JP2020510693A5 - - Google Patents
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- Publication number
- JP2020510693A5 JP2020510693A5 JP2019556790A JP2019556790A JP2020510693A5 JP 2020510693 A5 JP2020510693 A5 JP 2020510693A5 JP 2019556790 A JP2019556790 A JP 2019556790A JP 2019556790 A JP2019556790 A JP 2019556790A JP 2020510693 A5 JP2020510693 A5 JP 2020510693A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopropyl
- benzo
- imidazole
- pyridazine
- difluoro
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000001188 haloalkyl group Chemical group 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- -1 Ethyl ((5- (1-cyclopropyl-6-fluoro-1H-benzo [d] imidazol-2-yl) pyridazine-3-yl) methyl) carbamate Chemical compound 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- XYDVZNOPAHRLMH-UHFFFAOYSA-N 2-(6-chloropyridazin-4-yl)-3-ethylbenzimidazole-5-carbonitrile Chemical compound ClC1=CC(=CN=N1)C1=NC2=C(N1CC)C=C(C=C2)C#N XYDVZNOPAHRLMH-UHFFFAOYSA-N 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 4
- 230000001548 androgenic effect Effects 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims 3
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 2
- XHOONWVPIBKMAE-UHFFFAOYSA-N 1-[5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)pyridazin-3-yl]-N,N-dimethylpyrrolidin-3-amine Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C=1C=C(N=NC=1)N1CC(CC1)N(C)C XHOONWVPIBKMAE-UHFFFAOYSA-N 0.000 claims 2
- XJTZAUWHKDDDMU-UHFFFAOYSA-N 1-[5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)pyridazin-3-yl]ethanone Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C=1C=C(N=NC=1)C(C)=O XJTZAUWHKDDDMU-UHFFFAOYSA-N 0.000 claims 2
- QIPCBUDMPMEIJS-UHFFFAOYSA-N 1-[5-(1-cyclopropyl-6-fluorobenzimidazol-2-yl)pyridazin-3-yl]-2,2,2-trifluoroethanol Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C=1C=C(N=NC=1)C(C(F)(F)F)O QIPCBUDMPMEIJS-UHFFFAOYSA-N 0.000 claims 2
- YZBJLUQBBFVWPZ-UHFFFAOYSA-N 1-cyclopropyl-2-(6-cyclopropylpyridazin-4-yl)-5,6-difluorobenzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)C1CC1 YZBJLUQBBFVWPZ-UHFFFAOYSA-N 0.000 claims 2
- OYEKUTLPHBAHIO-UHFFFAOYSA-N 1-cyclopropyl-2-(6-ethenylpyridazin-4-yl)-6-fluorobenzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C1=CN=NC(=C1)C=C OYEKUTLPHBAHIO-UHFFFAOYSA-N 0.000 claims 2
- XXFASMAEDIEFPZ-UHFFFAOYSA-N 1-cyclopropyl-2-(6-ethylpyridazin-4-yl)-5,6-difluorobenzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)CC XXFASMAEDIEFPZ-UHFFFAOYSA-N 0.000 claims 2
- GJHNJNULLGQEDQ-UHFFFAOYSA-N 1-cyclopropyl-2-(6-ethylpyridazin-4-yl)-6-fluorobenzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C1=CN=NC(=C1)CC GJHNJNULLGQEDQ-UHFFFAOYSA-N 0.000 claims 2
