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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| JP2023018482A JP7611278B2 (ja) | 2016-12-29 | 2023-02-09 | 金属酵素阻害剤化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| ES2774267T3 (es) * | 2012-01-20 | 2020-07-20 | Mycovia Pharmaceuticals Inc | Compuestos inhibidores de metaloenzimas |
| FI3562487T3 (fi) | 2016-12-29 | 2023-12-14 | Ji Xing Pharmaceuticals Hong Kong Ltd | Metalloentsyymi-inhibiittoriyhdisteitä |
| EP3562306B1 (en) | 2016-12-29 | 2025-02-26 | Ji Xing Pharmaceuticals Hong Kong Limited | Metalloenzyme inhibitor compounds |
| CA3126224A1 (en) * | 2019-01-08 | 2020-07-16 | Corxel Pharmaceuticals Hong Kong Limited | Metalloenzyme inhibitor compounds |
| GB201901757D0 (en) | 2019-02-08 | 2019-03-27 | Syngenta Crop Protection Ag | Herbicidal compounds |
| CN115803317B (zh) | 2020-05-19 | 2025-07-15 | 拜耳作物科学股份公司 | 作为杀真菌化合物的氮杂双环(硫代)酰胺 |
| 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 |
Family Cites Families (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2939916A1 (de) | 1979-10-02 | 1981-04-23 | Hoechst Ag, 6000 Frankfurt | Quaternierte, verbrueckte benzimidazolyl-benzimidazole, verfahren zu deren herstellung und deren verwendung |
| US4921475A (en) | 1983-08-18 | 1990-05-01 | Drug Delivery Systems Inc. | Transdermal drug patch with microtubes |
| US5087240A (en) | 1983-08-18 | 1992-02-11 | Drug Delivery Systems Inc. | Transdermal drug patch with conductive fibers |
| US4738851A (en) | 1985-09-27 | 1988-04-19 | University Of Iowa Research Foundation, Inc. | Controlled release ophthalmic gel formulation |
| US5163899A (en) | 1987-03-20 | 1992-11-17 | Drug Delivery Systems Inc. | Transdermal drug delivery system |
| US5312325A (en) | 1987-05-28 | 1994-05-17 | Drug Delivery Systems Inc | Pulsating transdermal drug delivery system |
| GB8804164D0 (en) | 1988-02-23 | 1988-03-23 | Tucker J M | Bandage for administering physiologically active compound |
| US4882150A (en) | 1988-06-03 | 1989-11-21 | Kaufman Herbert E | Drug delivery system |
| US5008110A (en) | 1988-11-10 | 1991-04-16 | The Procter & Gamble Company | Storage-stable transdermal patch |
| US5088977A (en) | 1988-12-21 | 1992-02-18 | Drug Delivery Systems Inc. | Electrical transdermal drug applicator with counteractor and method of drug delivery |
| US5521222A (en) | 1989-09-28 | 1996-05-28 | Alcon Laboratories, Inc. | Topical ophthalmic pharmaceutical vehicles |
| EP0431519B1 (en) | 1989-12-04 | 1994-06-15 | G.D. Searle & Co. | System for transdermal albuterol administration |
| US5106863A (en) | 1990-03-26 | 1992-04-21 | Ortho Pharmaceutical Corporation | Substituted imidazole and pyridine derivatives |
| US5077033A (en) | 1990-08-07 | 1991-12-31 | Mediventures Inc. | Ophthalmic drug delivery with thermo-irreversible gels of polxoxyalkylene polymer and ionic polysaccharide |
| ATE141502T1 (de) | 1991-01-15 | 1996-09-15 | Alcon Lab Inc | Verwendung von karrageenan in topischen ophthalmologischen zusammensetzungen |
| US5352456A (en) | 1991-10-10 | 1994-10-04 | Cygnus Therapeutic Systems | Device for administering drug transdermally which provides an initial pulse of drug |
