JP2018535211A5 - - Google Patents
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- JP2018535211A5 JP2018535211A5 JP2018521424A JP2018521424A JP2018535211A5 JP 2018535211 A5 JP2018535211 A5 JP 2018535211A5 JP 2018521424 A JP2018521424 A JP 2018521424A JP 2018521424 A JP2018521424 A JP 2018521424A JP 2018535211 A5 JP2018535211 A5 JP 2018535211A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- group
- halogen atoms
- 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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- 125000005843 halogen group Chemical group 0.000 claims 86
- -1 substituted Chemical group 0.000 claims 57
- 150000001875 compounds Chemical class 0.000 claims 38
- 125000000623 heterocyclic group Chemical group 0.000 claims 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 27
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 20
- 125000003107 substituted aryl group Chemical group 0.000 claims 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 229910052801 chlorine Inorganic materials 0.000 claims 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims 10
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000004414 alkyl thio group Chemical group 0.000 claims 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 8
- 125000001769 aryl amino group Chemical group 0.000 claims 8
- 229910052740 iodine Inorganic materials 0.000 claims 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 7
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 3
- COERJHDMQUPDCV-UHFFFAOYSA-N [K].FB(F)F Chemical compound [K].FB(F)F COERJHDMQUPDCV-UHFFFAOYSA-N 0.000 claims 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 229910052710 silicon Inorganic materials 0.000 claims 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 3
- GRHIDHWBYWHNTE-UHFFFAOYSA-N 2-(2-bromo-6-trimethylsilylphenoxy)-1-phenylethanone Chemical compound C[Si](C)(C)C1=CC=CC(Br)=C1OCC(=O)C1=CC=CC=C1 GRHIDHWBYWHNTE-UHFFFAOYSA-N 0.000 claims 2
- SBTFJARTUNGFKQ-UHFFFAOYSA-N 2-(2-chlorophenyl)sulfanyl-3-(trifluoromethyl)quinoxaline Chemical compound FC(F)(F)C1=NC2=CC=CC=C2N=C1SC1=CC=CC=C1Cl SBTFJARTUNGFKQ-UHFFFAOYSA-N 0.000 claims 2
- VPICYQMLAJLTFJ-UHFFFAOYSA-N 2-(2-chlorophenyl)sulfanylquinoxaline Chemical compound ClC1=CC=CC=C1SC1=CN=C(C=CC=C2)C2=N1 VPICYQMLAJLTFJ-UHFFFAOYSA-N 0.000 claims 2
- VIPZARLHTWEWQV-UHFFFAOYSA-N 2-(4-chloro-3-fluorophenoxy)-3-methylquinoxaline Chemical compound CC1=NC2=CC=CC=C2N=C1OC1=CC=C(Cl)C(F)=C1 VIPZARLHTWEWQV-UHFFFAOYSA-N 0.000 claims 2
- OJHZEIGCCAXUOU-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]phenol Chemical compound CC(C)(C)[Si](C)(C)C1=CC=CC=C1O OJHZEIGCCAXUOU-UHFFFAOYSA-N 0.000 claims 2
