JPWO2019191229A5

JPWO2019191229A5 -

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Publication number: JPWO2019191229A5
Authority: JP; Japan
Prior art keywords: triazine; phenol; methyl; amino; pyrazole
Prior art date: 2022-03-30
Legal status : Granted

Application number

JP2020551538A

Other languages

English (en)

Japanese (ja)

Other versions

JP7399869B2 (ja

JP2021519291A (ja

Publication date

2022-03-30

2019-03-27 Application filed filed Critical

2019-03-27 Priority claimed from PCT/US2019/024278 external-priority patent/WO2019191229A1/en

2021-08-10 Publication of JP2021519291A publication Critical patent/JP2021519291A/ja

2022-03-30 Publication of JPWO2019191229A5 publication Critical patent/JPWO2019191229A5/ja

2023-12-18 Application granted granted Critical

2023-12-18 Publication of JP7399869B2 publication Critical patent/JP7399869B2/ja

Status Active legal-status Critical Current

2039-03-27 Anticipated expiration legal-status Critical

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-1 {[(pyridine-2-yl) Methyl] Amino} Methyl Chemical group 0.000 claims description 590
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 166
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 123
125000000217 alkyl group Chemical group 0.000 claims description 44
150000001875 compounds Chemical class 0.000 claims description 38
125000003545 alkoxy group Chemical group 0.000 claims description 24
125000001424 substituent group Chemical group 0.000 claims description 11
125000002619 bicyclic group Chemical group 0.000 claims description 7
125000002950 monocyclic group Chemical group 0.000 claims description 7
229920006395 saturated elastomer Polymers 0.000 claims description 6
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 193
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 55
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 51
JELQZSVKOONUKD-UHFFFAOYSA-N phenol dihydrochloride Chemical compound Cl.Cl.OC1=CC=CC=C1.OC1=CC=CC=C1 JELQZSVKOONUKD-UHFFFAOYSA-N 0.000 claims 29
125000004076 pyridyl group Chemical group 0.000 claims 23
125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 20
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 17
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 11
125000000623 heterocyclic group Chemical group 0.000 claims 10
150000003839 salts Chemical class 0.000 claims 10
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 9
ZXRCAYWYTOIRQS-UHFFFAOYSA-N hydron;phenol;chloride Chemical compound Cl.OC1=CC=CC=C1 ZXRCAYWYTOIRQS-UHFFFAOYSA-N 0.000 claims 8
OXDLBBKNAAFZNI-UHFFFAOYSA-N phenol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC1=CC=CC=C1 OXDLBBKNAAFZNI-UHFFFAOYSA-N 0.000 claims 8
125000001072 heteroaryl group Chemical group 0.000 claims 7
229910052760 oxygen Inorganic materials 0.000 claims 7
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 6
239000008194 pharmaceutical composition Substances 0.000 claims 6
125000004093 cyano group Chemical group *C#N 0.000 claims 5
229910052736 halogen Inorganic materials 0.000 claims 5
150000002367 halogens Chemical class 0.000 claims 5
125000005842 heteroatom Chemical group 0.000 claims 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
150000002460 imidazoles Chemical class 0.000 claims 5
GEOWCLRLLWTHDN-UHFFFAOYSA-N phenyl formate Chemical compound O=COC1=CC=CC=C1 GEOWCLRLLWTHDN-UHFFFAOYSA-N 0.000 claims 5
125000000714 pyrimidinyl group Chemical group 0.000 claims 5
229910052717 sulfur Inorganic materials 0.000 claims 5
YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims 4
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 4
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 4
VRESBNUEIKZECD-UHFFFAOYSA-N 2-methyltetrazole Chemical compound CN1N=CN=N1 VRESBNUEIKZECD-UHFFFAOYSA-N 0.000 claims 4
XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 4
125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 4
UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 claims 4
239000002253 acid Substances 0.000 claims 4
125000003282 alkyl amino group Chemical group 0.000 claims 4
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 3
125000000033 alkoxyamino group Chemical group 0.000 claims 3
125000004122 cyclic group Chemical group 0.000 claims 3
AYEMKBIEDPMVLE-UHFFFAOYSA-N phenol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC1=CC=CC=C1 AYEMKBIEDPMVLE-UHFFFAOYSA-N 0.000 claims 3
125000002098 pyridazinyl group Chemical group 0.000 claims 3
125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 2
125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims 2
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 2
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 2
125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims 2
125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 2
125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
CSUGQXMRKOKBFI-UHFFFAOYSA-N 1-methylindazole Chemical compound C1=CC=C2N(C)N=CC2=C1 CSUGQXMRKOKBFI-UHFFFAOYSA-N 0.000 claims 2
AZWPZEGGNCFEKN-UHFFFAOYSA-N 1-methylpyrazolo[3,4-b]pyridine Chemical compound C1=CN=C2N(C)N=CC2=C1 AZWPZEGGNCFEKN-UHFFFAOYSA-N 0.000 claims 2
125000005955 1H-indazolyl group Chemical group 0.000 claims 2
GDUVBKSVYWFWGV-UHFFFAOYSA-N 2-(1h-pyrazol-4-yl)phenol Chemical compound OC1=CC=CC=C1C1=CNN=C1 GDUVBKSVYWFWGV-UHFFFAOYSA-N 0.000 claims 2
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 2
NGCXHCGUQHIOLZ-UHFFFAOYSA-N 2-methyltriazole Chemical compound CN1N=CC=N1 NGCXHCGUQHIOLZ-UHFFFAOYSA-N 0.000 claims 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 claims 2
XZGLNCKSNVGDNX-UHFFFAOYSA-N 5-methyl-2h-tetrazole Chemical compound CC=1N=NNN=1 XZGLNCKSNVGDNX-UHFFFAOYSA-N 0.000 claims 2
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 2
229910052805 deuterium Inorganic materials 0.000 claims 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
125000002883 imidazolyl group Chemical group 0.000 claims 2
125000002971 oxazolyl group Chemical group 0.000 claims 2
239000000546 pharmaceutical excipient Substances 0.000 claims 2
125000004193 piperazinyl group Chemical group 0.000 claims 2
125000003386 piperidinyl group Chemical group 0.000 claims 2
125000003373 pyrazinyl group Chemical group 0.000 claims 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
239000012453 solvate Substances 0.000 claims 2
125000001544 thienyl group Chemical group 0.000 claims 2
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims 1
125000005960 1,4-diazepanyl group Chemical group 0.000 claims 1
KXSIGCKZTIHSHU-UHFFFAOYSA-N 1-[1-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]imidazol-4-yl]ethanone Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)N1C=NC(=C1)C(C)=O KXSIGCKZTIHSHU-UHFFFAOYSA-N 0.000 claims 1
SYQTZXSPALHUDB-UHFFFAOYSA-N 1-[1-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]imidazol-4-yl]ethanone dihydrochloride Chemical compound Cl.Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-n1cnc(c1)C(C)=O SYQTZXSPALHUDB-UHFFFAOYSA-N 0.000 claims 1
IOGRSYJMACDTCZ-UHFFFAOYSA-N 1-[1-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]pyrazol-4-yl]ethanone Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)N1C=C(C=N1)C(C)=O IOGRSYJMACDTCZ-UHFFFAOYSA-N 0.000 claims 1
QBFIYMLATFUYIN-UHFFFAOYSA-N 1-[1-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]pyrazol-4-yl]ethanone dihydrochloride Chemical compound Cl.Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-n1cc(cn1)C(C)=O QBFIYMLATFUYIN-UHFFFAOYSA-N 0.000 claims 1
WKUSMYTZYNHVKC-UHFFFAOYSA-N 1-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]imidazole-4-carbonitrile Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)N1C=NC(=C1)C#N WKUSMYTZYNHVKC-UHFFFAOYSA-N 0.000 claims 1
BFHIDFGQEWLRDR-UHFFFAOYSA-N 1-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]pyrazol-4-ol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)N1C=C(O)C=N1 BFHIDFGQEWLRDR-UHFFFAOYSA-N 0.000 claims 1
LAGKHQLJJAISGX-UHFFFAOYSA-N 1-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]pyrazole-4-carbonitrile Chemical compound C1=C(C=NN1C1=CC(=C(C2=CN=C(N=N2)N(C2CC(C)(C)NC(C2)(C)C)C)C=C1)O)C#N LAGKHQLJJAISGX-UHFFFAOYSA-N 0.000 claims 1
UKHJNJFJCGBKSF-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane Chemical compound C1NC2CNC1C2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 claims 1
RTRXUXZHOIUUOF-UHFFFAOYSA-N 2-(3-piperazin-1-yl-1,2,4-triazin-6-yl)-5-(1H-pyrazol-4-yl)phenol Chemical compound N1(CCNCC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O RTRXUXZHOIUUOF-UHFFFAOYSA-N 0.000 claims 1
BIASHOJVOWHKAG-UHFFFAOYSA-N 2-(3-piperazin-1-yl-1,2,4-triazin-6-yl)-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CCNCC1)-c1cn[nH]c1 BIASHOJVOWHKAG-UHFFFAOYSA-N 0.000 claims 1
IYTJXWUIRIBQOY-UHFFFAOYSA-N 2-[3-(1,7-diazaspiro[4.4]nonan-7-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CCC2(CCCN2)C1 IYTJXWUIRIBQOY-UHFFFAOYSA-N 0.000 claims 1
KOZMLNLEWQCQGL-UHFFFAOYSA-N 2-[3-(1,7-diazaspiro[4.4]nonan-7-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CCC2(CCCN2)C1)-c1cn[nH]c1 KOZMLNLEWQCQGL-UHFFFAOYSA-N 0.000 claims 1
TTXKQIMDHRHKAO-UHFFFAOYSA-N 2-[3-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[2,3-c]pyrrol-5-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CC2CCNC2C1 TTXKQIMDHRHKAO-UHFFFAOYSA-N 0.000 claims 1
JCODCOCZGCQGKJ-UHFFFAOYSA-N 2-[3-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CC2CNCC2C1 JCODCOCZGCQGKJ-UHFFFAOYSA-N 0.000 claims 1
HOYGMBCMNZNKSI-UHFFFAOYSA-N 2-[3-(2,6-diazaspiro[3.3]heptan-2-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C1N(CC11CNC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O HOYGMBCMNZNKSI-UHFFFAOYSA-N 0.000 claims 1
LHSPHGOHZVYXHN-UHFFFAOYSA-N 2-[3-(2,6-diazaspiro[3.3]heptan-2-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CC2(CNC2)C1)-c1cn[nH]c1 LHSPHGOHZVYXHN-UHFFFAOYSA-N 0.000 claims 1
KDAYHQLPHNLWIG-UHFFFAOYSA-N 2-[3-(2,6-diazaspiro[3.4]octan-6-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CCC2(CNC2)C1 KDAYHQLPHNLWIG-UHFFFAOYSA-N 0.000 claims 1
QLWOFFHFHNUPOC-UHFFFAOYSA-N 2-[3-(2,6-diazaspiro[3.4]octan-6-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CCC2(CNC2)C1)-c1cn[nH]c1 QLWOFFHFHNUPOC-UHFFFAOYSA-N 0.000 claims 1
XWCQKJQLZATXPQ-UHFFFAOYSA-N 2-[3-(2,6-dimethylpiperidin-4-yl)oxy-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CC1NC(CC(C1)OC=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C XWCQKJQLZATXPQ-UHFFFAOYSA-N 0.000 claims 1
KYHHCKWWXOYGBJ-UHFFFAOYSA-N 2-[3-(2,6-dimethylpiperidin-4-yl)oxy-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CC1CC(CC(C)N1)Oc1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 KYHHCKWWXOYGBJ-UHFFFAOYSA-N 0.000 claims 1
ZKAXNMKZMWKZJV-UHFFFAOYSA-N 2-[3-(2,7-diazaspiro[3.5]nonan-2-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CC2(C1)CCNCC2 ZKAXNMKZMWKZJV-UHFFFAOYSA-N 0.000 claims 1
CGQSMGNLJUXZCR-UHFFFAOYSA-N 2-[3-(2,7-diazaspiro[3.5]nonan-2-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CC2(C1)CCNCC2)-c1cn[nH]c1 CGQSMGNLJUXZCR-UHFFFAOYSA-N 0.000 claims 1
PWPFXPSTCYANTD-UHFFFAOYSA-N 2-[3-(2,7-diazaspiro[3.5]nonan-7-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CCC2(CNC2)CC1 PWPFXPSTCYANTD-UHFFFAOYSA-N 0.000 claims 1
JKPLNMKPIISUPR-UHFFFAOYSA-N 2-[3-(2,7-diazaspiro[3.5]nonan-7-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CCC2(CNC2)CC1)-c1cn[nH]c1 JKPLNMKPIISUPR-UHFFFAOYSA-N 0.000 claims 1
