HRP20040825A2 - Indazoles substituted with an anti-cancerous activity - Google Patents
Indazoles substituted with an anti-cancerous activity Download PDFInfo
- Publication number
- HRP20040825A2 HRP20040825A2 HR20040825A HRP20040825A HRP20040825A2 HR P20040825 A2 HRP20040825 A2 HR P20040825A2 HR 20040825 A HR20040825 A HR 20040825A HR P20040825 A HRP20040825 A HR P20040825A HR P20040825 A2 HRP20040825 A2 HR P20040825A2
- Authority
- HR
- Croatia
- Prior art keywords
- indazol
- benzenesulfonamide
- phenyl
- methanesulfonyl
- methylsulfonyl
- Prior art date
Links
- 230000001093 anti-cancer Effects 0.000 title description 3
- 150000002473 indoazoles Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 138
- -1 6-(2-dimethylaminomethyl-5-methylmorpholin-4-yl)-1H-benzimidazol-2-yl Chemical group 0.000 claims description 111
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 108091000080 Phosphotransferase Proteins 0.000 claims description 31
- 102000020233 phosphotransferase Human genes 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000003107 substituted aryl group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 108090000461 Aurora Kinase A Proteins 0.000 claims description 15
- 102100032311 Aurora kinase A Human genes 0.000 claims description 15
- 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000005711 Benzoic acid Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 8
- 101001034652 Homo sapiens Insulin-like growth factor 1 receptor Proteins 0.000 claims description 8
- 101150001535 SRC gene Proteins 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
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 102100039688 Insulin-like growth factor 1 receptor Human genes 0.000 claims description 7
- 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 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 229910052801 chlorine Chemical group 0.000 claims description 7
- 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 7
- LNHVNMRKXSHDLT-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)-3,5-difluorobenzenesulfonamide Chemical compound C1=C2C(N)=NNC2=CC=C1NS(=O)(=O)C1=CC(F)=CC(F)=C1 LNHVNMRKXSHDLT-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 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 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
- 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 7
- 229940124530 sulfonamide Drugs 0.000 claims description 7
- 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 6
- 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 6
- 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
- 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 6
- 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 6
- 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 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 6
- 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 6
- 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 6
- 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 6
- MMBLKTXFYPXLON-UHFFFAOYSA-N 3-nitro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 MMBLKTXFYPXLON-UHFFFAOYSA-N 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 6
- 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 6
- 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 6
- 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 6
- 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 6
- 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 6
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims description 6
- 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims description 6
- 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 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 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 6
- 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 6
- 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 6
- 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 6
- 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 6
- 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 6
- 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 6
- 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 6
- RIBHGAYUTBNLNI-UHFFFAOYSA-N n-[3-(4-methoxyphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1 RIBHGAYUTBNLNI-UHFFFAOYSA-N 0.000 claims description 6
- IKKQTWNLZGTAEZ-UHFFFAOYSA-N n-[3-(furan-3-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C3=COC=C3)C2=C1 IKKQTWNLZGTAEZ-UHFFFAOYSA-N 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
- FMCKNGFTTFLGOF-XYOKQWHBSA-N n-[3-[(e)-2-(4-fluorophenyl)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(F)=CC=3)C2=C1 FMCKNGFTTFLGOF-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
- 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 5
- 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 5
- 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 5
- LIMDSQLTBLQFLB-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-naphthalen-2-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C4C=CC=CC4=CC=3)C2=C1 LIMDSQLTBLQFLB-UHFFFAOYSA-N 0.000 claims description 5
- VIKDGOBMESMILG-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-phenylsulfanyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2SC=3C=CC=CC=3)C2=C1 VIKDGOBMESMILG-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- PUXKJVPVEYPABV-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-quinolin-8-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C4=NC=CC=C4C=CC=3)C2=C1 PUXKJVPVEYPABV-UHFFFAOYSA-N 0.000 claims description 5
- 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 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
- 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 5
- 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 5
- SMXAPCOWDIDWOP-ACCUITESSA-N 2-methylsulfonyl-n-[3-[(e)-2-phenylethenyl]-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2\C=C\C=3C=CC=CC=3)C2=C1 SMXAPCOWDIDWOP-ACCUITESSA-N 0.000 claims description 5
- HFNNFEGZWXXPSF-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-[3-(2-trimethylsilylethynyl)phenyl]-1h-indazol-5-yl]benzenesulfonamide Chemical compound C[Si](C)(C)C#CC1=CC=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 HFNNFEGZWXXPSF-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
- 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 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
- 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
- OYNKMNCGIOMAPL-UHFFFAOYSA-N 5-fluoro-2-methylsulfonyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=C(F)C=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 OYNKMNCGIOMAPL-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
- 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 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
- 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 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
- 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 5
