RU2017125520A - Соединения, ингибирующие parg - Google Patents
Соединения, ингибирующие parg Download PDFInfo
- Publication number
- RU2017125520A RU2017125520A RU2017125520A RU2017125520A RU2017125520A RU 2017125520 A RU2017125520 A RU 2017125520A RU 2017125520 A RU2017125520 A RU 2017125520A RU 2017125520 A RU2017125520 A RU 2017125520A RU 2017125520 A RU2017125520 A RU 2017125520A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- sulfonamide
- methylcyclopropyl
- oxobenzimidazole
- thiadiazol
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 27
- 101000589450 Homo sapiens Poly(ADP-ribose) glycohydrolase Proteins 0.000 title 1
- 102100032347 Poly(ADP-ribose) glycohydrolase Human genes 0.000 title 1
- 230000002401 inhibitory effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 92
- 229910052739 hydrogen Inorganic materials 0.000 claims 47
- 239000001257 hydrogen Substances 0.000 claims 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 33
- -1 cyano, formyl Chemical group 0.000 claims 33
- 229910052736 halogen Inorganic materials 0.000 claims 25
- 150000002367 halogens Chemical class 0.000 claims 25
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 21
- 125000001424 substituent group Chemical group 0.000 claims 20
- 125000002947 alkylene group Chemical group 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 125000001188 haloalkyl group Chemical group 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000004463 2,4-dimethyl-thiazol-5-yl group Chemical group CC=1SC(=C(N1)C)* 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 125000004450 alkenylene group Chemical group 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- MPCMGTGCBAROLL-ZZXKWVIFSA-N (E)-3-[2-[3-methyl-6-[(1-methylcyclopropyl)sulfamoyl]-2-oxobenzimidazol-1-yl]-1,3-thiazol-5-yl]prop-2-enoic acid Chemical compound CN1C(N(C2=C1C=CC(=C2)S(NC1(CC1)C)(=O)=O)C=1SC(=CN=1)/C=C/C(=O)O)=O MPCMGTGCBAROLL-ZZXKWVIFSA-N 0.000 claims 1
- IAMYTGVZQBTOJC-XBXARRHUSA-N (E)-3-[5-[3-methyl-6-[(1-methylcyclopropyl)sulfamoyl]-2-oxobenzimidazol-1-yl]furan-2-yl]prop-2-enoic acid Chemical compound CN1C(N(C2=C1C=CC(=C2)S(NC1(CC1)C)(=O)=O)C1=CC=C(O1)/C=C/C(=O)O)=O IAMYTGVZQBTOJC-XBXARRHUSA-N 0.000 claims 1
- XLJFAVNFUCDTBQ-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC(CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O)(C)C XLJFAVNFUCDTBQ-UHFFFAOYSA-N 0.000 claims 1
- CIWCPXDSWUUBFT-UHFFFAOYSA-N 1-(2-cyclopropylethyl)-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C1(CC1)CCN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O CIWCPXDSWUUBFT-UHFFFAOYSA-N 0.000 claims 1
- ZEQILPMXZFNEOK-UHFFFAOYSA-N 1-(2-fluoroethyl)-N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound FCCN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1OC(=NN=1)C)=O ZEQILPMXZFNEOK-UHFFFAOYSA-N 0.000 claims 1
- SMVGNCJSRNMVJB-UHFFFAOYSA-N 1-(2-methoxyethyl)-N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound COCCN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1OC(=NN=1)C)=O SMVGNCJSRNMVJB-UHFFFAOYSA-N 0.000 claims 1
- BCCJJESGODHLFA-UHFFFAOYSA-N 1-(2-methoxyethyl)-N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound COCCN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1SC(=NN=1)C)=O BCCJJESGODHLFA-UHFFFAOYSA-N 0.000 claims 1
- NZZZAURNHJNCTC-UHFFFAOYSA-N 1-(3-methoxypropyl)-N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound COCCCN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1OC(=NN=1)C)=O NZZZAURNHJNCTC-UHFFFAOYSA-N 0.000 claims 1