ZFDHVRLQWPRPNE-UHFFFAOYSA-N 2-[3-(2,7-diazaspiro[4.4]nonan-2-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CCC2(CCNC2)C1 ZFDHVRLQWPRPNE-UHFFFAOYSA-N 0.000 claims 1
DXDUWHWNDBYIDZ-UHFFFAOYSA-N 2-[3-(2,7-diazaspiro[4.4]nonan-2-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CCC2(CCNC2)C1)-c1cn[nH]c1 DXDUWHWNDBYIDZ-UHFFFAOYSA-N 0.000 claims 1
PHYSFFVRTLXKAK-UHFFFAOYSA-N 2-[3-(2,8-diazaspiro[3.5]nonan-2-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CC2(C1)CCCNC2 PHYSFFVRTLXKAK-UHFFFAOYSA-N 0.000 claims 1
FVIRDPLNRYHCRU-UHFFFAOYSA-N 2-[3-(2,8-diazaspiro[3.5]nonan-2-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CC2(C1)CCCNC2)-c1cn[nH]c1 FVIRDPLNRYHCRU-UHFFFAOYSA-N 0.000 claims 1
JBQOTZQLNDVXRN-UHFFFAOYSA-N 2-[3-(2,8-diazaspiro[4.5]decan-8-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CCC2(CCNC2)CC1 JBQOTZQLNDVXRN-UHFFFAOYSA-N 0.000 claims 1
ZDSMJENOMKGLGY-UHFFFAOYSA-N 2-[3-(2,8-diazaspiro[4.5]decan-8-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CCC2(CCNC2)CC1)-c1cn[nH]c1 ZDSMJENOMKGLGY-UHFFFAOYSA-N 0.000 claims 1
UQOJYKHOTKKMBD-UHFFFAOYSA-N 2-[3-(2,9-diazaspiro[4.5]decan-2-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CCC2(C1)CCCNC2 UQOJYKHOTKKMBD-UHFFFAOYSA-N 0.000 claims 1
GTQBAFJMSFWJHX-UHFFFAOYSA-N 2-[3-(2,9-diazaspiro[4.5]decan-2-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CCC2(C1)CCCNC2)-c1cn[nH]c1 GTQBAFJMSFWJHX-UHFFFAOYSA-N 0.000 claims 1
SKMPTKZJIXKLQW-UHFFFAOYSA-N 2-[3-(2,9-diazaspiro[5.5]undecan-9-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CCC2(CCCNC2)CC1 SKMPTKZJIXKLQW-UHFFFAOYSA-N 0.000 claims 1
QWTMWUQVVSUSTQ-UHFFFAOYSA-N 2-[3-(2,9-diazaspiro[5.5]undecan-9-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CCC2(CCCNC2)CC1)-c1cn[nH]c1 QWTMWUQVVSUSTQ-UHFFFAOYSA-N 0.000 claims 1
AOYVPCCFLIVVIV-UHFFFAOYSA-N 2-[3-(3,5-dimethylpiperazin-1-yl)-1,2,4-triazin-6-yl]-5-(1-methylpyrazol-3-yl)phenol Chemical compound CC1CN(CC(N1)C)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C1=NN(C=C1)C)O AOYVPCCFLIVVIV-UHFFFAOYSA-N 0.000 claims 1
VBKRSVWKRSKNGX-UHFFFAOYSA-N 2-[3-(3,5-dimethylpiperazin-1-yl)-1,2,4-triazin-6-yl]-5-(1-methylpyrazol-3-yl)phenol hydrochloride Chemical compound Cl.CC1CN(CC(C)N1)c1ncc(nn1)-c1ccc(cc1O)-c1ccn(C)n1 VBKRSVWKRSKNGX-UHFFFAOYSA-N 0.000 claims 1
VYFITHDPFHQHHH-UHFFFAOYSA-N 2-[3-(3,5-dimethylpiperazin-1-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CC1CN(CC(N1)C)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O VYFITHDPFHQHHH-UHFFFAOYSA-N 0.000 claims 1
BHCCWBJRKJRLLD-UHFFFAOYSA-N 2-[3-(3,5-dimethylpiperazin-1-yl)-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CC1CN(CC(C)N1)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 BHCCWBJRKJRLLD-UHFFFAOYSA-N 0.000 claims 1
LCMKGEJNRHCSTC-UHFFFAOYSA-N 2-[3-(3-amino-3-methylpyrrolidin-1-yl)-1,2,4-triazin-6-yl]-5-(1-methylpyrazol-4-yl)phenol Chemical compound CN1C=C(C=N1)C1=CC(O)=C(C=C1)C1=CN=C(N=N1)N1CCC(C)(N)C1 LCMKGEJNRHCSTC-UHFFFAOYSA-N 0.000 claims 1
OINCWCUVSOGRFZ-UHFFFAOYSA-N 2-[3-(7-methyl-2,7-diazaspiro[3.5]nonan-2-yl)-1,2,4-triazin-6-yl]-5-pyrimidin-2-ylphenol Chemical compound CN1CCC2(CN(C2)C2=NC=C(N=N2)C2=C(O)C=C(C=C2)C2=NC=CC=N2)CC1 OINCWCUVSOGRFZ-UHFFFAOYSA-N 0.000 claims 1
RUUKEZNHLWNXAZ-UHFFFAOYSA-N 2-[3-(7-methyl-2,7-diazaspiro[3.5]nonan-2-yl)-1,2,4-triazin-6-yl]-5-pyrimidin-2-ylphenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CN1CCC2(CN(C2)c2ncc(nn2)-c2ccc(cc2O)-c2ncccn2)CC1 RUUKEZNHLWNXAZ-UHFFFAOYSA-N 0.000 claims 1
CUPRXSAQLOXUPY-UHFFFAOYSA-N 2-[3-[(1-methylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN1CCC(CC1)NC1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1 CUPRXSAQLOXUPY-UHFFFAOYSA-N 0.000 claims 1
BKAQFANKJMHEHR-UHFFFAOYSA-N 2-[3-[(1-methylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol trihydrochloride Chemical compound Cl.Cl.Cl.CN1CCC(CC1)NC=1N=NC(=CN1)C1=C(C=C(C=C1)C=1C=NNC1)O BKAQFANKJMHEHR-UHFFFAOYSA-N 0.000 claims 1
KUXTXWOIEWDRGW-UHFFFAOYSA-N 2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-(1,2,4-triazin-6-yl)phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1(C)CC(CC(C)(C)N1)Nc1ncc(nn1)-c1ccc(cc1O)-c1cncnn1 KUXTXWOIEWDRGW-UHFFFAOYSA-N 0.000 claims 1
LKMQHHWRKPYYSE-UHFFFAOYSA-N 2-[3-[(3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-(triazol-2-yl)phenol Chemical compound CC1(C)CC(NC2=NC=C(N=N2)C2=C(O)C=C(C=C2)N2N=CC=N2)C(F)C(C)(C)N1 LKMQHHWRKPYYSE-UHFFFAOYSA-N 0.000 claims 1
FNXHTMAKPFTNII-MRXNPFEDSA-N 2-[3-[(3R)-3-(cyclobutylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound N1N=CC(=C1)C1=CC=C(C2=CN=C(N=N2)N2C[C@H](NC3CCC3)CC2)C(O)=C1 FNXHTMAKPFTNII-MRXNPFEDSA-N 0.000 claims 1
AJPYPUUUHOYAEV-OAHLLOKOSA-N 2-[3-[(3R)-3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)N[C@H]1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O AJPYPUUUHOYAEV-OAHLLOKOSA-N 0.000 claims 1
YUCTWSACDXMXCY-QCUBGVIVSA-N 2-[3-[(3R)-3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound CC(C)(C)N[C@@H]1CCN(C1)C2=NC=C(N=N2)C3=C(C=C(C=C3)C4=CNN=C4)O.Cl.Cl YUCTWSACDXMXCY-QCUBGVIVSA-N 0.000 claims 1
FXMVZFYAHLMTTD-ZDUSSCGKSA-N 2-[3-[(3S)-1-methylpyrrolidin-3-yl]oxy-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN1CC[C@@H](C1)OC1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1 FXMVZFYAHLMTTD-ZDUSSCGKSA-N 0.000 claims 1
NNMUAHGDYSOGQG-ZOWNYOTGSA-N 2-[3-[(3S)-1-methylpyrrolidin-3-yl]oxy-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol hydrochloride Chemical compound Cl.CN1CC[C@@H](C1)Oc1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 NNMUAHGDYSOGQG-ZOWNYOTGSA-N 0.000 claims 1
FNXHTMAKPFTNII-INIZCTEOSA-N 2-[3-[(3S)-3-(cyclobutylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound Oc1cc(ccc1-c1cnc(nn1)N1CC[C@@H](C1)NC1CCC1)-c1cn[nH]c1 FNXHTMAKPFTNII-INIZCTEOSA-N 0.000 claims 1
QZAUQAZOXKSADX-ZDUSSCGKSA-N 2-[3-[(3S)-3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN[C@@H]1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O QZAUQAZOXKSADX-ZDUSSCGKSA-N 0.000 claims 1
CDALUHTXKLNBJQ-GXKRWWSZSA-N 2-[3-[(3S)-3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CN[C@H]1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 CDALUHTXKLNBJQ-GXKRWWSZSA-N 0.000 claims 1
AJPYPUUUHOYAEV-HNNXBMFYSA-N 2-[3-[(3S)-3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CC(C)(C)N[C@H]1CCN(C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1 AJPYPUUUHOYAEV-HNNXBMFYSA-N 0.000 claims 1
YUCTWSACDXMXCY-CKUXDGONSA-N 2-[3-[(3S)-3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.C(C)(C)(C)N[C@@H]1CN(CC1)C=1N=NC(=CN1)C1=C(C=C(C=C1)C=1C=NNC1)O YUCTWSACDXMXCY-CKUXDGONSA-N 0.000 claims 1
FJDRQVJAQBLACX-DOMZBBRYSA-N 2-[3-[(3S)-3-[[(2R)-1-fluoropropan-2-yl]amino]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound FC[C@@H](C)N[C@@H]1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O FJDRQVJAQBLACX-DOMZBBRYSA-N 0.000 claims 1
IAMKMCQYYYUVQM-DKSSEZFCSA-N 2-[3-[(3aR,4R,6aS)-4-(dimethylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN([C@@H]1CC[C@@H]2CN(C[C@@H]21)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C IAMKMCQYYYUVQM-DKSSEZFCSA-N 0.000 claims 1
RAIONFDGXQOYOF-WBNIKMCISA-N 2-[3-[(3aR,4R,6aS)-4-(dimethylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound CN(C)[C@@H]1CC[C@H]2[C@@H]1CN(C2)C3=NC=C(N=N3)C4=C(C=C(C=C4)C5=CNN=C5)O.Cl.Cl RAIONFDGXQOYOF-WBNIKMCISA-N 0.000 claims 1
JAGWTUBTIQKLDR-AYOQOUSVSA-N 2-[3-[(3aR,4R,6aS)-4-(tert-butylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)N[C@@H]1CC[C@@H]2CN(C[C@@H]21)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O JAGWTUBTIQKLDR-AYOQOUSVSA-N 0.000 claims 1
VOYMBWAXLSRTMB-WUCMLCBTSA-N 2-[3-[(3aR,4R,6aS)-4-(tert-butylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound CC(C)(C)N[C@@H]1CC[C@H]2[C@@H]1CN(C2)C3=NC=C(N=N3)C4=C(C=C(C=C4)C5=CNN=C5)O.Cl.Cl VOYMBWAXLSRTMB-WUCMLCBTSA-N 0.000 claims 1
IAMKMCQYYYUVQM-LJHODMEESA-N 2-[3-[(3aR,4S,6aS)-4-(dimethylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN([C@H]1CC[C@@H]2CN(C[C@@H]21)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C IAMKMCQYYYUVQM-LJHODMEESA-N 0.000 claims 1
RAIONFDGXQOYOF-RIOSZLGWSA-N 2-[3-[(3aR,4S,6aS)-4-(dimethylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound CN(C)[C@H]1CC[C@H]2[C@@H]1CN(C2)C3=NC=C(N=N3)C4=C(C=C(C=C4)C5=CNN=C5)O.Cl.Cl RAIONFDGXQOYOF-RIOSZLGWSA-N 0.000 claims 1
IAYUEDCPUOUENV-SUMWQHHRSA-N 2-[3-[(3aS,7aR)-1-methyl-3,3a,4,6,7,7a-hexahydro-2H-pyrrolo[3,2-c]pyridin-5-yl]-1,2,4-triazin-6-yl]-5-(5-fluoro-1H-pyrazol-4-yl)phenol Chemical compound CN1CC[C@H]2CN(CC[C@@H]12)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1F IAYUEDCPUOUENV-SUMWQHHRSA-N 0.000 claims 1
JUQUJFJQGMEKOL-YUANJJMISA-N 2-[3-[(3aS,7aR)-1-methyl-3,3a,4,6,7,7a-hexahydro-2H-pyrrolo[3,2-c]pyridin-5-yl]-1,2,4-triazin-6-yl]-5-(5-fluoro-1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound CN1CC[C@@H]2[C@H]1CCN(C2)C3=NC=C(N=N3)C4=C(C=C(C=C4)C5=C(NN=C5)F)O.Cl.Cl JUQUJFJQGMEKOL-YUANJJMISA-N 0.000 claims 1
UONQSHIUWMLZCR-UHFFFAOYSA-N 2-[3-[3-(1-adamantylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CCC(C1)NC12CC3CC(CC(C3)C1)C2 UONQSHIUWMLZCR-UHFFFAOYSA-N 0.000 claims 1
NYOHULCLGPUAPL-UHFFFAOYSA-N 2-[3-[3-(1-adamantylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.Oc1cc(ccc1-c1cnc(nn1)N1CCC(C1)NC12CC3CC(CC(C3)C1)C2)-c1cn[nH]c1 NYOHULCLGPUAPL-UHFFFAOYSA-N 0.000 claims 1
WZZBGCOGRIAKKK-UHFFFAOYSA-N 2-[3-[3-(2-adamantylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CCC(C1)NC1C2CC3CC(C2)CC1C3 WZZBGCOGRIAKKK-UHFFFAOYSA-N 0.000 claims 1
GTYWJZCUEHDKJO-UHFFFAOYSA-N 2-[3-[3-(2-adamantylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.Oc1cc(ccc1-c1cnc(nn1)N1CCC(C1)NC1C2CC3CC(C2)CC1C3)-c1cn[nH]c1 GTYWJZCUEHDKJO-UHFFFAOYSA-N 0.000 claims 1
SNDXZPPVOYHPNT-UHFFFAOYSA-N 2-[3-[3-(2-hydroxyethylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OCCNC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O SNDXZPPVOYHPNT-UHFFFAOYSA-N 0.000 claims 1
JQSVJNYCSYGUSU-UHFFFAOYSA-N 2-[3-[3-(2-methylpropylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CC(CNC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C JQSVJNYCSYGUSU-UHFFFAOYSA-N 0.000 claims 1
MGSGQJPCORKJBB-UHFFFAOYSA-N 2-[3-[3-(cyclopentylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C1(CCCC1)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O MGSGQJPCORKJBB-UHFFFAOYSA-N 0.000 claims 1
MMMQEUVRIQSZCJ-UHFFFAOYSA-N 2-[3-[3-(cyclopentylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CCC(C1)NC1CCCC1)-c1cn[nH]c1 MMMQEUVRIQSZCJ-UHFFFAOYSA-N 0.000 claims 1
ZGRHAIUTHXIGDF-UHFFFAOYSA-N 2-[3-[3-(cyclopropylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C1(CC1)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O ZGRHAIUTHXIGDF-UHFFFAOYSA-N 0.000 claims 1
WIUSGQOBOBPTFK-UHFFFAOYSA-N 2-[3-[3-(dimethylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN(C1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C WIUSGQOBOBPTFK-UHFFFAOYSA-N 0.000 claims 1
SICRLYUBKWVVKG-UHFFFAOYSA-N 2-[3-[3-(ethylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O SICRLYUBKWVVKG-UHFFFAOYSA-N 0.000 claims 1
GDDPNLAKSGTSMQ-UHFFFAOYSA-N 2-[3-[3-(ethylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CCNC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 GDDPNLAKSGTSMQ-UHFFFAOYSA-N 0.000 claims 1
FKPKVANVZUHXQS-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1,2,4-thiadiazol-5-yl)phenol Chemical compound CNC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C1=NC=NS1)O FKPKVANVZUHXQS-UHFFFAOYSA-N 0.000 claims 1
