ZA200406730B - Indazole substituted with an anti-cancerous activity. - Google Patents

Info

Publication number

ZA200406730B

ZA200406730B ZA200406730A ZA200406730A ZA200406730B ZA 200406730 B ZA200406730 B ZA 200406730B ZA 200406730 A ZA200406730 A ZA 200406730A ZA 200406730 A ZA200406730 A ZA 200406730A ZA 200406730 B ZA200406730 B ZA 200406730B

Authority

ZA

South Africa

Prior art keywords

indazol

benzenesulfonamide

phenyl

methanesulfonyl

substituted

Prior art date

2002-03-11

Links

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• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 title description 19
• 230000001093 anti-cancer Effects 0.000 title description 4
• -1 6-(4-methylpiperazin- 1-yl)-1H-benzimidazol-2-yl Chemical group 0.000 claims description 86
• 150000001875 compounds Chemical class 0.000 claims description 63
• 125000003118 aryl group Chemical group 0.000 claims description 33
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 29
• 125000002947 alkylene group Chemical group 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 238000006243 chemical reaction Methods 0.000 claims description 23
• 108091000080 Phosphotransferase Proteins 0.000 claims description 22
• 102000020233 phosphotransferase Human genes 0.000 claims description 22
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 125000000217 alkyl group Chemical group 0.000 claims description 19
• 206010028980 Neoplasm Diseases 0.000 claims description 18
• 125000003107 substituted aryl group Chemical group 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 230000002401 inhibitory effect Effects 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 12
• 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 11
• 239000002253 acid Substances 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
• 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 10
• 201000011510 cancer Diseases 0.000 claims description 10
• 229940124530 sulfonamide Drugs 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 101150001535 SRC gene Proteins 0.000 claims description 8
• 229910052705 radium Inorganic materials 0.000 claims description 8
• 229910052701 rubidium Inorganic materials 0.000 claims description 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 7
• 108090000461 Aurora Kinase A Proteins 0.000 claims description 6
• 102100032311 Aurora kinase A Human genes 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 229910052801 chlorine Chemical group 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 229940126601 medicinal product Drugs 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 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims description 4
• 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 claims description 4
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• 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 3
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 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 3
• 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 3
• OZYAXQWHHTUDPI-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfonylamino]-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)N)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 OZYAXQWHHTUDPI-UHFFFAOYSA-N 0.000 claims description 3
• 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims description 3
• 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims description 3
• 101001034652 Homo sapiens Insulin-like growth factor 1 receptor Proteins 0.000 claims description 3
• 102100039688 Insulin-like growth factor 1 receptor Human genes 0.000 claims description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• 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 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 claims description 3
• 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 3
• 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 3
• KMGGZTLYHGNAKE-UHFFFAOYSA-N n-(3-cyano-1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C#N)C2=C1 KMGGZTLYHGNAKE-UHFFFAOYSA-N 0.000 claims description 3
• LOVSSJYJNHKBJF-UHFFFAOYSA-N n-(3-cyano-1h-indazol-5-yl)-3-fluorobenzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(C#N)=NNC3=CC=2)=C1 LOVSSJYJNHKBJF-UHFFFAOYSA-N 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 230000001575 pathological effect Effects 0.000 claims description 3
• TVOKDUKBWNSZBZ-UHFFFAOYSA-N 2,5-dimethoxy-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 TVOKDUKBWNSZBZ-UHFFFAOYSA-N 0.000 claims description 2
• YTNFPOJQWPBMMP-UHFFFAOYSA-N 2-bromo-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound BrC1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 YTNFPOJQWPBMMP-UHFFFAOYSA-N 0.000 claims description 2
• NXZJFILFGTVFPE-UHFFFAOYSA-N 2-cyano-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C=1C=CC=C(C#N)C=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 NXZJFILFGTVFPE-UHFFFAOYSA-N 0.000 claims description 2