- IIGILOUNMKXAJJ-UHFFFAOYSA-N 1-(3-methoxypropyl)-N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound COCCCN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1SC(=NN=1)C)=O IIGILOUNMKXAJJ-UHFFFAOYSA-N 0.000 claims 1
- XDOQHRJLRJJRFN-UHFFFAOYSA-N 1-(cyanomethyl)-3-[5-(difluoromethyl)-1,3,4-thiadiazol-2-yl]-6-fluoro-N-[1-(fluoromethyl)cyclopropyl]-2-oxobenzimidazole-5-sulfonamide Chemical compound C(#N)CN1C(N(C2=C1C=C(C(=C2)S(=O)(=O)NC1(CC1)CF)F)C=1SC(=NN=1)C(F)F)=O XDOQHRJLRJJRFN-UHFFFAOYSA-N 0.000 claims 1
- XOUISIUVSMHYLB-UHFFFAOYSA-N 1-(cyanomethyl)-N-(1-methylcyclopropyl)-3-(3-methyl-1,2,4-thiadiazol-5-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C(#N)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C1=NC(=NS1)C)=O XOUISIUVSMHYLB-UHFFFAOYSA-N 0.000 claims 1
- BTHSNRAVCATRRD-UHFFFAOYSA-N 1-(cyanomethyl)-N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C(#N)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1SC(=NN=1)C)=O BTHSNRAVCATRRD-UHFFFAOYSA-N 0.000 claims 1
- WTVZKFJVKPZEBJ-UHFFFAOYSA-N 1-(cyanomethyl)-N-[1-(fluoromethyl)cyclopropyl]-3-(3-methyl-1,2,4-thiadiazol-5-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C(#N)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)CF)C1=NC(=NS1)C)=O WTVZKFJVKPZEBJ-UHFFFAOYSA-N 0.000 claims 1
- AQOFECLBMSDMKY-UHFFFAOYSA-N 1-(cyanomethyl)-N-[1-(fluoromethyl)cyclopropyl]-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C(#N)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)CF)C=1SC(=NN=1)C)=O AQOFECLBMSDMKY-UHFFFAOYSA-N 0.000 claims 1
- GYSZIRLTAVKHDV-UHFFFAOYSA-N 1-(cyclobutylmethyl)-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C1(CCC1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O GYSZIRLTAVKHDV-UHFFFAOYSA-N 0.000 claims 1
- LCLFNLLSENLMOG-UHFFFAOYSA-N 1-(cyclohexylmethyl)-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C1(CCCCC1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O LCLFNLLSENLMOG-UHFFFAOYSA-N 0.000 claims 1
- CHRLWLJHTKZWQG-UHFFFAOYSA-N 1-(cyclopentylmethyl)-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C1(CCCC1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O CHRLWLJHTKZWQG-UHFFFAOYSA-N 0.000 claims 1
- QQRHOJQCOMIPFU-UHFFFAOYSA-N 1-(cyclopropylmethyl)-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C1(CC1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O QQRHOJQCOMIPFU-UHFFFAOYSA-N 0.000 claims 1
- LKKQAONUZQGQFS-UHFFFAOYSA-N 1-(cyclopropylmethyl)-N-(1-methylcyclopropyl)-2-oxo-3-phenylbenzimidazole-5-sulfonamide Chemical compound C1(CC1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C1=CC=CC=C1)=O LKKQAONUZQGQFS-UHFFFAOYSA-N 0.000 claims 1
- ASRAPKGFINDMMP-UHFFFAOYSA-N 1-(cyclopropylmethyl)-N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C1(CC1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1SC(=NN=1)C)=O ASRAPKGFINDMMP-UHFFFAOYSA-N 0.000 claims 1
- ZUQCQBRBHVLGLM-UHFFFAOYSA-N 1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound FC1(C(C1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O)F ZUQCQBRBHVLGLM-UHFFFAOYSA-N 0.000 claims 1
- RLOLWRLTMXBUMK-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-3-(1H-imidazol-5-yl)-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C1=CN=CN1)=O RLOLWRLTMXBUMK-UHFFFAOYSA-N 0.000 claims 1
- BMRPAMCVDSSOKT-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-3-(3-methoxy-1,2,4-thiadiazol-5-yl)-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C1=NC(=NS1)OC)=O BMRPAMCVDSSOKT-UHFFFAOYSA-N 0.000 claims 1
