JP2014511887A5 - - Google Patents
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- Publication number
- JP2014511887A5 JP2014511887A5 JP2014505584A JP2014505584A JP2014511887A5 JP 2014511887 A5 JP2014511887 A5 JP 2014511887A5 JP 2014505584 A JP2014505584 A JP 2014505584A JP 2014505584 A JP2014505584 A JP 2014505584A JP 2014511887 A5 JP2014511887 A5 JP 2014511887A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- phenyl
- triazolo
- pyridin
- benzamide
- 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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- -1 hydroxy - Chemical class 0.000 claims 102
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 55
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 21
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 13
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
- 150000001204 N-oxides Chemical class 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- XEHCIJQQJFATFU-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]benzamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=CC=C1 XEHCIJQQJFATFU-UHFFFAOYSA-N 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 2
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 229930012538 Paclitaxel Natural products 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229960001592 paclitaxel Drugs 0.000 claims 2
- 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 2
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- DOFAIOAQLWCBAR-UHFFFAOYSA-N 2-(2,2,2-trifluoroethoxy)benzamide Chemical compound NC(=O)C1=CC=CC=C1OCC(F)(F)F DOFAIOAQLWCBAR-UHFFFAOYSA-N 0.000 claims 1
- VOXBZHOHGGBLCQ-UHFFFAOYSA-N 2-amino-3,7-dihydropurine-6-thione;hydrate Chemical compound O.N1C(N)=NC(=S)C2=C1N=CN2.N1C(N)=NC(=S)C2=C1N=CN2 VOXBZHOHGGBLCQ-UHFFFAOYSA-N 0.000 claims 1
- HDAACQFIZNADSI-UHFFFAOYSA-N 2-fluoro-n-[(4-fluorophenyl)methyl]-4-[2-[4-[(1-hydroxy-2-methylpropan-2-yl)carbamoyl]-2-methoxyanilino]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]benzamide Chemical compound COC1=CC(C(=O)NC(C)(C)CO)=CC=C1NC1=NN2C=C(C=3C=C(F)C(C(=O)NCC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 HDAACQFIZNADSI-UHFFFAOYSA-N 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- BJELOFSVOCGXPY-UHFFFAOYSA-N 3-ethoxy-4-[[6-[4-[(4-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-(2-hydroxyethyl)-n-methylbenzamide Chemical compound CCOC1=CC(C(=O)N(C)CCO)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 BJELOFSVOCGXPY-UHFFFAOYSA-N 0.000 claims 1
- DMQSPAQNIBRPIY-UHFFFAOYSA-N 3-ethoxy-4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-(2-hydroxyethyl)-n-methylbenzamide Chemical compound CCOC1=CC(C(=O)N(C)CCO)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 DMQSPAQNIBRPIY-UHFFFAOYSA-N 0.000 claims 1
- VOKDMYZGCMSTTP-UHFFFAOYSA-N 3-ethoxy-n-ethyl-4-[[6-[4-[(4-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-methylbenzamide Chemical compound CCOC1=CC(C(=O)N(C)CC)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 VOKDMYZGCMSTTP-UHFFFAOYSA-N 0.000 claims 1
- FBXQYZHNMDSLGL-UHFFFAOYSA-N 3-ethoxy-n-ethyl-4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-methylbenzamide Chemical compound CCOC1=CC(C(=O)N(C)CC)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 FBXQYZHNMDSLGL-UHFFFAOYSA-N 0.000 claims 1
- WZUGEJQBZJJMJO-UHFFFAOYSA-N 4-[[6-[4-[(4-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-methoxy-n,n-dimethylbenzamide Chemical compound COC1=CC(C(=O)N(C)C)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 WZUGEJQBZJJMJO-UHFFFAOYSA-N 0.000 claims 1
- WAPGIGHNANPHAZ-UHFFFAOYSA-N 4-[[6-[4-[(4-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 WAPGIGHNANPHAZ-UHFFFAOYSA-N 0.000 claims 1
- ZENOFAVGGROELN-UHFFFAOYSA-N 4-[[6-[4-[(4-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-methoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 ZENOFAVGGROELN-UHFFFAOYSA-N 0.000 claims 1
- HXJBGLHXJUGGNC-UHFFFAOYSA-N 4-[[6-[4-[(4-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-methylbenzamide Chemical compound CC1=CC(C(N)=O)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 HXJBGLHXJUGGNC-UHFFFAOYSA-N 0.000 claims 1
- XCZSLCPKGYMBJK-UHFFFAOYSA-N 4-[[6-[4-[(4-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-(1-hydroxy-2-methylpropan-2-yl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC(C)(C)CO)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 XCZSLCPKGYMBJK-UHFFFAOYSA-N 0.000 claims 1
- RMTIFIKNWIXLED-UHFFFAOYSA-N 4-[[6-[4-[(4-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-(2-hydroxy-2-methylpropyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCC(C)(C)O)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 RMTIFIKNWIXLED-UHFFFAOYSA-N 0.000 claims 1
- JZGAEJLZUUQEBJ-UHFFFAOYSA-N 4-[[6-[4-[(4-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-(2-hydroxyethyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCO)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 JZGAEJLZUUQEBJ-UHFFFAOYSA-N 0.000 claims 1
- JNSJBZIBGNVCTC-UHFFFAOYSA-N 4-[[6-[4-[(4-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-(3-fluoropropyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCF)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 JNSJBZIBGNVCTC-UHFFFAOYSA-N 0.000 claims 1
