EA023766B1 - Триазолопиридины - Google Patents

Info

Publication number

EA023766B1

EA023766B1 EA201301181A EA201301181A EA023766B1 EA 023766 B1 EA023766 B1 EA 023766B1 EA 201301181 A EA201301181 A EA 201301181A EA 201301181 A EA201301181 A EA 201301181A EA 023766 B1 EA023766 B1 EA 023766B1

Authority

EA

Eurasian Patent Office

Prior art keywords

amino

phenyl

triazolo

pyridin

benzamide

Prior art date

2011-04-21

Links

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• Global Dossier
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• 150000008523 triazolopyridines Chemical class 0.000 title abstract description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 373
• 238000000034 method Methods 0.000 claims abstract description 75
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• 201000010099 disease Diseases 0.000 claims abstract description 11
• 238000011282 treatment Methods 0.000 claims abstract description 8
• 238000004519 manufacturing process Methods 0.000 claims abstract description 7
• 238000011321 prophylaxis Methods 0.000 claims abstract 2
• -1 hydroxy- Chemical class 0.000 claims description 431
• 239000000203 mixture Substances 0.000 claims description 349
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 219
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 146
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 75
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 72
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 40
• 125000001424 substituent group Chemical group 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 34
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 29
• 125000005843 halogen group Chemical group 0.000 claims description 29
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 25
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 23
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 20
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 18
• 238000005859 coupling reaction Methods 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
• 238000006243 chemical reaction Methods 0.000 claims description 15
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 14
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims description 11
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 10
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 7
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 7
• 230000001413 cellular effect Effects 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• AXNCKQLSNLIGOA-UHFFFAOYSA-N n-(2-hydroxy-2-methylpropyl)benzamide Chemical compound CC(C)(O)CNC(=O)C1=CC=CC=C1 AXNCKQLSNLIGOA-UHFFFAOYSA-N 0.000 claims description 7
• 150000001502 aryl halides Chemical class 0.000 claims description 6
• 230000004663 cell proliferation Effects 0.000 claims description 6
• ZKSYUNLBFSOENV-UHFFFAOYSA-N n-(2-hydroxyethyl)benzamide Chemical compound OCCNC(=O)C1=CC=CC=C1 ZKSYUNLBFSOENV-UHFFFAOYSA-N 0.000 claims description 6
• 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 description 6
• 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 description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• 230000010261 cell growth Effects 0.000 claims description 5
• 230000028709 inflammatory response Effects 0.000 claims description 5
• PPKGFSZXBXLTQX-UHFFFAOYSA-N n-(2-methylsulfonylethyl)benzamide Chemical compound CS(=O)(=O)CCNC(=O)C1=CC=CC=C1 PPKGFSZXBXLTQX-UHFFFAOYSA-N 0.000 claims description 5
• 230000024932 T cell mediated immunity Effects 0.000 claims description 4
• FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 claims description 4
• 230000001404 mediated effect Effects 0.000 claims description 4
• PCSOUTBWLVEYRU-UHFFFAOYSA-N n-(1-hydroxy-2-methylpropan-2-yl)benzamide Chemical compound OCC(C)(C)NC(=O)C1=CC=CC=C1 PCSOUTBWLVEYRU-UHFFFAOYSA-N 0.000 claims description 4
• MWDZXUOUTGAFAL-UHFFFAOYSA-N n-(2,2,2-trifluoroethyl)benzamide Chemical compound FC(F)(F)CNC(=O)C1=CC=CC=C1 MWDZXUOUTGAFAL-UHFFFAOYSA-N 0.000 claims description 4
• ZZKSAVUXOUDMGW-UHFFFAOYSA-N n-(2-methoxyethyl)benzamide Chemical compound COCCNC(=O)C1=CC=CC=C1 ZZKSAVUXOUDMGW-UHFFFAOYSA-N 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• BZRJXUYSGDHGBI-UHFFFAOYSA-N 2-(1-hydroxy-2-methylpropan-2-yl)-3-methoxybenzamide Chemical compound OCC(C)(C)C1=C(C(=O)N)C=CC=C1OC BZRJXUYSGDHGBI-UHFFFAOYSA-N 0.000 claims description 3
• INGRVKIBWHSBCS-UHFFFAOYSA-N 2-(2-hydroxyethyl)-3-methoxybenzamide Chemical compound OCCC1=C(C(=O)N)C=CC=C1OC INGRVKIBWHSBCS-UHFFFAOYSA-N 0.000 claims description 3
