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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- QEZKMMVSLTZOJP-UHFFFAOYSA-M sodium [2,6-difluoro-4-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]benzoyl]-(2-hydroxyethoxy)azanide Chemical compound [Na+].OCCO[N-]C(=O)c1c(F)cc(cc1F)-c1ccc2nnn(Cc3cc4cccnc4cc3F)c2n1 QEZKMMVSLTZOJP-UHFFFAOYSA-M 0.000 claims 1
- QQWVSVSAOUICGI-UHFFFAOYSA-M sodium [2-chloro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzoyl]-(2-hydroxyethoxy)azanide Chemical compound [Na+].OCCO[N-]C(=O)c1ccc(cc1Cl)-c1ccc2nnn(Cc3ccc4ncccc4c3)c2n1 QQWVSVSAOUICGI-UHFFFAOYSA-M 0.000 claims 1
- QSVSMLSZVBDQPS-UHFFFAOYSA-M sodium [2-chloro-4-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]benzoyl]-(2-hydroxyethoxy)azanide Chemical compound [Na+].OCCO[N-]C(=O)c1ccc(cc1Cl)-c1ccc2nnn(Cc3cc4cccnc4cc3F)c2n1 QSVSMLSZVBDQPS-UHFFFAOYSA-M 0.000 claims 1
- WCZQGNLQIYMETI-UHFFFAOYSA-M sodium [4-[3-(1,3-benzothiazol-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]-2,6-difluorobenzoyl]-(2-hydroxyethoxy)azanide Chemical compound [Na+].OCCO[N-]C(=O)c1c(F)cc(cc1F)-c1ccc2nnn(Cc3ccc4ncsc4c3)c2n1 WCZQGNLQIYMETI-UHFFFAOYSA-M 0.000 claims 1
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Families Citing this family (17)
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| EP2831073B1 (en) * | 2012-03-30 | 2020-12-09 | Rhizen Pharmaceuticals S.A. | 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 c-met protein kinases |
| GB201321741D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| KR102359214B1 (ko) | 2014-04-04 | 2022-02-07 | 델 마 파마슈티컬스 | 폐의 비소세포 암종 및 난소암을 치료하기 위한 디안하이드로갈락티톨 및 이의 유사체 또는 유도체 |
| AR105392A1 (es) | 2015-07-20 | 2017-09-27 | Genzyme Corp | Inhibidores del receptor del factor estimulador de colonias 1 (csf-1r) |
| CN107573340B (zh) * | 2017-10-23 | 2020-11-24 | 江西科技师范大学 | 2-氨甲酰基-4-芳杂吡啶类化合物的制备及应用 |
| GB201803892D0 (en) | 2018-03-12 | 2018-04-25 | Ultrahuman Six Ltd | C-met binding agents |
| WO2020097396A1 (en) | 2018-11-07 | 2020-05-14 | Dana-Farber Cancer Institute, Inc. | Benzimidazole derivatives and aza-benzimidazole derivatives as janus kinase 2 inhibitors and uses thereof |
| WO2020097398A1 (en) | 2018-11-07 | 2020-05-14 | Dana-Farber Cancer Institute, Inc. | Benzothiazole derivatives and 7-aza-benzothiazole derivatives as janus kinase 2 inhibitors and uses thereof |
| EP3877371A4 (en) | 2018-11-07 | 2022-07-27 | Dana-Farber Cancer Institute, Inc. | IMIDAZOPYRIDINE DERIVATIVES AND AZA-IMIDAZOPYRIDINE DERIVATIVES AS JANUS KINASE 2 INHIBITORS AND USES THEREOF |
| CA3181537A1 (en) | 2020-05-06 | 2021-11-11 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| EP4267574B1 (en) | 2020-12-23 | 2025-04-23 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| JP2024500919A (ja) | 2020-12-23 | 2024-01-10 | ジェンザイム・コーポレーション | 重水素化コロニー刺激因子－１受容体（ｃｓｆ－１ｒ）阻害剤 |
| JP2024517695A (ja) * | 2021-04-29 | 2024-04-23 | アムジエン・インコーポレーテツド | 複素環式化合物及び使用方法 |
| 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 |
| TW202325289A (zh) | 2021-11-09 | 2023-07-01 | 美商雅捷可斯治療公司 | Ｊａｋ２抑制劑之形式及組合物 |
| JP7782035B2 (ja) | 2021-11-09 | 2025-12-08 | エイジャックス セラピューティクス， インコーポレイテッド | Ｊａｋ２阻害剤としての６－ヘテロアリールオキシベンゾイミダゾール及びアザベンゾイミダゾール |
Family Cites Families (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3691016A (en) | 1970-04-17 | 1972-09-12 | Monsanto Co | Process for the preparation of insoluble enzymes |
| CA1023287A (en) | 1972-12-08 | 1977-12-27 | Boehringer Mannheim G.M.B.H. | Process for the preparation of carrier-bound proteins |
