JP2015511629A5 - - Google Patents
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- Publication number
- JP2015511629A5 JP2015511629A5 JP2015502481A JP2015502481A JP2015511629A5 JP 2015511629 A5 JP2015511629 A5 JP 2015511629A5 JP 2015502481 A JP2015502481 A JP 2015502481A JP 2015502481 A JP2015502481 A JP 2015502481A JP 2015511629 A5 JP2015511629 A5 JP 2015511629A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- pyridin
- ylmethyl
- triazolo
- 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 nitro, hydroxy Chemical group 0.000 claims 79
- 150000001875 compounds Chemical class 0.000 claims 35
- 229910052739 hydrogen Inorganic materials 0.000 claims 25
- 239000001257 hydrogen Substances 0.000 claims 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 229910052736 halogen Inorganic materials 0.000 claims 20
- 150000002367 halogens Chemical class 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 12
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 229920006395 saturated elastomer Polymers 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 150000001204 N-oxides Chemical class 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000000651 prodrug Substances 0.000 claims 6
- 229940002612 prodrug Drugs 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- DEBZZZPGFBEZBW-UHFFFAOYSA-N N-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1=CC=C2C(=N1)N(N=N2)CC=1C=C2C=CC=NC2=CC=1 DEBZZZPGFBEZBW-UHFFFAOYSA-N 0.000 claims 3
- 210000004027 cell Anatomy 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 2
- 201000008808 Fibrosarcoma Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- 108091000080 Phosphotransferase Proteins 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- 206010039491 Sarcoma Diseases 0.000 claims 2
- 208000021712 Soft tissue sarcoma Diseases 0.000 claims 2
- 239000000730 antalgic agent Substances 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 2
- 239000000739 antihistaminic agent Substances 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000003018 immunosuppressive agent Substances 0.000 claims 2
- 229940125721 immunosuppressive agent Drugs 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 102000020233 phosphotransferase Human genes 0.000 claims 2
- 229950010765 pivalate Drugs 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- QNUASQXVZJWQBW-UHFFFAOYSA-N 1-[3-(quinolin-6-ylmethyl)imidazo[4,5-b]pyridin-5-yl]ethanone Chemical compound N1=CC=CC2=CC(CN3C=NC4=CC=C(N=C43)C(=O)C)=CC=C21 QNUASQXVZJWQBW-UHFFFAOYSA-N 0.000 claims 1
- AXGSZRSRDMYBMK-UHFFFAOYSA-N 1-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]-n-methoxyethanimine;hydrochloride Chemical compound Cl.C1=CN=C2C=C(F)C(CN3N=NC4=CC=C(N=C43)C(C)=NOC)=CC2=C1 AXGSZRSRDMYBMK-UHFFFAOYSA-N 0.000 claims 1
- QYPDLRROIKAURY-UHFFFAOYSA-N 1-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]ethanone Chemical compound C1=CN=C2C=C(F)C(CN3N=NC4=CC=C(N=C43)C(=O)C)=CC2=C1 QYPDLRROIKAURY-UHFFFAOYSA-N 0.000 claims 1
- LXHNRPXNNMAFTI-UHFFFAOYSA-N 2,6-difluoro-4-[3-(quinolin-6-ylmethyl)imidazo[4,5-b]pyridin-5-yl]benzoic acid Chemical compound C1=C(F)C(C(=O)O)=C(F)C=C1C1=CC=C(N=CN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 LXHNRPXNNMAFTI-UHFFFAOYSA-N 0.000 claims 1
