JP2013518864A5 - - Google Patents
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- JP2013518864A5 JP2013518864A5 JP2012551647A JP2012551647A JP2013518864A5 JP 2013518864 A5 JP2013518864 A5 JP 2013518864A5 JP 2012551647 A JP2012551647 A JP 2012551647A JP 2012551647 A JP2012551647 A JP 2012551647A JP 2013518864 A5 JP2013518864 A5 JP 2013518864A5
- Authority
- JP
- Japan
- Prior art keywords
- amine
- triazin
- compound
- formula
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 61
- 125000000217 alkyl group Chemical group 0.000 claims 36
- 229910052736 halogen Inorganic materials 0.000 claims 33
- 150000002367 halogens Chemical class 0.000 claims 32
- 125000001424 substituent group Chemical group 0.000 claims 29
- 125000003118 aryl group Chemical group 0.000 claims 18
- 238000000034 method Methods 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 238000006243 chemical reaction Methods 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- -1 iodo, bromo, chloro, fluoro, ethyl Chemical group 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 229910001507 metal halide Inorganic materials 0.000 claims 4
- 150000005309 metal halides Chemical class 0.000 claims 4
- 150000001282 organosilanes Chemical class 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 206010016654 Fibrosis Diseases 0.000 claims 3
- 208000019425 cirrhosis of liver Diseases 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 3
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- UGXUMFRCOJMAJB-UHFFFAOYSA-N 6-(2,6-dimethylpyridin-4-yl)-5-(4-methoxyphenyl)-1,2,4-triazin-3-amine Chemical compound C1=CC(OC)=CC=C1C1=NC(N)=NN=C1C1=CC(C)=NC(C)=C1 UGXUMFRCOJMAJB-UHFFFAOYSA-N 0.000 claims 2
- NCWQLHHDGDXIJN-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC(F)=CC=2)=C1 NCWQLHHDGDXIJN-UHFFFAOYSA-N 0.000 claims 2
- NDFNRBWLVZWETQ-UHFFFAOYSA-N 6-[2-methyl-6-(trifluoromethyl)pyridin-4-yl]-5-phenyl-1,2,4-triazin-3-amine Chemical compound FC(F)(F)C1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC=CC=2)=C1 NDFNRBWLVZWETQ-UHFFFAOYSA-N 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 206010030113 Oedema Diseases 0.000 claims 2
- 230000007882 cirrhosis Effects 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- SOWQISGNRVOGHI-UHFFFAOYSA-N 4-(3-amino-5-phenyl-1,2,4-triazin-6-yl)-6-methylpyridine-2-carbonitrile Chemical compound N#CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC=CC=2)=C1 SOWQISGNRVOGHI-UHFFFAOYSA-N 0.000 claims 1
- HYEQJOQXBRKLLW-UHFFFAOYSA-N 4-[3-amino-6-(2,6-dimethylpyridin-4-yl)-1,2,4-triazin-5-yl]benzonitrile Chemical compound CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC(=CC=2)C#N)=C1 HYEQJOQXBRKLLW-UHFFFAOYSA-N 0.000 claims 1
- POMJRWRHFHAUKX-UHFFFAOYSA-N 4-[3-amino-6-(2-chloro-6-methylpyridin-4-yl)-1,2,4-triazin-5-yl]benzonitrile Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC(=CC=2)C#N)=C1 POMJRWRHFHAUKX-UHFFFAOYSA-N 0.000 claims 1
- KGJDKXDMUVZONK-UHFFFAOYSA-N 4-[3-amino-6-(2-chloropyridin-4-yl)-1,2,4-triazin-5-yl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C1=NC(N)=NN=C1C1=CC=NC(Cl)=C1 KGJDKXDMUVZONK-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- NDFYLHNFBGRTPI-UHFFFAOYSA-N 5-(2,5-difluorophenyl)-6-(2,6-dimethylpyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C(=CC=C(F)C=2)F)=C1 NDFYLHNFBGRTPI-UHFFFAOYSA-N 0.000 claims 1
