RU2015119640A - Соединения n-замещенного индазол-сульфонамида с избирательной активностью в потенциал-зависимых натриевых каналах - Google Patents
Соединения n-замещенного индазол-сульфонамида с избирательной активностью в потенциал-зависимых натриевых каналах Download PDFInfo
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- RU2015119640A RU2015119640A RU2015119640A RU2015119640A RU2015119640A RU 2015119640 A RU2015119640 A RU 2015119640A RU 2015119640 A RU2015119640 A RU 2015119640A RU 2015119640 A RU2015119640 A RU 2015119640A RU 2015119640 A RU2015119640 A RU 2015119640A
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- Prior art keywords
- sulfonamide
- indazole
- fluoro
- alkyl
- ethyl
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- -1 N-SUBSTITUTED INDAZOL SULFONAMIDE Chemical class 0.000 title claims abstract 57
- 150000001875 compounds Chemical class 0.000 title claims abstract 18
- 108010052164 Sodium Channels Proteins 0.000 title 1
- 102000018674 Sodium Channels Human genes 0.000 title 1
- 230000001419 dependent effect Effects 0.000 title 1
- 230000000694 effects Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 55
- 125000003118 aryl group Chemical group 0.000 claims abstract 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract 21
- 150000002367 halogens Chemical class 0.000 claims abstract 21
- 125000001424 substituent group Chemical group 0.000 claims abstract 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 19
- 150000003839 salts Chemical class 0.000 claims abstract 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 14
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000003435 aroyl group Chemical group 0.000 claims abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract 8
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims abstract 8
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 8
- 125000002252 acyl group Chemical group 0.000 claims abstract 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract 7
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract 7
- 125000005110 aryl thio group Chemical group 0.000 claims abstract 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 7
- 125000004475 heteroaralkyl group Chemical group 0.000 claims abstract 7
- 125000005368 heteroarylthio group Chemical group 0.000 claims abstract 7
- 239000001257 hydrogen Substances 0.000 claims abstract 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 7
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims abstract 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 5
- 125000006413 ring segment Chemical group 0.000 claims abstract 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 5
- 239000011593 sulfur Substances 0.000 claims abstract 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 4
- 208000004296 neuralgia Diseases 0.000 claims 4
- 208000021722 neuropathic pain Diseases 0.000 claims 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims 4
- 150000003254 radicals Chemical class 0.000 claims 4
- HLIFNQCITGTXJX-DRMXPCRNSA-N 1-[(1r)-1-[2-[2-[(1r,2r)-2-aminocyclohexyl]ethynyl]phenyl]ethyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound C1([C@@H](C)N2C3=CC(F)=C(C=C3C=N2)S(=O)(=O)NC=2N=C(F)C=CC=2)=CC=CC=C1C#C[C@H]1CCCC[C@H]1N HLIFNQCITGTXJX-DRMXPCRNSA-N 0.000 claims 3
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims 3
- HVWTWZVZVXUYQD-OAHLLOKOSA-N 1-[(1r)-1-[2-(3-aminoprop-1-ynyl)phenyl]ethyl]-6-fluoro-n-(5-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound C1([C@@H](C)N2C3=CC(F)=C(C=C3C=N2)S(=O)(=O)NC=2N=CC(F)=CC=2)=CC=CC=C1C#CCN HVWTWZVZVXUYQD-OAHLLOKOSA-N 0.000 claims 2
- MWZYREDWISDWKN-OAHLLOKOSA-N 1-[(1r)-1-[2-(3-aminoprop-1-ynyl)phenyl]ethyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound C1([C@@H](C)N2C3=CC(F)=C(C=C3C=N2)S(=O)(=O)NC=2N=C(F)C=CC=2)=CC=CC=C1C#CCN MWZYREDWISDWKN-OAHLLOKOSA-N 0.000 claims 2
- FEAHGBOVOCTTFJ-CYBMUJFWSA-N 1-[(1r)-1-[2-(3-aminoprop-1-ynyl)phenyl]ethyl]-n-(5-chloro-1,3-thiazol-2-yl)-6-fluoroindazole-5-sulfonamide Chemical compound C1([C@@H](C)N2C3=CC(F)=C(C=C3C=N2)S(=O)(=O)NC=2SC(Cl)=CN=2)=CC=CC=C1C#CCN FEAHGBOVOCTTFJ-CYBMUJFWSA-N 0.000 claims 2
- CAIALQMFYYGXBJ-OAHLLOKOSA-N 1-[(1r)-1-[2-(3-aminopropyl)phenyl]ethyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound C1([C@@H](C)N2C3=CC(F)=C(C=C3C=N2)S(=O)(=O)NC=2N=C(F)C=CC=2)=CC=CC=C1CCCN CAIALQMFYYGXBJ-OAHLLOKOSA-N 0.000 claims 2