GNVIMVBRAQYCAH-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1,2,4-thiadiazol-5-yl)phenol dihydrochloride Chemical compound Cl.Cl.CNC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1ncns1 GNVIMVBRAQYCAH-UHFFFAOYSA-N 0.000 claims 1
CEHGOSPESNJJPG-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1,3-oxazol-2-yl)phenol Chemical compound CNC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1OC=CN=1)O CEHGOSPESNJJPG-UHFFFAOYSA-N 0.000 claims 1
RVHZPYOZUQZDIW-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1,3-oxazol-2-yl)phenol dihydrochloride Chemical compound Cl.Cl.CNC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1ncco1 RVHZPYOZUQZDIW-UHFFFAOYSA-N 0.000 claims 1
REEDJMNARLFAAD-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1-methylpyrazol-3-yl)phenol Chemical compound CNC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C1=NN(C=C1)C)O REEDJMNARLFAAD-UHFFFAOYSA-N 0.000 claims 1
SCWOVMGNMDPXTB-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1-methylpyrazol-3-yl)phenol dihydrochloride Chemical compound Cl.Cl.CNC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1ccn(C)n1 SCWOVMGNMDPXTB-UHFFFAOYSA-N 0.000 claims 1
BIWCMXHYBHXAKI-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1-methylpyrazol-4-yl)phenol Chemical compound CNC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NN(C=1)C)O BIWCMXHYBHXAKI-UHFFFAOYSA-N 0.000 claims 1
HNGCBLUEWVOFCW-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1-methylpyrazol-4-yl)phenol hydrochloride Chemical compound Cl.CNC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1cnn(C)c1 HNGCBLUEWVOFCW-UHFFFAOYSA-N 0.000 claims 1
XBYIETAMTPAORA-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(2-methyl-1,3-oxazol-5-yl)phenol dihydrochloride Chemical compound Cl.Cl.CNC1CN(CC1)C=1N=NC(=CN1)C1=C(C=C(C=C1)C1=CN=C(O1)C)O XBYIETAMTPAORA-UHFFFAOYSA-N 0.000 claims 1
DXTLPQAEKQREFD-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(2-methyltetrazol-5-yl)phenol trihydrochloride Chemical compound Cl.Cl.Cl.CNC1CN(CC1)C=1N=NC(=CN1)C1=C(C=C(C=C1)C=1N=NN(N1)C)O DXTLPQAEKQREFD-UHFFFAOYSA-N 0.000 claims 1
IMJWYJUHNAWGJG-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(6-methylsulfanylpyrimidin-4-yl)phenol Chemical compound CNC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C1=NC=NC(=C1)SC)O IMJWYJUHNAWGJG-UHFFFAOYSA-N 0.000 claims 1
HOHTWHHAOXMLPQ-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(6-methylsulfanylpyrimidin-4-yl)phenol trihydrochloride Chemical compound Cl.Cl.Cl.CNC1CN(CC1)C=1N=NC(=CN1)C1=C(C=C(C=C1)C1=NC=NC(=C1)SC)O HOHTWHHAOXMLPQ-UHFFFAOYSA-N 0.000 claims 1
PGZRWPHUXYQECF-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(triazol-2-yl)phenol Chemical compound CNC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)N1N=CC=N1)O PGZRWPHUXYQECF-UHFFFAOYSA-N 0.000 claims 1
MCNJFKZWFHFEPM-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-pyrimidin-2-ylphenol Chemical compound CNC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C1=NC=CC=N1)O MCNJFKZWFHFEPM-UHFFFAOYSA-N 0.000 claims 1
YZNPXHHXXNQEPU-UHFFFAOYSA-N 2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-pyrimidin-2-ylphenol dihydrochloride Chemical compound Cl.Cl.CNC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1ncccn1 YZNPXHHXXNQEPU-UHFFFAOYSA-N 0.000 claims 1
FHMLOBOZJYFZLX-UHFFFAOYSA-N 2-[3-[3-(methylaminomethyl)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound N1N=CC(=C1)C1=CC=C(C2=CN=C(N=N2)N2CC(CNC)CC2)C(O)=C1 FHMLOBOZJYFZLX-UHFFFAOYSA-N 0.000 claims 1
LIJFXMYLJBJQRN-UHFFFAOYSA-N 2-[3-[3-(methylaminomethyl)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CNCC1CN(CC1)C=1N=NC(=CN1)C1=C(C=C(C=C1)C=1C=NNC1)O LIJFXMYLJBJQRN-UHFFFAOYSA-N 0.000 claims 1
FXOJZUKQPDKQBQ-UHFFFAOYSA-N 2-[3-[3-(oxan-4-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound O1CCC(CC1)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O FXOJZUKQPDKQBQ-UHFFFAOYSA-N 0.000 claims 1
VZVQEGBOOCGDMW-UHFFFAOYSA-N 2-[3-[3-(oxan-4-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Oc1cc(ccc1-c1cnc(nn1)N1CCC(C1)NC1CCOCC1)-c1cn[nH]c1 VZVQEGBOOCGDMW-UHFFFAOYSA-N 0.000 claims 1
CZAKLFZABOAOAC-UHFFFAOYSA-N 2-[3-[3-(oxetan-3-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound O1CC(C1)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O CZAKLFZABOAOAC-UHFFFAOYSA-N 0.000 claims 1
PLHNNFXUQRMQAF-UHFFFAOYSA-N 2-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CC(C)NC1CCN(C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1 PLHNNFXUQRMQAF-UHFFFAOYSA-N 0.000 claims 1
CHBHGHQUYUVSKC-UHFFFAOYSA-N 2-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol hydrochloride Chemical compound Cl.CC(C)NC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 CHBHGHQUYUVSKC-UHFFFAOYSA-N 0.000 claims 1
KPMRMNZQERYAJI-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)-4-fluoropyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1F)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O KPMRMNZQERYAJI-UHFFFAOYSA-N 0.000 claims 1
VRPDQQCHIYMIPX-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)-4-fluoropyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol hydrochloride Chemical compound Cl.CC(C)(C)NC1CN(CC1F)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 VRPDQQCHIYMIPX-UHFFFAOYSA-N 0.000 claims 1
SSLQNKKGXQHXQR-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)piperidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CCC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O SSLQNKKGXQHXQR-UHFFFAOYSA-N 0.000 claims 1
WMUNPMQDLBEWAH-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)piperidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC(C)(C)NC1CCCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 WMUNPMQDLBEWAH-UHFFFAOYSA-N 0.000 claims 1
CEUBWZFXBHYKEV-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-3-methoxy-5-(1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1OC)C=1C=NNC=1)O CEUBWZFXBHYKEV-UHFFFAOYSA-N 0.000 claims 1
MTTOPERRMHRNTB-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-3-methoxy-5-(1H-pyrazol-4-yl)phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COc1cc(cc(O)c1-c1cnc(nn1)N1CCC(C1)NC(C)(C)C)-c1cn[nH]c1 MTTOPERRMHRNTB-UHFFFAOYSA-N 0.000 claims 1
MWYYKCSMUGGTAH-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1,3-oxazol-2-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1OC=CN=1)O MWYYKCSMUGGTAH-UHFFFAOYSA-N 0.000 claims 1
XHKGBAGQHMOUQD-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1,3-oxazol-2-yl)phenol hydrochloride Chemical compound Cl.CC(C)(C)NC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1ncco1 XHKGBAGQHMOUQD-UHFFFAOYSA-N 0.000 claims 1
XVLPCENXSJBARU-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1-methylindazol-5-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=C2C=NN(C2=CC=1)C)O XVLPCENXSJBARU-UHFFFAOYSA-N 0.000 claims 1
GGOHVVKDPXITOF-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1-methylindazol-5-yl)phenol dihydrochloride Chemical compound Cl.Cl.Cn1ncc2cc(ccc12)-c1ccc(c(O)c1)-c1cnc(nn1)N1CCC(C1)NC(C)(C)C GGOHVVKDPXITOF-UHFFFAOYSA-N 0.000 claims 1
UUSQVLANZCENME-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1-methylpyrazol-3-yl)phenol Chemical compound Cn1ccc(n1)-c1ccc(c(O)c1)-c1cnc(nn1)N1CCC(C1)NC(C)(C)C UUSQVLANZCENME-UHFFFAOYSA-N 0.000 claims 1
MLDFJWIZOFENAK-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1-methylpyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NN(C=1)C)O MLDFJWIZOFENAK-UHFFFAOYSA-N 0.000 claims 1
CLQZJKBWYFKFMF-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1-methyltriazolo[4,5-b]pyridin-5-yl)phenol Chemical compound CN1N=NC2=C1C=CC(=N2)C1=CC(O)=C(C=C1)C1=CN=C(N=N1)N1CCC(C1)NC(C)(C)C CLQZJKBWYFKFMF-UHFFFAOYSA-N 0.000 claims 1
AJPYPUUUHOYAEV-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O AJPYPUUUHOYAEV-UHFFFAOYSA-N 0.000 claims 1
ZWGCPXFIZLMBFU-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(2-methyltetrazol-5-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1N=NN(N=1)C)O ZWGCPXFIZLMBFU-UHFFFAOYSA-N 0.000 claims 1
CWFUSDXAYCUZRR-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(2-methyltetrazol-5-yl)phenol dihydrochloride Chemical compound Cl.Cl.Cn1nnc(n1)-c1ccc(c(O)c1)-c1cnc(nn1)N1CCC(C1)NC(C)(C)C CWFUSDXAYCUZRR-UHFFFAOYSA-N 0.000 claims 1
IVTSINSHNCOZCS-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(4-methylimidazol-1-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)N1C=NC(=C1)C)O IVTSINSHNCOZCS-UHFFFAOYSA-N 0.000 claims 1
NWIRKKRVRKBXLU-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(5-chloro-1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C(=NNC=1)Cl)O NWIRKKRVRKBXLU-UHFFFAOYSA-N 0.000 claims 1
YCKKUIPBMQTRTJ-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(5-chloro-1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CC(C)(C)NC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1Cl YCKKUIPBMQTRTJ-UHFFFAOYSA-N 0.000 claims 1
KBARCCPICPLBAC-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(5-fluoro-1H-pyrazol-4-yl)phenol Chemical compound CC(C)(C)NC1CCN(C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1F KBARCCPICPLBAC-UHFFFAOYSA-N 0.000 claims 1
YPYUQXDHIDTUSP-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(5-methyl-1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C(=NNC=1)C)O YPYUQXDHIDTUSP-UHFFFAOYSA-N 0.000 claims 1
LJCDXBDZUQFSQB-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(5-methyl-1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Cc1[nH]ncc1-c1ccc(c(O)c1)-c1cnc(nn1)N1CCC(C1)NC(C)(C)C LJCDXBDZUQFSQB-UHFFFAOYSA-N 0.000 claims 1
SIJQDWRPERLFCE-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(6-methoxypyrimidin-4-yl)phenol Chemical compound N1=C(C=C(N=C1)C1=CC=C(C2=CN=C(N=N2)N2CCC(NC(C)(C)C)C2)C(O)=C1)OC SIJQDWRPERLFCE-UHFFFAOYSA-N 0.000 claims 1
MLDFJWIZOFENAK-GKOSEXJESA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-[1-(trideuteriomethyl)pyrazol-4-yl]phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NN(C=1)C([2H])([2H])[2H])O MLDFJWIZOFENAK-GKOSEXJESA-N 0.000 claims 1
VNNXTUYFGFIJOV-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-imidazol-1-ylphenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)N1C=NC=C1)O VNNXTUYFGFIJOV-UHFFFAOYSA-N 0.000 claims 1
UMRRXAGJSDHRHA-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-imidazol-1-ylphenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CC(C)(C)NC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-n1ccnc1 UMRRXAGJSDHRHA-UHFFFAOYSA-N 0.000 claims 1
OYIAWNSMOXIBJA-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-pyrimidin-2-ylphenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C1=NC=CC=N1)O OYIAWNSMOXIBJA-UHFFFAOYSA-N 0.000 claims 1
YLPBPDFBPXEMTR-UHFFFAOYSA-N 2-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-pyrimidin-2-ylphenol dihydrochloride Chemical compound Cl.Cl.CC(C)(C)NC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1ncccn1 YLPBPDFBPXEMTR-UHFFFAOYSA-N 0.000 claims 1
HVLLLUICYJYLPI-UHFFFAOYSA-N 2-[3-[3-[(1-methylcyclopropyl)amino]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CC1(CC1)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O HVLLLUICYJYLPI-UHFFFAOYSA-N 0.000 claims 1
NDSAAKUGUXNVCT-UHFFFAOYSA-N 2-[3-[3-[(1-methylcyclopropyl)amino]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CC1(CC1)NC1CN(CC1)C=1N=NC(=CN1)C1=C(C=C(C=C1)C=1C=NNC1)O NDSAAKUGUXNVCT-UHFFFAOYSA-N 0.000 claims 1
CAZRHJOVYYXPSL-UHFFFAOYSA-N 2-[3-[3-[(3,3-difluorocyclopentyl)amino]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound Oc1cc(ccc1-c1cnc(nn1)N1CCC(C1)NC1CCC(F)(F)C1)-c1cn[nH]c1 CAZRHJOVYYXPSL-UHFFFAOYSA-N 0.000 claims 1
