OA12784A - Indazoles substutués avec une activité anticancéreuse. - Google Patents

Info

Publication number

OA12784A

OA12784A OA1200400236A OA1200400236A OA12784A OA 12784 A OA12784 A OA 12784A OA 1200400236 A OA1200400236 A OA 1200400236A OA 1200400236 A OA1200400236 A OA 1200400236A OA 12784 A OA12784 A OA 12784A

Authority

OA

OAPI

Prior art keywords

indazol

phenyl

benzenesulfonamide

methanesulfonylbenzenesulfonamide

methylsulfonylbenzenesulfonamide

Prior art date

2002-03-11

Links

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• 150000002473 indoazoles Chemical group 0.000 title abstract 4
• 230000001093 anti-cancer Effects 0.000 title description 5
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 39
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 39
• 238000004519 manufacturing process Methods 0.000 claims abstract description 4
• -1 Chloro-1H-indazol-5-yl Chemical group 0.000 claims description 257
• 150000001875 compounds Chemical class 0.000 claims description 129
• 125000003118 aryl group Chemical group 0.000 claims description 38
• 125000000623 heterocyclic group Chemical group 0.000 claims description 30
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 27
• 125000002947 alkylene group Chemical group 0.000 claims description 23
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• 125000003107 substituted aryl group Chemical group 0.000 claims description 19
• 125000000217 alkyl group Chemical group 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 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 17
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 206010028980 Neoplasm Diseases 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 239000003112 inhibitor Substances 0.000 claims description 16
• 108090000461 Aurora Kinase A Proteins 0.000 claims description 15
• 102100032311 Aurora kinase A Human genes 0.000 claims description 15
• 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 15
• 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 15
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 12
• 239000005711 Benzoic acid Substances 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 229940124530 sulfonamide Drugs 0.000 claims description 11
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 10
• 101150001535 SRC gene Proteins 0.000 claims description 10
• 235000010233 benzoic acid Nutrition 0.000 claims description 10
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• SVOWCBCFXJLRIU-UHFFFAOYSA-N N-[3-(4-hydroxyphenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(O)=CC=3)C2=C1 SVOWCBCFXJLRIU-UHFFFAOYSA-N 0.000 claims description 8
• 201000011510 cancer Diseases 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 229910052705 radium Inorganic materials 0.000 claims description 8
• 229910052701 rubidium Inorganic materials 0.000 claims description 8
• 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims description 7
• 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 claims description 7
• 101001034652 Homo sapiens Insulin-like growth factor 1 receptor Proteins 0.000 claims description 7
• 102100039688 Insulin-like growth factor 1 receptor Human genes 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• ZYRMFMZOLKOEFZ-UHFFFAOYSA-N n-[3-(3-aminophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(N)C=CC=3)C2=C1 ZYRMFMZOLKOEFZ-UHFFFAOYSA-N 0.000 claims description 7
