KR20030013475A - 항암제로서의 치환된 트리아졸로피리미딘 - Google Patents

Info

Publication number

KR20030013475A

KR20030013475A KR1020027017998A KR20027017998A KR20030013475A KR 20030013475 A KR20030013475 A KR 20030013475A KR 1020027017998 A KR1020027017998 A KR 1020027017998A KR 20027017998 A KR20027017998 A KR 20027017998A KR 20030013475 A KR20030013475 A KR 20030013475A

Authority

KR

South Korea

Prior art keywords

chloro

carbon atoms

triazolo

substituted

pyrimidine

Prior art date

2000-06-30

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.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• -1 Substituted-triazolopyrimidines Chemical class 0.000 title claims description 414
• 239000002246 antineoplastic agent Substances 0.000 title description 7
• 238000000034 method Methods 0.000 claims abstract description 159
• 150000003839 salts Chemical class 0.000 claims abstract description 112
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 56
• 102000029749 Microtubule Human genes 0.000 claims abstract description 37
• 108091022875 Microtubule Proteins 0.000 claims abstract description 37
• 210000004688 microtubule Anatomy 0.000 claims abstract description 37
• 241000124008 Mammalia Species 0.000 claims abstract description 33
• 102000004243 Tubulin Human genes 0.000 claims abstract description 26
• 108090000704 Tubulin Proteins 0.000 claims abstract description 26
• 201000011510 cancer Diseases 0.000 claims abstract description 24
• 201000010099 disease Diseases 0.000 claims abstract description 22
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
• 210000004881 tumor cell Anatomy 0.000 claims abstract description 22
• YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 claims abstract description 20
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 14
• 230000005907 cancer growth Effects 0.000 claims abstract description 11
• 230000029115 microtubule polymerization Effects 0.000 claims abstract description 10
• 230000001737 promoting effect Effects 0.000 claims abstract description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 1494
• 125000000217 alkyl group Chemical group 0.000 claims description 405
• 150000001875 compounds Chemical class 0.000 claims description 201
• 125000003118 aryl group Chemical group 0.000 claims description 190
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 183
• 125000000623 heterocyclic group Chemical group 0.000 claims description 153
• 239000001257 hydrogen Substances 0.000 claims description 120
• 229910052739 hydrogen Inorganic materials 0.000 claims description 120
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 111
• 229910052736 halogen Inorganic materials 0.000 claims description 110
• 150000002367 halogens Chemical class 0.000 claims description 110
• 150000002431 hydrogen Chemical class 0.000 claims description 100
• 125000003545 alkoxy group Chemical group 0.000 claims description 95
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 85
• 125000003342 alkenyl group Chemical group 0.000 claims description 83
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 80
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 79
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 74
• 229910052757 nitrogen Inorganic materials 0.000 claims description 72
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 71
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 59
• 125000004414 alkyl thio group Chemical group 0.000 claims description 58
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 55
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
• 125000001188 haloalkyl group Chemical group 0.000 claims description 53
• 125000000304 alkynyl group Chemical group 0.000 claims description 52
• 125000003282 alkyl amino group Chemical group 0.000 claims description 46
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 45
• 229930012538 Paclitaxel Natural products 0.000 claims description 44
• 229960001592 paclitaxel Drugs 0.000 claims description 44
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 44
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 43
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
• 229910052799 carbon Inorganic materials 0.000 claims description 35
• 229920006395 saturated elastomer Polymers 0.000 claims description 35
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 30
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 30
• 150000001412 amines Chemical class 0.000 claims description 30
• 125000004104 aryloxy group Chemical group 0.000 claims description 30
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 30
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 25
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 25
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
• 125000006413 ring segment Chemical group 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 206010048723 Multiple-drug resistance Diseases 0.000 claims description 20
• 235000011449 Rosa Nutrition 0.000 claims description 20
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 20
• MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 claims description 18
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 16
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 15
• 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 15
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 15
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 13
• MGSIJDCPNJZOHF-RXMQYKEDSA-N 5-chloro-6-(2,4,6-trifluorophenyl)-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C1=C(F)C=C(F)C=C1F MGSIJDCPNJZOHF-RXMQYKEDSA-N 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 claims description 11
• 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 11
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000001544 thienyl group Chemical group 0.000 claims description 11
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 10
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 10
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 10
• 125000001246 bromo group Chemical group Br* 0.000 claims description 10
• 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 10
• 229930192474 thiophene Natural products 0.000 claims description 10
• 108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 claims description 8
• 201000001441 melanoma Diseases 0.000 claims description 7
• GTEBBTHHSMCNLM-UHFFFAOYSA-N 1-[5-chloro-6-(2,6-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]piperidin-4-ol Chemical compound C1CC(O)CCN1C1=C(C=2C(=CC=CC=2F)F)C(Cl)=NC2=NC=NN12 GTEBBTHHSMCNLM-UHFFFAOYSA-N 0.000 claims description 6
• CRPYWWHIJDLSTO-UHFFFAOYSA-N 1-[5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-2-methylpropan-1-one Chemical compound ClC1=NC=2N(C(=C1C1=C(C=CC=C1F)Cl)C(C(C)C)=O)N=CN=2 CRPYWWHIJDLSTO-UHFFFAOYSA-N 0.000 claims description 6
• NDETWNVQSIGUEE-UHFFFAOYSA-N 1-[5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]piperidin-3-ol Chemical compound C1C(O)CCCN1C1=C(C=2C(=CC=CC=2F)Cl)C(Cl)=NC2=NC=NN12 NDETWNVQSIGUEE-UHFFFAOYSA-N 0.000 claims description 6
• ZLKJXDNWUUQWBE-UHFFFAOYSA-N 2-[2-[4-[5-chloro-7-(1,1,1-trifluoropropan-2-ylamino)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-3,5-difluorophenoxy]ethoxy]ethanol Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(F)(F)F)=C1C1=C(F)C=C(OCCOCCO)C=C1F ZLKJXDNWUUQWBE-UHFFFAOYSA-N 0.000 claims description 6
• YTNSPEHQRWJGFH-UHFFFAOYSA-N 2-[5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]cyclohexan-1-one Chemical compound FC1=CC=CC(Cl)=C1C1=C(C2C(CCCC2)=O)N2N=CN=C2N=C1Cl YTNSPEHQRWJGFH-UHFFFAOYSA-N 0.000 claims description 6
• VKYGVBIOSZIYTO-UHFFFAOYSA-N 2-[5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]cyclohexane-1,3-dione Chemical class FC1=CC=CC(Cl)=C1C1=C(C2C(CCCC2=O)=O)N2N=CN=C2N=C1Cl VKYGVBIOSZIYTO-UHFFFAOYSA-N 0.000 claims description 6
• 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 6
• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• SFLOEJCGLGZMSQ-UHFFFAOYSA-N 4-[5-chloro-2-methyl-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-n,n-dimethylaniline Chemical compound C1CC(C)CCN1C1=C(C=2C=CC(=CC=2)N(C)C)C(Cl)=NC2=NC(C)=NN12 SFLOEJCGLGZMSQ-UHFFFAOYSA-N 0.000 claims description 6
• FZNQTWBCKVVUIM-UHFFFAOYSA-N 4-[5-chloro-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]thiomorpholine Chemical compound FC1=CC=C(F)C(C2=C(N3N=CN=C3N=C2Cl)N2CCSCC2)=C1F FZNQTWBCKVVUIM-UHFFFAOYSA-N 0.000 claims description 6
• UKTHLFZADQGTRQ-UHFFFAOYSA-N 4-[5-chloro-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]thiomorpholine Chemical compound FC1=CC(F)=CC(F)=C1C1=C(N2CCSCC2)N2N=CN=C2N=C1Cl UKTHLFZADQGTRQ-UHFFFAOYSA-N 0.000 claims description 6
• BLYBLJPCQQPEBD-UHFFFAOYSA-N 4-[5-chloro-6-(2,6-difluoro-4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]thiomorpholine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(N2CCSCC2)N2N=CN=C2N=C1Cl BLYBLJPCQQPEBD-UHFFFAOYSA-N 0.000 claims description 6
• YMDOQLMBGVKKPQ-UHFFFAOYSA-N 4-[5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]thiomorpholine Chemical compound FC1=CC=CC(Cl)=C1C1=C(N2CCSCC2)N2N=CN=C2N=C1Cl YMDOQLMBGVKKPQ-UHFFFAOYSA-N 0.000 claims description 6
• AJRPWIWXUKJGOV-UHFFFAOYSA-N 4-[5-chloro-6-(2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]thiomorpholine Chemical compound CC1=CC=CC=C1C1=C(N2CCSCC2)N2N=CN=C2N=C1Cl AJRPWIWXUKJGOV-UHFFFAOYSA-N 0.000 claims description 6
• IEZIKFHQZDHUHG-UHFFFAOYSA-N 4-[5-chloro-6-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]thiomorpholine Chemical compound C1=CC(OC)=CC=C1C1=C(N2CCSCC2)N2N=CN=C2N=C1Cl IEZIKFHQZDHUHG-UHFFFAOYSA-N 0.000 claims description 6
• RDIIYPVBESNMLF-UHFFFAOYSA-N 4-[5-chloro-6-(4-methylsulfanylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]thiomorpholine Chemical compound C1=CC(SC)=CC=C1C1=C(N2CCSCC2)N2N=CN=C2N=C1Cl RDIIYPVBESNMLF-UHFFFAOYSA-N 0.000 claims description 6