GOQFFXQBNJORKV-UHFFFAOYSA-N 2-[3-[3-[(3-fluorocyclopentyl)amino]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CCC(C1)NC1CCC(F)C1 GOQFFXQBNJORKV-UHFFFAOYSA-N 0.000 claims 1
YYWNWJXOHCEECN-UHFFFAOYSA-N 2-[3-[3-[(cyclobutylamino)methyl]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C1(CCC1)NCC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O YYWNWJXOHCEECN-UHFFFAOYSA-N 0.000 claims 1
ZZCRTPMXGHXJSC-UHFFFAOYSA-N 2-[3-[3-[(cyclobutylamino)methyl]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.C1(CCC1)NCC1CN(CC1)C=1N=NC(=CN1)C1=C(C=C(C=C1)C=1C=NNC1)O ZZCRTPMXGHXJSC-UHFFFAOYSA-N 0.000 claims 1
PSEKHDJBMSJDPU-UHFFFAOYSA-N 2-[3-[3-[(cyclopentylamino)methyl]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound OC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CCC(CNC2CCCC2)C1 PSEKHDJBMSJDPU-UHFFFAOYSA-N 0.000 claims 1
HJMKAWFYVWOHQE-UHFFFAOYSA-N 2-[3-[3-[(cyclopentylamino)methyl]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.C1(CCCC1)NCC1CN(CC1)C=1N=NC(=CN1)C1=C(C=C(C=C1)C=1C=NNC1)O HJMKAWFYVWOHQE-UHFFFAOYSA-N 0.000 claims 1
KTDGEAYLMRCIQJ-UHFFFAOYSA-N 2-[3-[3-[(cyclopropylamino)methyl]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound N=1NC=C(C=1)C1=CC=C(C2=CN=C(N=N2)N2CCC(CNC3CC3)C2)C(O)=C1 KTDGEAYLMRCIQJ-UHFFFAOYSA-N 0.000 claims 1
NYURIVSVXGJNSW-UHFFFAOYSA-N 2-[3-[3-[(dimethylamino)methyl]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound N1C=C(C2=CC=C(C3=CN=C(N4CCC(CN(C)C)C4)N=N3)C(O)=C2)C=N1 NYURIVSVXGJNSW-UHFFFAOYSA-N 0.000 claims 1
ZSIINFLADFCMBR-UHFFFAOYSA-N 2-[3-[3-[(dimethylamino)methyl]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CN(C)CC1CN(CC1)C=1N=NC(=CN1)C1=C(C=C(C=C1)C=1C=NNC1)O ZSIINFLADFCMBR-UHFFFAOYSA-N 0.000 claims 1
RYTOKFYVQPFHET-UHFFFAOYSA-N 2-[3-[3-[(tert-butylamino)methyl]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound N1N=CC(=C1)C1=CC=C(C2=CN=C(N=N2)N2CCC(CNC(C)(C)C)C2)C(O)=C1 RYTOKFYVQPFHET-UHFFFAOYSA-N 0.000 claims 1
YQUDFQCYKDLCEO-UHFFFAOYSA-N 2-[3-[4-(tert-butylamino)-2-methylpyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CC(N(C1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C YQUDFQCYKDLCEO-UHFFFAOYSA-N 0.000 claims 1
XWLMPBOIEIOSKB-UHFFFAOYSA-N 2-[3-[4-(tert-butylamino)piperidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CCN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O XWLMPBOIEIOSKB-UHFFFAOYSA-N 0.000 claims 1
SYWHCNUQDZDLIG-UHFFFAOYSA-N 2-[3-[4-(tert-butylamino)piperidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC(C)(C)NC1CCN(CC1)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 SYWHCNUQDZDLIG-UHFFFAOYSA-N 0.000 claims 1
SPUUSLXEIQIVER-JTQLQIEISA-N 2-[3-[[(2S)-2-aminopropyl]-methylamino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C[C@H](N)CN(C)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1 SPUUSLXEIQIVER-JTQLQIEISA-N 0.000 claims 1
ZBLHLSAKRWDMSY-XRIOVQLTSA-N 2-[3-[[(2S)-2-aminopropyl]-methylamino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.C[C@H](N)CN(C)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 ZBLHLSAKRWDMSY-XRIOVQLTSA-N 0.000 claims 1
JZVWLFOAZASBMO-CRAIPNDOSA-N 2-[3-[[(3R,4R)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound F[C@H]1C(NC(C[C@H]1NC=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)(C)C)(C)C JZVWLFOAZASBMO-CRAIPNDOSA-N 0.000 claims 1
QHBAPJSQFSZDCL-KGLIPLIRSA-N 2-[3-[[(3R,4S)-3-fluoropiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound F[C@@H]1CNCC[C@@H]1NC=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O QHBAPJSQFSZDCL-KGLIPLIRSA-N 0.000 claims 1
JPGGVPRJOMAOGD-BQFBZIMZSA-N 2-[3-[[(3R,4S)-3-fluoropiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound C1CNC[C@H]([C@H]1NC2=NC=C(N=N2)C3=C(C=C(C=C3)C4=CNN=C4)O)F.Cl.Cl JPGGVPRJOMAOGD-BQFBZIMZSA-N 0.000 claims 1
QIUMREZZUPSWKC-BBRMVZONSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1,2,4-thiadiazol-5-yl)phenol Chemical compound CC1(C)C[C@H](NC2=NC=C(N=N2)C2=C(O)C=C(C=C2)C2=NC=NS2)[C@H](F)C(C)(C)N1 QIUMREZZUPSWKC-BBRMVZONSA-N 0.000 claims 1
XBSSXUQVQUBXKT-LINSIKMZSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1,2,4-thiadiazol-5-yl)phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1(C)C[C@H](Nc2ncc(nn2)-c2ccc(cc2O)-c2ncns2)[C@H](F)C(C)(C)N1 XBSSXUQVQUBXKT-LINSIKMZSA-N 0.000 claims 1
JIXPMXJNQZXMPW-YOEHRIQHSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1,3-oxazol-2-yl)phenol Chemical compound CC1(C)C[C@H](NC2=NC=C(N=N2)C2=C(O)C=C(C=C2)C2=NC=CO2)[C@H](F)C(C)(C)N1 JIXPMXJNQZXMPW-YOEHRIQHSA-N 0.000 claims 1
SYKKRKXNHINNPC-RVXRQPKJSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1,3-oxazol-2-yl)phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1(C)C[C@H](Nc2ncc(nn2)-c2ccc(cc2O)-c2ncco2)[C@H](F)C(C)(C)N1 SYKKRKXNHINNPC-RVXRQPKJSA-N 0.000 claims 1
DHDWGOCZNSBLAN-CVDCTZTESA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1-methylindazol-5-yl)phenol Chemical compound CN1N=CC2=C1C=CC(=C2)C1=CC(O)=C(C=C1)C1=CN=C(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)N=N1 DHDWGOCZNSBLAN-CVDCTZTESA-N 0.000 claims 1
TXDNFAAYZVPJML-HXTKCBNGSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1-methylindazol-5-yl)phenol dihydrochloride Chemical compound Cl.Cl.Cn1ncc2cc(ccc12)-c1ccc(c(O)c1)-c1cnc(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)nn1 TXDNFAAYZVPJML-HXTKCBNGSA-N 0.000 claims 1
UJXRSKVCIDPENV-LPHOPBHVSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1-methylpyrazol-3-yl)phenol Chemical compound CN1C=CC(=N1)C1=CC(O)=C(C=C1)C1=CN=C(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)N=N1 UJXRSKVCIDPENV-LPHOPBHVSA-N 0.000 claims 1
BMORGZTZLMAHFK-VBKBRSQCSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1-methylpyrazol-3-yl)phenol dihydrochloride Chemical compound Cl.Cl.Cn1ccc(n1)-c1ccc(c(O)c1)-c1cnc(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)nn1 BMORGZTZLMAHFK-VBKBRSQCSA-N 0.000 claims 1
SISBKYXCVOUUTN-LPHOPBHVSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1-methylpyrazol-4-yl)phenol Chemical compound CN1C=C(C=N1)C1=CC(O)=C(C=C1)C1=CN=C(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)N=N1 SISBKYXCVOUUTN-LPHOPBHVSA-N 0.000 claims 1
GZOYDHQPWIGCRD-RXVVDRJESA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1-methylpyrazolo[3,4-b]pyridin-5-yl)phenol Chemical compound Cn1ncc2cc(cnc12)-c1ccc(c(O)c1)-c1cnc(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)nn1 GZOYDHQPWIGCRD-RXVVDRJESA-N 0.000 claims 1
NFFGBAOSTIKDLK-AEOSXFHFSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1-methylpyrazolo[3,4-b]pyridin-5-yl)phenol dihydrochloride Chemical compound Cl.Cl.Cn1ncc2cc(cnc12)-c1ccc(c(O)c1)-c1cnc(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)nn1 NFFGBAOSTIKDLK-AEOSXFHFSA-N 0.000 claims 1
JZVWLFOAZASBMO-YJBOKZPZSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CC1(C)C[C@H](NC2=NC=C(N=N2)C2=C(O)C=C(C=C2)C2=CNN=C2)[C@H](F)C(C)(C)N1 JZVWLFOAZASBMO-YJBOKZPZSA-N 0.000 claims 1
KUPLILKPQGGSNY-BBRMVZONSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(2-methyltetrazol-5-yl)phenol Chemical compound CN1N=NC(=N1)C1=CC(O)=C(C=C1)C1=CN=C(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)N=N1 KUPLILKPQGGSNY-BBRMVZONSA-N 0.000 claims 1
LBXOJGVOHRLYPL-LINSIKMZSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(2-methyltetrazol-5-yl)phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.Cn1nnc(n1)-c1ccc(c(O)c1)-c1cnc(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)nn1 LBXOJGVOHRLYPL-LINSIKMZSA-N 0.000 claims 1
SXYKIQWEALXZST-KSSFIOAISA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(2-methyltriazol-4-yl)phenol Chemical compound CN1N=CC(=N1)C1=CC(O)=C(C=C1)C1=CN=C(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)N=N1 SXYKIQWEALXZST-KSSFIOAISA-N 0.000 claims 1
DUZCTBHNIXOGDD-DJKAKHFESA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(2-methyltriazol-4-yl)phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.Cn1ncc(n1)-c1ccc(c(O)c1)-c1cnc(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)nn1 DUZCTBHNIXOGDD-DJKAKHFESA-N 0.000 claims 1
TWWULYGKVMJXJT-GUYCJALGSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(2H-triazol-4-yl)phenol Chemical compound CC1(C)C[C@H](Nc2ncc(nn2)-c2ccc(cc2O)-c2cn[nH]n2)[C@H](F)C(C)(C)N1 TWWULYGKVMJXJT-GUYCJALGSA-N 0.000 claims 1
LVCRMQDBYPAAJE-ZMQOMOPGSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(2H-triazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CC1(C)C[C@H](Nc2ncc(nn2)-c2ccc(cc2O)-c2cn[nH]n2)[C@H](F)C(C)(C)N1 LVCRMQDBYPAAJE-ZMQOMOPGSA-N 0.000 claims 1
SLAMJCWXDQJVSY-LPHOPBHVSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(4-methylimidazol-1-yl)phenol Chemical compound CC1=CN(C=N1)C1=CC(O)=C(C=C1)C1=CN=C(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)N=N1 SLAMJCWXDQJVSY-LPHOPBHVSA-N 0.000 claims 1
ODIBMQNQFIEUSU-VBKBRSQCSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(4-methylimidazol-1-yl)phenol dihydrochloride Chemical compound Cl.Cl.Cc1cn(cn1)-c1ccc(c(O)c1)-c1cnc(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)nn1 ODIBMQNQFIEUSU-VBKBRSQCSA-N 0.000 claims 1
OLCSMVQGEFCNJY-JXFKEZNVSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(6-methoxypyrimidin-4-yl)phenol Chemical compound COC1=NC=NC(=C1)C1=CC(O)=C(C=C1)C1=CN=C(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)N=N1 OLCSMVQGEFCNJY-JXFKEZNVSA-N 0.000 claims 1
GXQFYHORDQMJIK-XXRBRTKDSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(6-methoxypyrimidin-4-yl)phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COc1cc(ncn1)-c1ccc(c(O)c1)-c1cnc(N[C@H]2CC(C)(C)NC(C)(C)[C@H]2F)nn1 GXQFYHORDQMJIK-XXRBRTKDSA-N 0.000 claims 1
OZKUYXIXGDLMRU-KKSFZXQISA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-imidazo[1,2-a]pyrazin-6-ylphenol Chemical compound CC1(C)C[C@H](NC2=NC=C(N=N2)C2=C(O)C=C(C=C2)C2=CN3C=CN=C3C=N2)[C@H](F)C(C)(C)N1 OZKUYXIXGDLMRU-KKSFZXQISA-N 0.000 claims 1
OKAJZJZCAPWSMW-UWJYYQICSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-imidazo[1,2-b]pyridazin-6-ylphenol Chemical compound CC1(C)C[C@H](NC2=NC=C(N=N2)C2=C(O)C=C(C=C2)C2=NN3C=CN=C3C=C2)[C@H](F)C(C)(C)N1 OKAJZJZCAPWSMW-UWJYYQICSA-N 0.000 claims 1
QKOJPVYFIIMSPR-BGESAIIZSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-imidazo[1,2-b]pyridazin-6-ylphenol dihydrochloride Chemical compound Cl.Cl.CC1(C)C[C@H](Nc2ncc(nn2)-c2ccc(cc2O)-c2ccc3nccn3n2)[C@H](F)C(C)(C)N1 QKOJPVYFIIMSPR-BGESAIIZSA-N 0.000 claims 1
ZPYNSCJPVKATOY-YJBOKZPZSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-imidazol-1-ylphenol Chemical compound CC1(C)C[C@H](NC2=NC=C(N=N2)C2=C(O)C=C(C=C2)N2C=CN=C2)[C@H](F)C(C)(C)N1 ZPYNSCJPVKATOY-YJBOKZPZSA-N 0.000 claims 1
BVEKXRYOCXTMHH-WQPBPYDNSA-N 2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-imidazol-1-ylphenol dihydrochloride Chemical compound Cl.Cl.CC1(C)C[C@H](Nc2ncc(nn2)-c2ccc(cc2O)-n2ccnc2)[C@H](F)C(C)(C)N1 BVEKXRYOCXTMHH-WQPBPYDNSA-N 0.000 claims 1
BVUNWHBQBLTSJR-ICSRJNTNSA-N 2-[3-[[(3S,4S)-3-methoxy-2,2,6,6-tetramethylpiperidin-4-yl]-methylamino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CO[C@@H]1C(NC(C[C@@H]1N(C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C)(C)C)(C)C BVUNWHBQBLTSJR-ICSRJNTNSA-N 0.000 claims 1
QVSCXUWJTLTQNF-OINVMNEBSA-N 2-[3-[[(3S,4S)-3-methoxy-2,2,6,6-tetramethylpiperidin-4-yl]-methylamino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CO[C@H]1[C@H](CC(C)(C)NC1(C)C)N(C)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 QVSCXUWJTLTQNF-OINVMNEBSA-N 0.000 claims 1