- AGCIPACTARPDKK-UHFFFAOYSA-N 1-cyclopropyl-2-(6-ethylsulfinylpyridazin-4-yl)-5,6-difluorobenzimidazole Chemical compound CCS(=O)C1=CC(=CN=N1)C1=NC2=CC(F)=C(F)C=C2N1C1CC1 AGCIPACTARPDKK-UHFFFAOYSA-N 0.000 claims 2
- NFVJNTYFYSJYMW-UHFFFAOYSA-N 1-cyclopropyl-2-(6-ethylsulfonylpyridazin-4-yl)-5,6-difluorobenzimidazole Chemical compound CCS(=O)(=O)C1=CC(=CN=N1)C1=NC2=CC(F)=C(F)C=C2N1C1CC1 NFVJNTYFYSJYMW-UHFFFAOYSA-N 0.000 claims 2
- VHQGEXYNHFIELM-UHFFFAOYSA-N 1-cyclopropyl-2-(6-methylpyridazin-4-yl)-6-(trifluoromethyl)benzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)C(F)(F)F)C1=CN=NC(=C1)C VHQGEXYNHFIELM-UHFFFAOYSA-N 0.000 claims 2
- XSFPFOUMWPBAGO-UHFFFAOYSA-N 1-cyclopropyl-2-[6-(1,1-difluoroethyl)pyridazin-4-yl]-5,6-difluorobenzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)C(C)(F)F XSFPFOUMWPBAGO-UHFFFAOYSA-N 0.000 claims 2
- RXZBRQIHPZGDDS-UHFFFAOYSA-N 1-cyclopropyl-2-[6-(2,2-difluoropropoxy)pyridazin-4-yl]-5,6-difluorobenzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)OCC(C)(F)F RXZBRQIHPZGDDS-UHFFFAOYSA-N 0.000 claims 2
- WNMBNIDIFORJLI-UHFFFAOYSA-N 1-cyclopropyl-2-[6-(2,4-difluorophenyl)pyridazin-4-yl]-5,6-difluorobenzimidazole Chemical compound FC1=CC(F)=C(C=C1)C1=CC(=CN=N1)C1=NC2=CC(F)=C(F)C=C2N1C1CC1 WNMBNIDIFORJLI-UHFFFAOYSA-N 0.000 claims 2
- DBDNVGCBGHUTAB-UHFFFAOYSA-N 1-cyclopropyl-2-[6-(3,3-difluoropyrrolidin-1-yl)pyridazin-4-yl]-5,6-difluorobenzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)N1CC(CC1)(F)F DBDNVGCBGHUTAB-UHFFFAOYSA-N 0.000 claims 2
- HPXSYLMTMIKFJW-UHFFFAOYSA-N 1-cyclopropyl-2-[6-(3,4-difluorophenyl)pyridazin-4-yl]-5,6-difluorobenzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)C1=CC(=C(C=C1)F)F HPXSYLMTMIKFJW-UHFFFAOYSA-N 0.000 claims 2
- WVHAPHHVXUBMBX-UHFFFAOYSA-N 1-cyclopropyl-2-[6-(4,4-difluoropiperidin-1-yl)pyridazin-4-yl]-5,6-difluorobenzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)N1CCC(CC1)(F)F WVHAPHHVXUBMBX-UHFFFAOYSA-N 0.000 claims 2
- CHUIXOIVXUJWJC-UHFFFAOYSA-N 1-cyclopropyl-2-[6-(difluoromethyl)pyridazin-4-yl]-5,6-difluorobenzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)C(F)F CHUIXOIVXUJWJC-UHFFFAOYSA-N 0.000 claims 2
- WARWXVPSCNZSCA-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-(6-methoxypyridazin-4-yl)benzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)OC WARWXVPSCNZSCA-UHFFFAOYSA-N 0.000 claims 2
- KRBSADFXSHRPCM-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-(6-methylpyridazin-4-yl)benzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)C KRBSADFXSHRPCM-UHFFFAOYSA-N 0.000 claims 2