- 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 5
- 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 5
- 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 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
- 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
- XDINTPYWJPNKFO-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)pyridine-3-sulfonamide Chemical compound C=1C=CN=CC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 XDINTPYWJPNKFO-UHFFFAOYSA-N 0.000 claims description 5
- YOHJWVZFKYKCFC-UHFFFAOYSA-N n-(6-methyl-3-phenyl-1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound C1=2C=C(NS(=O)(=O)C=3C(=CC=CC=3)S(C)(=O)=O)C(C)=CC=2NN=C1C1=CC=CC=C1 YOHJWVZFKYKCFC-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
- QMCBKPYLCOZQBJ-UHFFFAOYSA-N n-[2-[5-[(3-fluorophenyl)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(F)=C1 QMCBKPYLCOZQBJ-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- PTJURHKDEQOFKR-UHFFFAOYSA-N n-[3-(2-aminophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC=CC=3)N)C2=C1 PTJURHKDEQOFKR-UHFFFAOYSA-N 0.000 claims description 5
- HPJXAQPXNLNSDK-UHFFFAOYSA-N n-[3-(2-methylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CC1=CC=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O HPJXAQPXNLNSDK-UHFFFAOYSA-N 0.000 claims description 5
- RPJDAUSWEFFJMQ-UHFFFAOYSA-N n-[3-(3-cyanophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(C=CC=3)C#N)C2=C1 RPJDAUSWEFFJMQ-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- DUICGHQOLRZWJD-UHFFFAOYSA-N n-[3-(4-fluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(F)=CC=3)C2=C1 DUICGHQOLRZWJD-UHFFFAOYSA-N 0.000 claims description 5
- 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 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
- 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 5
- RLTGXHOHVAGBFB-UHFFFAOYSA-N n-[5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazol-3-yl]benzamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2NC(=O)C=3C=CC=CC=3)C2=C1 RLTGXHOHVAGBFB-UHFFFAOYSA-N 0.000 claims description 5
- 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 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
- 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 4
- 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 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 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
- 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 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229940127554 medical product Drugs 0.000 claims description 4
- RAXAXMSLIFDADE-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)-4-(trifluoromethoxy)benzenesulfonamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 RAXAXMSLIFDADE-UHFFFAOYSA-N 0.000 claims description 4
- RGMSNJXLLHBCGD-UHFFFAOYSA-N n-[3-(1-benzothiophen-3-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C4=CC=CC=C4SC=3)C2=C1 RGMSNJXLLHBCGD-UHFFFAOYSA-N 0.000 claims description 4
- RHCLDPILTWUHCJ-UHFFFAOYSA-N n-[3-(4-aminophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(N)=CC=3)C2=C1 RHCLDPILTWUHCJ-UHFFFAOYSA-N 0.000 claims description 4
- OVBQYGLDWDCWNO-UHFFFAOYSA-N n-[3-(furan-2-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3OC=CC=3)C2=C1 OVBQYGLDWDCWNO-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 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 3
- 229910052794 bromium Inorganic materials 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
- 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 3
- 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 3
- 230000001575 pathological effect Effects 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 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
- 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
- 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
- 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
- AYXXVVZVJYNNPU-UHFFFAOYSA-N 2-methyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 AYXXVVZVJYNNPU-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
- 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
- NNGMCAGGKGJHJA-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(3-phenylmethoxyphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(OCC=4C=CC=CC=4)C=CC=3)C2=C1 NNGMCAGGKGJHJA-UHFFFAOYSA-N 0.000 claims description 2
- USBADQQPQWYQNJ-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(3-propan-2-ylphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CC(C)C1=CC=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 USBADQQPQWYQNJ-UHFFFAOYSA-N 0.000 claims description 2
- JHBIJSRTJQYQKQ-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(4-methylsulfonylphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O JHBIJSRTJQYQKQ-UHFFFAOYSA-N 0.000 claims description 2
- RDNBAGLXYHDJPZ-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(4-phenoxyphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(OC=4C=CC=CC=4)=CC=3)C2=C1 RDNBAGLXYHDJPZ-UHFFFAOYSA-N 0.000 claims description 2
- MLPQRVYXVYSDLT-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(4-phenylmethoxyphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(OCC=4C=CC=CC=4)=CC=3)C2=C1 MLPQRVYXVYSDLT-UHFFFAOYSA-N 0.000 claims description 2
- QGXBDXOTTZFQNQ-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(4-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 QGXBDXOTTZFQNQ-UHFFFAOYSA-N 0.000 claims description 2
- YAKQQGZGXXBXTG-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(4-propan-2-ylphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound C1=CC(C(C)C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O YAKQQGZGXXBXTG-UHFFFAOYSA-N 0.000 claims description 2
- JJANLNUFRDPPOF-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-[3-(trifluoromethoxy)phenyl]-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(OC(F)(F)F)C=CC=3)C2=C1 JJANLNUFRDPPOF-UHFFFAOYSA-N 0.000 claims description 2
- FNJCYRVTGGSQDJ-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-[3-(trifluoromethyl)phenyl]-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)C(F)(F)F)C2=C1 FNJCYRVTGGSQDJ-UHFFFAOYSA-N 0.000 claims description 2
- JWDKHFWPMQFBIF-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-[4-(trifluoromethoxy)phenyl]-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(OC(F)(F)F)=CC=3)C2=C1 JWDKHFWPMQFBIF-UHFFFAOYSA-N 0.000 claims description 2
- RZZHWULQKJRTKR-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-[4-(trifluoromethyl)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)C(F)(F)F)C2=C1 RZZHWULQKJRTKR-UHFFFAOYSA-N 0.000 claims description 2
- UIWNKYKRLSWDPY-UHFFFAOYSA-N 2-nitro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 UIWNKYKRLSWDPY-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
- 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
- GCDSZNYNEYHZNO-UHFFFAOYSA-N 3,5-difluoro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound FC1=CC(F)=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 GCDSZNYNEYHZNO-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
