JP2013527173A5 - - Google Patents
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- Publication number
- JP2013527173A5 JP2013527173A5 JP2013509262A JP2013509262A JP2013527173A5 JP 2013527173 A5 JP2013527173 A5 JP 2013527173A5 JP 2013509262 A JP2013509262 A JP 2013509262A JP 2013509262 A JP2013509262 A JP 2013509262A JP 2013527173 A5 JP2013527173 A5 JP 2013527173A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyridinyl
- oxo
- dihydro
- pyridine
- 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 where said ring Chemical group 0.000 claims 82
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 43
- 125000001072 heteroaryl group Chemical group 0.000 claims 36
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 33
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 30
- 125000003118 aryl group Chemical group 0.000 claims 27
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 19
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 16
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 14
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 10
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 150000001602 bicycloalkyls Chemical group 0.000 claims 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000003107 substituted aryl group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 229910052717 sulfur Chemical group 0.000 claims 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- 206010038389 Renal cancer Diseases 0.000 claims 2
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 201000010982 kidney cancer Diseases 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- SNICLKHAPMIQAK-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound N1=C2N(C(C)C)N=CC2=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C=C1C(C=N1)=CC=C1N1CCN(C)CC1 SNICLKHAPMIQAK-UHFFFAOYSA-N 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 2
- 150000003536 tetrazoles Chemical class 0.000 claims 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 150000003852 triazoles Chemical class 0.000 claims 2
- JCWWOICHWDKSPS-UHFFFAOYSA-N 1,6-ditert-butyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C=12C(C)=NN(C(C)(C)C)C2=NC(C(C)(C)C)=CC=1C(=O)NCC1=C(C)C=C(C)NC1=O JCWWOICHWDKSPS-UHFFFAOYSA-N 0.000 claims 1
- CKQCYGJHRBQQHV-UHFFFAOYSA-N 1-(2-aminoethyl)-6-cyclopropyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]pyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(C2CC2)=NC2=C1C=NN2CCN CKQCYGJHRBQQHV-UHFFFAOYSA-N 0.000 claims 1
- ZPVOFDSZWZKZJS-UHFFFAOYSA-N 1-amino-6-cyclopropyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]pyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound O=C1NC(C)=CC(C)=C1CNC(=O)C1=CC(C2CC2)=NC2=C1C=NN2N ZPVOFDSZWZKZJS-UHFFFAOYSA-N 0.000 claims 1
- FTRNTBOWPSRAEH-UHFFFAOYSA-N 1-benzyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-methylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C=12C=NN(CC=3C=CC=CC=3)C2=NC(C)=CC=1C(=O)NCC1=C(C)C=C(C)NC1=O FTRNTBOWPSRAEH-UHFFFAOYSA-N 0.000 claims 1
- IIDGHJNVOYHFLT-UHFFFAOYSA-N 1-cyclobutyl-6-cyclopropyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C12=NC(C3CC3)=CC(C(=O)NCC=3C(NC(C)=CC=3C)=O)=C2C(C)=NN1C1CCC1 IIDGHJNVOYHFLT-UHFFFAOYSA-N 0.000 claims 1
- ZVWGPMUZNXVNEB-UHFFFAOYSA-N 1-cyclohexyl-6-cyclopropyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C12=NC(C3CC3)=CC(C(=O)NCC=3C(NC(C)=CC=3C)=O)=C2C(C)=NN1C1CCCCC1 ZVWGPMUZNXVNEB-UHFFFAOYSA-N 0.000 claims 1
- BCXVOWWRYJQHNM-UHFFFAOYSA-N 1-cyclopentyl-6-cyclopropyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C12=NC(C3CC3)=CC(C(=O)NCC=3C(NC(C)=CC=3C)=O)=C2C(C)=NN1C1CCCC1 BCXVOWWRYJQHNM-UHFFFAOYSA-N 0.000 claims 1
- VKSDJJINVLWPPN-UHFFFAOYSA-N 1-tert-butyl-6-chloro-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C=12C(C)=NN(C(C)(C)C)C2=NC(Cl)=CC=1C(=O)NCC1=C(C)C=C(C)NC1=O VKSDJJINVLWPPN-UHFFFAOYSA-N 0.000 claims 1
- VUJVCWWIQRDSNQ-UHFFFAOYSA-N 1-tert-butyl-6-cyclopropyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C=12C(C)=NN(C(C)(C)C)C2=NC(C2CC2)=CC=1C(=O)NCC1=C(C)C=C(C)NC1=O VUJVCWWIQRDSNQ-UHFFFAOYSA-N 0.000 claims 1
- GBNAZZHFAWCZDP-UHFFFAOYSA-N 1-tert-butyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methyl-6-(2-oxo-1,3-dihydrobenzimidazol-5-yl)pyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C=12C(C)=NN(C(C)(C)C)C2=NC(C=2C=C3NC(=O)NC3=CC=2)=CC=1C(=O)NCC1=C(C)C=C(C)NC1=O GBNAZZHFAWCZDP-UHFFFAOYSA-N 0.000 claims 1