| DE69228827T2 (de) | 1991-12-18 | 1999-10-21 | Minnesota Mining And Mfg. Co., Saint Paul | Mehrschichtige sperrstrukturen |
| EP0553769B1 (de) | 1992-01-29 | 1996-01-03 | FRANZ VÖLKL GmbH & CO. SKI UND TENNIS SPORTARTIKELFABRIK KG | Ballspielschläger, insbesondere Tennisschläger |
| IL114193A (en) | 1994-06-20 | 2000-02-29 | Teva Pharma | Ophthalmic pharmaceutical compositions based on sodium alginate |
| ES2094688B1 (es) | 1994-08-08 | 1997-08-01 | Cusi Lab | Manoemulsion del tipo de aceite en agua, util como vehiculo oftalmico y procedimiento para su preparacion. |
| IT1283911B1 (it) | 1996-02-05 | 1998-05-07 | Farmigea Spa | Soluzioni oftalmiche viscosizzate con polisaccaridi della gomma di tamarindo |
| US5800807A (en) | 1997-01-29 | 1998-09-01 | Bausch & Lomb Incorporated | Ophthalmic compositions including glycerin and propylene glycol |
| US6261547B1 (en) | 1998-04-07 | 2001-07-17 | Alcon Manufacturing, Ltd. | Gelling ophthalmic compositions containing xanthan gum |
| US6197934B1 (en) | 1998-05-22 | 2001-03-06 | Collagenesis, Inc. | Compound delivery using rapidly dissolving collagen film |
| AU5886500A (en) | 1999-06-23 | 2001-01-09 | Sepracor, Inc. | Indolyl-benzimidazole antibacterials, and methods of use thereof |
| JP5039268B2 (ja) | 2001-10-26 | 2012-10-03 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | ベンゾイミダゾールおよび類縁体および蛋白キナーゼ阻害剤としてのその使用 |
| AU2003235741B8 (en) * | 2002-01-07 | 2009-01-15 | Eisai R&D Management Co., Ltd. | Deazapurines and uses thereof |
| CA2518318A1 (en) | 2003-03-17 | 2004-09-30 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| EP1604988A1 (en) * | 2004-05-18 | 2005-12-14 | Sanofi-Aventis Deutschland GmbH | Pyridazinone derivatives, methods for producing them and their use as pharmaceuticals |
| PL1861387T3 (pl) | 2005-01-28 | 2014-08-29 | Dae Woong Pharma | Pochodne benzoimidazolu i ich kompozycje farmaceutyczne |
| AR055669A1 (es) * | 2005-10-03 | 2007-08-29 | Astrazeneca Ab | Derivados de 3h - imidazo[4, 5 -b]piridina como inhibidores selectivos de gsk3, metodos e internediarios para su preparacion, composiciones farmaceuticas que los contienen y su uso para la elaboracion de un medicamento para el tratamiento de enfermedades neurodegenerativas y mentales. |
| ES2274712B1 (es) | 2005-10-06 | 2008-03-01 | Laboratorios Almirall S.A. | Nuevos derivados imidazopiridina. |
| EP1960382A1 (en) | 2005-11-03 | 2008-08-27 | ChemBridge Research Laboratories, Inc. | Heterocyclic compounds as tyrosine kinase modulators |
| US20080027044A1 (en) | 2006-06-13 | 2008-01-31 | Kim Lewis | Prodrug antibiotic screens |
| EP1878724A1 (en) | 2006-07-15 | 2008-01-16 | sanofi-aventis | A regioselective palladium catalyzed synthesis of benzimidazoles and azabenzimidazoles |
| MX2009011208A (es) | 2007-04-19 | 2009-10-30 | Novartis Ag | Derivados de acido nicotinico como moduladores del receptor de glutamato metabotropico-5. |
| US7737175B2 (en) | 2007-06-01 | 2010-06-15 | Duke University | Methods and compositions for regulating HDAC4 activity |
| WO2009000413A1 (en) | 2007-06-26 | 2008-12-31 | Sanofi-Aventis | A regioselective copper catalyzed synthesis of benzimidazoles and azabenzimidazoles |
