JP2017501177A5 - - Google Patents
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- JP2017501177A5 JP2017501177A5 JP2016541014A JP2016541014A JP2017501177A5 JP 2017501177 A5 JP2017501177 A5 JP 2017501177A5 JP 2016541014 A JP2016541014 A JP 2016541014A JP 2016541014 A JP2016541014 A JP 2016541014A JP 2017501177 A5 JP2017501177 A5 JP 2017501177A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- triazolo
- pyrimidin
- carboxamide
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 147
- 125000003545 alkoxy group Chemical group 0.000 claims description 68
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 68
- 125000005843 halogen group Chemical group 0.000 claims description 66
- 125000003282 alkyl amino group Chemical group 0.000 claims description 53
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 30
- -1 amino, phenyl Chemical group 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 208000024891 symptom Diseases 0.000 claims description 6
- 206010001935 American trypanosomiasis Diseases 0.000 claims description 5
- 208000024699 Chagas disease Diseases 0.000 claims description 5
- 208000004554 Leishmaniasis Diseases 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 208000029080 human African trypanosomiasis Diseases 0.000 claims description 5
- 229930183010 Amphotericin Natural products 0.000 claims description 4
- QGGFZZLFKABGNL-UHFFFAOYSA-N Amphotericin A Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCCC=CC=CC(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CCC(O)C(O)CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 QGGFZZLFKABGNL-UHFFFAOYSA-N 0.000 claims description 4
- 241000223109 Trypanosoma cruzi Species 0.000 claims description 4
- 229940009444 amphotericin Drugs 0.000 claims description 4
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- PFOYFBYIHCVQGB-XCCFGPONSA-N (4r,5s,6r)-2-[[(4r,5s,6r)-4-carboxy-6-[(1r)-1,2-dihydroxyethyl]-5-hydroxy-2-oxo-1,3,2$l^{5}-dioxastibinan-2-yl]oxy]-6-[(1r)-1,2-dihydroxyethyl]-5-hydroxy-2-oxo-1,3,2$l^{5}-dioxastibinane-4-carboxylic acid Chemical group O1[C@@H](C(O)=O)[C@@H](O)[C@@H]([C@H](O)CO)O[Sb]1(=O)O[Sb]1(=O)O[C@@H](C(O)=O)[C@@H](O)[C@@H]([C@H](O)CO)O1 PFOYFBYIHCVQGB-XCCFGPONSA-N 0.000 claims description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 2
- CULUWZNBISUWAS-UHFFFAOYSA-N Benznidazole Chemical group [O-][N+](=O)C1=NC=CN1CC(=O)NCC1=CC=CC=C1 CULUWZNBISUWAS-UHFFFAOYSA-N 0.000 claims description 2
- UOZODPSAJZTQNH-UHFFFAOYSA-N Paromomycin II Natural products NC1C(O)C(O)C(CN)OC1OC1C(O)C(OC2C(C(N)CC(N)C2O)OC2C(C(O)C(O)C(CO)O2)N)OC1CO UOZODPSAJZTQNH-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229960004001 benznidazole Drugs 0.000 claims description 2
- 229940053382 meglumine antimonate Drugs 0.000 claims description 2
- XOGYVDXPYVPAAQ-SESJOKTNSA-M meglumine antimoniate Chemical compound O[Sb](=O)=O.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO XOGYVDXPYVPAAQ-SESJOKTNSA-M 0.000 claims description 2
- PQLXHQMOHUQAKB-UHFFFAOYSA-N miltefosine Chemical compound CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C PQLXHQMOHUQAKB-UHFFFAOYSA-N 0.000 claims description 2
- 229960003775 miltefosine Drugs 0.000 claims description 2
