JP2015515976A5 - - Google Patents
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- Publication number
- JP2015515976A5 JP2015515976A5 JP2015509561A JP2015509561A JP2015515976A5 JP 2015515976 A5 JP2015515976 A5 JP 2015515976A5 JP 2015509561 A JP2015509561 A JP 2015509561A JP 2015509561 A JP2015509561 A JP 2015509561A JP 2015515976 A5 JP2015515976 A5 JP 2015515976A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- benzo
- indol
- carbonitrile
- imidazole
- 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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- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 206010061218 Inflammation Diseases 0.000 claims description 9
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
- 230000004054 inflammatory process Effects 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
- YWBCSLQTTRDWOU-UHFFFAOYSA-N 2-[1-(5-ethyl-7-methyl-1h-indol-4-yl)-1-methoxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(OC)C3=C4C=CNC4=C(C)C=C3CC)=NC2=C1 YWBCSLQTTRDWOU-UHFFFAOYSA-N 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- YGPVRHHGKCQSIL-UHFFFAOYSA-N 5-methoxy-7-methyl-1h-indole Chemical compound COC1=CC(C)=C2NC=CC2=C1 YGPVRHHGKCQSIL-UHFFFAOYSA-N 0.000 claims description 7
- 230000024203 complement activation Effects 0.000 claims description 7
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 206010035664 Pneumonia Diseases 0.000 claims description 6
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
- 208000026935 allergic disease Diseases 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 208000002780 macular degeneration Diseases 0.000 claims description 6
- 230000010410 reperfusion Effects 0.000 claims description 6
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 206010046851 Uveitis Diseases 0.000 claims description 5
- 230000000295 complement effect Effects 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 230000037361 pathway Effects 0.000 claims description 5
- WWWSPJKOYQAYLB-UHFFFAOYSA-N 2-(5-hydroxy-6,8-dimethyl-3,4-dihydro-1h-benzo[cd]indol-5-yl)-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C3(CCC4=CNC5=C(C)C=C(C3=C54)C)O)=NC2=C1 WWWSPJKOYQAYLB-UHFFFAOYSA-N 0.000 claims description 4
- OYCNXXLEZSVDMI-UHFFFAOYSA-N 2-(6-ethyl-5-hydroxy-8-methyl-3,4-dihydro-1h-benzo[cd]indol-5-yl)-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C3(CCC4=CNC5=C(C)C=C(C3=C54)CC)O)=NC2=C1 OYCNXXLEZSVDMI-UHFFFAOYSA-N 0.000 claims description 4
- VFNCCHPOOUQFTB-UHFFFAOYSA-N 2-[(3-chloro-5-methoxy-7-methyl-1h-indol-4-yl)-hydroxymethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(O)C3=C4C(Cl)=CNC4=C(C)C=C3OC)=NC2=C1 VFNCCHPOOUQFTB-UHFFFAOYSA-N 0.000 claims description 4
