NZ523807A - Substituted-triazolopyrimidines as anticancer agents - Google Patents

Info

Publication number

NZ523807A

NZ523807A NZ523807A NZ52380701A NZ523807A NZ 523807 A NZ523807 A NZ 523807A NZ 523807 A NZ523807 A NZ 523807A NZ 52380701 A NZ52380701 A NZ 52380701A NZ 523807 A NZ523807 A NZ 523807A

Authority

NZ

New Zealand

Prior art keywords

chloro

triazolo

carbon atoms

pyrimidin

optionally substituted

Prior art date

2000-06-30

Links

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• Global Dossier
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• -1 Substituted-triazolopyrimidines Chemical class 0.000 title claims description 99
• 239000002246 antineoplastic agent Substances 0.000 title description 9
• 150000003839 salts Chemical class 0.000 claims abstract description 39
• 102000029749 Microtubule Human genes 0.000 claims abstract description 32
• 108091022875 Microtubule Proteins 0.000 claims abstract description 32
• 210000004688 microtubule Anatomy 0.000 claims abstract description 32
• 102000004243 Tubulin Human genes 0.000 claims abstract description 25
• 108090000704 Tubulin Proteins 0.000 claims abstract description 25
• 230000012010 growth Effects 0.000 claims abstract description 25
• 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 23
• 241000124008 Mammalia Species 0.000 claims abstract description 18
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 14
• 210000004881 tumor cell Anatomy 0.000 claims abstract description 12
• 201000010099 disease Diseases 0.000 claims abstract description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
• 230000029115 microtubule polymerization Effects 0.000 claims abstract description 8
• 230000001737 promoting effect Effects 0.000 claims abstract description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 618
• 150000001875 compounds Chemical class 0.000 claims description 122
• 125000000217 alkyl group Chemical group 0.000 claims description 105
• 125000000623 heterocyclic group Chemical group 0.000 claims description 73
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
• 239000001257 hydrogen Substances 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
• 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 46
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 42
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 39
• 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 38
• 125000003118 aryl group Chemical group 0.000 claims description 38
• 229910052736 halogen Inorganic materials 0.000 claims description 38
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 35
• 125000003545 alkoxy group Chemical group 0.000 claims description 34
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 32
• 125000004414 alkyl thio group Chemical group 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 31
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 29
• 150000001412 amines Chemical class 0.000 claims description 28
• 125000001188 haloalkyl group Chemical group 0.000 claims description 28
• 150000002367 halogens Chemical class 0.000 claims description 28
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 27
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 25
• 239000003814 drug Substances 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 24
• 229910003827 NRaRb Inorganic materials 0.000 claims description 23
• 125000003282 alkyl amino group Chemical group 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 21
• 238000011282 treatment Methods 0.000 claims description 20
• 125000005843 halogen group Chemical group 0.000 claims description 18
• 125000003107 substituted aryl group Chemical group 0.000 claims description 18
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 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 15
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 125000006413 ring segment Chemical group 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
• 206010048723 Multiple-drug resistance Diseases 0.000 claims description 13
• 125000004429 atom Chemical group 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 12
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 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 11
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 11
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
• 102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 claims description 7
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
• 125000004104 aryloxy group Chemical group 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 6
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 5
• 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 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 201000001441 melanoma Diseases 0.000 claims description 5
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 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 4
• 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 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
• 229930192474 thiophene Natural products 0.000 claims description 4
• 125000004360 trifluorophenyl group Chemical group 0.000 claims description 4
• 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 3
• 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 3
• ZVFQAZBEAWJZDQ-UHFFFAOYSA-N 7-cyclohexyl-6-[2,6-difluoro-4-(2-methoxyethoxy)phenyl]-5-methoxy-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC1=CC(OCCOC)=CC(F)=C1C1=C(C2CCCCC2)N2N=CN=C2N=C1OC ZVFQAZBEAWJZDQ-UHFFFAOYSA-N 0.000 claims description 3
• 210000004556 brain Anatomy 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
• 230000010534 mechanism of action Effects 0.000 claims description 3
• NTADARNNAPPIBY-UHFFFAOYSA-N triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=CC=NC2=CN=NN12 NTADARNNAPPIBY-UHFFFAOYSA-N 0.000 claims description 3
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• MZRBHGLZBBYYNJ-UHFFFAOYSA-N 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4,4-dimethylpiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)(C)CCN1C1=C(C=2C(=CC=CC=2F)Cl)C(Cl)=NC2=NC=NN12 MZRBHGLZBBYYNJ-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
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• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 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 claims 1
• 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 compound FC=1C=CC=C(Cl)C=1C=1C(Cl)=NC2=NC=NN2C=1N(CCC)CC1CC1 IHHZKKKAZISPPZ-UHFFFAOYSA-N 0.000 claims 1
• 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 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• CIAOQQHCXZACFV-UHFFFAOYSA-N 5-chloro-6-(3-chloro-4-methoxyphenyl)-n-cycloheptyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(NC2CCCCCC2)N2N=CN=C2N=C1Cl CIAOQQHCXZACFV-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• ZTFABGOHTLABRE-UHFFFAOYSA-N 5-chloro-6-[2,6-difluoro-4-(2,2,2-trifluoroethoxy)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(F)(F)F)C=C1F ZTFABGOHTLABRE-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• MHAUWNWUWARPFV-UHFFFAOYSA-N 5-chloro-n-(1,1,1-trifluoro-3-methylbutan-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(F)(F)F)=C1C1=C(F)C=C(F)C=C1F MHAUWNWUWARPFV-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• SGZNMGPEOOJMFJ-UHFFFAOYSA-N 5-chloro-n-(3,3-dimethylbutan-2-yl)-6-(2-methylphenyl)-[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=C1C SGZNMGPEOOJMFJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 compound ClC1=NC2=NC=NN2C(NC(C)C(C)C)=C1C1=C(F)C=C(F)C=C1F BMVBXRJVLUMWNN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
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