WRYXZECRTZTICJ-LPHOPBHVSA-N 2-[3-[[(3S,4S)-3-methoxy-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CO[C@H]1[C@H](CC(C)(C)NC1(C)C)NC1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1 WRYXZECRTZTICJ-LPHOPBHVSA-N 0.000 claims 1
NJWCEQKEJXVFGH-UHFFFAOYSA-N 2-[3-[methyl(piperidin-3-yl)amino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN(C1CCCNC1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1 NJWCEQKEJXVFGH-UHFFFAOYSA-N 0.000 claims 1
XKSLBKQETONBFK-UHFFFAOYSA-N 2-[3-[methyl(piperidin-3-yl)amino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CN(C1CCCNC1)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 XKSLBKQETONBFK-UHFFFAOYSA-N 0.000 claims 1
UNDVPHYYRCRWIE-UHFFFAOYSA-N 2-[3-[methyl(piperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN(C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C1CCNCC1 UNDVPHYYRCRWIE-UHFFFAOYSA-N 0.000 claims 1
XIOSCSZUMRUYDZ-UHFFFAOYSA-N 2-[3-[methyl(piperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CN(C1CCNCC1)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 XIOSCSZUMRUYDZ-UHFFFAOYSA-N 0.000 claims 1
VAYDUOFABLAEKM-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-(1-methyltriazolo[4,5-b]pyridin-5-yl)phenol Chemical compound CN(C=1N=NC(=CN=1)C1=C(C=C(C=C1)C1=CC=C2C(=N1)N=NN2C)O)C1CC(NC(C1)(C)C)(C)C VAYDUOFABLAEKM-UHFFFAOYSA-N 0.000 claims 1
ULQQYVAROGLUIK-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-(triazolo[1,5-a]pyridin-5-yl)phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC2=CN=NN2C=C1 ULQQYVAROGLUIK-UHFFFAOYSA-N 0.000 claims 1
AHBRKMXCGQTDHW-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-(triazolo[1,5-a]pyridin-5-yl)phenol dihydrochloride Chemical compound Cl.Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1ccn2nncc2c1 AHBRKMXCGQTDHW-UHFFFAOYSA-N 0.000 claims 1
KVGVJDUCKDJLDS-VPYROQPTSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-[1-(trideuteriomethyl)pyrazol-4-yl]phenol Chemical compound [2H]C([2H])([2H])N1C=C(C=N1)C1=CC(O)=C(C=C1)C1=CN=C(N=N1)N(C)C1CC(C)(C)NC(C)(C)C1 KVGVJDUCKDJLDS-VPYROQPTSA-N 0.000 claims 1
YZGFSZQMTMLWQB-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyrazin-2-ylphenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CN=CC=N1 YZGFSZQMTMLWQB-UHFFFAOYSA-N 0.000 claims 1
BGCMHDWUWCJULN-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyridazin-3-ylphenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1cccnn1 BGCMHDWUWCJULN-UHFFFAOYSA-N 0.000 claims 1
YQBHBOVNFQKOGV-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyridazin-4-ylphenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1ccnnc1 YQBHBOVNFQKOGV-UHFFFAOYSA-N 0.000 claims 1
WXRBDWCCYGIMPG-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyridazin-4-ylphenol dihydrochloride Chemical compound Cl.Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1ccnnc1 WXRBDWCCYGIMPG-UHFFFAOYSA-N 0.000 claims 1
XIBNSPIDEBJNEG-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyridin-2-ylphenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NC=CC=C1 XIBNSPIDEBJNEG-UHFFFAOYSA-N 0.000 claims 1
GINIIZKQAMMHMI-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyridin-3-ylphenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1cccnc1 GINIIZKQAMMHMI-UHFFFAOYSA-N 0.000 claims 1
YSDPIAJUGTXJMF-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyridin-4-ylphenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC=NC=C1 YSDPIAJUGTXJMF-UHFFFAOYSA-N 0.000 claims 1
LBFONZSBFXSDAQ-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyrimidin-2-ylphenol Chemical compound CN(C=1N=NC(=CN=1)C1=C(C=C(C=C1)C1=NC=CC=N1)O)C1CC(NC(C1)(C)C)(C)C LBFONZSBFXSDAQ-UHFFFAOYSA-N 0.000 claims 1
AXKRVBCAKOGMQV-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyrimidin-4-ylphenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC=NC=N1 AXKRVBCAKOGMQV-UHFFFAOYSA-N 0.000 claims 1
VVMWKQKCMBYDMW-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-quinolin-6-ylphenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC=C2N=CC=CC2=C1 VVMWKQKCMBYDMW-UHFFFAOYSA-N 0.000 claims 1
CULMDJHLYUWYET-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-quinolin-6-ylphenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1ccc2ncccc2c1 CULMDJHLYUWYET-UHFFFAOYSA-N 0.000 claims 1
DWHWJYPRNRKTMP-UHFFFAOYSA-N 2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-thiophen-2-ylphenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC=CS1 DWHWJYPRNRKTMP-UHFFFAOYSA-N 0.000 claims 1
NWSDGCVODQXXMR-VPYROQPTSA-N 2-[6-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]-5-[1-(trideuteriomethyl)pyrazol-4-yl]phenol Chemical compound C(N1N=CC(=C1)C=1C=CC(=C(C=1)O)C=1N=NC(=CN=1)NC1CC(NC(C1)(C)C)(C)C)([2H])([2H])[2H] NWSDGCVODQXXMR-VPYROQPTSA-N 0.000 claims 1
XHXNJXDTNZOAPQ-UHFFFAOYSA-N 2-[6-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-3-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C1=CN=C(N=N1)C1=C(C=C(C=C1)C=1C=NNC=1)O XHXNJXDTNZOAPQ-UHFFFAOYSA-N 0.000 claims 1
NHRQQMQIMOZVHV-UHFFFAOYSA-N 2-[6-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-3-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CC(C)(C)NC1CCN(C1)c1cnc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 NHRQQMQIMOZVHV-UHFFFAOYSA-N 0.000 claims 1
XFRDHRYTHOVQIU-UHFFFAOYSA-N 2-[6-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-3-yl]-5-(5-fluoro-1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C1=CN=C(N=N1)C1=C(C=C(C=C1)C=1C(=NNC=1)F)O XFRDHRYTHOVQIU-UHFFFAOYSA-N 0.000 claims 1
WLSQOKCLWNIWOH-UHFFFAOYSA-N 2-[6-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-3-yl]-5-(5-fluoro-1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CC(C)(C)NC1CCN(C1)c1cnc(nn1)-c1ccc(cc1O)-c1cn[nH]c1F WLSQOKCLWNIWOH-UHFFFAOYSA-N 0.000 claims 1
JXRHIUDJKVASTJ-VPYROQPTSA-N 2-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]-5-[1-(trideuteriomethyl)pyrazol-4-yl]phenol Chemical compound C(N1N=CC(=C1)C=1C=CC(=C(C=1)O)C=1N=NC(=CN=1)N(C1CC(NC(C1)(C)C)(C)C)C)([2H])([2H])[2H] JXRHIUDJKVASTJ-VPYROQPTSA-N 0.000 claims 1
XCDPNDWSQOBCSM-UHFFFAOYSA-N 2-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]-5-pyrazin-2-ylphenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=CN=C(N=N1)C1=C(O)C=C(C=C1)C1=CN=CC=N1 XCDPNDWSQOBCSM-UHFFFAOYSA-N 0.000 claims 1
OWLRHKMYLMFFKD-UHFFFAOYSA-N 2-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]-5-pyridin-2-ylphenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=CN=C(N=N1)C1=C(O)C=C(C=C1)C1=NC=CC=C1 OWLRHKMYLMFFKD-UHFFFAOYSA-N 0.000 claims 1
CGYVWZBGCQAWTB-UHFFFAOYSA-N 2-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]-5-pyridin-3-ylphenol Chemical compound C1=CC(C2=CC(=C(C=C2)C2=NC=C(N(C3CC(NC(C3)(C)C)(C)C)C)N=N2)O)=CN=C1 CGYVWZBGCQAWTB-UHFFFAOYSA-N 0.000 claims 1
DVRGMDVMQMKIQX-UHFFFAOYSA-N 2-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]-5-pyridin-4-ylphenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=CN=C(N=N1)C1=C(O)C=C(C=C1)C1=CC=NC=C1 DVRGMDVMQMKIQX-UHFFFAOYSA-N 0.000 claims 1
YJTMCKGSNUJZCX-UHFFFAOYSA-N 2-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]-5-pyrimidin-2-ylphenol Chemical compound N1=CC=CN=C1C1=CC=C(C2=NC=C(N=N2)N(C2CC(NC(C)(C)C2)(C)C)C)C(O)=C1 YJTMCKGSNUJZCX-UHFFFAOYSA-N 0.000 claims 1
OQHQOOLVQDEIGL-UHFFFAOYSA-N 2-methyl-2,7-diazaspiro[4.4]nonane Chemical compound C1N(C)CCC11CNCC1 OQHQOOLVQDEIGL-UHFFFAOYSA-N 0.000 claims 1
SIGWPXIXDIJJOP-UHFFFAOYSA-N 3-(1-methylpyrazol-3-yl)-6-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]benzene-1,2-diol Chemical compound C1=CN(N=C1C1=CC=C(C2=CN=C(N=N2)N(C2CC(C)(NC(C2)(C)C)C)C)C(O)=C1O)C SIGWPXIXDIJJOP-UHFFFAOYSA-N 0.000 claims 1
JPKXLIRUIIDDDA-UHFFFAOYSA-N 3-amino-6-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]-4-methyl-1H-pyridin-2-one Chemical compound NC=1C(=NC(=CC=1C)C1=CC(=C(C=C1)C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C)O)O JPKXLIRUIIDDDA-UHFFFAOYSA-N 0.000 claims 1
ZGRIZNKAVPPURY-UHFFFAOYSA-N 4-[3-hydroxy-4-[3-(7-methyl-2,7-diazaspiro[3.5]nonan-2-yl)-1,2,4-triazin-6-yl]phenyl]-1-methylpyridin-2-one Chemical compound OC=1C=C(C=CC=1C1=CN=C(N=N1)N1CC2(C1)CCN(CC2)C)C1=CC(N(C=C1)C)=O ZGRIZNKAVPPURY-UHFFFAOYSA-N 0.000 claims 1
NWOJBNQPULQMLE-UHFFFAOYSA-N 4-[3-hydroxy-4-[3-(7-methyl-2,7-diazaspiro[3.5]nonan-2-yl)-1,2,4-triazin-6-yl]phenyl]-1-methylpyridin-2-one hydrochloride Chemical compound Cl.OC=1C=C(C=CC1C1=CN=C(N=N1)N1CC2(C1)CCN(CC2)C)C2=CC(N(C=C2)C)=O NWOJBNQPULQMLE-UHFFFAOYSA-N 0.000 claims 1
XFAWBYKAABUOSH-UHFFFAOYSA-N 4-[3-hydroxy-4-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenyl]-1-methylpyridin-2-one Chemical compound OC=1C=C(C=CC=1C1=CN=C(N=N1)N1CC(CC1)NC(C)C)C1=CC(N(C=C1)C)=O XFAWBYKAABUOSH-UHFFFAOYSA-N 0.000 claims 1
DGNSWWBYFTVYOX-UHFFFAOYSA-N 4-[3-hydroxy-4-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenyl]-1-methylpyridin-2-one hydrochloride Chemical compound Cl.CC(C)NC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1ccn(C)c(=O)c1 DGNSWWBYFTVYOX-UHFFFAOYSA-N 0.000 claims 1
WBWVRECVZZJCRY-UHFFFAOYSA-N 4-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]-1-methylpyridin-2-one Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC(=O)N(C)C=C1 WBWVRECVZZJCRY-UHFFFAOYSA-N 0.000 claims 1
VKMXNMVKZGEFRP-UHFFFAOYSA-N 4-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]-1H-pyrazole-5-carbonitrile Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=C(NN=C1)C#N VKMXNMVKZGEFRP-UHFFFAOYSA-N 0.000 claims 1
RGLHGBQSTBWRTI-UHFFFAOYSA-N 4-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]-2-methylpyrazole-3-carbonitrile Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=C(C#N)N(C)N=C1 RGLHGBQSTBWRTI-UHFFFAOYSA-N 0.000 claims 1
IZZPCQIUWUHWGH-UHFFFAOYSA-N 4-[3-hydroxy-4-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]phenyl]-1H-pyrazole-5-carbonitrile Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=CN=C(N=N1)C1=C(O)C=C(C=C1)C1=C(NN=C1)C#N IZZPCQIUWUHWGH-UHFFFAOYSA-N 0.000 claims 1
ZADSTFXIMJZXOO-UHFFFAOYSA-N 4-[3-hydroxy-4-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]phenyl]-2-methylpyrazole-3-carbonitrile Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=CN=C(N=N1)C1=C(O)C=C(C=C1)C1=C(C#N)N(C)N=C1 ZADSTFXIMJZXOO-UHFFFAOYSA-N 0.000 claims 1
PYMNETVRMIRSHC-UHFFFAOYSA-N 4-[4-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-3-hydroxyphenyl]-1H-pyrazole-5-carbonitrile Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C(=NNC=1)C#N)O PYMNETVRMIRSHC-UHFFFAOYSA-N 0.000 claims 1
UQYDTJFWESHTSX-UHFFFAOYSA-N 4-[4-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-3-hydroxyphenyl]-1H-pyrazole-5-carbonitrile dihydrochloride Chemical compound Cl.Cl.C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN1)C1=C(C=C(C=C1)C=1C(=NNC1)C#N)O UQYDTJFWESHTSX-UHFFFAOYSA-N 0.000 claims 1
RREFRGLVXSRGLE-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC2=C(OCO2)C=C1 RREFRGLVXSRGLE-UHFFFAOYSA-N 0.000 claims 1
LYDMBAWOQAVEDT-UHFFFAOYSA-N 5-(1,3-oxazol-2-yl)-2-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol Chemical compound O1C(=NC=C1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)N1CC(CC1)NC(C)C LYDMBAWOQAVEDT-UHFFFAOYSA-N 0.000 claims 1
AINAFLFPIKGSCC-UHFFFAOYSA-N 5-(1,5-dimethylpyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN1N=CC(=C1C)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C AINAFLFPIKGSCC-UHFFFAOYSA-N 0.000 claims 1
FYWUSPASBJRTDH-UHFFFAOYSA-N 5-(1,5-dimethylpyrazol-4-yl)-2-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]phenol Chemical compound CN1N=CC(=C1C)C=1C=CC(=C(C=1)O)C=1N=NC(=CN=1)N(C1CC(NC(C1)(C)C)(C)C)C FYWUSPASBJRTDH-UHFFFAOYSA-N 0.000 claims 1