- ILRCDGRTLHACEO-UHFFFAOYSA-N 2-[(5,7-dimethyl-1h-indol-4-yl)-hydroxymethyl]-3h-benzimidazole-5-carbonitrile Chemical compound C1=C(C#N)C=C2NC(C(O)C3=C4C=CNC4=C(C)C=C3C)=NC2=C1 ILRCDGRTLHACEO-UHFFFAOYSA-N 0.000 claims description 4
- CJCDUWWDLYRXMX-UHFFFAOYSA-N 2-[(5,7-dimethyl-1h-indol-4-yl)-hydroxymethyl]-4-methyl-1h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(O)C3=C4C=CNC4=C(C)C=C3C)=NC2=C1C CJCDUWWDLYRXMX-UHFFFAOYSA-N 0.000 claims description 4
- PXNRTYRAHJZFCO-UHFFFAOYSA-N 2-[(5,7-dimethyl-3-phenyl-1h-indol-4-yl)-hydroxymethyl]-3h-benzimidazole-5-carbonitrile Chemical compound C12=C(C(O)C=3NC4=CC=C(C=C4N=3)C#N)C(C)=CC(C)=C2NC=C1C1=CC=CC=C1 PXNRTYRAHJZFCO-UHFFFAOYSA-N 0.000 claims description 4
- IZUKLVOKDFXSKE-UHFFFAOYSA-N 2-[(5,7-dimethyl-3-pyridin-3-yl-1h-indol-4-yl)-hydroxymethyl]-3h-benzimidazole-5-carbonitrile Chemical compound C12=C(C(O)C=3NC4=CC=C(C=C4N=3)C#N)C(C)=CC(C)=C2NC=C1C1=CC=CN=C1 IZUKLVOKDFXSKE-UHFFFAOYSA-N 0.000 claims description 4
- YBKUHYRADHOKPI-UHFFFAOYSA-N 2-[(5-chloro-7-methyl-1h-indol-4-yl)-hydroxymethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(O)C3=C(Cl)C=C(C=4NC=CC=43)C)=NC2=C1 YBKUHYRADHOKPI-UHFFFAOYSA-N 0.000 claims description 4
- NJOJBJOCIYCZOT-UHFFFAOYSA-N 2-[(5-ethoxy-7-methyl-1h-indol-4-yl)-hydroxymethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(O)C3=C4C=CNC4=C(C)C=C3OCC)=NC2=C1 NJOJBJOCIYCZOT-UHFFFAOYSA-N 0.000 claims description 4
- XOGKPRPIAZIAAB-UHFFFAOYSA-N 2-[(5-ethyl-7-methyl-1h-indol-4-yl)-hydroxymethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(O)C3=C4C=CNC4=C(C)C=C3CC)=NC2=C1 XOGKPRPIAZIAAB-UHFFFAOYSA-N 0.000 claims description 4
- JMHZSVHFCSWYIH-UHFFFAOYSA-N 2-[1-(2-aminoethylamino)-2,2,2-trifluoro-1-(5-methoxy-7-methyl-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(NCCN)(C3=C4C=CNC4=C(C)C=C3OC)C(F)(F)F)=NC2=C1 JMHZSVHFCSWYIH-UHFFFAOYSA-N 0.000 claims description 4
- CKJRNYPLQIGZHE-UHFFFAOYSA-N 2-[1-(3-chloro-5-methoxy-7-methyl-1h-indol-4-yl)-1-hydroxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(O)C3=C4C(Cl)=CNC4=C(C)C=C3OC)=NC2=C1 CKJRNYPLQIGZHE-UHFFFAOYSA-N 0.000 claims description 4
- IGYZWJYCDZDCGH-UHFFFAOYSA-N 2-[1-(5,7-dimethyl-1h-indol-4-yl)-1-hydroxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(O)C3=C4C=CNC4=C(C)C=C3C)=NC2=C1 IGYZWJYCDZDCGH-UHFFFAOYSA-N 0.000 claims description 4
- NTXVYWVBRJBBAW-UHFFFAOYSA-N 2-[1-(5,7-dimethyl-1h-indol-4-yl)-1-methoxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2NC=1C(C)(OC)C1=C(C)C=C(C)C2=C1C=CN2 NTXVYWVBRJBBAW-UHFFFAOYSA-N 0.000 claims description 4
- QOWJIYKJRYIXLK-UHFFFAOYSA-N 2-[1-(5-bromo-7-methyl-1h-indol-4-yl)-1-hydroxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(O)C3=C(Br)C=C(C=4NC=CC=43)C)=NC2=C1 QOWJIYKJRYIXLK-UHFFFAOYSA-N 0.000 claims description 4