- RHLITNIJIBAVSN-UHFFFAOYSA-N 2-trimethylsilylaniline Chemical compound C[Si](C)(C)C1=CC=CC=C1N RHLITNIJIBAVSN-UHFFFAOYSA-N 0.000 claims 2
- UIGHARXPLDWFHA-UHFFFAOYSA-N 2-trimethylsilylphenol Chemical compound C[Si](C)(C)C1=CC=CC=C1O UIGHARXPLDWFHA-UHFFFAOYSA-N 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- PQFMANPGRJDQIK-UHFFFAOYSA-N [2-(bromomethyl)phenyl]-trimethylsilane Chemical compound C[Si](C)(C)C1=CC=CC=C1CBr PQFMANPGRJDQIK-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 244000005700 microbiome Species 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- AFVGFIXUVDWZOU-UHFFFAOYSA-N 2-(2-bromophenoxy)quinoxaline Chemical compound BrC1=CC=CC=C1OC1=CN=C(C=CC=C2)C2=N1 AFVGFIXUVDWZOU-UHFFFAOYSA-N 0.000 claims 1
- IZJNRKYNSZUORE-UHFFFAOYSA-N 2-(2-chlorophenoxy)-3-methylquinoxaline Chemical compound ClC1=C(OC2=NC3=CC=CC=C3N=C2C)C=CC=C1 IZJNRKYNSZUORE-UHFFFAOYSA-N 0.000 claims 1
- ARCKHELLSLDRAW-UHFFFAOYSA-N 2-(2-chlorophenoxy)quinoxaline Chemical compound ClC1=CC=CC=C1OC1=CN=C(C=CC=C2)C2=N1 ARCKHELLSLDRAW-UHFFFAOYSA-N 0.000 claims 1
- DLNJYONCSYDYHP-UHFFFAOYSA-N 2-(2-iodophenoxy)quinoxaline Chemical compound IC1=CC=CC=C1OC1=CN=C(C=CC=C2)C2=N1 DLNJYONCSYDYHP-UHFFFAOYSA-N 0.000 claims 1
- YZIHUTNZHQHRDZ-UHFFFAOYSA-N 2-(2-trimethylsilylphenoxy)acetic acid Chemical compound C[Si](C1=C(OCC(=O)O)C=CC=C1)(C)C YZIHUTNZHQHRDZ-UHFFFAOYSA-N 0.000 claims 1
- FRJFXCDARSSCIW-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]quinoxaline Chemical compound ClC1=C(CC2=NC3=CC=CC=C3N=C2)C=CC=C1 FRJFXCDARSSCIW-UHFFFAOYSA-N 0.000 claims 1
- JASHIXJOSSPJLH-UHFFFAOYSA-N 2-[(2-hydroxyphenyl)-dimethylsilyl]phenol Chemical compound C=1C=CC=C(O)C=1[Si](C)(C)C1=CC=CC=C1O JASHIXJOSSPJLH-UHFFFAOYSA-N 0.000 claims 1
- VLSILSGMSUGMSL-UHFFFAOYSA-N 2-[(2-methylquinolin-3-yl)methyl]aniline Chemical compound CC1=NC2=CC=CC=C2C=C1CC1=C(N)C=CC=C1 VLSILSGMSUGMSL-UHFFFAOYSA-N 0.000 claims 1
- XRQYCBXQALAYNF-UHFFFAOYSA-N 2-[dimethyl(phenyl)silyl]aniline Chemical compound C[Si](C1=C(N)C=CC=C1)(C1=CC=CC=C1)C XRQYCBXQALAYNF-UHFFFAOYSA-N 0.000 claims 1
- OPDYOJOLRCBQOQ-UHFFFAOYSA-N 2-[dimethyl-(2-sulfanylphenyl)silyl]benzenethiol Chemical compound C=1C=CC=C(S)C=1[Si](C)(C)C1=CC=CC=C1S OPDYOJOLRCBQOQ-UHFFFAOYSA-N 0.000 claims 1
- REROUWZNNUEWRP-UHFFFAOYSA-N 2-[heptyl(dimethyl)silyl]aniline Chemical compound C(CCCCCC)[Si](C1=C(N)C=CC=C1)(C)C REROUWZNNUEWRP-UHFFFAOYSA-N 0.000 claims 1
- IHUMAESRTZIKQI-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]benzenethiol Chemical compound CC(C)(C)[Si](C)(C)C1=CC=CC=C1S IHUMAESRTZIKQI-UHFFFAOYSA-N 0.000 claims 1
- XAGKTNPAZCBEAF-UHFFFAOYSA-N 2-bromo-3-(2-bromo-4-chlorophenoxy)quinoxaline Chemical compound BrC1=NC2=CC=CC=C2N=C1OC1=C(C=C(C=C1)Cl)Br XAGKTNPAZCBEAF-UHFFFAOYSA-N 0.000 claims 1