- UOZODPSAJZTQNH-LSWIJEOBSA-N paromomycin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO UOZODPSAJZTQNH-LSWIJEOBSA-N 0.000 claims description 2
- 229960001914 paromomycin Drugs 0.000 claims description 2
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical group C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 claims description 2
- 229960004448 pentamidine Drugs 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 claims description 2
- 229960005314 suramin Drugs 0.000 claims description 2
- VFJMWZSEQZMVTB-UHFFFAOYSA-N N-[4-fluoro-3-(6-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)N2CCCC2)=N1 VFJMWZSEQZMVTB-UHFFFAOYSA-N 0.000 claims 2
- RGPFEUJUCVLECK-UHFFFAOYSA-N N-[4-fluoro-3-[6-(2-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C2=C(C=CC=C2)F)=N1 RGPFEUJUCVLECK-UHFFFAOYSA-N 0.000 claims 2
- ARFHIAQFJWUCFH-IZZDOVSWSA-N Nifurtimox Chemical compound CC1CS(=O)(=O)CCN1\N=C\C1=CC=C([N+]([O-])=O)O1 ARFHIAQFJWUCFH-IZZDOVSWSA-N 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- 229960002644 nifurtimox Drugs 0.000 claims 2
- RJMYDSSPWRETSL-BEFAXECRSA-N (2S,4R)-4-fluoro-1-[[4-fluoro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]carbamoyl]pyrrolidine-2-carboxylic acid Chemical compound F[C@@H]1C[C@H](N(C1)C(NC1=CC(=C(C=C1)F)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1)=O)C(=O)O RJMYDSSPWRETSL-BEFAXECRSA-N 0.000 claims 1
- SFGVRDFCSIXHNK-SNVBAGLBSA-N (3R)-N-[3-(6-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-4-fluorophenyl]-3-fluoropyrrolidine-1-carboxamide Chemical compound ClC=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)N2C[C@@H](CC2)F SFGVRDFCSIXHNK-SNVBAGLBSA-N 0.000 claims 1
- AKJACVYFLUIXNN-GFCCVEGCSA-N (3R)-N-[3-(6-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-4-fluorophenyl]-3-methoxypyrrolidine-1-carboxamide Chemical compound ClC=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)N2C[C@@H](CC2)OC AKJACVYFLUIXNN-GFCCVEGCSA-N 0.000 claims 1
- QINQFYLSDQUJFV-OAHLLOKOSA-N (3R)-N-[3-[6-(3,6-dihydro-2H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-3-fluoropyrrolidine-1-carboxamide Chemical compound O1CCC(=CC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)N2C[C@@H](CC2)F QINQFYLSDQUJFV-OAHLLOKOSA-N 0.000 claims 1
- BCCBAMHUCZTNET-GOSISDBHSA-N (3R)-N-[4-fluoro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-3-methoxypyrrolidine-1-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)N1C[C@@H](CC1)OC)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1 BCCBAMHUCZTNET-GOSISDBHSA-N 0.000 claims 1
- GQAQMVKXMCKWNT-UHFFFAOYSA-N 3,3-difluoro-N-[4-fluoro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]azetidine-1-carboxamide Chemical compound FC1(CN(C1)C(=O)NC1=CC(=C(C=C1)F)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1)F GQAQMVKXMCKWNT-UHFFFAOYSA-N 0.000 claims 1
- DTXRJQRSZZIGKX-UHFFFAOYSA-N 3-[3-[6-(3,6-dihydro-2H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-1,1-dimethylurea Chemical compound O1CCC(=CC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(N(C)C)=O DTXRJQRSZZIGKX-UHFFFAOYSA-N 0.000 claims 1