- QDCZQKZIBKDUHZ-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-N-(1-methylcyclopropyl)-2-oxo-3-(1,2-thiazol-4-yl)benzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1C=NSC=1)=O QDCZQKZIBKDUHZ-UHFFFAOYSA-N 0.000 claims 1
- IJFOAPQROLZTGR-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-N-(1-methylcyclopropyl)-2-oxo-3-(1,3-thiazol-2-yl)benzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1SC=CN=1)=O IJFOAPQROLZTGR-UHFFFAOYSA-N 0.000 claims 1
- FXEWVHWLPURWNO-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-N-(1-methylcyclopropyl)-2-oxo-3-(1,3-thiazol-4-yl)benzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1N=CSC=1)=O FXEWVHWLPURWNO-UHFFFAOYSA-N 0.000 claims 1
- GEWAZELVQYACPS-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-N-(1-methylcyclopropyl)-2-oxo-3-(1,3-thiazol-5-yl)benzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C1=CN=CS1)=O GEWAZELVQYACPS-UHFFFAOYSA-N 0.000 claims 1
- JNCJLWUKARCFAB-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-N-(1-methylcyclopropyl)-2-oxo-3-pyridazin-3-ylbenzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1N=NC=CC=1)=O JNCJLWUKARCFAB-UHFFFAOYSA-N 0.000 claims 1
- UVHSGGGECVTWDY-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-N-(1-methylcyclopropyl)-2-oxo-3H-benzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(NC2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)=O UVHSGGGECVTWDY-UHFFFAOYSA-N 0.000 claims 1
- XJOFFLWJIGAMPP-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-N-(1-methylcyclopropyl)-3-(1-methylpyrazol-3-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C1=NN(C=C1)C)=O XJOFFLWJIGAMPP-UHFFFAOYSA-N 0.000 claims 1
- KPMMORMQMMMZDC-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-N-(1-methylcyclopropyl)-3-(4-methyl-1,3-thiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1SC=C(N=1)C)=O KPMMORMQMMMZDC-UHFFFAOYSA-N 0.000 claims 1
- ALPPCHUXOIANDU-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1OC(=NN=1)C)=O ALPPCHUXOIANDU-UHFFFAOYSA-N 0.000 claims 1
- HQQQUVLNPWIIFG-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1SC(=NN=1)C)=O HQQQUVLNPWIIFG-UHFFFAOYSA-N 0.000 claims 1
- LPADAGRRQSUJCZ-UHFFFAOYSA-N 1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-N-(1-methylcyclopropyl)-3-(5-methyl-1,3-thiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1SC(=CN=1)C)=O LPADAGRRQSUJCZ-UHFFFAOYSA-N 0.000 claims 1
- YFWIHNREIPOEPB-UHFFFAOYSA-N 1-[(2,5-dimethylpyrazol-3-yl)methyl]-N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CN1N=C(C=C1CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C=1SC(=NN=1)C)=O)C YFWIHNREIPOEPB-UHFFFAOYSA-N 0.000 claims 1
- UYURXLQKMPOQHH-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound ClC1=C(C(=CC=C1)Cl)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O UYURXLQKMPOQHH-UHFFFAOYSA-N 0.000 claims 1
- PODGHNOPOMVDMZ-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound FC1=C(C(=CC=C1)F)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O PODGHNOPOMVDMZ-UHFFFAOYSA-N 0.000 claims 1
- RGXISRBOTKJHEG-UHFFFAOYSA-N 1-[(2-cyanophenyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C(#N)C1=C(C=CC=C1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O RGXISRBOTKJHEG-UHFFFAOYSA-N 0.000 claims 1
- RKMNJASSARZSOH-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound FC1=C(C=CC=C1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O RKMNJASSARZSOH-UHFFFAOYSA-N 0.000 claims 1