- KFGLSNDZHPVZLB-UHFFFAOYSA-N 1-tert-butyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methyl-6-(6-morpholin-4-ylpyridin-3-yl)pyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C=12C(C)=NN(C(C)(C)C)C2=NC(C=2C=NC(=CC=2)N2CCOCC2)=CC=1C(=O)NCC1=C(C)C=C(C)NC1=O KFGLSNDZHPVZLB-UHFFFAOYSA-N 0.000 claims 1
- MNFXCZXHQVNDKD-UHFFFAOYSA-N 1-tert-butyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methyl-6-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]pyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(C=2N=C3N(N=C(C)C3=C(C(=O)NCC=3C(NC(C)=CC=3C)=O)C=2)C(C)(C)C)C=N1 MNFXCZXHQVNDKD-UHFFFAOYSA-N 0.000 claims 1
- ZOZATYKUQBINTC-UHFFFAOYSA-N 1-tert-butyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methyl-6-pyridin-3-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C=12C(C)=NN(C(C)(C)C)C2=NC(C=2C=NC=CC=2)=CC=1C(=O)NCC1=C(C)C=C(C)NC1=O ZOZATYKUQBINTC-UHFFFAOYSA-N 0.000 claims 1
- WFAPQHAQUNZYKQ-UHFFFAOYSA-N 1-tert-butyl-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(4-methoxyphenyl)-3-methylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC(C(=O)NCC=2C(NC(C)=CC=2C)=O)=C(C(C)=NN2C(C)(C)C)C2=N1 WFAPQHAQUNZYKQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- ZYGCNKBZFDOZPV-UHFFFAOYSA-N 6-(2,1,3-benzoxadiazol-5-yl)-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methyl-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C1=C(C2=CC3=NON=C3C=C2)N=C2N(C(C)C)N=C(C)C2=C1C(=O)NCC1=C(C)C=C(C)NC1=O ZYGCNKBZFDOZPV-UHFFFAOYSA-N 0.000 claims 1
- ROUZJNZVOLGBLI-UHFFFAOYSA-N 6-(2-aminopyridin-4-yl)-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound N1=C2N(C(C)C)N=CC2=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C=C1C1=CC=NC(N)=C1 ROUZJNZVOLGBLI-UHFFFAOYSA-N 0.000 claims 1
- JNXHLGFBCMVYNR-UHFFFAOYSA-N 6-(2-aminopyrimidin-5-yl)-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound N1=C2N(C(C)C)N=CC2=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C=C1C1=CN=C(N)N=C1 JNXHLGFBCMVYNR-UHFFFAOYSA-N 0.000 claims 1
- BBSASWROZCPDRJ-UHFFFAOYSA-N 6-(2h-benzotriazol-5-yl)-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C1=C(C=2C=C3N=NNC3=CC=2)N=C2N(C(C)C)N=CC2=C1C(=O)NCC1=C(C)C=C(C)NC1=O BBSASWROZCPDRJ-UHFFFAOYSA-N 0.000 claims 1
- PYZYAPPUGKUPEE-UHFFFAOYSA-N 6-(3-acetamidophenyl)-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound N1=C2N(C(C)C)N=CC2=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C=C1C1=CC=CC(NC(C)=O)=C1 PYZYAPPUGKUPEE-UHFFFAOYSA-N 0.000 claims 1
- CYKQSUGLXKUFHX-UHFFFAOYSA-N 6-(3-aminophenyl)-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound N1=C2N(C(C)C)N=CC2=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C=C1C1=CC=CC(N)=C1 CYKQSUGLXKUFHX-UHFFFAOYSA-N 0.000 claims 1
- GQCKGKFHRBAKCN-UHFFFAOYSA-N 6-(4-acetamidophenyl)-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound N1=C2N(C(C)C)N=CC2=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C=C1C1=CC=C(NC(C)=O)C=C1 GQCKGKFHRBAKCN-UHFFFAOYSA-N 0.000 claims 1
- SPDITUWEEYOCJY-UHFFFAOYSA-N 6-(4-acetamidophenyl)-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-3-methyl-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound N1=C2N(C(C)C)N=C(C)C2=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C=C1C1=CC=C(NC(C)=O)C=C1 SPDITUWEEYOCJY-UHFFFAOYSA-N 0.000 claims 1
- NCTMOSCJBLHHAG-UHFFFAOYSA-N 6-(4-aminophenyl)-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound N1=C2N(C(C)C)N=CC2=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C=C1C1=CC=C(N)C=C1 NCTMOSCJBLHHAG-UHFFFAOYSA-N 0.000 claims 1
- KWPKXQFYRMVTLS-UHFFFAOYSA-N 6-(4-carbamoylanilino)-n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound N1=C2N(C(C)C)N=CC2=C(C(=O)NCC=2C(NC(C)=CC=2C)=O)C=C1NC1=CC=C(C(N)=O)C=C1 KWPKXQFYRMVTLS-UHFFFAOYSA-N 0.000 claims 1
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| JP5864546B2 (ja) | 2010-05-07 | 2016-02-17 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | インダゾール |
| CA2841142C (en) | 2010-06-23 | 2020-12-15 | Ryan D. Morin | Biomarkers for non-hodgkin lymphomas and uses thereof |
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2011
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- 2011-05-05 EP EP11803965.0A patent/EP2566479B1/en not_active Not-in-force
- 2011-05-05 JP JP2013509262A patent/JP5889875B2/ja not_active Expired - Fee Related
- 2011-05-05 WO PCT/US2011/035344 patent/WO2012005805A1/en not_active Ceased
- 2011-05-05 US US13/696,601 patent/US8637509B2/en not_active Expired - Fee Related
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