- 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
- FKYAGRQAAOKMNJ-UHFFFAOYSA-N 3-methoxy-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound COC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 FKYAGRQAAOKMNJ-UHFFFAOYSA-N 0.000 claims description 2
- YMZDSSYFEHDUGO-UHFFFAOYSA-N 3-methyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 YMZDSSYFEHDUGO-UHFFFAOYSA-N 0.000 claims description 2
- ISLSMVXTGAQGMN-UHFFFAOYSA-N 4-bromo-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 ISLSMVXTGAQGMN-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
- XGPRBTMLIATVFT-UHFFFAOYSA-N 4-methyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 XGPRBTMLIATVFT-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
- PEUDUYPQHUABPX-UHFFFAOYSA-N 4-nitro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 PEUDUYPQHUABPX-UHFFFAOYSA-N 0.000 claims description 2
- UWMIBHKZTFDAMN-UHFFFAOYSA-N 4-tert-butyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 UWMIBHKZTFDAMN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 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
- PGKIBDXZMQYKSC-UHFFFAOYSA-N 5-(dimethylamino)-n-(3-phenyl-1h-indazol-5-yl)naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 PGKIBDXZMQYKSC-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
- 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
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
- JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical compound NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- ZYHXLDWPAFQSBX-UHFFFAOYSA-N n-(3-dibenzofuran-4-yl-1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=4OC5=CC=CC=C5C=4C=CC=3)C2=C1 ZYHXLDWPAFQSBX-UHFFFAOYSA-N 0.000 claims description 2
- QAPBXCRWMOFRGY-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)-2,1,3-benzoxadiazole-4-sulfonamide Chemical compound C=1C=CC2=NON=C2C=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 QAPBXCRWMOFRGY-UHFFFAOYSA-N 0.000 claims description 2
- BDVIRPJEWYQGRA-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)-2,4,6-tri(propan-2-yl)benzenesulfonamide Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 BDVIRPJEWYQGRA-UHFFFAOYSA-N 0.000 claims description 2
- JJAIABXSZLBNFY-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)-2-(trifluoromethoxy)benzenesulfonamide Chemical compound FC(F)(F)OC1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 JJAIABXSZLBNFY-UHFFFAOYSA-N 0.000 claims description 2
- ZYZUSUWQGWCKBQ-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)-2-(trifluoromethyl)benzenesulfonamide Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 ZYZUSUWQGWCKBQ-UHFFFAOYSA-N 0.000 claims description 2
- JVDZRLPOHNQBGG-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)-3-(trifluoromethyl)benzenesulfonamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 JVDZRLPOHNQBGG-UHFFFAOYSA-N 0.000 claims description 2
- VDDFGASEUCSXLO-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 VDDFGASEUCSXLO-UHFFFAOYSA-N 0.000 claims description 2
- GXCMRLNIRSKEDW-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)butane-1-sulfonamide Chemical compound C12=CC(NS(=O)(=O)CCCC)=CC=C2NN=C1C1=CC=CC=C1 GXCMRLNIRSKEDW-UHFFFAOYSA-N 0.000 claims description 2
- OMENKMXQXAHGCN-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)ethanesulfonamide Chemical compound C12=CC(NS(=O)(=O)CC)=CC=C2NN=C1C1=CC=CC=C1 OMENKMXQXAHGCN-UHFFFAOYSA-N 0.000 claims description 2
- YOWRWXSRPMACOW-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)methanesulfonamide Chemical compound C12=CC(NS(=O)(=O)C)=CC=C2NN=C1C1=CC=CC=C1 YOWRWXSRPMACOW-UHFFFAOYSA-N 0.000 claims description 2
- NBVACTMTKZIYCG-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)naphthalene-1-sulfonamide Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 NBVACTMTKZIYCG-UHFFFAOYSA-N 0.000 claims description 2
- ZGGFGSXSGDVOHL-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)naphthalene-2-sulfonamide Chemical compound C=1C=C2C=CC=CC2=CC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 ZGGFGSXSGDVOHL-UHFFFAOYSA-N 0.000 claims description 2
- ZYLXQFKSXMAKBO-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)propane-1-sulfonamide Chemical compound C12=CC(NS(=O)(=O)CCC)=CC=C2NN=C1C1=CC=CC=C1 ZYLXQFKSXMAKBO-UHFFFAOYSA-N 0.000 claims description 2
- LHUZDSHMEIXBJE-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)propane-2-sulfonamide Chemical compound C12=CC(NS(=O)(=O)C(C)C)=CC=C2NN=C1C1=CC=CC=C1 LHUZDSHMEIXBJE-UHFFFAOYSA-N 0.000 claims description 2
- JITLNYHEWIRGHR-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)quinoline-8-sulfonamide Chemical compound C=1C=CC2=CC=CN=C2C=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 JITLNYHEWIRGHR-UHFFFAOYSA-N 0.000 claims description 2
- UBDFYNJUKQCRLU-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)thiophene-2-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 UBDFYNJUKQCRLU-UHFFFAOYSA-N 0.000 claims description 2
- NZHWWAMEEIBHOC-UHFFFAOYSA-N n-[2-chloro-4-[(3-phenyl-1h-indazol-5-yl)sulfamoyl]phenyl]acetamide Chemical compound C1=C(Cl)C(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 NZHWWAMEEIBHOC-UHFFFAOYSA-N 0.000 claims description 2
- ZLJBLVFGMNVLET-UHFFFAOYSA-N n-[3-(1,3-benzodioxol-5-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C4OCOC4=CC=3)C2=C1 ZLJBLVFGMNVLET-UHFFFAOYSA-N 0.000 claims description 2
- WTLTTWVXFUEYKG-UHFFFAOYSA-N n-[3-(1-benzofuran-2-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3OC4=CC=CC=C4C=3)C2=C1 WTLTTWVXFUEYKG-UHFFFAOYSA-N 0.000 claims description 2
- JWUZPUPHDYPCQO-UHFFFAOYSA-N n-[3-(1h-indol-5-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C4C=CNC4=CC=3)C2=C1 JWUZPUPHDYPCQO-UHFFFAOYSA-N 0.000 claims description 2
- JBKSWEGPKPCXMZ-UHFFFAOYSA-N n-[3-(2,3-dichlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=C(Cl)C=CC=3)Cl)C2=C1 JBKSWEGPKPCXMZ-UHFFFAOYSA-N 0.000 claims description 2
- IAJWJRZRIUSJEA-UHFFFAOYSA-N n-[3-(2,4-dichlorophenyl)-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)Cl)C2=C1 IAJWJRZRIUSJEA-UHFFFAOYSA-N 0.000 claims description 2
- MPQHPKGSKGAKLU-UHFFFAOYSA-N n-[3-(2,4-difluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC(F)=CC=3)F)C2=C1 MPQHPKGSKGAKLU-UHFFFAOYSA-N 0.000 claims description 2
- UGGDZFSYLDVITK-UHFFFAOYSA-N n-[3-(2,4-dimethoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound COC1=CC(OC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O UGGDZFSYLDVITK-UHFFFAOYSA-N 0.000 claims description 2
- YZLPNORYSLGVHH-UHFFFAOYSA-N n-[3-(2,5-dichlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC=C(Cl)C=3)Cl)C2=C1 YZLPNORYSLGVHH-UHFFFAOYSA-N 0.000 claims description 2
- WBVMJGPSZULOJH-UHFFFAOYSA-N n-[3-(2-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=CC=3)Cl)C2=C1 WBVMJGPSZULOJH-UHFFFAOYSA-N 0.000 claims description 2
- FOAWJAYNKAANKE-UHFFFAOYSA-N n-[3-(2-ethoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CCOC1=CC=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O FOAWJAYNKAANKE-UHFFFAOYSA-N 0.000 claims description 2