- PZRBCUGXZAPXRW-UHFFFAOYSA-N 1-[(2-methoxyphenyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound COC1=C(C=CC=C1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O PZRBCUGXZAPXRW-UHFFFAOYSA-N 0.000 claims 1
- UCCCXAOGQXANMY-UHFFFAOYSA-N 1-[(3,5-dichlorophenyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound ClC=1C=C(C=C(C=1)Cl)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O UCCCXAOGQXANMY-UHFFFAOYSA-N 0.000 claims 1
- NYDOJHJHIFWOQJ-UHFFFAOYSA-N 1-[(3,5-difluorophenyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound FC=1C=C(C=C(C=1)F)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O NYDOJHJHIFWOQJ-UHFFFAOYSA-N 0.000 claims 1
- WOFJNSUEQRDKSA-UHFFFAOYSA-N 1-[(3,5-dimethoxyphenyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound COC=1C=C(C=C(C=1)OC)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O WOFJNSUEQRDKSA-UHFFFAOYSA-N 0.000 claims 1
- OACQRWADBBXDIX-UHFFFAOYSA-N 1-[(3,5-dimethylphenyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC=1C=C(C=C(C=1)C)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O OACQRWADBBXDIX-UHFFFAOYSA-N 0.000 claims 1
- XRTFPYURHCEABJ-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound ClC=1C=C(C=CC=1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O XRTFPYURHCEABJ-UHFFFAOYSA-N 0.000 claims 1
- SSSRGZQTBVGCRX-UHFFFAOYSA-N 1-[(3-cyanophenyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C(#N)C=1C=C(C=CC=1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O SSSRGZQTBVGCRX-UHFFFAOYSA-N 0.000 claims 1
- WNXVOYHGKKHVSE-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-3-methyl-N-(1-methylcyclopropyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound FC=1C=C(C=CC=1)CN1C(N(C2=C1C=CC(=C2)S(=O)(=O)NC1(CC1)C)C)=O WNXVOYHGKKHVSE-UHFFFAOYSA-N 0.000 claims 1
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- VXRURNBHUIRHAR-UHFFFAOYSA-N N,N-dimethyl-3-[2-[3-methyl-6-[(1-methylcyclopropyl)sulfamoyl]-2-oxobenzimidazol-1-yl]-1,3-thiazol-5-yl]propanamide Chemical compound CN(C(CCC1=CN=C(S1)N1C(N(C2=C1C=C(C=C2)S(NC1(CC1)C)(=O)=O)C)=O)=O)C VXRURNBHUIRHAR-UHFFFAOYSA-N 0.000 claims 1
- DOIHFCAUGYGIEG-UHFFFAOYSA-N N-(1-cyanocyclopropyl)-1-(2-methoxyethyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C(#N)C1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CCOC)C=C1 DOIHFCAUGYGIEG-UHFFFAOYSA-N 0.000 claims 1
- GVWQHRBODYWFKR-UHFFFAOYSA-N N-(1-cyanocyclopropyl)-1-ethyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C(#N)C1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CC)C=C1 GVWQHRBODYWFKR-UHFFFAOYSA-N 0.000 claims 1
- CIQXKJHISQJHDX-UHFFFAOYSA-N N-(1-cyanocyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxo-1H-benzimidazole-5-sulfonamide Chemical compound C(#N)C1(CC1)NS(=O)(=O)C1=CC2=C(NC(N2C=2SC(=NN=2)C)=O)C=C1 CIQXKJHISQJHDX-UHFFFAOYSA-N 0.000 claims 1
- VPSLCGKYMAZOIT-UHFFFAOYSA-N N-(1-cyanocyclopropyl)-3-[5-(difluoromethyl)-1,3,4-thiadiazol-2-yl]-1-(2-methoxyethyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound C(#N)C1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C(F)F)=O)CCOC)C=C1 VPSLCGKYMAZOIT-UHFFFAOYSA-N 0.000 claims 1
- VIFRPFCMSYGVRL-UHFFFAOYSA-N N-(1-cyanocyclopropyl)-3-[5-(difluoromethyl)-1,3,4-thiadiazol-2-yl]-1-[(2,5-dimethylpyrazol-3-yl)methyl]-2-oxobenzimidazole-5-sulfonamide Chemical compound C(#N)C1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C(F)F)=O)CC=2N(N=C(C=2)C)C)C=C1 VIFRPFCMSYGVRL-UHFFFAOYSA-N 0.000 claims 1
