JP2016526561A5 - - Google Patents
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- JP2016526561A5 JP2016526561A5 JP2016524672A JP2016524672A JP2016526561A5 JP 2016526561 A5 JP2016526561 A5 JP 2016526561A5 JP 2016524672 A JP2016524672 A JP 2016524672A JP 2016524672 A JP2016524672 A JP 2016524672A JP 2016526561 A5 JP2016526561 A5 JP 2016526561A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkylene
- nhch
- phenyl
- triazine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 180
- 125000002947 alkylene group Chemical group 0.000 claims description 119
- UCDSGVJLGDUWQF-UHFFFAOYSA-N methyl 2-[[1-[4-(cyclopropylamino)-6-(ethylamino)-1,3,5-triazin-2-yl]-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound N=1C(N2N=C(SCC(=O)OC)N=C2)=NC(NCC)=NC=1NC1CC1 UCDSGVJLGDUWQF-UHFFFAOYSA-N 0.000 claims description 119
- -1 2-aminoethoxy Chemical group 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 55
- 230000035772 mutation Effects 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- XCBWOFAJTBVSQW-UHFFFAOYSA-N n-[[4-[[[4-(cyclopropylamino)-6-pyridin-2-yl-1,3,5-triazin-2-yl]amino]methyl]cyclohexyl]methyl]-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCC1CCC(CNC=2N=C(N=C(NC3CC3)N=2)C=2N=CC=CC=2)CC1 XCBWOFAJTBVSQW-UHFFFAOYSA-N 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 29
- WJDUCVZJAKHDOA-UHFFFAOYSA-N 2-[[1-[4-(cyclopropylamino)-6-(ethylamino)-1,3,5-triazin-2-yl]-1,2,4-triazol-3-yl]sulfanyl]acetamide Chemical compound N=1C(N2N=C(SCC(N)=O)N=C2)=NC(NCC)=NC=1NC1CC1 WJDUCVZJAKHDOA-UHFFFAOYSA-N 0.000 claims description 28
- 206010028980 Neoplasm Diseases 0.000 claims description 26
- 201000011510 cancer Diseases 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- BADKRWJBDCZDGE-UHFFFAOYSA-N 2-chloro-n-[4-(cyclopropylamino)-6-pyridin-2-yl-1,3,5-triazin-2-yl]-4-methylsulfonylbenzamide Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)NC1=NC(NC2CC2)=NC(C=2N=CC=CC=2)=N1 BADKRWJBDCZDGE-UHFFFAOYSA-N 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 101001042041 Bos taurus Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial Proteins 0.000 claims description 19
- 101000960234 Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Proteins 0.000 claims description 19
- 102100039905 Isocitrate dehydrogenase [NADP] cytoplasmic Human genes 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims description 10
- 230000001419 dependent effect Effects 0.000 claims description 10
- 102000004190 Enzymes Human genes 0.000 claims description 9
- 108090000790 Enzymes Proteins 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- DAHUIPUHTPGWLB-UHFFFAOYSA-N 2-(oxan-4-ylimino)-6-phenyl-4-propan-2-yl-1,3-dihydro-1,3,5-triazin-4-amine Chemical compound C(C)(C)C1(NC(=NC(=N1)NC1CCOCC1)C1=CC=CC=C1)N DAHUIPUHTPGWLB-UHFFFAOYSA-N 0.000 claims description 4
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 4
