• KKYNCWBUIWJDAF-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-chloro-3-methyl-1-benzothiophene-2-sulfonamide Chemical compound C1N=C2OC=CC2=C(N)N1C(C=C1)=CC=C1NS(=O)(=O)C1=C(C)C2=CC(Cl)=CC=C2S1 KKYNCWBUIWJDAF-UHFFFAOYSA-N 0.000 claims description 3
• WYSIJEADONQPOU-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-chloronaphthalene-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)NC3=CC=C(C=C3)N3CN=C4OC=CC4=C3N)=CC=CC2=C1Cl WYSIJEADONQPOU-UHFFFAOYSA-N 0.000 claims description 3
• NXKBKFBDLZUBSP-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-5-fluoro-2-methylbenzenesulfonamide Chemical compound CC1=CC=C(F)C=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 NXKBKFBDLZUBSP-UHFFFAOYSA-N 0.000 claims description 3
• NGTCQZVNPYCSQY-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-6-(dimethylamino)naphthalene-1-sulfonamide Chemical compound C1N=C2OC=CC2=C(N)N1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC2=CC(N(C)C)=CC=C21 NGTCQZVNPYCSQY-UHFFFAOYSA-N 0.000 claims description 3
• JMSXLMBWUNFEBT-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-6-chloroimidazo[2,1-b][1,3]thiazole-5-sulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=C(Cl)N=C2N1C=CS2 JMSXLMBWUNFEBT-UHFFFAOYSA-N 0.000 claims description 3
• BGKPELMZIMICEQ-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]benzenesulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC=C1 BGKPELMZIMICEQ-UHFFFAOYSA-N 0.000 claims description 3
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• KIYICCOKLZKNRY-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]quinoline-8-sulfonamide Chemical compound C1=CN=C2C(S(=O)(=O)NC3=CC=C(C=C3)N3CN=C4OC=CC4=C3N)=CC=CC2=C1 KIYICCOKLZKNRY-UHFFFAOYSA-N 0.000 claims description 3
• JDAHSWZNEXYYDH-UHFFFAOYSA-N n-[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]thiophene-2-sulfonamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CS1 JDAHSWZNEXYYDH-UHFFFAOYSA-N 0.000 claims description 3
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• RLDUQWISZDVUJP-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-1-phenylcyclopropane-1-carboxamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)C1(C=2C=CC=CC=2)CC1 RLDUQWISZDVUJP-UHFFFAOYSA-N 0.000 claims description 3
• GMIRSNYGQVZRAC-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-2,5-dichlorothiophene-3-carboxamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)C=1C=C(Cl)SC=1Cl GMIRSNYGQVZRAC-UHFFFAOYSA-N 0.000 claims description 3
• XCCUUKWOSRKYCZ-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-2,5-difluorobenzamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)C1=CC(F)=CC=C1F XCCUUKWOSRKYCZ-UHFFFAOYSA-N 0.000 claims description 3
• BXSQJLQQTFDYFS-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-2,6-difluorobenzamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F BXSQJLQQTFDYFS-UHFFFAOYSA-N 0.000 claims description 3
• LBCZNPLRYCNPJJ-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-2-(2,5-difluorophenyl)acetamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)CC1=CC(F)=CC=C1F LBCZNPLRYCNPJJ-UHFFFAOYSA-N 0.000 claims description 3
• IZPBNCCFNCKGNP-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-2-(2,6-difluorophenyl)acetamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)CC1=C(F)C=CC=C1F IZPBNCCFNCKGNP-UHFFFAOYSA-N 0.000 claims description 3
• RNKZMENUQDOYFI-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-2-[2,4-bis(trifluoromethyl)phenyl]acetamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1C(F)(F)F RNKZMENUQDOYFI-UHFFFAOYSA-N 0.000 claims description 3
• XDJPZUIENDCZFU-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-2-[2-fluoro-5-(trifluoromethyl)phenyl]acetamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)CC1=CC(C(F)(F)F)=CC=C1F XDJPZUIENDCZFU-UHFFFAOYSA-N 0.000 claims description 3
• UPJMCISIRIGAPN-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-2-[3,5-bis(trifluoromethyl)phenyl]acetamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UPJMCISIRIGAPN-UHFFFAOYSA-N 0.000 claims description 3
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• IFIWIHWZORPGHF-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-5-tert-butyl-2-methylpyrazole-3-carboxamide Chemical compound CN1N=C(C(C)(C)C)C=C1C(=O)NC1=CC=C(N2C(=C3C=CSC3=NC2)N)C=C1 IFIWIHWZORPGHF-UHFFFAOYSA-N 0.000 claims description 3