- FGEIAHKKAUQFQT-UHFFFAOYSA-N N-(1-methylcyclopropyl)-1-[(1-methylpiperidin-2-yl)methyl]-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CC2N(CCCC2)C)C=C1 FGEIAHKKAUQFQT-UHFFFAOYSA-N 0.000 claims 1
- GCOSCTMAWSAEKB-UHFFFAOYSA-N N-(1-methylcyclopropyl)-1-[(1-methylpiperidin-3-yl)methyl]-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CC2CN(CCC2)C)C=C1 GCOSCTMAWSAEKB-UHFFFAOYSA-N 0.000 claims 1
- MMSCXAVIDZGRLE-UHFFFAOYSA-N N-(1-methylcyclopropyl)-1-[(1-methylpyrrolidin-2-yl)methyl]-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CC2N(CCC2)C)C=C1 MMSCXAVIDZGRLE-UHFFFAOYSA-N 0.000 claims 1
- ZKPKTZCTFLSGPY-UHFFFAOYSA-N N-(1-methylcyclopropyl)-1-[(5-methylfuran-2-yl)methyl]-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CC=2OC(=CC=2)C)C=C1 ZKPKTZCTFLSGPY-UHFFFAOYSA-N 0.000 claims 1
- STRVXDIDUBEWHZ-UHFFFAOYSA-N N-(1-methylcyclopropyl)-1-[2-(3-methyl-2-oxoimidazolidin-1-yl)acetyl]-2,3-dihydroindole-6-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC=C2CCN(C2=C1)C(CN1C(N(CC1)C)=O)=O STRVXDIDUBEWHZ-UHFFFAOYSA-N 0.000 claims 1
- SMKVDACTSGYVQK-UHFFFAOYSA-N N-(1-methylcyclopropyl)-2-[(1-methylpyrazol-4-yl)methyl]-3-(5-methyl-1,3,4-thiadiazol-2-yl)benzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N=C(N2C=2SC(=NN=2)C)CC=2C=NN(C=2)C)C=C1 SMKVDACTSGYVQK-UHFFFAOYSA-N 0.000 claims 1
- FXKITHZQAVITJF-UHFFFAOYSA-N N-(1-methylcyclopropyl)-2-[2-(1-methylpyrazol-4-yl)ethyl]-3-(5-methyl-1,3,4-thiadiazol-2-yl)benzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N=C(N2C=2SC(=NN=2)C)CCC=2C=NN(C=2)C)C=C1 FXKITHZQAVITJF-UHFFFAOYSA-N 0.000 claims 1
- AVLHRYJRSNZBED-UHFFFAOYSA-N N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1-(2-morpholin-4-ylethyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2OC(=NN=2)C)=O)CCN2CCOCC2)C=C1 AVLHRYJRSNZBED-UHFFFAOYSA-N 0.000 claims 1
- DABBWCXMUHKRJB-UHFFFAOYSA-N N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1-[(1-methylpiperidin-2-yl)methyl]-2-oxobenzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2OC(=NN=2)C)=O)CC2N(CCCC2)C)C=C1 DABBWCXMUHKRJB-UHFFFAOYSA-N 0.000 claims 1
- RIPSYLYZLBTACK-UHFFFAOYSA-N N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1-[(1-methylpiperidin-3-yl)methyl]-2-oxobenzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2OC(=NN=2)C)=O)CC2CN(CCC2)C)C=C1 RIPSYLYZLBTACK-UHFFFAOYSA-N 0.000 claims 1
- BHAVDUPEQITIPI-UHFFFAOYSA-N N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)-2-oxo-1H-benzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(NC(N2C=2OC(=NN=2)C)=O)C=C1 BHAVDUPEQITIPI-UHFFFAOYSA-N 0.000 claims 1
- XLDSZXZYERSGQI-UHFFFAOYSA-N N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-1-(1,3-oxazol-2-ylmethyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CC=2OC=CN=2)C=C1 XLDSZXZYERSGQI-UHFFFAOYSA-N 0.000 claims 1
- VZZPFUSXCMSZQK-UHFFFAOYSA-N N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-1-(2-morpholin-4-ylethyl)-2-oxobenzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CCN2CCOCC2)C=C1 VZZPFUSXCMSZQK-UHFFFAOYSA-N 0.000 claims 1
- DEJDCURLUNVOQT-UHFFFAOYSA-N N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-1-[(2-methyl-1,3-thiazol-5-yl)methyl]-2-oxobenzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CC2=CN=C(S2)C)C=C1 DEJDCURLUNVOQT-UHFFFAOYSA-N 0.000 claims 1
- ZCESPYXJQGXAPK-UHFFFAOYSA-N N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-1-[(5-methylthiophen-2-yl)methyl]-2-oxobenzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CC=2SC(=CC=2)C)C=C1 ZCESPYXJQGXAPK-UHFFFAOYSA-N 0.000 claims 1