- WCWKMFXFWHIFGR-CQSZACIVSA-N 1-[(1r)-1-[2-(azetidin-3-yl)phenyl]ethyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound C1([C@@H](C)N2C3=CC(F)=C(C=C3C=N2)S(=O)(=O)NC=2N=C(F)C=CC=2)=CC=CC=C1C1CNC1 WCWKMFXFWHIFGR-CQSZACIVSA-N 0.000 claims 2
- HLIFNQCITGTXJX-WWEVIYMKSA-N 1-[(1r)-1-[2-[2-[(1s,2s)-2-aminocyclohexyl]ethynyl]phenyl]ethyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound C1([C@@H](C)N2C3=CC(F)=C(C=C3C=N2)S(=O)(=O)NC=2N=C(F)C=CC=2)=CC=CC=C1C#C[C@@H]1CCCC[C@@H]1N HLIFNQCITGTXJX-WWEVIYMKSA-N 0.000 claims 2
- HLIFNQCITGTXJX-UHFFFAOYSA-N 1-[1-[2-[2-(2-aminocyclohexyl)ethynyl]phenyl]ethyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound N1=CC2=CC(S(=O)(=O)NC=3N=C(F)C=CC=3)=C(F)C=C2N1C(C)C1=CC=CC=C1C#CC1CCCCC1N HLIFNQCITGTXJX-UHFFFAOYSA-N 0.000 claims 2
- DBZJNIHBDORRII-OAHLLOKOSA-N 1-[[(7r)-7-amino-5,6,7,8-tetrahydronaphthalen-1-yl]methyl]-6-fluoro-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C([C@H](CC1=2)N)CC1=CC=CC=2CN(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=NC=NS1 DBZJNIHBDORRII-OAHLLOKOSA-N 0.000 claims 2
- RHZYYEZFTCJSBE-GFCCVEGCSA-N 6-fluoro-1-[(1r)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound FC=1C=C2N([C@@H](C=3C=4CNCCC=4C=CC=3)C)N=CC2=CC=1S(=O)(=O)NC1=NC=NS1 RHZYYEZFTCJSBE-GFCCVEGCSA-N 0.000 claims 2
- YCZYLEYBYBXZRB-CYBMUJFWSA-N 6-fluoro-1-[(1r)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]-n-(1,3-thiazol-2-yl)indazole-5-sulfonamide Chemical compound FC=1C=C2N([C@@H](C=3C=4CNCCC=4C=CC=3)C)N=CC2=CC=1S(=O)(=O)NC1=NC=CS1 YCZYLEYBYBXZRB-CYBMUJFWSA-N 0.000 claims 2
- ZQLOTXCADLUPOP-LLVKDONJSA-N 6-fluoro-1-[(1r)-1-phenylethyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C1([C@@H](C)N2C3=CC(F)=C(C=C3C=N2)S(=O)(=O)NC=2SN=CN=2)=CC=CC=C1 ZQLOTXCADLUPOP-LLVKDONJSA-N 0.000 claims 2
- MTXZEXIUQKVXSK-CQSZACIVSA-N 6-fluoro-n-(5-fluoropyridin-2-yl)-1-[(1r)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]indazole-5-sulfonamide Chemical compound FC=1C=C2N([C@@H](C=3C=4CNCCC=4C=CC=3)C)N=CC2=CC=1S(=O)(=O)NC1=CC=C(F)C=N1 MTXZEXIUQKVXSK-CQSZACIVSA-N 0.000 claims 2
- BDXVDLWUWAYQKL-CQSZACIVSA-N 6-fluoro-n-(6-fluoropyridin-2-yl)-1-[(1r)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]indazole-5-sulfonamide Chemical compound FC=1C=C2N([C@@H](C=3C=4CNCCC=4C=CC=3)C)N=CC2=CC=1S(=O)(=O)NC1=CC=CC(F)=N1 BDXVDLWUWAYQKL-CQSZACIVSA-N 0.000 claims 2
- QMJIVIHONRHYGL-MRXNPFEDSA-N 6-fluoro-n-(6-fluoropyridin-2-yl)-1-[(1r)-1-(2-piperidin-4-ylphenyl)ethyl]indazole-5-sulfonamide Chemical compound C1([C@@H](C)N2C3=CC(F)=C(C=C3C=N2)S(=O)(=O)NC=2N=C(F)C=CC=2)=CC=CC=C1C1CCNCC1 QMJIVIHONRHYGL-MRXNPFEDSA-N 0.000 claims 2
- SRBXSJAKGQJETP-MRXNPFEDSA-N 6-fluoro-n-(6-fluoropyridin-2-yl)-1-[(1r)-1-[2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]ethyl]indazole-5-sulfonamide Chemical compound C1([C@@H](C)N2C3=CC(F)=C(C=C3C=N2)S(=O)(=O)NC=2N=C(F)C=CC=2)=CC=CC=C1C1=CCNCC1 SRBXSJAKGQJETP-MRXNPFEDSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- KVCFFRVMHFWXRQ-GFCCVEGCSA-N n-(5-chloro-1,3-thiazol-2-yl)-6-fluoro-1-[(1r)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]indazole-5-sulfonamide Chemical compound FC=1C=C2N([C@@H](C=3C=4CNCCC=4C=CC=3)C)N=CC2=CC=1S(=O)(=O)NC1=NC=C(Cl)S1 KVCFFRVMHFWXRQ-GFCCVEGCSA-N 0.000 claims 2
- JXVAEAWLORTHQW-GFCCVEGCSA-N n-(5-chloro-1,3-thiazol-2-yl)-6-fluoro-2-[(1r)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]indazole-5-sulfonamide Chemical compound FC1=CC2=NN([C@@H](C=3C=4CNCCC=4C=CC=3)C)C=C2C=C1S(=O)(=O)NC1=NC=C(Cl)S1 JXVAEAWLORTHQW-GFCCVEGCSA-N 0.000 claims 2
- CSCJDGKSKWJIBP-MRXNPFEDSA-N n-(6-fluoropyridin-2-yl)-6-methyl-1-[(1r)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]indazole-5-sulfonamide Chemical compound CC=1C=C2N([C@@H](C=3C=4CNCCC=4C=CC=3)C)N=CC2=CC=1S(=O)(=O)NC1=CC=CC(F)=N1 CSCJDGKSKWJIBP-MRXNPFEDSA-N 0.000 claims 2
- BJAWBFPYZRHYLC-UHFFFAOYSA-N 1-(2,3-dihydro-1h-isoindol-4-ylmethyl)-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C(=CC=3N(CC=4C=5CNCC=5C=CC=4)N=CC=3C=2)F)=N1 BJAWBFPYZRHYLC-UHFFFAOYSA-N 0.000 claims 1
- AYFXUDMBPRBAPJ-UHFFFAOYSA-N 1-[(2-amino-2,3-dihydro-1h-inden-4-yl)methyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound C=12CC(N)CC2=CC=CC=1CN(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=CC=CC(F)=N1 AYFXUDMBPRBAPJ-UHFFFAOYSA-N 0.000 claims 1
- DBZJNIHBDORRII-UHFFFAOYSA-N 1-[(7-amino-5,6,7,8-tetrahydronaphthalen-1-yl)methyl]-6-fluoro-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C=12CC(N)CCC2=CC=CC=1CN(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=NC=NS1 DBZJNIHBDORRII-UHFFFAOYSA-N 0.000 claims 1