- XHSXPOYUWDZDEE-UHFFFAOYSA-N 2-bromo-3-(2-bromo-4-chlorophenyl)sulfanylquinoxaline Chemical compound BrC1=NC2=CC=CC=C2N=C1SC1=C(C=C(C=C1)Cl)Br XHSXPOYUWDZDEE-UHFFFAOYSA-N 0.000 claims 1
- PXIWXVBZBAOAQW-UHFFFAOYSA-N 2-chloro-3-[(2-chlorophenyl)methyl]-6-fluoroquinoline Chemical compound C=1C2=CC(F)=CC=C2N=C(Cl)C=1CC1=CC=CC=C1Cl PXIWXVBZBAOAQW-UHFFFAOYSA-N 0.000 claims 1
- CTOWVTDBOAORDR-UHFFFAOYSA-N 2-chloro-3-[(2-chlorophenyl)methyl]quinoline Chemical compound ClC1=CC=CC=C1CC1=CC2=CC=CC=C2N=C1Cl CTOWVTDBOAORDR-UHFFFAOYSA-N 0.000 claims 1
- MVXWAQWKJLMULU-UHFFFAOYSA-N 2-chloro-6-(8-fluoroquinolin-3-yl)oxyaniline Chemical compound ClC1=C(N)C(=CC=C1)OC=1C=NC2=C(C=CC=C2C=1)F MVXWAQWKJLMULU-UHFFFAOYSA-N 0.000 claims 1
- OWAJMHJQSRVDEX-UHFFFAOYSA-N 2-fluoro-6-(8-fluoroquinolin-3-yl)oxyaniline Chemical compound FC1=C(N)C(=CC=C1)OC=1C=NC2=C(C=CC=C2C=1)F OWAJMHJQSRVDEX-UHFFFAOYSA-N 0.000 claims 1
- PFLIPGRNNMWXEB-UHFFFAOYSA-N 2-trimethylsilylbenzenethiol Chemical compound C[Si](C)(C)C1=CC=CC=C1S PFLIPGRNNMWXEB-UHFFFAOYSA-N 0.000 claims 1
- NMLVUBPGWBQXKR-UHFFFAOYSA-N 3-(2-aminophenyl)sulfanyl-6-chloro-4-phenyl-1h-quinolin-2-one Chemical compound NC1=CC=CC=C1SC(C(NC1=CC=C(Cl)C=C11)=O)=C1C1=CC=CC=C1 NMLVUBPGWBQXKR-UHFFFAOYSA-N 0.000 claims 1
- GWFUJTHUTYCYAG-UHFFFAOYSA-N 3-(2-bromophenyl)sulfanylquinoline Chemical compound BrC1=CC=CC=C1SC1=CN=C(C=CC=C2)C2=C1 GWFUJTHUTYCYAG-UHFFFAOYSA-N 0.000 claims 1
- JCWXGRGSNDYYNB-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfanyl-8-nitroquinoline Chemical compound C=1N=C2C([N+](=O)[O-])=CC=CC2=CC=1SC1=CC=CC=C1Cl JCWXGRGSNDYYNB-UHFFFAOYSA-N 0.000 claims 1
- JACCPCLPOWYWDT-UHFFFAOYSA-N 3-(2-nitrophenoxy)quinoline Chemical compound [N+](=O)([O-])C1=C(OC=2C=NC3=CC=CC=C3C=2)C=CC=C1 JACCPCLPOWYWDT-UHFFFAOYSA-N 0.000 claims 1
- QFMKMWJQRPNDRT-UHFFFAOYSA-N 3-(2-nitrophenyl)sulfanylquinoline Chemical compound [O-][N+](=O)C1=CC=CC=C1SC1=CN=C(C=CC=C2)C2=C1 QFMKMWJQRPNDRT-UHFFFAOYSA-N 0.000 claims 1
- KLYDQTRPHIWIFX-UHFFFAOYSA-N 3-(3-chloro-2-nitrophenoxy)-8-fluoroquinoline Chemical compound ClC=1C(=C(OC=2C=NC3=C(C=CC=C3C=2)F)C=CC=1)[N+](=O)[O-] KLYDQTRPHIWIFX-UHFFFAOYSA-N 0.000 claims 1
- BPJCJWYWNMEUKW-UHFFFAOYSA-N 3-(3-fluorophenyl)sulfanyl-8-iodoquinoline Chemical compound FC1=CC=CC(SC=2C=C3C=CC=C(I)C3=NC=2)=C1 BPJCJWYWNMEUKW-UHFFFAOYSA-N 0.000 claims 1
- ADCYRXFPTFYANZ-UHFFFAOYSA-N 3-(3-fluorophenyl)sulfanyl-8-nitroquinoline Chemical compound C=1N=C2C([N+](=O)[O-])=CC=CC2=CC=1SC1=CC=CC(F)=C1 ADCYRXFPTFYANZ-UHFFFAOYSA-N 0.000 claims 1
- VRQOZPJITDVFQE-UHFFFAOYSA-N 3-(3-fluorophenyl)sulfanylquinolin-8-amine Chemical compound C=1N=C2C(N)=CC=CC2=CC=1SC1=CC=CC(F)=C1 VRQOZPJITDVFQE-UHFFFAOYSA-N 0.000 claims 1
