ES2528269T3 - Azaindazoles - Google Patents

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Publication number

ES2528269T3

ES2528269T3 ES11803965.0T ES11803965T ES2528269T3 ES 2528269 T3 ES2528269 T3 ES 2528269T3 ES 11803965 T ES11803965 T ES 11803965T ES 2528269 T3 ES2528269 T3 ES 2528269T3

Authority

ES

Spain

Prior art keywords

methyl

alkyl

pyridinyl

oxo

dihydro

Prior art date

2010-05-07

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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• -1 substituted Chemical class 0.000 claims abstract description 233
• 150000001875 compounds Chemical class 0.000 claims abstract description 195
• 229910003827 NRaRb Inorganic materials 0.000 claims abstract description 154
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 93
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 92
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 80
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 79
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 77
• 125000003118 aryl group Chemical group 0.000 claims abstract description 71
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 70
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 66
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 60
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 52
• 239000001257 hydrogen Substances 0.000 claims abstract description 50
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 49
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 43
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 41
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 41
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 38
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 37
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 31
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract description 29
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 229910052701 rubidium Inorganic materials 0.000 claims abstract description 27
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 22
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 20
• 150000001602 bicycloalkyls Chemical group 0.000 claims abstract description 18
• 229910052717 sulfur Chemical group 0.000 claims abstract description 16
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 14
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 14
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims abstract description 13
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 10
• 239000001301 oxygen Substances 0.000 claims abstract description 10
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
• 229910006074 SO2NH2 Inorganic materials 0.000 claims abstract description 9
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 9
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
• 239000011593 sulfur Chemical group 0.000 claims abstract description 7
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 6
• 125000005843 halogen group Chemical group 0.000 claims abstract 30
• 238000011282 treatment Methods 0.000 claims description 57
• 206010028980 Neoplasm Diseases 0.000 claims description 52
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 41
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 31
• 201000011510 cancer Diseases 0.000 claims description 29
• 102100038970 Histone-lysine N-methyltransferase EZH2 Human genes 0.000 claims description 24
• 101000882127 Homo sapiens Histone-lysine N-methyltransferase EZH2 Proteins 0.000 claims description 24
• FABMZTHRDOHPDN-UHFFFAOYSA-N 6-chloro-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(Cl)N=C2N(C(C)C)N=CC2=C1C(=O)NCC1=C(C)C=C(C)NC1=O FABMZTHRDOHPDN-UHFFFAOYSA-N 0.000 claims description 23
• 125000001188 haloalkyl group Chemical group 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims description 17
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 10
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 8
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 8
• 238000002560 therapeutic procedure Methods 0.000 claims description 8
• 238000002360 preparation method Methods 0.000 claims description 7
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 6
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
• CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000004442 acylamino group Chemical group 0.000 claims description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 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 description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 230000001404 mediated effect Effects 0.000 claims description 5
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 4
• GULQTEYKOJRRSJ-UHFFFAOYSA-N 6-chloro-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(Cl)N=C2N(C(C)C)N=C(C)C2=C1C(=O)NCC1=C(C)C=C(C)NC1=O GULQTEYKOJRRSJ-UHFFFAOYSA-N 0.000 claims description 4