- SMKHTFVESRLGHO-UHFFFAOYSA-N n-[3-(2-fluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC=CC=3)F)C2=C1 SMKHTFVESRLGHO-UHFFFAOYSA-N 0.000 claims description 2
- CPVUKBOFNWWCSE-UHFFFAOYSA-N n-[3-(2-methoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound COC1=CC=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O CPVUKBOFNWWCSE-UHFFFAOYSA-N 0.000 claims description 2
- DRWVAUBIGFVVMW-UHFFFAOYSA-N n-[3-(2-methylsulfanylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CSC1=CC=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O DRWVAUBIGFVVMW-UHFFFAOYSA-N 0.000 claims description 2
- BGKQTLKBCDFZKF-UHFFFAOYSA-N n-[3-(3,4-dichlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(Cl)C(Cl)=CC=3)C2=C1 BGKQTLKBCDFZKF-UHFFFAOYSA-N 0.000 claims description 2
- HDBSRDZTTSIXIP-UHFFFAOYSA-N n-[3-(3,4-difluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(F)C(F)=CC=3)C2=C1 HDBSRDZTTSIXIP-UHFFFAOYSA-N 0.000 claims description 2
- SUXDTEGXADFEQM-UHFFFAOYSA-N n-[3-(3,4-dimethoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O SUXDTEGXADFEQM-UHFFFAOYSA-N 0.000 claims description 2
- ONUUMGWRZNISBW-UHFFFAOYSA-N n-[3-(3,4-dimethylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C(C)C(C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O ONUUMGWRZNISBW-UHFFFAOYSA-N 0.000 claims description 2
- LQIMQNSGGIKOLD-UHFFFAOYSA-N n-[3-(3,5-dibromophenyl)-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=C(Br)C=3)C2=C1 LQIMQNSGGIKOLD-UHFFFAOYSA-N 0.000 claims description 2
- YZVWRZCVYIMXAQ-UHFFFAOYSA-N n-[3-(3,5-dichlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(Cl)C=C(Cl)C=3)C2=C1 YZVWRZCVYIMXAQ-UHFFFAOYSA-N 0.000 claims description 2
- NPGAKZNWLQYIBR-UHFFFAOYSA-N n-[3-(3,5-difluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(F)C=C(F)C=3)C2=C1 NPGAKZNWLQYIBR-UHFFFAOYSA-N 0.000 claims description 2
- XADFFBXSZLKBNH-UHFFFAOYSA-N n-[3-(3,5-dimethylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 XADFFBXSZLKBNH-UHFFFAOYSA-N 0.000 claims description 2
- JBINBXKUSLUOMD-UHFFFAOYSA-N n-[3-(3-amino-4-methylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C(N)C(C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O JBINBXKUSLUOMD-UHFFFAOYSA-N 0.000 claims description 2
- OMIYKMMBVIXKHL-UHFFFAOYSA-N n-[3-(3-chloro-4-fluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(Cl)C(F)=CC=3)C2=C1 OMIYKMMBVIXKHL-UHFFFAOYSA-N 0.000 claims description 2
- QEGXBKGEGHWADH-UHFFFAOYSA-N n-[3-(3-chlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(Cl)C=CC=3)C2=C1 QEGXBKGEGHWADH-UHFFFAOYSA-N 0.000 claims description 2
- TZZUSSGJZPHVNK-UHFFFAOYSA-N n-[3-(3-ethoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CCOC1=CC=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 TZZUSSGJZPHVNK-UHFFFAOYSA-N 0.000 claims description 2
- YACPJGJIMXFDCL-UHFFFAOYSA-N n-[3-(3-fluoro-4-methylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C(F)C(C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O YACPJGJIMXFDCL-UHFFFAOYSA-N 0.000 claims description 2
- WZFXZBMHETWPTR-UHFFFAOYSA-N n-[3-(3-fluoro-4-phenylmethoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(F)C(OCC=4C=CC=CC=4)=CC=3)C2=C1 WZFXZBMHETWPTR-UHFFFAOYSA-N 0.000 claims description 2
- OAYZGFLQGYKHCY-UHFFFAOYSA-N n-[3-(3-fluoro-4-phenylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(F)C(=CC=3)C=3C=CC=CC=3)C2=C1 OAYZGFLQGYKHCY-UHFFFAOYSA-N 0.000 claims description 2
- HTCQLMOFRKPKNH-UHFFFAOYSA-N n-[3-(3-fluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(F)C=CC=3)C2=C1 HTCQLMOFRKPKNH-UHFFFAOYSA-N 0.000 claims description 2
- GEAMSRBTHPOHNR-UHFFFAOYSA-N n-[3-(3-hydroxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(O)C=CC=3)C2=C1 GEAMSRBTHPOHNR-UHFFFAOYSA-N 0.000 claims description 2
- QSSHFLOHMTUJSF-UHFFFAOYSA-N n-[3-(3-methoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound COC1=CC=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 QSSHFLOHMTUJSF-UHFFFAOYSA-N 0.000 claims description 2
- OGRWMAOQGQIXJV-UHFFFAOYSA-N n-[3-(3-methylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CC1=CC=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 OGRWMAOQGQIXJV-UHFFFAOYSA-N 0.000 claims description 2
- SMJFTRJYUSRUOW-UHFFFAOYSA-N n-[3-(4-acetylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(C(=O)C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O SMJFTRJYUSRUOW-UHFFFAOYSA-N 0.000 claims description 2
- QFOFSLSNTUGTRG-UHFFFAOYSA-N n-[3-(4-bromo-2-fluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC(Br)=CC=3)F)C2=C1 QFOFSLSNTUGTRG-UHFFFAOYSA-N 0.000 claims description 2
- HKODFKUTKSMUEP-UHFFFAOYSA-N n-[3-(4-bromophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(Br)=CC=3)C2=C1 HKODFKUTKSMUEP-UHFFFAOYSA-N 0.000 claims description 2
- MTDMFUNNGODSRH-UHFFFAOYSA-N n-[3-(4-cyanophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(=CC=3)C#N)C2=C1 MTDMFUNNGODSRH-UHFFFAOYSA-N 0.000 claims description 2
- CYYGWWYXMYBLCX-UHFFFAOYSA-N n-[3-(4-ethenylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(C=C)=CC=3)C2=C1 CYYGWWYXMYBLCX-UHFFFAOYSA-N 0.000 claims description 2
- ISKOFTNXFMOPFL-UHFFFAOYSA-N n-[3-(4-ethoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(OCC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O ISKOFTNXFMOPFL-UHFFFAOYSA-N 0.000 claims description 2
- BUXMPVOERLWGKB-UHFFFAOYSA-N n-[3-(4-ethylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(CC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O BUXMPVOERLWGKB-UHFFFAOYSA-N 0.000 claims description 2
- ZNGWPKMDFWSAAW-UHFFFAOYSA-N n-[3-(4-ethylsulfanylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(SCC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O ZNGWPKMDFWSAAW-UHFFFAOYSA-N 0.000 claims description 2
- BBHBFINEYAASLC-UHFFFAOYSA-N n-[3-(4-fluoro-3-methylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C(F)C(C)=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 BBHBFINEYAASLC-UHFFFAOYSA-N 0.000 claims description 2
- VJQQYRVAFBSLBU-UHFFFAOYSA-N n-[3-(4-iodophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(I)=CC=3)C2=C1 VJQQYRVAFBSLBU-UHFFFAOYSA-N 0.000 claims description 2
- XFFUWSWPUCKWPB-UHFFFAOYSA-N n-[3-(4-methylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O XFFUWSWPUCKWPB-UHFFFAOYSA-N 0.000 claims description 2
- LLVRVDQMPWWGBF-UHFFFAOYSA-N n-[3-(4-methylsulfanylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(SC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O LLVRVDQMPWWGBF-UHFFFAOYSA-N 0.000 claims description 2
- NRJMKBQRMBXALK-UHFFFAOYSA-N n-[3-(4-tert-butylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O NRJMKBQRMBXALK-UHFFFAOYSA-N 0.000 claims description 2
- ITDOJSMVXLAUMO-UHFFFAOYSA-N n-[3-(5-chloro-2-methoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound COC1=CC=C(Cl)C=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O ITDOJSMVXLAUMO-UHFFFAOYSA-N 0.000 claims description 2