- BHRKRRUBKCDWEP-UHFFFAOYSA-N N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxo-1-(1H-pyrazol-4-ylmethyl)benzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CC=2C=NNC=2)C=C1 BHRKRRUBKCDWEP-UHFFFAOYSA-N 0.000 claims 1
- CMNWMZZFZKWTGG-UHFFFAOYSA-N N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxo-1-prop-2-ynylbenzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CC#C)C=C1 CMNWMZZFZKWTGG-UHFFFAOYSA-N 0.000 claims 1
- WAJTXXUCGUCMRN-UHFFFAOYSA-N N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxo-1H-benzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(NC(N2C=2SC(=NN=2)C)=O)C=C1 WAJTXXUCGUCMRN-UHFFFAOYSA-N 0.000 claims 1
- ALHIKLRFEXYUCD-UHFFFAOYSA-N N-(1-methylcyclopropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)benzimidazole-5-sulfonamide Chemical compound CC1(CC1)NS(=O)(=O)C1=CC2=C(N=CN2C=2SC(=NN=2)C)C=C1 ALHIKLRFEXYUCD-UHFFFAOYSA-N 0.000 claims 1
- JQNSPAJTSKWHHG-UHFFFAOYSA-N N-[1-(fluoromethyl)cyclopropyl]-1-(2-methoxyethyl)-2-oxo-3-(1,2,4-thiadiazol-5-yl)benzimidazole-5-sulfonamide Chemical compound FCC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C2=NC=NS2)=O)CCOC)C=C1 JQNSPAJTSKWHHG-UHFFFAOYSA-N 0.000 claims 1
- YKKIHBULNBPEGE-UHFFFAOYSA-N N-[1-(fluoromethyl)cyclopropyl]-1-(2-methoxyethyl)-3-(3-methyl-1,2,4-thiadiazol-5-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound FCC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C2=NC(=NS2)C)=O)CCOC)C=C1 YKKIHBULNBPEGE-UHFFFAOYSA-N 0.000 claims 1
- QLLPBIWDLUCKEM-UHFFFAOYSA-N N-[1-(fluoromethyl)cyclopropyl]-1-(2-methoxyethyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound FCC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CCOC)C=C1 QLLPBIWDLUCKEM-UHFFFAOYSA-N 0.000 claims 1
- LVTMEZYMPWSCCS-UHFFFAOYSA-N N-[1-(fluoromethyl)cyclopropyl]-1-(3-methoxypropyl)-3-(3-methyl-1,2,4-thiadiazol-5-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound FCC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C2=NC(=NS2)C)=O)CCCOC)C=C1 LVTMEZYMPWSCCS-UHFFFAOYSA-N 0.000 claims 1
- QGNLLXADJQMWOS-UHFFFAOYSA-N N-[1-(fluoromethyl)cyclopropyl]-1-(3-methoxypropyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound FCC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)CCCOC)C=C1 QGNLLXADJQMWOS-UHFFFAOYSA-N 0.000 claims 1
- FFLHOMICNXERKZ-UHFFFAOYSA-N N-[1-(fluoromethyl)cyclopropyl]-1-methyl-2-oxo-3-(1,2,4-thiadiazol-5-yl)benzimidazole-5-sulfonamide Chemical compound FCC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C2=NC=NS2)=O)C)C=C1 FFLHOMICNXERKZ-UHFFFAOYSA-N 0.000 claims 1
- UKBCHZUVQPIRPZ-UHFFFAOYSA-N N-[1-(fluoromethyl)cyclopropyl]-1-methyl-3-(3-methyl-1,2,4-thiadiazol-5-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound FCC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C2=NC(=NS2)C)=O)C)C=C1 UKBCHZUVQPIRPZ-UHFFFAOYSA-N 0.000 claims 1
- YWUZHDSWAXKMLZ-UHFFFAOYSA-N N-[1-(fluoromethyl)cyclopropyl]-1-methyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxobenzimidazole-5-sulfonamide Chemical compound FCC1(CC1)NS(=O)(=O)C1=CC2=C(N(C(N2C=2SC(=NN=2)C)=O)C)C=C1 YWUZHDSWAXKMLZ-UHFFFAOYSA-N 0.000 claims 1
- CQVPONDBKVFKJA-UHFFFAOYSA-N N-[4-[[3-methyl-5-[(1-methylcyclopropyl)sulfamoyl]-2-oxobenzimidazol-1-yl]methyl]phenyl]acetamide Chemical compound CN1C(N(C2=C1C=C(C=C2)S(NC1(CC1)C)(=O)=O)CC1=CC=C(C=C1)NC(C)=O)=O CQVPONDBKVFKJA-UHFFFAOYSA-N 0.000 claims 1