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
• DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 4
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 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 description 4
• WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 4
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 4
• 229930192474 thiophene Natural products 0.000 claims description 4
• 150000003852 triazoles Chemical class 0.000 claims description 4
• 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 description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
• 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 description 2
• XDHHENMFFCOFQP-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound NC(=O)C1=CC=NC2=C1C=NN2 XDHHENMFFCOFQP-UHFFFAOYSA-N 0.000 claims description 2
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 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 description 2
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 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 description 2
• 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 description 2
• OXYLZYCQFHCRDZ-UHFFFAOYSA-N 6-(benzylamino)-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=C1NCC1=CC=CC=C1 OXYLZYCQFHCRDZ-UHFFFAOYSA-N 0.000 claims description 2
• PYPWLVFEJOOVDR-UHFFFAOYSA-N 6-[2-(dimethylamino)ethylamino]-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(NCCN(C)C)N=C2N(C(C)C)N=CC2=C1C(=O)NCC1=C(C)C=C(C)NC1=O PYPWLVFEJOOVDR-UHFFFAOYSA-N 0.000 claims description 2
• VZGZROHQXCXVNG-UHFFFAOYSA-N 6-[6-(dimethylamino)pyridin-3-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=C(N(C)C)N=C1 VZGZROHQXCXVNG-UHFFFAOYSA-N 0.000 claims description 2
• SEKDNVJKSGMKBR-UHFFFAOYSA-N 6-amino-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(N)N=C2N(C(C)C)N=CC2=C1C(=O)NCC1=C(C)C=C(C)NC1=O SEKDNVJKSGMKBR-UHFFFAOYSA-N 0.000 claims description 2
• ZJBQVJXGTZEWCX-UHFFFAOYSA-N 6-anilino-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=CC=C1 ZJBQVJXGTZEWCX-UHFFFAOYSA-N 0.000 claims description 2
• OAANCGPNPUHUAK-UHFFFAOYSA-N 6-cyclopropyl-n-[(6-cyclopropyl-4-methyl-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(=CC=2C)C2CC2)=O)C=C1C1CC1 OAANCGPNPUHUAK-UHFFFAOYSA-N 0.000 claims description 2
• GDDSMOUZBSWFPX-UHFFFAOYSA-N 6-cyclopropyl-n-[(6-methyl-2-oxo-4-phenyl-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=2C=CC=CC=2)=O)C=C1C1CC1 GDDSMOUZBSWFPX-UHFFFAOYSA-N 0.000 claims description 2
• YBGKRLSRBCWQEQ-UHFFFAOYSA-N 6-cyclopropyl-n-[(6-methyl-2-oxo-4-propan-2-yl-1h-pyridin-3-yl)methyl]-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C1=C(C)NC(=O)C(CNC(=O)C=2C=3C=NN(C=3N=C(C=2)C2CC2)C(C)C)=C1C(C)C YBGKRLSRBCWQEQ-UHFFFAOYSA-N 0.000 claims description 2
• FSDXIBKXOHYNOA-UHFFFAOYSA-N 6-cyclopropyl-n-[(6-methyl-2-oxo-4-propyl-1h-pyridin-3-yl)methyl]-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C1=C(C)NC(=O)C(CNC(=O)C=2C=3C=NN(C=3N=C(C=2)C2CC2)C(C)C)=C1CCC FSDXIBKXOHYNOA-UHFFFAOYSA-N 0.000 claims description 2
• DHKHLSCPKJCJNP-UHFFFAOYSA-N 6-cyclopropyl-n-[[6-methyl-2-oxo-4-(trifluoromethyl)-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(F)(F)F)=O)C=C1C1CC1 DHKHLSCPKJCJNP-UHFFFAOYSA-N 0.000 claims description 2
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• RVPHJHONMNAGSK-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1,6-di(propan-2-yl)pyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C=12C=NN(C(C)C)C2=NC(C(C)C)=CC=1C(=O)NCC1=C(C)C=C(C)NC1=O RVPHJHONMNAGSK-UHFFFAOYSA-N 0.000 claims description 2
• LVQZSFQDGDBHJW-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-yl-6-(2-pyridin-4-ylethynyl)pyrazolo[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#CC1=CC=NC=C1 LVQZSFQDGDBHJW-UHFFFAOYSA-N 0.000 claims description 2
• MMDJLTWESKNNRE-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-yl-6-(prop-2-enylamino)pyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C1=C(NCC=C)N=C2N(C(C)C)N=CC2=C1C(=O)NCC1=C(C)C=C(C)NC1=O MMDJLTWESKNNRE-UHFFFAOYSA-N 0.000 claims description 2
• LYTGPDCLJDARQE-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-1-propan-2-yl-6-(pyridin-4-ylmethylamino)pyrazolo[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=C1NCC1=CC=NC=C1 LYTGPDCLJDARQE-UHFFFAOYSA-N 0.000 claims description 2
• YWNPYDHFOXXNNH-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(2-phenylethyl)-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=C1CCC1=CC=CC=C1 YWNPYDHFOXXNNH-UHFFFAOYSA-N 0.000 claims description 2
• WCUROQOMQQPYKI-UHFFFAOYSA-N n-[(4,6-dimethyl-2-oxo-1h-pyridin-3-yl)methyl]-6-(2-phenylethynyl)-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#CC1=CC=CC=C1 WCUROQOMQQPYKI-UHFFFAOYSA-N 0.000 claims description 2
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