- HQMBGNCSEQODPO-UHFFFAOYSA-N n-[3-(5-chlorothiophen-2-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3SC(Cl)=CC=3)C2=C1 HQMBGNCSEQODPO-UHFFFAOYSA-N 0.000 claims description 2
- IFKZYHVPGFGFHB-UHFFFAOYSA-N n-[3-[3,5-bis(trifluoromethyl)phenyl]-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)C2=C1 IFKZYHVPGFGFHB-UHFFFAOYSA-N 0.000 claims description 2
- LCBVNGRMXSDLHL-UHFFFAOYSA-N n-[3-[4-(hydroxymethyl)phenyl]-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(CO)=CC=3)C2=C1 LCBVNGRMXSDLHL-UHFFFAOYSA-N 0.000 claims description 2
- HZMDTNRQCKTTHY-UHFFFAOYSA-N n-[[5-[(3-phenyl-1h-indazol-5-yl)sulfamoyl]thiophen-2-yl]methyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NCC(S1)=CC=C1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 HZMDTNRQCKTTHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims 1
- 208000035269 cancer or benign tumor Diseases 0.000 claims 1
- BIHARHJDKGIJHV-UHFFFAOYSA-N n-[3-(2,3-difluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=C(F)C=CC=3)F)C2=C1 BIHARHJDKGIJHV-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 362
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 310
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 183
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 180
- 239000007787 solid Substances 0.000 description 159
- 230000002829 reductive effect Effects 0.000 description 144
- 239000011541 reaction mixture Substances 0.000 description 142
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 132
- 239000000243 solution Substances 0.000 description 130
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 126
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 117
- 238000002844 melting Methods 0.000 description 112
- 230000008018 melting Effects 0.000 description 112
- 238000004458 analytical method Methods 0.000 description 108
- 239000000203 mixture Substances 0.000 description 105
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 97
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 96
- 239000000047 product Substances 0.000 description 93
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 84
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 78
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 77
- 229910001868 water Inorganic materials 0.000 description 74
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 66
- 239000000741 silica gel Substances 0.000 description 65
- 229910002027 silica gel Inorganic materials 0.000 description 65
- 238000004587 chromatography analysis Methods 0.000 description 64
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 63
- 235000019341 magnesium sulphate Nutrition 0.000 description 63
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 58
- 238000000034 method Methods 0.000 description 55
- 239000012153 distilled water Substances 0.000 description 53
- 239000007864 aqueous solution Substances 0.000 description 49
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 48
- 238000001704 evaporation Methods 0.000 description 43
- 230000008020 evaporation Effects 0.000 description 43
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 42
- 229920006395 saturated elastomer Polymers 0.000 description 42
- 239000003480 eluent Substances 0.000 description 41
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 40
- 230000000694 effects Effects 0.000 description 40
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 40
- 239000012074 organic phase Substances 0.000 description 39
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 39
- 235000017557 sodium bicarbonate Nutrition 0.000 description 36
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 36
- 108010067715 Focal Adhesion Protein-Tyrosine Kinases Proteins 0.000 description 33
- 102000016621 Focal Adhesion Protein-Tyrosine Kinases Human genes 0.000 description 33
- 239000011521 glass Substances 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- 210000004027 cell Anatomy 0.000 description 32
- 239000002245 particle Substances 0.000 description 32
- 238000009835 boiling Methods 0.000 description 31
- 230000005764 inhibitory process Effects 0.000 description 31
- 239000000725 suspension Substances 0.000 description 31
- 239000000284 extract Substances 0.000 description 30
- 150000002513 isocyanates Chemical class 0.000 description 30
- 229910052786 argon Inorganic materials 0.000 description 29
- 239000002585 base Substances 0.000 description 29
- 238000010992 reflux Methods 0.000 description 28
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000002904 solvent Substances 0.000 description 26
- 238000004809 thin layer chromatography Methods 0.000 description 25
- 239000003921 oil Substances 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 23
- 239000000843 powder Substances 0.000 description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- 238000001914 filtration Methods 0.000 description 22
- XPJTUCSESGEMOI-UHFFFAOYSA-N 2-methylsulfonylbenzenesulfonyl chloride Chemical compound CS(=O)(=O)C1=CC=CC=C1S(Cl)(=O)=O XPJTUCSESGEMOI-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000008346 aqueous phase Substances 0.000 description 21
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
- 235000011114 ammonium hydroxide Nutrition 0.000 description 20
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 20
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 description 19
- 239000000758 substrate Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 239000012442 inert solvent Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 16
- HVHBPPHCACXALZ-UHFFFAOYSA-N tert-butyl 3-iodo-5-[(2-methylsulfonylphenyl)sulfonylamino]indazole-1-carboxylate Chemical compound C=1C=C2N(C(=O)OC(C)(C)C)N=C(I)C2=CC=1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O HVHBPPHCACXALZ-UHFFFAOYSA-N 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- 125000006239 protecting group Chemical group 0.000 description 15
- FMBRHXYYTLRWCN-UHFFFAOYSA-N tert-butyl 3-iodo-5-[(2-methylpropan-2-yl)oxycarbonyl-(2-methylsulfonylphenyl)sulfonylamino]indazole-1-carboxylate Chemical compound C=1C=C2N(C(=O)OC(C)(C)C)N=C(I)C2=CC=1N(C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CC=C1S(C)(=O)=O FMBRHXYYTLRWCN-UHFFFAOYSA-N 0.000 description 15
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- 238000001556 precipitation Methods 0.000 description 14
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 14
- 102000004190 Enzymes Human genes 0.000 description 13
- 108090000790 Enzymes Proteins 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 230000002378 acidificating effect Effects 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- 229940088598 enzyme Drugs 0.000 description 13
- 239000006260 foam Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 12
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 12
- 230000002401 inhibitory effect Effects 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 108090000623 proteins and genes Proteins 0.000 description 12
- MOBJHQPTGMYKCJ-UHFFFAOYSA-N 3-phenyl-1h-indazol-5-amine Chemical compound C12=CC(N)=CC=C2NN=C1C1=CC=CC=C1 MOBJHQPTGMYKCJ-UHFFFAOYSA-N 0.000 description 11