- PJVQVSVSULZKOT-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-(6-methylsulfinylpyridazin-4-yl)benzimidazole Chemical compound CS(=O)C1=CC(=CN=N1)C1=NC2=CC(F)=C(F)C=C2N1C1CC1 PJVQVSVSULZKOT-UHFFFAOYSA-N 0.000 claims 2
- JRLHIPSHJXEXNA-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-(6-methylsulfonylpyridazin-4-yl)benzimidazole Chemical compound CS(=O)(=O)C1=CC(=CN=N1)C1=NC2=CC(F)=C(F)C=C2N1C1CC1 JRLHIPSHJXEXNA-UHFFFAOYSA-N 0.000 claims 2
- FDHFGHXXCABXHM-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-(6-propan-2-yloxypyridazin-4-yl)benzimidazole Chemical compound CC(C)OC1=CC(=CN=N1)C1=NC2=CC(F)=C(F)C=C2N1C1CC1 FDHFGHXXCABXHM-UHFFFAOYSA-N 0.000 claims 2
- YXTUXCUYLWZFAI-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-(6-propan-2-ylpyridazin-4-yl)benzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)C(C)C YXTUXCUYLWZFAI-UHFFFAOYSA-N 0.000 claims 2
- SNCFHTZRURVPQI-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-[6-(1,1,1-trifluoropropan-2-yloxy)pyridazin-4-yl]benzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)OC(C(F)(F)F)C SNCFHTZRURVPQI-UHFFFAOYSA-N 0.000 claims 2
- LMXVXMWICJNSQD-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-[6-(2,2,2-trifluoroethoxy)pyridazin-4-yl]benzimidazole Chemical compound FC1=C(F)C=C2N(C3CC3)C(=NC2=C1)C1=CN=NC(OCC(F)(F)F)=C1 LMXVXMWICJNSQD-UHFFFAOYSA-N 0.000 claims 2
- IKROKYABLVQNRZ-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-[6-(2,2,2-trifluoroethyl)pyridazin-4-yl]benzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)CC(F)(F)F IKROKYABLVQNRZ-UHFFFAOYSA-N 0.000 claims 2
- ZHTWLIXEZQDKPY-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-[6-(4-fluoro-2-methylphenyl)pyridazin-4-yl]benzimidazole Chemical compound CC1=C(C=CC(F)=C1)C1=CC(=CN=N1)C1=NC2=CC(F)=C(F)C=C2N1C1CC1 ZHTWLIXEZQDKPY-UHFFFAOYSA-N 0.000 claims 2
- SCCAXYXTKCJFNP-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-[6-(4-fluorophenyl)pyridazin-4-yl]benzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)C1=CC=C(C=C1)F SCCAXYXTKCJFNP-UHFFFAOYSA-N 0.000 claims 2
- BLFBGYFREGPXPN-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-[6-(4-methylpiperazin-1-yl)pyridazin-4-yl]benzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)N1CCN(CC1)C BLFBGYFREGPXPN-UHFFFAOYSA-N 0.000 claims 2
- UQMACLYGQIKZPJ-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-[6-(4-methylsulfonylpiperazin-1-yl)pyridazin-4-yl]benzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)N1CCN(CC1)S(=O)(=O)C UQMACLYGQIKZPJ-UHFFFAOYSA-N 0.000 claims 2
- HSDDPSVXNJLJAL-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-[6-(trifluoromethyl)pyridazin-4-yl]benzimidazole Chemical compound FC1=C(F)C=C2N(C3CC3)C(=NC2=C1)C1=CN=NC(=C1)C(F)(F)F HSDDPSVXNJLJAL-UHFFFAOYSA-N 0.000 claims 2