- FYQVCYOKOABRSI-UHFFFAOYSA-N 3-fluoro-N-[4-fluoro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]azetidine-1-carboxamide Chemical compound FC1CN(C1)C(=O)NC1=CC(=C(C=C1)F)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1 FYQVCYOKOABRSI-UHFFFAOYSA-N 0.000 claims 1
- WXZFCGRYVWYYTG-UHFFFAOYSA-N GNF6702 Chemical compound O1C(C)=NC(C)=C1C(=O)NC1=CC=C(F)C(C2=NN3C=C(C=NC3=N2)C=2N=CC=CC=2)=C1 WXZFCGRYVWYYTG-UHFFFAOYSA-N 0.000 claims 1
- XQMWRLONVZQVCA-UHFFFAOYSA-N N-[2,4-difluoro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=CC(=C1C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1)F)NC(=O)C1=C(N=C(O1)C)C XQMWRLONVZQVCA-UHFFFAOYSA-N 0.000 claims 1
- RBNUUPWPVKPMMF-UHFFFAOYSA-N N-[2,4-difluoro-5-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C(=C1)F)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1)NC(=O)C1=C(N=C(O1)C)C RBNUUPWPVKPMMF-UHFFFAOYSA-N 0.000 claims 1
- RAYOESJRAPQPNA-UHFFFAOYSA-N N-[3-(6-bromo-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-4-chlorophenyl]furan-2-carboxamide Chemical compound BrC=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2Cl)NC(=O)C=2OC=CC2 RAYOESJRAPQPNA-UHFFFAOYSA-N 0.000 claims 1
- WNNOVRFDLXNVJB-UHFFFAOYSA-N N-[3-(6-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound ClC=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C WNNOVRFDLXNVJB-UHFFFAOYSA-N 0.000 claims 1
- ZQWKZFGKOLZSPI-UHFFFAOYSA-N N-[3-(6-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-4-fluorophenyl]-2-methyl-1,3-oxazole-5-carboxamide Chemical compound ClC=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=CN=C(O2)C ZQWKZFGKOLZSPI-UHFFFAOYSA-N 0.000 claims 1
- FHRLPIZDHRMMQD-UHFFFAOYSA-N N-[3-(6-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-4-fluorophenyl]-3,3-difluoroazetidine-1-carboxamide Chemical compound ClC=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)N2CC(C2)(F)F FHRLPIZDHRMMQD-UHFFFAOYSA-N 0.000 claims 1
- QYCKDUAKNYAVIT-UHFFFAOYSA-N N-[3-(6-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-4-fluorophenyl]-3-fluoroazetidine-1-carboxamide Chemical compound ClC=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)N2CC(C2)F QYCKDUAKNYAVIT-UHFFFAOYSA-N 0.000 claims 1
- ZFLXEULSRFMDEX-UHFFFAOYSA-N N-[3-(6-cyclopropyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound C1(CC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C ZFLXEULSRFMDEX-UHFFFAOYSA-N 0.000 claims 1
- ZFBPPFZHUJIKNH-UHFFFAOYSA-N N-[3-[6-(1-benzyl-3,6-dihydro-2H-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)N1CCC(=CC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C ZFBPPFZHUJIKNH-UHFFFAOYSA-N 0.000 claims 1
- DGHKVAQTVVNIPN-UHFFFAOYSA-N N-[3-[6-(2,5-dihydro-1H-pyrrol-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound N1CC(=CC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C DGHKVAQTVVNIPN-UHFFFAOYSA-N 0.000 claims 1
- JHMHAYJMNXQHLG-UHFFFAOYSA-N N-[3-[6-(3,3-difluoroazetidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1(CN(C1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C)F JHMHAYJMNXQHLG-UHFFFAOYSA-N 0.000 claims 1
- DYZAPNHCTAAOEM-UHFFFAOYSA-N N-[3-[6-(3,6-dihydro-2H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound O1CCC(=CC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C DYZAPNHCTAAOEM-UHFFFAOYSA-N 0.000 claims 1