- UKZBXRYSYXZVOR-UHFFFAOYSA-N 1-[(7-amino-5,6,7,8-tetrahydronaphthalen-1-yl)methyl]-6-fluoro-n-(1,3-thiazol-2-yl)indazole-5-sulfonamide Chemical compound C=12CC(N)CCC2=CC=CC=1CN(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=NC=CS1 UKZBXRYSYXZVOR-UHFFFAOYSA-N 0.000 claims 1
- MNUGLDCSCOZYSQ-UHFFFAOYSA-N 1-[(7-amino-5,6,7,8-tetrahydronaphthalen-1-yl)methyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound C=12CC(N)CCC2=CC=CC=1CN(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=CC=CC(F)=N1 MNUGLDCSCOZYSQ-UHFFFAOYSA-N 0.000 claims 1
- GQZRFXWUYDBETK-UHFFFAOYSA-N 1-[(7-amino-5,6,7,8-tetrahydronaphthalen-1-yl)methyl]-6-methyl-n-(1,3-thiazol-2-yl)indazole-5-sulfonamide Chemical compound CC1=CC=2N(CC=3C=4CC(N)CCC=4C=CC=3)N=CC=2C=C1S(=O)(=O)NC1=NC=CS1 GQZRFXWUYDBETK-UHFFFAOYSA-N 0.000 claims 1
- PXUKNVBPQYBNED-UHFFFAOYSA-N 1-[(7-amino-5,6,7,8-tetrahydronaphthalen-1-yl)methyl]-n-(5-chloro-1,3-thiazol-2-yl)-6-fluoroindazole-5-sulfonamide Chemical compound C=12CC(N)CCC2=CC=CC=1CN(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=NC=C(Cl)S1 PXUKNVBPQYBNED-UHFFFAOYSA-N 0.000 claims 1
- HZYSPABGTGUJPY-UHFFFAOYSA-N 1-[(7-amino-5,6,7,8-tetrahydronaphthalen-1-yl)methyl]-n-(6-fluoropyridin-2-yl)-6-methylindazole-5-sulfonamide Chemical compound CC1=CC=2N(CC=3C=4CC(N)CCC=4C=CC=3)N=CC=2C=C1S(=O)(=O)NC1=CC=CC(F)=N1 HZYSPABGTGUJPY-UHFFFAOYSA-N 0.000 claims 1
- HVWTWZVZVXUYQD-UHFFFAOYSA-N 1-[1-[2-(3-aminoprop-1-ynyl)phenyl]ethyl]-6-fluoro-n-(5-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound N1=CC2=CC(S(=O)(=O)NC=3N=CC(F)=CC=3)=C(F)C=C2N1C(C)C1=CC=CC=C1C#CCN HVWTWZVZVXUYQD-UHFFFAOYSA-N 0.000 claims 1
- MWZYREDWISDWKN-UHFFFAOYSA-N 1-[1-[2-(3-aminoprop-1-ynyl)phenyl]ethyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound N1=CC2=CC(S(=O)(=O)NC=3N=C(F)C=CC=3)=C(F)C=C2N1C(C)C1=CC=CC=C1C#CCN MWZYREDWISDWKN-UHFFFAOYSA-N 0.000 claims 1
- FEAHGBOVOCTTFJ-UHFFFAOYSA-N 1-[1-[2-(3-aminoprop-1-ynyl)phenyl]ethyl]-n-(5-chloro-1,3-thiazol-2-yl)-6-fluoroindazole-5-sulfonamide Chemical compound N1=CC2=CC(S(=O)(=O)NC=3SC(Cl)=CN=3)=C(F)C=C2N1C(C)C1=CC=CC=C1C#CCN FEAHGBOVOCTTFJ-UHFFFAOYSA-N 0.000 claims 1
- CAIALQMFYYGXBJ-UHFFFAOYSA-N 1-[1-[2-(3-aminopropyl)phenyl]ethyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound N1=CC2=CC(S(=O)(=O)NC=3N=C(F)C=CC=3)=C(F)C=C2N1C(C)C1=CC=CC=C1CCCN CAIALQMFYYGXBJ-UHFFFAOYSA-N 0.000 claims 1
- WCWKMFXFWHIFGR-UHFFFAOYSA-N 1-[1-[2-(azetidin-3-yl)phenyl]ethyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound N1=CC2=CC(S(=O)(=O)NC=3N=C(F)C=CC=3)=C(F)C=C2N1C(C)C1=CC=CC=C1C1CNC1 WCWKMFXFWHIFGR-UHFFFAOYSA-N 0.000 claims 1
- UKZBXRYSYXZVOR-MRXNPFEDSA-N 1-[[(7r)-7-amino-5,6,7,8-tetrahydronaphthalen-1-yl]methyl]-6-fluoro-n-(1,3-thiazol-2-yl)indazole-5-sulfonamide Chemical compound C([C@H](CC1=2)N)CC1=CC=CC=2CN(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=NC=CS1 UKZBXRYSYXZVOR-MRXNPFEDSA-N 0.000 claims 1
- MNUGLDCSCOZYSQ-QGZVFWFLSA-N 1-[[(7r)-7-amino-5,6,7,8-tetrahydronaphthalen-1-yl]methyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound C([C@H](CC1=2)N)CC1=CC=CC=2CN(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=CC=CC(F)=N1 MNUGLDCSCOZYSQ-QGZVFWFLSA-N 0.000 claims 1
- DBZJNIHBDORRII-HNNXBMFYSA-N 1-[[(7s)-7-amino-5,6,7,8-tetrahydronaphthalen-1-yl]methyl]-6-fluoro-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C([C@@H](CC1=2)N)CC1=CC=CC=2CN(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=NC=NS1 DBZJNIHBDORRII-HNNXBMFYSA-N 0.000 claims 1
- UKZBXRYSYXZVOR-INIZCTEOSA-N 1-[[(7s)-7-amino-5,6,7,8-tetrahydronaphthalen-1-yl]methyl]-6-fluoro-n-(1,3-thiazol-2-yl)indazole-5-sulfonamide Chemical compound C([C@@H](CC1=2)N)CC1=CC=CC=2CN(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=NC=CS1 UKZBXRYSYXZVOR-INIZCTEOSA-N 0.000 claims 1
- MNUGLDCSCOZYSQ-KRWDZBQOSA-N 1-[[(7s)-7-amino-5,6,7,8-tetrahydronaphthalen-1-yl]methyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound C([C@@H](CC1=2)N)CC1=CC=CC=2CN(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=CC=CC(F)=N1 MNUGLDCSCOZYSQ-KRWDZBQOSA-N 0.000 claims 1
- HCYBVAJMNZELNV-UHFFFAOYSA-N 1-[[2-(1,2,3,4-tetrahydroisoquinolin-5-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C=1C=C2N(CC=3C(=CC=CC=3)C=3C=4CCNCC=4C=CC=3)N=CC2=CC=1S(=O)(=O)NC1=NC=NS1 HCYBVAJMNZELNV-UHFFFAOYSA-N 0.000 claims 1