- IYHHWWFEFYIVTJ-UHFFFAOYSA-N 1-cyclopropyl-5,6-difluoro-2-[6-[2-(4-fluorophenyl)ethynyl]pyridazin-4-yl]benzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C1=CN=NC(=C1)C#CC1=CC=C(C=C1)F IYHHWWFEFYIVTJ-UHFFFAOYSA-N 0.000 claims 2
- UNKDZYGYYFLKKT-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-2-(6-methylpyridazin-4-yl)benzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C1=CN=NC(=C1)C UNKDZYGYYFLKKT-UHFFFAOYSA-N 0.000 claims 2
- HUECOWBPJAWTBE-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-2-(6-methylpyridazin-4-yl)indole Chemical compound CC1=CC(=CN=N1)C1=CC2=CC=C(F)C=C2N1C1CC1 HUECOWBPJAWTBE-UHFFFAOYSA-N 0.000 claims 2
- SCQRDZCEPKVYMH-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-2-[6-[4-(4-fluorophenyl)piperazin-1-yl]pyridazin-4-yl]benzimidazole Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C1=CN=NC(=C1)N1CCN(CC1)C1=CC=C(C=C1)F SCQRDZCEPKVYMH-UHFFFAOYSA-N 0.000 claims 2
- VRWLZAHGLNGMEH-UHFFFAOYSA-N 1-ethyl-6-fluoro-2-(6-methylpyridazin-4-yl)indole Chemical compound CCN1C2=CC(F)=CC=C2C=C1C1=CN=NC(C)=C1 VRWLZAHGLNGMEH-UHFFFAOYSA-N 0.000 claims 2
- PZRKKGZFHOSNNN-UHFFFAOYSA-N 2-(6-chloropyridazin-4-yl)-1-cyclopropyl-5,6-difluorobenzimidazole Chemical compound ClC1=CC(=CN=N1)C1=NC2=C(N1C1CC1)C=C(C(=C2)F)F PZRKKGZFHOSNNN-UHFFFAOYSA-N 0.000 claims 2
- DLZGTGSKPUFUGW-UHFFFAOYSA-N 2-(6-chloropyridazin-4-yl)-1-cyclopropyl-6-fluorobenzimidazole Chemical compound ClC1=CC(=CN=N1)C1=NC2=C(N1C1CC1)C=C(C=C2)F DLZGTGSKPUFUGW-UHFFFAOYSA-N 0.000 claims 2
- UJHNFDLYWJVYEQ-UHFFFAOYSA-N 2-(6-chloropyridazin-4-yl)-1-ethyl-5,6-difluorobenzimidazole Chemical compound ClC1=CC(=CN=N1)C1=NC2=C(N1CC)C=C(C(=C2)F)F UJHNFDLYWJVYEQ-UHFFFAOYSA-N 0.000 claims 2
- VNSOAEJYLNIPPA-UHFFFAOYSA-N 2-(6-chloropyridazin-4-yl)-3-cyclopropylbenzimidazole-5-carbonitrile Chemical compound ClC1=CC(=CN=N1)C1=NC2=C(N1C1CC1)C=C(C=C2)C#N VNSOAEJYLNIPPA-UHFFFAOYSA-N 0.000 claims 2
- NIOFGFBIWNISCL-UHFFFAOYSA-N 2-(6-cyclobutyloxypyridazin-4-yl)-1-cyclopropyl-5,6-difluorobenzimidazole Chemical compound C1(CCC1)OC1=CC(=CN=N1)C1=NC2=C(N1C1CC1)C=C(C(=C2)F)F NIOFGFBIWNISCL-UHFFFAOYSA-N 0.000 claims 2
- KXJACZUFJAOFGN-UHFFFAOYSA-N 2-(6-cyclopropylpyridazin-4-yl)-1-ethyl-5,6-difluorobenzimidazole Chemical compound C1(CC1)C1=CC(=CN=N1)C1=NC2=C(N1CC)C=C(C(=C2)F)F KXJACZUFJAOFGN-UHFFFAOYSA-N 0.000 claims 2
- ONSJCCXFXPNDGK-UHFFFAOYSA-N 2-[4-[5-(1-cyclopropyl-6-fluorobenzimidazol-2-yl)pyridazin-3-yl]piperazin-1-yl]-N-propan-2-ylacetamide Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C=1C=C(N=NC=1)N1CCN(CC1)CC(=O)NC(C)C ONSJCCXFXPNDGK-UHFFFAOYSA-N 0.000 claims 2
