JP2018527353A5 - - Google Patents
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- JP2018527353A5 JP2018527353A5 JP2018511427A JP2018511427A JP2018527353A5 JP 2018527353 A5 JP2018527353 A5 JP 2018527353A5 JP 2018511427 A JP2018511427 A JP 2018511427A JP 2018511427 A JP2018511427 A JP 2018511427A JP 2018527353 A5 JP2018527353 A5 JP 2018527353A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- chloro
- triazol
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 63
- 229910052799 carbon Inorganic materials 0.000 claims 56
- 125000005843 halogen group Chemical group 0.000 claims 55
- 150000001875 compounds Chemical class 0.000 claims 49
- 150000003839 salts Chemical class 0.000 claims 45
- 229910052736 halogen Inorganic materials 0.000 claims 42
- 150000002367 halogens Chemical class 0.000 claims 40
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 40
- 229910052757 nitrogen Inorganic materials 0.000 claims 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 32
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 30
- -1 where Chemical group 0.000 claims 30
- 125000001072 heteroaryl group Chemical group 0.000 claims 28
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 26
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 25
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 24
- 125000003118 aryl group Chemical group 0.000 claims 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 125000001424 substituent group Chemical group 0.000 claims 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 12
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 11
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 10
- 125000004122 cyclic group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- QDDXBJMPDATEOE-UHFFFAOYSA-N 5-tert-butyl-2-methyl-4-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]benzonitrile Chemical compound CN1C(=O)NN=C1COC1=CC(C)=C(C=C1C(C)(C)C)C#N QDDXBJMPDATEOE-UHFFFAOYSA-N 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- WWVZWMVATOMJDK-UHFFFAOYSA-N 2-[3-[5-chloro-4-methyl-2-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]phenyl]-4-fluorophenoxy]-N,N-dimethylacetamide Chemical compound ClC=1C(=CC(=C(C=1)C=1C=C(OCC(=O)N(C)C)C=CC=1F)OCC1=NNC(N1C)=O)C WWVZWMVATOMJDK-UHFFFAOYSA-N 0.000 claims 2
- PKLSETCYCDOVNK-UHFFFAOYSA-N 2-[[3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-2H-pyrazolo[3,4-d]pyrimidin-6-yl]-methylamino]ethanol Chemical compound C(C)(C)(C)C1=C(OCC2=NNC3=NC(=NC=C32)N(CCO)C)C=C(C(=C1)Cl)C PKLSETCYCDOVNK-UHFFFAOYSA-N 0.000 claims 2
