ES2539265T3 - Triazolopiridinas - Google Patents
Triazolopiridinas Download PDFInfo
- Publication number
- ES2539265T3 ES2539265T3 ES12721779.2T ES12721779T ES2539265T3 ES 2539265 T3 ES2539265 T3 ES 2539265T3 ES 12721779 T ES12721779 T ES 12721779T ES 2539265 T3 ES2539265 T3 ES 2539265T3
- Authority
- ES
- Spain
- Prior art keywords
- amino
- phenyl
- triazolo
- pyridin
- 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.)
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- 150000008523 triazolopyridines Chemical class 0.000 title description 9
- -1 hydroxy- Chemical class 0.000 claims abstract description 450
- 150000001875 compounds Chemical class 0.000 claims abstract description 369
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 155
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 114
- 125000001424 substituent group Chemical group 0.000 claims abstract description 88
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 86
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 76
- 125000001475 halogen functional group Chemical group 0.000 claims abstract description 25
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 24
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 327
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 105
- 125000005843 halogen group Chemical group 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 81
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 57
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
- 238000002360 preparation method Methods 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 21
- 238000005859 coupling reaction Methods 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 18
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 16
- 206010028980 Neoplasm Diseases 0.000 claims description 15
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 210000004027 cell Anatomy 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 12
- 150000001204 N-oxides Chemical class 0.000 claims description 12
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 11
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 230000001413 cellular effect Effects 0.000 claims description 9
- 230000028709 inflammatory response Effects 0.000 claims description 9
- 230000004083 survival effect Effects 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 230000004663 cell proliferation Effects 0.000 claims description 8
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 7
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 230000010261 cell growth Effects 0.000 claims description 7
- 238000011321 prophylaxis Methods 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 6
- 206010027476 Metastases Diseases 0.000 claims description 6
- 150000001502 aryl halides Chemical class 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 5
- 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 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 208000032839 leukemia Diseases 0.000 claims description 4
- 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 3
- 208000002699 Digestive System Neoplasms Diseases 0.000 claims description 3
- 208000009849 Female Genital Neoplasms Diseases 0.000 claims description 3
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
- 206010025323 Lymphomas Diseases 0.000 claims description 3
- 206010059282 Metastases to central nervous system Diseases 0.000 claims description 3
- 206010027540 Microcytosis Diseases 0.000 claims description 3
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 3
- 206010029098 Neoplasm skin Diseases 0.000 claims description 3
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 3
- 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 3
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 3
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
- 201000004477 skin sarcoma Diseases 0.000 claims description 3
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 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
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- UKSPLGSWFMNOJA-UHFFFAOYSA-N 4-[[6-[4-(cyclopropylmethylcarbamoyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-ethoxy-n-ethylbenzamide Chemical compound CCOC1=CC(C(=O)NCC)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC3CC3)C=CC2=N1 UKSPLGSWFMNOJA-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 201000011523 endocrine gland cancer Diseases 0.000 claims description 2
- 201000005787 hematologic cancer Diseases 0.000 claims description 2
- 208000037841 lung tumor Diseases 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- NNBCIPJVCURQSG-UHFFFAOYSA-N n,n-diethyl-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)N(CC)CC)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 NNBCIPJVCURQSG-UHFFFAOYSA-N 0.000 claims description 2
- OGZWDYBCANGCKI-UHFFFAOYSA-N n,n-diethyl-4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-propan-2-yloxybenzamide Chemical compound CC(C)OC1=CC(C(=O)N(CC)CC)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 OGZWDYBCANGCKI-UHFFFAOYSA-N 0.000 claims description 2
- KDUJDDIIABWPJU-UHFFFAOYSA-N n,n-diethyl-4-[[6-[4-[[2-(4-fluorophenyl)acetyl]amino]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-propoxybenzamide Chemical compound CCCOC1=CC(C(=O)N(CC)CC)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 KDUJDDIIABWPJU-UHFFFAOYSA-N 0.000 claims description 2
- IDLKRRWMQMXVHB-UHFFFAOYSA-N n-[2-[acetyl(methyl)amino]ethyl]-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)N(C)CCN(C)C(C)=O)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 IDLKRRWMQMXVHB-UHFFFAOYSA-N 0.000 claims description 2