• CESUFHBRZYUIDO-UHFFFAOYSA-N 4-[5-chloro-6-[2,6-dichloro-4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]thiomorpholine Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1C1=C(N2CCSCC2)N2N=CN=C2N=C1Cl CESUFHBRZYUIDO-UHFFFAOYSA-N 0.000 claims description 6
• SGVGNPLZXLJADQ-UHFFFAOYSA-N 4-[5-chloro-7-(1,1,1-trifluoropropan-2-ylamino)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-2,5-difluorophenol Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(F)(F)F)=C1C1=CC(F)=C(O)C=C1F SGVGNPLZXLJADQ-UHFFFAOYSA-N 0.000 claims description 6
• DPBAZTXCBFUYEZ-UHFFFAOYSA-N 4-[5-chloro-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]aniline Chemical compound C1CC(C)CCN1C1=C(C=2C=CC(N)=CC=2)C(Cl)=NC2=NC=NN12 DPBAZTXCBFUYEZ-UHFFFAOYSA-N 0.000 claims description 6
• AEZLKIUQUZLWKO-UHFFFAOYSA-N 5,7-bis(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=NC2=NC=NN2C(N2CCC(C)CC2)=C1C1=C(F)C=C(F)C=C1F AEZLKIUQUZLWKO-UHFFFAOYSA-N 0.000 claims description 6
• CMXWOJVGBNBRFC-UHFFFAOYSA-N 5-azido-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C(=CC=CC=2F)Cl)C(N=[N+]=[N-])=NC2=NC=NN12 CMXWOJVGBNBRFC-UHFFFAOYSA-N 0.000 claims description 6
• BQIKGIGDSXZNDB-UHFFFAOYSA-N 5-bromo-6-(2-chloro-6-fluorophenyl)-7-cyclohexyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(C2CCCCC2)N2N=CN=C2N=C1Br BQIKGIGDSXZNDB-UHFFFAOYSA-N 0.000 claims description 6
• MESPVDYKOFLJOU-UHFFFAOYSA-N 5-bromo-6-(2-chloro-6-fluorophenyl)-7-propan-2-ylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound BrC1=NC2=NC=NN2C(SC(C)C)=C1C1=C(F)C=CC=C1Cl MESPVDYKOFLJOU-UHFFFAOYSA-N 0.000 claims description 6
• BIRHFURHLBTDIJ-UHFFFAOYSA-N 5-bromo-6-(4-bromophenyl)-n,n-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound BrC1=NC2=NC=NN2C(N(C)C)=C1C1=CC=C(Br)C=C1 BIRHFURHLBTDIJ-UHFFFAOYSA-N 0.000 claims description 6
• RCAXZVCYSZWLLO-UHFFFAOYSA-N 5-bromo-n,n-dimethyl-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound BrC1=NC2=NC=NN2C(N(C)C)=C1C1=CC=C(C(F)(F)F)C=C1 RCAXZVCYSZWLLO-UHFFFAOYSA-N 0.000 claims description 6
• FJONCHDDFCUSOR-UHFFFAOYSA-N 5-chloro-6-(2,3-difluoro-4-methoxyphenyl)-n-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=C(F)C(OC)=CC=C1C1=C(NC(C)C(F)(F)F)N2N=CN=C2N=C1Cl FJONCHDDFCUSOR-UHFFFAOYSA-N 0.000 claims description 6
• MGSIJDCPNJZOHF-UHFFFAOYSA-N 5-chloro-6-(2,4,6-trifluorophenyl)-n-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(F)(F)F)=C1C1=C(F)C=C(F)C=C1F MGSIJDCPNJZOHF-UHFFFAOYSA-N 0.000 claims description 6
• WFLDHBJSYRXNCZ-UHFFFAOYSA-N 5-chloro-6-(2,4,6-trifluorophenyl)-n-(2,2,2-trifluoro-1-phenylethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(F)=CC(F)=C1C1=C(NC(C=2C=CC=CC=2)C(F)(F)F)N2N=CN=C2N=C1Cl WFLDHBJSYRXNCZ-UHFFFAOYSA-N 0.000 claims description 6
• CIRDYBZXJOXSJV-UHFFFAOYSA-N 5-chloro-6-(2,4-dichlorophenyl)-n,n-diethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC)CC)=C1C1=CC=C(Cl)C=C1Cl CIRDYBZXJOXSJV-UHFFFAOYSA-N 0.000 claims description 6
• UXMMONFJUDINOY-UHFFFAOYSA-N 5-chloro-6-(2,4-difluorophenyl)-n-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(F)(F)F)=C1C1=CC=C(F)C=C1F UXMMONFJUDINOY-UHFFFAOYSA-N 0.000 claims description 6
• QLZOURQTVGTIJN-UHFFFAOYSA-N 5-chloro-6-(2,5-difluoro-4-methoxyphenyl)-n-(3,3-dimethylbutan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(F)C(OC)=CC(F)=C1C1=C(NC(C)C(C)(C)C)N2N=CN=C2N=C1Cl QLZOURQTVGTIJN-UHFFFAOYSA-N 0.000 claims description 6
• PVALWCUNZYACID-UHFFFAOYSA-N 5-chloro-6-(2,5-difluorophenyl)-n-(3-methylbut-2-enyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical class ClC1=NC2=NC=NN2C(NCC=C(C)C)=C1C1=CC(F)=CC=C1F PVALWCUNZYACID-UHFFFAOYSA-N 0.000 claims description 6
• FFLDVXITEPDAMP-UHFFFAOYSA-N 5-chloro-6-(2,5-difluorophenyl)-n-dodecyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NCCCCCCCCCCCC)=C1C1=CC(F)=CC=C1F FFLDVXITEPDAMP-UHFFFAOYSA-N 0.000 claims description 6
• CAGWLXFZBVZAMD-UHFFFAOYSA-N 5-chloro-6-(2,6-dichloro-4-fluorophenyl)-7-(3,3,3-trifluoropropyl)-1h-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC(F)(F)CCC1(N)N2NC=NC2=NC(Cl)=C1C1=C(Cl)C=C(F)C=C1Cl CAGWLXFZBVZAMD-UHFFFAOYSA-N 0.000 claims description 6
• FXYRPYPEWDTROQ-UHFFFAOYSA-N 5-chloro-6-(2,6-dichlorophenyl)-7-(2-methylpyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound CC1CCCN1C1=C(C=2C(=CC=CC=2Cl)Cl)C(Cl)=NC2=NC=NN12 FXYRPYPEWDTROQ-UHFFFAOYSA-N 0.000 claims description 6
• IGOXXNKUMDLTAJ-UHFFFAOYSA-N 5-chloro-6-(2,6-difluoro-4-methoxyphenyl)-7-(2-methylpropyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(CC(C)C)N2N=CN=C2N=C1Cl IGOXXNKUMDLTAJ-UHFFFAOYSA-N 0.000 claims description 6
• KIZNKXZSGPWQEC-UHFFFAOYSA-N 5-chloro-6-(2,6-difluoro-4-methoxyphenyl)-7-(3,6-dihydro-2h-pyridin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(N2CC=CCC2)N2N=CN=C2N=C1Cl KIZNKXZSGPWQEC-UHFFFAOYSA-N 0.000 claims description 6
• MYMWXRSCPMFIRX-UHFFFAOYSA-N 5-chloro-6-(2,6-difluoro-4-methoxyphenyl)-7-(3-methylbut-3-enyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(CCC(C)=C)N2N=CN=C2N=C1Cl MYMWXRSCPMFIRX-UHFFFAOYSA-N 0.000 claims description 6
• QITDMJGAHSSQDW-UHFFFAOYSA-N 5-chloro-6-(2,6-difluoro-4-methoxyphenyl)-7-(4-fluorocyclohexyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(C2CCC(F)CC2)N2N=CN=C2N=C1Cl QITDMJGAHSSQDW-UHFFFAOYSA-N 0.000 claims description 6
• BSAGLPQUFXGCDO-UHFFFAOYSA-N 5-chloro-6-(2,6-difluoro-4-methoxyphenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(N2CCC(C)CC2)N2N=CN=C2N=C1Cl BSAGLPQUFXGCDO-UHFFFAOYSA-N 0.000 claims description 6
• WAXOUSAHDFOGDU-UHFFFAOYSA-N 5-chloro-6-(2,6-difluoro-4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(N)N2N=CN=C2N=C1Cl WAXOUSAHDFOGDU-UHFFFAOYSA-N 0.000 claims description 6
• SSFYIXVSMRMOFY-UHFFFAOYSA-N 5-chloro-6-(2,6-difluoro-4-methoxyphenyl)-n-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(NC(C)C(F)(F)F)N2N=CN=C2N=C1Cl SSFYIXVSMRMOFY-UHFFFAOYSA-N 0.000 claims description 6
• OUTWTSDRXGYYLY-UHFFFAOYSA-N 5-chloro-6-(2,6-difluoro-4-methoxyphenyl)-n-(3,3-dimethylbutan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(NC(C)C(C)(C)C)N2N=CN=C2N=C1Cl OUTWTSDRXGYYLY-UHFFFAOYSA-N 0.000 claims description 6
• SSFYIXVSMRMOFY-LURJTMIESA-N 5-chloro-6-(2,6-difluoro-4-methoxyphenyl)-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl SSFYIXVSMRMOFY-LURJTMIESA-N 0.000 claims description 6
• YSYJXCYWSFDAIA-UHFFFAOYSA-N 5-chloro-6-(2,6-difluoro-4-methoxyphenyl)-n-ethyl-n-(2-methylprop-2-enyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)=C)CC)=C1C1=C(F)C=C(OC)C=C1F YSYJXCYWSFDAIA-UHFFFAOYSA-N 0.000 claims description 6
• RBKJETFGUYUBAQ-UHFFFAOYSA-N 5-chloro-6-(2,6-difluoro-4-prop-1-enoxyphenyl)-n-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OC=CC)=CC(F)=C1C1=C(NC(C)C(F)(F)F)N2N=CN=C2N=C1Cl RBKJETFGUYUBAQ-UHFFFAOYSA-N 0.000 claims description 6
• SBIUBGCNIDPIAW-UHFFFAOYSA-N 5-chloro-6-(2,6-difluorophenyl)-7-(2,4-dimethylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound CC1CC(C)CCN1C1=C(C=2C(=CC=CC=2F)F)C(Cl)=NC2=NC=NN12 SBIUBGCNIDPIAW-UHFFFAOYSA-N 0.000 claims description 6
• FDIXYOXUKNLXHD-UHFFFAOYSA-N 5-chloro-6-(2,6-difluorophenyl)-7-(2,5-dihydropyrrol-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(F)=C1C1=C(N2CC=CC2)N2N=CN=C2N=C1Cl FDIXYOXUKNLXHD-UHFFFAOYSA-N 0.000 claims description 6
• VYFCMOGEWCYBFN-UHFFFAOYSA-N 5-chloro-6-(2,6-difluorophenyl)-7-(3,6-dihydro-2h-pyridin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(F)=C1C1=C(N2CC=CCC2)N2N=CN=C2N=C1Cl VYFCMOGEWCYBFN-UHFFFAOYSA-N 0.000 claims description 6
• ORTLEUXFZUFBEJ-UHFFFAOYSA-N 5-chloro-6-(2,6-difluorophenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C(=CC=CC=2F)F)C(Cl)=NC2=NC=NN12 ORTLEUXFZUFBEJ-UHFFFAOYSA-N 0.000 claims description 6
• ZXOXPJAURQOXRE-UHFFFAOYSA-N 5-chloro-6-(2,6-difluorophenyl)-n-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(F)(F)F)=C1C1=C(F)C=CC=C1F ZXOXPJAURQOXRE-UHFFFAOYSA-N 0.000 claims description 6
• ZTYFIAMJYNAYMK-UHFFFAOYSA-N 5-chloro-6-(2,6-difluorophenyl)-n-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC=CC(F)=C1C1=C(NCC(F)(F)F)N2N=CN=C2N=C1Cl ZTYFIAMJYNAYMK-UHFFFAOYSA-N 0.000 claims description 6
• FOFXDVFZGATFAF-UHFFFAOYSA-N 5-chloro-6-(2-chloro-4-nitrophenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C(=CC(=CC=2)[N+]([O-])=O)Cl)C(Cl)=NC2=NC=NN12 FOFXDVFZGATFAF-UHFFFAOYSA-N 0.000 claims description 6
• ZZIMENLIXWNLKM-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluoro-4-methoxyphenyl)-n-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=CC(OC)=CC(F)=C1C1=C(NC(C)C(F)(F)F)N2N=CN=C2N=C1Cl ZZIMENLIXWNLKM-UHFFFAOYSA-N 0.000 claims description 6
• WLONTJKIWGLQRV-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2,2,2-trifluoroethylsulfanyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(SCC(F)(F)F)N2N=CN=C2N=C1Cl WLONTJKIWGLQRV-UHFFFAOYSA-N 0.000 claims description 6
• FCYAWBJNSHOEBN-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2-ethylimidazol-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound CCC1=NC=CN1C1=C(C=2C(=CC=CC=2F)Cl)C(Cl)=NC2=NC=NN12 FCYAWBJNSHOEBN-UHFFFAOYSA-N 0.000 claims description 6
• RKDKPWZCLSTOLG-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2-methoxyphenyl)sulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound COC1=CC=CC=C1SC1=C(C=2C(=CC=CC=2F)Cl)C(Cl)=NC2=NC=NN12 RKDKPWZCLSTOLG-UHFFFAOYSA-N 0.000 claims description 6
• YNXBBKBOYAIAPL-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound CC1CCCCN1C1=C(C=2C(=CC=CC=2F)Cl)C(Cl)=NC2=NC=NN12 YNXBBKBOYAIAPL-UHFFFAOYSA-N 0.000 claims description 6
• BQALQKNNJZCSGK-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2-pyrrolidin-1-ylcyclohexen-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(C=2CCCCC=2N2CCCC2)N2N=CN=C2N=C1Cl BQALQKNNJZCSGK-UHFFFAOYSA-N 0.000 claims description 6
• GGAUWTJCQYYWNO-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2-pyrrolidin-1-ylcyclopenten-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(C=2CCCC=2N2CCCC2)N2N=CN=C2N=C1Cl GGAUWTJCQYYWNO-UHFFFAOYSA-N 0.000 claims description 6
• QHQRQZDUNJWYAC-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(3,3,3-trifluoropropyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(CCC(F)(F)F)N2N=CN=C2N=C1Cl QHQRQZDUNJWYAC-UHFFFAOYSA-N 0.000 claims description 6