- BLCISVMFIVYJDC-UHFFFAOYSA-N 2-[[3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-2H-pyrazolo[3,4-d]pyrimidin-6-yl]oxy]ethanol Chemical compound C(C)(C)(C)C1=C(OCC2=NNC3=NC(=NC=C32)OCCO)C=C(C(=C1)Cl)C BLCISVMFIVYJDC-UHFFFAOYSA-N 0.000 claims 2
- QESROAGYPSSLSI-UHFFFAOYSA-N 2-chloro-4-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]-5-[3-(1H-pyrazol-5-yl)phenyl]benzonitrile Chemical compound CN1C(=O)NN=C1COC1=CC(Cl)=C(C=C1C1=CC(=CC=C1)C1=NNC=C1)C#N QESROAGYPSSLSI-UHFFFAOYSA-N 0.000 claims 2
- HIYXCJWCUWKAER-UHFFFAOYSA-N 2-chloro-4-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]-5-phenylbenzonitrile Chemical compound CN1C(=O)NN=C1COC1=CC(Cl)=C(C=C1C1=CC=CC=C1)C#N HIYXCJWCUWKAER-UHFFFAOYSA-N 0.000 claims 2
- VEXFUZNSQIPXDQ-UHFFFAOYSA-N 2-chloro-5-(2-fluoro-3-methoxyphenyl)-4-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]benzonitrile Chemical compound COC1=CC=CC(=C1F)C1=CC(C#N)=C(Cl)C=C1OCC1=NNC(=O)N1C VEXFUZNSQIPXDQ-UHFFFAOYSA-N 0.000 claims 2
- SUNFQMVUKXUWKC-UHFFFAOYSA-N 2-chloro-5-(2-fluoro-5-propan-2-yloxyphenyl)-4-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]benzonitrile Chemical compound CC(C)OC1=CC(=C(F)C=C1)C1=CC(C#N)=C(Cl)C=C1OCC1=NNC(=O)N1C SUNFQMVUKXUWKC-UHFFFAOYSA-N 0.000 claims 2
- DUEFAZIVZFMZAY-UHFFFAOYSA-N 2-chloro-5-(2-fluorophenyl)-4-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]benzonitrile Chemical compound CN1C(=O)NN=C1COC1=CC(Cl)=C(C=C1C1=C(F)C=CC=C1)C#N DUEFAZIVZFMZAY-UHFFFAOYSA-N 0.000 claims 2
- FUYSSUNMLZTNTR-UHFFFAOYSA-N 2-chloro-5-(5-cyclopropyloxy-2-fluorophenyl)-4-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]benzonitrile Chemical compound CN1C(=O)NN=C1COC1=CC(Cl)=C(C=C1C1=C(F)C=CC(OC2CC2)=C1)C#N FUYSSUNMLZTNTR-UHFFFAOYSA-N 0.000 claims 2
- BDPOKPHLEFABMV-UHFFFAOYSA-N 2-chloro-5-[2-fluoro-5-(pyrrolidine-1-carbonyl)phenyl]-4-(2H-pyrazolo[3,4-b]pyridin-3-ylmethoxy)benzonitrile Chemical compound ClC1=C(C#N)C=C(C(=C1)OCC1=NNC2=NC=CC=C21)C1=C(C=CC(=C1)C(=O)N1CCCC1)F BDPOKPHLEFABMV-UHFFFAOYSA-N 0.000 claims 2
- BFXLJYUNOKDVIN-UHFFFAOYSA-N 2-chloro-5-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-4-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]benzonitrile Chemical compound CN1C(=O)NN=C1COC1=CC(Cl)=C(C=C1C1=CC(=CC=C1)C1=NOC(C)=N1)C#N BFXLJYUNOKDVIN-UHFFFAOYSA-N 0.000 claims 2
- FSTPMFASNVISBU-UHFFFAOYSA-N 2-methoxybenzonitrile Chemical compound COC1=CC=CC=C1C#N FSTPMFASNVISBU-UHFFFAOYSA-N 0.000 claims 2
- DBWAYLSZVMGRMC-UHFFFAOYSA-N 3-[(2-tert-butyl-4-chloro-5-fluorophenoxy)methyl]-4-methyl-1H-1,2,4-triazol-5-one Chemical compound CN1C(=O)NN=C1COC1=C(C=C(Cl)C(F)=C1)C(C)(C)C DBWAYLSZVMGRMC-UHFFFAOYSA-N 0.000 claims 2