- RKTSDVIPUPCSPF-UHFFFAOYSA-N 4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-methoxy-n,n-dimethylbenzamide Chemical compound COC1=CC(C(=O)N(C)C)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 RKTSDVIPUPCSPF-UHFFFAOYSA-N 0.000 claims 1
- HMUGPPNQUFSYBS-UHFFFAOYSA-N 4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 HMUGPPNQUFSYBS-UHFFFAOYSA-N 0.000 claims 1
- YHWOPEAYOKDTJG-UHFFFAOYSA-N 4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n,n,3-trimethylbenzamide Chemical compound CC1=CC(C(=O)N(C)C)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 YHWOPEAYOKDTJG-UHFFFAOYSA-N 0.000 claims 1
- MEJBPOHVYYYUPR-UHFFFAOYSA-N 4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-(1-hydroxy-2-methylpropan-2-yl)-3-(2,2,2-trifluoroethoxy)benzamide Chemical compound FC(F)(F)COC1=CC(C(=O)NC(C)(CO)C)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 MEJBPOHVYYYUPR-UHFFFAOYSA-N 0.000 claims 1
- OGWRAFNNMGCIMI-UHFFFAOYSA-N 4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-(1-hydroxy-2-methylpropan-2-yl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC(C)(C)CO)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 OGWRAFNNMGCIMI-UHFFFAOYSA-N 0.000 claims 1
- DANWDACOBONHBO-UHFFFAOYSA-N 4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-(2-hydroxy-2-methylpropyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCC(C)(C)O)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 DANWDACOBONHBO-UHFFFAOYSA-N 0.000 claims 1
- QDEBDTKUOGBJOL-UHFFFAOYSA-N 4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-(2-hydroxyethyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCO)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 QDEBDTKUOGBJOL-UHFFFAOYSA-N 0.000 claims 1
- WCSRPFZWEISFSM-UHFFFAOYSA-N 4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-(3-fluoropropyl)-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCF)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 WCSRPFZWEISFSM-UHFFFAOYSA-N 0.000 claims 1
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 1
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims 1
- 108010006654 Bleomycin Proteins 0.000 claims 1
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 1
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims 1
- GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 claims 1
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 claims 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 1
- BFZKMNSQCNVFGM-UCEYFQQTSA-N Sagopilone Chemical compound O1C(=O)C[C@H](O)C(C)(C)C(=O)[C@H](CC=C)[C@@H](O)[C@@H](C)CCC[C@@]2(C)O[C@H]2C[C@H]1C1=CC=C(SC(C)=N2)C2=C1 BFZKMNSQCNVFGM-UCEYFQQTSA-N 0.000 claims 1
- 229940123237 Taxane Drugs 0.000 claims 1
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims 1
- DACWQSNZECJJGG-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CN=C21 DACWQSNZECJJGG-UHFFFAOYSA-N 0.000 claims 1
- 229940009456 adriamycin Drugs 0.000 claims 1
- 230000002280 anti-androgenic effect Effects 0.000 claims 1
- 239000000051 antiandrogen Substances 0.000 claims 1
- 229960000997 bicalutamide Drugs 0.000 claims 1
- 229960001561 bleomycin Drugs 0.000 claims 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims 1
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims 1
- 229960001467 bortezomib Drugs 0.000 claims 1
- 229960004117 capecitabine Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229960004630 chlorambucil Drugs 0.000 claims 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- 229960004397 cyclophosphamide Drugs 0.000 claims 1
- 229960000978 cyproterone acetate Drugs 0.000 claims 1
- UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 claims 1
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| US9284323B2 (en) | 2012-01-04 | 2016-03-15 | Gilead Sciences, Inc. | Naphthalene acetic acid derivatives against HIV infection |
| US9376392B2 (en) | 2012-01-04 | 2016-06-28 | Gilead Sciences, Inc. | 2-(tert-butoxy)-2-(7-methylquinolin-6-yl) acetic acid derivatives for treating AIDS |
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| EP2860177A3 (en) | 2013-09-20 | 2015-06-10 | Bayer Intellectual Property GmbH | Synthesis of functionalized arenes |
| ES2966392T3 (es) | 2015-04-17 | 2024-04-22 | Crossfire Oncology Holding B V | Biomarcadores pronósticos para quimioterapia inhibidora de TTK |
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| CA2693232A1 (en) * | 2007-07-18 | 2009-01-22 | Novartis Ag | Bicyclic heteroaryl compounds and their use as kinase inhibitors |
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| SG173610A1 (en) | 2009-02-13 | 2011-09-29 | Fovea Pharmaceuticals Sa | [1, 2, 4] triazolo [1, 5 -a] pyridines as kinase inhibitors |
| JP6168773B2 (ja) | 2009-04-29 | 2017-07-26 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換イミダゾキノキサリン |
| JP5728683B2 (ja) | 2009-09-04 | 2015-06-03 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | チロシンスレオニンキナーゼ阻害剤としての置換アミノキノキサリン |
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