- INJQSWQCBDHFGV-UHFFFAOYSA-N N-[3-[6-(3,6-dihydro-2H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-3-fluoroazetidine-1-carboxamide Chemical compound O1CCC(=CC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)N2CC(C2)F INJQSWQCBDHFGV-UHFFFAOYSA-N 0.000 claims 1
- BJHZNOFPFKPMET-UHFFFAOYSA-N N-[3-[6-(3,6-dihydro-2H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]azetidine-1-carboxamide Chemical compound O1CCC(=CC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)N2CCC2 BJHZNOFPFKPMET-UHFFFAOYSA-N 0.000 claims 1
- UQZAWLLGLJCPTI-UHFFFAOYSA-N N-[3-[6-(3,6-dihydro-2H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound O1CCC(=CC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2)NC(=O)C2=C(N=C(O2)C)C UQZAWLLGLJCPTI-UHFFFAOYSA-N 0.000 claims 1
- ZAPFDTJBYGSHRW-UHFFFAOYSA-N N-[3-[6-(3-chloropyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound ClC=1C(=NC=CC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C ZAPFDTJBYGSHRW-UHFFFAOYSA-N 0.000 claims 1
- PBKDPASYHAXBEW-UHFFFAOYSA-N N-[3-[6-(5-chloropyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound ClC=1C=C(C=NC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C PBKDPASYHAXBEW-UHFFFAOYSA-N 0.000 claims 1
- GWXKHJPBBUWKRC-UHFFFAOYSA-N N-[3-[6-(7-azabicyclo[2.2.1]hept-2-en-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound C12C(=CC(CC1)N2)C=2C=NC=1N(C2)N=C(N1)C=1C=C(C=CC1F)NC(=O)C1=C(N=C(O1)C)C GWXKHJPBBUWKRC-UHFFFAOYSA-N 0.000 claims 1
- CCRWYMXDQSVFHU-UHFFFAOYSA-N N-[3-[6-(azetidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound N1(CCC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C CCRWYMXDQSVFHU-UHFFFAOYSA-N 0.000 claims 1
- XBTIJJZSIAIOGR-UHFFFAOYSA-N N-[3-[6-(cyclopenten-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound C1(=CCCC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C XBTIJJZSIAIOGR-UHFFFAOYSA-N 0.000 claims 1
- KCSMCFBFTIHJRH-UHFFFAOYSA-N N-[3-[6-(diethylamino)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound C(C)N(C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C)CC KCSMCFBFTIHJRH-UHFFFAOYSA-N 0.000 claims 1
- MZBMHCKLGYPNMS-UHFFFAOYSA-N N-[3-[6-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound CN(C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C)C MZBMHCKLGYPNMS-UHFFFAOYSA-N 0.000 claims 1
- QCHYCCSYVQBBST-DLBZAZTESA-N N-[3-[6-[(1S,5R)-8-azabicyclo[3.2.1]oct-2-en-3-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound [C@H]12CC(=C[C@H](CC1)N2)C=2C=NC=1N(C2)N=C(N1)C=1C=C(C=CC1F)NC(=O)C1=C(N=C(O1)C)C QCHYCCSYVQBBST-DLBZAZTESA-N 0.000 claims 1
- SAQPDOGLYJCGJM-UHFFFAOYSA-N N-[3-[6-[3-(difluoromethyl)pyridin-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC(C=1C(=NC=CC1)C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C)F SAQPDOGLYJCGJM-UHFFFAOYSA-N 0.000 claims 1
- DQRJYBNALXMGQU-UHFFFAOYSA-N N-[3-[6-[ethyl(methyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-4-fluorophenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound C(C)N(C=1C=NC=2N(C1)N=C(N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C)C DQRJYBNALXMGQU-UHFFFAOYSA-N 0.000 claims 1
- UTZXTOGKRSSYMC-UHFFFAOYSA-N N-[4-chloro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]furan-2-carboxamide Chemical compound ClC1=C(C=C(C=C1)NC(=O)C=1OC=CC1)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1 UTZXTOGKRSSYMC-UHFFFAOYSA-N 0.000 claims 1