- JAOUPVRUDZWXSA-UHFFFAOYSA-N 5-(2,5-difluorophenyl)-6-[2-methyl-6-(trifluoromethyl)pyridin-4-yl]-1,2,4-triazin-3-amine Chemical compound FC(F)(F)C1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C(=CC=C(F)C=2)F)=C1 JAOUPVRUDZWXSA-UHFFFAOYSA-N 0.000 claims 1
- OQEVFJKDYFGXON-UHFFFAOYSA-N 5-(3,4-difluorophenyl)-6-(2,6-dimethylpyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(F)C(F)=CC=2)=C1 OQEVFJKDYFGXON-UHFFFAOYSA-N 0.000 claims 1
- XRNSGSPRIGXHLC-UHFFFAOYSA-N 5-(3,4-difluorophenyl)-6-[2-methyl-6-(trifluoromethyl)pyridin-4-yl]-1,2,4-triazin-3-amine Chemical compound FC(F)(F)C1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(F)C(F)=CC=2)=C1 XRNSGSPRIGXHLC-UHFFFAOYSA-N 0.000 claims 1
- ZEBNSCYTUBSYES-UHFFFAOYSA-N 5-(3,5-difluorophenyl)-6-(2,6-dimethylpyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(F)C=C(F)C=2)=C1 ZEBNSCYTUBSYES-UHFFFAOYSA-N 0.000 claims 1
- GFMUOQKWAOPGFP-UHFFFAOYSA-N 5-(3,5-difluorophenyl)-6-[2-methyl-6-(trifluoromethyl)pyridin-4-yl]-1,2,4-triazin-3-amine Chemical compound FC(F)(F)C1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(F)C=C(F)C=2)=C1 GFMUOQKWAOPGFP-UHFFFAOYSA-N 0.000 claims 1
- KODCJAODHLEPNZ-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-6-(2,6-dimethylpyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(Cl)C(F)=CC=2)=C1 KODCJAODHLEPNZ-UHFFFAOYSA-N 0.000 claims 1
- MVPSTPVPJUPGMO-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-6-(2-chloro-6-methylpyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(Cl)C(F)=CC=2)=C1 MVPSTPVPJUPGMO-UHFFFAOYSA-N 0.000 claims 1
- ZCBKSRODPBSBET-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-6-(2-chloropyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound C=1C=C(F)C(Cl)=CC=1C1=NC(N)=NN=C1C1=CC=NC(Cl)=C1 ZCBKSRODPBSBET-UHFFFAOYSA-N 0.000 claims 1
- HBEJNXVXUQQCSX-UHFFFAOYSA-N 5-(3-chloro-5-fluorophenyl)-6-(2-chloro-6-methylpyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(Cl)C=C(F)C=2)=C1 HBEJNXVXUQQCSX-UHFFFAOYSA-N 0.000 claims 1
- OBGGARAXMYJZAS-UHFFFAOYSA-N 5-(3-chloro-5-fluorophenyl)-6-(2-chloropyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound C=1C(F)=CC(Cl)=CC=1C1=NC(N)=NN=C1C1=CC=NC(Cl)=C1 OBGGARAXMYJZAS-UHFFFAOYSA-N 0.000 claims 1
- TWDZXVRAJIOMBP-UHFFFAOYSA-N 5-(3-chlorophenyl)-6-(2,6-dimethylpyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(Cl)C=CC=2)=C1 TWDZXVRAJIOMBP-UHFFFAOYSA-N 0.000 claims 1
- XZSDECOAWFOPHX-UHFFFAOYSA-N 5-(3-chlorophenyl)-6-(2-chloropyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound C=1C=CC(Cl)=CC=1C1=NC(N)=NN=C1C1=CC=NC(Cl)=C1 XZSDECOAWFOPHX-UHFFFAOYSA-N 0.000 claims 1
- MGXHKBBXSDUHHZ-UHFFFAOYSA-N 5-(3-fluorophenyl)-6-[2-methyl-6-(trifluoromethyl)pyridin-4-yl]-1,2,4-triazin-3-amine Chemical compound FC(F)(F)C1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(F)C=CC=2)=C1 MGXHKBBXSDUHHZ-UHFFFAOYSA-N 0.000 claims 1
- FQGPESZLQLSFSS-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,6-dimethylpyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC(Cl)=CC=2)=C1 FQGPESZLQLSFSS-UHFFFAOYSA-N 0.000 claims 1
- WZXQIQDUXLCJGU-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2-chloropyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound C=1C=C(Cl)C=CC=1C1=NC(N)=NN=C1C1=CC=NC(Cl)=C1 WZXQIQDUXLCJGU-UHFFFAOYSA-N 0.000 claims 1
- GIFJFWNMMFGQLP-UHFFFAOYSA-N 5-(4-fluorophenyl)-6-[2-methyl-6-(trifluoromethyl)pyridin-4-yl]-1,2,4-triazin-3-amine Chemical compound FC(F)(F)C1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC(F)=CC=2)=C1 GIFJFWNMMFGQLP-UHFFFAOYSA-N 0.000 claims 1