- PIKJMYAHJUMBAC-UHFFFAOYSA-N 2,6-difluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(F)C(C(=O)N)=C(F)C=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 PIKJMYAHJUMBAC-UHFFFAOYSA-N 0.000 claims 1
- JCISGNLLEVOIIT-UHFFFAOYSA-N 2-[1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]ethylideneamino]oxyethylurea Chemical compound N1=CC=CC2=CC(CN3N=NC4=CC=C(N=C43)C(=NOCCNC(N)=O)C)=CC=C21 JCISGNLLEVOIIT-UHFFFAOYSA-N 0.000 claims 1
- GJQFPKFKHPOFJB-UHFFFAOYSA-N 2-[1-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]ethylideneamino]oxyethanol Chemical compound C1=CN=C2C=C(F)C(CN3N=NC4=CC=C(N=C43)C(=NOCCO)C)=CC2=C1 GJQFPKFKHPOFJB-UHFFFAOYSA-N 0.000 claims 1
- ZVLAVSMGJAYDHL-UHFFFAOYSA-N 2-[1-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]ethylideneamino]oxyethanol;hydrochloride Chemical compound Cl.C1=CN=C2C=C(F)C(CN3N=NC4=CC=C(N=C43)C(=NOCCO)C)=CC2=C1 ZVLAVSMGJAYDHL-UHFFFAOYSA-N 0.000 claims 1
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims 1
- JBLIPQDYRNUBON-UHFFFAOYSA-N 2-chloro-4-[3-(quinolin-6-ylmethyl)imidazo[4,5-b]pyridin-5-yl]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC=C1C1=CC=C(N=CN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 JBLIPQDYRNUBON-UHFFFAOYSA-N 0.000 claims 1
- REQQUNOUUNUVSW-UHFFFAOYSA-N 2-chloro-4-[3-[(7-fluoro-1-oxidoquinolin-1-ium-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(Cl)C(C(=O)N)=CC=C1C1=CC=C(N=NN2CC=3C(=CC4=[N+]([O-])C=CC=C4C=3)F)C2=N1 REQQUNOUUNUVSW-UHFFFAOYSA-N 0.000 claims 1
- IEIJPGCZDVVTGF-UHFFFAOYSA-N 2-chloro-n-(2-hydroxy-2-methylpropoxy)-4-[3-(quinolin-6-ylmethyl)imidazo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(Cl)C(C(=O)NOCC(C)(O)C)=CC=C1C1=CC=C(N=CN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 IEIJPGCZDVVTGF-UHFFFAOYSA-N 0.000 claims 1
- BRSYEFMPOGCMCI-UHFFFAOYSA-N 2-chloro-n-(2-hydroxyethoxy)-4-[3-(quinolin-6-ylmethyl)imidazo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(Cl)C(C(=O)NOCCO)=CC=C1C1=CC=C(N=CN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 BRSYEFMPOGCMCI-UHFFFAOYSA-N 0.000 claims 1
- 125000000981 3-amino-3-oxopropyl group Chemical group [H]C([*])([H])C([H])([H])C(=O)N([H])[H] 0.000 claims 1
- LZYCSJFSOVZBKW-UHFFFAOYSA-N 4-[3-(1,3-benzothiazol-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]-2,6-difluorobenzamide Chemical compound C1=C(F)C(C(=O)N)=C(F)C=C1C1=CC=C(N=NN2CC=3C=C4SC=NC4=CC=3)C2=N1 LZYCSJFSOVZBKW-UHFFFAOYSA-N 0.000 claims 1
- HMHGGOLCAGMLOF-UHFFFAOYSA-N 4-[3-(quinolin-6-ylmethyl)imidazo[4,5-b]pyridin-5-yl]-2-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C(=O)N)=CC=C1C1=CC=C(N=CN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 HMHGGOLCAGMLOF-UHFFFAOYSA-N 0.000 claims 1
- NAQNOOPPCTUYMT-UHFFFAOYSA-N 4-[3-[(5,7-difluoroquinolin-6-yl)methyl]imidazo[4,5-b]pyridin-5-yl]-2-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C(=O)N)=CC=C1C1=CC=C(N=CN2CC=3C(=C4C=CC=NC4=CC=3F)F)C2=N1 NAQNOOPPCTUYMT-UHFFFAOYSA-N 0.000 claims 1
- TVGRZVKKRUTZCU-UHFFFAOYSA-N 4-[3-[(5,7-difluoroquinolin-6-yl)methyl]imidazo[4,5-b]pyridin-5-yl]-2-methylbenzamide Chemical compound C1=C(C(N)=O)C(C)=CC(C=2N=C3N(CC=4C(=C5C=CC=NC5=CC=4F)F)C=NC3=CC=2)=C1 TVGRZVKKRUTZCU-UHFFFAOYSA-N 0.000 claims 1