• BVGNTXZKHZNBLQ-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(3-methylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound CC1=CC=CC(C=2N3N=CN=C3N=C(Cl)C=2C=2C(=CC=CC=2F)Cl)=C1 BVGNTXZKHZNBLQ-UHFFFAOYSA-N 0.000 claims description 6
• BOEKOMPYWWMYTL-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4,4-difluoropiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(N2CCC(F)(F)CC2)N2N=CN=C2N=C1Cl BOEKOMPYWWMYTL-UHFFFAOYSA-N 0.000 claims description 6
• MXSJZACALJJCOL-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-chlorophenyl)sulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(SC=2C=CC(Cl)=CC=2)N2N=CN=C2N=C1Cl MXSJZACALJJCOL-UHFFFAOYSA-N 0.000 claims description 6
• BPJQBJUREDQRRC-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C(=CC=CC=2F)Cl)C(Cl)=NC2=NC=NN12 BPJQBJUREDQRRC-UHFFFAOYSA-N 0.000 claims description 6
• IVNGFMHPKCQDCU-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-pyridin-2-ylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(N2CCN(CC2)C=2N=CC=CC=2)N2N=CN=C2N=C1Cl IVNGFMHPKCQDCU-UHFFFAOYSA-N 0.000 claims description 6
• XNYKJOKNQIWWAD-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(chloromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(CCl)N2N=CN=C2N=C1Cl XNYKJOKNQIWWAD-UHFFFAOYSA-N 0.000 claims description 6
• FUJZHAQOLUQNMW-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(methoxymethyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound ClC1=NC2=NC=NN2C(COC)=C1C1=C(F)C=CC=C1Cl FUJZHAQOLUQNMW-UHFFFAOYSA-N 0.000 claims description 6
• WSZRAWYJRXQOGY-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(oxolan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(C2OCCC2)N2N=CN=C2N=C1Cl WSZRAWYJRXQOGY-UHFFFAOYSA-N 0.000 claims description 6
• XJOWVPWCWGETBR-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-[4-(2-chlorophenyl)piperazin-1-yl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(N2CCN(CC2)C=2C(=CC=CC=2)Cl)N2N=CN=C2N=C1Cl XJOWVPWCWGETBR-UHFFFAOYSA-N 0.000 claims description 6
• MGLHHKAKOJSUGQ-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-[4-(4-methoxyphenyl)-3-methylpiperazin-1-yl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1N1C(C)CN(C=2N3N=CN=C3N=C(Cl)C=2C=2C(=CC=CC=2F)Cl)CC1 MGLHHKAKOJSUGQ-UHFFFAOYSA-N 0.000 claims description 6
• PCIKQCFUVFYPIK-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-[4-(trifluoromethyl)piperidin-1-yl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(N2CCC(CC2)C(F)(F)F)N2N=CN=C2N=C1Cl PCIKQCFUVFYPIK-UHFFFAOYSA-N 0.000 claims description 6
• ROHKXFFGDLZLLB-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-cyclohexyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(C2CCCCC2)N2N=CN=C2N=C1Cl ROHKXFFGDLZLLB-UHFFFAOYSA-N 0.000 claims description 6
• JOCZOPWWGIKUDU-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-hexyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound ClC1=NC2=NC=NN2C(CCCCCC)=C1C1=C(F)C=CC=C1Cl JOCZOPWWGIKUDU-UHFFFAOYSA-N 0.000 claims description 6
• NIBCHXRBBQOCNT-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-pentyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound ClC1=NC2=NC=NN2C(CCCCC)=C1C1=C(F)C=CC=C1Cl NIBCHXRBBQOCNT-UHFFFAOYSA-N 0.000 claims description 6
• XLGUKBAFAUVQDA-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(C=2C=CC=CC=2)N2N=CN=C2N=C1Cl XLGUKBAFAUVQDA-UHFFFAOYSA-N 0.000 claims description 6
• JLZLLWYSRPNXDF-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-propan-2-ylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound ClC1=NC2=NC=NN2C(SC(C)C)=C1C1=C(F)C=CC=C1Cl JLZLLWYSRPNXDF-UHFFFAOYSA-N 0.000 claims description 6
• NBBVRMQSRMRZMQ-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N)=C1C1=C(F)C=CC=C1Cl NBBVRMQSRMRZMQ-UHFFFAOYSA-N 0.000 claims description 6
• SNQSAXXKIGXLAY-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-n-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(F)(F)F)=C1C1=C(F)C=CC=C1Cl SNQSAXXKIGXLAY-UHFFFAOYSA-N 0.000 claims description 6
• QJCBRGBHFJWHAL-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-n-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC=CC(Cl)=C1C1=C(NCC(F)(F)F)N2N=CN=C2N=C1Cl QJCBRGBHFJWHAL-UHFFFAOYSA-N 0.000 claims description 6
• IHHZKKKAZISPPZ-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-n-(cyclopropylmethyl)-n-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical class FC=1C=CC=C(Cl)C=1C=1C(Cl)=NC2=NC=NN2C=1N(CCC)CC1CC1 IHHZKKKAZISPPZ-UHFFFAOYSA-N 0.000 claims description 6
• NPGZLYAKDPTREU-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-n-[(3,4,5-trimethoxyphenyl)methyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound COC1=C(OC)C(OC)=CC(CNC=2N3N=CN=C3N=C(Cl)C=2C=2C(=CC=CC=2F)Cl)=C1 NPGZLYAKDPTREU-UHFFFAOYSA-N 0.000 claims description 6
• RKTAVXBAGDUSAH-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-n-[(4-chlorophenyl)methyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC=CC(Cl)=C1C1=C(NCC=2C=CC(Cl)=CC=2)N2N=CN=C2N=C1Cl RKTAVXBAGDUSAH-UHFFFAOYSA-N 0.000 claims description 6
• JMJUBLQIYAVCRI-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-n-cyclopentyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC=CC(Cl)=C1C1=C(NC2CCCC2)N2N=CN=C2N=C1Cl JMJUBLQIYAVCRI-UHFFFAOYSA-N 0.000 claims description 6
• NCKYCWBKMGHHAX-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-n-ethyl-n-(2-methylprop-2-enyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)=C)CC)=C1C1=C(F)C=CC=C1Cl NCKYCWBKMGHHAX-UHFFFAOYSA-N 0.000 claims description 6
• CBMNAEPOPODSJX-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-n-heptan-3-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(CC)CCCC)=C1C1=C(F)C=CC=C1Cl CBMNAEPOPODSJX-UHFFFAOYSA-N 0.000 claims description 6
• MQAHESQTAIQCJG-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-n-hexyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NCCCCCC)=C1C1=C(F)C=CC=C1Cl MQAHESQTAIQCJG-UHFFFAOYSA-N 0.000 claims description 6
• VRLWKWBRQAFGQD-UHFFFAOYSA-N 5-chloro-6-(2-chlorophenyl)-7-(2-methylpyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound CC1CCCN1C1=C(C=2C(=CC=CC=2)Cl)C(Cl)=NC2=NC=NN12 VRLWKWBRQAFGQD-UHFFFAOYSA-N 0.000 claims description 6
• QEVYFQFZGRYJSE-UHFFFAOYSA-N 5-chloro-6-(2-chlorophenyl)-n-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(F)(F)F)=C1C1=CC=CC=C1Cl QEVYFQFZGRYJSE-UHFFFAOYSA-N 0.000 claims description 6
• VEXAAHOGZUDHBM-UHFFFAOYSA-N 5-chloro-6-(2-chlorophenyl)-n-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NCC(F)(F)F)=C1C1=CC=CC=C1Cl VEXAAHOGZUDHBM-UHFFFAOYSA-N 0.000 claims description 6
• YIOPYCRLZFIJNI-UHFFFAOYSA-N 5-chloro-6-(2-chlorophenyl)-n-cyclopentyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=CC=CC=C1C1=C(NC2CCCC2)N2N=CN=C2N=C1Cl YIOPYCRLZFIJNI-UHFFFAOYSA-N 0.000 claims description 6
• MRILIOKBZFSWBI-UHFFFAOYSA-N 5-chloro-6-(2-fluoro-4-nitrophenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C(=CC(=CC=2)[N+]([O-])=O)F)C(Cl)=NC2=NC=NN12 MRILIOKBZFSWBI-UHFFFAOYSA-N 0.000 claims description 6
• JONZZFBTWKUVPH-UHFFFAOYSA-N 5-chloro-6-(2-methylphenyl)-n,n-bis(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical class CC1=CC=CC=C1C1=C(N(CC(F)(F)F)CC(F)(F)F)N2N=CN=C2N=C1Cl JONZZFBTWKUVPH-UHFFFAOYSA-N 0.000 claims description 6
• YZFWYERNRSQZOA-UHFFFAOYSA-N 5-chloro-6-(2-methylphenyl)-n-(2-methylpropyl)-n-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(F)(F)F)CC(C)C)=C1C1=CC=CC=C1C YZFWYERNRSQZOA-UHFFFAOYSA-N 0.000 claims description 6
• QKFJRXRFZQTHGA-UHFFFAOYSA-N 5-chloro-6-(3,4-difluorophenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C=C(F)C(F)=CC=2)C(Cl)=NC2=NC=NN12 QKFJRXRFZQTHGA-UHFFFAOYSA-N 0.000 claims description 6
• SJIISGPAISLNMI-UHFFFAOYSA-N 5-chloro-6-(3,4-difluorophenyl)-n,n-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(C)C)=C1C1=CC=C(F)C(F)=C1 SJIISGPAISLNMI-UHFFFAOYSA-N 0.000 claims description 6
• BBDASBLAYVMIGV-UHFFFAOYSA-N 5-chloro-6-(3,4-difluorophenyl)-n-propan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C)=C1C1=CC=C(F)C(F)=C1 BBDASBLAYVMIGV-UHFFFAOYSA-N 0.000 claims description 6
• PCBIWSHVLDFWOP-UHFFFAOYSA-N 5-chloro-6-(3,5-difluorophenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C=C(F)C=C(F)C=2)C(Cl)=NC2=NC=NN12 PCBIWSHVLDFWOP-UHFFFAOYSA-N 0.000 claims description 6
• FCUVMKVQWOMTHU-UHFFFAOYSA-N 5-chloro-6-(3-chloro-4-methoxyphenyl)-7-(2-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(N2C(CCCC2)C)N2N=CN=C2N=C1Cl FCUVMKVQWOMTHU-UHFFFAOYSA-N 0.000 claims description 6
• IIRKITAITGNZPX-UHFFFAOYSA-N 5-chloro-6-(3-chloro-4-methoxyphenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(N2CCC(C)CC2)N2N=CN=C2N=C1Cl IIRKITAITGNZPX-UHFFFAOYSA-N 0.000 claims description 6
• MZMNJILSZILXCA-UHFFFAOYSA-N 5-chloro-6-(4-chloro-2,3,5,6-tetrafluorophenyl)-n-cyclopentyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical class FC1=C(Cl)C(F)=C(F)C(C2=C(N3N=CN=C3N=C2Cl)NC2CCCC2)=C1F MZMNJILSZILXCA-UHFFFAOYSA-N 0.000 claims description 6
• MMXVFEPEPFRIGX-UHFFFAOYSA-N 5-chloro-6-(4-methoxyphenyl)-7-(3-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(N2CC(C)CCC2)N2N=CN=C2N=C1Cl MMXVFEPEPFRIGX-UHFFFAOYSA-N 0.000 claims description 6
• RQJHHNFPGFFLRM-UHFFFAOYSA-N 5-chloro-6-(4-methoxyphenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(N2CCC(C)CC2)N2N=CN=C2N=C1Cl RQJHHNFPGFFLRM-UHFFFAOYSA-N 0.000 claims description 6
• OJTIIHCPNJCVFL-UHFFFAOYSA-N 5-chloro-6-(4-methoxyphenyl)-7-(4-propan-2-ylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(N2CCC(CC2)C(C)C)N2N=CN=C2N=C1Cl OJTIIHCPNJCVFL-UHFFFAOYSA-N 0.000 claims description 6
• HOOUKSDPWMYKJA-UHFFFAOYSA-N 5-chloro-6-(4-methoxyphenyl)-7-piperidin-1-yl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(N2CCCCC2)N2N=CN=C2N=C1Cl HOOUKSDPWMYKJA-UHFFFAOYSA-N 0.000 claims description 6
• OXBYJQOSLHEYPT-UHFFFAOYSA-N 5-chloro-6-(4-phenylmethoxyphenyl)-n-propan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C)=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 OXBYJQOSLHEYPT-UHFFFAOYSA-N 0.000 claims description 6