- KPEIQQYVHAGHIA-UHFFFAOYSA-N 1-[[2-(2,3,4,7-tetrahydro-1h-azepin-5-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C=1C=C2N(CC=3C(=CC=CC=3)C=3CCCNCC=3)N=CC2=CC=1S(=O)(=O)NC1=NC=NS1 KPEIQQYVHAGHIA-UHFFFAOYSA-N 0.000 claims 1
- IZQQSZDILYAADY-UHFFFAOYSA-N 1-[[2-(2-amino-1-fluoroethyl)phenyl]methyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound NCC(F)C1=CC=CC=C1CN1C2=CC(F)=C(S(=O)(=O)NC=3N=C(F)C=CC=3)C=C2C=N1 IZQQSZDILYAADY-UHFFFAOYSA-N 0.000 claims 1
- KJXORRSVLNZSBG-UHFFFAOYSA-N 1-[[2-(2-aminoethyl)phenyl]methyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound NCCC1=CC=CC=C1CN1C2=CC(F)=C(S(=O)(=O)NC=3N=C(F)C=CC=3)C=C2C=N1 KJXORRSVLNZSBG-UHFFFAOYSA-N 0.000 claims 1
- QQCKTCAETHZJCK-UHFFFAOYSA-N 1-[[2-(3-aminoprop-1-ynyl)phenyl]methyl]-6-fluoro-n-(1,3-thiazol-2-yl)indazole-5-sulfonamide Chemical compound NCC#CC1=CC=CC=C1CN1C2=CC(F)=C(S(=O)(=O)NC=3SC=CN=3)C=C2C=N1 QQCKTCAETHZJCK-UHFFFAOYSA-N 0.000 claims 1
- DTUSTJJVJJTMGW-UHFFFAOYSA-N 1-[[2-(3-aminopropyl)phenyl]methyl]-6-fluoro-n-(1,3-thiazol-2-yl)indazole-5-sulfonamide Chemical compound NCCCC1=CC=CC=C1CN1C2=CC(F)=C(S(=O)(=O)NC=3SC=CN=3)C=C2C=N1 DTUSTJJVJJTMGW-UHFFFAOYSA-N 0.000 claims 1
- IOCLELURYWJHAP-UHFFFAOYSA-N 1-[[2-(3-aminopropyl)phenyl]methyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound NCCCC1=CC=CC=C1CN1C2=CC(F)=C(S(=O)(=O)NC=3N=C(F)C=CC=3)C=C2C=N1 IOCLELURYWJHAP-UHFFFAOYSA-N 0.000 claims 1
- CYDWOBCBPTYJCC-UHFFFAOYSA-N 1-[[2-(4-amino-4-methylpent-1-ynyl)phenyl]methyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound CC(C)(N)CC#CC1=CC=CC=C1CN1C2=CC(F)=C(S(=O)(=O)NC=3N=C(F)C=CC=3)C=C2C=N1 CYDWOBCBPTYJCC-UHFFFAOYSA-N 0.000 claims 1
- KXFJWALCQLVADP-UHFFFAOYSA-N 1-[[2-(8-azabicyclo[3.2.1]oct-3-en-3-yl)-4-chlorophenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C=1C(N2)CCC2CC=1C1=CC(Cl)=CC=C1CN(C1=CC=2)N=CC1=CC=2S(=O)(=O)NC1=NC=NS1 KXFJWALCQLVADP-UHFFFAOYSA-N 0.000 claims 1
- CRZNGZBFLFERPO-UHFFFAOYSA-N 1-[[2-(aminomethyl)phenyl]methyl]-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound NCC1=CC=CC=C1CN1C2=CC(F)=C(S(=O)(=O)NC=3N=C(F)C=CC=3)C=C2C=N1 CRZNGZBFLFERPO-UHFFFAOYSA-N 0.000 claims 1
- GJALFXKZEAXHHZ-OWOJBTEDSA-N 1-[[2-[(e)-3-aminoprop-1-enyl]-4-chlorophenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound NC\C=C\C1=CC(Cl)=CC=C1CN1C2=CC=C(S(=O)(=O)NC=3SN=CN=3)C=C2C=N1 GJALFXKZEAXHHZ-OWOJBTEDSA-N 0.000 claims 1
- XCWJYPNQTOFDRK-ZZXKWVIFSA-N 1-[[2-[(e)-3-aminoprop-1-enyl]phenyl]methyl]-6-fluoro-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound NC\C=C\C1=CC=CC=C1CN1C2=CC(F)=C(S(=O)(=O)NC=3SN=CN=3)C=C2C=N1 XCWJYPNQTOFDRK-ZZXKWVIFSA-N 0.000 claims 1
- VMTPZTDENTUFFJ-ZZXKWVIFSA-N 1-[[2-[(e)-3-aminoprop-1-enyl]phenyl]methyl]-7-chloro-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound NC\C=C\C1=CC=CC=C1CN1C2=C(Cl)C=C(S(=O)(=O)NC=3SN=CN=3)C=C2C=N1 VMTPZTDENTUFFJ-ZZXKWVIFSA-N 0.000 claims 1
- KENSZPCZGVMJIS-ZZXKWVIFSA-N 1-[[2-[(e)-3-aminoprop-1-enyl]phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound NC\C=C\C1=CC=CC=C1CN1C2=CC=C(S(=O)(=O)NC=3SN=CN=3)C=C2C=N1 KENSZPCZGVMJIS-ZZXKWVIFSA-N 0.000 claims 1
- WHACZBSIVGAAKF-UHFFFAOYSA-N 1-[[4-chloro-2-(1,2,3,4-tetrahydroisoquinolin-5-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C=1C=CC=2CNCCC=2C=1C1=CC(Cl)=CC=C1CN(C1=CC=2)N=CC1=CC=2S(=O)(=O)NC1=NC=NS1 WHACZBSIVGAAKF-UHFFFAOYSA-N 0.000 claims 1
- XIPAUKCVSFMVIT-UHFFFAOYSA-N 1-[[4-chloro-2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C=1CNCCC=1C1=CC(Cl)=CC=C1CN(C1=CC=2)N=CC1=CC=2S(=O)(=O)NC1=NC=NS1 XIPAUKCVSFMVIT-UHFFFAOYSA-N 0.000 claims 1
- BTZXXDLJFLQUAK-UHFFFAOYSA-N 1-[[4-chloro-2-(2,3,4,7-tetrahydro-1h-azepin-5-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C=1CNCCCC=1C1=CC(Cl)=CC=C1CN(C1=CC=2)N=CC1=CC=2S(=O)(=O)NC1=NC=NS1 BTZXXDLJFLQUAK-UHFFFAOYSA-N 0.000 claims 1
- UYVDFHJCAGJHRN-UHFFFAOYSA-N 1-benzyl-6-fluoro-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound N1=CC=2C=C(S(=O)(=O)NC=3SN=CN=3)C(F)=CC=2N1CC1=CC=CC=C1 UYVDFHJCAGJHRN-UHFFFAOYSA-N 0.000 claims 1
- VAYIKQOWHOXKNF-UHFFFAOYSA-N 1-benzyl-6-fluoro-n-(6-fluoropyridin-2-yl)indazole-5-sulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C(=CC=3N(CC=4C=CC=CC=4)N=CC=3C=2)F)=N1 VAYIKQOWHOXKNF-UHFFFAOYSA-N 0.000 claims 1
- GDYQWESMJPXUHN-UHFFFAOYSA-N 1-benzyl-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C=1C=C2N(CC=3C=CC=CC=3)N=CC2=CC=1S(=O)(=O)NC1=NC=NS1 GDYQWESMJPXUHN-UHFFFAOYSA-N 0.000 claims 1
- YFNMRKXDKJUPQG-UHFFFAOYSA-N 2-[(7-amino-5,6,7,8-tetrahydronaphthalen-1-yl)methyl]-n-(5-chloro-1,3-thiazol-2-yl)-6-fluoroindazole-5-sulfonamide Chemical compound C=12CC(N)CCC2=CC=CC=1CN(N=C1C=C2F)C=C1C=C2S(=O)(=O)NC1=NC=C(Cl)S1 YFNMRKXDKJUPQG-UHFFFAOYSA-N 0.000 claims 1
- MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 claims 1
- GKUPWDSSECKUDV-UHFFFAOYSA-N 6-fluoro-1-(1,2,3,4-tetrahydroisoquinolin-8-ylmethyl)-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound FC1=CC=2N(CC=3C=4CNCCC=4C=CC=3)N=CC=2C=C1S(=O)(=O)NC1=NC=NS1 GKUPWDSSECKUDV-UHFFFAOYSA-N 0.000 claims 1
- HNFYOOHRNWTYJO-UHFFFAOYSA-N 6-fluoro-1-(1,2,3,4-tetrahydroisoquinolin-8-ylmethyl)-n-(1,3-thiazol-2-yl)indazole-5-sulfonamide Chemical compound FC1=CC=2N(CC=3C=4CNCCC=4C=CC=3)N=CC=2C=C1S(=O)(=O)NC1=NC=CS1 HNFYOOHRNWTYJO-UHFFFAOYSA-N 0.000 claims 1
- ZQLOTXCADLUPOP-UHFFFAOYSA-N 6-fluoro-1-(1-phenylethyl)-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound N1=CC2=CC(S(=O)(=O)NC=3SN=CN=3)=C(F)C=C2N1C(C)C1=CC=CC=C1 ZQLOTXCADLUPOP-UHFFFAOYSA-N 0.000 claims 1
- RHZYYEZFTCJSBE-LBPRGKRZSA-N 6-fluoro-1-[(1s)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound FC=1C=C2N([C@H](C=3C=4CNCCC=4C=CC=3)C)N=CC2=CC=1S(=O)(=O)NC1=NC=NS1 RHZYYEZFTCJSBE-LBPRGKRZSA-N 0.000 claims 1
- ZQLOTXCADLUPOP-NSHDSACASA-N 6-fluoro-1-[(1s)-1-phenylethyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C1([C@H](C)N2C3=CC(F)=C(C=C3C=N2)S(=O)(=O)NC=2SN=CN=2)=CC=CC=C1 ZQLOTXCADLUPOP-NSHDSACASA-N 0.000 claims 1
- WDCFIOZXASZLCQ-UHFFFAOYSA-N 6-fluoro-1-[(2-iodophenyl)methyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound N1=CC=2C=C(S(=O)(=O)NC=3SN=CN=3)C(F)=CC=2N1CC1=CC=CC=C1I WDCFIOZXASZLCQ-UHFFFAOYSA-N 0.000 claims 1
- RHZYYEZFTCJSBE-UHFFFAOYSA-N 6-fluoro-1-[1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound C=1C=CC=2CCNCC=2C=1C(C)N(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=NC=NS1 RHZYYEZFTCJSBE-UHFFFAOYSA-N 0.000 claims 1
- YCZYLEYBYBXZRB-UHFFFAOYSA-N 6-fluoro-1-[1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]-n-(1,3-thiazol-2-yl)indazole-5-sulfonamide Chemical compound C=1C=CC=2CCNCC=2C=1C(C)N(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=NC=CS1 YCZYLEYBYBXZRB-UHFFFAOYSA-N 0.000 claims 1
- XUAWSGAUNROIKM-UHFFFAOYSA-N 6-fluoro-1-[[2-(1,2,3,4-tetrahydroisoquinolin-5-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)indazole-5-sulfonamide Chemical compound FC1=CC=2N(CC=3C(=CC=CC=3)C=3C=4CCNCC=4C=CC=3)N=CC=2C=C1S(=O)(=O)NC1=NC=NS1 XUAWSGAUNROIKM-UHFFFAOYSA-N 0.000 claims 1
- UOKKGTLPBFYZSU-UHFFFAOYSA-N 6-fluoro-1-[[2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]methyl]-n-(1,3-thiazol-2-yl)indazole-5-sulfonamide Chemical compound N1=CC=2C=C(S(=O)(=O)NC=3SC=CN=3)C(F)=CC=2N1CC1=CC=CC=C1C1=CCNCC1 UOKKGTLPBFYZSU-UHFFFAOYSA-N 0.000 claims 1
- QGLUAAQECRJFMK-UHFFFAOYSA-N 6-fluoro-n-(5-fluoropyridin-2-yl)-1-(1,2,3,4-tetrahydroisoquinolin-8-ylmethyl)indazole-5-sulfonamide Chemical compound N1=CC(F)=CC=C1NS(=O)(=O)C(C(=C1)F)=CC2=C1N(CC=1C=3CNCCC=3C=CC=1)N=C2 QGLUAAQECRJFMK-UHFFFAOYSA-N 0.000 claims 1
- MTXZEXIUQKVXSK-UHFFFAOYSA-N 6-fluoro-n-(5-fluoropyridin-2-yl)-1-[1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]indazole-5-sulfonamide Chemical compound C=1C=CC=2CCNCC=2C=1C(C)N(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=CC=C(F)C=N1 MTXZEXIUQKVXSK-UHFFFAOYSA-N 0.000 claims 1
- ZVLCBMOKPBYNBF-UHFFFAOYSA-N 6-fluoro-n-(6-fluoropyridin-2-yl)-1-(1,2,3,4-tetrahydroisoquinolin-8-ylmethyl)indazole-5-sulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C(=CC=3N(CC=4C=5CNCCC=5C=CC=4)N=CC=3C=2)F)=N1 ZVLCBMOKPBYNBF-UHFFFAOYSA-N 0.000 claims 1
- UBGLVEIJGVQXPA-UHFFFAOYSA-N 6-fluoro-n-(6-fluoropyridin-2-yl)-1-[(2-iodophenyl)methyl]indazole-5-sulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C(=CC=3N(CC=4C(=CC=CC=4)I)N=CC=3C=2)F)=N1 UBGLVEIJGVQXPA-UHFFFAOYSA-N 0.000 claims 1
- HDHCVZZLHLWFAG-UHFFFAOYSA-N 6-fluoro-n-(6-fluoropyridin-2-yl)-1-[(4-fluoro-1,2,3,4-tetrahydroisoquinolin-8-yl)methyl]indazole-5-sulfonamide Chemical compound C1=CC=C2C(F)CNCC2=C1CN(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=CC=CC(F)=N1 HDHCVZZLHLWFAG-UHFFFAOYSA-N 0.000 claims 1
- BDXVDLWUWAYQKL-UHFFFAOYSA-N 6-fluoro-n-(6-fluoropyridin-2-yl)-1-[1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]indazole-5-sulfonamide Chemical compound C=1C=CC=2CCNCC=2C=1C(C)N(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=CC=CC(F)=N1 BDXVDLWUWAYQKL-UHFFFAOYSA-N 0.000 claims 1
- QMJIVIHONRHYGL-UHFFFAOYSA-N 6-fluoro-n-(6-fluoropyridin-2-yl)-1-[1-(2-piperidin-4-ylphenyl)ethyl]indazole-5-sulfonamide Chemical compound N1=CC2=CC(S(=O)(=O)NC=3N=C(F)C=CC=3)=C(F)C=C2N1C(C)C1=CC=CC=C1C1CCNCC1 QMJIVIHONRHYGL-UHFFFAOYSA-N 0.000 claims 1