- LITAUKSSPWVCRT-UHFFFAOYSA-N 4-[2-[[4-(5-aminopentylamino)-6-(3-fluorophenyl)-1,3,5-triazin-2-yl]amino]ethyl]phenol Chemical compound N=1C(C=2C=C(F)C=CC=2)=NC(NCCCCCN)=NC=1NCCC1=CC=C(O)C=C1 LITAUKSSPWVCRT-UHFFFAOYSA-N 0.000 claims description 4
- SLOLUFRSDBPPPI-UHFFFAOYSA-N 4-[2-[[4-(5-aminopentylamino)-6-(4-fluorophenyl)-1,3,5-triazin-2-yl]amino]ethyl]phenol Chemical compound N=1C(C=2C=CC(F)=CC=2)=NC(NCCCCCN)=NC=1NCCC1=CC=C(O)C=C1 SLOLUFRSDBPPPI-UHFFFAOYSA-N 0.000 claims description 4
- UQZXEHZIVCMLSE-UHFFFAOYSA-N COC1=CC=C(C=C1)CNC1=NC(=NC(=N1)NCC1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC(F)(F)F Chemical compound COC1=CC=C(C=C1)CNC1=NC(=NC(=N1)NCC1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC(F)(F)F UQZXEHZIVCMLSE-UHFFFAOYSA-N 0.000 claims description 4
- HHDURDUNUHMQJQ-UHFFFAOYSA-N Cc1ccc(NC(=O)Nc2ccc(Cl)c(c2)C(F)(F)F)cc1-c1nc(NCCCCN)nc(NCC(O)=O)n1 Chemical compound Cc1ccc(NC(=O)Nc2ccc(Cl)c(c2)C(F)(F)F)cc1-c1nc(NCCCCN)nc(NCC(O)=O)n1 HHDURDUNUHMQJQ-UHFFFAOYSA-N 0.000 claims description 4
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 4
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- LKSCULJAMHWSQK-UHFFFAOYSA-N n-[4-(4,6-diacetamido-1,3,5-triazin-2-yl)-1,2,5-oxadiazol-3-yl]acetamide Chemical compound CC(=O)NC1=NON=C1C1=NC(NC(C)=O)=NC(NC(C)=O)=N1 LKSCULJAMHWSQK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 4
- VMJOXGDGZFSOKX-UHFFFAOYSA-N O=C1C2CCCCC2C(=O)C2C(CCCC12)Nc1nc(NC2CCCC3C2C(=O)C2CCCCC2C3=O)nc(n1)-c1ccccc1 Chemical compound O=C1C2CCCCC2C(=O)C2C(CCCC12)Nc1nc(NC2CCCC3C2C(=O)C2CCCCC2C3=O)nc(n1)-c1ccccc1 VMJOXGDGZFSOKX-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- JSEZODAYDINJHU-UHFFFAOYSA-N ethyl 2-[5-[4,6-bis(diethylamino)-1,3,5-triazin-2-yl]tetrazol-2-yl]acetate Chemical compound CCOC(=O)CN1N=NC(C=2N=C(N=C(N=2)N(CC)CC)N(CC)CC)=N1 JSEZODAYDINJHU-UHFFFAOYSA-N 0.000 claims description 3
- HNGGQDHOALRLAE-UHFFFAOYSA-N n-[4-(benzylamino)-6-pyridin-2-yl-1,3,5-triazin-2-yl]-2-chloro-4-methylsulfonylbenzamide Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)NC1=NC(NCC=2C=CC=CC=2)=NC(C=2N=CC=CC=2)=N1 HNGGQDHOALRLAE-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- XBCWOPHYAHRFCZ-UHFFFAOYSA-N 3-[[6-(2,3-dihydro-1h-inden-2-ylamino)-2-pyridin-2-ylpyrimidin-4-yl]amino]propanoic acid Chemical compound N=1C(NCCC(=O)O)=CC(NC2CC3=CC=CC=C3C2)=NC=1C1=CC=CC=N1 XBCWOPHYAHRFCZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 125000006414 CCl Chemical group ClC* 0.000 claims description 2
- 208000005243 Chondrosarcoma Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000032612 Glial tumor Diseases 0.000 claims description 2
- 206010018338 Glioma Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims description 2