- 230000035578 autophosphorylation Effects 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 10
- OKYSUJVCDXZGKE-UHFFFAOYSA-N 3-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(S(Cl)(=O)=O)=C1 OKYSUJVCDXZGKE-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 230000014509 gene expression Effects 0.000 description 10
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 10
- 239000003643 water by type Substances 0.000 description 10
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000872 buffer Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 230000004663 cell proliferation Effects 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 102000004169 proteins and genes Human genes 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- HORRIHWEYDDYST-UHFFFAOYSA-N 3-iodo-2h-indazol-5-amine Chemical compound NC1=CC=C2NN=C(I)C2=C1 HORRIHWEYDDYST-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000006071 cream Substances 0.000 description 8
- 239000011790 ferrous sulphate Substances 0.000 description 8
- 235000003891 ferrous sulphate Nutrition 0.000 description 8
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 8
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 8
- 108090000765 processed proteins & peptides Proteins 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 102000001253 Protein Kinase Human genes 0.000 description 7
- SVIBPSNFXYUOFT-UHFFFAOYSA-N [1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic acid Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C(B(O)O)=CC2=C1 SVIBPSNFXYUOFT-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000000338 in vitro Methods 0.000 description 7
- 230000026731 phosphorylation Effects 0.000 description 7
- 238000006366 phosphorylation reaction Methods 0.000 description 7
- 108060006633 protein kinase Proteins 0.000 description 7
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 102000005720 Glutathione transferase Human genes 0.000 description 6
- 108010070675 Glutathione transferase Proteins 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 6
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 6
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 239000012300 argon atmosphere Substances 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 6
- 230000012292 cell migration Effects 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000011534 incubation Methods 0.000 description 6
- 229910001629 magnesium chloride Inorganic materials 0.000 description 6
- 238000011160 research Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- XBTOSRUBOXQWBO-UHFFFAOYSA-N 1h-indazol-5-amine Chemical compound NC1=CC=C2NN=CC2=C1 XBTOSRUBOXQWBO-UHFFFAOYSA-N 0.000 description 5
- GHFKCBWRZWDFKB-UHFFFAOYSA-N 1h-indazole-3,5-diamine Chemical compound C1=C(N)C=C2C(N)=NNC2=C1 GHFKCBWRZWDFKB-UHFFFAOYSA-N 0.000 description 5
- FZCSXBWXWJTUAB-UHFFFAOYSA-N 3-phenylsulfanyl-1-(2-trimethylsilylethoxymethyl)indazol-5-amine Chemical compound C12=CC(N)=CC=C2N(COCC[Si](C)(C)C)N=C1SC1=CC=CC=C1 FZCSXBWXWJTUAB-UHFFFAOYSA-N 0.000 description 5
- SWZRTDLKPZAFDT-UHFFFAOYSA-N 5-nitro-1h-indazol-3-amine Chemical compound C1=C([N+]([O-])=O)C=C2C(N)=NNC2=C1 SWZRTDLKPZAFDT-UHFFFAOYSA-N 0.000 description 5
- 206010006187 Breast cancer Diseases 0.000 description 5
- 208000026310 Breast neoplasm Diseases 0.000 description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 5
- 230000003213 activating effect Effects 0.000 description 5
- 238000010640 amide synthesis reaction Methods 0.000 description 5
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 5
- 238000010511 deprotection reaction Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000002198 insoluble material Substances 0.000 description 5
- OZHTVEXSAHDWFU-UHFFFAOYSA-N n-(3-iodo-2h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2I)C2=C1 OZHTVEXSAHDWFU-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- 238000010647 peptide synthesis reaction Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- CXGODNRKGDPRKB-UHFFFAOYSA-N tert-butyl 5-amino-3-methylindazole-1-carboxylate Chemical compound C1=C(N)C=C2C(C)=NN(C(=O)OC(C)(C)C)C2=C1 CXGODNRKGDPRKB-UHFFFAOYSA-N 0.000 description 5
- 210000004881 tumor cell Anatomy 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
- DIORQIPSPIBCFI-UHFFFAOYSA-N 2-[[3-(1H-benzimidazol-2-yl)-5-nitroindazol-1-yl]methoxy]ethyl-trimethylsilane Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(COCC[Si](C)(C)C)N=C1C1=NC2=CC=CC=C2N1 DIORQIPSPIBCFI-UHFFFAOYSA-N 0.000 description 4
- CXLAMAWMZAQBKK-UHFFFAOYSA-N 3-chloro-2h-indazol-5-amine Chemical compound NC1=CC=C2NN=C(Cl)C2=C1 CXLAMAWMZAQBKK-UHFFFAOYSA-N 0.000 description 4
- KGEYZMRZVKMQBY-UHFFFAOYSA-N 5-amino-1h-indazole-3-carbonitrile Chemical compound NC1=CC=C2NN=C(C#N)C2=C1 KGEYZMRZVKMQBY-UHFFFAOYSA-N 0.000 description 4
- 108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 description 4
- 206010029113 Neovascularisation Diseases 0.000 description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 4
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 4
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000002512 chemotherapy Methods 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- GWQVMPWSEVRGPY-UHFFFAOYSA-N europium cryptate Chemical compound [Eu+3].N=1C2=CC=CC=1CN(CC=1N=C(C=CC=1)C=1N=C(C3)C=CC=1)CC(N=1)=CC(C(=O)NCCN)=CC=1C(N=1)=CC(C(=O)NCCN)=CC=1CN3CC1=CC=CC2=N1 GWQVMPWSEVRGPY-UHFFFAOYSA-N 0.000 description 4
- 239000013604 expression vector Substances 0.000 description 4
- 235000012907 honey Nutrition 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- DIDJZJDDXQPTLN-UHFFFAOYSA-N indazole-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)N=CC2=C1 DIDJZJDDXQPTLN-UHFFFAOYSA-N 0.000 description 4
- 229940043355 kinase inhibitor Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- CHOKQRLURDXUPQ-MDZDMXLPSA-N methyl (e)-3-[5-[(2-methylsulfonylphenyl)sulfonylamino]-2h-indazol-3-yl]prop-2-enoate Chemical compound C1=C2C(/C=C/C(=O)OC)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O CHOKQRLURDXUPQ-MDZDMXLPSA-N 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 230000002018 overexpression Effects 0.000 description 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 241000701447 unidentified baculovirus Species 0.000 description 4
- BKGXBMVBCKGLGG-UHFFFAOYSA-N (1-acetylindazol-5-yl) 3-fluorobenzenesulfonate Chemical compound C=1C=C2N(C(=O)C)N=CC2=CC=1OS(=O)(=O)C1=CC=CC(F)=C1 BKGXBMVBCKGLGG-UHFFFAOYSA-N 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- KNWHCZXVMBGJRE-UHFFFAOYSA-N 1-(5-hydroxyindazol-1-yl)ethanone Chemical compound OC1=CC=C2N(C(=O)C)N=CC2=C1 KNWHCZXVMBGJRE-UHFFFAOYSA-N 0.000 description 3
- USKRVIRQSQMVDV-UHFFFAOYSA-N 1-(5-phenylmethoxyindazol-1-yl)ethanone Chemical compound C=1C=C2N(C(=O)C)N=CC2=CC=1OCC1=CC=CC=C1 USKRVIRQSQMVDV-UHFFFAOYSA-N 0.000 description 3
- BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- YPOQGIJTFIHXMK-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2-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 YPOQGIJTFIHXMK-UHFFFAOYSA-N 0.000 description 3
- TVWSCJHLXNWWMQ-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2-phenylethyl)-1-(2-trimethylsilylethoxymethyl)indazol-5-yl]benzenesulfonamide Chemical compound C12=CC(NS(=O)(=O)C=3C(=CC=CC=3)S(C)(=O)=O)=CC=C2N(COCC[Si](C)(C)C)N=C1CCC1=CC=CC=C1 TVWSCJHLXNWWMQ-UHFFFAOYSA-N 0.000 description 3
- XMXVCQKFFVBCPM-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-phenylsulfanyl-1-(2-trimethylsilylethoxymethyl)indazol-5-yl]benzenesulfonamide Chemical compound C12=CC(NS(=O)(=O)C=3C(=CC=CC=3)S(C)(=O)=O)=CC=C2N(COCC[Si](C)(C)C)N=C1SC1=CC=CC=C1 XMXVCQKFFVBCPM-UHFFFAOYSA-N 0.000 description 3
- NYIBPWGZGSXURD-UHFFFAOYSA-N 3,4-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1Cl NYIBPWGZGSXURD-UHFFFAOYSA-N 0.000 description 3
- ANGMUMISTRUCGF-UHFFFAOYSA-N 3-(1H-benzimidazol-2-yl)-1-(2-trimethylsilylethoxymethyl)indazol-5-amine Chemical compound C12=CC(N)=CC=C2N(COCC[Si](C)(C)C)N=C1C1=NC2=CC=CC=C2N1 ANGMUMISTRUCGF-UHFFFAOYSA-N 0.000 description 3
- BSXPVGDJQOLKMJ-UHFFFAOYSA-N 3-(2-phenylethyl)-1-(2-trimethylsilylethoxymethyl)indazol-5-amine Chemical compound C12=CC(N)=CC=C2N(COCC[Si](C)(C)C)N=C1CCC1=CC=CC=C1 BSXPVGDJQOLKMJ-UHFFFAOYSA-N 0.000 description 3
- BJHMFZLLDMOGMK-UHFFFAOYSA-N 3-(4-chlorophenyl)-1h-indazol-5-amine Chemical compound C12=CC(N)=CC=C2NN=C1C1=CC=C(Cl)C=C1 BJHMFZLLDMOGMK-UHFFFAOYSA-N 0.000 description 3
- NYKDPICRWADIIB-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-nitro-1h-indazole Chemical compound C12=CC([N+](=O)[O-])=CC=C2NN=C1C1=CC=C(Cl)C=C1 NYKDPICRWADIIB-UHFFFAOYSA-N 0.000 description 3
- CKJCACIVGSFXTI-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1h-indazol-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NNC2=CC=C(N)C=C12 CKJCACIVGSFXTI-UHFFFAOYSA-N 0.000 description 3
- UCTRCMYXPOXOSN-UHFFFAOYSA-N 3-iodo-5-nitro-2h-indazole Chemical compound [O-][N+](=O)C1=CC=C2NN=C(I)C2=C1 UCTRCMYXPOXOSN-UHFFFAOYSA-N 0.000 description 3
- ZGDNJFXKELMVLS-UHFFFAOYSA-N 3-methyl-5-nitro-2h-indazole Chemical compound C1=CC([N+]([O-])=O)=CC2=C(C)NN=C21 ZGDNJFXKELMVLS-UHFFFAOYSA-N 0.000 description 3
- WWMGJOLTXIRUQG-UHFFFAOYSA-N 3-n-benzyl-1h-indazole-3,5-diamine Chemical compound C12=CC(N)=CC=C2NN=C1NCC1=CC=CC=C1 WWMGJOLTXIRUQG-UHFFFAOYSA-N 0.000 description 3
- KARXTMOFQRNVKH-UHFFFAOYSA-N 3-n-methyl-1h-indazole-3,5-diamine Chemical compound C1=C(N)C=C2C(NC)=NNC2=C1 KARXTMOFQRNVKH-UHFFFAOYSA-N 0.000 description 3
- APCIZMQSGOFMTI-UHFFFAOYSA-N 4-fluoro-1-methylsulfinyl-2-nitrobenzene Chemical compound CS(=O)C1=CC=C(F)C=C1[N+]([O-])=O APCIZMQSGOFMTI-UHFFFAOYSA-N 0.000 description 3
- DIUCTHUYGZNUJD-UHFFFAOYSA-N 4-fluoro-1-methylsulfonyl-2-nitrobenzene Chemical compound CS(=O)(=O)C1=CC=C(F)C=C1[N+]([O-])=O DIUCTHUYGZNUJD-UHFFFAOYSA-N 0.000 description 3
- XAFHVHYSJZHBMY-UHFFFAOYSA-N 5-amino-1,2-dihydroindazol-3-one Chemical compound NC1=CC=C2NNC(=O)C2=C1 XAFHVHYSJZHBMY-UHFFFAOYSA-N 0.000 description 3
- ZIFCSVSXHXFOAT-UHFFFAOYSA-N 5-amino-1h-indazole-3-carboxylic acid Chemical compound NC1=CC=C2NN=C(C(O)=O)C2=C1 ZIFCSVSXHXFOAT-UHFFFAOYSA-N 0.000 description 3
- XXIHMGJTNOUDFH-UHFFFAOYSA-N 5-amino-n-cyclohexyl-1h-indazole-3-carboxamide Chemical compound C12=CC(N)=CC=C2NN=C1C(=O)NC1CCCCC1 XXIHMGJTNOUDFH-UHFFFAOYSA-N 0.000 description 3
- YNAHBAQYMSEIFX-UHFFFAOYSA-N 5-amino-n-methyl-1h-indazole-3-carboxamide Chemical compound C1=C(N)C=C2C(C(=O)NC)=NNC2=C1 YNAHBAQYMSEIFX-UHFFFAOYSA-N 0.000 description 3
- UBVGOYYYXPTKQU-UHFFFAOYSA-N 5-amino-n-phenyl-1h-indazole-3-carboxamide Chemical compound C12=CC(N)=CC=C2NN=C1C(=O)NC1=CC=CC=C1 UBVGOYYYXPTKQU-UHFFFAOYSA-N 0.000 description 3
- FTVFGNHBSCURJP-UHFFFAOYSA-N 5-fluoro-2-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(F)C=C1N FTVFGNHBSCURJP-UHFFFAOYSA-N 0.000 description 3
- GNLPXSBVPWIRBG-UHFFFAOYSA-N 5-fluoro-2-methylsulfonylbenzenesulfonyl chloride Chemical compound CS(=O)(=O)C1=CC=C(F)C=C1S(Cl)(=O)=O GNLPXSBVPWIRBG-UHFFFAOYSA-N 0.000 description 3
- OXZAZOUXAFCGMY-UHFFFAOYSA-N 5-nitro-1-(2-trimethylsilylethoxymethyl)indazole-3-carboxylic acid Chemical compound [O-][N+](=O)C1=CC=C2N(COCC[Si](C)(C)C)N=C(C(O)=O)C2=C1 OXZAZOUXAFCGMY-UHFFFAOYSA-N 0.000 description 3
- MLTOGNYOQHDCAN-UHFFFAOYSA-N 5-nitro-1h-indazole-3-carboxylic acid Chemical compound C1=C([N+]([O-])=O)C=C2C(C(=O)O)=NNC2=C1 MLTOGNYOQHDCAN-UHFFFAOYSA-N 0.000 description 3
- XTLYDYMVKAGVIN-UHFFFAOYSA-N 5-nitro-3-phenyl-1h-indazole Chemical compound C12=CC([N+](=O)[O-])=CC=C2NN=C1C1=CC=CC=C1 XTLYDYMVKAGVIN-UHFFFAOYSA-N 0.000 description 3
- MTWSGQZRZPUEPP-UHFFFAOYSA-N 6-methyl-5-nitro-3-phenyl-1h-indazole Chemical compound C1=2C=C([N+]([O-])=O)C(C)=CC=2NN=C1C1=CC=CC=C1 MTWSGQZRZPUEPP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 108091007914 CDKs Proteins 0.000 description 3
- 206010009944 Colon cancer Diseases 0.000 description 3
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 3
- 108010091824 Focal Adhesion Kinase 1 Proteins 0.000 description 3
- 101000599951 Homo sapiens Insulin-like growth factor I Proteins 0.000 description 3
- 102100037852 Insulin-like growth factor I Human genes 0.000 description 3
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 3
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 3
- XNONCQOGWPLINT-UHFFFAOYSA-N N-[3-(1H-benzimidazol-2-yl)-1-(2-trimethylsilylethoxymethyl)indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C=1C=C2N(COCC[Si](C)(C)C)N=C(C=3NC4=CC=CC=C4N=3)C2=CC=1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O XNONCQOGWPLINT-UHFFFAOYSA-N 0.000 description 3
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 3
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 3
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 230000006907 apoptotic process Effects 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- WBUBEMULWILOJA-UHFFFAOYSA-N benzyl 4-[(3-phenyl-1h-indazol-5-yl)sulfamoyl]piperidine-1-carboxylate Chemical compound C1CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)CCN1C(=O)OCC1=CC=CC=C1 WBUBEMULWILOJA-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000022131 cell cycle Effects 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000024321 chromosome segregation Effects 0.000 description 3
- 230000001086 cytosolic effect Effects 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 3
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 210000002950 fibroblast Anatomy 0.000 description 3
- 108020001507 fusion proteins Proteins 0.000 description 3
- 102000037865 fusion proteins Human genes 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 108010044426 integrins Proteins 0.000 description 3
- 102000006495 integrins Human genes 0.000 description 3
- 125000002346 iodo group Chemical group I* 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 3
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000011565 manganese chloride Substances 0.000 description 3
