JP2004502691A - 抗癌薬としての置換トリアゾロピリミジン - Google Patents

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Publication number

JP2004502691A

JP2004502691A JP2002507815A JP2002507815A JP2004502691A JP 2004502691 A JP2004502691 A JP 2004502691A JP 2002507815 A JP2002507815 A JP 2002507815A JP 2002507815 A JP2002507815 A JP 2002507815A JP 2004502691 A JP2004502691 A JP 2004502691A

Authority

JP

Japan

Prior art keywords

chloro

triazolo

pyrimidine

carbon atoms

amine

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.)

Pending

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• 239000002246 antineoplastic agent Substances 0.000 title description 8
• 229940041181 antineoplastic drug Drugs 0.000 title description 7
• 150000003839 salts Chemical class 0.000 claims abstract description 116
• 238000000034 method Methods 0.000 claims abstract description 112
• 102000029749 Microtubule Human genes 0.000 claims abstract description 33
• 108091022875 Microtubule Proteins 0.000 claims abstract description 33
• 210000004688 microtubule Anatomy 0.000 claims abstract description 33
• 241000124008 Mammalia Species 0.000 claims abstract description 29
• 102000004243 Tubulin Human genes 0.000 claims abstract description 27
• 108090000704 Tubulin Proteins 0.000 claims abstract description 27
• 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
• 210000004881 tumor cell Anatomy 0.000 claims abstract description 17
• 230000012010 growth Effects 0.000 claims abstract description 16
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 14
• 201000010099 disease Diseases 0.000 claims abstract description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
• 230000029115 microtubule polymerization Effects 0.000 claims abstract description 10
• 230000001737 promoting effect Effects 0.000 claims abstract description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 759
• -1 amino, hydroxy Chemical group 0.000 claims description 435
• 125000000217 alkyl group Chemical group 0.000 claims description 282
• 229910052739 hydrogen Inorganic materials 0.000 claims description 222
• 125000000623 heterocyclic group Chemical group 0.000 claims description 182
• 125000003118 aryl group Chemical group 0.000 claims description 163
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 131
• 239000001257 hydrogen Substances 0.000 claims description 120
• 150000001875 compounds Chemical class 0.000 claims description 114
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 111
• 229910052799 carbon Inorganic materials 0.000 claims description 111
• 229910052736 halogen Inorganic materials 0.000 claims description 110
• 150000002367 halogens Chemical class 0.000 claims description 110
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 98
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 88
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 82
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 80
• 125000004414 alkyl thio group Chemical group 0.000 claims description 79
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 74
• 229910052757 nitrogen Inorganic materials 0.000 claims description 71
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 69
• 125000003545 alkoxy group Chemical group 0.000 claims description 56
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 56
• 125000001188 haloalkyl group Chemical group 0.000 claims description 56
• 150000001412 amines Chemical class 0.000 claims description 55
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 54
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 52
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 48
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 45
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 44
• 125000003282 alkyl amino group Chemical group 0.000 claims description 36
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
• 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 35
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 35
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 33
• 125000006413 ring segment Chemical group 0.000 claims description 33
• 229920006395 saturated elastomer Polymers 0.000 claims description 31
• 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
• 125000003342 alkenyl group Chemical group 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
• 125000003107 substituted aryl group Chemical group 0.000 claims description 30
• POFDSYGXHVPQNX-UHFFFAOYSA-N triazolo[1,5-a]pyrimidine Chemical compound C1=CC=NC2=CN=NN21 POFDSYGXHVPQNX-UHFFFAOYSA-N 0.000 claims description 29
• 125000001424 substituent group Chemical group 0.000 claims description 28
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
• 125000005415 substituted alkoxy group Chemical group 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 24
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 20
• 230000036457 multidrug resistance Effects 0.000 claims description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 16
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 16
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 15
• SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 claims description 15
• YMNDUNZGBFEWKN-UHFFFAOYSA-N 5-chloro-n-ethyl-n-(2-methylprop-2-enyl)-6-(4-methylsulfanylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N(CC(C)=C)CC)=C1C1=CC=C(SC)C=C1 YMNDUNZGBFEWKN-UHFFFAOYSA-N 0.000 claims description 14
• 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
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
• 150000001721 carbon Chemical class 0.000 claims description 12
• 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
• 125000001544 thienyl group Chemical group 0.000 claims description 11
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 10
• 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 10
• 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
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 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
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 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 9
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
• 108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 compound ClC1=NC2=NC=NN2C(NCC=C(C)C)=C1C1=CC(F)=CC=C1F PVALWCUNZYACID-UHFFFAOYSA-N 0.000 claims description 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
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• 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 7
• 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 7
• PLVROXYFWJCWNF-UHFFFAOYSA-N 5-chloro-6-(2-chloro-4-nitrophenyl)-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=CC=C([N+]([O-])=O)C=C1Cl PLVROXYFWJCWNF-UHFFFAOYSA-N 0.000 claims description 7
• 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 7
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• 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 7
• 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 7
• 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 claims description 7
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• 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 7
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• 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 7
• 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 7
• 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 7
• 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 7
• 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 compound 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 7
• ODBFBRKWIXGTCZ-UHFFFAOYSA-N 5-chloro-6-(3-chloro-4-methoxyphenyl)-7-(3,3-dimethylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(N2CC(C)(C)CCC2)N2N=CN=C2N=C1Cl ODBFBRKWIXGTCZ-UHFFFAOYSA-N 0.000 claims description 7
• 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 7
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• 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 compound FC1=C(Cl)C(F)=C(F)C(C2=C(N3N=CN=C3N=C2Cl)NC2CCCC2)=C1F MZMNJILSZILXCA-UHFFFAOYSA-N 0.000 claims description 7
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• 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 7
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