• FJINAFTWNKWKBW-UHFFFAOYSA-N 2-fluoro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound FC1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 FJINAFTWNKWKBW-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• JNGGVHJURWJQIO-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2,3,4-trimethoxyphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound COC1=C(OC)C(OC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O JNGGVHJURWJQIO-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• LVMHHFIKGBLGFK-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2-phenylphenyl)-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)C=3C=CC=CC=3)C2=C1 LVMHHFIKGBLGFK-UHFFFAOYSA-N 0.000 claims description 2
• CXONENHLWWEXSE-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(4-nitrophenyl)-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)[N+]([O-])=O)C2=C1 CXONENHLWWEXSE-UHFFFAOYSA-N 0.000 claims description 2
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
• ZNDOQMZNKKWDTP-UHFFFAOYSA-N 3,4-dichloro-n-(1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2)C2=C1 ZNDOQMZNKKWDTP-UHFFFAOYSA-N 0.000 claims description 2
• VXXKAGRYQZLBNS-UHFFFAOYSA-N 3,4-dichloro-n-(3-chloro-2h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C2C(Cl)=NNC2=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 VXXKAGRYQZLBNS-UHFFFAOYSA-N 0.000 claims description 2
• AWDBPTWYGUHHIQ-UHFFFAOYSA-N 3,4-difluoro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C(F)C(F)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 AWDBPTWYGUHHIQ-UHFFFAOYSA-N 0.000 claims description 2
• AEGKEYKEZSJHPN-UHFFFAOYSA-N 3,5-dichloro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 AEGKEYKEZSJHPN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
• DLPPBHICRMSCBX-UHFFFAOYSA-N 3-[(3-phenyl-1h-indazol-5-yl)sulfamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 DLPPBHICRMSCBX-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• NFAHTVPEUUBFJT-UHFFFAOYSA-N 3-bromo-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound BrC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 NFAHTVPEUUBFJT-UHFFFAOYSA-N 0.000 claims description 2
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
• RNGAJCCTBJROOM-UHFFFAOYSA-N 3-chloro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound ClC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 RNGAJCCTBJROOM-UHFFFAOYSA-N 0.000 claims description 2
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
• MBBXLIKTDIUXCA-UHFFFAOYSA-N 3-cyano-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C=1C=CC(C#N)=CC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 MBBXLIKTDIUXCA-UHFFFAOYSA-N 0.000 claims description 2
• NCHATSXVPBRKKR-UHFFFAOYSA-N 3-fluoro-N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4NC5=CC=CC=C5C=4)=NNC3=CC=2)=C1 NCHATSXVPBRKKR-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• GMUDJTSSYZZRNB-UHFFFAOYSA-N 4-butoxy-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 GMUDJTSSYZZRNB-UHFFFAOYSA-N 0.000 claims description 2
• MYCDWAKLELQQAC-UHFFFAOYSA-N 4-cyano-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 MYCDWAKLELQQAC-UHFFFAOYSA-N 0.000 claims description 2
• LNTRMSKQNAYDND-UHFFFAOYSA-N 4-fluoro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 LNTRMSKQNAYDND-UHFFFAOYSA-N 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• QESTUIHZQQVWEL-UHFFFAOYSA-N 4-methoxy-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 QESTUIHZQQVWEL-UHFFFAOYSA-N 0.000 claims description 2
• DKELXIARPSFBFA-UHFFFAOYSA-N 4-methylsulfonyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 DKELXIARPSFBFA-UHFFFAOYSA-N 0.000 claims description 2
• MEWNTBNDVVRICG-UHFFFAOYSA-N 5-(dibutylamino)-n-(3-phenyl-1h-indazol-5-yl)naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(N(CCCC)CCCC)=CC=CC2=C1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 MEWNTBNDVVRICG-UHFFFAOYSA-N 0.000 claims description 2
• XZAWZBNJMXXCGU-UHFFFAOYSA-N 5-(dimethylamino)-n-[3-[5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazol-3-yl]phenyl]naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NC(C=1)=CC=CC=1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O XZAWZBNJMXXCGU-UHFFFAOYSA-N 0.000 claims description 2
• ATXMCKZTGVVYJO-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfonylamino]-n-phenyl-1h-indazole-3-carboxamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(C(=O)NC=4C=CC=CC=4)=NNC3=CC=2)=C1 ATXMCKZTGVVYJO-UHFFFAOYSA-N 0.000 claims description 2
• JXOMJPQNUVDBQR-UHFFFAOYSA-N 5-chloro-n-(3-phenyl-1h-indazol-5-yl)thiophene-2-sulfonamide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 JXOMJPQNUVDBQR-UHFFFAOYSA-N 0.000 claims description 2
• 239000005711 Benzoic acid Substances 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 2
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
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