• FNTHMNHMNKDQEC-UHFFFAOYSA-N n-[3-(3-bromophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(Br)C=CC=3)C2=C1 FNTHMNHMNKDQEC-UHFFFAOYSA-N 0.000 claims description 7
• BWAGAWVSXXJADX-UHFFFAOYSA-N n-[4-[(3-phenyl-1h-indazol-5-yl)sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 BWAGAWVSXXJADX-UHFFFAOYSA-N 0.000 claims description 7
• 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims description 6
• 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• IAKJPIODQWXTDR-XYOKQWHBSA-N n-[3-[(e)-2-(4-chlorophenyl)ethenyl]-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2\C=C\C=3C=CC(Cl)=CC=3)C2=C1 IAKJPIODQWXTDR-XYOKQWHBSA-N 0.000 claims description 6
• KMWBIKVAWJEHCX-UHFFFAOYSA-N 1h-indazol-5-yl 3-fluorobenzenesulfonate Chemical compound FC1=CC=CC(S(=O)(=O)OC=2C=C3C=NNC3=CC=2)=C1 KMWBIKVAWJEHCX-UHFFFAOYSA-N 0.000 claims description 5
• BFROGUGBGKIQPH-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 BFROGUGBGKIQPH-UHFFFAOYSA-N 0.000 claims description 5
• ZKDVCIAPCQMSJW-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-pyridin-4-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CN=CC=3)C2=C1 ZKDVCIAPCQMSJW-UHFFFAOYSA-N 0.000 claims description 5
• ZCVNZBOMBPHXHG-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-thiophen-2-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3SC=CC=3)C2=C1 ZCVNZBOMBPHXHG-UHFFFAOYSA-N 0.000 claims description 5
• SMCGMAXYINPFGK-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2-phenylethyl)-2h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2CCC=3C=CC=CC=3)C2=C1 SMCGMAXYINPFGK-UHFFFAOYSA-N 0.000 claims description 5
• IRYILYDRLZINJI-UHFFFAOYSA-N 3,4-dichloro-n-(3-methyl-2h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C2C(C)=NNC2=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 IRYILYDRLZINJI-UHFFFAOYSA-N 0.000 claims description 5
• PYEANTVULAMRGV-UHFFFAOYSA-N 3-amino-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound NC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 PYEANTVULAMRGV-UHFFFAOYSA-N 0.000 claims description 5
• DMRVOBLLZGFOIS-UHFFFAOYSA-N 3-fluoro-n-(1h-indazol-5-yl)benzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C=NNC3=CC=2)=C1 DMRVOBLLZGFOIS-UHFFFAOYSA-N 0.000 claims description 5
• HGMGIWTWOLKILD-UHFFFAOYSA-N 3-fluoro-n-(3-methyl-2h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C2C(C)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 HGMGIWTWOLKILD-UHFFFAOYSA-N 0.000 claims description 5
• XVCOPODOXQGYFA-UHFFFAOYSA-N 3-fluoro-n-(3-oxo-1,2-dihydroindazol-5-yl)benzenesulfonamide Chemical compound C1=C2C(O)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 XVCOPODOXQGYFA-UHFFFAOYSA-N 0.000 claims description 5
• OHDWGXIIXQZSBW-UHFFFAOYSA-N 3-fluoro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 OHDWGXIIXQZSBW-UHFFFAOYSA-N 0.000 claims description 5
• SBSUSUMJNWUBRC-UHFFFAOYSA-N 3-fluoro-n-[3-(methanesulfonamido)-1h-indazol-5-yl]benzenesulfonamide Chemical compound C1=C2C(NS(=O)(=O)C)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 SBSUSUMJNWUBRC-UHFFFAOYSA-N 0.000 claims description 5
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• VRVWVMZURIDGGD-UHFFFAOYSA-N 4-amino-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 VRVWVMZURIDGGD-UHFFFAOYSA-N 0.000 claims description 5
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• YTCROYMIRGBRIQ-UHFFFAOYSA-N 5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazole-3-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C(N)=O)C2=C1 YTCROYMIRGBRIQ-UHFFFAOYSA-N 0.000 claims description 5