- NJGFTLXHHISHQB-UHFFFAOYSA-N 5-[4-(difluoromethoxy)phenyl]-6-(2,6-dimethylpyridin-4-yl)-1,2,4-triazin-3-amine Chemical compound CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC(OC(F)F)=CC=2)=C1 NJGFTLXHHISHQB-UHFFFAOYSA-N 0.000 claims 1
- WPMGQNHDTMWLTF-UHFFFAOYSA-N 5-phenyl-6-[2-(trifluoromethyl)pyridin-4-yl]-1,2,4-triazin-3-amine Chemical compound C=1C=CC=CC=1C1=NC(N)=NN=C1C1=CC=NC(C(F)(F)F)=C1 WPMGQNHDTMWLTF-UHFFFAOYSA-N 0.000 claims 1
- VPYMIAUKWOSXCL-UHFFFAOYSA-N 6-(2,6-dichloropyridin-4-yl)-5-phenyl-1,2,4-triazin-3-amine Chemical compound C=1C=CC=CC=1C1=NC(N)=NN=C1C1=CC(Cl)=NC(Cl)=C1 VPYMIAUKWOSXCL-UHFFFAOYSA-N 0.000 claims 1
- BWIRCKWZMRMDQC-UHFFFAOYSA-N 6-(2,6-dimethoxypyridin-4-yl)-5-phenyl-1,2,4-triazin-3-amine Chemical compound COC1=NC(OC)=CC(C=2C(=NC(N)=NN=2)C=2C=CC=CC=2)=C1 BWIRCKWZMRMDQC-UHFFFAOYSA-N 0.000 claims 1
- MOPWVSDFQNVWJU-UHFFFAOYSA-N 6-(2,6-dimethylpyridin-4-yl)-5-(2-fluorophenyl)-1,2,4-triazin-3-amine Chemical compound CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C(=CC=CC=2)F)=C1 MOPWVSDFQNVWJU-UHFFFAOYSA-N 0.000 claims 1
- LYVNVEJCGRVTLE-UHFFFAOYSA-N 6-(2,6-dimethylpyridin-4-yl)-5-(3-fluorophenyl)-1,2,4-triazin-3-amine Chemical compound CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(F)C=CC=2)=C1 LYVNVEJCGRVTLE-UHFFFAOYSA-N 0.000 claims 1
- NEYZTILMBRSITP-UHFFFAOYSA-N 6-(2,6-dimethylpyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine Chemical compound CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC(F)=CC=2)=C1 NEYZTILMBRSITP-UHFFFAOYSA-N 0.000 claims 1
- XMBOSJIVXCXUSA-UHFFFAOYSA-N 6-(2,6-dimethylpyridin-4-yl)-5-[4-(methoxymethyl)phenyl]-1,2,4-triazin-3-amine Chemical compound C1=CC(COC)=CC=C1C1=NC(N)=NN=C1C1=CC(C)=NC(C)=C1 XMBOSJIVXCXUSA-UHFFFAOYSA-N 0.000 claims 1
- SORFNYWLKDSNNF-UHFFFAOYSA-N 6-(2,6-dimethylpyridin-4-yl)-5-phenyl-1,2,4-triazin-3-amine Chemical compound CC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC=CC=2)=C1 SORFNYWLKDSNNF-UHFFFAOYSA-N 0.000 claims 1
- ICKLVGVENQMCQO-UHFFFAOYSA-N 6-(2-bromo-6-methylpyridin-4-yl)-5-phenyl-1,2,4-triazin-3-amine Chemical compound BrC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC=CC=2)=C1 ICKLVGVENQMCQO-UHFFFAOYSA-N 0.000 claims 1
- CJMZQEWZWDXVRC-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-(2,5-difluorophenyl)-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C(=CC=C(F)C=2)F)=C1 CJMZQEWZWDXVRC-UHFFFAOYSA-N 0.000 claims 1
- RJOBHNRSFMJGBB-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-(2-fluorophenyl)-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C(=CC=CC=2)F)=C1 RJOBHNRSFMJGBB-UHFFFAOYSA-N 0.000 claims 1
- JSKUKFZJLSYWLH-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-(3,4-difluorophenyl)-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(F)C(F)=CC=2)=C1 JSKUKFZJLSYWLH-UHFFFAOYSA-N 0.000 claims 1
- SDJUPUNTYMJDBL-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-(3,5-difluorophenyl)-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(F)C=C(F)C=2)=C1 SDJUPUNTYMJDBL-UHFFFAOYSA-N 0.000 claims 1
- WCHBVPNJEUPNLD-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-(3-chlorophenyl)-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(Cl)C=CC=2)=C1 WCHBVPNJEUPNLD-UHFFFAOYSA-N 0.000 claims 1