- RJKNCKPSQLFNCQ-UHFFFAOYSA-N N-[[6-[(1-methylcyclopropyl)sulfamoyl]-1-(5-methyl-1,3,4-thiadiazol-2-yl)benzimidazol-2-yl]methyl]acetamide Chemical compound CC1(CC1)NS(=O)(=O)C=1C=CC2=C(N(C(=N2)CNC(C)=O)C=2SC(=NN=2)C)C=1 RJKNCKPSQLFNCQ-UHFFFAOYSA-N 0.000 claims 1
- OYGWNOAAGJFOSY-UHFFFAOYSA-N N-ethyl-3-methyl-6-[(1-methylcyclopropyl)sulfamoyl]-2-oxobenzimidazole-1-carboxamide Chemical compound C(C)NC(=O)N1C(N(C2=C1C=C(C=C2)S(NC1(CC1)C)(=O)=O)C)=O OYGWNOAAGJFOSY-UHFFFAOYSA-N 0.000 claims 1
- LJIUFWGIGZAHHV-UHFFFAOYSA-N N-methyl-3-[2-[3-methyl-6-[(1-methylcyclopropyl)sulfamoyl]-2-oxobenzimidazol-1-yl]-1,3-thiazol-5-yl]propanamide Chemical compound CNC(CCC1=CN=C(S1)N1C(N(C2=C1C=C(C=C2)S(NC1(CC1)C)(=O)=O)C)=O)=O LJIUFWGIGZAHHV-UHFFFAOYSA-N 0.000 claims 1
- BJRBFCATZRUHSV-UHFFFAOYSA-N N-methyl-5-[[5-[(1-methylcyclopropyl)sulfamoyl]-3-(5-methyl-1,3,4-oxadiazol-2-yl)-2-oxobenzimidazol-1-yl]methyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound CNC(=O)C1=NOC(=N1)CN1C(N(C2=C1C=CC(=C2)S(NC1(CC1)C)(=O)=O)C=1OC(=NN=1)C)=O BJRBFCATZRUHSV-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- JAGSRDZQDPMNQC-UHFFFAOYSA-N ethyl 3-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-[(1-methylcyclopropyl)sulfamoyl]-2-oxobenzimidazole-1-carboxylate Chemical compound CC=1SC(=C(N=1)C)CN1C(N(C2=C1C=CC(=C2)S(NC1(CC1)C)(=O)=O)C(=O)OCC)=O JAGSRDZQDPMNQC-UHFFFAOYSA-N 0.000 claims 1
- RTWYRGQNUFDFQK-UHFFFAOYSA-N ethyl 3-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-[(1-methylcyclopropyl)sulfamoyl]indole-1-carboxylate Chemical compound CC=1SC(=C(N=1)C)CC1=CN(C2=CC(=CC=C12)S(NC1(CC1)C)(=O)=O)C(=O)OCC RTWYRGQNUFDFQK-UHFFFAOYSA-N 0.000 claims 1
- KWBOLRRCPKOPJD-UHFFFAOYSA-N ethyl 3-[(4-fluorophenyl)methyl]-6-[(1-methylcyclopropyl)sulfamoyl]-2-oxobenzimidazole-1-carboxylate Chemical compound FC1=CC=C(C=C1)CN1C(N(C2=C1C=CC(=C2)S(NC1(CC1)C)(=O)=O)C(=O)OCC)=O KWBOLRRCPKOPJD-UHFFFAOYSA-N 0.000 claims 1
- HNMSSBYROMUXRO-UHFFFAOYSA-N ethyl 3-methyl-6-[(1-methylcyclopropyl)sulfamoyl]-2-oxobenzimidazole-1-carboxylate Chemical compound CN1C(N(C2=C1C=CC(=C2)S(NC1(CC1)C)(=O)=O)C(=O)OCC)=O HNMSSBYROMUXRO-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- AYQAKCMWAXKCOD-UHFFFAOYSA-N methyl 6-(cyclopropylsulfamoyl)-1-propan-2-ylindazole-4-carboxylate Chemical compound C=1C=2N(C(C)C)N=CC=2C(C(=O)OC)=CC=1S(=O)(=O)NC1CC1 AYQAKCMWAXKCOD-UHFFFAOYSA-N 0.000 claims 1
- JMHAQSPSULIYEH-UHFFFAOYSA-N n-tert-butyl-1h-indole-6-sulfonamide Chemical compound CC(C)(C)NS(=O)(=O)C1=CC=C2C=CNC2=C1 JMHAQSPSULIYEH-UHFFFAOYSA-N 0.000 claims 1
- CQVWIOGREDVQJJ-UHFFFAOYSA-N n-tert-butyl-3-(cyclohexen-1-yl)-1h-indole-6-sulfonamide Chemical compound C=1NC2=CC(S(=O)(=O)NC(C)(C)C)=CC=C2C=1C1=CCCCC1 CQVWIOGREDVQJJ-UHFFFAOYSA-N 0.000 claims 1
- IOBUGEAMECKURV-UHFFFAOYSA-N n-tert-butyl-3-cyclohexyl-1h-indole-6-sulfonamide Chemical compound C=1NC2=CC(S(=O)(=O)NC(C)(C)C)=CC=C2C=1C1CCCCC1 IOBUGEAMECKURV-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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| MA41140A (fr) | 2014-12-12 | 2017-10-17 | Cancer Research Tech Ltd | Dérivés de 2,4-dioxo-quinazoline-6-sulfonamide en tant qu'inhibiteurs de la parg |
| MA41179A (fr) | 2014-12-19 | 2017-10-24 | Cancer Research Tech Ltd | Composés inhibiteurs de parg |
| EP3947351A4 (en) | 2019-03-29 | 2022-12-07 | Board of Regents, The University of Texas System | SMALL MOLECULAR PARG INHIBITORS AND METHODS OF USE |
| EP4031249A1 (en) * | 2019-09-20 | 2022-07-27 | Ideaya Biosciences, Inc. | 4-substituted indole and indazole sulfonamido derivatives as parg inhibitors |