• XZAGAGSBSSHKIR-UHFFFAOYSA-N n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]benzamide Chemical compound NC1=C2C=CSC2=NCN1C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1 XZAGAGSBSSHKIR-UHFFFAOYSA-N 0.000 claims description 3
• LUMFCAIYNYVDAH-UHFFFAOYSA-N n-[4-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-2-fluorobenzamide Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)C(N)=C2C=COC2=N1 LUMFCAIYNYVDAH-UHFFFAOYSA-N 0.000 claims description 3
• VNZJQBDCGFMMAK-UHFFFAOYSA-N n-[4-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]-3-fluorobenzamide Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(NC(=O)C=3C=C(F)C=CC=3)=CC=2)C(N)=C2C=COC2=N1 VNZJQBDCGFMMAK-UHFFFAOYSA-N 0.000 claims description 3
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• UNIGZOXZLKBTPD-UHFFFAOYSA-N n-[4-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]naphthalene-2-sulfonamide Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(NS(=O)(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)C(N)=C2C=COC2=N1 UNIGZOXZLKBTPD-UHFFFAOYSA-N 0.000 claims description 3
• NNYUCCWFSNAZEH-UHFFFAOYSA-N n-[4-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]phenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=C(NS(C)(=O)=O)C=C1 NNYUCCWFSNAZEH-UHFFFAOYSA-N 0.000 claims description 3
• YHQNJRRRRJZYDE-UHFFFAOYSA-N n-[5-[4-amino-3-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]-2-fluorophenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1N1C(N)=C2C=COC2=NC1C1=CC=C(F)C(NS(C)(=O)=O)=C1 YHQNJRRRRJZYDE-UHFFFAOYSA-N 0.000 claims description 3
• OPAORNWUCRCSBO-UHFFFAOYSA-N n-[5-[4-amino-3-(4-pyridin-2-ylphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]-2-fluorophenyl]methanesulfonamide Chemical compound C1=C(F)C(NS(=O)(=O)C)=CC(C2N(C(N)=C3C=COC3=N2)C=2C=CC(=CC=2)C=2N=CC=CC=2)=C1 OPAORNWUCRCSBO-UHFFFAOYSA-N 0.000 claims description 3
• SDDWTBIWAOPTOG-UHFFFAOYSA-N n-[5-[4-amino-3-(4-thiophen-3-ylphenyl)-2h-furo[2,3-d]pyrimidin-2-yl]-2-fluorophenyl]methanesulfonamide Chemical compound C1=C(F)C(NS(=O)(=O)C)=CC(C2N(C(N)=C3C=COC3=N2)C=2C=CC(=CC=2)C2=CSC=C2)=C1 SDDWTBIWAOPTOG-UHFFFAOYSA-N 0.000 claims description 3
• GLKXBNXOQXJNBG-UHFFFAOYSA-N n-[5-[4-amino-3-[4-(2,3-difluorophenyl)phenyl]-2h-furo[2,3-d]pyrimidin-2-yl]-2-fluorophenyl]methanesulfonamide Chemical compound C1=C(F)C(NS(=O)(=O)C)=CC(C2N(C(N)=C3C=COC3=N2)C=2C=CC(=CC=2)C=2C(=C(F)C=CC=2)F)=C1 GLKXBNXOQXJNBG-UHFFFAOYSA-N 0.000 claims description 3
• IQUAVQVFGQHNEY-UHFFFAOYSA-N n-[5-[[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]sulfamoyl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1S(=O)(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)N)C=C1 IQUAVQVFGQHNEY-UHFFFAOYSA-N 0.000 claims description 3
• QAHICYJHFSNOPV-UHFFFAOYSA-N n-[[5-[[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]sulfamoyl]thiophen-2-yl]methyl]-4-chlorobenzamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 QAHICYJHFSNOPV-UHFFFAOYSA-N 0.000 claims description 3
• IDSMLGTYVRNXBE-UHFFFAOYSA-N n-[[5-[[4-(4-amino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]sulfamoyl]thiophen-2-yl]methyl]benzamide Chemical compound NC1=C2C=COC2=NCN1C(C=C1)=CC=C1NS(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=CC=C1 IDSMLGTYVRNXBE-UHFFFAOYSA-N 0.000 claims description 3
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• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 3
• WWVNZJFLBWRBLV-RBUKOAKNSA-N (1r,2r)-n-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1([C@@H]2C[C@H]2C(=O)NC2=CC=C(C=C2)N2CN=C3SC=CC3=C2N)=CC=CC=C1 WWVNZJFLBWRBLV-RBUKOAKNSA-N 0.000 claims description 2
• WXXJHWPSQWHHEA-UHFFFAOYSA-N 1-[4-(4-amino-2h-thieno[2,3-d]pyrimidin-3-yl)phenyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(N2C(=C3C=CSC3=NC2)N)C=CC=1N(C(=O)N)C1=CC(C(F)(F)F)=CC=C1F WXXJHWPSQWHHEA-UHFFFAOYSA-N 0.000 claims description 2
• QQYRNHSHDKUSFK-UHFFFAOYSA-N 1-[4-(4-anilino-2h-furo[2,3-d]pyrimidin-3-yl)phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound FC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=C(N2C(=C3C=COC3=NC2)NC=2C=CC=CC=2)C=C1 QQYRNHSHDKUSFK-UHFFFAOYSA-N 0.000 claims description 2
• LZVXPEUDEOSJHY-UHFFFAOYSA-N 1-[[4-[4-amino-2-(4-methoxyphenyl)-2h-furo[2,3-d]pyrimidin-3-yl]phenyl]methyl]-1-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(CN(C(N)=O)C=3C(=CC=C(C=3)C(F)(F)F)F)=CC=2)C(N)=C2C=COC2=N1 LZVXPEUDEOSJHY-UHFFFAOYSA-N 0.000 claims description 2
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