- SKJYXWUMRMEOQR-UHFFFAOYSA-N 3-(3-fluorophenyl)sulfanylquinoline Chemical compound FC1=CC=CC(SC=2C=C3C=CC=CC3=NC=2)=C1 SKJYXWUMRMEOQR-UHFFFAOYSA-N 0.000 claims 1
- OITSIMRATCXNKP-UHFFFAOYSA-N 3-[(2-bromo-4,5-dimethoxyphenyl)methyl]-1H-quinolin-4-one Chemical compound BrC1=C(CC=2C=NC3=CC=CC=C3C=2O)C=C(C(=C1)OC)OC OITSIMRATCXNKP-UHFFFAOYSA-N 0.000 claims 1
- VCVWEKQRHJYLFY-UHFFFAOYSA-N 3-[(2-bromo-4,5-dimethoxyphenyl)methyl]-4-chloroquinoline Chemical compound BrC1=C(CC=2C=NC3=CC=CC=C3C=2Cl)C=C(C(=C1)OC)OC VCVWEKQRHJYLFY-UHFFFAOYSA-N 0.000 claims 1
- PRWQMUZDHUYURQ-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-2-methoxy-6-pyridin-3-ylquinoline Chemical compound ClC1=C(CC=2C(=NC3=CC=C(C=C3C=2)C=2C=NC=CC=2)OC)C=CC=C1 PRWQMUZDHUYURQ-UHFFFAOYSA-N 0.000 claims 1
- GWPHPTBFWGERBZ-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-phenyl-8-(trifluoromethyl)quinoline Chemical compound C=1N=C2C(C(F)(F)F)=CC=CC2=C(C=2C=CC=CC=2)C=1CC1=CC=CC=C1Cl GWPHPTBFWGERBZ-UHFFFAOYSA-N 0.000 claims 1
- YEPQLCNYPFHNFN-UHFFFAOYSA-N 3-chloro-4-(quinolin-3-ylamino)benzonitrile Chemical compound ClC1=CC(C#N)=CC=C1NC1=CN=C(C=CC=C2)C2=C1 YEPQLCNYPFHNFN-UHFFFAOYSA-N 0.000 claims 1
- LJPUAUWQMCBVLX-UHFFFAOYSA-N 4,6-dimethyl-3-(2-nitroanilino)-1H-quinolin-2-one Chemical compound CC1=C(C(NC2=CC=C(C=C12)C)=O)NC1=C(C=CC=C1)[N+](=O)[O-] LJPUAUWQMCBVLX-UHFFFAOYSA-N 0.000 claims 1
- XVILAVFXIBICTQ-UHFFFAOYSA-N 4,6-dimethyl-3-(5-methyl-2,4-dinitroanilino)-1H-quinolin-2-one Chemical compound CC1=C(C(NC2=CC=C(C=C12)C)=O)NC1=C(C=C(C(=C1)C)[N+](=O)[O-])[N+](=O)[O-] XVILAVFXIBICTQ-UHFFFAOYSA-N 0.000 claims 1
- ZHUYCEBQNJVSQY-UHFFFAOYSA-N 4-[3-(2-aminophenoxy)-7-chloroquinolin-4-yl]-5-methoxy-2-methyl-1,2,4-triazol-3-one Chemical compound NC1=C(OC=2C=NC3=CC(=CC=C3C=2N2C(N(N=C2OC)C)=O)Cl)C=CC=C1 ZHUYCEBQNJVSQY-UHFFFAOYSA-N 0.000 claims 1
- BXNZYHZZKRTFLO-UHFFFAOYSA-N 6-bromo-3-[(2-chlorophenyl)methyl]-2-methoxyquinoline Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1CC1=CC=CC=C1Cl BXNZYHZZKRTFLO-UHFFFAOYSA-N 0.000 claims 1
- OLAPMHHJJHDJRF-UHFFFAOYSA-N 8-chloro-3-(3-fluorophenyl)sulfanylquinoline Chemical compound FC1=CC=CC(SC=2C=C3C=CC=C(Cl)C3=NC=2)=C1 OLAPMHHJJHDJRF-UHFFFAOYSA-N 0.000 claims 1
- PXQQHPMMIPHDFS-UHFFFAOYSA-N 8-fluoro-3-(3-fluoro-2-iodophenoxy)quinoline Chemical compound FC1=CC=CC(OC=2C=C3C=CC=C(F)C3=NC=2)=C1I PXQQHPMMIPHDFS-UHFFFAOYSA-N 0.000 claims 1
- NIJLEFMRDVRFEK-UHFFFAOYSA-N 8-fluoro-3-(3-fluoro-2-nitrophenoxy)quinoline Chemical compound FC=1C=CC=C2C=C(C=NC=12)OC1=C(C(=CC=C1)F)[N+](=O)[O-] NIJLEFMRDVRFEK-UHFFFAOYSA-N 0.000 claims 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- WEZPQOJEFGGQPA-UHFFFAOYSA-N ClC=1C(=C(C=CC=1)O)[Si](C)(C)C Chemical compound ClC=1C(=C(C=CC=1)O)[Si](C)(C)C WEZPQOJEFGGQPA-UHFFFAOYSA-N 0.000 claims 1