| JP5142836B2 (ja) | 2007-07-02 | 2013-02-13 | オセ−テクノロジーズ ビーブイ | 走査画像要素位置合わせ方法 |
| US20100216796A1 (en) | 2007-10-04 | 2010-08-26 | Solomon Kattar | N-hydroxy-naphthalene dicarboxamide and n-hydroxy-biphenyl-dicarboxamide compounds as histone deacetylase inhibitors |
| EP2732819B1 (en) | 2008-02-07 | 2019-10-16 | Massachusetts Eye & Ear Infirmary | Compounds that enhance Atoh-1 expression |
| AR072297A1 (es) | 2008-06-27 | 2010-08-18 | Novartis Ag | Derivados de indol-2-il-piridin-3-ilo, composicion farmaceutica que los comprende y su uso en medicamentos para el tratamiento de enfermedades mediadas por la sintasa aldosterona. |
| GB0821994D0 (en) | 2008-12-02 | 2009-01-07 | Ge Healthcare Ltd | In viva imaging method |
| HRP20140371T1 (hr) | 2009-05-15 | 2014-05-23 | Novartis Ag | Arilpiridini kao inhibitori sinteze aldosterona |
| US8519134B2 (en) | 2009-11-17 | 2013-08-27 | Novartis Ag | Aryl-pyridine derivatives as aldosterone synthase inhibitors |
| AU2011242562B2 (en) * | 2010-04-24 | 2016-10-13 | Mycovia Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| US9382226B2 (en) * | 2010-07-21 | 2016-07-05 | Merck Sharp & Dohme Corp. | Aldosterone synthase inhibitors |
| US20130227717A1 (en) | 2010-10-08 | 2013-08-29 | Life Sciences Research Partners Vzw | Hdac inhibitors to treat charcot-marie-tooth disease |
| EP3483147A1 (en) * | 2010-11-13 | 2019-05-15 | Innocrin Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| US8815854B2 (en) * | 2011-06-24 | 2014-08-26 | Arqule, Inc. | Substituted imidazopyridinyl compounds |
| WO2013033901A1 (en) | 2011-09-08 | 2013-03-14 | Merck Sharp & Dohme Corp. | Heterocyclic-substituted benzofuran derivatives and methods of use thereof for the treatment of viral diseases |
| WO2013134472A1 (en) * | 2012-03-08 | 2013-09-12 | Medtronic Ardian Luxembourg S.A.R.L. | Renal neuromodulation methods and systems for treatment of hyperaldosteronism |
| CN103626783B (zh) * | 2012-08-22 | 2016-06-08 | 中国科学院上海药物研究所 | 双环稠杂环化合物及其用途和药物组合物 |
| US10022357B2 (en) | 2013-04-29 | 2018-07-17 | The General Hospital Corporation | Amyloid precursor protein MRNA blockers for treating Down syndrome and Alzheimer's disease |
| MY176401A (en) * | 2014-04-24 | 2020-08-05 | Mitsubishi Tanabe Pharma Corp | Novel disubstituted 1,2,4-triazine compound |
| WO2015188369A1 (en) | 2014-06-13 | 2015-12-17 | Merck Sharp & Dohme Corp. | Purine inhibitors of human phosphatidylinositol 3-kinase delta |
| AP2017009829A0 (en) * | 2014-10-15 | 2017-03-31 | Boehringer Ingelheim Int | Aldosterone synthase inhibitors |
| ES2959782T3 (es) | 2016-12-20 | 2024-02-28 | Fmc Corp | Oxadiazoles fungicidas |
| EP3562306B1 (en) | 2016-12-29 | 2025-02-26 | Ji Xing Pharmaceuticals Hong Kong Limited | Metalloenzyme inhibitor compounds |
| FI3562487T3 (fi) | 2016-12-29 | 2023-12-14 | Ji Xing Pharmaceuticals Hong Kong Ltd | Metalloentsyymi-inhibiittoriyhdisteitä |
| CA3126224A1 (en) | 2019-01-08 | 2020-07-16 | Corxel Pharmaceuticals Hong Kong Limited | Metalloenzyme inhibitor compounds |
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