| WO2023057394A1 (en) | 2021-10-04 | 2023-04-13 | Forx Therapeutics Ag | N,n-dimethyl-4-(7-(n-(1-methylcyclopropyl)sulfamoyl)-imidazo[1,5-a]pyridin-5-yl)piperazine-1-carboxamide derivatives and the corresponding pyrazolo[1,5-a]pyridine derivatives as parg inhibitors for the treatment of cancer |
| CA3225500A1 (en) | 2021-10-04 | 2023-04-13 | Ulrich Luecking | Parg inhibitory compounds |
| EP4401721A4 (en) | 2021-10-17 | 2025-10-15 | Univ Of South Alabama Foundation For Research And Commercialization | CANCER TREATMENT |
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| CR20240391A (es) * | 2022-03-23 | 2024-11-05 | Ideaya Biosciences Inc | Compuestos de indazol sustituidos con piperazina como inhibidores de parg |
| CN114685283B (zh) * | 2022-04-06 | 2024-02-27 | 南京艾康生物科技有限公司 | 一种1-(氟甲基)环丙胺盐酸盐的制备方法 |
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| CN117157299B (zh) * | 2022-04-28 | 2024-05-28 | 北京丹擎医药科技有限公司 | 三环杂环衍生物及其组合物和应用 |
| CA3251429A1 (en) | 2022-05-17 | 2023-11-23 | 858 Therapeutics, Inc. | PARG INHIBITORS |
| AU2023297713A1 (en) * | 2022-06-29 | 2025-02-13 | Hangzhou Synrx Therapeutics Biomedical Technology Co., Ltd. | Five-membered and six-membered nitrogen-containing compound, and intermediate, preparation method and use thereof |
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| WO2024080792A1 (en) * | 2022-10-13 | 2024-04-18 | Hanmi Pharm. Co., Ltd. | Novel heterobicyclic compound for inhibiting yap-tead interaction and pharmaceutical composition comprising same |
| WO2024120519A1 (zh) * | 2022-12-09 | 2024-06-13 | 捷思英达控股有限公司 | Tead抑制剂、其制备方法和在医学上的应用 |
| WO2024173234A1 (en) * | 2023-02-13 | 2024-08-22 | Arase Therapeutics Inc. | Inhibitors of parg |
| WO2024209035A1 (en) | 2023-04-05 | 2024-10-10 | Forx Therapeutics Ag | Parg inhibitory compounds |
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| WO2024243304A2 (en) * | 2023-05-23 | 2024-11-28 | Quantx Biosciences Us, Inc. | Bicyclic heteroaryl compounds |
| WO2024254990A1 (zh) * | 2023-06-16 | 2024-12-19 | 上海璎黎药业有限公司 | 一种杂芳环结构化合物、其药物组合物及应用 |
| WO2025035108A2 (en) * | 2023-08-10 | 2025-02-13 | Arase Therapeutics Inc. | Inhibitors of parg |
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| WO2025093755A1 (en) | 2023-11-01 | 2025-05-08 | Forx Therapeutics Ag | Novel parc inhibitors |
| WO2025098445A1 (zh) * | 2023-11-07 | 2025-05-15 | 南京同诺康医药科技有限公司 | Parg抑制剂及其制备方法和用途 |
| WO2025108225A1 (zh) * | 2023-11-20 | 2025-05-30 | 上海复星医药(集团)股份有限公司 | 作为parg抑制剂的含氮三环衍生物 |
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| EP4031249A1 (en) | 2019-09-20 | 2022-07-27 | Ideaya Biosciences, Inc. | 4-substituted indole and indazole sulfonamido derivatives as parg inhibitors |
| CA3225500A1 (en) | 2021-10-04 | 2023-04-13 | Ulrich Luecking | Parg inhibitory compounds |
| CR20240391A (es) | 2022-03-23 | 2024-11-05 | Ideaya Biosciences Inc | Compuestos de indazol sustituidos con piperazina como inhibidores de parg |
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2015
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- 2015-12-17 JP JP2017532912A patent/JP6673920B2/ja active Active
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- 2017-06-28 ZA ZA2017/04383A patent/ZA201704383B/en unknown
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- 2024-09-19 US US18/889,613 patent/US20250223266A1/en active Pending
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