XNBUGIJGMHRKLR-UHFFFAOYSA-N 5-(1-cyclopropylpyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CN(N=C1)C1CC1 XNBUGIJGMHRKLR-UHFFFAOYSA-N 0.000 claims 1
QIEFGFAMKVXAMT-UHFFFAOYSA-N 5-(1-cyclopropylpyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1cnn(c1)C1CC1 QIEFGFAMKVXAMT-UHFFFAOYSA-N 0.000 claims 1
FVYFFAPOWGRBPY-UHFFFAOYSA-N 5-(1-methylbenzimidazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC=C2N(C)C=NC2=C1 FVYFFAPOWGRBPY-UHFFFAOYSA-N 0.000 claims 1
PYWGUVLZNSNLTO-UHFFFAOYSA-N 5-(1-methylbenzotriazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC=C2N(C)N=NC2=C1 PYWGUVLZNSNLTO-UHFFFAOYSA-N 0.000 claims 1
NWSAMQQOLQCUJP-UHFFFAOYSA-N 5-(1-methylimidazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CN(C)C=N1 NWSAMQQOLQCUJP-UHFFFAOYSA-N 0.000 claims 1
RITBTHZJBQZWAR-UHFFFAOYSA-N 5-(1-methylimidazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CN1C=NC(=C1)C=1C=CC(=C(C1)O)C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C RITBTHZJBQZWAR-UHFFFAOYSA-N 0.000 claims 1
QSGCFAJPAIASSU-UHFFFAOYSA-N 5-(1-methylindazol-5-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound N1(C)C2=CC=C(C3=CC=C(C4=CN=C(N=N4)NC4CC(NC(C4)(C)C)(C)C)C(O)=C3)C=C2C=N1 QSGCFAJPAIASSU-UHFFFAOYSA-N 0.000 claims 1
RCEDBSJKNMNSON-UHFFFAOYSA-N 5-(1-methylindazol-5-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol trihydrochloride Chemical compound Cl.Cl.Cl.CN1N=CC2=CC(=CC=C12)C=1C=CC(=C(C1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C RCEDBSJKNMNSON-UHFFFAOYSA-N 0.000 claims 1
WEDCLXPEYKMDLQ-UHFFFAOYSA-N 5-(1-methylindazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC2=C(C=C1)N(C)N=C2 WEDCLXPEYKMDLQ-UHFFFAOYSA-N 0.000 claims 1
OWDHUIORMYURHT-UHFFFAOYSA-N 5-(1-methylpyrazol-3-yl)-2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)oxy-1,2,4-triazin-6-yl]phenol Chemical compound CN1N=C(C=C1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)OC1CC(NC(C1)(C)C)(C)C OWDHUIORMYURHT-UHFFFAOYSA-N 0.000 claims 1
UHCPNQLAGZAGSA-UHFFFAOYSA-N 5-(1-methylpyrazol-3-yl)-2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)oxy-1,2,4-triazin-6-yl]phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.Cn1ccc(n1)-c1ccc(c(O)c1)-c1cnc(OC2CC(C)(C)NC(C)(C)C2)nn1 UHCPNQLAGZAGSA-UHFFFAOYSA-N 0.000 claims 1
BZBMRMFUSXOJFZ-UHFFFAOYSA-N 5-(1-methylpyrazol-3-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN1N=C(C=C1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C BZBMRMFUSXOJFZ-UHFFFAOYSA-N 0.000 claims 1
VKUASDMPTSARJE-UHFFFAOYSA-N 5-(1-methylpyrazol-3-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NN(C)C=C1 VKUASDMPTSARJE-UHFFFAOYSA-N 0.000 claims 1
LGBYUCPYBCPVMO-UHFFFAOYSA-N 5-(1-methylpyrazol-3-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CN1N=C(C=C1)C=1C=CC(=C(C1)O)C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C LGBYUCPYBCPVMO-UHFFFAOYSA-N 0.000 claims 1
TWAQQEOIIQZKOT-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C TWAQQEOIIQZKOT-UHFFFAOYSA-N 0.000 claims 1
KVGVJDUCKDJLDS-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NN(C=1)C)O)C1CC(NC(C1)(C)C)(C)C KVGVJDUCKDJLDS-UHFFFAOYSA-N 0.000 claims 1
YISQCEKJTWVFTL-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound Cl.Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1cnn(C)c1 YISQCEKJTWVFTL-UHFFFAOYSA-N 0.000 claims 1
KOPGWTHDJUUGCP-UHFFFAOYSA-N 5-(1-methylpyrazolo[3,4-b]pyridin-5-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound Cn1ncc2cc(cnc12)-c1ccc(c(O)c1)-c1cnc(NC2CC(C)(C)NC(C)(C)C2)nn1 KOPGWTHDJUUGCP-UHFFFAOYSA-N 0.000 claims 1
XYADFKNQKXLYJI-UHFFFAOYSA-N 5-(1-methylpyrazolo[3,4-b]pyridin-5-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol trihydrochloride Chemical compound Cl.Cl.Cl.CN1N=CC=2C1=NC=C(C2)C=2C=CC(=C(C2)O)C2=CN=C(N=N2)NC2CC(NC(C2)(C)C)(C)C XYADFKNQKXLYJI-UHFFFAOYSA-N 0.000 claims 1
ZKYKVESLUGXALS-UHFFFAOYSA-N 5-(1-methylpyrazolo[3,4-b]pyridin-5-yl)-2-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol Chemical compound CN1N=CC=2C1=NC=C(C=2)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)N1CC(CC1)NC(C)C ZKYKVESLUGXALS-UHFFFAOYSA-N 0.000 claims 1
GCBJHNMZASCIMR-UHFFFAOYSA-N 5-(1-methylpyrazolo[3,4-b]pyridin-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC2=C(N=C1)N(C)N=C2 GCBJHNMZASCIMR-UHFFFAOYSA-N 0.000 claims 1
RDFCGXQDFGNOIB-UHFFFAOYSA-N 5-(1-methylpyrazolo[3,4-c]pyridin-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1cc2cnn(C)c2cn1 RDFCGXQDFGNOIB-UHFFFAOYSA-N 0.000 claims 1
IOANDIWFHWUYPS-UHFFFAOYSA-N 5-(1-methylpyrazolo[3,4-c]pyridin-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound Cl.Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1cc2cnn(C)c2cn1 IOANDIWFHWUYPS-UHFFFAOYSA-N 0.000 claims 1
VNYDSVJCHGEVKM-UHFFFAOYSA-N 5-(1-methylpyrazolo[4,3-b]pyridin-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NC2=C(C=C1)N(C)N=C2 VNYDSVJCHGEVKM-UHFFFAOYSA-N 0.000 claims 1
PZODBDHTCASPNJ-UHFFFAOYSA-N 5-(1-methylpyrazolo[4,3-b]pyridin-5-yl)-2-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=CN=C(N=N1)C1=C(O)C=C(C=C1)C1=NC2=C(C=C1)N(C)N=C2 PZODBDHTCASPNJ-UHFFFAOYSA-N 0.000 claims 1
UKMDNYKYGQOWTF-UHFFFAOYSA-N 5-(1-methylpyrazolo[4,3-d]pyrimidin-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NC=C2N(C)N=CC2=N1 UKMDNYKYGQOWTF-UHFFFAOYSA-N 0.000 claims 1
JXSYPDIECVPSTG-UHFFFAOYSA-N 5-(1H-indazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound N1N=CC2=CC(=CC=C12)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C JXSYPDIECVPSTG-UHFFFAOYSA-N 0.000 claims 1
HFECLPRIOXNRNS-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)oxy-1,2,4-triazin-6-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)OC1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1 HFECLPRIOXNRNS-UHFFFAOYSA-N 0.000 claims 1
OQGNOCJYOHGFNV-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[3-(3,3,5,5-tetramethylpiperazin-1-yl)-1,2,4-triazin-6-yl]phenol Chemical compound CC1(C)CN(CC(C)(C)N1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1 OQGNOCJYOHGFNV-UHFFFAOYSA-N 0.000 claims 1
JZAITWRATWVIFL-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[3-(3,3,5,5-tetramethylpiperazin-1-yl)-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound Cl.Cl.CC1(C)CN(CC(C)(C)N1)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1 JZAITWRATWVIFL-UHFFFAOYSA-N 0.000 claims 1
LONKDCLAOQMQKK-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)NC1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1 LONKDCLAOQMQKK-UHFFFAOYSA-N 0.000 claims 1
RAZXPXHGADZSCV-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[3-[3-[(pyridin-2-ylmethylamino)methyl]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol Chemical compound N1N=CC(C2=CC(=C(C3=CN=C(N=N3)N3CCC(CNCC4=NC=CC=C4)C3)C=C2)O)=C1 RAZXPXHGADZSCV-UHFFFAOYSA-N 0.000 claims 1
QFFSOERAWOFABA-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[6-(2,2,6,6-tetramethylpiperidin-4-yl)oxy-1,2,4-triazin-3-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)OC1=CN=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1 QFFSOERAWOFABA-UHFFFAOYSA-N 0.000 claims 1
DBELCLNDDRXBHQ-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[6-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)NC1=CN=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1 DBELCLNDDRXBHQ-UHFFFAOYSA-N 0.000 claims 1
AUZUCBFOGZIHQQ-UHFFFAOYSA-N 5-(1H-pyrazol-5-yl)-2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)oxy-1,2,4-triazin-6-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)OC1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NNC=C1 AUZUCBFOGZIHQQ-UHFFFAOYSA-N 0.000 claims 1
OUGRYZLTFNOXEE-UHFFFAOYSA-N 5-(2-methyl-1,3-oxazol-5-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CC1=NC=C(O1)C1=CC(O)=C(C=C1)C1=CN=C(NC2CC(C)(C)NC(C)(C)C2)N=N1 OUGRYZLTFNOXEE-UHFFFAOYSA-N 0.000 claims 1
XJTTVGHBZUWSEZ-UHFFFAOYSA-N 5-(2-methyl-1,3-oxazol-5-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.Cc1ncc(o1)-c1ccc(c(O)c1)-c1cnc(NC2CC(C)(C)NC(C)(C)C2)nn1 XJTTVGHBZUWSEZ-UHFFFAOYSA-N 0.000 claims 1
RXWFDHXVZVKJKP-UHFFFAOYSA-N 5-(2-methyl-1,3-oxazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CN=C(C)O1 RXWFDHXVZVKJKP-UHFFFAOYSA-N 0.000 claims 1
QBEKKYQSXLXMGB-UHFFFAOYSA-N 5-(2-methyl-1,3-oxazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CC=1OC(=CN1)C=1C=CC(=C(C1)O)C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C QBEKKYQSXLXMGB-UHFFFAOYSA-N 0.000 claims 1
DQMCWLDVWBFLQI-UHFFFAOYSA-N 5-(2-methylpyrazol-3-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC=NN1C DQMCWLDVWBFLQI-UHFFFAOYSA-N 0.000 claims 1
QLHLAQFDYXMAAC-UHFFFAOYSA-N 5-(2-methyltetrazol-5-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN1N=C(N=N1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C QLHLAQFDYXMAAC-UHFFFAOYSA-N 0.000 claims 1
ZTGQZNMUAVGTCD-UHFFFAOYSA-N 5-(2-methyltetrazol-5-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound Cl.Cl.Cn1nnc(n1)-c1ccc(c(O)c1)-c1cnc(NC2CC(C)(C)NC(C)(C)C2)nn1 ZTGQZNMUAVGTCD-UHFFFAOYSA-N 0.000 claims 1
QWNZEVFFIJLKQE-UHFFFAOYSA-N 5-(2-methyltriazol-4-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN1N=CC(=N1)C1=CC(O)=C(C=C1)C1=CN=C(NC2CC(C)(C)NC(C)(C)C2)N=N1 QWNZEVFFIJLKQE-UHFFFAOYSA-N 0.000 claims 1
HJNRMEFXXPTVTF-UHFFFAOYSA-N 5-(2-methyltriazol-4-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound Cl.Cl.Cn1ncc(n1)-c1ccc(c(O)c1)-c1cnc(NC2CC(C)(C)NC(C)(C)C2)nn1 HJNRMEFXXPTVTF-UHFFFAOYSA-N 0.000 claims 1
VFONSPSHIKJVMO-UHFFFAOYSA-N 5-(2-methyltriazol-4-yl)-2-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol Chemical compound CC(C)NC1CCN(C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NN(C)N=C1 VFONSPSHIKJVMO-UHFFFAOYSA-N 0.000 claims 1
QAIICINLVPHWQM-UHFFFAOYSA-N 5-(3-chloro-1,2,4-triazol-1-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)N1C=NC(Cl)=N1 QAIICINLVPHWQM-UHFFFAOYSA-N 0.000 claims 1
SBKNRXCQYIAXTH-UHFFFAOYSA-N 5-(3-chloro-1,2,4-triazol-1-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound Cl.Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-n1cnc(Cl)n1 SBKNRXCQYIAXTH-UHFFFAOYSA-N 0.000 claims 1
CVYMVJNLDCIBJV-UHFFFAOYSA-N 5-(3-fluoro-1-methylpyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CN(C)N=C1F CVYMVJNLDCIBJV-UHFFFAOYSA-N 0.000 claims 1
CONYOAOGYGYUPE-UHFFFAOYSA-N 5-(3-fluoro-1-methylpyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1cn(C)nc1F CONYOAOGYGYUPE-UHFFFAOYSA-N 0.000 claims 1
ICSPSTOGVQEFBD-UHFFFAOYSA-N 5-(4-amino-1,3,5-triazin-2-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NC=NC(N)=N1 ICSPSTOGVQEFBD-UHFFFAOYSA-N 0.000 claims 1
OAPPNARHHIULGH-UHFFFAOYSA-N 5-(4-amino-1,3,5-triazin-2-yl)-2-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=CN=C(N=N1)C1=C(O)C=C(C=C1)C1=NC=NC(N)=N1 OAPPNARHHIULGH-UHFFFAOYSA-N 0.000 claims 1
KUJSLZIVPGTANN-UHFFFAOYSA-N 5-(4-chloro-1,3,5-triazin-2-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NC=NC(Cl)=N1 KUJSLZIVPGTANN-UHFFFAOYSA-N 0.000 claims 1
ZGGYPOPKLNCFOS-UHFFFAOYSA-N 5-(4-chloro-1,3,5-triazin-2-yl)-2-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=CN=C(N=N1)C1=C(O)C=C(C=C1)C1=NC=NC(Cl)=N1 ZGGYPOPKLNCFOS-UHFFFAOYSA-N 0.000 claims 1
MJFHMLGMONSLOV-UHFFFAOYSA-N 5-(4-chloroimidazol-1-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)N1C=NC(Cl)=C1 MJFHMLGMONSLOV-UHFFFAOYSA-N 0.000 claims 1
IDMNIAMGOXRJKT-UHFFFAOYSA-N 5-(4-chloroimidazol-1-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound Cl.Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-n1cnc(Cl)c1 IDMNIAMGOXRJKT-UHFFFAOYSA-N 0.000 claims 1
