MXPA04008446A - Indazoles sustituidos, con actividad anticancerosa. - Google Patents

Info

Publication number

MXPA04008446A

MXPA04008446A MXPA04008446A MXPA04008446A MXPA04008446A MX PA04008446 A MXPA04008446 A MX PA04008446A MX PA04008446 A MXPA04008446 A MX PA04008446A MX PA04008446 A MXPA04008446 A MX PA04008446A MX PA04008446 A MXPA04008446 A MX PA04008446A

Authority

MX

Mexico

Prior art keywords

indazol

benzenesulfonamide

phenyl

methanesulfonyl

ndazol

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 45
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 45
• 238000004519 manufacturing process Methods 0.000 claims abstract description 4
• -1 3-Fluorobenzenesulfonylamino Chemical group 0.000 claims description 248
• 150000001875 compounds Chemical class 0.000 claims description 131
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 65
• 238000006243 chemical reaction Methods 0.000 claims description 50
• 229940124530 sulfonamide Drugs 0.000 claims description 42
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 125000003118 aryl group Chemical group 0.000 claims description 30
• 125000002947 alkylene group Chemical group 0.000 claims description 23
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• 125000000217 alkyl group Chemical group 0.000 claims description 19
• 239000003112 inhibitor Substances 0.000 claims description 19
• 125000003107 substituted aryl group Chemical group 0.000 claims description 19
• 206010028980 Neoplasm Diseases 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 16
• 108090000461 Aurora Kinase A Proteins 0.000 claims description 14
• 102100032311 Aurora kinase A Human genes 0.000 claims description 14
• 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 14
• 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 14
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 14
• 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 13
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 12
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 11
• 101150001535 SRC gene Proteins 0.000 claims description 10
• 201000011510 cancer Diseases 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
• KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 9
• 101000599951 Homo sapiens Insulin-like growth factor I Proteins 0.000 claims description 9
• 102100037852 Insulin-like growth factor I Human genes 0.000 claims description 9
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
• 229910052799 carbon 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
• 229910052717 sulfur 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
• 239000005711 Benzoic acid Substances 0.000 claims description 7
• 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims description 7
• 102100036252 Cyclin-dependent kinase 4 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
• 239000003814 drug Substances 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
• 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 6
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims description 6
• 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 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 6
• 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 5
• QMCITVXMMYQIOC-UHFFFAOYSA-M 3-fluorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC(F)=C1 QMCITVXMMYQIOC-UHFFFAOYSA-M 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
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 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 5
• 235000010233 benzoic acid Nutrition 0.000 claims description 5
• QSWHZRXINOGWDK-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2N)C2=C1 QSWHZRXINOGWDK-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
• URVXYUWODGMOLS-UHFFFAOYSA-N n-(3-fluorophenyl)-1h-indazole-5-sulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C=C3C=NNC3=CC=2)=C1 URVXYUWODGMOLS-UHFFFAOYSA-N 0.000 claims description 5
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 229920002554 vinyl polymer Polymers 0.000 claims description 5
• MNVMYTVDDOXZLS-UHFFFAOYSA-N 2,4-dimethoxyphenol Chemical compound COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 claims description 4
• MCLNQXKKMHFQLR-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-pyridin-3-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=NC=CC=3)C2=C1 MCLNQXKKMHFQLR-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
