EA023766B1 - Триазолопиридины - Google Patents
Триазолопиридины Download PDFInfo
- 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
Links
- 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
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- 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
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- 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
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- 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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- 239000000758 substrate Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- HNUHNECIEYXPJH-UHFFFAOYSA-N tert-butyl n-[4-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C1=CN2N=C(N)N=C2C=C1 HNUHNECIEYXPJH-UHFFFAOYSA-N 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11163342 | 2011-04-21 | ||
| EP11167872 | 2011-05-27 | ||
| PCT/EP2012/056914 WO2012143329A1 (en) | 2011-04-21 | 2012-04-16 | Triazolopyridines |
Publications (2)
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| EA201301181A1 EA201301181A1 (ru) | 2014-08-29 |
| EA023766B1 true EA023766B1 (ru) | 2016-07-29 |
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| EA201301181A EA023766B1 (ru) | 2011-04-21 | 2012-04-16 | Триазолопиридины |
Country Status (39)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2012145728A1 (en) | 2011-04-21 | 2012-10-26 | Gilead Sciences, Inc. | Benzothiazole compounds and their pharmaceutical use |
| UA112096C2 (uk) * | 2011-12-12 | 2016-07-25 | Байєр Інтеллектуал Проперті Гмбх | Заміщені триазолопіридини та їх застосування як інгібіторів ttk |
| WO2013103738A1 (en) | 2012-01-04 | 2013-07-11 | Gilead Sciences, Inc. | Napthalene acetic acid derivatives against hiv infection |
| WO2013103724A1 (en) | 2012-01-04 | 2013-07-11 | Gilead Sciences, Inc. | 2- (tert - butoxy) -2- (7 -methylquinolin- 6 - yl) acetic acid derivatives for treating aids |
| US9512126B2 (en) | 2012-03-14 | 2016-12-06 | Bayer Intellectual Property Gmbh | Substituted imidazopyridazines |
| EP2872506A1 (en) * | 2012-07-10 | 2015-05-20 | Bayer Pharma Aktiengesellschaft | Method for preparing substituted triazolopyridines |
| WO2014020043A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| WO2014020041A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| JP2016520634A (ja) * | 2013-06-07 | 2016-07-14 | バイエル・ファルマ・アクティエンゲゼルシャフト | 置換トリアゾロピリジン |
| WO2014195276A1 (en) * | 2013-06-07 | 2014-12-11 | Bayer Pharma Aktiengesellschaft | Substituted triazolopyridines having activity as mps-1 inhibitors |
| CN105246891A (zh) * | 2013-06-10 | 2016-01-13 | 拜耳制药股份公司 | 用于治疗癌症的新化合物 |
| EA201600003A1 (ru) * | 2013-06-11 | 2016-06-30 | Байер Фарма Акциенгезельшафт | КОМБИНАЦИИ ДЛЯ ЛЕЧЕНИЯ РАКА, СОДЕРЖАЩИЕ ИНГИБИТОР Mps-1 КИНАЗЫ И ИНГИБИТОР МИТОЗА |
| PT3008062T (pt) * | 2013-06-11 | 2017-06-07 | Bayer Pharma AG | Derivados de profármaco de triazolopiridinas substituídas |
| EP2860177A3 (en) | 2013-09-20 | 2015-06-10 | Bayer Intellectual Property GmbH | Synthesis of functionalized arenes |
| CA2981844A1 (en) | 2015-04-17 | 2016-10-20 | Netherlands Translational Research Center B.V. | Prognostic biomarkers for ttk inhibitor chemotherapy |
| CN109963854B (zh) * | 2017-03-16 | 2022-04-12 | 江苏恒瑞医药股份有限公司 | 杂芳基并[4,3-c]嘧啶-5-胺类衍生物、其制备方法及其在医药上的应用 |