- NMELLUXIHPTMON-UHFFFAOYSA-N OCCNc1cc(NC2CC3CCC2C3)nc(n1)-c1ccccc1 Chemical compound OCCNc1cc(NC2CC3CCC2C3)nc(n1)-c1ccccc1 NMELLUXIHPTMON-UHFFFAOYSA-N 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 208000006990 cholangiocarcinoma Diseases 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- AERQMVYPVMXKOC-UHFFFAOYSA-N 6-(3-benzylsulfanyl-1,2,4-triazol-1-yl)-4-cyclopropyl-2-ethylimino-1,3-dihydro-1,3,5-triazin-4-amine Chemical compound C1(CC1)C1(NC(=NC(=N1)NCC)N1N=C(N=C1)SCC1=CC=CC=C1)N AERQMVYPVMXKOC-UHFFFAOYSA-N 0.000 claims 26
- LJVPQCPZMSVWLX-UHFFFAOYSA-N 4-cyclohexyl-2-cyclohexylimino-6-[3-(4-methoxyphenyl)-5-methylsulfanylpyrazol-1-yl]-1,3-dihydro-1,3,5-triazin-4-amine Chemical compound C1(CCCCC1)C1(NC(=NC(=N1)NC1CCCCC1)N1N=C(C=C1SC)C1=CC=C(C=C1)OC)N LJVPQCPZMSVWLX-UHFFFAOYSA-N 0.000 claims 22
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 9
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 6
- CZTUKRUNAVJHOD-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetraethyl-6-(2h-tetrazol-5-yl)-1,3,5-triazine-2,4-diamine Chemical compound CCN(CC)C1=NC(N(CC)CC)=NC(C2=NNN=N2)=N1 CZTUKRUNAVJHOD-UHFFFAOYSA-N 0.000 claims 2
- YJZLSPWOROZXFA-UHFFFAOYSA-N 2-n,4-n-dicyclohexyl-6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound C1CCCCC1NC1=NC(NC2CCCCC2)=NC(C=2C=CC=CC=2)=N1 YJZLSPWOROZXFA-UHFFFAOYSA-N 0.000 claims 2
- XSXCXRISLKQJNC-UHFFFAOYSA-N 4-cyclohexyl-2-cyclohexylimino-6-[3-(3,4-dimethoxyphenyl)-5-methylsulfanylpyrazol-1-yl]-1,3-dihydro-1,3,5-triazin-4-amine Chemical compound C1(CCCCC1)C1(NC(=NC(=N1)NC1CCCCC1)N1N=C(C=C1SC)C1=CC(=C(C=C1)OC)OC)N XSXCXRISLKQJNC-UHFFFAOYSA-N 0.000 claims 2
- YEKATQFXCDVMOM-UHFFFAOYSA-N 4-cyclohexyl-2-cyclohexylimino-6-[5-methylsulfanyl-3-(3,4,5-trimethoxyphenyl)pyrazol-1-yl]-1,3-dihydro-1,3,5-triazin-4-amine Chemical compound C1(CCCCC1)C1(NC(=NC(=N1)NC1CCCCC1)N1N=C(C=C1SC)C1=CC(=C(C(=C1)OC)OC)OC)N YEKATQFXCDVMOM-UHFFFAOYSA-N 0.000 claims 2
- QLORVYPGVIRKJK-UHFFFAOYSA-N CC(C)(C)NC1=NC(N=CN1)(CC2=CC=CC=C2)N Chemical compound CC(C)(C)NC1=NC(N=CN1)(CC2=CC=CC=C2)N QLORVYPGVIRKJK-UHFFFAOYSA-N 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- KKXUVEVBRGERMZ-UHFFFAOYSA-N 6-N-benzyl-4-cyclopentyl-2-phenyl-1H-pyrimidine-4,6-diamine Chemical compound C1(CCCC1)C1(NC(=NC(=C1)NCC1=CC=CC=C1)C1=CC=CC=C1)N KKXUVEVBRGERMZ-UHFFFAOYSA-N 0.000 claims 1
- BQDMPXSEKDAUOD-UHFFFAOYSA-N C(C)(CC)NC1=NC(=NC(=N1)NC(C)CC)C1=CC=CC=C1 Chemical compound C(C)(CC)NC1=NC(=NC(=N1)NC(C)CC)C1=CC=CC=C1 BQDMPXSEKDAUOD-UHFFFAOYSA-N 0.000 claims 1
- LAGOKAOEUMWHMF-UHFFFAOYSA-N N1(C=NC=C1)C1=NC(=NC(=N1)NC(C)C)NC(C)C Chemical compound N1(C=NC=C1)C1=NC(=NC(=N1)NC(C)C)NC(C)C LAGOKAOEUMWHMF-UHFFFAOYSA-N 0.000 claims 1
- 108090000854 Oxidoreductases Proteins 0.000 claims 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000009826 neoplastic cell growth Effects 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 101000599886 Homo sapiens Isocitrate dehydrogenase [NADP], mitochondrial Proteins 0.000 description 16
- 102100037845 Isocitrate dehydrogenase [NADP], mitochondrial Human genes 0.000 description 16