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 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 4
• GHJIYUWSHCZVFW-UHFFFAOYSA-N 3,4-dichloro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 GHJIYUWSHCZVFW-UHFFFAOYSA-N 0.000 claims description 4
• SMFFZOQLHYIRDA-UHFFFAOYSA-N 3,4-dimethoxyphenol Chemical compound COC1=CC=C(O)C=C1OC SMFFZOQLHYIRDA-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• 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 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
• 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
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• VYBIMAFGLAQRCL-UHFFFAOYSA-N n-[3-(4-chlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(Cl)=CC=3)C2=C1 VYBIMAFGLAQRCL-UHFFFAOYSA-N 0.000 claims description 4
• PDGFYVAVCLLTNU-UHFFFAOYSA-N n-[3-(4-methoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O PDGFYVAVCLLTNU-UHFFFAOYSA-N 0.000 claims description 4
• SBCCIIVYRCTELP-UHFFFAOYSA-N n-[5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazol-3-yl]acetamide Chemical compound C1=C2C(NC(=O)C)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O SBCCIIVYRCTELP-UHFFFAOYSA-N 0.000 claims description 4
• PPPRVPAMLGCCFM-UHFFFAOYSA-N n-[5-[(3-fluorophenyl)sulfonylamino]-1h-indazol-3-yl]benzamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(NC(=O)C=4C=CC=CC=4)=NNC3=CC=2)=C1 PPPRVPAMLGCCFM-UHFFFAOYSA-N 0.000 claims description 4
• BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 claims description 4
• BXVIZHCADXKMER-CMDGGOBGSA-N (e)-3-[5-[(2-methylsulfonylphenyl)sulfonylamino]-2h-indazol-3-yl]prop-2-enoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2\C=C\C(O)=O)C2=C1 BXVIZHCADXKMER-CMDGGOBGSA-N 0.000 claims description 3
• NDTANLMIEUSSOH-UHFFFAOYSA-N 2-methylsulfonyl-N-[3-(1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3NC4=NC=CC=C4C=3)C2=C1 NDTANLMIEUSSOH-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 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 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
• 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 3
• 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 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
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 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
• 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 3
• 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 3
• HHZVBQIWQWPJSC-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)-2,6-difluorobenzenesulfonamide Chemical compound C1=C2C(N)=NNC2=CC=C1NS(=O)(=O)C1=C(F)C=CC=C1F HHZVBQIWQWPJSC-UHFFFAOYSA-N 0.000 claims description 3
• 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 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
• ASNSAHHPIBUMQH-UHFFFAOYSA-N n-[3-(1-benzothiophen-2-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3SC4=CC=CC=C4C=3)C2=C1 ASNSAHHPIBUMQH-UHFFFAOYSA-N 0.000 claims description 3
• KRGGUWOXZSQAQR-UHFFFAOYSA-N n-[3-(methylamino)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C2C(NC)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O KRGGUWOXZSQAQR-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• MZXBVZRUPDXQCC-UHFFFAOYSA-N n-[5-[(3,5-difluorophenyl)sulfonylamino]-1h-indazol-3-yl]acetamide Chemical compound C1=C2C(NC(=O)C)=NNC2=CC=C1NS(=O)(=O)C1=CC(F)=CC(F)=C1 MZXBVZRUPDXQCC-UHFFFAOYSA-N 0.000 claims description 3
• QADQJUPWUGQXEW-UHFFFAOYSA-N n-[5-[(3,5-difluorophenyl)sulfonylamino]-1h-indazol-3-yl]benzamide Chemical compound FC1=CC(F)=CC(S(=O)(=O)NC=2C=C3C(NC(=O)C=4C=CC=CC=4)=NNC3=CC=2)=C1 QADQJUPWUGQXEW-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 230000001575 pathological effect Effects 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 2
• QHMSFAPYDLUZAX-UHFFFAOYSA-N 1-phenyl-n-(3-phenyl-1h-indazol-5-yl)methanesulfonamide Chemical compound C=1C=C2NN=C(C=3C=CC=CC=3)C2=CC=1NS(=O)(=O)CC1=CC=CC=C1 QHMSFAPYDLUZAX-UHFFFAOYSA-N 0.000 claims description 2
• HEOXSYYWDQPVFL-UHFFFAOYSA-N 2,4,6-trimethyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 HEOXSYYWDQPVFL-UHFFFAOYSA-N 0.000 claims description 2
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
• AHEXHEDIBDQUDB-UHFFFAOYSA-N 2-amino-4,6-dichloro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound NC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 AHEXHEDIBDQUDB-UHFFFAOYSA-N 0.000 claims description 2
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