- DATJNCIOBJFUFJ-UHFFFAOYSA-N 3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-4-methyl-1H-1,2,4-triazol-5-one Chemical compound CN1C(=O)NN=C1COC1=C(C=C(Cl)C(C)=C1)C(C)(C)C DATJNCIOBJFUFJ-UHFFFAOYSA-N 0.000 claims 2
- YGBUEZWNNQLXCK-UHFFFAOYSA-N 3-[(4-chloro-2-cyclobutyl-5-methylphenoxy)methyl]-4-methyl-1H-1,2,4-triazol-5-one Chemical compound CN1C(=O)NN=C1COC1=C(C=C(Cl)C(C)=C1)C1CCC1 YGBUEZWNNQLXCK-UHFFFAOYSA-N 0.000 claims 2
- JGHYMZNTLMFTNH-UHFFFAOYSA-N 3-[(4-chloro-2-cyclohexyl-5-methylphenoxy)methyl]-4-methyl-1H-1,2,4-triazol-5-one Chemical compound CN1C(=O)NN=C1COC1=C(C=C(Cl)C(C)=C1)C1CCCCC1 JGHYMZNTLMFTNH-UHFFFAOYSA-N 0.000 claims 2
- NCTHOSYNPRRZAY-UHFFFAOYSA-N 3-[(4-chloro-5-methyl-2-propan-2-ylphenoxy)methyl]-4-methyl-1H-1,2,4-triazol-5-one Chemical compound CC(C)C1=C(OCC2=NNC(=O)N2C)C=C(C)C(Cl)=C1 NCTHOSYNPRRZAY-UHFFFAOYSA-N 0.000 claims 2
- HBHPRJNNVHPTMH-UHFFFAOYSA-N 3-[5-chloro-4-methyl-2-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]phenyl]-4-fluoro-N-(2-methoxyethyl)-N-methylbenzamide Chemical compound COCCN(C)C(=O)C1=CC(=C(F)C=C1)C1=C(OCC2=NNC(=O)N2C)C=C(C)C(Cl)=C1 HBHPRJNNVHPTMH-UHFFFAOYSA-N 0.000 claims 2
- VRWZUAIGDKFRPU-UHFFFAOYSA-N 3-[[4-chloro-2-(2-methoxypyridin-3-yl)-5-methylphenoxy]methyl]-4-methyl-1H-1,2,4-triazol-5-one Chemical compound ClC1=CC(=C(OCC2=NNC(N2C)=O)C=C1C)C=1C(=NC=CC=1)OC VRWZUAIGDKFRPU-UHFFFAOYSA-N 0.000 claims 2
- CGQSQLCZARJYST-UHFFFAOYSA-N 3-[[4-chloro-2-(5-cyclopropyloxy-2-fluorophenyl)-5-methylphenoxy]methyl]-4-methyl-1H-1,2,4-triazol-5-one Chemical compound ClC1=CC(=C(OCC2=NNC(N2C)=O)C=C1C)C1=C(C=CC(=C1)OC1CC1)F CGQSQLCZARJYST-UHFFFAOYSA-N 0.000 claims 2
- CVQBAGLJZYUDKO-UHFFFAOYSA-N 3-[[4-chloro-2-[2-fluoro-5-(oxolan-2-ylmethoxy)phenyl]-5-methylphenoxy]methyl]-4-methyl-1H-1,2,4-triazol-5-one Chemical compound ClC1=CC(=C(OCC2=NNC(N2C)=O)C=C1C)C1=C(C=CC(=C1)OCC1OCCC1)F CVQBAGLJZYUDKO-UHFFFAOYSA-N 0.000 claims 2
- SPGLRARNKLUADS-UHFFFAOYSA-N 3-[[4-chloro-2-[2-fluoro-5-(pyrrolidine-1-carbonyl)phenyl]-5-methylphenoxy]methyl]-4-methyl-1H-1,2,4-triazol-5-one Chemical compound ClC1=CC(=C(OCC2=NNC(N2C)=O)C=C1C)C1=C(C=CC(=C1)C(=O)N1CCCC1)F SPGLRARNKLUADS-UHFFFAOYSA-N 0.000 claims 2
- MMGNJHJWCCHVNF-UHFFFAOYSA-N 3-[[4-chloro-5-methyl-2-(1,2-oxazol-5-yl)phenoxy]methyl]-4-methyl-1H-1,2,4-triazol-5-one Chemical compound CN1C(=O)NN=C1COC1=C(C=C(Cl)C(C)=C1)C1=CC=NO1 MMGNJHJWCCHVNF-UHFFFAOYSA-N 0.000 claims 2
- FUMNXHJNCMFWAW-UHFFFAOYSA-N 3-[[4-chloro-5-methyl-2-[3-(morpholine-4-carbonyl)phenyl]phenoxy]methyl]-4-methyl-1H-1,2,4-triazol-5-one Chemical compound ClC1=CC(=C(OCC2=NNC(N2C)=O)C=C1C)C1=CC(=CC=C1)C(=O)N1CCOCC1 FUMNXHJNCMFWAW-UHFFFAOYSA-N 0.000 claims 2