- 125000001188 haloalkyl group Chemical group 0.000 description 15
- 238000000034 method Methods 0.000 description 12
- HWXBTNAVRSUOJR-UHFFFAOYSA-N 2-hydroxyglutaric acid Chemical compound OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 description 11
- 108700028369 Alleles Proteins 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 102200116484 rs121913502 Human genes 0.000 description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 2
- OSYLJQVIKNRXPX-UHFFFAOYSA-N 6-(4-chlorophenyl)-2-N-[4-chloro-3-(trifluoromethyl)phenyl]-4-N-[3-(dimethylamino)propyl]-1,3,5-triazine-2,4-diamine Chemical compound CN(C)CCCNc1nc(Nc2ccc(Cl)c(c2)C(F)(F)F)nc(n1)-c1ccc(Cl)cc1 OSYLJQVIKNRXPX-UHFFFAOYSA-N 0.000 description 2
- CSANMBBDSJFENW-UHFFFAOYSA-N C1(CCCCC1)CNC1=NC(=NC(=N1)N)C1=CC=CC=C1 Chemical compound C1(CCCCC1)CNC1=NC(=NC(=N1)N)C1=CC=CC=C1 CSANMBBDSJFENW-UHFFFAOYSA-N 0.000 description 2
- 0 CC(*=C(C)C(N)=N)=C Chemical compound CC(*=C(C)C(N)=N)=C 0.000 description 2
- ZKLQURKJPPUQQI-UHFFFAOYSA-N CCCNc1nc(Nc2cc(NC(=O)Nc3ccc(Cl)c(c3)C(F)(F)F)ccc2C)nc(n1)-c1ccccc1 Chemical compound CCCNc1nc(Nc2cc(NC(=O)Nc3ccc(Cl)c(c3)C(F)(F)F)ccc2C)nc(n1)-c1ccccc1 ZKLQURKJPPUQQI-UHFFFAOYSA-N 0.000 description 2
- YXDJEDYZJRRTTN-UHFFFAOYSA-N CCN(CC)CCCNc1nc(Nc2cc(cc(c2)C(F)(F)F)C(F)(F)F)nc(n1)-c1ccc(Cl)cc1 Chemical compound CCN(CC)CCCNc1nc(Nc2cc(cc(c2)C(F)(F)F)C(F)(F)F)nc(n1)-c1ccc(Cl)cc1 YXDJEDYZJRRTTN-UHFFFAOYSA-N 0.000 description 2
- KCLBKETVXHZTQK-UHFFFAOYSA-N Cc1ccc(NC(=O)Nc2ccc(Cl)c(c2)C(F)(F)F)cc1Nc1nc(NCC(O)=O)nc(n1)-c1ccncc1 Chemical compound Cc1ccc(NC(=O)Nc2ccc(Cl)c(c2)C(F)(F)F)cc1Nc1nc(NCC(O)=O)nc(n1)-c1ccncc1 KCLBKETVXHZTQK-UHFFFAOYSA-N 0.000 description 2
- ZCUVULNGLKPRBV-UHFFFAOYSA-N Nc1cc(N)nc(n1)-c1ccnc(N)n1 Chemical compound Nc1cc(N)nc(n1)-c1ccnc(N)n1 ZCUVULNGLKPRBV-UHFFFAOYSA-N 0.000 description 2
- JWRUUYZHFGUQRJ-UHFFFAOYSA-N [[4-[[(4-amino-6-pyridin-4-yl-1,3,5-triazin-2-yl)amino]methoxymethylamino]-6-pyridin-4-yl-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound Nc1nc(NCOCNc2nc(nc(n2)-c2ccncc2)N(CO)CO)nc(n1)-c1ccncc1 JWRUUYZHFGUQRJ-UHFFFAOYSA-N 0.000 description 2
- GGYQDUIJPJUTJE-UHFFFAOYSA-N [[4-[[[4-[bis(hydroxymethyl)amino]-6-pyridin-4-yl-1,3,5-triazin-2-yl]amino]methoxymethyl-(hydroxymethyl)amino]-6-pyridin-4-yl-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)c1nc(NCOCN(CO)c2nc(nc(n2)-c2ccncc2)N(CO)CO)nc(n1)-c1ccncc1 GGYQDUIJPJUTJE-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- NZGRFUGPKHHITM-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-5-[[4-(dimethylamino)-6-pyridin-2-yl-1,3,5-triazin-2-yl]amino]-1,3,4-oxadiazole-2-carboxamide Chemical compound N=1C(C=2N=CC=CC=2)=NC(N(C)C)=NC=1NC(O1)=NN=C1C(=O)NC1=C(C)C=CC=C1Cl NZGRFUGPKHHITM-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000012163 sequencing technique Methods 0.000 description 2
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