- SRBXSJAKGQJETP-UHFFFAOYSA-N 6-fluoro-n-(6-fluoropyridin-2-yl)-1-[1-[2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]ethyl]indazole-5-sulfonamide Chemical compound N1=CC2=CC(S(=O)(=O)NC=3N=C(F)C=CC=3)=C(F)C=C2N1C(C)C1=CC=CC=C1C1=CCNCC1 SRBXSJAKGQJETP-UHFFFAOYSA-N 0.000 claims 1
- UFTKNJOJYUBCRR-UHFFFAOYSA-N 6-fluoro-n-(6-fluoropyridin-2-yl)-1-[[2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]methyl]indazole-5-sulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C(=CC=3N(CC=4C(=CC=CC=4)C=4CCNCC=4)N=CC=3C=2)F)=N1 UFTKNJOJYUBCRR-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 150000005840 aryl radicals Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- OJFGKCLKLHOZNY-UHFFFAOYSA-N n-(5-chloro-1,3-thiazol-2-yl)-6-fluoro-1-(1,2,3,4-tetrahydroisoquinolin-8-ylmethyl)indazole-5-sulfonamide Chemical compound FC1=CC=2N(CC=3C=4CNCCC=4C=CC=3)N=CC=2C=C1S(=O)(=O)NC1=NC=C(Cl)S1 OJFGKCLKLHOZNY-UHFFFAOYSA-N 0.000 claims 1
- KVCFFRVMHFWXRQ-UHFFFAOYSA-N n-(5-chloro-1,3-thiazol-2-yl)-6-fluoro-1-[1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]indazole-5-sulfonamide Chemical compound C=1C=CC=2CCNCC=2C=1C(C)N(C1=CC=2F)N=CC1=CC=2S(=O)(=O)NC1=NC=C(Cl)S1 KVCFFRVMHFWXRQ-UHFFFAOYSA-N 0.000 claims 1
- JXVAEAWLORTHQW-UHFFFAOYSA-N n-(5-chloro-1,3-thiazol-2-yl)-6-fluoro-2-[1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]indazole-5-sulfonamide Chemical compound C=1C=CC=2CCNCC=2C=1C(C)N(N=C1C=C2F)C=C1C=C2S(=O)(=O)NC1=NC=C(Cl)S1 JXVAEAWLORTHQW-UHFFFAOYSA-N 0.000 claims 1
- CSCJDGKSKWJIBP-UHFFFAOYSA-N n-(6-fluoropyridin-2-yl)-6-methyl-1-[1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]indazole-5-sulfonamide Chemical compound C=1C=CC=2CCNCC=2C=1C(C)N(C1=CC=2C)N=CC1=CC=2S(=O)(=O)NC1=CC=CC(F)=N1 CSCJDGKSKWJIBP-UHFFFAOYSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epidemiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261719118P | 2012-10-26 | 2012-10-26 | |
| US61/719,118 | 2012-10-26 | ||
| PCT/US2013/066360 WO2014066491A1 (en) | 2012-10-26 | 2013-10-23 | N-substituted indazole sulfonamide compounds with selective activity in voltage-gated sodium channels |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2015119640A true RU2015119640A (ru) | 2016-12-20 |
Family
ID=50545213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015119640A RU2015119640A (ru) | 2012-10-26 | 2013-10-23 | Соединения n-замещенного индазол-сульфонамида с избирательной активностью в потенциал-зависимых натриевых каналах |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9388179B2 (enExample) |
| EP (1) | EP2911663B1 (enExample) |
| JP (1) | JP2015535252A (enExample) |
| KR (1) | KR20150074123A (enExample) |
| CN (1) | CN104869992A (enExample) |
| AU (1) | AU2013334664A1 (enExample) |
| BR (1) | BR112015008987A2 (enExample) |
| CA (1) | CA2891056A1 (enExample) |
| RU (1) | RU2015119640A (enExample) |
| WO (1) | WO2014066491A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6014155B2 (ja) | 2011-10-31 | 2016-10-25 | ゼノン・ファーマシューティカルズ・インコーポレイテッドＸｅｎｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | ビアリールエーテルスルホンアミドおよび治療剤としてのそれらの使用 |
| ES2586213T3 (es) | 2011-10-31 | 2016-10-13 | Xenon Pharmaceuticals Inc. | Compuestos de bencenosulfonamida y su uso como agentes terapéuticos |
| BR112014029161A2 (pt) | 2012-05-22 | 2017-06-27 | Genentech Inc | benzamidas n-substituídas e seu uso no tratamento de dor |
| BR112015000187A2 (pt) | 2012-07-06 | 2017-06-27 | Genentech Inc | benzamidas substituídas com n e métodos de uso das mesmas |
| BR112015022488A2 (pt) | 2013-03-14 | 2017-07-18 | Genentech Inc | triazolopiridinas substituídas e métodos de uso das mesmas |
| BR112015023397A2 (pt) | 2013-03-15 | 2017-07-18 | Genentech Inc | benzoxazois substituídos e métodos de uso dos mesmos |
| CR20160296A (es) | 2013-11-27 | 2016-09-20 | Genentech Inc | Benzamidas sustituidas y métodos para usarlas |
| EP3166939B1 (en) | 2014-07-07 | 2019-06-05 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| US9783527B2 (en) * | 2014-09-16 | 2017-10-10 | Abbvie Inc. | Indazole ureas and method of use |
| US9682985B2 (en) * | 2015-03-13 | 2017-06-20 | Abbvie Inc. | (Indazol-4-yl) hexahydropyrrolopyrrolones and methods of use |
| WO2016191312A1 (en) | 2015-05-22 | 2016-12-01 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| MA42683A (fr) | 2015-08-27 | 2018-07-04 | Genentech Inc | Composés thérapeutiques et leurs méthodes utilisation |