- IURJUKLFVHTMJE-UHFFFAOYSA-N 3-tert-butyl-4-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]benzonitrile Chemical compound CN1C(=O)NN=C1COC1=C(C=C(C=C1)C#N)C(C)(C)C IURJUKLFVHTMJE-UHFFFAOYSA-N 0.000 claims 2
- BBHMKMJQEYDGCR-UHFFFAOYSA-N 4-[3-[5-chloro-4-methyl-2-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]phenyl]-4-fluorobenzoyl]-1-methylpiperazin-2-one Chemical compound ClC=1C(=CC(=C(C=1)C=1C=C(C(=O)N2CC(N(CC2)C)=O)C=CC=1F)OCC1=NNC(N1C)=O)C BBHMKMJQEYDGCR-UHFFFAOYSA-N 0.000 claims 2
- ASCHHNZSTZOHGO-UHFFFAOYSA-N 4-tert-butyl-2-methyl-5-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]benzonitrile Chemical compound CN1C(=O)NN=C1COC1=CC(C#N)=C(C)C=C1C(C)(C)C ASCHHNZSTZOHGO-UHFFFAOYSA-N 0.000 claims 2
- ULYSSNIFDAUKCQ-UHFFFAOYSA-N 5-tert-butyl-2-methyl-4-(2H-pyrazolo[3,4-b]pyridin-3-ylmethoxy)benzonitrile Chemical compound C(C)(C)(C)C=1C(=CC(=C(C#N)C=1)C)OCC1=NNC2=NC=CC=C21 ULYSSNIFDAUKCQ-UHFFFAOYSA-N 0.000 claims 2
- GKEHAUWILITGHM-UHFFFAOYSA-N 5-tert-butyl-2-methyl-4-[(5-oxo-4-propan-2-yl-1H-1,2,4-triazol-3-yl)methoxy]benzonitrile Chemical compound CC(C)N1C(=O)NN=C1COC1=CC(C)=C(C=C1C(C)(C)C)C#N GKEHAUWILITGHM-UHFFFAOYSA-N 0.000 claims 2
- ONACPUZWLZTDIB-UHFFFAOYSA-N N-[[3-[5-chloro-4-methyl-2-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]phenyl]-4-fluorophenyl]methyl]-2-methoxy-N-methylacetamide Chemical compound COCC(=O)N(C)CC1=CC(=C(F)C=C1)C1=C(OCC2=NNC(=O)N2C)C=C(C)C(Cl)=C1 ONACPUZWLZTDIB-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- NULPPBXWYTZKHF-UHFFFAOYSA-N 1-[3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-6-yl]-2-methoxyethanone Chemical compound COCC(=O)N1CCC2=C(C1)NN=C2COC1=C(C=C(Cl)C(C)=C1)C(C)(C)C NULPPBXWYTZKHF-UHFFFAOYSA-N 0.000 claims 1
- OKKGZNISIPIACF-UHFFFAOYSA-N 1-[3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-6-yl]ethanone Chemical compound CC(=O)N1CCC2=C(C1)NN=C2COC1=C(C=C(Cl)C(C)=C1)C(C)(C)C OKKGZNISIPIACF-UHFFFAOYSA-N 0.000 claims 1
- VPWJOGXBWBNZPL-UHFFFAOYSA-N 1-[3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]-2-methoxyethanone Chemical compound COCC(=O)N1CCC2=C(C1)C(COC1=C(C=C(Cl)C(C)=C1)C(C)(C)C)=NN2 VPWJOGXBWBNZPL-UHFFFAOYSA-N 0.000 claims 1
- CMGUWPVLJVXYOT-UHFFFAOYSA-N 1-[3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]ethanone Chemical compound CC(=O)N1CCC2=C(C1)C(COC1=C(C=C(Cl)C(C)=C1)C(C)(C)C)=NN2 CMGUWPVLJVXYOT-UHFFFAOYSA-N 0.000 claims 1