XHZLSIKIYNBXNY-UHFFFAOYSA-N 5-(4-fluoro-1H-pyrazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NNC=C1F XHZLSIKIYNBXNY-UHFFFAOYSA-N 0.000 claims 1
DFNYCQKTQOUKCW-UHFFFAOYSA-N 5-(4-fluoro-1H-pyrazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1[nH]ncc1F DFNYCQKTQOUKCW-UHFFFAOYSA-N 0.000 claims 1
DVMHPVZPRDEZSP-UHFFFAOYSA-N 5-(4-fluoroimidazol-1-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound FC=1N=CN(C=1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C DVMHPVZPRDEZSP-UHFFFAOYSA-N 0.000 claims 1
GTHJUUJHWQYZBS-UHFFFAOYSA-N 5-(4-fluoroimidazol-1-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CC1(C)CC(CC(C)(C)N1)Nc1ncc(nn1)-c1ccc(cc1O)-n1cnc(F)c1 GTHJUUJHWQYZBS-UHFFFAOYSA-N 0.000 claims 1
OZNJTPRZNRPEMV-KSSFIOAISA-N 5-(4-fluoroimidazol-1-yl)-2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]phenol Chemical compound FC=1N=CN(C=1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)N[C@@H]1[C@@H](C(NC(C1)(C)C)(C)C)F OZNJTPRZNRPEMV-KSSFIOAISA-N 0.000 claims 1
RFKJOWCWNCVLCL-MPWAUAJRSA-N 5-(4-fluoroimidazol-1-yl)-2-[3-[[(3S,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound Cl.Cl.CC1(C)C[C@H](Nc2ncc(nn2)-c2ccc(cc2O)-n2cnc(F)c2)[C@H](F)C(C)(C)N1 RFKJOWCWNCVLCL-MPWAUAJRSA-N 0.000 claims 1
OWKBKBQNNBTTPP-UHFFFAOYSA-N 5-(4-fluoroimidazol-1-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound FC=1N=CN(C=1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C OWKBKBQNNBTTPP-UHFFFAOYSA-N 0.000 claims 1
HICJHANDOSFYOC-UHFFFAOYSA-N 5-(4-fluoropyrazol-1-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound FC=1C=NN(C=1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C HICJHANDOSFYOC-UHFFFAOYSA-N 0.000 claims 1
KJKFAAZHCGXWBW-UHFFFAOYSA-N 5-(4-fluoropyrazol-1-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CC1(C)CC(CC(C)(C)N1)Nc1ncc(nn1)-c1ccc(cc1O)-n1cc(F)cn1 KJKFAAZHCGXWBW-UHFFFAOYSA-N 0.000 claims 1
CYCJBSUSPOHCLB-UHFFFAOYSA-N 5-(4-fluoropyrazol-1-yl)-2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol Chemical compound N1(C=C(C=N1)F)C1=CC(=C(C2=CN=C(N=N2)N2CCC(NC)C2)C=C1)O CYCJBSUSPOHCLB-UHFFFAOYSA-N 0.000 claims 1
NTSVRCHDZPBBIV-UHFFFAOYSA-N 5-(4-fluoropyrazol-1-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)N1C=C(F)C=N1 NTSVRCHDZPBBIV-UHFFFAOYSA-N 0.000 claims 1
IORNFOOBITUOPN-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound C1=C(O)C=CC(C2=CC=C(C3=CN=C(N(C4CC(NC(C4)(C)C)(C)C)C)N=N3)C(O)=C2)=C1 IORNFOOBITUOPN-UHFFFAOYSA-N 0.000 claims 1
SQLFYAATUWAKGQ-UHFFFAOYSA-N 5-(4-methoxy-1,3,5-triazin-2-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound COC1=NC(=NC=N1)C1=CC(O)=C(C=C1)C1=CN=C(N=N1)N(C)C1CC(C)(C)NC(C)(C)C1 SQLFYAATUWAKGQ-UHFFFAOYSA-N 0.000 claims 1
LVUXUTNNBVZJLP-UHFFFAOYSA-N 5-(4-methoxy-1,3,5-triazin-2-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound Cl.Cl.COc1ncnc(n1)-c1ccc(c(O)c1)-c1cnc(nn1)N(C)C1CC(C)(C)NC(C)(C)C1 LVUXUTNNBVZJLP-UHFFFAOYSA-N 0.000 claims 1
JIAOFCIZGSRWKW-UHFFFAOYSA-N 5-(4-methoxypyrazol-1-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound COC1=CN(N=C1)C1=CC(O)=C(C=C1)C1=CN=C(N=N1)N(C)C1CC(C)(C)NC(C)(C)C1 JIAOFCIZGSRWKW-UHFFFAOYSA-N 0.000 claims 1
MTJVFPDMVGIDDN-UHFFFAOYSA-N 5-(4-methoxypyrazol-1-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound Cl.Cl.COc1cnn(c1)-c1ccc(c(O)c1)-c1cnc(nn1)N(C)C1CC(C)(C)NC(C)(C)C1 MTJVFPDMVGIDDN-UHFFFAOYSA-N 0.000 claims 1
BWBRVESCPFWGKL-UHFFFAOYSA-N 5-(4-methylimidazol-1-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CC=1N=CN(C=1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C BWBRVESCPFWGKL-UHFFFAOYSA-N 0.000 claims 1
UACCBJAQZMATFE-UHFFFAOYSA-N 5-(4-methylimidazol-1-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.Cc1cn(cn1)-c1ccc(c(O)c1)-c1cnc(NC2CC(C)(C)NC(C)(C)C2)nn1 UACCBJAQZMATFE-UHFFFAOYSA-N 0.000 claims 1
COZJSVDADCOFIN-UHFFFAOYSA-N 5-(4-methylimidazol-1-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)N1C=NC(C)=C1 COZJSVDADCOFIN-UHFFFAOYSA-N 0.000 claims 1
KOZPMHVSRYHAFQ-UHFFFAOYSA-N 5-(4-methylimidazol-1-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-n1cnc(C)c1 KOZPMHVSRYHAFQ-UHFFFAOYSA-N 0.000 claims 1
KLLRHQRCCASKOY-UHFFFAOYSA-N 5-(4-methylpyrazol-1-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)N1C=C(C)C=N1 KLLRHQRCCASKOY-UHFFFAOYSA-N 0.000 claims 1
CECJZUBKOQCQCI-UHFFFAOYSA-N 5-(4-methylpyrazol-1-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound Cl.Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-n1cc(C)cn1 CECJZUBKOQCQCI-UHFFFAOYSA-N 0.000 claims 1
BPJAOVANZXYYDX-UHFFFAOYSA-N 5-(5-chloro-1-methylpyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound ClC1=C(C=NN1C)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C BPJAOVANZXYYDX-UHFFFAOYSA-N 0.000 claims 1
WRQAXDOUCRXENC-UHFFFAOYSA-N 5-(5-chloro-1-methylpyrazol-4-yl)-2-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]phenol Chemical compound ClC1=C(C=NN1C)C=1C=CC(=C(C=1)O)C=1N=NC(=CN=1)N(C1CC(NC(C1)(C)C)(C)C)C WRQAXDOUCRXENC-UHFFFAOYSA-N 0.000 claims 1
IFDGDBRUVSEZSB-UHFFFAOYSA-N 5-(5-chloro-1H-pyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1Cl IFDGDBRUVSEZSB-UHFFFAOYSA-N 0.000 claims 1
GTAAQEOIQQKZCI-UHFFFAOYSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)oxy-1,2,4-triazin-6-yl]phenol Chemical compound FC1=NNC=C1C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)OC1CC(NC(C1)(C)C)(C)C GTAAQEOIQQKZCI-UHFFFAOYSA-N 0.000 claims 1
RKRVHTMUCCNUCB-UHFFFAOYSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[3-(2,2,6,6-tetramethylpiperidin-4-yl)oxy-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound Cl.Cl.CC1(C)CC(CC(C)(C)N1)Oc1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1F RKRVHTMUCCNUCB-UHFFFAOYSA-N 0.000 claims 1
LTIPJLZSKIWEAC-UHFFFAOYSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound FC1=NNC=C1C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C LTIPJLZSKIWEAC-UHFFFAOYSA-N 0.000 claims 1
NINQKVAQNCASTO-UHFFFAOYSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol trihydrochloride Chemical compound Cl.Cl.Cl.FC1=NNC=C1C=1C=CC(=C(C1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C NINQKVAQNCASTO-UHFFFAOYSA-N 0.000 claims 1
CJGBRMPGANBSSO-RHSMWYFYSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[3-[[(3R,4R)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]phenol Chemical compound FC1=NNC=C1C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)N[C@H]1[C@H](C(NC(C1)(C)C)(C)C)F CJGBRMPGANBSSO-RHSMWYFYSA-N 0.000 claims 1
AMFVFTFBHXSPGJ-LVVRIOTCSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[3-[[(3R,4R)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]amino]-1,2,4-triazin-6-yl]phenol dihydrochloride Chemical compound CC1(C[C@H]([C@H](C(N1)(C)C)F)NC2=NC=C(N=N2)C3=C(C=C(C=C3)C4=C(NN=C4)F)O)C.Cl.Cl AMFVFTFBHXSPGJ-LVVRIOTCSA-N 0.000 claims 1
PVJBITGLCVUAHK-UHFFFAOYSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1F PVJBITGLCVUAHK-UHFFFAOYSA-N 0.000 claims 1
OACYBEAMOXUWHE-UHFFFAOYSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1cn[nH]c1F OACYBEAMOXUWHE-UHFFFAOYSA-N 0.000 claims 1
RBZNOFWDCQAHRP-UHFFFAOYSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[6-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-3-yl]phenol hydrochloride Chemical compound Cl.FC1=C(C=NN1)C=1C=CC(=C(C1)O)C=1N=NC(=CN1)N(C1CC(NC(C1)(C)C)(C)C)C RBZNOFWDCQAHRP-UHFFFAOYSA-N 0.000 claims 1
BANGXLYLTIKQAS-UHFFFAOYSA-N 5-(5-methyl-1,3,4-oxadiazol-2-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NN=C(C)O1 BANGXLYLTIKQAS-UHFFFAOYSA-N 0.000 claims 1
DPBAUFGIYSSJQS-UHFFFAOYSA-N 5-(5-methyl-1,3,4-oxadiazol-2-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1nnc(C)o1 DPBAUFGIYSSJQS-UHFFFAOYSA-N 0.000 claims 1
ZRHPAVYYSCYQIF-UHFFFAOYSA-N 5-(5-methyl-1,3-oxazol-2-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NC=C(C)O1 ZRHPAVYYSCYQIF-UHFFFAOYSA-N 0.000 claims 1
USSYFXGEVSGBCU-UHFFFAOYSA-N 5-(5-methyl-1,3-oxazol-2-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrobromide Chemical compound Br.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1ncc(C)o1 USSYFXGEVSGBCU-UHFFFAOYSA-N 0.000 claims 1
NJMHMOSITDQSKC-UHFFFAOYSA-N 5-(5-methyl-1H-pyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CNN=C1C NJMHMOSITDQSKC-UHFFFAOYSA-N 0.000 claims 1
YOSSMHZDEPCDDO-UHFFFAOYSA-N 5-(6,7-difluoro-1-methylbenzimidazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=C(F)C(F)=C2N(C)C=NC2=C1 YOSSMHZDEPCDDO-UHFFFAOYSA-N 0.000 claims 1
DHMNJNOFSWVDLW-UHFFFAOYSA-N 5-(6,7-difluoro-3H-benzimidazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=C(F)C(F)=C2NC=NC2=C1 DHMNJNOFSWVDLW-UHFFFAOYSA-N 0.000 claims 1
ZRMSWDDIYSRGLZ-UHFFFAOYSA-N 5-(6-methoxy-1,2,4-triazin-3-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound COC1=CN=C(N=N1)C1=CC(O)=C(C=C1)C1=CN=C(N=N1)N(C)C1CC(C)(C)NC(C)(C)C1 ZRMSWDDIYSRGLZ-UHFFFAOYSA-N 0.000 claims 1
IYHHJTLXNDEUHD-UHFFFAOYSA-N 5-(6-methoxypyrimidin-4-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound COC1=CC(=NC=N1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C IYHHJTLXNDEUHD-UHFFFAOYSA-N 0.000 claims 1
DUYWVNZGMLTBGI-UHFFFAOYSA-N 5-(6-methoxypyrimidin-4-yl)-2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol Chemical compound CNC1CCN(C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC(OC)=NC=N1 DUYWVNZGMLTBGI-UHFFFAOYSA-N 0.000 claims 1
OWQWNVPSSIAMAV-UHFFFAOYSA-N 5-(6-methoxypyrimidin-4-yl)-2-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol Chemical compound COC1=CC(=NC=N1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)N1CC(CC1)NC(C)C OWQWNVPSSIAMAV-UHFFFAOYSA-N 0.000 claims 1
GUIZLELWLHMLNI-UHFFFAOYSA-N 5-(7-fluoro-1-methylbenzimidazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC(F)=C2N(C)C=NC2=C1 GUIZLELWLHMLNI-UHFFFAOYSA-N 0.000 claims 1
TZUNAXSVLAJPAL-UHFFFAOYSA-N 5-(7-fluoro-1H-indazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound FC=1C=C(C=C2C=NNC=12)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C TZUNAXSVLAJPAL-UHFFFAOYSA-N 0.000 claims 1
XQCRGNBTUAURSO-UHFFFAOYSA-N 5-(7-fluoro-3H-benzimidazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound C1=NC2=C(N1)C(F)=CC(C1=CC=C(C3=CN=C(N=N3)N(C3CC(NC(C)(C)C3)(C)C)C)C(O)=C1)=C2 XQCRGNBTUAURSO-UHFFFAOYSA-N 0.000 claims 1
WNOKGVLUXBYLMF-UHFFFAOYSA-N 5-(pyridin-3-ylamino)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1ncc(nn1)-c1ccc(Nc2cccnc2)cc1O WNOKGVLUXBYLMF-UHFFFAOYSA-N 0.000 claims 1
XZNGBNGLUUFPJI-UHFFFAOYSA-N 5-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]-1H-pyridin-2-one Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1ccc(=O)[nH]c1 XZNGBNGLUUFPJI-UHFFFAOYSA-N 0.000 claims 1
IUVSLLWTSRRGRM-UHFFFAOYSA-N 5-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]-2-methylpyridazin-3-one Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC(=O)N(C)N=C1 IUVSLLWTSRRGRM-UHFFFAOYSA-N 0.000 claims 1
MRISHWOQUJBXPE-UHFFFAOYSA-N 5-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]-2-methylpyridazin-3-one dihydrochloride Chemical compound Cl.Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1cnn(C)c(=O)c1 MRISHWOQUJBXPE-UHFFFAOYSA-N 0.000 claims 1
WAKQNUMKMPUXSL-UHFFFAOYSA-N 5-[4-(hydroxymethyl)pyrazol-1-yl]-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)N1C=C(CO)C=N1 WAKQNUMKMPUXSL-UHFFFAOYSA-N 0.000 claims 1
MVJHGUYINUXHEH-UHFFFAOYSA-N 5-[4-(hydroxymethyl)triazol-2-yl]-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)N1N=CC(CO)=N1 MVJHGUYINUXHEH-UHFFFAOYSA-N 0.000 claims 1