- WWQHRHXYMPCTCP-UHFFFAOYSA-N 2-[1-(5-bromo-7-methyl-1h-indol-4-yl)-2,2,2-trifluoro-1-(methylamino)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2NC=1C(NC)(C(F)(F)F)C1=C(Br)C=C(C)C2=C1C=CN2 WWQHRHXYMPCTCP-UHFFFAOYSA-N 0.000 claims description 4
- PRMNYNUSJPZLFN-UHFFFAOYSA-N 2-[1-(5-chloro-7-methyl-1h-indol-4-yl)-1-hydroxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(O)C3=C(Cl)C=C(C=4NC=CC=43)C)=NC2=C1 PRMNYNUSJPZLFN-UHFFFAOYSA-N 0.000 claims description 4
- GGMDGBGXROIQMS-UHFFFAOYSA-N 2-[1-(5-cyclopropyl-7-methyl-1h-indol-4-yl)-1-hydroxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2NC=1C(C)(O)C=1C=2C=CNC=2C(C)=CC=1C1CC1 GGMDGBGXROIQMS-UHFFFAOYSA-N 0.000 claims description 4
- WTBXQHFSUJOQFG-UHFFFAOYSA-N 2-[1-(5-cyclopropyl-7-methyl-1h-indol-4-yl)-2,2,2-trifluoro-1-hydroxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2NC=1C(O)(C(F)(F)F)C=1C=2C=CNC=2C(C)=CC=1C1CC1 WTBXQHFSUJOQFG-UHFFFAOYSA-N 0.000 claims description 4
- YWGPLGLNPXQJBT-UHFFFAOYSA-N 2-[1-(5-ethoxy-7-methyl-1h-indol-4-yl)-1-hydroxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(O)C3=C4C=CNC4=C(C)C=C3OCC)=NC2=C1 YWGPLGLNPXQJBT-UHFFFAOYSA-N 0.000 claims description 4
- OUURXFUUEHBLOF-UHFFFAOYSA-N 2-[1-(5-ethoxy-7-methyl-1h-indol-4-yl)-2,2,2-trifluoro-1-hydroxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(O)(C3=C4C=CNC4=C(C)C=C3OCC)C(F)(F)F)=NC2=C1 OUURXFUUEHBLOF-UHFFFAOYSA-N 0.000 claims description 4
- LWIUTERINFAUGJ-UHFFFAOYSA-N 2-[1-(5-ethyl-7-methyl-1h-indol-4-yl)-1-hydroxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(O)C3=C4C=CNC4=C(C)C=C3CC)=NC2=C1 LWIUTERINFAUGJ-UHFFFAOYSA-N 0.000 claims description 4
- YYGWYVHSHGNNJL-UHFFFAOYSA-N 2-[1-(5-ethyl-7-methyl-1h-indol-4-yl)-2,2,2-trifluoro-1-(methylamino)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(NC)(C3=C4C=CNC4=C(C)C=C3CC)C(F)(F)F)=NC2=C1 YYGWYVHSHGNNJL-UHFFFAOYSA-N 0.000 claims description 4
- UEKKATWRUPJCBD-UHFFFAOYSA-N 2-[1-(5-ethyl-7-methyl-1h-indol-4-yl)-2,2,2-trifluoro-1-hydroxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(O)(C3=C4C=CNC4=C(C)C=C3CC)C(F)(F)F)=NC2=C1 UEKKATWRUPJCBD-UHFFFAOYSA-N 0.000 claims description 4
- HXDQCQSUNIJZRK-UHFFFAOYSA-N 2-[1-(5-ethyl-7-methyl-1h-indol-4-yl)-2,2,2-trifluoro-1-methoxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(OC)(C3=C4C=CNC4=C(C)C=C3CC)C(F)(F)F)=NC2=C1 HXDQCQSUNIJZRK-UHFFFAOYSA-N 0.000 claims description 4
- XUVJPWXHCZSGDX-UHFFFAOYSA-N 2-[1-(5-methoxy-7-methyl-1h-indol-4-yl)-1-(methylamino)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2NC=1C(C)(NC)C1=C(OC)C=C(C)C2=C1C=CN2 XUVJPWXHCZSGDX-UHFFFAOYSA-N 0.000 claims description 4