- GVTGBYYHUJVDCQ-UHFFFAOYSA-N 4-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[4,5-b]pyridin-5-yl]-2-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C(=O)N)=CC=C1C1=CC=C(N=CN2CC=3C(=CC4=NC=CC=C4C=3)F)C2=N1 GVTGBYYHUJVDCQ-UHFFFAOYSA-N 0.000 claims 1
- QJCRAKNGMUECSE-UHFFFAOYSA-N 4-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[4,5-b]pyridin-5-yl]-2-methylbenzamide Chemical compound C1=C(C(N)=O)C(C)=CC(C=2N=C3N(CC=4C(=CC5=NC=CC=C5C=4)F)C=NC3=CC=2)=C1 QJCRAKNGMUECSE-UHFFFAOYSA-N 0.000 claims 1
- JMIUGOGTLNHALB-UHFFFAOYSA-N 4-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[4,5-b]pyridin-5-yl]-2-methylbenzamide;hydrochloride Chemical compound Cl.C1=C(C(N)=O)C(C)=CC(C=2N=C3N(CC=4C(=CC5=NC=CC=C5C=4)F)C=NC3=CC=2)=C1 JMIUGOGTLNHALB-UHFFFAOYSA-N 0.000 claims 1
- ZDERFVZBKMRCQG-UHFFFAOYSA-N 4-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]-n-(2-hydroxyethoxy)-2-methylbenzamide Chemical compound C1=C(C(=O)NOCCO)C(C)=CC(C=2N=C3N(CC=4C(=CC5=NC=CC=C5C=4)F)N=NC3=CC=2)=C1 ZDERFVZBKMRCQG-UHFFFAOYSA-N 0.000 claims 1
- FYSMQMYUXKAKKJ-UHFFFAOYSA-N 4-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]-n-(2-hydroxyethoxy)-2-methylbenzamide;hydrochloride Chemical compound Cl.C1=C(C(=O)NOCCO)C(C)=CC(C=2N=C3N(CC=4C(=CC5=NC=CC=C5C=4)F)N=NC3=CC=2)=C1 FYSMQMYUXKAKKJ-UHFFFAOYSA-N 0.000 claims 1
- GHFMBHGMYUMPCY-UHFFFAOYSA-N 5-[3-(quinolin-6-ylmethyl)imidazo[4,5-b]pyridin-5-yl]-2,3-dihydroisoindol-1-one Chemical compound N1=CC=CC2=CC(CN3C=NC4=CC=C(N=C43)C=3C=C4CNC(C4=CC=3)=O)=CC=C21 GHFMBHGMYUMPCY-UHFFFAOYSA-N 0.000 claims 1
- WTMZIJSENRMDDW-UHFFFAOYSA-N 5-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]-2,3-dihydroisoindol-1-one Chemical compound N1=CC=CC2=CC(CN3N=NC4=CC=C(N=C43)C=3C=C4CNC(C4=CC=3)=O)=CC=C21 WTMZIJSENRMDDW-UHFFFAOYSA-N 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 208000003950 B-cell lymphoma Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 206010004593 Bile duct cancer Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000011691 Burkitt lymphomas Diseases 0.000 claims 1
- XYKMCOLDHRKURL-UHFFFAOYSA-N C(C)C1=C(OC=C1)C(=O)ONCC1=C(C=C(C=C1)C1=CC=C2C(=N1)N(N=N2)CC=2C=C1C=CC=NC1=CC2)C Chemical class C(C)C1=C(OC=C1)C(=O)ONCC1=C(C=C(C=C1)C1=CC=C2C(=N1)N(N=N2)CC=2C=C1C=CC=NC1=CC2)C XYKMCOLDHRKURL-UHFFFAOYSA-N 0.000 claims 1
- YXDKAAQMVCOEOL-UHFFFAOYSA-N CC(=NO)c1ccc2nnn(Cc3cc4cccnc4cc3F)c2n1 Chemical compound CC(=NO)c1ccc2nnn(Cc3cc4cccnc4cc3F)c2n1 YXDKAAQMVCOEOL-UHFFFAOYSA-N 0.000 claims 1
- FAGBNADIPVHBRY-UHFFFAOYSA-N CC(=NOCCN)c1ccc2nnn(Cc3ccc4ncccc4c3)c2n1 Chemical compound CC(=NOCCN)c1ccc2nnn(Cc3ccc4ncccc4c3)c2n1 FAGBNADIPVHBRY-UHFFFAOYSA-N 0.000 claims 1
- AJBJSTRLWOVZTN-UHFFFAOYSA-N CC(=NOCCO)c1ccc2nnn(Cc3ccc4ncccc4c3)c2n1 Chemical compound CC(=NOCCO)c1ccc2nnn(Cc3ccc4ncccc4c3)c2n1 AJBJSTRLWOVZTN-UHFFFAOYSA-N 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 208000004463 Follicular Adenocarcinoma Diseases 0.000 claims 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 206010018852 Haematoma Diseases 0.000 claims 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 1