- NDSMYLTUQAZUAG-UHFFFAOYSA-N n-ethyl-4-[[6-[4-[(3-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCC)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=C(F)C=CC=3)C=CC2=N1 NDSMYLTUQAZUAG-UHFFFAOYSA-N 0.000 claims description 2
- RUZMXDZMCXRBMT-UHFFFAOYSA-N n-ethyl-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(=O)NCC)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 RUZMXDZMCXRBMT-UHFFFAOYSA-N 0.000 claims description 2
- YSLZWBMXMOCFMB-UHFFFAOYSA-N n-ethyl-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)N(C)CC)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 YSLZWBMXMOCFMB-UHFFFAOYSA-N 0.000 claims description 2
- AEFBRPDPEQJHGY-UHFFFAOYSA-N n-ethyl-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)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 AEFBRPDPEQJHGY-UHFFFAOYSA-N 0.000 claims description 2
- RYMDBAHJXXKSEK-UHFFFAOYSA-N n-tert-butyl-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)NC(C)(C)C)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 RYMDBAHJXXKSEK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
- 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
- 230000006450 immune cell response Effects 0.000 claims 4
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 3
- 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
- 206010006187 Breast cancer Diseases 0.000 claims 2
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- 230000035755 proliferation Effects 0.000 claims 2
- 208000023958 prostate neoplasm Diseases 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
- 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
- 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
- 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
- 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
- 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
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 1
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- 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
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 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
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- MHNHYTDAOYJUEZ-UHFFFAOYSA-N triphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MHNHYTDAOYJUEZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
- 229910052722 tritium Inorganic materials 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
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11163342 | 2011-04-21 | ||
| EP11163342 | 2011-04-21 | ||
| EP11167872 | 2011-05-27 | ||
| EP11167872 | 2011-05-27 | ||
| PCT/EP2012/056914 WO2012143329A1 (en) | 2011-04-21 | 2012-04-16 | Triazolopyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2539265T3 true ES2539265T3 (es) | 2015-06-29 |
Family
ID=46124297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12721779.2T Active ES2539265T3 (es) | 2011-04-21 | 2012-04-16 | Triazolopiridinas |
Country Status (39)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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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 |
| CA2662074A1 (en) * | 2006-08-30 | 2008-03-06 | Cellzome Limited | Triazole derivatives as kinase inhibitors |
| 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 |
| EP2343297A1 (en) * | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridines |
| UY33452A (es) * | 2010-06-16 | 2012-01-31 | Bayer Schering Pharma Ag | Triazolopiridinas sustituidas |
-
2012
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- 2012-04-16 MX MX2013012289A patent/MX348783B/es active IP Right Grant
- 2012-04-16 JP JP2014505584A patent/JP5989091B2/ja not_active Expired - Fee Related
- 2012-04-16 AP AP2013007182A patent/AP3491A/xx active
- 2012-04-16 SG SG2013073044A patent/SG194003A1/en unknown
- 2012-04-16 SI SI201230220T patent/SI2699575T1/sl unknown
- 2012-04-16 PL PL12721779T patent/PL2699575T3/pl unknown
- 2012-04-16 MA MA36344A patent/MA35049B1/fr unknown
- 2012-04-16 CA CA2833657A patent/CA2833657A1/en not_active Abandoned
- 2012-04-16 ME MEP-2015-80A patent/ME02143B/me unknown
- 2012-04-16 RS RS20150345A patent/RS54044B1/sr unknown
- 2012-04-16 PT PT127217792T patent/PT2699575E/pt unknown
- 2012-04-16 US US14/113,017 patent/US20140120087A1/en not_active Abandoned
- 2012-04-16 EP EP12721779.2A patent/EP2699575B1/en active Active
- 2012-04-16 HU HUE12721779A patent/HUE025496T2/en unknown
- 2012-04-16 PH PH1/2013/502169A patent/PH12013502169A1/en unknown
- 2012-04-16 AU AU2012244859A patent/AU2012244859B2/en not_active Ceased
- 2012-04-16 HR HRP20150517TT patent/HRP20150517T1/hr unknown
- 2012-04-16 MY MYPI2013701964A patent/MY164939A/en unknown
- 2012-04-16 PE PE2013002378A patent/PE20141351A1/es not_active Application Discontinuation
- 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
- 2012-04-18 SA SA112330466A patent/SA112330466B1/ar unknown
- 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
- 2012-04-20 AR ARP120101355A patent/AR086191A1/es unknown
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2013
- 2013-10-03 IL IL228704A patent/IL228704A0/en unknown
- 2013-10-18 GT GT201300254A patent/GT201300254A/es unknown
- 2013-10-21 CL CL2013003044A patent/CL2013003044A1/es unknown
- 2013-10-21 CR CR20130539A patent/CR20130539A/es unknown
- 2013-10-21 DO DO2013000244A patent/DOP2013000244A/es unknown
- 2013-10-21 CO CO13248763A patent/CO6801751A2/es active IP Right Grant
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