EA006483B1 - Замещенные триазолопиримидины в качестве противораковых средств - Google Patents

Info

Publication number

EA006483B1

EA006483B1 EA200300091A EA200300091A EA006483B1 EA 006483 B1 EA006483 B1 EA 006483B1 EA 200300091 A EA200300091 A EA 200300091A EA 200300091 A EA200300091 A EA 200300091A EA 006483 B1 EA006483 B1 EA 006483B1

Authority

EA

Eurasian Patent Office

Prior art keywords

chloro

triazolo

carbon atoms

alkyl

pyrimidine

Prior art date

2000-06-30

Links

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• -1 Substituted-triazolopyrimidines Chemical class 0.000 title claims description 778
• 239000002246 antineoplastic agent Substances 0.000 title description 7
• 238000000034 method Methods 0.000 claims abstract description 52
• 150000003839 salts Chemical class 0.000 claims abstract description 45
• 102000029749 Microtubule Human genes 0.000 claims abstract description 34
• 108091022875 Microtubule Proteins 0.000 claims abstract description 34
• 210000004688 microtubule Anatomy 0.000 claims abstract description 34
• 241000124008 Mammalia Species 0.000 claims abstract description 32
• 102000004243 Tubulin Human genes 0.000 claims abstract description 29
• 108090000704 Tubulin Proteins 0.000 claims abstract description 29
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 15
• 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 15
• 210000004881 tumor cell Anatomy 0.000 claims abstract description 15
• 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 9
• 230000012010 growth Effects 0.000 claims abstract description 8
• 230000001737 promoting effect Effects 0.000 claims abstract description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 654
• 125000000217 alkyl group Chemical group 0.000 claims description 288
• 125000000623 heterocyclic group Chemical group 0.000 claims description 213
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 187
• 150000001875 compounds Chemical class 0.000 claims description 186
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 175
• 125000003545 alkoxy group Chemical group 0.000 claims description 166
• 229910052736 halogen Inorganic materials 0.000 claims description 165
• 150000002367 halogens Chemical class 0.000 claims description 165
• 125000003282 alkyl amino group Chemical group 0.000 claims description 156
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 156
• 125000004414 alkyl thio group Chemical group 0.000 claims description 153
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 153
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 152
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 146
• 125000001188 haloalkyl group Chemical group 0.000 claims description 146
• 125000001424 substituent group Chemical group 0.000 claims description 145
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 144
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 134
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 134
• 125000001589 carboacyl group Chemical group 0.000 claims description 132
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 125
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 122
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 116
• 125000003118 aryl group Chemical group 0.000 claims description 102
• 210000004027 cell Anatomy 0.000 claims description 99
• 125000003342 alkenyl group Chemical group 0.000 claims description 61
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 57
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 57
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• 239000001257 hydrogen Substances 0.000 claims description 48
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 48
• 229930012538 Paclitaxel Natural products 0.000 claims description 41
• 229960001592 paclitaxel Drugs 0.000 claims description 41
• 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 41
• 125000004429 atom Chemical group 0.000 claims description 39
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
• 229910052801 chlorine Inorganic materials 0.000 claims description 34
• 239000000460 chlorine Substances 0.000 claims description 34
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 33
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 239000003814 drug Substances 0.000 claims description 27
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
• 238000006116 polymerization reaction Methods 0.000 claims description 23
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 22
• 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 22
• 125000000304 alkynyl group Chemical group 0.000 claims description 20
• 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 19
• 229910052740 iodine Inorganic materials 0.000 claims description 19
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 15
• 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 14
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 229920006395 saturated elastomer Polymers 0.000 claims description 13
• 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
• 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
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 9
• 230000005907 cancer growth Effects 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 230000036457 multidrug resistance Effects 0.000 claims description 9
• AJTJTUSLJKZKOV-UHFFFAOYSA-N 2-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC(CC1=NN2C(N=CC=C2N)=N1)(F)F AJTJTUSLJKZKOV-UHFFFAOYSA-N 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 8
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 7
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 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 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 229930192474 thiophene Natural products 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 6
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 208000032839 leukemia Diseases 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 5
• 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 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
• 239000003937 drug carrier Substances 0.000 claims description 5
• 230000005764 inhibitory process Effects 0.000 claims description 5
• 201000001441 melanoma Diseases 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 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 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
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 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 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
• YQGHXSJSLPQYKA-UHFFFAOYSA-N 2,5-dichloro-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(Cl)=NN12 YQGHXSJSLPQYKA-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• MKIKOGFWRFSLTJ-UHFFFAOYSA-N 4-[5-chloro-7-(1,1,1-trifluoropropan-2-ylamino)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-3,5-difluorophenol Chemical compound ClC1=NC2=NC=NN2C(NC(C)C(F)(F)F)=C1C1=C(F)C=C(O)C=C1F MKIKOGFWRFSLTJ-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• KKQDICRNUQLTJZ-UHFFFAOYSA-N 5-chloro-6-(2,6-difluorophenyl)-7-(2-ethylimidazol-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound CCC1=NC=CN1C1=C(C=2C(=CC=CC=2F)F)C(Cl)=NC2=NC=NN12 KKQDICRNUQLTJZ-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
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• 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 3
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• 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 3
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