- 206010073069 Hepatic cancer Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 208000018142 Leiomyosarcoma Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000006644 Malignant Fibrous Histiocytoma Diseases 0.000 claims 1
- 206010027406 Mesothelioma Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- VRIWGOIUDMSOLM-UHFFFAOYSA-N N-[1-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]ethylidene]hydroxylamine hydrochloride Chemical compound Cl.CC(=NO)c1ccc2nnn(Cc3cc4cccnc4cc3F)c2n1 VRIWGOIUDMSOLM-UHFFFAOYSA-N 0.000 claims 1
- HVBCPZGKXVKFNC-UHFFFAOYSA-N N-hydroxy-2-methyl-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound Cc1cc(ccc1C(=O)NO)-c1ccc2nnn(Cc3ccc4ncccc4c3)c2n1 HVBCPZGKXVKFNC-UHFFFAOYSA-N 0.000 claims 1
- ZXOWVMPQHDOBOU-UHFFFAOYSA-N N1=CC=CC2=CC(=CC=C12)CN1C=NC=2C1=NC(=CC2)C(C)=NNC(=O)N Chemical compound N1=CC=CC2=CC(=CC=C12)CN1C=NC=2C1=NC(=CC2)C(C)=NNC(=O)N ZXOWVMPQHDOBOU-UHFFFAOYSA-N 0.000 claims 1
- XIIGIIPVKKHOCP-UHFFFAOYSA-N NC(=O)c1c(F)cc(cc1F)-c1ccc2nnn(Cc3ccc4[n+]([O-])cccc4c3)c2n1 Chemical compound NC(=O)c1c(F)cc(cc1F)-c1ccc2nnn(Cc3ccc4[n+]([O-])cccc4c3)c2n1 XIIGIIPVKKHOCP-UHFFFAOYSA-N 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
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- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 201000010208 Seminoma Diseases 0.000 claims 1
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- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 208000015778 Undifferentiated pleomorphic sarcoma Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 208000008383 Wilms tumor Diseases 0.000 claims 1
- 201000006083 Xeroderma Pigmentosum Diseases 0.000 claims 1
- KMBSLDHUDPDCBQ-UHFFFAOYSA-N [1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]ethylideneamino]urea Chemical compound N1=CC=CC2=CC(CN3N=NC4=CC=C(N=C43)C(=NNC(N)=O)C)=CC=C21 KMBSLDHUDPDCBQ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- LEHOGBUBQSGCOK-UHFFFAOYSA-N aminothiourea;hydron;chloride Chemical compound Cl.NNC(N)=S LEHOGBUBQSGCOK-UHFFFAOYSA-N 0.000 claims 1
- 229940035676 analgesics Drugs 0.000 claims 1
- 230000001387 anti-histamine Effects 0.000 claims 1
- 229940125715 antihistaminic agent Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 210000001130 astrocyte Anatomy 0.000 claims 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 1
- 208000026900 bile duct neoplasm Diseases 0.000 claims 1
- 201000001531 bladder carcinoma Diseases 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 201000008275 breast carcinoma Diseases 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 208000006990 cholangiocarcinoma Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
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| KR20140144726A (ko) * | 2012-03-30 | 2014-12-19 | 리젠 파마슈티컬스 소시에떼 아노님 | C-met 단백질 키나제의 조절제로서의 신규한 3,5-디치환-3h-이미다조[4,5-b]피리딘 및 3,5- 디치환 -3h-[1,2,3]트리아졸로[4,5-b] 피리딘 화합물 |
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| EP3125920B1 (en) | 2014-04-04 | 2020-12-23 | Del Mar Pharmaceuticals | Dianhydrogalactitol, diacetyldianhydrogalactitol or dibromodulcitol to treat non-small-cell carcinoma of the lung and ovarian cancer |
| RU2748884C2 (ru) * | 2015-07-20 | 2021-06-01 | Джензим Корпорейшн | Ингибиторы рецептора колониестимулирующего фактора-1 (csf-1r) |