- WOFHYNMCCXXWTN-UHFFFAOYSA-N N-[4-chloro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]pyrrolidine-1-carboxamide Chemical compound ClC1=C(C=C(C=C1)NC(=O)N1CCCC1)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1 WOFHYNMCCXXWTN-UHFFFAOYSA-N 0.000 claims 1
- JJVVJJTXSUHRJV-UHFFFAOYSA-N N-[4-fluoro-3-(6-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)N2CCOCC2)=N1 JJVVJJTXSUHRJV-UHFFFAOYSA-N 0.000 claims 1
- HAZSOZXXVLAJEU-UHFFFAOYSA-N N-[4-fluoro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1 HAZSOZXXVLAJEU-UHFFFAOYSA-N 0.000 claims 1
- LMZMDYJLHSYMBU-UHFFFAOYSA-N N-[4-fluoro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2-methyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=CN=C(O1)C)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1 LMZMDYJLHSYMBU-UHFFFAOYSA-N 0.000 claims 1
- NCBJEYCGFPCYDC-UHFFFAOYSA-N N-[4-fluoro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-3,3-dimethylazetidine-1-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)N1CC(C1)(C)C)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1 NCBJEYCGFPCYDC-UHFFFAOYSA-N 0.000 claims 1
- QPFUZDPGJCUAIX-UHFFFAOYSA-N N-[4-fluoro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-3-methylazetidine-1-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)N1CC(C1)C)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1 QPFUZDPGJCUAIX-UHFFFAOYSA-N 0.000 claims 1
- IJRPXINFPLIPGD-UHFFFAOYSA-N N-[4-fluoro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]azetidine-1-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)N1CCC1)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1 IJRPXINFPLIPGD-UHFFFAOYSA-N 0.000 claims 1
- ZQNOIOZONWZJAU-UHFFFAOYSA-N N-[4-fluoro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]cyclobutanecarboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1CCC1)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1 ZQNOIOZONWZJAU-UHFFFAOYSA-N 0.000 claims 1
- COZIECYBULLICV-UHFFFAOYSA-N N-[4-fluoro-3-(6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]pyrrolidine-1-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)N1CCCC1)C1=NN2C(N=CC(=C2)C2=CC=CC=C2)=N1 COZIECYBULLICV-UHFFFAOYSA-N 0.000 claims 1
- JEWNWAPEGHYYFP-UHFFFAOYSA-N N-[4-fluoro-3-(6-piperazin-1-yl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)N2CCNCC2)=N1 JEWNWAPEGHYYFP-UHFFFAOYSA-N 0.000 claims 1
- PLPZYXLBJWNYCI-UHFFFAOYSA-N N-[4-fluoro-3-(6-piperidin-1-yl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)N2CCCCC2)=N1 PLPZYXLBJWNYCI-UHFFFAOYSA-N 0.000 claims 1
- ZRUSTYCFSHDJRI-UHFFFAOYSA-N N-[4-fluoro-3-(6-propan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C(C)C)=N1 ZRUSTYCFSHDJRI-UHFFFAOYSA-N 0.000 claims 1
- PLVQQRYVMOHPMQ-UHFFFAOYSA-N N-[4-fluoro-3-(6-pyrazin-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C2=NC=CN=C2)=N1 PLVQQRYVMOHPMQ-UHFFFAOYSA-N 0.000 claims 1
- KULHHHNEDOBTCH-UHFFFAOYSA-N N-[4-fluoro-3-(6-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-N,2,4-trimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)N(C(=O)C1=C(N=C(O1)C)C)C)C1=NN2C(N=CC(=C2)C2=NC=CC=C2)=N1 KULHHHNEDOBTCH-UHFFFAOYSA-N 0.000 claims 1