• YQWKKTMDPYCPOE-UHFFFAOYSA-N 5-[(2-methylsulfonylphenyl)sulfonylamino]-n-phenyl-1h-indazole-3-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C(=O)NC=3C=CC=CC=3)C2=C1 YQWKKTMDPYCPOE-UHFFFAOYSA-N 0.000 claims description 5
• YIMOCMSIWHYZRI-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfonylamino]-n-methyl-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 YIMOCMSIWHYZRI-UHFFFAOYSA-N 0.000 claims description 5
• ZYRQIKVFBFGSTC-UHFFFAOYSA-N N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]-2-(trifluoromethoxy)benzenesulfonamide Chemical compound FC(F)(F)OC1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3NC4=CC=CC=C4C=3)C2=C1 ZYRQIKVFBFGSTC-UHFFFAOYSA-N 0.000 claims description 5
• PCAXMUPGGRFMOI-UHFFFAOYSA-N N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3NC4=CC=CC=C4C=3)C2=C1 PCAXMUPGGRFMOI-UHFFFAOYSA-N 0.000 claims description 5
• PMZWMTCHDPQLFH-UHFFFAOYSA-N N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]thiophene-2-sulfonamide Chemical compound C=1C=C2NN=C(C=3NC4=CC=CC=C4C=3)C2=CC=1NS(=O)(=O)C1=CC=CS1 PMZWMTCHDPQLFH-UHFFFAOYSA-N 0.000 claims description 5
• DYNFFHPGUWOLQT-UHFFFAOYSA-N N-[3-(5-methoxy-1H-indol-2-yl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C=1C2=CC(OC)=CC=C2NC=1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O DYNFFHPGUWOLQT-UHFFFAOYSA-N 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 5
• JIPJPRTZKUKIFK-UHFFFAOYSA-N n-(1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2)C2=C1 JIPJPRTZKUKIFK-UHFFFAOYSA-N 0.000 claims description 5
• RGWZMNYEINMLSB-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)-3-fluorobenzenesulfonamide Chemical compound C1=C2C(N)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 RGWZMNYEINMLSB-UHFFFAOYSA-N 0.000 claims description 5
• WMGQUWSQDYYQSI-UHFFFAOYSA-N n-(3-bromo-2h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2Br)C2=C1 WMGQUWSQDYYQSI-UHFFFAOYSA-N 0.000 claims description 5
• RBVQLBDPNPEWPJ-UHFFFAOYSA-N n-(3-chloro-2h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2Cl)C2=C1 RBVQLBDPNPEWPJ-UHFFFAOYSA-N 0.000 claims description 5
• QMKOXXIAWGTJLB-UHFFFAOYSA-N n-(3-methyl-2h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C2C(C)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O QMKOXXIAWGTJLB-UHFFFAOYSA-N 0.000 claims description 5
• YLTLNEMPCOXATC-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)cyclohexanesulfonamide Chemical compound C1CCCCC1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 YLTLNEMPCOXATC-UHFFFAOYSA-N 0.000 claims description 5
• IBXPTSRLYBPVJO-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)piperidine-4-sulfonamide Chemical compound C1CNCCC1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 IBXPTSRLYBPVJO-UHFFFAOYSA-N 0.000 claims description 5
• NNFNZBCXJLVDEI-UHFFFAOYSA-N n-[2-[5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazol-3-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O NNFNZBCXJLVDEI-UHFFFAOYSA-N 0.000 claims description 5
• ZIQNKRBWHDSEKD-UHFFFAOYSA-N n-[3-(benzylamino)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2NCC=3C=CC=CC=3)C2=C1 ZIQNKRBWHDSEKD-UHFFFAOYSA-N 0.000 claims description 5
• GXXHQJGQROXUDO-UHFFFAOYSA-N n-[3-[2-(4-chlorophenyl)ethyl]-2h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2CCC=3C=CC(Cl)=CC=3)C2=C1 GXXHQJGQROXUDO-UHFFFAOYSA-N 0.000 claims description 5
• SGZMDYMDGSNYSI-UHFFFAOYSA-N n-[3-[2-(4-fluorophenyl)ethyl]-2h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2CCC=3C=CC(F)=CC=3)C2=C1 SGZMDYMDGSNYSI-UHFFFAOYSA-N 0.000 claims description 5