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| CN114031562A (zh) * | 2021-10-31 | 2022-02-11 | 南京碳硅人工智能生物医药技术研究院有限公司 | 一种具有抗肿瘤的吡啶衍生物的工艺优化 |
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| ES2616255T3 (es) * | 2008-04-30 | 2017-06-12 | National Health Research Institutes | Compuestos de pirimidina bicíclicos condensados como inhibidores de las aurora cinasas |
| CN102127096A (zh) | 2009-12-31 | 2011-07-20 | 和记黄埔医药（上海）有限公司 | 三氮唑并吡啶和三氮唑并吡嗪化合物及其组合物和应用 |
| PL2719699T3 (pl) * | 2009-12-31 | 2016-01-29 | Hutchison Medipharma Ltd | Pewne triazolopirazyny, ich kompozycje i sposoby ich stosowania |
| EP2571878B1 (en) | 2010-05-17 | 2018-10-17 | Incozen Therapeutics Pvt. Ltd. | Novel 3,5-disubstitued-3h-imidazo[4,5-b]pyridine and 3,5- disubstitued -3h-[1,2,3]triazolo[4,5-b]pyridine compounds as modulators of protein kinases |
| KR20140144726A (ko) * | 2012-03-30 | 2014-12-19 | 리젠 파마슈티컬스 소시에떼 아노님 | C-met 단백질 키나제의 조절제로서의 신규한 3,5-디치환-3h-이미다조[4,5-b]피리딘 및 3,5- 디치환 -3h-[1,2,3]트리아졸로[4,5-b] 피리딘 화합물 |
| US9887269B2 (en) * | 2015-11-30 | 2018-02-06 | Taiwan Semiconductor Manufacturing Company, Ltd. | Multi-gate device and method of fabrication thereof |
-
2013
- 2013-02-27 KR KR1020147030532A patent/KR20140144726A/ko not_active Ceased
- 2013-02-27 NZ NZ629499A patent/NZ629499A/en not_active IP Right Cessation
- 2013-02-27 BR BR112014024251A patent/BR112014024251A8/pt not_active IP Right Cessation
- 2013-02-27 EP EP13716061.0A patent/EP2831073B1/en not_active Not-in-force
- 2013-02-27 CA CA2865719A patent/CA2865719C/en active Active
- 2013-02-27 WO PCT/IB2013/051577 patent/WO2013144737A2/en not_active Ceased
- 2013-02-27 AP AP2014007966A patent/AP3908A/en active
- 2013-02-27 EA EA201491520A patent/EA026412B1/ru unknown
- 2013-02-27 CN CN201710062943.0A patent/CN107082779A/zh active Pending
- 2013-02-27 ES ES13716061T patent/ES2856848T3/es active Active
- 2013-02-27 MX MX2014011750A patent/MX359888B/es active IP Right Grant
- 2013-02-27 KR KR1020207002779A patent/KR102164317B1/ko not_active Expired - Fee Related
- 2013-02-27 MY MYPI2014002712A patent/MY169268A/en unknown
- 2013-02-27 CN CN201380022471.6A patent/CN104321322A/zh active Pending
- 2013-02-27 SG SG11201406185WA patent/SG11201406185WA/en unknown
- 2013-02-27 US US14/389,336 patent/US9815831B2/en not_active Expired - Fee Related
- 2013-02-27 AU AU2013239398A patent/AU2013239398B2/en not_active Ceased
- 2013-02-27 JP JP2015502481A patent/JP6192708B2/ja not_active Expired - Fee Related
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2014
- 2014-09-07 IL IL234513A patent/IL234513B/en active IP Right Grant
- 2014-09-26 PH PH12014502166A patent/PH12014502166B1/en unknown
- 2014-09-29 CL CL2014002604A patent/CL2014002604A1/es unknown
- 2014-10-28 CO CO14238774A patent/CO7111276A2/es unknown
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2017
- 2017-09-14 US US15/705,005 patent/US11066402B2/en not_active Expired - Fee Related
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2021
- 2021-05-30 US US17/303,494 patent/US20210371416A1/en not_active Abandoned
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