| EP3956330A4 (en) | 2019-04-18 | 2023-01-18 | The Johns Hopkins University | SUBSTITUTED 2-AMINO-PYRAZOLYL-[1,2,4]TRIAZOLO[1,5A]PYRIDINE DERIVATIVES AND THEIR USE |
| US11529350B2 (en) | 2019-07-03 | 2022-12-20 | Sumitomo Pharma Oncology, Inc. | Tyrosine kinase non-receptor 1 (TNK1) inhibitors and uses thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008025821A1 (en) * | 2006-08-30 | 2008-03-06 | Cellzome Limited | Triazole derivatives as kinase inhibitors |
| WO2011063908A1 (en) * | 2009-11-30 | 2011-06-03 | Bayer Schering Pharma Aktiengesellschaft | Triazolopyridines |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US5011472A (en) | 1988-09-06 | 1991-04-30 | Brown University Research Foundation | Implantable delivery system for biological factors |
| DE602005010876D1 (de) | 2004-08-17 | 2008-12-18 | Galderma Res & Dev | Neuartige biaromatische ppar-rezeptoren aktivierende zusammensetzungen und ihre verwendung in kosmetischen oder pharmazeutischen zusammensetzungen |
| AR067562A1 (es) * | 2007-07-18 | 2009-10-14 | Novartis Ag | Compuestos heterociclicos inhibidores de kinasa |
| WO2009024824A1 (en) | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | 2-anilinopurin-8-ones as inhibitors of ttk/mps1 for the treatment of proliferative disorders |
| AU2008291075A1 (en) * | 2007-08-31 | 2009-03-05 | Merck Serono S.A. | Triazolopyridine compounds and their use as ask inhibitors |
| GB0719803D0 (en) | 2007-10-10 | 2007-11-21 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| EA201000797A1 (ru) * | 2007-11-27 | 2011-02-28 | Целльзом Лимитид | Аминотриазолы в качестве ингибиторов pi3k |
| JP2012517971A (ja) * | 2009-02-13 | 2012-08-09 | フォーヴィア・ファーマシューティカルズ | キナーゼ阻害薬としての［１，２，４］トリアゾロ［１，５−ａ］ピリジン類 |
| CA2760077A1 (en) | 2009-04-29 | 2010-11-04 | Marcus Koppitz | Substituted imidazoquinoxalines |
| CN102596932A (zh) | 2009-09-04 | 2012-07-18 | 拜耳医药股份有限公司 | 作为酪氨酸苏氨酸激酶抑制剂的取代氨基喹喔啉 |
| UY33452A (es) * | 2010-06-16 | 2012-01-31 | Bayer Schering Pharma Ag | Triazolopiridinas sustituidas |
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- 2012-04-16 US US14/113,017 patent/US20140120087A1/en not_active Abandoned
- 2012-04-16 EP EP12721779.2A patent/EP2699575B1/en active Active
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- 2012-04-16 AU AU2012244859A patent/AU2012244859B2/en not_active Ceased
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- 2012-04-16 WO PCT/EP2012/056914 patent/WO2012143329A1/en not_active Ceased
- 2012-04-16 ES ES12721779.2T patent/ES2539265T3/es active Active
- 2012-04-16 KR KR1020137030546A patent/KR20140025470A/ko not_active Ceased
- 2012-04-16 EA EA201301181A patent/EA023766B1/ru not_active IP Right Cessation
- 2012-04-16 DK DK12721779.2T patent/DK2699575T3/da active
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- 2012-04-18 JO JOP/2012/0093A patent/JO3040B1/ar active
- 2012-04-20 TW TW101114259A patent/TWI558703B/zh not_active IP Right Cessation
- 2012-04-20 UY UY0001034034A patent/UY34034A/es not_active Application Discontinuation
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2013
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008025821A1 (en) * | 2006-08-30 | 2008-03-06 | Cellzome Limited | Triazole derivatives as kinase inhibitors |
| WO2011063908A1 (en) * | 2009-11-30 | 2011-06-03 | Bayer Schering Pharma Aktiengesellschaft | Triazolopyridines |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
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