• ABNFJJRKTAZTJA-UHFFFAOYSA-N 5-chloro-6-[(2-chloro-6-fluorophenyl)methyl]-7-(oxolan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1CC1=C(C2OCCC2)N2N=CN=C2N=C1Cl ABNFJJRKTAZTJA-UHFFFAOYSA-N 0.000 claims description 6
• AEJWYWNYMXDYMN-UHFFFAOYSA-N 5-chloro-6-[2,6-dichloro-4-(trifluoromethyl)phenyl]-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)C(Cl)=NC2=NC=NN12 AEJWYWNYMXDYMN-UHFFFAOYSA-N 0.000 claims description 6
• BPOFWMGDRRRSNN-UHFFFAOYSA-N 5-chloro-6-[2,6-dichloro-4-(trifluoromethyl)phenyl]-n-ethyl-n-(2-methylprop-2-enyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)=C)CC)=C1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl BPOFWMGDRRRSNN-UHFFFAOYSA-N 0.000 claims description 6
• GMMOUJMJQOSZMW-UHFFFAOYSA-N 5-chloro-6-[2,6-difluoro-4-(2-fluoroethoxy)phenyl]-n-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(F)(F)F)=C1C1=C(F)C=C(OCCF)C=C1F GMMOUJMJQOSZMW-UHFFFAOYSA-N 0.000 claims description 6
• ICTMQSIMNCRWTR-UHFFFAOYSA-N 5-chloro-6-[2,6-difluoro-4-(2-fluoroethoxy)phenyl]-n-ethyl-n-(2-methylprop-2-enyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)=C)CC)=C1C1=C(F)C=C(OCCF)C=C1F ICTMQSIMNCRWTR-UHFFFAOYSA-N 0.000 claims description 6
• QWLWXTFMVIENDL-UHFFFAOYSA-N 5-chloro-6-[2,6-difluoro-4-(3-methylbut-2-enoxy)phenyl]-n-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(F)(F)F)=C1C1=C(F)C=C(OCC=C(C)C)C=C1F QWLWXTFMVIENDL-UHFFFAOYSA-N 0.000 claims description 6
• PMMLJEMGWCRFLA-UHFFFAOYSA-N 5-chloro-7-(2,4-dimethylpiperidin-1-yl)-6-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(N2C(CC(C)CC2)C)N2N=CN=C2N=C1Cl PMMLJEMGWCRFLA-UHFFFAOYSA-N 0.000 claims description 6
• CIOWHZHLTRWBTI-UHFFFAOYSA-N 5-chloro-7-(2-methylpiperidin-1-yl)-6-(4-phenoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound CC1CCCCN1C1=C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)C(Cl)=NC2=NC=NN12 CIOWHZHLTRWBTI-UHFFFAOYSA-N 0.000 claims description 6
• SMXIIQRBEBKHSP-UHFFFAOYSA-N 5-chloro-7-(2-methylpiperidin-1-yl)-6-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound CC1CCCCN1C1=C(C=2C=C(C=CC=2)C(F)(F)F)C(Cl)=NC2=NC=NN12 SMXIIQRBEBKHSP-UHFFFAOYSA-N 0.000 claims description 6
• LCOITPHRFWCCHI-UHFFFAOYSA-N 5-chloro-7-(4-chloropiperidin-1-yl)-6-(2,6-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(F)=C1C1=C(N2CCC(Cl)CC2)N2N=CN=C2N=C1Cl LCOITPHRFWCCHI-UHFFFAOYSA-N 0.000 claims description 6
• POPPXRSZVAUZIR-UHFFFAOYSA-N 5-chloro-7-(4-chloropiperidin-1-yl)-6-[2-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC(F)(F)C1=CC=CC=C1C1=C(N2CCC(Cl)CC2)N2N=CN=C2N=C1Cl POPPXRSZVAUZIR-UHFFFAOYSA-N 0.000 claims description 6
• KJRGIZZXBSYZHN-UHFFFAOYSA-N 5-chloro-7-(4-fluorocyclohexyl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(F)CCC1C1=C(C=2C(=CC(F)=CC=2F)F)C(Cl)=NC2=NC=NN12 KJRGIZZXBSYZHN-UHFFFAOYSA-N 0.000 claims description 6
• SPFXJKNCUJDRSG-UHFFFAOYSA-N 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C(=C(F)C=CC=2F)F)C(Cl)=NC2=NC=NN12 SPFXJKNCUJDRSG-UHFFFAOYSA-N 0.000 claims description 6
• XIWUERJAZPDEFK-UHFFFAOYSA-N 5-chloro-7-(4-methylpiperidin-1-yl)-6-(4-methylsulfanylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(N2CCC(C)CC2)N2N=CN=C2N=C1Cl XIWUERJAZPDEFK-UHFFFAOYSA-N 0.000 claims description 6
• BIDBATDHZLIGJX-UHFFFAOYSA-N 5-chloro-7-(4-methylpiperidin-1-yl)-6-(4-phenoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)C(Cl)=NC2=NC=NN12 BIDBATDHZLIGJX-UHFFFAOYSA-N 0.000 claims description 6
• LGQOUTVZKJWOHQ-UHFFFAOYSA-N 5-chloro-7-(4-methylpiperidin-1-yl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C=CC(OC(F)(F)F)=CC=2)C(Cl)=NC2=NC=NN12 LGQOUTVZKJWOHQ-UHFFFAOYSA-N 0.000 claims description 6
• HENBEXAETRMTKR-UHFFFAOYSA-N 5-chloro-7-(furan-2-ylmethylsulfanyl)-6-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(SCC=2OC=CC=2)N2N=CN=C2N=C1Cl HENBEXAETRMTKR-UHFFFAOYSA-N 0.000 claims description 6
• CRFVAAWVECVZEI-UHFFFAOYSA-N 5-chloro-7-cyclohex-3-en-1-yl-6-(2,6-difluoro-4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(C2CC=CCC2)N2N=CN=C2N=C1Cl CRFVAAWVECVZEI-UHFFFAOYSA-N 0.000 claims description 6
• GWDVJRAZUUNRKU-UHFFFAOYSA-N 5-chloro-7-cyclohexyl-6-(2,3,4,5,6-pentafluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1C1=C(C2CCCCC2)N2N=CN=C2N=C1Cl GWDVJRAZUUNRKU-UHFFFAOYSA-N 0.000 claims description 6
• RSZUUQLSQMBDTJ-UHFFFAOYSA-N 5-chloro-7-cyclohexyl-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(F)=CC(F)=C1C1=C(C2CCCCC2)N2N=CN=C2N=C1Cl RSZUUQLSQMBDTJ-UHFFFAOYSA-N 0.000 claims description 6
• BWMACKGXIHXFDK-UHFFFAOYSA-N 5-chloro-7-cyclohexyl-6-(2,6-difluoro-4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(C2CCCCC2)N2N=CN=C2N=C1Cl BWMACKGXIHXFDK-UHFFFAOYSA-N 0.000 claims description 6
• JXWCUHJNRLREOE-UHFFFAOYSA-N 5-chloro-7-piperidin-1-yl-6-[2-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC(F)(F)C1=CC=CC=C1C1=C(N2CCCCC2)N2N=CN=C2N=C1Cl JXWCUHJNRLREOE-UHFFFAOYSA-N 0.000 claims description 6
• NKUQPJZCXNVRHJ-UHFFFAOYSA-N 5-chloro-n,n-diethyl-6-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC)CC)=C1C1=CC=C(OC)C=C1 NKUQPJZCXNVRHJ-UHFFFAOYSA-N 0.000 claims description 6
• WMVBCJOROQPLGR-UHFFFAOYSA-N 5-chloro-n,n-diethyl-6-(4-methylsulfanylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC)CC)=C1C1=CC=C(SC)C=C1 WMVBCJOROQPLGR-UHFFFAOYSA-N 0.000 claims description 6
• FJPWIYFFIMKPRH-UHFFFAOYSA-N 5-chloro-n-(1,1,1-trifluorobutan-2-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(CC)C(F)(F)F)=C1C1=C(F)C=C(F)C=C1F FJPWIYFFIMKPRH-UHFFFAOYSA-N 0.000 claims description 6
• NFOMNKVDJTWWBR-UHFFFAOYSA-N 5-chloro-n-(2-methylpropyl)-n-(2,2,2-trifluoroethyl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(F)(F)F)CC(C)C)=C1C1=C(F)C=C(F)C=C1F NFOMNKVDJTWWBR-UHFFFAOYSA-N 0.000 claims description 6
• AQHOFZNSUGRKJO-UHFFFAOYSA-N 5-chloro-n-(3,3-dimethylbutan-2-yl)-6-(2,3,4,5,6-pentafluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(C)(C)C)=C1C1=C(F)C(F)=C(F)C(F)=C1F AQHOFZNSUGRKJO-UHFFFAOYSA-N 0.000 claims description 6
• OBXPVEWIIHRBQS-UHFFFAOYSA-N 5-chloro-n-(3,3-dimethylbutan-2-yl)-6-(2,4,5-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(C)(C)C)=C1C1=CC(F)=C(F)C=C1F OBXPVEWIIHRBQS-UHFFFAOYSA-N 0.000 claims description 6
• FYICFNFWBRPEGD-UHFFFAOYSA-N 5-chloro-n-(3,3-dimethylbutan-2-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(C)(C)C)=C1C1=C(F)C=C(F)C=C1F FYICFNFWBRPEGD-UHFFFAOYSA-N 0.000 claims description 6
• RHVRPRYTTZLPDH-UHFFFAOYSA-N 5-chloro-n-(3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(C)(C)C)=C1C1=CC=C(F)C=C1 RHVRPRYTTZLPDH-UHFFFAOYSA-N 0.000 claims description 6
• PCKLITCBRYRMGL-UHFFFAOYSA-N 5-chloro-n-(3-chloropropyl)-n-methyl-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CCCCl)C)=C1C1=C(F)C=CC(F)=C1F PCKLITCBRYRMGL-UHFFFAOYSA-N 0.000 claims description 6
• XNASJYDFVYMKKY-UHFFFAOYSA-N 5-chloro-n-(3-methylbut-2-enyl)-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NCC=C(C)C)=C1C1=CC=CC=C1 XNASJYDFVYMKKY-UHFFFAOYSA-N 0.000 claims description 6
• BMVBXRJVLUMWNN-UHFFFAOYSA-N 5-chloro-n-(3-methylbutan-2-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical class ClC1=NC2=NC=NN2C(NC(C)C(C)C)=C1C1=C(F)C=C(F)C=C1F BMVBXRJVLUMWNN-UHFFFAOYSA-N 0.000 claims description 6
• HPOVKGXWEWZKOZ-UHFFFAOYSA-N 5-chloro-n-(4-methyl-3-nitrophenyl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1NC1=C(C=2C(=CC(F)=CC=2F)F)C(Cl)=NC2=NC=NN12 HPOVKGXWEWZKOZ-UHFFFAOYSA-N 0.000 claims description 6
• GKGUBFAKULWBKS-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-6-(2,6-difluoro-4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(NC2CCCC2)N2N=CN=C2N=C1Cl GKGUBFAKULWBKS-UHFFFAOYSA-N 0.000 claims description 6
• NXABRQKNTAEKQW-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-6-(4-methylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(C)=CC=C1C1=C(NC2CCCC2)N2N=CN=C2N=C1Cl NXABRQKNTAEKQW-UHFFFAOYSA-N 0.000 claims description 6
• SJSPBWVBLBNOMY-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-6-(4-phenylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C=1C(Cl)=NC2=NC=NN2C=1NC1CCCC1 SJSPBWVBLBNOMY-UHFFFAOYSA-N 0.000 claims description 6
• LTBWDAYYRQXMDS-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-n-methyl-6-(2,3,4,5,6-pentafluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC=1C(F)=C(F)C(F)=C(F)C=1C=1C(Cl)=NC2=NC=NN2C=1N(C)C1CCCC1 LTBWDAYYRQXMDS-UHFFFAOYSA-N 0.000 claims description 6
• FURIQOISIOXEGE-UHFFFAOYSA-N 5-chloro-n-ethyl-6-(2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NCC)=C1C1=CC=CC=C1C FURIQOISIOXEGE-UHFFFAOYSA-N 0.000 claims description 6
• IWNDRYAYJQOQPZ-UHFFFAOYSA-N 5-chloro-n-ethyl-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NCC)=C1C1=CC=C(C(F)(F)F)C=C1 IWNDRYAYJQOQPZ-UHFFFAOYSA-N 0.000 claims description 6
• COAXHOXILSDEDX-UHFFFAOYSA-N 5-chloro-n-ethyl-n-(2-methylprop-2-enyl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)=C)CC)=C1C1=C(F)C=CC(F)=C1F COAXHOXILSDEDX-UHFFFAOYSA-N 0.000 claims description 6
• KFDSTIPXIDEYLZ-UHFFFAOYSA-N 5-chloro-n-ethyl-n-(2-methylprop-2-enyl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)=C)CC)=C1C1=C(F)C=C(F)C=C1F KFDSTIPXIDEYLZ-UHFFFAOYSA-N 0.000 claims description 6
• CXVYTLURKRUESE-UHFFFAOYSA-N 5-chloro-n-ethyl-n-(2-methylprop-2-enyl)-6-(4-nitrophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)=C)CC)=C1C1=CC=C([N+]([O-])=O)C=C1 CXVYTLURKRUESE-UHFFFAOYSA-N 0.000 claims description 6
• WYWOKJUPKHVTRB-UHFFFAOYSA-N 5-chloro-n-ethyl-n-(2-methylpropyl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)C)CC)=C1C1=C(F)C=C(F)C=C1F WYWOKJUPKHVTRB-UHFFFAOYSA-N 0.000 claims description 6
• LLVIWUADDWKGOH-UHFFFAOYSA-N 5-chloro-n-methyl-n-(2-methylprop-2-enyl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)=C)C)=C1C1=C(F)C=C(F)C=C1F LLVIWUADDWKGOH-UHFFFAOYSA-N 0.000 claims description 6
• ODMYVVGPYUMRHH-UHFFFAOYSA-N 5-chloro-n-methyl-n-(3-methylbutan-2-yl)-6-(2,3,4,5,6-pentafluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(C)C(C)C(C)C)=C1C1=C(F)C(F)=C(F)C(F)=C1F ODMYVVGPYUMRHH-UHFFFAOYSA-N 0.000 claims description 6