• AHFLNQASNRILFE-UHFFFAOYSA-N n-[3-[4-(dimethylamino)phenyl]-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(N(C)C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O AHFLNQASNRILFE-UHFFFAOYSA-N 0.000 claims description 5
• GFEQLGKQKXFMKV-UHFFFAOYSA-N n-[5-[(3-fluorophenyl)sulfonylamino]-1h-indazol-3-yl]acetamide Chemical compound C1=C2C(NC(=O)C)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 GFEQLGKQKXFMKV-UHFFFAOYSA-N 0.000 claims description 5
• SQFAUZVASKEZAB-UHFFFAOYSA-N n-cyclohexyl-5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazole-3-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C(=O)NC3CCCCC3)C2=C1 SQFAUZVASKEZAB-UHFFFAOYSA-N 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 5
• SWWJMFAMHNRHOA-UHFFFAOYSA-N 2-methylsulfonyl-N-[3-(1H-pyrrol-2-yl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3NC=CC=3)C2=C1 SWWJMFAMHNRHOA-UHFFFAOYSA-N 0.000 claims description 4
• YNFJJRNYCSVSGB-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-naphthalen-1-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C4=CC=CC=C4C=CC=3)C2=C1 YNFJJRNYCSVSGB-UHFFFAOYSA-N 0.000 claims description 4
• BEPBFIIJPPVCKR-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-thiophen-3-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C3=CSC=C3)C2=C1 BEPBFIIJPPVCKR-UHFFFAOYSA-N 0.000 claims description 4
• DWWIPKOTLDERIH-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2-phenylethynyl)-2h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C#CC=3C=CC=CC=3)C2=C1 DWWIPKOTLDERIH-UHFFFAOYSA-N 0.000 claims description 4
• RSHWLECTDYHGLL-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(3-nitrophenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(C=CC=3)[N+]([O-])=O)C2=C1 RSHWLECTDYHGLL-UHFFFAOYSA-N 0.000 claims description 4
• SIHPXXPBIZDJGS-UHFFFAOYSA-N 3-fluoro-n-(3-iodo-2h-indazol-5-yl)benzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(I)=NNC3=CC=2)=C1 SIHPXXPBIZDJGS-UHFFFAOYSA-N 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
• PPHVRPNSDQPTQP-UHFFFAOYSA-N N-[3-(1H-benzimidazol-2-yl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3NC4=CC=CC=C4N=3)C2=C1 PPHVRPNSDQPTQP-UHFFFAOYSA-N 0.000 claims description 4
• SGKZMHSWJVCVNB-UHFFFAOYSA-N N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound C=1C=C2NN=C(C=3NC4=CC=CC=C4C=3)C2=CC=1NS(=O)(=O)C1=CC=CC=C1 SGKZMHSWJVCVNB-UHFFFAOYSA-N 0.000 claims description 4
• IABVUQZTRBAVOA-UHFFFAOYSA-N N-[3-(4-hydroxyphenyl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound C1=CC(O)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1 IABVUQZTRBAVOA-UHFFFAOYSA-N 0.000 claims description 4
• MYZXIZXWICYCBX-UHFFFAOYSA-N n-(1h-indazol-5-yl)benzenesulfonamide Chemical compound C=1C=C2NN=CC2=CC=1NS(=O)(=O)C1=CC=CC=C1 MYZXIZXWICYCBX-UHFFFAOYSA-N 0.000 claims description 4
• JPJLFYPICGORTG-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)-2,6-dichlorobenzenesulfonamide Chemical compound C1=C2C(N)=NNC2=CC=C1NS(=O)(=O)C1=C(Cl)C=CC=C1Cl JPJLFYPICGORTG-UHFFFAOYSA-N 0.000 claims description 4
• MKZMSLHAPRHWEX-UHFFFAOYSA-N n-(3-anilino-1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2NC=3C=CC=CC=3)C2=C1 MKZMSLHAPRHWEX-UHFFFAOYSA-N 0.000 claims description 4
• QXMQCLOJLMJUBM-UHFFFAOYSA-N n-(3-chloro-2h-indazol-5-yl)-3-fluorobenzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(Cl)=NNC3=CC=2)=C1 QXMQCLOJLMJUBM-UHFFFAOYSA-N 0.000 claims description 4
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