- FLBDYONSSYWSMN-UHFFFAOYSA-N FC=1C(=C(C=CC=1)O)[Si](C)(C)C Chemical compound FC=1C(=C(C=CC=1)O)[Si](C)(C)C FLBDYONSSYWSMN-UHFFFAOYSA-N 0.000 claims 1
- XMZFONJRWOOCEL-UHFFFAOYSA-N N-(2,4-dinitrophenyl)quinolin-3-amine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1NC1=CN=C(C=CC=C2)C2=C1 XMZFONJRWOOCEL-UHFFFAOYSA-N 0.000 claims 1
- KIQRMIODPVDUQT-UHFFFAOYSA-N N-(2-bromo-4-chlorophenyl)quinolin-3-amine Chemical compound BrC1=C(C=CC(=C1)Cl)NC=1C=NC2=CC=CC=C2C=1 KIQRMIODPVDUQT-UHFFFAOYSA-N 0.000 claims 1
- WQQRCSJXGCAXRL-UHFFFAOYSA-N N-(2-bromo-4-methylphenyl)quinolin-3-amine Chemical compound BrC1=C(C=CC(=C1)C)NC=1C=NC2=CC=CC=C2C=1 WQQRCSJXGCAXRL-UHFFFAOYSA-N 0.000 claims 1
- SUSNKRNVMDAMPH-UHFFFAOYSA-N N-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-(trifluoromethyl)quinoxalin-2-amine Chemical compound ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NC1=NC2=CC=CC=C2N=C1C(F)(F)F SUSNKRNVMDAMPH-UHFFFAOYSA-N 0.000 claims 1
- TUAAGIPTRHVAGD-UHFFFAOYSA-N N-[2,6-dinitro-4-(trifluoromethyl)phenyl]quinolin-3-amine Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1NC1=CN=C(C=CC=C2)C2=C1 TUAAGIPTRHVAGD-UHFFFAOYSA-N 0.000 claims 1
- BRKQBNWLYMJJPT-UHFFFAOYSA-N N-[2-bromo-5-(trifluoromethyl)phenyl]quinolin-3-amine Chemical compound BrC1=C(C=C(C=C1)C(F)(F)F)NC=1C=NC2=CC=CC=C2C=1 BRKQBNWLYMJJPT-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- OTYGBPGHFXUGQC-UHFFFAOYSA-N OC1=C(C=CC=C1)[SiH](C)C Chemical compound OC1=C(C=CC=C1)[SiH](C)C OTYGBPGHFXUGQC-UHFFFAOYSA-N 0.000 claims 1
- HORQFDLRZYIPHC-UHFFFAOYSA-N [2-(bromomethyl)phenyl]-(3-chloropropyl)-dimethylsilane Chemical compound BrCC1=C(C=CC=C1)[Si](C)(C)CCCCl HORQFDLRZYIPHC-UHFFFAOYSA-N 0.000 claims 1
- ABCUDGGIJHVWJC-UHFFFAOYSA-N [2-(bromomethyl)phenyl]-(chloromethyl)-dimethylsilane Chemical compound ClC[Si](C)(C)C1=CC=CC=C1CBr ABCUDGGIJHVWJC-UHFFFAOYSA-N 0.000 claims 1
- HKSUYRJEPJYYDK-UHFFFAOYSA-N [2-(chloromethyl)phenyl]-trimethylsilane Chemical compound C[Si](C)(C)C1=CC=CC=C1CCl HKSUYRJEPJYYDK-UHFFFAOYSA-N 0.000 claims 1
- UIGRLKDHQXUWLQ-UHFFFAOYSA-N [2-(iodomethyl)phenyl]-trimethylsilane Chemical compound ICC1=C(C=CC=C1)[Si](C)(C)C UIGRLKDHQXUWLQ-UHFFFAOYSA-N 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- MENJGVPVZLRGCL-UHFFFAOYSA-N bis[2-(bromomethyl)phenyl]-dimethylsilane Chemical compound BrCC1=C(C=CC=C1)[Si](C)(C)C1=C(C=CC=C1)CBr MENJGVPVZLRGCL-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- QUPJTRAVSONNSI-UHFFFAOYSA-N dimethyl-[2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]phenyl]silane Chemical compound C[SiH](C1=C(C=CC=C1)CB1OC(C(O1)(C)C)(C)C)C QUPJTRAVSONNSI-UHFFFAOYSA-N 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- QBXZBXCIGZKECO-UHFFFAOYSA-N diphenyl-[2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]phenyl]silane