• WNJQIJUNSZQWEK-UHFFFAOYSA-N 5-chloro-n-methyl-n-propan-2-yl-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(C)C(C)C)=C1C1=C(F)C=C(F)C=C1F WNJQIJUNSZQWEK-UHFFFAOYSA-N 0.000 claims description 6
• UAQVLXOFPMZVOM-UHFFFAOYSA-N 5-chloro-n-propan-2-yl-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C)=C1C1=C(F)C=CC(F)=C1F UAQVLXOFPMZVOM-UHFFFAOYSA-N 0.000 claims description 6
• ZPAZTZUBJNKHAU-UHFFFAOYSA-N 5-chloro-n-propan-2-yl-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C)=C1C1=C(F)C=C(F)C=C1F ZPAZTZUBJNKHAU-UHFFFAOYSA-N 0.000 claims description 6
• AAAWHADHJQJXEJ-UHFFFAOYSA-N 5-chloro-n-propan-2-yl-6-[2-(trifluoromethylsulfanyl)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C)=C1C1=CC=CC=C1SC(F)(F)F AAAWHADHJQJXEJ-UHFFFAOYSA-N 0.000 claims description 6
• VMYNOUQSPZLRJW-UHFFFAOYSA-N 5-chloro-n-propan-2-yl-n-(2,2,2-trifluoroethyl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(F)(F)F)C(C)C)=C1C1=C(F)C=C(F)C=C1F VMYNOUQSPZLRJW-UHFFFAOYSA-N 0.000 claims description 6
• RHCXXPNZIQLEIB-UHFFFAOYSA-N 6,7-bis(4-methoxyphenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N2N=C(C)N=C2N=C1 RHCXXPNZIQLEIB-UHFFFAOYSA-N 0.000 claims description 6
• YGPRQGYPOCBNKR-UHFFFAOYSA-N 6-(2-bromo-5-chlorophenyl)-5-chloro-n-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(F)(F)F)=C1C1=CC(Cl)=CC=C1Br YGPRQGYPOCBNKR-UHFFFAOYSA-N 0.000 claims description 6
• BBYNFVUYWVJDHH-UHFFFAOYSA-N 6-(2-bromophenyl)-5-chloro-n-(3,3-dimethylbutan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(C)(C)C)=C1C1=CC=CC=C1Br BBYNFVUYWVJDHH-UHFFFAOYSA-N 0.000 claims description 6
• WVSNXFDBGBUXKT-UHFFFAOYSA-N 6-(2-bromophenyl)-n-butan-2-yl-5-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)CC)=C1C1=CC=CC=C1Br WVSNXFDBGBUXKT-UHFFFAOYSA-N 0.000 claims description 6
• FEOCNAIZIDFIQE-UHFFFAOYSA-N 6-(2-chloro-5-fluorophenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine-5-carbonitrile Chemical compound C1CC(C)CCN1C(N1N=CN=C1N=C1C#N)=C1C1=CC(F)=CC=C1Cl FEOCNAIZIDFIQE-UHFFFAOYSA-N 0.000 claims description 6
• CTVAZIWPCRORAT-UHFFFAOYSA-N 6-(2-chloro-5-methylsulfanylphenyl)-7-(4-methylpiperidin-1-yl)-5-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound CSC1=CC=C(Cl)C(C2=C(N3N=CN=C3N=C2SC)N2CCC(C)CC2)=C1 CTVAZIWPCRORAT-UHFFFAOYSA-N 0.000 claims description 6
• ZKTZVXJGFJHXFC-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-5-(difluoromethoxy)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C(=CC=CC=2F)Cl)C(OC(F)F)=NC2=NC=NN12 ZKTZVXJGFJHXFC-UHFFFAOYSA-N 0.000 claims description 6
• NXOUWXOHWKTMPQ-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-5-methoxy-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC=1C=CC=C(Cl)C=1C=1C(OC)=NC2=NC=NN2C=1N1CCC(C)CC1 NXOUWXOHWKTMPQ-UHFFFAOYSA-N 0.000 claims description 6
• PEFNCUPUKBRQQE-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-5-methyl-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C(=CC=CC=2F)Cl)C(C)=NC2=NC=NN12 PEFNCUPUKBRQQE-UHFFFAOYSA-N 0.000 claims description 6
• SWBQQQHZYBAGHN-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperidin-1-yl)-5-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC=1C=CC=C(Cl)C=1C=1C(SC)=NC2=NC=NN2C=1N1CCC(C)CC1 SWBQQQHZYBAGHN-UHFFFAOYSA-N 0.000 claims description 6
• BPLLWWUZFHDTAU-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-amine Chemical compound C1CC(C)CCN1C1=C(C=2C(=CC=CC=2F)Cl)C(N)=NC2=NC=NN12 BPLLWWUZFHDTAU-UHFFFAOYSA-N 0.000 claims description 6
• WBNPKOBROZDPFH-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-7-cyclohexyl-5-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC=1C=CC=C(Cl)C=1C=1C(SC)=NC2=NC=NN2C=1C1CCCCC1 WBNPKOBROZDPFH-UHFFFAOYSA-N 0.000 claims description 6
• PRJCPOIQRFEHOZ-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-7-cyclohexyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-amine Chemical compound FC=1C=CC=C(Cl)C=1C=1C(N)=NC2=NC=NN2C=1C1CCCCC1 PRJCPOIQRFEHOZ-UHFFFAOYSA-N 0.000 claims description 6
• ZAJRQLZLKKVOSN-UHFFFAOYSA-N 6-(2-chloro-6-fluorophenyl)-n-ethyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NC2=NC=NN2C(NCC)=C1C1=C(F)C=CC=C1Cl ZAJRQLZLKKVOSN-UHFFFAOYSA-N 0.000 claims description 6
• FIWZSMCGFYKGRO-UHFFFAOYSA-N 6-(2-methylpropyl)-5,7-diphenoxy-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound N=1C2=NC=NN2C(OC=2C=CC=CC=2)=C(CC(C)C)C=1OC1=CC=CC=C1 FIWZSMCGFYKGRO-UHFFFAOYSA-N 0.000 claims description 6
• SZPREDSSHXAEDS-UHFFFAOYSA-N 6-(4-bromophenyl)-5-chloro-7-(3-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1C(C)CCCN1C1=C(C=2C=CC(Br)=CC=2)C(Cl)=NC2=NC=NN12 SZPREDSSHXAEDS-UHFFFAOYSA-N 0.000 claims description 6
• KQZDAGIBSPTUTC-UHFFFAOYSA-N 6-(4-methoxyphenyl)-5,7-diphenoxy-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(OC=2C=CC=CC=2)N2N=CN=C2N=C1OC1=CC=CC=C1 KQZDAGIBSPTUTC-UHFFFAOYSA-N 0.000 claims description 6
• JFQWWZDFSVCTND-UHFFFAOYSA-N 6-(4-tert-butylphenyl)-5-chloro-7-(2-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound CC1CCCCN1C1=C(C=2C=CC(=CC=2)C(C)(C)C)C(Cl)=NC2=NC=NN12 JFQWWZDFSVCTND-UHFFFAOYSA-N 0.000 claims description 6
• GJXXKBGFMUFNEZ-UHFFFAOYSA-N 6-(4-tert-butylphenyl)-5-chloro-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C=CC(=CC=2)C(C)(C)C)C(Cl)=NC2=NC=NN12 GJXXKBGFMUFNEZ-UHFFFAOYSA-N 0.000 claims description 6
• MXYFXJOYWZLILD-UHFFFAOYSA-N 6-(4-tert-butylphenyl)-5-chloro-n-propan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C)=C1C1=CC=C(C(C)(C)C)C=C1 MXYFXJOYWZLILD-UHFFFAOYSA-N 0.000 claims description 6
• JVMSECYPZKGJLD-UHFFFAOYSA-N 6-[4-[5-chloro-7-(1,1,1-trifluoropropan-2-ylamino)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-3,5-difluorophenoxy]hexanoic acid Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(F)(F)F)=C1C1=C(F)C=C(OCCCCCC(O)=O)C=C1F JVMSECYPZKGJLD-UHFFFAOYSA-N 0.000 claims description 6
• SCCZEAQXSLIFPE-UHFFFAOYSA-N 7-(2-benzyl-4,5-dihydroimidazol-1-yl)-5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(N2C(=NCC2)CC=2C=CC=CC=2)N2N=CN=C2N=C1Cl SCCZEAQXSLIFPE-UHFFFAOYSA-N 0.000 claims description 6
• ZLRVFVKOYNYMSM-UHFFFAOYSA-N 7-(3-bromophenyl)-2-ethyl-6-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC(Br)=CC=1C=1N2N=C(CC)N=C2N=CC=1C1=CC=C(OC)C=C1 ZLRVFVKOYNYMSM-UHFFFAOYSA-N 0.000 claims description 6
• HOTYDFICBUAEMP-UHFFFAOYSA-N 7-(3-bromophenyl)-6-(3-chlorophenyl)-2-ethyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC(Br)=CC=1C=1N2N=C(CC)N=C2N=CC=1C1=CC=CC(Cl)=C1 HOTYDFICBUAEMP-UHFFFAOYSA-N 0.000 claims description 6
• JPFAGMMSBCMJIM-UHFFFAOYSA-N 7-(4-bromophenyl)-2-ethyl-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=C(Br)C=CC=1C=1N2N=C(CC)N=C2N=CC=1C1=CC=C(C(F)(F)F)C=C1 JPFAGMMSBCMJIM-UHFFFAOYSA-N 0.000 claims description 6
• VECBLZJQFCVHRZ-UHFFFAOYSA-N 7-(4-bromopiperidin-1-yl)-5-chloro-6-(2,6-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(F)=C1C1=C(N2CCC(Br)CC2)N2N=CN=C2N=C1Cl VECBLZJQFCVHRZ-UHFFFAOYSA-N 0.000 claims description 6
• VLNWPRQJGYBBDF-UHFFFAOYSA-N 7-(4-bromopiperidin-1-yl)-5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(Cl)=C1C1=C(N2CCC(Br)CC2)N2N=CN=C2N=C1Cl VLNWPRQJGYBBDF-UHFFFAOYSA-N 0.000 claims description 6
• UKACSXVYQUNJRD-UHFFFAOYSA-N 7-(4-bromopiperidin-1-yl)-5-chloro-6-(2-chlorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound ClC1=CC=CC=C1C1=C(N2CCC(Br)CC2)N2N=CN=C2N=C1Cl UKACSXVYQUNJRD-UHFFFAOYSA-N 0.000 claims description 6
• VRUPVDAGIOOZTJ-UHFFFAOYSA-N 7-(4-chlorophenyl)-2-methyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=C(Cl)C=CC=1C=1N2N=C(C)N=C2N=CC=1C1=CC=CC=C1 VRUPVDAGIOOZTJ-UHFFFAOYSA-N 0.000 claims description 6
• MUFAHCOBIWYOAM-UHFFFAOYSA-N 7-(4-methoxyphenyl)-6-phenyl-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC=CC=2)C=NC2=NC(C(F)(F)F)=NN12 MUFAHCOBIWYOAM-UHFFFAOYSA-N 0.000 claims description 6
• TZSVZTGMBRHBGF-UHFFFAOYSA-N 7-butyl-5-chloro-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound ClC1=NC2=NC=NN2C(CCCC)=C1C1=C(F)C=C(F)C=C1F TZSVZTGMBRHBGF-UHFFFAOYSA-N 0.000 claims description 6
• VDTGOOYHLQGSFF-UHFFFAOYSA-N 7-butyl-5-chloro-6-(2,6-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound ClC1=NC2=NC=NN2C(CCCC)=C1C1=C(F)C=CC=C1F VDTGOOYHLQGSFF-UHFFFAOYSA-N 0.000 claims description 6
• BBAPUZHTVBDBEO-UHFFFAOYSA-N 7-cyclohexyl-6-(2,6-difluoro-4-methoxyphenyl)-5-methoxy-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(C2CCCCC2)N2N=CN=C2N=C1OC BBAPUZHTVBDBEO-UHFFFAOYSA-N 0.000 claims description 6
• CNYCCXWLXMZRAI-UHFFFAOYSA-N 7-cyclohexyl-6-[2,6-difluoro-4-(2-methoxyethoxy)phenyl]-5-(2-methoxyethoxy)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(OCCOC)=CC(F)=C1C1=C(C2CCCCC2)N2N=CN=C2N=C1OCCOC CNYCCXWLXMZRAI-UHFFFAOYSA-N 0.000 claims description 6
• UEKZZQNXKHBXRH-UHFFFAOYSA-N 7-cyclopentyl-6-(2,6-difluoro-4-methoxyphenyl)-5-methoxy-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(C2CCCC2)N2N=CN=C2N=C1OC UEKZZQNXKHBXRH-UHFFFAOYSA-N 0.000 claims description 6
• RCLMJLBVOZHVKM-UHFFFAOYSA-N 7-n-cyclopentyl-5-n,5-n-dimethyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine-5,7-diamine Chemical compound C=1C=CC=CC=1C=1C(N(C)C)=NC2=NC=NN2C=1NC1CCCC1 RCLMJLBVOZHVKM-UHFFFAOYSA-N 0.000 claims description 6
• BHKNBOSSNZKSLE-UHFFFAOYSA-N 8-[5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-1,4-dioxa-8-azaspiro[4.5]decane Chemical compound FC1=CC=CC(Cl)=C1C1=C(N2CCC3(CC2)OCCO3)N2N=CN=C2N=C1Cl BHKNBOSSNZKSLE-UHFFFAOYSA-N 0.000 claims description 6
• YMRGFPBLYYJGRN-UHFFFAOYSA-N 8-[5-chloro-6-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-1,4-dioxa-8-azaspiro[4.5]decane Chemical compound C1=CC(OC)=CC=C1C1=C(N2CCC3(CC2)OCCO3)N2N=CN=C2N=C1Cl YMRGFPBLYYJGRN-UHFFFAOYSA-N 0.000 claims description 6
• 102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 claims description 6
• DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
• FMDKFPUJFDTWEC-UHFFFAOYSA-N ClC1=C(C(=CC=2N1N=CN2)N(CC(=C)C)CC)C2=C(C=C(C=C2)[N+](=O)[O-])Cl Chemical compound ClC1=C(C(=CC=2N1N=CN2)N(CC(=C)C)CC)C2=C(C=C(C=C2)[N+](=O)[O-])Cl FMDKFPUJFDTWEC-UHFFFAOYSA-N 0.000 claims description 6
• JDMGRSURBDZAAM-UHFFFAOYSA-N FC1=CC=CC(Cl)=C1C1=C(C2CCCCC2)N2N=CN=C2N=C1N=[N+]=[N-] Chemical compound FC1=CC=CC(Cl)=C1C1=C(C2CCCCC2)N2N=CN=C2N=C1N=[N+]=[N-] JDMGRSURBDZAAM-UHFFFAOYSA-N 0.000 claims description 6