- NTBOIAVZHFCBRE-UHFFFAOYSA-N 2-[1-(6-fluoro-5-methoxy-7-methyl-1h-indol-4-yl)-1-methoxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound C1=C(C#N)C=C2NC(C(C)(OC)C3=C4C=CNC4=C(C)C(F)=C3OC)=NC2=C1 NTBOIAVZHFCBRE-UHFFFAOYSA-N 0.000 claims description 4
- RFHMXZPYVSYFRT-UHFFFAOYSA-N 2-[1-[5-(cyclopropylmethoxy)-7-methyl-1h-indol-4-yl]-1-hydroxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2NC=1C(C)(O)C=1C=2C=CNC=2C(C)=CC=1OCC1CC1 RFHMXZPYVSYFRT-UHFFFAOYSA-N 0.000 claims description 4
- PLHVOBWJJCGEDT-UHFFFAOYSA-N 2-[1-[5-(difluoromethoxy)-7-methyl-1h-indol-4-yl]-1-hydroxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(O)C3=C(OC(F)F)C=C(C=4NC=CC=43)C)=NC2=C1 PLHVOBWJJCGEDT-UHFFFAOYSA-N 0.000 claims description 4
- DYQZYFCTIFILNK-UHFFFAOYSA-N 2-[1-[5-(difluoromethoxy)-7-methyl-1h-indol-4-yl]-1-methoxyethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2NC=1C(C)(OC)C1=C(OC(F)F)C=C(C)C2=C1C=CN2 DYQZYFCTIFILNK-UHFFFAOYSA-N 0.000 claims description 4
- QWHRNESVNDHDPP-UHFFFAOYSA-N 2-[1-amino-1-(5,7-dimethyl-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(N)C3=C4C=CNC4=C(C)C=C3C)=NC2=C1 QWHRNESVNDHDPP-UHFFFAOYSA-N 0.000 claims description 4
- PGUFILDPJISUNW-UHFFFAOYSA-N 2-[1-amino-1-(5-bromo-7-methyl-1h-indol-4-yl)-2,2,2-trifluoroethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(N)(C3=C(Br)C=C(C=4NC=CC=43)C)C(F)(F)F)=NC2=C1 PGUFILDPJISUNW-UHFFFAOYSA-N 0.000 claims description 4
- JBUQWZQKVOMXHM-UHFFFAOYSA-N 2-[1-amino-1-(5-bromo-7-methyl-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(N)C3=C(Br)C=C(C=4NC=CC=43)C)=NC2=C1 JBUQWZQKVOMXHM-UHFFFAOYSA-N 0.000 claims description 4
- LPIZKNKQMMXDML-UHFFFAOYSA-N 2-[1-amino-1-(5-cyclopropyl-7-methyl-1h-indol-4-yl)-2,2,2-trifluoroethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2NC=1C(N)(C(F)(F)F)C=1C=2C=CNC=2C(C)=CC=1C1CC1 LPIZKNKQMMXDML-UHFFFAOYSA-N 0.000 claims description 4
- CSCYUIHDRJAFQA-UHFFFAOYSA-N 2-[1-amino-1-(5-cyclopropyl-7-methyl-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2NC=1C(C)(N)C=1C=2C=CNC=2C(C)=CC=1C1CC1 CSCYUIHDRJAFQA-UHFFFAOYSA-N 0.000 claims description 4
- YTVNCXNRPLAABC-UHFFFAOYSA-N 2-[1-amino-1-(5-ethyl-7-methyl-1h-indol-4-yl)-2,2,2-trifluoroethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(N)(C3=C4C=CNC4=C(C)C=C3CC)C(F)(F)F)=NC2=C1 YTVNCXNRPLAABC-UHFFFAOYSA-N 0.000 claims description 4
- IKAAPGCDXGGGNY-UHFFFAOYSA-N 2-[1-amino-1-(5-ethyl-7-methyl-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(N)C3=C4C=CNC4=C(C)C=C3CC)=NC2=C1 IKAAPGCDXGGGNY-UHFFFAOYSA-N 0.000 claims description 4
- LSTLZVVIZOILKX-UHFFFAOYSA-N 2-[1-amino-1-(5-methoxy-7-methyl-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(N)C3=C4C=CNC4=C(C)C=C3OC)=NC2=C1 LSTLZVVIZOILKX-UHFFFAOYSA-N 0.000 claims description 4