Chemical compound C1(=CC=CC=C1)[SiH](C1=C(C=CC=C1)CB1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1 QBXZBXCIGZKECO-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- CFEIBWNKVLZWRC-UHFFFAOYSA-N methyl-phenyl-[2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]phenyl]silane Chemical compound C[SiH](C1=C(C=CC=C1)CB1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1 CFEIBWNKVLZWRC-UHFFFAOYSA-N 0.000 claims 1
- QFSAWOJSDNMBAX-UHFFFAOYSA-N n-(2,4-dichlorophenyl)quinoxalin-2-amine Chemical compound ClC1=CC(Cl)=CC=C1NC1=CN=C(C=CC=C2)C2=N1 QFSAWOJSDNMBAX-UHFFFAOYSA-N 0.000 claims 1
- NBGOVSMYVJIBRJ-UHFFFAOYSA-N n-(2-bromophenyl)quinolin-3-amine Chemical compound BrC1=CC=CC=C1NC1=CN=C(C=CC=C2)C2=C1 NBGOVSMYVJIBRJ-UHFFFAOYSA-N 0.000 claims 1
- JUTPXDWGXWSMDV-UHFFFAOYSA-N n-(2-chlorophenyl)-3-methylquinoxalin-2-amine Chemical compound CC1=NC2=CC=CC=C2N=C1NC1=CC=CC=C1Cl JUTPXDWGXWSMDV-UHFFFAOYSA-N 0.000 claims 1
- QNAZPXBMPYWCKK-UHFFFAOYSA-N n-(2-chlorophenyl)quinolin-3-amine Chemical compound ClC1=CC=CC=C1NC1=CN=C(C=CC=C2)C2=C1 QNAZPXBMPYWCKK-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 230000003032 phytopathogenic effect Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 0 CC1C(N)=*CCCC(C)(*)CCCC1 Chemical compound CC1C(N)=*CCCC(C)(*)CCCC1 0.000 description 3
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| EP15290278.9 | 2015-10-29 | ||
| PCT/EP2016/076048 WO2017072283A1 (en) | 2015-10-29 | 2016-10-28 | Trisubstitutedsilylphenoxyheterocycles and analogues |
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| JP2018535211A5 true JP2018535211A5 (OSRAM) | 2019-11-28 |
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| WO2017178408A1 (en) * | 2016-04-15 | 2017-10-19 | Syngenta Participations Ag | Microbiocidal silicon containing aryl derivatives |
| EP3619197A1 (en) * | 2017-05-03 | 2020-03-11 | Bayer Aktiengesellschaft | Trisubstitutedsilylmethylphenoxyquinolines and analogues |
| TW201927768A (zh) | 2017-12-21 | 2019-07-16 | 德商拜耳廠股份有限公司 | 三取代矽基甲基雜芳氧基喹啉及類似物 |
| TW202028193A (zh) * | 2018-10-20 | 2020-08-01 | 德商拜耳廠股份有限公司 | 氧雜環丁基苯氧基喹啉及類似物 |
| EP4045485A1 (en) | 2019-10-18 | 2022-08-24 | The Regents Of The University Of California | 3-phenylsulphonyl-quinoline derivatives as agents for treating pathogenic blood vessels disorders |
| WO2021257863A1 (en) | 2020-06-19 | 2021-12-23 | Incyte Corporation | Pyrrolotriazine compounds as jak2 v617f inhibitors |
| US11691971B2 (en) | 2020-06-19 | 2023-07-04 | Incyte Corporation | Naphthyridinone compounds as JAK2 V617F inhibitors |
| US11767323B2 (en) | 2020-07-02 | 2023-09-26 | Incyte Corporation | Tricyclic pyridone compounds as JAK2 V617F inhibitors |