- AERGWQGVDIYCBG-UHFFFAOYSA-N 1-[3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-2H-pyrazolo[3,4-d]pyrimidin-6-yl]azetidin-3-ol Chemical compound C(C)(C)(C)C1=C(OCC2=NNC3=NC(=NC=C32)N2CC(C2)O)C=C(C(=C1)Cl)C AERGWQGVDIYCBG-UHFFFAOYSA-N 0.000 claims 1
- DBXFSUQTZIJCPI-UHFFFAOYSA-N 1-[3-[[4-chloro-2-(2-methoxypyridin-3-yl)-5-methylphenoxy]methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-6-yl]ethanone Chemical compound ClC1=CC(=C(OCC2=NNC=3CN(CCC=32)C(C)=O)C=C1C)C=1C(=NC=CC=1)OC DBXFSUQTZIJCPI-UHFFFAOYSA-N 0.000 claims 1
- TZFOZOXOBZZVEM-UHFFFAOYSA-N 1-[[3-[5-chloro-4-methyl-2-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]phenyl]-4-fluorophenyl]methyl]-4-methylpiperazine-2,5-dione Chemical compound CN1C(=O)NN=C1COC1=C(C=C(Cl)C(C)=C1)C1=C(F)C=CC(CN2CC(=O)N(C)CC2=O)=C1 TZFOZOXOBZZVEM-UHFFFAOYSA-N 0.000 claims 1
- MSIAUZKPYAZWGU-UHFFFAOYSA-N 2-[5-chloro-4-methyl-2-[(6-oxo-1H-pyridazin-3-yl)methoxy]phenyl]-2-methylpropanenitrile Chemical compound ClC=1C(=CC(=C(C=1)C(C#N)(C)C)OCC1=NNC(C=C1)=O)C MSIAUZKPYAZWGU-UHFFFAOYSA-N 0.000 claims 1
- RCJZUQZYSHRPBH-UHFFFAOYSA-N 2-[[3-[(2-tert-butyl-4-chloro-5-fluorophenoxy)methyl]-2H-pyrazolo[3,4-b]pyridin-6-yl]-methylamino]ethanol Chemical compound C(C)(C)(C)C1=C(OCC2=NNC3=NC(=CC=C32)N(CCO)C)C=C(C(=C1)Cl)F RCJZUQZYSHRPBH-UHFFFAOYSA-N 0.000 claims 1
- MINOBEQBDXAMDG-UHFFFAOYSA-N 2-[[3-[(2-tert-butyl-4-chloro-5-fluorophenoxy)methyl]-2H-pyrazolo[3,4-b]pyridin-6-yl]amino]ethanol Chemical compound C(C)(C)(C)C1=C(OCC2=NNC3=NC(=CC=C32)NCCO)C=C(C(=C1)Cl)F MINOBEQBDXAMDG-UHFFFAOYSA-N 0.000 claims 1
- NPNNCUHJLLLTDY-UHFFFAOYSA-N 2-[[3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-2H-pyrazolo[3,4-b]pyridin-6-yl]-methylamino]ethanol Chemical compound C(C)(C)(C)C1=C(OCC2=NNC3=NC(=CC=C32)N(CCO)C)C=C(C(=C1)Cl)C NPNNCUHJLLLTDY-UHFFFAOYSA-N 0.000 claims 1
- VRBHNXBQBAYIAU-UHFFFAOYSA-N 2-[[3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-2H-pyrazolo[3,4-b]pyridin-6-yl]amino]ethanol Chemical compound C(C)(C)(C)C1=C(OCC2=NNC3=NC(=CC=C32)NCCO)C=C(C(=C1)Cl)C VRBHNXBQBAYIAU-UHFFFAOYSA-N 0.000 claims 1
- FNPAXPGBACPLDP-UHFFFAOYSA-N 2-[[3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-2H-pyrazolo[3,4-b]pyridin-6-yl]oxy]ethanol Chemical compound C(C)(C)(C)C1=C(OCC2=NNC3=NC(=CC=C32)OCCO)C=C(C(=C1)Cl)C FNPAXPGBACPLDP-UHFFFAOYSA-N 0.000 claims 1
- YDZJHPZOMGQHKQ-UHFFFAOYSA-N 2-[[3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-2H-pyrazolo[3,4-d]pyrimidin-6-yl]amino]ethanol Chemical compound C(C)(C)(C)C1=C(OCC2=NNC3=NC(=NC=C32)NCCO)C=C(C(=C1)Cl)C YDZJHPZOMGQHKQ-UHFFFAOYSA-N 0.000 claims 1