- ZYBXRYCASNAQHI-UHFFFAOYSA-N 2-[1-amino-1-(7-methyl-5-methylsulfonyl-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(N)C3=C(C=C(C=4NC=CC=43)C)S(C)(=O)=O)=NC2=C1 ZYBXRYCASNAQHI-UHFFFAOYSA-N 0.000 claims description 4
- AGXOXQQOMYCSKD-UHFFFAOYSA-N 2-[1-amino-1-(7-methyl-5-propan-2-yl-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(N)C3=C4C=CNC4=C(C)C=C3C(C)C)=NC2=C1 AGXOXQQOMYCSKD-UHFFFAOYSA-N 0.000 claims description 4
- DEVLEXATRAXCTI-UHFFFAOYSA-N 2-[1-amino-1-[5-(difluoromethoxy)-7-methyl-1h-indol-4-yl]ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(N)C3=C(OC(F)F)C=C(C=4NC=CC=43)C)=NC2=C1 DEVLEXATRAXCTI-UHFFFAOYSA-N 0.000 claims description 4
- OJPVIRTVYXTSRA-UHFFFAOYSA-N 2-[1-amino-2,2,2-trifluoro-1-(5-methoxy-7-methyl-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(N)(C3=C4C=CNC4=C(C)C=C3OC)C(F)(F)F)=NC2=C1 OJPVIRTVYXTSRA-UHFFFAOYSA-N 0.000 claims description 4
- CGLIDKMUNVHAHJ-UHFFFAOYSA-N 2-[1-hydroxy-1-(5-methoxy-7-methyl-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(O)C3=C4C=CNC4=C(C)C=C3OC)=NC2=C1 CGLIDKMUNVHAHJ-UHFFFAOYSA-N 0.000 claims description 4
- UVZPKPOVHODPKR-UHFFFAOYSA-N 2-[1-hydroxy-1-(7-methyl-5-methylsulfonyl-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(O)C3=C(C=C(C=4NC=CC=43)C)S(C)(=O)=O)=NC2=C1 UVZPKPOVHODPKR-UHFFFAOYSA-N 0.000 claims description 4
- FGGUCKRQQREHSH-UHFFFAOYSA-N 2-[1-hydroxy-1-(7-methyl-5-propan-2-yl-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(O)C3=C4C=CNC4=C(C)C=C3C(C)C)=NC2=C1 FGGUCKRQQREHSH-UHFFFAOYSA-N 0.000 claims description 4
- JDQMGQFRFUJDRM-UHFFFAOYSA-N 2-[1-hydroxy-1-(7-methyl-5-propan-2-yloxy-1h-indol-4-yl)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(O)C3=C4C=CNC4=C(C)C=C3OC(C)C)=NC2=C1 JDQMGQFRFUJDRM-UHFFFAOYSA-N 0.000 claims description 4
- KXKHCXNKUSWQEL-UHFFFAOYSA-N 2-[1-hydroxy-1-(7-methyl-5-propan-2-yloxy-1h-indol-4-yl)propyl]-3h-benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2NC=1C(O)(CC)C1=C(OC(C)C)C=C(C)C2=C1C=CN2 KXKHCXNKUSWQEL-UHFFFAOYSA-N 0.000 claims description 4
- OJWKBVFOIPIVOU-UHFFFAOYSA-N 2-[1-hydroxy-1-[7-methyl-5-(2-methylpropyl)-1h-indol-4-yl]ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N#CC1=CC=C2NC(C(C)(O)C3=C4C=CNC4=C(C)C=C3CC(C)C)=NC2=C1 OJWKBVFOIPIVOU-UHFFFAOYSA-N 0.000 claims description 4
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| EP2970269B1 (en) * | 2013-03-14 | 2017-04-19 | Novartis AG | 2-(1h-indol-4-ylmethyl)-3h-imidazo[4,5-b]pyridine-6-carbonitrile derivatives as complement factor b inhibitors useful for the treatment of ophthalmic diseases |