| PE20181003A1 (es) | 2015-09-28 | 2018-06-26 | Genentech Inc | Compuestos terapeuticos y sus metodos de uso |
| CN108495851A (zh) | 2015-11-25 | 2018-09-04 | 基因泰克公司 | 取代的苯甲酰胺及其使用方法 |
| TW201726637A (zh) | 2015-12-18 | 2017-08-01 | 默沙東藥廠 | 對電位閘控鈉通道具選擇活性之羥基烷基胺－及羥基環烷基胺－取代之二胺－芳基磺胺化合物 |
| EP3854782A1 (en) | 2016-03-30 | 2021-07-28 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| KR102366077B1 (ko) | 2016-05-20 | 2022-02-21 | 제논 파마슈티칼스 인크. | 벤젠술폰아미드 화합물 및 치료제로서의 그의 용도 |
| SG11201903348UA (en) | 2016-10-17 | 2019-05-30 | Genentech Inc | Therapeutic compounds and methods of use thereof |
| KR20190086772A (ko) | 2016-12-09 | 2019-07-23 | 제논 파마슈티칼스 인크. | 벤젠술폰아미드 화합물 및 치료제로서의 그의 용도 |
| WO2018175707A1 (en) | 2017-03-24 | 2018-09-27 | Genentech, Inc. | 4-piperidin-n-(pyrimidin-4-yl)chroman-7-sulfonamide derivatives as sodium channel inhibitors |
| CN107247885B (zh) * | 2017-07-06 | 2020-07-03 | 中国水产科学研究院黄海水产研究所 | 一种电压-门控钠离子通道的结构预测方法 |
| EP3759098A1 (en) | 2018-02-26 | 2021-01-06 | Genentech, Inc. | Pyridine-sulfonamide compounds and their use against pain and related conditions |
| EP3774801A1 (en) | 2018-03-30 | 2021-02-17 | F. Hoffmann-La Roche AG | Fused ring hydro-pyrido compounds as sodium channel inhibitors |
| TW202003490A (zh) | 2018-05-22 | 2020-01-16 | 瑞士商赫孚孟拉羅股份公司 | 治療性化合物及其使用方法 |
| BR112020024729A2 (pt) | 2018-06-13 | 2021-03-23 | Xenon Pharmaceuticals, Inc. | compostos de benzenossulfonamida e seu uso como agentes terapêuticos |
| CA3104913A1 (en) | 2018-08-31 | 2020-03-05 | Xenon Pharmaceuticals Inc. | Heteroaryl-substituted sulfonamide compounds and their use as sodium channel inhibitors |
| IL279810B2 (en) | 2018-08-31 | 2025-03-01 | Xenon Pharmaceuticals Inc | Heteroaryl-modified sulfonamide compounds and their use as medicinal agents |
| WO2020192553A1 (zh) * | 2019-03-22 | 2020-10-01 | 上海海雁医药科技有限公司 | 磺酰基取代的苯并杂环甲酰胺衍生物、其制法与医药上的用途 |
| AU2020392128A1 (en) | 2019-11-27 | 2022-06-09 | Praxis Precision Medicines, Inc. | Formulations of ion channel modulators and methods of preparation and use of ion channel modulators |
| KR20240159579A (ko) | 2022-02-14 | 2024-11-05 | 어레이즈 테라퓨틱스 인크. | Parg 억제제 |
| WO2023186058A1 (zh) * | 2022-03-31 | 2023-10-05 | 江苏恒瑞医药股份有限公司 | 吲唑类化合物、其制备方法及其在医药上的应用 |
| CA3250706A1 (en) | 2022-04-26 | 2023-11-02 | Praxis Precision Medicines, Inc. | TREATMENT OF NEUROLOGICAL DISORDERS |
| WO2024173234A1 (en) * | 2023-02-13 | 2024-08-22 | Arase Therapeutics Inc. | Inhibitors of parg |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3705185A (en) | 1969-04-14 | 1972-12-05 | Minnesota Mining & Mfg | N-aroyl sulfonamides |
| US4136256A (en) | 1977-09-27 | 1979-01-23 | American Cyanamid Company | 4-(monoalkylamino)benzoic acid imidates |
| US4242273A (en) | 1977-09-27 | 1980-12-30 | American Cyanamid Company | 4-(Monoalkylamino)benzoic acid amides and imidates |
| US4309553A (en) | 1977-09-27 | 1982-01-05 | American Cyanamid Company | Aldehydes and ketones containing a 4-(monoalkylamino)-benzoyl substituent |
| US4254138A (en) | 1977-12-19 | 1981-03-03 | American Cyanamid Company | Esters of 4-(monoalkylamino)benzoic hydroxyalkanoic acids |
| US4272546A (en) | 1977-12-19 | 1981-06-09 | American Cyanamid Company | Esters of 4-(monoalkylamino)benzoic hydroxyalkanoic acids |
| US4245097A (en) | 1978-02-27 | 1981-01-13 | American Cyanamid Company | 4-[(Monosubstituted-alkyl) amino] benzoic acids and analogs as hypolipidemic and antiatherosclerotic agents |
| US4227014A (en) | 1978-02-27 | 1980-10-07 | American Cyanamid Company | 4-[(Cycloalkyl or cycloalkenyl substituted)amino, alkylamino or alkenylamino]benzoic acids and salts thereof |
| US4243609A (en) | 1978-02-02 | 1981-01-06 | American Cyanamid Company | Ring-fluorinated 4-(hexadecyl-amino) N-substituted benzamide compounds |
| US4230628A (en) | 1978-04-12 | 1980-10-28 | American Cyanamid Company | 4-[(Carboxyl- and sulfamyl-substituted alkyl)-amino] benzoic acids and analogs |
| US4211783A (en) | 1978-03-20 | 1980-07-08 | American Cyanamid Company | Hypolipidemic and antiatherosclerotic novel 4-(aralkyl- and heteroarylalkylamino)phenyl compounds |
| US4205085A (en) | 1978-03-09 | 1980-05-27 | American Cyanamid Company | Hypolipidemic and antiatherosclerotic 4-(polyfluoroalkylamino)phenyl compounds |
| US4230878A (en) | 1978-03-08 | 1980-10-28 | American Cyanamid Company | Hypolipidemic and antiatherosclerotic 4-[(cyclopropyl alkyl)amino]benzoic acids and derivatives |