- PCXWENMSPWZPKU-UHFFFAOYSA-N 2-[5-(1-cyclopropyl-6-fluorobenzimidazol-2-yl)pyridazin-3-yl]propan-2-ol Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C=1C=C(N=NC=1)C(C)(C)O PCXWENMSPWZPKU-UHFFFAOYSA-N 0.000 claims 2
- QVKLVEJQVPYOBJ-UHFFFAOYSA-N 2-[6-(difluoromethyl)pyridazin-4-yl]-1-ethyl-5,6-difluorobenzimidazole Chemical compound FC(C1=CC(=CN=N1)C1=NC2=C(N1CC)C=C(C(=C2)F)F)F QVKLVEJQVPYOBJ-UHFFFAOYSA-N 0.000 claims 2
- ASWSQAKOCTZARH-UHFFFAOYSA-N 2-[6-(difluoromethyl)pyridazin-4-yl]-3-ethylbenzimidazole-5-carbonitrile Chemical compound FC(C1=CC(=CN=N1)C1=NC2=C(N1CC)C=C(C=C2)C#N)F ASWSQAKOCTZARH-UHFFFAOYSA-N 0.000 claims 2
- VDFFIEIERJJINI-UHFFFAOYSA-N 2-[[5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)pyridazin-3-yl]methyl]-1,2-thiazolidine 1,1-dioxide Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C=1C=C(N=NC=1)CN1S(CCC1)(=O)=O VDFFIEIERJJINI-UHFFFAOYSA-N 0.000 claims 2
- YGPUGLYBVBOCPZ-UHFFFAOYSA-N 3-cyclopropyl-2-(6-cyclopropylpyridazin-4-yl)benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2N=C(N(C3CC3)C2=C1)C1=CN=NC(=C1)C1CC1 YGPUGLYBVBOCPZ-UHFFFAOYSA-N 0.000 claims 2
- NFOFZNLSXNBEHU-UHFFFAOYSA-N 3-cyclopropyl-2-(6-methoxypyridazin-4-yl)benzimidazole-5-carbonitrile Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)C#N)C1=CN=NC(=C1)OC NFOFZNLSXNBEHU-UHFFFAOYSA-N 0.000 claims 2
- KXLPZBAXZVZVKP-UHFFFAOYSA-N 3-cyclopropyl-2-(6-methylpyridazin-4-yl)benzimidazole-5-carbonitrile Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)C#N)C1=CN=NC(=C1)C KXLPZBAXZVZVKP-UHFFFAOYSA-N 0.000 claims 2
- CJPISUZRANRRSE-UHFFFAOYSA-N 3-cyclopropyl-2-[6-(difluoromethyl)pyridazin-4-yl]benzimidazole-5-carbonitrile Chemical compound FC(F)C1=CC(=CN=N1)C1=NC2=CC=C(C=C2N1C1CC1)C#N CJPISUZRANRRSE-UHFFFAOYSA-N 0.000 claims 2
- XYCAIPSOSDRADN-UHFFFAOYSA-N 3-cyclopropyl-2-[6-(trifluoromethyl)pyridazin-4-yl]benzimidazole-5-carbonitrile Chemical compound FC(F)(F)C1=CC(=CN=N1)C1=NC2=CC=C(C=C2N1C1CC1)C#N XYCAIPSOSDRADN-UHFFFAOYSA-N 0.000 claims 2
- XKJOBXSCVJZABY-UHFFFAOYSA-N 3-ethyl-2-(6-ethylpyridazin-4-yl)benzimidazole-5-carbonitrile Chemical compound C(C)N1C(=NC2=C1C=C(C=C2)C#N)C1=CN=NC(=C1)CC XKJOBXSCVJZABY-UHFFFAOYSA-N 0.000 claims 2
- RGXCKRNXXISTFN-UHFFFAOYSA-N 3-ethyl-2-(6-methoxypyridazin-4-yl)benzimidazole-5-carbonitrile Chemical compound CCN1C2=CC(=CC=C2N=C1C1=CN=NC(OC)=C1)C#N RGXCKRNXXISTFN-UHFFFAOYSA-N 0.000 claims 2
- BXLUDHOXTONJTD-UHFFFAOYSA-N 4-(1-cyclopropyl-6-fluorobenzimidazol-2-yl)cinnoline Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C1=CN=NC2=CC=CC=C12 BXLUDHOXTONJTD-UHFFFAOYSA-N 0.000 claims 2
- JKVOTGXJKVNUFQ-UHFFFAOYSA-N 4-[5-(1-cyclopropyl-6-fluorobenzimidazol-2-yl)pyridazin-3-yl]morpholine Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C=1C=C(N=NC=1)N1CCOCC1 JKVOTGXJKVNUFQ-UHFFFAOYSA-N 0.000 claims 2