| JO3425B1 (ar) | 2013-07-15 | 2019-10-20 | Novartis Ag | مشتقات البابيريدينيل-اندول واستخدامها كعامل متمم لمثبطات b |
| EP3089963A1 (en) * | 2013-10-30 | 2016-11-09 | Novartis AG | 2-benzyl-benzimidazole complement factor b inhibitors and uses thereof |
| CN103755622A (zh) * | 2013-12-25 | 2014-04-30 | 华东理工大学 | 合成4,5,6,7-四氘代吲哚-3-乙酸的方法 |
| WO2017035408A1 (en) | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Compounds for treatment of immune and inflammatory disorders |
| AR106018A1 (es) | 2015-08-26 | 2017-12-06 | Achillion Pharmaceuticals Inc | Compuestos de arilo, heteroarilo y heterocíclicos para el tratamiento de trastornos médicos |
| TWI854164B (zh) | 2016-02-01 | 2024-09-01 | 美商百歐克斯製藥公司 | 苯并吡唑化合物及其類似物 |
| RU2018145364A (ru) * | 2016-06-27 | 2020-07-28 | Ачиллион Фармасьютикалс, Инк. | Хиназолиновые и индольные соединения для лечения медицинских нарушений |
| CN110603252A (zh) | 2017-03-01 | 2019-12-20 | 艾其林医药公司 | 用于治疗医学障碍的芳基、杂芳基和杂环药物化合物 |
| TWI873092B (zh) * | 2018-04-06 | 2025-02-21 | 美商百歐克斯製藥公司 | 取代的苯并呋喃、苯并吡咯、苯并噻吩及結構相關的補體抑制劑 |
| WO2020041301A1 (en) | 2018-08-20 | 2020-02-27 | Achillion Pharmaceuticals, Inc. | Pharmaceutical compounds for the treatment of complement factor d medical disorders |
| WO2020051532A2 (en) | 2018-09-06 | 2020-03-12 | Achillion Pharmaceuticals, Inc. | Macrocyclic compounds for the treatment of medical disorders |
| US11814363B2 (en) | 2018-09-06 | 2023-11-14 | Achillion Pharmaceuticals, Inc. | Morphic forms of danicopan |
| BR112021005506A2 (pt) | 2018-09-25 | 2021-06-15 | Achillion Pharmaceuticals, Inc. | formas mórficas de inibidores de fator complementar d |
| WO2021168320A1 (en) | 2020-02-20 | 2021-08-26 | Achillion Pharmaceuticals, Inc. | Heteroaryl compounds for treatment of complement factor d mediated disorders |
| CA3179686A1 (en) * | 2020-04-07 | 2021-10-14 | UCB Biopharma SRL | Difluorocyclohexyl derivatives as il-17 modulators |
| CN114057758A (zh) | 2020-08-07 | 2022-02-18 | 上海美悦生物科技发展有限公司 | 补体因子b抑制剂及其药物组合物、制备方法和用途 |
| EP4194449A4 (en) | 2020-08-07 | 2024-03-20 | Shanghai Meiyue Biotech Development Co., Ltd. | Heterocyclic compound, preparation method therefor and use thereof |
| WO2022066774A1 (en) | 2020-09-23 | 2022-03-31 | Achillion Pharmaceuticals, Inc. | Pharmaceutical compounds for the treatment of complement mediated disorders |
| US20240287034A1 (en) * | 2021-06-03 | 2024-08-29 | Chinook Therapeutics, Inc. | Substituted indole compounds and methods of use thereof |
| CA3242815A1 (en) | 2022-01-26 | 2023-08-03 | Shanghai Meiyue Biotech Development Co., Ltd. | Salt type and crystal form of complement factor b inhibitor, and preparation method therefor and application thereof |