• QOXCEADXSTZKHA-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=CC=NC2=NC=NN12 QOXCEADXSTZKHA-UHFFFAOYSA-N 0.000 claims description 6
• IWRNEYVKAJXLDB-UHFFFAOYSA-N [5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]methanol Chemical compound ClC1=NC2=NC=NN2C(CO)=C1C1=C(F)C=CC=C1Cl IWRNEYVKAJXLDB-UHFFFAOYSA-N 0.000 claims description 6
• WRTWKBSJHGPRMV-UHFFFAOYSA-N [5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]methyl acetate Chemical compound ClC1=NC2=NC=NN2C(COC(=O)C)=C1C1=C(F)C=CC=C1Cl WRTWKBSJHGPRMV-UHFFFAOYSA-N 0.000 claims description 6
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 230000005764 inhibitory process Effects 0.000 claims description 6
• 208000032839 leukemia Diseases 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• GQYMWUNXYFJTDH-UHFFFAOYSA-N methyl 2-[5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]acetate Chemical compound ClC1=NC2=NC=NN2C(CC(=O)OC)=C1C1=C(F)C=CC=C1Cl GQYMWUNXYFJTDH-UHFFFAOYSA-N 0.000 claims description 6
• HCTFNTJQWJKNQY-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-5-chloro-6-(2,4-dichlorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical class ClC1=CC(Cl)=CC=C1C1=C(NC2C3CCC(C3)C2)N2N=CN=C2N=C1Cl HCTFNTJQWJKNQY-UHFFFAOYSA-N 0.000 claims description 6
• MWRXKQXMFVQTCK-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-5-chloro-6-(2-fluoro-4-nitrophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC([N+](=O)[O-])=CC=C1C1=C(NC2C3CCC(C3)C2)N2N=CN=C2N=C1Cl MWRXKQXMFVQTCK-UHFFFAOYSA-N 0.000 claims description 6
• HOIWUMJGTHUVPJ-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-5-chloro-6-(3-chloro-4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(NC2C3CCC(C3)C2)N2N=CN=C2N=C1Cl HOIWUMJGTHUVPJ-UHFFFAOYSA-N 0.000 claims description 6
• GKRJJFYEDBHZQB-UHFFFAOYSA-N n-[4-[5-chloro-7-(4-methylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]phenyl]acetamide Chemical compound C1CC(C)CCN1C1=C(C=2C=CC(NC(C)=O)=CC=2)C(Cl)=NC2=NC=NN12 GKRJJFYEDBHZQB-UHFFFAOYSA-N 0.000 claims description 6
• WKSCBLOHIKHJHE-UHFFFAOYSA-N n-butan-2-yl-5-chloro-6-(2,6-dichloro-4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)CC)=C1C1=C(Cl)C=C(F)C=C1Cl WKSCBLOHIKHJHE-UHFFFAOYSA-N 0.000 claims description 6
• DXVVHMDPWWSHKC-UHFFFAOYSA-N n-butan-2-yl-5-chloro-6-(4-methylsulfanylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)CC)=C1C1=CC=C(SC)C=C1 DXVVHMDPWWSHKC-UHFFFAOYSA-N 0.000 claims description 6
• QBFNFRZUMQVBSE-UHFFFAOYSA-N n-cyclopentyl-6-(2-fluorophenyl)-5-hydrazinyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C=CC=C(F)C=1C=1C(NN)=NC2=NC=NN2C=1NC1CCCC1 QBFNFRZUMQVBSE-UHFFFAOYSA-N 0.000 claims description 6
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 6
• DURFTFYHOIVAHZ-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2,5-dimethyl-2,5-dihydropyrrol-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound CC1C=CC(C)N1C1=C(C=2C(=CC=CC=2F)Cl)C(Cl)=NC2=NC=NN12 DURFTFYHOIVAHZ-UHFFFAOYSA-N 0.000 claims description 5
• LCYYVLZWWYESDS-UHFFFAOYSA-N 7-(azocan-1-yl)-5-chloro-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=C(F)C(C2=C(N3N=CN=C3N=C2Cl)N2CCCCCCC2)=C1F LCYYVLZWWYESDS-UHFFFAOYSA-N 0.000 claims description 5
• OIGOSVFEYUWTPU-UHFFFAOYSA-N 7-(azocan-1-yl)-5-chloro-6-(2,6-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC=CC(F)=C1C1=C(N2CCCCCCC2)N2N=CN=C2N=C1Cl OIGOSVFEYUWTPU-UHFFFAOYSA-N 0.000 claims description 5
• JHNCIUGGSYYBBG-UHFFFAOYSA-N diethyl 2-[[5-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]oxy]-2-(2-methylpropyl)propanedioate Chemical compound ClC1=NC2=NC=NN2C(OC(CC(C)C)(C(=O)OCC)C(=O)OCC)=C1C1=C(F)C=CC=C1Cl JHNCIUGGSYYBBG-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• SEGKBWQINICKME-UHFFFAOYSA-N 5-chloro-6-(4-methoxyphenyl)-7-phenoxy-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(OC=2C=CC=CC=2)N2N=CN=C2N=C1Cl SEGKBWQINICKME-UHFFFAOYSA-N 0.000 claims description 4
• SFKUEIBKBDUHDR-UHFFFAOYSA-N 5-chloro-7-(cyclohexen-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(F)=CC(F)=C1C1=C(C=2CCCCC=2)N2N=CN=C2N=C1Cl SFKUEIBKBDUHDR-UHFFFAOYSA-N 0.000 claims description 4
• FFJYIWDWMFYMCI-UHFFFAOYSA-N 5-chloro-7-cyclohex-3-en-1-yl-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(F)=CC(F)=C1C1=C(C2CC=CCC2)N2N=CN=C2N=C1Cl FFJYIWDWMFYMCI-UHFFFAOYSA-N 0.000 claims description 4
• NQRLQRRGIXDMCU-UHFFFAOYSA-N 5-chloro-n-(1-phenylethyl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C=CC=CC=1C(C)NC(N1N=CN=C1N=C1Cl)=C1C1=C(F)C=C(F)C=C1F NQRLQRRGIXDMCU-UHFFFAOYSA-N 0.000 claims description 4
• STGCMCOXHGFBGY-UHFFFAOYSA-N 5-chloro-n-(4,4,4-trifluoro-2-methylbutyl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NCC(C)CC(F)(F)F)=C1C1=C(F)C=C(F)C=C1F STGCMCOXHGFBGY-UHFFFAOYSA-N 0.000 claims description 4
• KRRRPQGYIMTIDP-UHFFFAOYSA-N 5-chloro-n-[4-(trifluoromethyl)phenyl]-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(F)=CC(F)=C1C1=C(NC=2C=CC(=CC=2)C(F)(F)F)N2N=CN=C2N=C1Cl KRRRPQGYIMTIDP-UHFFFAOYSA-N 0.000 claims description 4
• 210000004556 brain Anatomy 0.000 claims description 4
• 210000000481 breast Anatomy 0.000 claims description 4
• 210000001072 colon Anatomy 0.000 claims description 4
• 210000002615 epidermis Anatomy 0.000 claims description 4
• 210000003238 esophagus Anatomy 0.000 claims description 4
• 210000003734 kidney Anatomy 0.000 claims description 4
• 210000000867 larynx Anatomy 0.000 claims description 4
• 210000004185 liver Anatomy 0.000 claims description 4
• 210000004072 lung Anatomy 0.000 claims description 4
• 210000000214 mouth Anatomy 0.000 claims description 4
• 230000017066 negative regulation of growth Effects 0.000 claims description 4
• 210000001672 ovary Anatomy 0.000 claims description 4
• 210000000496 pancreas Anatomy 0.000 claims description 4
• 210000002307 prostate Anatomy 0.000 claims description 4
• 210000003491 skin Anatomy 0.000 claims description 4
• 210000002784 stomach Anatomy 0.000 claims description 4
• 210000003932 urinary bladder Anatomy 0.000 claims description 4
• 125000004643 (C1-C12) haloalkoxy group Chemical group 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 230000010534 mechanism of action Effects 0.000 claims description 2
• 230000004565 tumor cell growth Effects 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
• 229910052698 phosphorus Inorganic materials 0.000 claims 4
• 239000011574 phosphorus Substances 0.000 claims 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 2
• WDAOJHRPYXLTDC-UHFFFAOYSA-N 2-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound N=1N2C(N)=CC=NC2=NC=1C1=C(F)C=C(F)C=C1F WDAOJHRPYXLTDC-UHFFFAOYSA-N 0.000 claims 2
• SMWVPOZXNMYRHX-UHFFFAOYSA-N 2-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(F)=CC(F)=C1C1=NN2C=CC=NC2=N1 SMWVPOZXNMYRHX-UHFFFAOYSA-N 0.000 claims 2
• MRSGUNOHVSPVDL-UHFFFAOYSA-N 2-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=NN2C=CC=NC2=N1 MRSGUNOHVSPVDL-UHFFFAOYSA-N 0.000 claims 2
• DACWQSNZECJJGG-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CN=C21 DACWQSNZECJJGG-UHFFFAOYSA-N 0.000 claims 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
• POFDSYGXHVPQNX-UHFFFAOYSA-N triazolo[1,5-a]pyrimidine Chemical compound C1=CC=NC2=CN=NN21 POFDSYGXHVPQNX-UHFFFAOYSA-N 0.000 claims 2
• 230000012010 growth Effects 0.000 abstract description 18
• 210000004027 cell Anatomy 0.000 description 94
• 241001465754 Metazoa Species 0.000 description 63
• 238000010998 test method Methods 0.000 description 45
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 36
• 230000000144 pharmacologic effect Effects 0.000 description 31
• 238000011156 evaluation Methods 0.000 description 29
• 125000001424 substituent group Chemical group 0.000 description 25
• IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 22
• 238000002474 experimental method Methods 0.000 description 20
• 238000006116 polymerization reaction Methods 0.000 description 19
• 238000012360 testing method Methods 0.000 description 18
• 229940079593 drug Drugs 0.000 description 17
• 230000000694 effects Effects 0.000 description 15
• 238000003359 percent control normalization Methods 0.000 description 15
• 230000008569 process Effects 0.000 description 15
• 241000699660 Mus musculus Species 0.000 description 13
• 238000011580 nude mouse model Methods 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• XKMLYUALXHKNFT-UUOKFMHZSA-N Guanosine-5'-triphosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XKMLYUALXHKNFT-UUOKFMHZSA-N 0.000 description 12
• XKMLYUALXHKNFT-UHFFFAOYSA-N rGTP Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O XKMLYUALXHKNFT-UHFFFAOYSA-N 0.000 description 12
• 229960001338 colchicine Drugs 0.000 description 11
• 230000003013 cytotoxicity Effects 0.000 description 11
• 231100000135 cytotoxicity Toxicity 0.000 description 11
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 11
• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 11
• 229960004528 vincristine Drugs 0.000 description 11
• 238000000692 Student's t-test Methods 0.000 description 10
• 239000000203 mixture Substances 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 9
• 230000022131 cell cycle Effects 0.000 description 9
• 208000002154 non-small cell lung carcinoma Diseases 0.000 description 9
• 230000006907 apoptotic process Effects 0.000 description 8
• 238000011534 incubation Methods 0.000 description 8
• 239000002609 medium Substances 0.000 description 8
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 8
• 238000002835 absorbance Methods 0.000 description 7
• 231100000433 cytotoxic Toxicity 0.000 description 7
• 230000001472 cytotoxic effect Effects 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 150000003254 radicals Chemical class 0.000 description 7
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• 238000003556 assay Methods 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
• 125000001589 carboacyl group Chemical group 0.000 description 5
• 230000010261 cell growth Effects 0.000 description 5