- NORPSLFVKUSIOR-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-(3-fluorophenyl)-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=C(F)C=CC=2)=C1 NORPSLFVKUSIOR-UHFFFAOYSA-N 0.000 claims 1
- GOFKXHQTEKOHKH-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-(4-chlorophenyl)-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC(Cl)=CC=2)=C1 GOFKXHQTEKOHKH-UHFFFAOYSA-N 0.000 claims 1
- BUYKIYJEWFLQDO-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-(4-ethylphenyl)-1,2,4-triazin-3-amine Chemical compound C1=CC(CC)=CC=C1C1=NC(N)=NN=C1C1=CC(C)=NC(Cl)=C1 BUYKIYJEWFLQDO-UHFFFAOYSA-N 0.000 claims 1
- XUYLTZGULLLIQX-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-(4-methoxyphenyl)-1,2,4-triazin-3-amine Chemical compound C1=CC(OC)=CC=C1C1=NC(N)=NN=C1C1=CC(C)=NC(Cl)=C1 XUYLTZGULLLIQX-UHFFFAOYSA-N 0.000 claims 1
- PGVDAXDXGMHLIG-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-[4-(difluoromethoxy)phenyl]-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC(OC(F)F)=CC=2)=C1 PGVDAXDXGMHLIG-UHFFFAOYSA-N 0.000 claims 1
- XSTWQDKQDRKLPO-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-[4-(methoxymethyl)phenyl]-1,2,4-triazin-3-amine Chemical compound C1=CC(COC)=CC=C1C1=NC(N)=NN=C1C1=CC(C)=NC(Cl)=C1 XSTWQDKQDRKLPO-UHFFFAOYSA-N 0.000 claims 1
- CIQKMAODEOFLCF-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-phenyl-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC=CC=2)=C1 CIQKMAODEOFLCF-UHFFFAOYSA-N 0.000 claims 1
- HAENFNNSNQPFQE-UHFFFAOYSA-N 6-(2-chloropyridin-4-yl)-5-(3,4-difluorophenyl)-1,2,4-triazin-3-amine Chemical compound C=1C=C(F)C(F)=CC=1C1=NC(N)=NN=C1C1=CC=NC(Cl)=C1 HAENFNNSNQPFQE-UHFFFAOYSA-N 0.000 claims 1
- PTBQHSARCBJAMT-UHFFFAOYSA-N 6-(2-chloropyridin-4-yl)-5-(3,5-difluorophenyl)-1,2,4-triazin-3-amine Chemical compound C=1C(F)=CC(F)=CC=1C1=NC(N)=NN=C1C1=CC=NC(Cl)=C1 PTBQHSARCBJAMT-UHFFFAOYSA-N 0.000 claims 1
- SCDWWFBKAMKVAF-UHFFFAOYSA-N 6-(2-chloropyridin-4-yl)-5-(3-fluorophenyl)-1,2,4-triazin-3-amine Chemical compound C=1C=CC(F)=CC=1C1=NC(N)=NN=C1C1=CC=NC(Cl)=C1 SCDWWFBKAMKVAF-UHFFFAOYSA-N 0.000 claims 1
- MALOBNCQXFPQDA-UHFFFAOYSA-N 6-(2-chloropyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine Chemical compound C=1C=C(F)C=CC=1C1=NC(N)=NN=C1C1=CC=NC(Cl)=C1 MALOBNCQXFPQDA-UHFFFAOYSA-N 0.000 claims 1
- QPJLFPLPXAJKPR-UHFFFAOYSA-N 6-(2-chloropyridin-4-yl)-5-[4-(difluoromethoxy)phenyl]-1,2,4-triazin-3-amine Chemical compound C=1C=C(OC(F)F)C=CC=1C1=NC(N)=NN=C1C1=CC=NC(Cl)=C1 QPJLFPLPXAJKPR-UHFFFAOYSA-N 0.000 claims 1
- MYYJQEFMDPUOKW-UHFFFAOYSA-N 6-(2-chloropyridin-4-yl)-5-[4-(methoxymethyl)phenyl]-1,2,4-triazin-3-amine Chemical compound C1=CC(COC)=CC=C1C1=NC(N)=NN=C1C1=CC=NC(Cl)=C1 MYYJQEFMDPUOKW-UHFFFAOYSA-N 0.000 claims 1
- ZTSZQPMGKAVFFY-UHFFFAOYSA-N 6-(2-cyclopropyl-6-methylpyridin-4-yl)-5-phenyl-1,2,4-triazin-3-amine Chemical compound N=1C(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC=CC=2)=CC=1C1CC1 ZTSZQPMGKAVFFY-UHFFFAOYSA-N 0.000 claims 1
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| US10373702B2 (en) | 2014-03-27 | 2019-08-06 | Massachusetts Institute Of Technology | Water-soluble trans-membrane proteins and methods for the preparation and use thereof |
| US10184794B2 (en) * | 2015-07-01 | 2019-01-22 | Makita Corporation | Laser marker |
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| CN108467386B (zh) * | 2017-02-23 | 2020-11-17 | 江苏恒瑞医药股份有限公司 | 稠杂芳基取代的1,2,4-三嗪-3-胺类衍生物、其制备方法及其在医药上的应用 |
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