| US4305959A (en) | 1978-03-09 | 1981-12-15 | American Cyanamid Company | Hypolipidemic and antiatherosclerotic 4-(polyfluoro-alkylamino)phenyl compounds |
| US4310545A (en) | 1978-03-09 | 1982-01-12 | American Cyanamid Company | Hypolipidemic and antiatherosclerotic 4-(polyfluoroalkylamino) phenyl compounds |
| US4318914A (en) | 1978-03-09 | 1982-03-09 | American Cyanamid Company | Hypolipidemic and antiatherosclerotic 4-(polyfluoro-alkylamino)phenyl compounds |
| US4485105A (en) | 1978-10-12 | 1984-11-27 | American Cyanamid Company | Method of treating hyperlipidemia with 4-(monoalkylamino)benzoic acid amides |
| DK471479A (da) | 1978-12-13 | 1980-06-14 | Pfizer | Fremgangsmaade til fremstilling af imidazolderivater og salte deraf |
| US4670421A (en) | 1982-07-12 | 1987-06-02 | American Cyanamid Company | Antiatherosclerotic silanes |
| JP4316787B2 (ja) | 2000-01-11 | 2009-08-19 | 壽製薬株式会社 | エーテル又はアミド誘導体、その製法並びにそれを含有する糖尿病治療剤、 |
| SE0402762D0 (sv) * | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Indazole sulphonamide derivatives |
| US7786137B2 (en) * | 2005-05-10 | 2010-08-31 | Vertex Pharmaceuticals Incorporated | Bicyclic derivatives as modulators of ion channels |
| EP2173743A2 (en) * | 2007-07-13 | 2010-04-14 | Icagen, Inc. | Sodium channel inhibitors |
| AU2009307892A1 (en) * | 2008-10-23 | 2010-04-29 | Merck Sharp & Dohme Corp. | Fused heterocyclic M1 receptor positive allosteric modulators |
| HUE025013T2 (hu) | 2009-01-12 | 2016-04-28 | Pfizer Ltd | Szulfonamid-származékok |
| CA2804593C (en) | 2010-07-09 | 2015-11-24 | Pfizer Limited | Biphenyloxybenzensulphonamide derivatives useful as sodium channel inhibitors |
| JP5860045B2 (ja) | 2010-07-09 | 2016-02-16 | ファイザー・リミテッドＰｆｉｚｅｒ Ｌｉｍｉｔｅｄ | 化合物 |
| JP5872552B2 (ja) | 2010-07-09 | 2016-03-01 | ファイザー・リミテッドＰｆｉｚｅｒ Ｌｉｍｉｔｅｄ | 化学化合物 |
| JP2013531030A (ja) | 2010-07-12 | 2013-08-01 | ファイザー・リミテッド | 電位開口型ナトリウムチャネルの阻害剤としてのｎ−スルホニルベンズアミド |
| WO2012007883A1 (en) | 2010-07-12 | 2012-01-19 | Pfizer Limited | Sulfonamide derivatives as nav1.7 inhibitors for the treatment of pain |
| ES2526541T3 (es) | 2010-07-12 | 2015-01-13 | Pfizer Limited | N-sulfonilbenzamidas como inhibidores de canales de sodio dependientes de voltaje |
| CA2804716A1 (en) | 2010-07-12 | 2012-01-19 | Pfizer Limited | Chemical compounds |
| US9514344B2 (en) | 2010-11-10 | 2016-12-06 | Datalogic ADC, Inc. | Adaptive data reader and method of operating |
| WO2012095781A1 (en) * | 2011-01-13 | 2012-07-19 | Pfizer Limited | Indazole derivatives as sodium channel inhibitors |
| AU2012296529A1 (en) | 2011-08-17 | 2014-02-20 | Amgen Inc. | Heteroaryl sodium channel inhibitors |
| JP6014155B2 (ja) | 2011-10-31 | 2016-10-25 | ゼノン・ファーマシューティカルズ・インコーポレイテッドＸｅｎｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | ビアリールエーテルスルホンアミドおよび治療剤としてのそれらの使用 |
| ES2586213T3 (es) | 2011-10-31 | 2016-10-13 | Xenon Pharmaceuticals Inc. | Compuestos de bencenosulfonamida y su uso como agentes terapéuticos |
| EP2788332A1 (en) | 2011-12-07 | 2014-10-15 | Amgen, Inc. | Bicyclic aryl and heteroaryl sodium channel inhibitors |
| WO2013134518A1 (en) | 2012-03-09 | 2013-09-12 | Amgen Inc. | Sulfamide sodium channel inhibitors |
-
2013
- 2013-10-23 US US14/437,142 patent/US9388179B2/en active Active
- 2013-10-23 AU AU2013334664A patent/AU2013334664A1/en not_active Abandoned
- 2013-10-23 JP JP2015539755A patent/JP2015535252A/ja active Pending
- 2013-10-23 KR KR1020157013297A patent/KR20150074123A/ko not_active Withdrawn
- 2013-10-23 EP EP13849733.4A patent/EP2911663B1/en active Active
- 2013-10-23 BR BR112015008987A patent/BR112015008987A2/pt not_active IP Right Cessation
- 2013-10-23 CA CA2891056A patent/CA2891056A1/en not_active Abandoned
- 2013-10-23 CN CN201380068064.9A patent/CN104869992A/zh active Pending
- 2013-10-23 RU RU2015119640A patent/RU2015119640A/ru not_active Application Discontinuation
- 2013-10-23 WO PCT/US2013/066360 patent/WO2014066491A1/en not_active Ceased
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| US20150284389A1 (en) | 2015-10-08 |
| EP2911663A4 (en) | 2016-04-13 |
| AU2013334664A1 (en) | 2015-05-07 |
| CA2891056A1 (en) | 2014-05-01 |
| KR20150074123A (ko) | 2015-07-01 |
| CN104869992A (zh) | 2015-08-26 |
| BR112015008987A2 (pt) | 2017-07-04 |
| US9388179B2 (en) | 2016-07-12 |
| EP2911663A1 (en) | 2015-09-02 |
| JP2015535252A (ja) | 2015-12-10 |
| WO2014066491A1 (en) | 2014-05-01 |
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