• 238000006243 chemical reaction Methods 0.000 description 5
• 238000001514 detection method Methods 0.000 description 5
• 101150042537 dld1 gene Proteins 0.000 description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
• 125000002541 furyl group Chemical group 0.000 description 5
• 208000005017 glioblastoma Diseases 0.000 description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
• 230000004044 response Effects 0.000 description 5
• 230000001988 toxicity Effects 0.000 description 5
• 231100000419 toxicity Toxicity 0.000 description 5
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 4
• 108020004414 DNA Proteins 0.000 description 4
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 4
• 229930182816 L-glutamine Natural products 0.000 description 4
• 229930182555 Penicillin Natural products 0.000 description 4
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
• 239000012980 RPMI-1640 medium Substances 0.000 description 4
• 238000004364 calculation method Methods 0.000 description 4
• 239000002775 capsule Substances 0.000 description 4
• 230000004663 cell proliferation Effects 0.000 description 4
• 208000029742 colonic neoplasm Diseases 0.000 description 4
• 229940127089 cytotoxic agent Drugs 0.000 description 4
• 239000002254 cytotoxic agent Substances 0.000 description 4
• 231100000599 cytotoxic agent Toxicity 0.000 description 4
• 231100000263 cytotoxicity test Toxicity 0.000 description 4
• 125000001183 hydrocarbyl group Chemical group 0.000 description 4
• 238000007912 intraperitoneal administration Methods 0.000 description 4
• 230000000394 mitotic effect Effects 0.000 description 4
• 229940049954 penicillin Drugs 0.000 description 4
• 230000035755 proliferation Effects 0.000 description 4
• 229960005322 streptomycin Drugs 0.000 description 4
• 239000000758 substrate Substances 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• 230000004614 tumor growth Effects 0.000 description 4
• IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 description 3
• TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• 231100000070 MTS assay Toxicity 0.000 description 3
• 238000000719 MTS assay Methods 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• KYRVNWMVYQXFEU-UHFFFAOYSA-N Nocodazole Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CS1 KYRVNWMVYQXFEU-UHFFFAOYSA-N 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 3
• 229940041181 antineoplastic drug Drugs 0.000 description 3
• 125000003710 aryl alkyl group Chemical group 0.000 description 3
• 239000003153 chemical reaction reagent Substances 0.000 description 3
• 239000003795 chemical substances by application Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 201000010897 colon adenocarcinoma Diseases 0.000 description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
• 230000034994 death Effects 0.000 description 3
• 229960004679 doxorubicin Drugs 0.000 description 3
• 239000012091 fetal bovine serum Substances 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• 239000012737 fresh medium Substances 0.000 description 3
• 230000006870 function Effects 0.000 description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
• 230000003993 interaction Effects 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 3
• 229960001156 mitoxantrone Drugs 0.000 description 3
• 229950006344 nocodazole Drugs 0.000 description 3
• 230000003389 potentiating effect Effects 0.000 description 3
• 239000002243 precursor Substances 0.000 description 3
• 102000004169 proteins and genes Human genes 0.000 description 3
• 108090000623 proteins and genes Proteins 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• 238000011084 recovery Methods 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• 229960003048 vinblastine Drugs 0.000 description 3
• JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• APRZHQXAAWPYHS-UHFFFAOYSA-N 4-[5-[3-(carboxymethoxy)phenyl]-3-(4,5-dimethyl-1,3-thiazol-2-yl)tetrazol-3-ium-2-yl]benzenesulfonate Chemical compound S1C(C)=C(C)N=C1[N+]1=NC(C=2C=C(OCC(O)=O)C=CC=2)=NN1C1=CC=C(S([O-])(=O)=O)C=C1 APRZHQXAAWPYHS-UHFFFAOYSA-N 0.000 description 2
• WLROAFONPPCFIS-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-n-[(2,2-dichlorocyclopropyl)methyl]-n-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC=1C=CC=C(Cl)C=1C=1C(Cl)=NC2=NC=NN2C=1N(C)CC1CC1(Cl)Cl WLROAFONPPCFIS-UHFFFAOYSA-N 0.000 description 2
• YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 2
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 2
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 2
• 241000167854 Bourreria succulenta Species 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 2
• 201000009030 Carcinoma Diseases 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• 206010009944 Colon cancer Diseases 0.000 description 2
• 229920002261 Corn starch Polymers 0.000 description 2
• 230000006820 DNA synthesis Effects 0.000 description 2
• 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 2
• 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 2
• 108010092160 Dactinomycin Proteins 0.000 description 2
• 206010059866 Drug resistance Diseases 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• 241000699670 Mus sp. Species 0.000 description 2
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 2
• 206010060862 Prostate cancer Diseases 0.000 description 2
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 2
• 230000002159 abnormal effect Effects 0.000 description 2
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• 239000004480 active ingredient Substances 0.000 description 2
• 238000004458 analytical method Methods 0.000 description 2
• 230000000259 anti-tumor effect Effects 0.000 description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• 208000036815 beta tubulin Diseases 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• 229910052791 calcium Inorganic materials 0.000 description 2
• 239000011575 calcium Substances 0.000 description 2
• 229940127093 camptothecin Drugs 0.000 description 2
• VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 2
• 238000003783 cell cycle assay Methods 0.000 description 2
• 238000002512 chemotherapy Methods 0.000 description 2
• 235000019693 cherries Nutrition 0.000 description 2
• 239000000460 chlorine Substances 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• 239000008120 corn starch Substances 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• 230000006378 damage Effects 0.000 description 2
• 238000010790 dilution Methods 0.000 description 2
• 239000012895 dilution Substances 0.000 description 2
• 239000006185 dispersion Substances 0.000 description 2
• VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 2
• 239000000975 dye Substances 0.000 description 2
• 238000000684 flow cytometry Methods 0.000 description 2
• 125000001153 fluoro group Chemical group F* 0.000 description 2
• 235000003599 food sweetener Nutrition 0.000 description 2
• 230000036039 immunity Effects 0.000 description 2
• 238000010166 immunofluorescence Methods 0.000 description 2
• 239000003112 inhibitor Substances 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• 244000005700 microbiome Species 0.000 description 2
• 125000002757 morpholinyl group Chemical group 0.000 description 2
• 230000036457 multidrug resistance Effects 0.000 description 2
• 239000003921 oil Substances 0.000 description 2
• 230000003287 optical effect Effects 0.000 description 2
• 229910052760 oxygen Inorganic materials 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• 239000000546 pharmaceutical excipient Substances 0.000 description 2
• 239000006187 pill Substances 0.000 description 2
• 229920001223 polyethylene glycol Polymers 0.000 description 2
• 239000003755 preservative agent Substances 0.000 description 2
• XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• 230000002829 reductive effect Effects 0.000 description 2
• 238000010186 staining Methods 0.000 description 2
• 238000003860 storage Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 125000005017 substituted alkenyl group Chemical group 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 229910052717 sulfur Inorganic materials 0.000 description 2
• 239000011593 sulfur Substances 0.000 description 2
• 239000000725 suspension Substances 0.000 description 2
• 239000003765 sweetening agent Substances 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
• 235000020357 syrup Nutrition 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 2
• 210000001519 tissue Anatomy 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
• DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
• UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
• ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
• APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
• FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
• IHPYMWDTONKSCO-UHFFFAOYSA-N 2,2'-piperazine-1,4-diylbisethanesulfonic acid Chemical compound OS(=O)(=O)CCN1CCN(CCS(O)(=O)=O)CC1 IHPYMWDTONKSCO-UHFFFAOYSA-N 0.000 description 1
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
• ZIWFHZFWEYRZSV-UHFFFAOYSA-N 3-(2-methylpropoxy)-3-oxopropanoic acid Chemical compound CC(C)COC(=O)CC(O)=O ZIWFHZFWEYRZSV-UHFFFAOYSA-N 0.000 description 1
• BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
• YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
• SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
• YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
• XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
• IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
• RJKOCYSSZKHKCT-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-n-(3,3-dimethylbutan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(C)(C)C)=C1C1=C(F)C=CC=C1Cl RJKOCYSSZKHKCT-UHFFFAOYSA-N 0.000 description 1
• WBMFCGRQWPJXMZ-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-6-(4-ethoxy-2,3,5,6-tetrafluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=C(F)C(OCC)=C(F)C(F)=C1C1=C(NC2CCCC2)N2N=CN=C2N=C1Cl WBMFCGRQWPJXMZ-UHFFFAOYSA-N 0.000 description 1