| US4179337A (en) | 1973-07-20 | 1979-12-18 | Davis Frank F | Non-immunogenic polypeptides |
| US4195128A (en) | 1976-05-03 | 1980-03-25 | Bayer Aktiengesellschaft | Polymeric carrier bound ligands |
| US4330440A (en) | 1977-02-08 | 1982-05-18 | Development Finance Corporation Of New Zealand | Activated matrix and method of activation |
| CA1093991A (en) | 1977-02-17 | 1981-01-20 | Hideo Hirohara | Enzyme immobilization with pullulan gel |
| US4229537A (en) | 1978-02-09 | 1980-10-21 | New York University | Preparation of trichloro-s-triazine activated supports for coupling ligands |
| US4289872A (en) | 1979-04-06 | 1981-09-15 | Allied Corporation | Macromolecular highly branched homogeneous compound based on lysine units |
| JPS6023084B2 (ja) | 1979-07-11 | 1985-06-05 | 味の素株式会社 | 代用血液 |
| US4640835A (en) | 1981-10-30 | 1987-02-03 | Nippon Chemiphar Company, Ltd. | Plasminogen activator derivatives |
| US4496689A (en) | 1983-12-27 | 1985-01-29 | Miles Laboratories, Inc. | Covalently attached complex of alpha-1-proteinase inhibitor with a water soluble polymer |
| DE3675588D1 (de) | 1985-06-19 | 1990-12-20 | Ajinomoto Kk | Haemoglobin, das an ein poly(alkenylenoxid) gebunden ist. |
| US4791192A (en) | 1986-06-26 | 1988-12-13 | Takeda Chemical Industries, Ltd. | Chemically modified protein with polyethyleneglycol |
| EP0545913B1 (en) | 1986-08-18 | 1999-02-24 | Emisphere Technologies, Inc. | Delivery systems for pharmacological agents |
| US5229490A (en) | 1987-05-06 | 1993-07-20 | The Rockefeller University | Multiple antigen peptide system |
| GB8827305D0 (en) | 1988-11-23 | 1988-12-29 | British Bio Technology | Compounds |
| US5013556A (en) | 1989-10-20 | 1991-05-07 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
| CA2118130A1 (en) | 1992-04-14 | 1993-10-28 | Jean M. J. Frechet | Dendritic based macromolecules and method of production |
| US5646176A (en) | 1992-12-24 | 1997-07-08 | Bristol-Myers Squibb Company | Phosphonooxymethyl ethers of taxane derivatives |
| US5455258A (en) | 1993-01-06 | 1995-10-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
| US5863949A (en) | 1995-03-08 | 1999-01-26 | Pfizer Inc | Arylsulfonylamino hydroxamic acid derivatives |
| DK0821671T3 (da) | 1995-04-20 | 2001-04-23 | Pfizer | Arylsulfonylhydroxamsyrederivater som MMP- og TNF-inhibitorer |
| DE69624081T2 (de) | 1995-12-20 | 2003-06-12 | Agouron Pharmaceuticals, Inc. | Matrix-metalloprotease Inhibitoren |
| EP0923585B1 (en) | 1996-07-18 | 2002-05-08 | Pfizer Inc. | Phosphinate based inhibitors of matrix metalloproteases |
| WO1998007697A1 (en) | 1996-08-23 | 1998-02-26 | Pfizer Inc. | Arylsulfonylamino hydroxamic acid derivatives |
| WO1998030566A1 (en) | 1997-01-06 | 1998-07-16 | Pfizer Inc. | Cyclic sulfone derivatives |
| EP0977733B1 (en) | 1997-02-03 | 2003-09-03 | Pfizer Products Inc. | Arylsulfonylamino hydroxamic acid derivatives |
| JP2000507975A (ja) | 1997-02-07 | 2000-06-27 | ファイザー・インク | Ｎ−ヒドロキシ−β−スルホニルプロピオンアミド誘導体類及びそれらのマトリックスメタロプロテイナーゼ阻害薬としての使用 |
| EA002546B1 (ru) | 1997-02-11 | 2002-06-27 | Пфайзер Инк. | Производные арилсульфонилгидроксамовой кислоты |
| US6605599B1 (en) | 1997-07-08 | 2003-08-12 | Bristol-Myers Squibb Company | Epothilone derivatives |
| GB9725782D0 (en) | 1997-12-05 | 1998-02-04 | Pfizer Ltd | Therapeutic agents |
| GB9801690D0 (en) | 1998-01-27 | 1998-03-25 | Pfizer Ltd | Therapeutic agents |
| PA8469401A1 (es) | 1998-04-10 | 2000-05-24 | Pfizer Prod Inc | Derivados biciclicos del acido hidroxamico |
| PA8469501A1 (es) | 1998-04-10 | 2000-09-29 | Pfizer Prod Inc | Hidroxamidas del acido (4-arilsulfonilamino)-tetrahidropiran-4-carboxilico |