- FENFOADAIJEJSU-UHFFFAOYSA-N 2-[[3-[5-chloro-4-methyl-2-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]phenyl]benzoyl]amino]acetic acid Chemical compound CN1C(=O)NN=C1COC1=C(C=C(Cl)C(C)=C1)C1=CC=CC(=C1)C(=O)NCC(O)=O FENFOADAIJEJSU-UHFFFAOYSA-N 0.000 claims 1
- MAKMXKBKIQMCGC-UHFFFAOYSA-N 2-chloro-4-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]-5-[3-(morpholine-4-carbonyl)phenyl]benzonitrile Chemical compound CN1C(=O)NN=C1COC1=CC(Cl)=C(C=C1C1=CC(=CC=C1)C(=O)N1CCOCC1)C#N MAKMXKBKIQMCGC-UHFFFAOYSA-N 0.000 claims 1
- OHPHYVQRNLRIBV-UHFFFAOYSA-N 2-chloro-4-cyclopropyl-5-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]benzonitrile Chemical compound CN1C(=O)NN=C1COC1=CC(C#N)=C(Cl)C=C1C1CC1 OHPHYVQRNLRIBV-UHFFFAOYSA-N 0.000 claims 1
- LCDXFGQORUMHGS-UHFFFAOYSA-N 2-chloro-5-(2,3-difluorophenyl)-4-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]benzonitrile Chemical compound CN1C(=O)NN=C1COC1=CC(Cl)=C(C=C1C1=C(F)C(F)=CC=C1)C#N LCDXFGQORUMHGS-UHFFFAOYSA-N 0.000 claims 1
- YRZPCRCFLWPDQT-UHFFFAOYSA-N 2-chloro-5-(2,5-difluorophenyl)-4-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]benzonitrile Chemical compound CN1C(=O)NN=C1COC1=CC(Cl)=C(C=C1C1=C(F)C=CC(F)=C1)C#N YRZPCRCFLWPDQT-UHFFFAOYSA-N 0.000 claims 1
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- UIPOOZYTFCHLDN-UHFFFAOYSA-N 5-tert-butyl-4-[[6-(2-hydroxyethoxy)-2H-pyrazolo[3,4-d]pyrimidin-3-yl]methoxy]-2-methylbenzonitrile Chemical compound C(C)(C)(C)C=1C(=CC(=C(C#N)C=1)C)OCC1=NNC2=NC(=NC=C21)OCCO UIPOOZYTFCHLDN-UHFFFAOYSA-N 0.000 claims 1
- FOMXNMHVSOUGSW-UHFFFAOYSA-N 5-tert-butyl-4-[[6-(2-hydroxyethylamino)-2H-pyrazolo[3,4-d]pyrimidin-3-yl]methoxy]-2-methylbenzonitrile Chemical compound C(C)(C)(C)C=1C(=CC(=C(C#N)C=1)C)OCC1=NNC2=NC(=NC=C21)NCCO FOMXNMHVSOUGSW-UHFFFAOYSA-N 0.000 claims 1
- XDXMQOOGQOACMH-UHFFFAOYSA-N 5-tert-butyl-4-[[6-(3-hydroxyazetidin-1-yl)-2H-pyrazolo[3,4-d]pyrimidin-3-yl]methoxy]-2-methylbenzonitrile Chemical compound C(C)(C)(C)C=1C(=CC(=C(C#N)C=1)C)OCC1=NNC2=NC(=NC=C21)N1CC(C1)O XDXMQOOGQOACMH-UHFFFAOYSA-N 0.000 claims 1
- OIKCZWAGXIDCAS-UHFFFAOYSA-N 5-tert-butyl-4-[[6-[2,3-dihydroxypropyl(methyl)amino]-2H-pyrazolo[3,4-d]pyrimidin-3-yl]methoxy]-2-methylbenzonitrile Chemical compound C(C)(C)(C)C=1C(=CC(=C(C#N)C=1)C)OCC1=NNC2=NC(=NC=C21)N(C)CC(CO)O OIKCZWAGXIDCAS-UHFFFAOYSA-N 0.000 claims 1
- USKGMLCKFACRFD-UHFFFAOYSA-N 5-tert-butyl-4-[[6-[2-hydroxyethyl(methyl)amino]-2H-pyrazolo[3,4-d]pyrimidin-3-yl]methoxy]-2-methylbenzonitrile Chemical compound C(C)(C)(C)C=1C(=CC(=C(C#N)C=1)C)OCC1=NNC2=NC(=NC=C21)N(C)CCO USKGMLCKFACRFD-UHFFFAOYSA-N 0.000 claims 1