- QDKSHVCQSOIGBW-UHFFFAOYSA-N 5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)-N,N-dimethylpyridazin-3-amine Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C=1C=C(N=NC=1)N(C)C QDKSHVCQSOIGBW-UHFFFAOYSA-N 0.000 claims 2
- ALHYMIQYVWZAGO-UHFFFAOYSA-N 5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)-N-(2,2,2-trifluoroethyl)pyridazin-3-amine Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C=1C=C(N=NC=1)NCC(F)(F)F ALHYMIQYVWZAGO-UHFFFAOYSA-N 0.000 claims 2
- FLZONJWFMUVWHR-UHFFFAOYSA-N 5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)-N-(2-methoxyethyl)pyridazin-3-amine Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C=1C=C(N=NC=1)NCCOC FLZONJWFMUVWHR-UHFFFAOYSA-N 0.000 claims 2
- WKRPTXNPXXPRGY-UHFFFAOYSA-N 5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)-N-methylpyridazin-3-amine Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C=1C=C(N=NC=1)NC WKRPTXNPXXPRGY-UHFFFAOYSA-N 0.000 claims 2
- AHAJBVXKUBAKEF-UHFFFAOYSA-N 5-(1-cyclopropyl-6-fluorobenzimidazol-2-yl)-N-(oxan-4-yl)pyridazin-3-amine Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C=1C=C(N=NC=1)NC1CCOCC1 AHAJBVXKUBAKEF-UHFFFAOYSA-N 0.000 claims 2
- XINVDLGFUCRWDZ-UHFFFAOYSA-N 5-(1-cyclopropyl-6-fluorobenzimidazol-2-yl)pyridazine-3-carbonitrile Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C=1C=C(N=NC=1)C#N XINVDLGFUCRWDZ-UHFFFAOYSA-N 0.000 claims 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
- ALCSVNKNTSIYLR-UHFFFAOYSA-N N-[5-(1-cyclopropyl-6-fluorobenzimidazol-2-yl)pyridazin-3-yl]ethanesulfonamide Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C=1C=C(N=NC=1)NS(=O)(=O)CC ALCSVNKNTSIYLR-UHFFFAOYSA-N 0.000 claims 2
- KPOAZYZPLGBYFV-UHFFFAOYSA-N N-[[5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)pyridazin-3-yl]methyl]-N-methylmethanesulfonamide Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C=1C=C(N=NC=1)CN(S(=O)(=O)C)C KPOAZYZPLGBYFV-UHFFFAOYSA-N 0.000 claims 2
- UHIMFZHXEGVADD-UHFFFAOYSA-N N-[[5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)pyridazin-3-yl]methyl]ethanesulfonamide Chemical compound C(C)S(=O)(=O)NCC=1N=NC=C(C=1)C1=NC2=C(N1C1CC1)C=C(C(=C2)F)F UHIMFZHXEGVADD-UHFFFAOYSA-N 0.000 claims 2
- YCNWAFIGHHAIBF-UHFFFAOYSA-N N-[[5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)pyridazin-3-yl]methyl]methanesulfonamide Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C=1C=C(N=NC=1)CNS(=O)(=O)C YCNWAFIGHHAIBF-UHFFFAOYSA-N 0.000 claims 2
- IVGORWRSDGOSRI-UHFFFAOYSA-N N-[[5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)pyridazin-3-yl]methyl]propane-2-sulfonamide Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C=1C=C(N=NC=1)CNS(=O)(=O)C(C)C IVGORWRSDGOSRI-UHFFFAOYSA-N 0.000 claims 2