- CSUOLGWQOUDDIV-UHFFFAOYSA-N N-[4-fluoro-3-(6-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]azetidine-1-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)N1CCC1)C1=NN2C(N=CC(=C2)C2=NC=CC=C2)=N1 CSUOLGWQOUDDIV-UHFFFAOYSA-N 0.000 claims 1
- GXUOOCWPMSBNPF-UHFFFAOYSA-N N-[4-fluoro-3-(6-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C=2C=NC=CC2)=N1 GXUOOCWPMSBNPF-UHFFFAOYSA-N 0.000 claims 1
- LLFLOSOPMKRYTR-UHFFFAOYSA-N N-[4-fluoro-3-(6-trimethylsilyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)[Si](C)(C)C)=N1 LLFLOSOPMKRYTR-UHFFFAOYSA-N 0.000 claims 1
- SBOJXOMKQVRXDT-UHFFFAOYSA-N N-[4-fluoro-3-([1,2,4]triazolo[1,5-a]pyrimidin-2-yl)phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound N1=C(N=C2N1C=CC=N2)C=2C=C(C=CC2F)NC(=O)C2=C(N=C(O2)C)C SBOJXOMKQVRXDT-UHFFFAOYSA-N 0.000 claims 1
- HNKWCMPOPKNVAV-UHFFFAOYSA-N N-[4-fluoro-3-[6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C=2CCN(CC2)C)=N1 HNKWCMPOPKNVAV-UHFFFAOYSA-N 0.000 claims 1
- INXXKQVWJRJERS-UHFFFAOYSA-N N-[4-fluoro-3-[6-(1-methyl-3,6-dihydro-2H-pyridin-5-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C=2CN(CCC2)C)=N1 INXXKQVWJRJERS-UHFFFAOYSA-N 0.000 claims 1
- WNBUPWYLZZWIFI-UHFFFAOYSA-N N-[4-fluoro-3-[6-(1-methylpyrazol-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C2=NN(C=C2)C)=N1 WNBUPWYLZZWIFI-UHFFFAOYSA-N 0.000 claims 1
- MJNVJSNKZHTDAS-UHFFFAOYSA-N N-[4-fluoro-3-[6-(2,2,6,6-tetramethyl-1,3-dihydropyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C=2CC(NC(C2)(C)C)(C)C)=N1 MJNVJSNKZHTDAS-UHFFFAOYSA-N 0.000 claims 1
- JNHTXVDQFFFJIT-UHFFFAOYSA-N N-[4-fluoro-3-[6-(2,2,6,6-tetramethyl-3H-pyran-4-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C=2CC(OC(C2)(C)C)(C)C)=N1 JNHTXVDQFFFJIT-UHFFFAOYSA-N 0.000 claims 1
- HFTMAZYRAYXAFH-UHFFFAOYSA-N N-[4-fluoro-3-[6-(2-methoxypyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C=2C(=NC=CC2)OC)=N1 HFTMAZYRAYXAFH-UHFFFAOYSA-N 0.000 claims 1
- ZCQXUDATWPRWNX-UHFFFAOYSA-N N-[4-fluoro-3-[6-(2-methylpyrazol-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C2=CC=NN2C)=N1 ZCQXUDATWPRWNX-UHFFFAOYSA-N 0.000 claims 1
- IBFZTNBBRHSTDI-UHFFFAOYSA-N N-[4-fluoro-3-[6-(3-fluoroazetidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)N2CC(C2)F)=N1 IBFZTNBBRHSTDI-UHFFFAOYSA-N 0.000 claims 1
- DFEWMGPEKUHLSL-UHFFFAOYSA-N N-[4-fluoro-3-[6-(3-fluoropyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C2=NC=CC=C2F)=N1 DFEWMGPEKUHLSL-UHFFFAOYSA-N 0.000 claims 1
- KGJBVEXBERFKNV-UHFFFAOYSA-N N-[4-fluoro-3-[6-(3-methoxypyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C2=NC=CC=C2OC)=N1 KGJBVEXBERFKNV-UHFFFAOYSA-N 0.000 claims 1
- GNVVPYCWVLCWKV-UHFFFAOYSA-N N-[4-fluoro-3-[6-(3-methylpyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C2=NC=CC=C2C)=N1 GNVVPYCWVLCWKV-UHFFFAOYSA-N 0.000 claims 1
- CHZLXLROXBCGLE-UHFFFAOYSA-N N-[4-fluoro-3-[6-(3-methylpyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-N,2,4-trimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)N(C(=O)C1=C(N=C(O1)C)C)C)C1=NN2C(N=CC(=C2)C2=NC=CC=C2C)=N1 CHZLXLROXBCGLE-UHFFFAOYSA-N 0.000 claims 1
- MQLRVDKHYWWUBA-UHFFFAOYSA-N N-[4-fluoro-3-[6-(5-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C=2C=NNC2C)=N1 MQLRVDKHYWWUBA-UHFFFAOYSA-N 0.000 claims 1