• PELQSSHKTIVXBP-UHFFFAOYSA-N 5-chloro-n-ethyl-6-(2-methoxyphenyl)-n-(2-methylprop-2-enyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)=C)CC)=C1C1=CC=CC=C1OC PELQSSHKTIVXBP-UHFFFAOYSA-N 0.000 description 1
• SIVPKGINWDFUID-UHFFFAOYSA-N 5-chloro-n-ethyl-6-(4-methoxyphenyl)-n-(2-methylprop-2-enyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)=C)CC)=C1C1=CC=C(OC)C=C1 SIVPKGINWDFUID-UHFFFAOYSA-N 0.000 description 1
• AFBUXICFZBZNIK-UHFFFAOYSA-N 5-chloro-n-ethyl-n-(2-methylprop-2-enyl)-6-(4-phenoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)=C)CC)=C1C(C=C1)=CC=C1OC1=CC=CC=C1 AFBUXICFZBZNIK-UHFFFAOYSA-N 0.000 description 1
• KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 238000012935 Averaging Methods 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 241000283707 Capra Species 0.000 description 1
• KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
• 238000002965 ELISA Methods 0.000 description 1
• 241000257465 Echinoidea Species 0.000 description 1
• 208000005189 Embolism Diseases 0.000 description 1
• GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 241000233866 Fungi Species 0.000 description 1
• 240000001238 Gaultheria procumbens Species 0.000 description 1
• 235000007297 Gaultheria procumbens Nutrition 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• 239000007995 HEPES buffer Substances 0.000 description 1
• 101000573199 Homo sapiens Protein PML Proteins 0.000 description 1
• 101001054867 Homo sapiens Protein-lysine 6-oxidase Proteins 0.000 description 1
• 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 206010025323 Lymphomas Diseases 0.000 description 1
• 244000246386 Mentha pulegium Species 0.000 description 1
• 235000016257 Mentha pulegium Nutrition 0.000 description 1
• 235000004357 Mentha x piperita Nutrition 0.000 description 1
• 241001024304 Mino Species 0.000 description 1
• 241001529936 Murinae Species 0.000 description 1
• 241000238367 Mya arenaria Species 0.000 description 1
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
• FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
• 206010039491 Sarcoma Diseases 0.000 description 1
• 229920001800 Shellac Polymers 0.000 description 1
• 108010091105 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 description 1
• 102000018075 Subfamily B ATP Binding Cassette Transporter Human genes 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 229940123237 Taxane Drugs 0.000 description 1
• 241001116500 Taxus Species 0.000 description 1
• 241001116498 Taxus baccata Species 0.000 description 1
• 241000202349 Taxus brevifolia Species 0.000 description 1
• 241000015728 Taxus canadensis Species 0.000 description 1
• 235000009065 Taxus cuspidata Nutrition 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 208000002495 Uterine Neoplasms Diseases 0.000 description 1
• 229940122803 Vinca alkaloid Drugs 0.000 description 1
• 238000009825 accumulation Methods 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 229930183665 actinomycin Natural products 0.000 description 1
• RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 230000002776 aggregation Effects 0.000 description 1
• 238000004220 aggregation Methods 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 125000003302 alkenyloxy group Chemical group 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 230000001093 anti-cancer Effects 0.000 description 1
• 230000000118 anti-neoplastic effect Effects 0.000 description 1
• 229940034982 antineoplastic agent Drugs 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 125000003725 azepanyl group Chemical group 0.000 description 1
• 150000007514 bases Chemical class 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 230000003915 cell function Effects 0.000 description 1
• 238000001516 cell proliferation assay Methods 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 210000003850 cellular structure Anatomy 0.000 description 1
• 230000002490 cerebral effect Effects 0.000 description 1
• DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
• 239000007958 cherry flavor Substances 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 239000008162 cooking oil Substances 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 239000000287 crude extract Substances 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 210000004292 cytoskeleton Anatomy 0.000 description 1
• 238000002784 cytotoxicity assay Methods 0.000 description 1
• 229960000640 dactinomycin Drugs 0.000 description 1
• 230000000368 destabilizing effect Effects 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
• 230000008034 disappearance Effects 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 239000002612 dispersion medium Substances 0.000 description 1
• 229930004069 diterpene Natural products 0.000 description 1
• 150000004141 diterpene derivatives Chemical class 0.000 description 1
• 229960003668 docetaxel Drugs 0.000 description 1
• 239000003684 drug solvent Substances 0.000 description 1
• 230000002900 effect on cell Effects 0.000 description 1
• 229950007919 egtazic acid Drugs 0.000 description 1
• 230000005611 electricity Effects 0.000 description 1
• DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
• 239000012894 fetal calf serum Substances 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 239000012530 fluid Substances 0.000 description 1
• MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 235000013305 food Nutrition 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 239000012634 fragment Substances 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 239000000417 fungicide Substances 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 238000000227 grinding Methods 0.000 description 1
• 239000000833 heterodimer Substances 0.000 description 1
• 235000001050 hortel pimenta Nutrition 0.000 description 1
• 102000051318 human LOX Human genes 0.000 description 1
• 102000054896 human PML Human genes 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
• 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
• 238000003125 immunofluorescent labeling Methods 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 230000006882 induction of apoptosis Effects 0.000 description 1
• 239000003701 inert diluent Substances 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 239000007928 intraperitoneal injection Substances 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910001629 magnesium chloride Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 125000005394 methallyl group Chemical group 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
• OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 230000011278 mitosis Effects 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 230000000877 morphologic effect Effects 0.000 description 1
• VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
• FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
• XVWBGHBNPKSAKI-UHFFFAOYSA-N n-butyl-5-chloro-n-ethyl-6-(2,3,4,5,6-pentafluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC)CCCC)=C1C1=C(F)C(F)=C(F)C(F)=C1F XVWBGHBNPKSAKI-UHFFFAOYSA-N 0.000 description 1
• NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 230000017095 negative regulation of cell growth Effects 0.000 description 1
• 230000035407 negative regulation of cell proliferation Effects 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 239000007935 oral tablet Substances 0.000 description 1
• 239000007968 orange flavor Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 239000002953 phosphate buffered saline Substances 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 125000005936 piperidyl group Chemical group 0.000 description 1
• 238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 229920005862 polyol Polymers 0.000 description 1
• 150000003077 polyols Chemical class 0.000 description 1
• LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
• 239000013641 positive control Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 229920001592 potato starch Polymers 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 229940002612 prodrug Drugs 0.000 description 1
• 239000000651 prodrug Substances 0.000 description 1
• 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
• 201000001514 prostate carcinoma Diseases 0.000 description 1
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 230000008929 regeneration Effects 0.000 description 1
• 238000011069 regeneration method Methods 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
• 235000019204 saccharin Nutrition 0.000 description 1
• 229940081974 saccharin Drugs 0.000 description 1
• 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
• XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 239000004208 shellac Substances 0.000 description 1
• ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
• 229940113147 shellac Drugs 0.000 description 1
• 235000013874 shellac Nutrition 0.000 description 1
• 238000004904 shortening Methods 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 238000002798 spectrophotometry method Methods 0.000 description 1
• 125000003003 spiro group Chemical group 0.000 description 1
• 238000007655 standard test method Methods 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 238000003210 sulforhodamine B staining Methods 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 229940063683 taxotere Drugs 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 229940126585 therapeutic drug Drugs 0.000 description 1
• 230000004797 therapeutic response Effects 0.000 description 1
• 125000006407 thiazinanyl group Chemical group 0.000 description 1
• 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
• 238000002723 toxicity assay Methods 0.000 description 1
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
• 206010046766 uterine cancer Diseases 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 235000012431 wafers Nutrition 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1