- NKVLQXHGVWWWBE-UHFFFAOYSA-N N-[[5-(1-cyclopropyl-6-fluorobenzimidazol-2-yl)pyridazin-3-yl]methyl]ethanesulfonamide Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C=1C=C(N=NC=1)CNS(=O)(=O)CC NKVLQXHGVWWWBE-UHFFFAOYSA-N 0.000 claims 2
- XAAGUYQEFBDWFU-UHFFFAOYSA-N N-[[5-(1-cyclopropyl-6-fluorobenzimidazol-2-yl)pyridazin-3-yl]methyl]propanamide Chemical compound C1(CC1)N1C(=NC2=C1C=C(C=C2)F)C=1C=C(N=NC=1)CNC(CC)=O XAAGUYQEFBDWFU-UHFFFAOYSA-N 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- DZFONXTWNMTATH-UHFFFAOYSA-N 1-[4-[5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)pyridazin-3-yl]piperazin-1-yl]ethanone Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C=1C=C(N=NC=1)N1CCN(CC1)C(C)=O DZFONXTWNMTATH-UHFFFAOYSA-N 0.000 claims 1
- VXIPNYKBIIGFBZ-UHFFFAOYSA-N 1-[5-(1-cyclopropyl-5,6-difluorobenzimidazol-2-yl)pyridazin-3-yl]-2,2,2-trifluoroethanol Chemical compound C1(CC1)N1C(=NC2=C1C=C(C(=C2)F)F)C=1C=C(N=NC=1)C(C(F)(F)F)O VXIPNYKBIIGFBZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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| JP6189865B2 (ja) | 2012-01-20 | 2017-08-30 | ヴィアメット ファーマスーティカルズ，インコーポレイテッド | 金属酵素阻害薬化合物 |
| EP3562306B1 (en) | 2016-12-29 | 2025-02-26 | Ji Xing Pharmaceuticals Hong Kong Limited | Metalloenzyme inhibitor compounds |
| EP3562487B1 (en) | 2016-12-29 | 2023-11-29 | Ji Xing Pharmaceuticals Hong Kong Limited | Metalloenzyme inhibitor compounds |
| US12358893B2 (en) | 2019-01-08 | 2025-07-15 | Corxel Pharmaceuticals Hong Kong Limited | Metalloenzyme inhibitor compounds |
| GB201901757D0 (en) | 2019-02-08 | 2019-03-27 | Syngenta Crop Protection Ag | Herbicidal compounds |
| US20230192617A1 (en) | 2020-05-19 | 2023-06-22 | Bayer Cropscience Aktiengesellschaft | Azabicyclic(thio)amides as fungicidal compounds |
| WO2021249995A1 (en) | 2020-06-10 | 2021-12-16 | Bayer Aktiengesellschaft | Azabicyclyl-substituted heterocycles as fungicides |
| AT524288B1 (de) * | 2020-09-16 | 2024-05-15 | Gatan Inc | Computergestütztes Verfahren zur Bestimmung eines Elementanteiles eines Bestimmungselementes kleiner Ordnungszahl, insbesondere eines Li-Anteiles, und Vorrichtung zur Datenverarbeitung hierzu |
| WO2025157275A1 (zh) * | 2024-01-26 | 2025-07-31 | 箕星药业香港有限公司 | 金属酶抑制剂化合物的固体形式 |
| CN120463643B (zh) * | 2025-05-27 | 2025-11-28 | 咸阳职业技术学院 | 一种2-环丙基胺基-3-硝基-6-氯吡啶的合成方法 |
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-
2017
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- 2017-12-22 KR KR1020197022285A patent/KR102690885B1/ko active Active
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