| CN119137099A (zh) * | 2022-04-01 | 2024-12-13 | 诺华股份有限公司 | 补体因子b抑制剂及其用途 |
| EP4617266A1 (en) | 2022-11-11 | 2025-09-17 | Shanghai Yisheng Biopharmaceutical company Limited | Piperidine-substituted benzoic acid compound, and pharmaceutical composition and use thereof |
| JP2026502231A (ja) * | 2022-12-31 | 2026-01-21 | チューハイ ユナイテッド ラボラトリーズ シーオー．，エルティーディー． | 補体因子ｂ阻害剤、その医薬組成物および使用 |
| IL325759A (en) | 2023-07-04 | 2026-03-01 | Sitala Bio Ltd | History of 2-(1H-indol-4-yl)methyl)2H-indazole as factor B inhibitors |
| IL325760A (en) | 2023-07-04 | 2026-03-01 | Sitala Bio Ltd | History of 2-(1H-indol-4-yl)methyl)-isoindoline as factor B inhibitors |
| WO2025008516A2 (en) | 2023-07-06 | 2025-01-09 | Sitala Bio Ltd | Novel compounds |
| WO2025008517A1 (en) | 2023-07-06 | 2025-01-09 | Sitala Bio Ltd | Indole derivatives with factor b inhibitory activity |
| CN119371402A (zh) | 2023-07-26 | 2025-01-28 | 上海美悦生物科技发展有限公司 | 螺环烯基类或氮杂烯基类化合物及其药物组合物、制备方法和用途 |
| WO2025172535A1 (en) | 2024-02-15 | 2025-08-21 | Sitala Bio Ltd | Indole and benzimidazole compounds as factor b inhibitors |
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| PT72878B (en) | 1980-04-24 | 1983-03-29 | Merck & Co Inc | Process for preparing mannich-base hydroxamic acid pro-drugs for the improved delivery of non-steroidal anti-inflammatory agents |
| GB8420919D0 (en) * | 1984-08-17 | 1984-09-19 | Beecham Group Plc | Compounds |
| DE19545464A1 (de) * | 1995-12-06 | 1997-06-12 | Bayer Ag | Benzimidazol-isoindoleninfarbstoffe |
| CN100415723C (zh) * | 2000-01-17 | 2008-09-03 | 帝人株式会社 | 苯并咪唑衍生物 |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| GB0400781D0 (en) * | 2004-01-14 | 2004-02-18 | Novartis Ag | Organic compounds |
| US7488752B2 (en) * | 2004-10-08 | 2009-02-10 | Schering Corporation | Thrombin receptor antagonists |
| WO2007034277A1 (en) * | 2005-09-19 | 2007-03-29 | Pfizer Products Inc. | Aryl substituted imidazo [4,5-c] pyridine compounds as c3a receptor antagonists |
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| JO3265B1 (ar) * | 2008-12-09 | 2018-09-16 | Novartis Ag | مثبطات بيريديلوكسى اندولات vegf-r2 واستخدامها لعلاج المرض |
| CA2965223C (en) * | 2008-12-22 | 2019-09-24 | Chemocentryx, Inc. | C5ar antagonists |
| AU2010216239B2 (en) * | 2009-02-18 | 2012-06-14 | Amgen Inc. | Indole/benzimidazole compounds as mTOR kinase inhibitors |
| EP2447263A1 (en) * | 2010-09-27 | 2012-05-02 | Bioprojet | Benzazole derivatives as histamine H4 receptor ligands |
| US8846656B2 (en) * | 2011-07-22 | 2014-09-30 | Novartis Ag | Tetrahydropyrido-pyridine and tetrahydropyrido-pyrimidine compounds and use thereof as C5a receptor modulators |
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