• 230000003833 cell viability Effects 0.000 claims description 3
• 239000001257 hydrogen Substances 0.000 claims description 3
• XFBPZMPTMINJJY-UHFFFAOYSA-N n-[2-(methylamino)ethyl]benzamide Chemical compound CNCCNC(=O)C1=CC=CC=C1 XFBPZMPTMINJJY-UHFFFAOYSA-N 0.000 claims description 3
• 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 2
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
• 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 description 2
• DACWQSNZECJJGG-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CN=C21 DACWQSNZECJJGG-UHFFFAOYSA-N 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• XFZNIUMLNKPJGO-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]benzamide Chemical compound C1=CC(C)=CC=C1CNC(=O)C1=CC=CC=C1 XFZNIUMLNKPJGO-UHFFFAOYSA-N 0.000 claims description 2
• 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
• OAVWTNQQFNPGQE-UHFFFAOYSA-N 2-(2-hydroxy-2-methylpropyl)-3-methoxybenzamide Chemical compound OC(CC1=C(C(=O)N)C=CC=C1OC)(C)C OAVWTNQQFNPGQE-UHFFFAOYSA-N 0.000 claims 2
• 229930012538 Paclitaxel Natural products 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
• RHGJKFDRWARLHZ-UHFFFAOYSA-N 2-(2-fluoroethyl)-3-methoxybenzamide Chemical compound FCCC1=C(C(=O)N)C=CC=C1OC RHGJKFDRWARLHZ-UHFFFAOYSA-N 0.000 claims 1
• HUPVBFQYJHFONM-UHFFFAOYSA-N 2-(4-fluorophenyl)acetamide Chemical compound NC(=O)CC1=CC=C(F)C=C1 HUPVBFQYJHFONM-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
• RAWZIQRCKUPYPE-UHFFFAOYSA-N 4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]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(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 RAWZIQRCKUPYPE-UHFFFAOYSA-N 0.000 claims 1
• LWWKPQWDEDXMPV-UHFFFAOYSA-N 4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]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(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 LWWKPQWDEDXMPV-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
• 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
• PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 claims 1
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-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
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-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
• 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
• 229940009456 adriamycin Drugs 0.000 claims 1
• 230000002280 anti-androgenic effect Effects 0.000 claims 1
• 239000000051 antiandrogen Substances 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
• 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
• 229960004397 cyclophosphamide Drugs 0.000 claims 1
• 229960000684 cytarabine Drugs 0.000 claims 1
• 229960000975 daunorubicin Drugs 0.000 claims 1
• STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims 1
• 229960003668 docetaxel Drugs 0.000 claims 1
• 229960004679 doxorubicin Drugs 0.000 claims 1
• 229930013356 epothilone Natural products 0.000 claims 1
• 150000003883 epothilone derivatives Chemical class 0.000 claims 1
• FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 claims 1
• 229960001842 estramustine Drugs 0.000 claims 1
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims 1
• 229960005420 etoposide Drugs 0.000 claims 1
• 229960000390 fludarabine Drugs 0.000 claims 1
• GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 claims 1
• 229960002949 fluorouracil Drugs 0.000 claims 1
• 229960000908 idarubicin Drugs 0.000 claims 1
• 229960001101 ifosfamide Drugs 0.000 claims 1
• HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims 1
• 229960001924 melphalan Drugs 0.000 claims 1
• SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims 1
• 229960000485 methotrexate Drugs 0.000 claims 1
• 229960001156 mitoxantrone Drugs 0.000 claims 1
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims 1
• ZSMTUVRQQASGAC-UHFFFAOYSA-N n-(2,2,2-trifluoroethyl)pyridine-2-carboxamide Chemical compound FC(F)(F)CNC(=O)C1=CC=CC=N1 ZSMTUVRQQASGAC-UHFFFAOYSA-N 0.000 claims 1
• JEPKRGPITPUMJF-UHFFFAOYSA-N n-(2,2-difluoroethyl)-4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCC(F)F)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 JEPKRGPITPUMJF-UHFFFAOYSA-N 0.000 claims 1
• YKJAIDYAGJECHO-UHFFFAOYSA-N n-(2-fluoroethyl)-4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCF)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 YKJAIDYAGJECHO-UHFFFAOYSA-N 0.000 claims 1
• SLDQAHBRDJMRBD-UHFFFAOYSA-N n-(2-fluoroethyl)benzamide Chemical compound FCCNC(=O)C1=CC=CC=C1 SLDQAHBRDJMRBD-UHFFFAOYSA-N 0.000 claims 1
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