- FKZSPXKEEMIWLJ-UHFFFAOYSA-N 7-[5-chloro-4-methyl-2-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]phenyl]-6-fluoro-3-methyl-1,3-benzoxazol-2-one Chemical compound CN1C(=O)NN=C1COC1=C(C=C(Cl)C(C)=C1)C1=C(F)C=CC2=C1OC(=O)N2C FKZSPXKEEMIWLJ-UHFFFAOYSA-N 0.000 claims 1
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- PVWDMRVRPVYPLA-UHFFFAOYSA-N CC(C)C1=C(OCC2=NNC3=C2C=CC=N3)C=C(C)C(Cl)=C1 Chemical compound CC(C)C1=C(OCC2=NNC3=C2C=CC=N3)C=C(C)C(Cl)=C1 PVWDMRVRPVYPLA-UHFFFAOYSA-N 0.000 claims 1
- SYNONXVGXQVZPV-UHFFFAOYSA-N CN1C(=O)NN=C1COC1=C(C=C(C=C1)C1=CN=CN1COCC[Si](C)(C)C)C(C)(C)C Chemical compound CN1C(=O)NN=C1COC1=C(C=C(C=C1)C1=CN=CN1COCC[Si](C)(C)C)C(C)(C)C SYNONXVGXQVZPV-UHFFFAOYSA-N 0.000 claims 1
- OMBXJKSIQMTBRM-UHFFFAOYSA-N CN1C(=O)NN=C1COC1=C(C=C(C=C1)C1=NC=CN1COCC[Si](C)(C)C)C(C)(C)C Chemical compound CN1C(=O)NN=C1COC1=C(C=C(C=C1)C1=NC=CN1COCC[Si](C)(C)C)C(C)(C)C OMBXJKSIQMTBRM-UHFFFAOYSA-N 0.000 claims 1
- HWYHRGGKBRDYCH-UHFFFAOYSA-N ClC=1C(=CC(=C(C1)C=1C=C(C(=O)NCCC)C=CC1)OCC1=NNC(N1C)=O)C Chemical compound ClC=1C(=CC(=C(C1)C=1C=C(C(=O)NCCC)C=CC1)OCC1=NNC(N1C)=O)C HWYHRGGKBRDYCH-UHFFFAOYSA-N 0.000 claims 1
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- NWPBWZFANGAMNR-UHFFFAOYSA-N N-[[3-[5-chloro-4-methyl-2-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]phenyl]-4-fluorophenyl]methyl]-N-methylcyclopropanecarboxamide Chemical compound CN(CC1=CC(=C(F)C=C1)C1=C(OCC2=NNC(=O)N2C)C=C(C)C(Cl)=C1)C(=O)C1CC1 NWPBWZFANGAMNR-UHFFFAOYSA-N 0.000 claims 1
- DSAJVCRVEWPOOK-UHFFFAOYSA-N N-[[3-[5-chloro-4-methyl-2-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]phenyl]-4-fluorophenyl]methyl]cyclopropanecarboxamide Chemical compound CN1C(=O)NN=C1COC1=C(C=C(Cl)C(C)=C1)C1=C(F)C=CC(CNC(=O)C2CC2)=C1 DSAJVCRVEWPOOK-UHFFFAOYSA-N 0.000 claims 1
- 239000004146 Propane-1,2-diol Substances 0.000 claims 1
- JOUPXYVEMKXTJC-UHFFFAOYSA-N [3-[5-chloro-4-methyl-2-(2H-pyrazolo[3,4-b]pyridin-3-ylmethoxy)phenyl]-4-fluorophenyl]-morpholin-4-ylmethanone Chemical compound ClC=1C(=CC(=C(C=1)C=1C=C(C=CC=1F)C(=O)N1CCOCC1)OCC1=NNC2=NC=CC=C21)C JOUPXYVEMKXTJC-UHFFFAOYSA-N 0.000 claims 1
- HXYBFHRVAKKOIQ-UHFFFAOYSA-N [3-[5-chloro-4-methyl-2-(2H-pyrazolo[3,4-b]pyridin-3-ylmethoxy)phenyl]-4-fluorophenyl]-pyrrolidin-1-ylmethanone Chemical compound ClC=1C(=CC(=C(C=1)C=1C=C(C=CC=1F)C(=O)N1CCCC1)OCC1=NNC2=NC=CC=C21)C HXYBFHRVAKKOIQ-UHFFFAOYSA-N 0.000 claims 1
- CELGLULPTRDPIZ-UHFFFAOYSA-N [3-[5-chloro-4-methyl-2-(2H-pyrazolo[3,4-b]pyridin-3-ylmethoxy)phenyl]phenyl]-morpholin-4-ylmethanone Chemical compound ClC=1C(=CC(=C(C=1)C=1C=C(C=CC=1)C(=O)N1CCOCC1)OCC1=NNC2=NC=CC=C21)C CELGLULPTRDPIZ-UHFFFAOYSA-N 0.000 claims 1