| HRP20250814T1 (hr) | 2020-07-02 | 2025-09-12 | Incyte Corporation | Spojevi tricikličke uree kao jak2 v617f inhibitori |
| US11661422B2 (en) | 2020-08-27 | 2023-05-30 | Incyte Corporation | Tricyclic urea compounds as JAK2 V617F inhibitors |
| JP2023554063A (ja) | 2020-12-18 | 2023-12-26 | バイエル・アクチエンゲゼルシヤフト | 作物における耐性植物病原性真菌を防除するためのｄｈｏｄｈ阻害剤の使用 |
| WO2022140231A1 (en) | 2020-12-21 | 2022-06-30 | Incyte Corporation | Deazaguaine compounds as jak2 v617f inhibitors |
| CA3211748A1 (en) | 2021-02-25 | 2022-09-01 | Incyte Corporation | Spirocyclic lactams as jak2 v617f inhibitors |
| AU2022380979A1 (en) | 2021-11-02 | 2024-06-06 | Flare Therapeutics Inc. | Pparg inverse agonists and uses thereof |
| IL315647A (en) | 2022-03-17 | 2024-11-01 | Incyte Corp | Tricyclic urea compounds as Jak2 and 617f inhibitors |
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| DE2102811A1 (de) * | 1971-02-04 | 1972-08-03 | Mironow, Wladimir Florowitsch; Fedotow, Nikolaj Semjonowitsch; Koslikow, Wadim Lwowitsch; Moskau | 1,3-Bis-(hydroxyaryl)-tetraorganodisiloxane und Verfahren zu deren Herstellung |
| DD264219A1 (de) * | 1987-09-04 | 1989-01-25 | Univ Halle Wittenberg | Verfahren zur herstellung von 2-organ-alkoxysilylphenolen, deren ethern und estern |
| DD264216A1 (de) * | 1987-09-04 | 1989-01-25 | Univ Halle Wittenberg | Verfahren zur synthese von bis-(o-hydroxyaryl)-diakyl(aryl)-silanen und deren o-substituierten derivaten |
| DD264218A1 (de) * | 1987-09-04 | 1989-01-25 | Univ Halle Wittenberg | Verfahren zur herstellung von bis(o-hydroxyaryl)-alkyl(aryl)-alkoxysilanen und deren o-substituierten derivaten |
| IL89029A (en) | 1988-01-29 | 1993-01-31 | Lilly Co Eli | Fungicidal quinoline and cinnoline derivatives, compositions containing them, and fungicidal methods of using them |
| AU634561B2 (en) * | 1989-07-27 | 1993-02-25 | Eli Lilly And Company | Naphthyridine derivatives |
| SK44894A3 (en) * | 1991-10-18 | 1995-04-12 | Monsanto Co | Trisubstituted aromatic compounds, method of their preparation and fungicidal agents |
| BR9711816A (pt) * | 1996-08-01 | 1999-08-31 | Du Pont | Composto, composição fungicida, método para controlar doenças de plantas causadas pelos agentes patogênicos f·ngicos de plantas, composição artropodicida e método para controlar artrópodes. |
| BRPI0308696B8 (pt) | 2002-03-27 | 2021-05-25 | Axovant Sciences Gmbh | composto derivado de quinolina, seu processo de preparação, sua composição farmacêutica e seus usos |
| DE102004007076A1 (de) * | 2004-02-13 | 2005-08-25 | Bayer Cropscience Ag | Imidazolopyrimidine |
| EP1928457B1 (en) * | 2005-09-30 | 2012-12-12 | Pulmagen Therapeutics (Asthma) Limited | Quinolines and their therapeutic use |
| JP2009520014A (ja) * | 2005-12-20 | 2009-05-21 | リヒター ゲデオン ニュルト | ｍＧｌｕＲ５受容体介在障害の治療に有用なキノリン誘導体 |