| BR0008379A (pt) | 1999-02-22 | 2002-09-24 | Biotechnolog Forschung Gmbh | Epotilonas modificadas em c-21 |
| EP1644528A2 (en) | 2003-06-19 | 2006-04-12 | THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, the Department of Health and Human Services, | Variants of human taste receptor genes |
| CA2536470A1 (en) | 2003-08-15 | 2005-02-24 | Vertex Pharmaceuticals Incorporated | Pyrrole compositions useful as inhibitors of c-met |
| AR045595A1 (es) | 2003-09-04 | 2005-11-02 | Vertex Pharma | Composiciones utiles como inhibidores de proteinas quinasas |
| AU2004284420A1 (en) | 2003-09-24 | 2005-05-06 | Vertex Pharmaceuticals Incorporated | 4-azole substituted imidazole compositions useful as inhibitors or c-Met receptor tyrosine kinase |
| PT2213661E (pt) | 2003-09-26 | 2011-12-15 | Exelixis Inc | Moduladores de c-met e métodos de uso |
| CA2546353A1 (en) | 2003-11-19 | 2005-06-09 | Array Biopharma Inc. | Bicyclic inhibitors of mek and methods of use thereof |
| US7459562B2 (en) | 2004-04-23 | 2008-12-02 | Bristol-Myers Squibb Company | Monocyclic heterocycles as kinase inhibitors |
| US7432373B2 (en) | 2004-06-28 | 2008-10-07 | Bristol-Meyers Squibb Company | Processes and intermediates useful for preparing fused heterocyclic kinase inhibitors |
| US7439246B2 (en) | 2004-06-28 | 2008-10-21 | Bristol-Myers Squibb Company | Fused heterocyclic kinase inhibitors |
| US7173031B2 (en) | 2004-06-28 | 2007-02-06 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| CA2572331A1 (en) | 2004-07-02 | 2006-02-09 | Exelixis, Inc. | C-met modulators and method of use |
| BR122020017756B1 (pt) | 2004-08-26 | 2022-02-15 | Pfizer Inc | Uso de compostos de aminoeteroarila enantiomericamente puros na preparação de um medicamento para o tratamento de crescimento celular anormal em um mamífero |
| ME01309B (me) | 2004-08-26 | 2013-12-20 | Pfizer | Pirazolom supstituirani heteroarilni spojevi kao inhibitori proteinskih kinaza |
| BRPI0514687A (pt) | 2004-08-26 | 2008-06-17 | Pfizer | compostos amino heteroarila como inibidores de proteìna tirosina cinase |
| ATE482213T1 (de) | 2004-11-04 | 2010-10-15 | Vertex Pharma | Als inhibitoren von proteinkinasen geeignete pyrazoloä1,5-aüpyrimidine |
| US20080161305A1 (en) | 2005-04-06 | 2008-07-03 | Exelixis, Inc. | C-Met Modulators and Methods of Use |
| US7470693B2 (en) | 2005-04-21 | 2008-12-30 | Bristol-Myers Squibb Company | Oxalamide derivatives as kinase inhibitors |
| JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| US7348325B2 (en) | 2005-11-30 | 2008-03-25 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| KR20080080584A (ko) | 2005-11-30 | 2008-09-04 | 버텍스 파마슈티칼스 인코포레이티드 | ｃ-Ｍｅｔ의 억제제 및 이의 용도 |
| ES2336625T3 (es) | 2006-03-22 | 2010-04-14 | Vertex Pharmaceuticals Incorporated | Inhibidores de la proteina quinasa c-met para el tratamiento de trastornos proliferativos. |
| NL2000613C2 (nl) | 2006-05-11 | 2007-11-20 | Pfizer Prod Inc | Triazoolpyrazinederivaten. |
| TW200813021A (en) | 2006-07-10 | 2008-03-16 | Merck & Co Inc | Tyrosine kinase inhibitors |
| US8481538B2 (en) | 2006-09-18 | 2013-07-09 | Vertex Pharmaceuticals Incorporated | Heterocyclic inhibitors of c-Met and uses thereof |
| ATE543819T1 (de) * | 2006-10-19 | 2012-02-15 | Signal Pharm Llc | Heteroarylverbindungen, zusammensetzungen daraus und behandlungsverfahren damit |
| CA2667453A1 (en) | 2006-10-23 | 2008-05-02 | Sgx Pharmaceuticals, Inc. | Triazolo-pyridazine protein kinase modulators |