- WOFONVHGRJJMHY-UHFFFAOYSA-N [5-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-1H-pyrazol-3-yl]-pyrrolidin-1-ylmethanone Chemical compound C(C)(C)(C)C1=C(OCC2=NNC(=C2)C(=O)N2CCCC2)C=C(C(=C1)Cl)C WOFONVHGRJJMHY-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
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- OEAFWZXMSVBSAW-UHFFFAOYSA-N methyl 3-[5-chloro-4-methyl-2-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]phenyl]-4-methylbenzoate Chemical compound COC(=O)C1=CC(=C(C)C=C1)C1=C(OCC2=NNC(=O)N2C)C=C(C)C(Cl)=C1 OEAFWZXMSVBSAW-UHFFFAOYSA-N 0.000 claims 1
- OUJPIWPIMKNSOD-UHFFFAOYSA-N methyl 3-[5-chloro-4-methyl-2-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methoxy]phenyl]benzoate Chemical compound COC(=O)C1=CC(=CC=C1)C1=C(OCC2=NNC(=O)N2C)C=C(C)C(Cl)=C1 OUJPIWPIMKNSOD-UHFFFAOYSA-N 0.000 claims 1
- HHDLQXVHINBZGY-UHFFFAOYSA-N methyl 5-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-1H-pyrazole-3-carboxylate Chemical compound C(C)(C)(C)C1=C(OCC2=NNC(=C2)C(=O)OC)C=C(C(=C1)Cl)C HHDLQXVHINBZGY-UHFFFAOYSA-N 0.000 claims 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
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- AEKYEOXDOBSHHC-UHFFFAOYSA-N tert-butyl 3-[(2-tert-butyl-4-chloro-5-methylphenoxy)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine-5-carboxylate Chemical compound C(C)(C)(C)C1=C(OCC2=NNC3=C2CN(CC3)C(=O)OC(C)(C)C)C=C(C(=C1)Cl)C AEKYEOXDOBSHHC-UHFFFAOYSA-N 0.000 claims 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
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| US10793571B2 (en) | 2014-01-31 | 2020-10-06 | Dana-Farber Cancer Institute, Inc. | Uses of diazepane derivatives |
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| EA037928B1 (ru) | 2014-03-26 | 2021-06-08 | Ф. Хоффманн-Ля Рош Аг | Бициклические соединения в качестве ингибиторов продукции аутотаксина (atx) и лизофосфатидиловой кислоты (lpa) |
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| RU2742035C2 (ru) | 2015-11-25 | 2021-02-01 | Дана-Фарбер Кэнсер Инститьют, Инк. | Бивалентные ингибиторы бромодоменов и пути их применения |
| JP7090099B2 (ja) | 2017-03-16 | 2022-06-23 | エフ．ホフマン－ラ ロシュ アーゲー | Ａｔｘインヒビターとしての新規二環式化合物 |
| BR112019019017A2 (pt) | 2017-03-16 | 2020-04-14 | Hoffmann La Roche | compostos heterocíclicos de utilidade como inibidores duplos de atx/ca |
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| JP7044011B2 (ja) * | 2017-09-13 | 2022-03-30 | 信越化学工業株式会社 | 重合性単量体、重合体、レジスト材料、及びパターン形成方法 |
| CN114181088B (zh) * | 2021-12-21 | 2024-05-17 | 大连大学 | 一种离子液体[TEA][TfOH]2催化制备α-卤代苯乙酮类化合物的方法 |
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