- LFUDCUGGAVDJDG-UHFFFAOYSA-N N-[4-fluoro-3-[6-(5-methylpyrazin-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C2=NC=C(N=C2)C)=N1 LFUDCUGGAVDJDG-UHFFFAOYSA-N 0.000 claims 1
- DMVFTOAMSCOGII-UHFFFAOYSA-N N-[4-fluoro-3-[6-(6-methoxypyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C2=NC(=CC=C2)OC)=N1 DMVFTOAMSCOGII-UHFFFAOYSA-N 0.000 claims 1
- MBWHEXRVNOQODU-UHFFFAOYSA-N N-[4-fluoro-3-[6-(6-methoxypyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C=2C=NC(=CC2)OC)=N1 MBWHEXRVNOQODU-UHFFFAOYSA-N 0.000 claims 1
- YFLCTPSABGPJEO-UHFFFAOYSA-N N-[4-fluoro-3-[6-(6-morpholin-4-ylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C=2C=NC(=CC2)N2CCOCC2)=N1 YFLCTPSABGPJEO-UHFFFAOYSA-N 0.000 claims 1
- KTDQEQUDQAGYNA-UHFFFAOYSA-N N-[4-fluoro-3-[6-(6-piperazin-1-ylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C=2C=NC(=CC2)N2CCNCC2)=N1 KTDQEQUDQAGYNA-UHFFFAOYSA-N 0.000 claims 1
- ZRCOLFWDYQBQKK-UHFFFAOYSA-N N-[4-fluoro-3-[6-(6-propan-2-yloxypyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]phenyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide Chemical compound FC1=C(C=C(C=C1)NC(=O)C1=C(N=C(O1)C)C)C1=NN2C(N=CC(=C2)C=2C=NC(=CC2)OC(C)C)=N1 ZRCOLFWDYQBQKK-UHFFFAOYSA-N 0.000 claims 1
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| EP3303336A1 (en) | 2015-05-29 | 2018-04-11 | GlaxoSmithKline Intellectual Property Development Limited | Imidazo[1,2-b][1,2,4]triazine derivatives as antiparasitic agents |
| PL3331885T3 (pl) * | 2015-08-07 | 2021-06-14 | Glaxosmithkline Intellectual Property Development Limited | Związki |
| US10399966B2 (en) | 2016-01-21 | 2019-09-03 | University Of Washington | Compounds for treatment of trypanosomes and neurological pathogens and uses thereof |
| US12018000B2 (en) | 2017-03-27 | 2024-06-25 | HYDRO-QUéBEC | Lithium salts of cyano-substituted imidazole for lithium ion batteries |
| JOP20190278A1 (ar) * | 2017-05-31 | 2019-11-28 | Novartis Ag | مركبات 5، 6-ثنائية الحلقة مندمجة وتركيبات لعلاج الأمراض الطفيلية |
| EA039324B1 (ru) * | 2017-11-06 | 2022-01-13 | Новартис Аг | 5,6–конденсированные бициклические соединения и композиции для лечения паразитарных заболеваний |
| TW202028208A (zh) * | 2018-10-09 | 2020-08-01 | 瑞士商諾華公司 | N-(4-氟-3-(6-(3-甲基吡啶-2-基)-[1,2,4]三唑并[1,5-a]嘧啶-2-基)苯基)-2,4-二甲基㗁唑-5-甲醯胺固體形式 |
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- 2016-06-09 CL CL2016001421A patent/CL2016001421A1/es unknown
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- 2016-06-17 GT GT201600131A patent/GT201600131A/es unknown
- 2016-06-17 PH PH12016501198A patent/PH12016501198A1/en unknown
- 2016-06-29 ZA ZA2016/04415A patent/ZA201604415B/en unknown
- 2016-08-16 EC ECIEPI201667921A patent/ECSP16067921A/es unknown
-
2017
- 2017-05-19 US US15/600,183 patent/US10085989B2/en active Active
-
2018
- 2018-08-29 US US16/116,418 patent/US10596175B2/en active Active
- 2018-12-05 CY CY181101300T patent/CY1121060T1/el unknown
-
2020
- 2020-02-03 US US16/780,628 patent/US11123348B2/en active Active
-
2021
- 2021-08-10 US US17/398,852 patent/US20210369716A1/en not_active Abandoned
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