HLNSYZSHXJLJOL-UHFFFAOYSA-N 5-[6-(hydroxymethyl)pyrimidin-4-yl]-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC(CO)=NC=N1 HLNSYZSHXJLJOL-UHFFFAOYSA-N 0.000 claims 1
ZXBKFPFIHHYDOQ-UHFFFAOYSA-N 5-[6-(hydroxymethyl)pyrimidin-4-yl]-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1cc(CO)ncn1 ZXBKFPFIHHYDOQ-UHFFFAOYSA-N 0.000 claims 1
RGNNIWCWAFZQSV-UHFFFAOYSA-N 5-[6-(methylamino)pyrimidin-4-yl]-2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol Chemical compound CNC1CCN(C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC(NC)=NC=N1 RGNNIWCWAFZQSV-UHFFFAOYSA-N 0.000 claims 1
ILODMWDHRYEQGA-UHFFFAOYSA-N 5-imidazo[1,2-a]pyrazin-2-yl-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1ncc(nn1)-c1ccc(cc1O)-c1cn2ccncc2n1 ILODMWDHRYEQGA-UHFFFAOYSA-N 0.000 claims 1
CVBWMTGFNAVJDE-UHFFFAOYSA-N 5-imidazo[1,2-a]pyrazin-2-yl-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CC1(C)CC(CC(C)(C)N1)Nc1ncc(nn1)-c1ccc(cc1O)-c1cn2ccncc2n1 CVBWMTGFNAVJDE-UHFFFAOYSA-N 0.000 claims 1
ZDZPXTCCPKSJIG-UHFFFAOYSA-N 5-imidazo[1,2-a]pyrazin-6-yl-2-[3-(7-methyl-2,7-diazaspiro[3.5]nonan-2-yl)-1,2,4-triazin-6-yl]phenol Chemical compound CN1CCC2(CN(C2)C2=NC=C(N=N2)C2=C(O)C=C(C=C2)C2=CN3C=CN=C3C=N2)CC1 ZDZPXTCCPKSJIG-UHFFFAOYSA-N 0.000 claims 1
BTNOLGIMXVAOTR-UHFFFAOYSA-N 5-imidazo[1,2-a]pyrazin-6-yl-2-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol Chemical compound CC(C)NC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-c1cn2ccnc2cn1 BTNOLGIMXVAOTR-UHFFFAOYSA-N 0.000 claims 1
PCHAIVPEUXLAGH-UHFFFAOYSA-N 5-imidazo[1,2-a]pyrazin-6-yl-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CN2C=CN=C2C=N1 PCHAIVPEUXLAGH-UHFFFAOYSA-N 0.000 claims 1
MTVBIJOSLVRSLA-UHFFFAOYSA-N 5-imidazo[1,2-a]pyrazin-6-yl-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1cn2ccnc2cn1 MTVBIJOSLVRSLA-UHFFFAOYSA-N 0.000 claims 1
CNSLUAQDCUKVLR-UHFFFAOYSA-N 5-imidazo[1,2-a]pyridin-2-yl-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound N=1C(=CN2C=1C=CC=C2)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C CNSLUAQDCUKVLR-UHFFFAOYSA-N 0.000 claims 1
SWYLGHLDSSHASJ-UHFFFAOYSA-N 5-imidazo[1,2-b]pyridazin-6-yl-2-[3-(7-methyl-2,7-diazaspiro[3.5]nonan-2-yl)-1,2,4-triazin-6-yl]phenol Chemical compound CN1CCC2(CN(C2)C2=NC=C(N=N2)C2=C(O)C=C(C=C2)C2=NN3C=CN=C3C=C2)CC1 SWYLGHLDSSHASJ-UHFFFAOYSA-N 0.000 claims 1
XURCZDBLZACCEP-UHFFFAOYSA-N 5-imidazo[1,2-b]pyridazin-6-yl-2-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol Chemical compound CC(C)NC1CCN(C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NN2C=CN=C2C=C1 XURCZDBLZACCEP-UHFFFAOYSA-N 0.000 claims 1
PGXRBNLYAQGZEJ-UHFFFAOYSA-N 5-imidazo[1,2-b]pyridazin-6-yl-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NN2C=CN=C2C=C1 PGXRBNLYAQGZEJ-UHFFFAOYSA-N 0.000 claims 1
VBCYKOGGCNGOTA-UHFFFAOYSA-N 5-imidazo[1,2-b]pyridazin-6-yl-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1ncc(nn1)-c1ccc(cc1O)-c1ccc2nccn2n1 VBCYKOGGCNGOTA-UHFFFAOYSA-N 0.000 claims 1
AHICVBUHIZBMEN-UHFFFAOYSA-N 5-imidazol-1-yl-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound N1(C=NC=C1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C AHICVBUHIZBMEN-UHFFFAOYSA-N 0.000 claims 1
IPRZJUJOLPIROC-UHFFFAOYSA-N 5-imidazol-1-yl-2-[3-[3-(methylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol Chemical compound CNC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-n1ccnc1 IPRZJUJOLPIROC-UHFFFAOYSA-N 0.000 claims 1
FCRGETOHSQVXGE-UHFFFAOYSA-N 5-imidazol-1-yl-2-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol Chemical compound CC(C)NC1CCN(C1)c1ncc(nn1)-c1ccc(cc1O)-n1ccnc1 FCRGETOHSQVXGE-UHFFFAOYSA-N 0.000 claims 1
YBMNUWYGLDOSFR-UHFFFAOYSA-N 5-imidazol-1-yl-2-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenol hydrochloride Chemical compound Cl.N1(C=NC=C1)C=1C=CC(=C(C1)O)C1=CN=C(N=N1)N1CC(CC1)NC(C)C YBMNUWYGLDOSFR-UHFFFAOYSA-N 0.000 claims 1
LKKKWEGOGLXKSV-UHFFFAOYSA-N 5-imidazol-1-yl-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound N1(C=NC=C1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C LKKKWEGOGLXKSV-UHFFFAOYSA-N 0.000 claims 1
ZEOAFUFWAUTHGR-UHFFFAOYSA-N 5-pyridazin-4-yl-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)NC1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CN=NC=C1 ZEOAFUFWAUTHGR-UHFFFAOYSA-N 0.000 claims 1
DKBHVEOYQRCKKE-UHFFFAOYSA-N 5-pyrimidin-2-yl-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)NC1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=NC=CC=N1 DKBHVEOYQRCKKE-UHFFFAOYSA-N 0.000 claims 1
WMNVRCQDPGGRCW-UHFFFAOYSA-N 6-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-2-fluoro-3-(1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=CC=C(C(=C1O)F)C=1C=NNC=1 WMNVRCQDPGGRCW-UHFFFAOYSA-N 0.000 claims 1
MNNKDERNWFSIFT-UHFFFAOYSA-N 6-[3-[3-(tert-butylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-2-fluoro-3-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CC(C)(C)NC1CCN(C1)c1ncc(nn1)-c1ccc(-c2cn[nH]c2)c(F)c1O MNNKDERNWFSIFT-UHFFFAOYSA-N 0.000 claims 1
MPAGDCJUWXSDJA-UHFFFAOYSA-N 6-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]quinolin-7-ol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C2N=CC=CC2=C1 MPAGDCJUWXSDJA-UHFFFAOYSA-N 0.000 claims 1
PVUJUSUQGPYTRV-UHFFFAOYSA-N 6-[3-hydroxy-4-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenyl]-3-methylpyrimidin-4-one Chemical compound OC=1C=C(C=CC=1C1=CN=C(N=N1)N1CC(CC1)NC(C)C)C1=CC(N(C=N1)C)=O PVUJUSUQGPYTRV-UHFFFAOYSA-N 0.000 claims 1
MPRIBVKAGBMVLE-UHFFFAOYSA-N 6-[3-hydroxy-4-[3-[3-(propan-2-ylamino)pyrrolidin-1-yl]-1,2,4-triazin-6-yl]phenyl]-3-methylpyrimidin-4-one hydrochloride Chemical compound Cl.OC=1C=C(C=CC1C1=CN=C(N=N1)N1CC(CC1)NC(C)C)C1=CC(N(C=N1)C)=O MPRIBVKAGBMVLE-UHFFFAOYSA-N 0.000 claims 1
YQRVFVZBYSYUHM-UHFFFAOYSA-N 6-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]-3-methylpyrimidin-4-one Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(O)C=C(C=C1)C1=CC(=O)N(C)C=N1 YQRVFVZBYSYUHM-UHFFFAOYSA-N 0.000 claims 1
KOWITKPLCGTEEL-UHFFFAOYSA-N 6-[3-hydroxy-4-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl]-3-methylpyrimidin-4-one dihydrochloride Chemical compound Cl.Cl.OC=1C=C(C=CC1C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C)C1=CC(N(C=N1)C)=O KOWITKPLCGTEEL-UHFFFAOYSA-N 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
TWAQQEOIIQZKOT-VPYROQPTSA-N C(N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C)([2H])([2H])[2H] Chemical compound C(N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C)([2H])([2H])[2H] TWAQQEOIIQZKOT-VPYROQPTSA-N 0.000 claims 1
USFVVTKYTOQATQ-OWKBQAHQSA-N Cl.C(N1N=CC(=C1)C=1C=CC(=C(C1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C)([2H])([2H])[2H] Chemical compound Cl.C(N1N=CC(=C1)C=1C=CC(=C(C1)O)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C)([2H])([2H])[2H] USFVVTKYTOQATQ-OWKBQAHQSA-N 0.000 claims 1
YISQCEKJTWVFTL-YLSPSJLGSA-N Cl.Cl.C(N1N=CC(=C1)C=1C=CC(=C(C1)O)C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C)([2H])([2H])[2H] Chemical compound Cl.Cl.C(N1N=CC(=C1)C=1C=CC(=C(C1)O)C1=CN=C(N=N1)N(C1CC(NC(C1)(C)C)(C)C)C)([2H])([2H])[2H] YISQCEKJTWVFTL-YLSPSJLGSA-N 0.000 claims 1
SISBKYXCVOUUTN-ZGNJCNNKSA-N F[C@@H]1C(NC(C[C@@H]1NC=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NN(C=1)C([2H])([2H])[2H])O)(C)C)(C)C Chemical compound F[C@@H]1C(NC(C[C@@H]1NC=1N=NC(=CN=1)C1=C(C=C(C=C1)C=1C=NN(C=1)C([2H])([2H])[2H])O)(C)C)(C)C SISBKYXCVOUUTN-ZGNJCNNKSA-N 0.000 claims 1
VBTRYICOGSPHFT-UHFFFAOYSA-N N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,2,4-triazin-3-amine Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=CN=N1 VBTRYICOGSPHFT-UHFFFAOYSA-N 0.000 claims 1
VSYMKJJFDYXAMR-UHFFFAOYSA-N [2-[3-[3-[(cyclopropylamino)methyl]pyrrolidin-1-yl]-1,2,4-triazin-6-yl]-5-(1H-pyrazol-4-yl)phenyl] formate Chemical compound O=COC1=C(C=CC(=C1)C1=CNN=C1)C1=CN=C(N=N1)N1CCC(CNC2CC2)C1 VSYMKJJFDYXAMR-UHFFFAOYSA-N 0.000 claims 1
LCYKHNZTXQPBMP-UHFFFAOYSA-N [2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyridazin-3-ylphenyl] formate Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(OC=O)C=C(C=C1)C1=CC=CN=N1 LCYKHNZTXQPBMP-UHFFFAOYSA-N 0.000 claims 1
JDPITFVOCSCWTM-UHFFFAOYSA-N [2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyridin-2-ylphenyl] formate Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(OC=O)C=C(C=C1)C1=NC=CC=C1 JDPITFVOCSCWTM-UHFFFAOYSA-N 0.000 claims 1
NPJBINVWUGANOE-UHFFFAOYSA-N [2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyrimidin-4-ylphenyl] formate Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(OC=O)C=C(C=C1)C1=CC=NC=N1 NPJBINVWUGANOE-UHFFFAOYSA-N 0.000 claims 1
ZGQJMPPAUYNUTE-UHFFFAOYSA-N [2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]-5-pyrimidin-5-ylphenyl] formate Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(OC=O)C=C(C=C1)C1=CN=CN=C1 ZGQJMPPAUYNUTE-UHFFFAOYSA-N 0.000 claims 1
DOTXQIMNCLZKHS-UHFFFAOYSA-N [5-(1-methylbenzimidazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl] formate Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(OC=O)C=C(C=C1)C1=CC=C2N(C)C=NC2=C1 DOTXQIMNCLZKHS-UHFFFAOYSA-N 0.000 claims 1
LVOPEXUSJAJMDK-UHFFFAOYSA-N [5-(1-methylpyrazol-3-yl)-2-[3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl] formate Chemical compound C(=O)OC1=C(C=CC(=C1)C1=NN(C=C1)C)C1=CN=C(N=N1)NC1CC(NC(C1)(C)C)(C)C LVOPEXUSJAJMDK-UHFFFAOYSA-N 0.000 claims 1
BCDOROZRDLASMX-UHFFFAOYSA-N [5-(5-methyl-1H-pyrazol-4-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl] formate Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(OC=O)C=C(C=C1)C1=CNN=C1C BCDOROZRDLASMX-UHFFFAOYSA-N 0.000 claims 1
ZAMICXPNMRTSIV-UHFFFAOYSA-N [5-(6,7-difluoro-1-methylbenzimidazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl] formate Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(OC=O)C=C(C=C1)C1=C(F)C(F)=C2N(C)C=NC2=C1 ZAMICXPNMRTSIV-UHFFFAOYSA-N 0.000 claims 1
FHJHUSYNOFDPDJ-UHFFFAOYSA-N [5-(6,7-difluoro-3H-benzimidazol-5-yl)-2-[3-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,2,4-triazin-6-yl]phenyl] formate Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)C1=NC=C(N=N1)C1=C(OC=O)C=C(C=C1)C1=C(F)C(F)=C2NC=NC2=C1 FHJHUSYNOFDPDJ-UHFFFAOYSA-N 0.000 claims 1
125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
125000002393 azetidinyl group Chemical group 0.000 claims 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
125000005241 heteroarylamino group Chemical group 0.000 claims 1
XVQUOJBERHHONY-UHFFFAOYSA-N isometheptene Chemical compound CNC(C)CCC=C(C)C XVQUOJBERHHONY-UHFFFAOYSA-N 0.000 claims 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
PUBSMDUBHLYMIX-UHFFFAOYSA-N phenol;dihydrochloride Chemical compound Cl.Cl.OC1=CC=CC=C1 PUBSMDUBHLYMIX-UHFFFAOYSA-N 0.000 claims 1
DNRXKUPYJHTZJE-UHFFFAOYSA-N phenol;hydrobromide Chemical compound Br.OC1=CC=CC=C1 DNRXKUPYJHTZJE-UHFFFAOYSA-N 0.000 claims 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
239000011877 solvent mixture Substances 0.000 claims 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
150000003254 radicals Chemical class 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 3
125000005917 3-methylpentyl group Chemical group 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 1
150000005840 aryl radicals Chemical group 0.000 description 1
125000003828 azulenyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004431 deuterium atom Chemical group 0.000 description 1
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1

JP2020551538A 2018-03-27 2019-03-27 ハンチントン病を処置するための化合物 Active JP7399869B2 (ja)