| CA2668210C (en) | 2006-10-31 | 2013-03-12 | Schering Corporation | Anilinopiperazine derivatives and methods of use thereof |
| WO2008060866A1 (en) | 2006-11-14 | 2008-05-22 | Smithkline Beecham Corporation | Novel compounds |
| WO2008078085A1 (en) | 2006-12-22 | 2008-07-03 | Astrazeneca Ab | Method |
| WO2008088881A1 (en) | 2007-01-19 | 2008-07-24 | Xcovery, Inc. | Kinase inhibitor compounds |
| EP2119706A4 (en) | 2007-02-23 | 2011-04-27 | Eisai R&D Man Co Ltd | PYRIDINE OR PYRIMIDINE DERIVATIVITY WITH EXCELLENT CELL GROWTH-INHIBITORY EFFECT AND EXCELLENT ANTITUMOR EFFECT ON A CELL STRAIN WITH AN AMPLIFIED HGFR GENE |
| FR2915198B1 (fr) * | 2007-04-18 | 2009-12-18 | Sanofi Aventis | Derives de triazolopyridine-carboxamides et triazolopyridine -carboxamides, leur preparation et leur application en therapeutique. |
| WO2009002806A1 (en) | 2007-06-22 | 2008-12-31 | Arqule, Inc. | Pyrrolidinone, pyrrolidine-2, 5-dione, pyrrolidine and thiosuccinimide derivatives, compositions and methods for treatment of cancer |
| CA2703978A1 (en) | 2007-10-29 | 2009-05-07 | Schering Corporation | Thiazole derivatives as protein kinase inhibitors |
| WO2009058730A1 (en) | 2007-10-29 | 2009-05-07 | Schering Corporation | Diamido thiazole derivatives as protein kinase inhibitors |
| CA2703981A1 (en) | 2007-10-29 | 2009-05-07 | Schering Corporation | Heterocyclic urea and thiourea derivatives and methods of use thereof |
| CN101910167A (zh) | 2007-10-29 | 2010-12-08 | 先灵公司 | 噻唑甲酰胺衍生物及其治疗癌症 |
| KR101667822B1 (ko) * | 2008-04-30 | 2016-10-19 | 내셔날 헬스 리서치 인스티튜트 | 오로라 키나아제 저해제용 접합 2고리 피리미딘 화합물 |
| EP3795573B1 (en) * | 2009-12-31 | 2022-07-06 | Hutchison Medipharma Limited | Certain triazolopyrazines, compositions thereof and methods of use therefor |
| 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 |
| JP5960688B2 (ja) | 2010-05-17 | 2016-08-02 | インコゼン セラピューティクス プライベート リミテッド | プロテインキナーゼ調節物質としての新規３，５−二置換−３ｈ−［１，２，３］トリアゾロ［４，５−ｂ］ピリジン化合物 |
| EP2831073B1 (en) * | 2012-03-30 | 2020-12-09 | Rhizen Pharmaceuticals S.A. | 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 c-met protein kinases |
| 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 EP EP13716061.0A patent/EP2831073B1/en not_active Not-in-force
- 2013-02-27 WO PCT/IB2013/051577 patent/WO2013144737A2/en not_active Ceased
- 2013-02-27 MY MYPI2014002712A patent/MY169268A/en unknown
- 2013-02-27 AU AU2013239398A patent/AU2013239398B2/en not_active Ceased
- 2013-02-27 KR KR1020207002779A patent/KR102164317B1/ko not_active Expired - Fee Related
- 2013-02-27 NZ NZ629499A patent/NZ629499A/en not_active IP Right Cessation
- 2013-02-27 SG SG11201406185WA patent/SG11201406185WA/en unknown
- 2013-02-27 CN CN201710062943.0A patent/CN107082779A/zh active Pending
- 2013-02-27 KR KR1020147030532A patent/KR20140144726A/ko not_active Ceased
- 2013-02-27 BR BR112014024251A patent/BR112014024251A8/pt not_active IP Right Cessation
- 2013-02-27 AP AP2014007966A patent/AP3908A/en active
- 2013-02-27 CN CN201380022471.6A patent/CN104321322A/zh active Pending
- 2013-02-27 EA EA201491520A patent/EA026412B1/ru unknown
- 2013-02-27 US US14/389,336 patent/US9815831B2/en not_active Expired - Fee Related
- 2013-02-27 ES ES13716061T patent/ES2856848T3/es active Active
- 2013-02-27 JP JP2015502481A patent/JP6192708B2/ja not_active Expired - Fee Related
- 2013-02-27 MX MX2014011750A patent/MX359888B/es active IP Right Grant
- 2013-02-27 CA CA2865719A patent/CA2865719C/en active Active
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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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