| EP1908472A1 (en) | 2006-10-02 | 2008-04-09 | Bayer Schering Pharma Aktiengesellschaft | Silicon derivatives for PET imaging |
| KR20090128426A (ko) * | 2007-03-23 | 2009-12-15 | 애보트 게엠베하 운트 콤파니 카게 | 세로토닌 ５―ｈｔ６ 수용체의 조절에 반응하는 장애를 치료하는 데 적합한 퀴놀린 화합물 |
| AU2008264999B8 (en) * | 2007-06-18 | 2013-10-31 | Richter Gedeon Nyrt. | Sulfonyl-quinoline derivatives |
| BRPI0812853A2 (pt) * | 2007-08-07 | 2014-12-23 | Abbott Gmbh | Compostos de quinolina adequados para tratar distúrbios que respondem à modulação do receptor 5-ht6 de serotonina. |
| US8288410B2 (en) * | 2008-07-08 | 2012-10-16 | Florida Agricultural And Mechanical University | 3-substituted quinolinium and 7H-indolo[2,3-c]quinolinium salts as new antiinfectives |
| KR101430842B1 (ko) | 2010-01-04 | 2014-08-18 | 닛뽕소다 가부시키가이샤 | 함질소 헤테로 고리 화합물 및 농원예용 살균제 |
| RU2443697C1 (ru) * | 2010-12-21 | 2012-02-27 | Александр Васильевич Иващенко | Замещенные метил-амины, антагонисты серотониновых 5-ht6 рецепторов, способы получения и применения |
| WO2013058825A1 (en) | 2011-04-07 | 2013-04-25 | Cornell University | Silyl monomers capable of multimerizing in an aqueous solution, and methods of using same |
| AR086411A1 (es) | 2011-05-20 | 2013-12-11 | Nippon Soda Co | Compuesto heterociclico conteniendo nitrogeno y fungicida para el uso en agricultura y jardineria |
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| JP5729889B2 (ja) | 2011-10-17 | 2015-06-03 | 日本曹達株式会社 | 含窒素ヘテロ環化合物および農園芸用殺菌剤 |
| RU2500672C1 (ru) * | 2012-10-25 | 2013-12-10 | Андрей Александрович Иващенко | (3-арилсульфонилхинолин-8-ил)-диалкил-амины - селективные антагонисты серотониновых 5-ht6 рецепторов, способы их получения и применения |
| JP2014125441A (ja) * | 2012-12-26 | 2014-07-07 | Nippon Soda Co Ltd | 含窒素ヘテロ環化合物および農園芸用殺菌剤 |
| JP5796848B2 (ja) | 2012-12-27 | 2015-10-21 | 彰夫 宮田 | シャトルコックの壁打ち用ボード |
| JP2014166991A (ja) * | 2013-01-31 | 2014-09-11 | Nippon Soda Co Ltd | 含窒素ヘテロ環化合物および農園芸用殺菌剤 |
-
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- 2016-10-28 KR KR1020187014736A patent/KR20180077205A/ko not_active Abandoned
- 2016-10-28 TW TW105135173A patent/TWI720046B/zh not_active IP Right Cessation
- 2016-10-28 UA UAA201805811A patent/UA125287C2/uk unknown
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- 2016-10-28 EP EP16787887.5A patent/EP3368514B1/en active Active
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- 2016-10-28 AU AU2016347498A patent/AU2016347498B2/en not_active Ceased
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- 2016-10-28 WO PCT/EP2016/076048 patent/WO2017072283A1/en not_active Ceased
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2018
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