- 235000002867 manganese chloride Nutrition 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 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 description 3
- BYHVSDPWMTXMEM-UHFFFAOYSA-N n-(5-amino-1h-indazol-3-yl)benzamide Chemical compound C12=CC(N)=CC=C2NN=C1NC(=O)C1=CC=CC=C1 BYHVSDPWMTXMEM-UHFFFAOYSA-N 0.000 description 3
- DVPBGQDBOJJMSD-UHFFFAOYSA-N n-(5-amino-1h-indazol-3-yl)methanesulfonamide Chemical compound C1=C(N)C=C2C(NS(=O)(=O)C)=NNC2=C1 DVPBGQDBOJJMSD-UHFFFAOYSA-N 0.000 description 3
- VCAAPKZQXYLMFK-UHFFFAOYSA-N n-(5-nitro-1h-indazol-3-yl)benzamide Chemical compound C12=CC([N+](=O)[O-])=CC=C2NN=C1NC(=O)C1=CC=CC=C1 VCAAPKZQXYLMFK-UHFFFAOYSA-N 0.000 description 3
- IURXOVLQTYZZIL-UHFFFAOYSA-N n-(5-nitro-1h-indazol-3-yl)methanesulfonamide Chemical compound C1=C([N+]([O-])=O)C=C2C(NS(=O)(=O)C)=NNC2=C1 IURXOVLQTYZZIL-UHFFFAOYSA-N 0.000 description 3
- FNIDKQFGLADOPA-UHFFFAOYSA-N n-benzyl-5-nitro-1h-indazol-3-amine Chemical compound C12=CC([N+](=O)[O-])=CC=C2NN=C1NCC1=CC=CC=C1 FNIDKQFGLADOPA-UHFFFAOYSA-N 0.000 description 3
- ZICZTZYYEWXJSV-UHFFFAOYSA-N n-cyclohexyl-5-nitro-1h-indazole-3-carboxamide Chemical compound C12=CC([N+](=O)[O-])=CC=C2NN=C1C(=O)NC1CCCCC1 ZICZTZYYEWXJSV-UHFFFAOYSA-N 0.000 description 3
- GCFJXYBSGZNKPT-UHFFFAOYSA-N n-methyl-5-nitro-1h-indazol-3-amine Chemical compound C1=C([N+]([O-])=O)C=C2C(NC)=NNC2=C1 GCFJXYBSGZNKPT-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000008054 signal transmission Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 108010087686 src-Family Kinases Proteins 0.000 description 3
- 102000009076 src-Family Kinases Human genes 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- DENDBJPCNBMXGD-ACCUITESSA-N tert-butyl 3-[(e)-3-methoxy-3-oxoprop-1-enyl]-5-[(2-methylsulfonylphenyl)sulfonylamino]indazole-1-carboxylate Chemical compound C1=C2C(/C=C/C(=O)OC)=NN(C(=O)OC(C)(C)C)C2=CC=C1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O DENDBJPCNBMXGD-ACCUITESSA-N 0.000 description 3
- BFDGBUIWHQNPMU-UHFFFAOYSA-N tert-butyl 3-iodo-5-[(2-methylpropan-2-yl)oxycarbonyl-(2,3,4,5,6-pentafluorophenyl)sulfonylamino]indazole-3-carboxylate Chemical compound C=1C=C2N=NC(I)(C(=O)OC(C)(C)C)C2=CC=1N(C(=O)OC(C)(C)C)S(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F BFDGBUIWHQNPMU-UHFFFAOYSA-N 0.000 description 3
- LFGUPPSISZACCZ-UHFFFAOYSA-N tert-butyl 3-iodo-5-[(2-methylpropan-2-yl)oxycarbonyl-[2-(trifluoromethoxy)phenyl]sulfonylamino]indazole-3-carboxylate Chemical compound C=1C=C2N=NC(I)(C(=O)OC(C)(C)C)C2=CC=1N(C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CC=C1OC(F)(F)F LFGUPPSISZACCZ-UHFFFAOYSA-N 0.000 description 3
- BLIVJDJMJAXBGB-UHFFFAOYSA-N tert-butyl 3-iodo-5-[(2-methylpropan-2-yl)oxycarbonyl-thiophen-2-ylsulfonylamino]indazole-3-carboxylate Chemical compound C=1C=C2N=NC(I)(C(=O)OC(C)(C)C)C2=CC=1N(C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CS1 BLIVJDJMJAXBGB-UHFFFAOYSA-N 0.000 description 3
- WJJRAGPHGJELFV-UHFFFAOYSA-N tert-butyl 3-methyl-5-[(2-methylsulfonylphenyl)sulfonylamino]indazole-1-carboxylate Chemical compound C1=C2C(C)=NN(C(=O)OC(C)(C)C)C2=CC=C1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O WJJRAGPHGJELFV-UHFFFAOYSA-N 0.000 description 3
- KNSRZMXJWFBSQA-UHFFFAOYSA-N tert-butyl 3-methyl-5-nitroindazole-1-carboxylate Chemical compound C1=C([N+]([O-])=O)C=C2C(C)=NN(C(=O)OC(C)(C)C)C2=C1 KNSRZMXJWFBSQA-UHFFFAOYSA-N 0.000 description 3
- KCBGEROLUYJDCR-UHFFFAOYSA-N tert-butyl 5-[(3,4-dichlorophenyl)sulfonylamino]-3-methylindazole-1-carboxylate Chemical compound C1=C2C(C)=NN(C(=O)OC(C)(C)C)C2=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 KCBGEROLUYJDCR-UHFFFAOYSA-N 0.000 description 3
- UEGINHUNYDGNGJ-UHFFFAOYSA-N tert-butyl 5-[(3-fluorophenyl)sulfonyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-iodoindazole-1-carboxylate Chemical compound C=1C=C2N(C(=O)OC(C)(C)C)N=C(I)C2=CC=1N(C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CC(F)=C1 UEGINHUNYDGNGJ-UHFFFAOYSA-N 0.000 description 3
- YLAJWOMNVOQRCJ-UHFFFAOYSA-N tert-butyl 5-[(3-fluorophenyl)sulfonylamino]-3-methylindazole-1-carboxylate Chemical compound C1=C2C(C)=NN(C(=O)OC(C)(C)C)C2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 YLAJWOMNVOQRCJ-UHFFFAOYSA-N 0.000 description 3
- YCYIWCBFFKYTKP-UHFFFAOYSA-N tert-butyl 5-[(3-fluorophenyl)sulfonylamino]-3-phenylindazole-1-carboxylate Chemical compound C12=CC(NS(=O)(=O)C=3C=C(F)C=CC=3)=CC=C2N(C(=O)OC(C)(C)C)N=C1C1=CC=CC=C1 YCYIWCBFFKYTKP-UHFFFAOYSA-N 0.000 description 3
- GVODNOZMDIXTMI-UHFFFAOYSA-N tert-butyl 5-[benzenesulfonyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-iodoindazole-1-carboxylate Chemical compound C=1C=C2N(C(=O)OC(C)(C)C)N=C(I)C2=CC=1N(C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CC=C1 GVODNOZMDIXTMI-UHFFFAOYSA-N 0.000 description 3
- URDVTOKSOBYAHA-UHFFFAOYSA-N tert-butyl 5-amino-3-phenylindazole-1-carboxylate Chemical compound C12=CC(N)=CC=C2N(C(=O)OC(C)(C)C)N=C1C1=CC=CC=C1 URDVTOKSOBYAHA-UHFFFAOYSA-N 0.000 description 3
- NAJCRXIRAAIOAN-UHFFFAOYSA-N tert-butyl 5-nitro-3-phenylindazole-1-carboxylate Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C(=O)OC(C)(C)C)N=C1C1=CC=CC=C1 NAJCRXIRAAIOAN-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- IIWJLEGVACLVBU-UHFFFAOYSA-N trimethyl-[2-[(5-nitro-3-phenylsulfanylindazol-1-yl)methoxy]ethyl]silane Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(COCC[Si](C)(C)C)N=C1SC1=CC=CC=C1 IIWJLEGVACLVBU-UHFFFAOYSA-N 0.000 description 3
- FFJQDVCAIYZKHA-UHFFFAOYSA-N trimethyl-[2-[[5-nitro-3-(2-phenylethynyl)indazol-1-yl]methoxy]ethyl]silane Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(COCC[Si](C)(C)C)N=C1C#CC1=CC=CC=C1 FFJQDVCAIYZKHA-UHFFFAOYSA-N 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- UZKBAGUNURYRQE-UHFFFAOYSA-N (2-chloro-5-nitrophenyl)-(4-chlorophenyl)methanone Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C(=O)C=2C=CC(Cl)=CC=2)=C1 UZKBAGUNURYRQE-UHFFFAOYSA-N 0.000 description 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 description 2
- ZWVYQZBCSXCUOO-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenesulfonamide Chemical class NS(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F ZWVYQZBCSXCUOO-UHFFFAOYSA-N 0.000 description 2
- OWZRMMLTVVGUPW-UHFFFAOYSA-N 2-[(3-iodo-5-nitroindazol-1-yl)methoxy]ethyl-trimethylsilane Chemical compound [O-][N+](=O)C1=CC=C2N(COCC[Si](C)(C)C)N=C(I)C2=C1 OWZRMMLTVVGUPW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- YMZVPMQBIGSBOW-UHFFFAOYSA-N 2-methyl-4-phenylmethoxyaniline Chemical compound C1=C(N)C(C)=CC(OCC=2C=CC=CC=2)=C1 YMZVPMQBIGSBOW-UHFFFAOYSA-N 0.000 description 2
- GVPTWTKNUYXCQX-UHFFFAOYSA-N 3-(1H-benzimidazol-2-yl)-1H-indazol-5-ol Chemical compound C1=CC=C2NC(C3=NNC4=CC=C(C=C43)O)=NC2=C1 GVPTWTKNUYXCQX-UHFFFAOYSA-N 0.000 description 2
- WAMFQXZDXAPTPE-UHFFFAOYSA-N 3-(2-phenylethynyl)-1-(2-trimethylsilylethoxymethyl)indazol-5-amine Chemical compound C12=CC(N)=CC=C2N(COCC[Si](C)(C)C)N=C1C#CC1=CC=CC=C1 WAMFQXZDXAPTPE-UHFFFAOYSA-N 0.000 description 2
- AGZGTCUSGGVSFV-UHFFFAOYSA-N 3-(4-fluorophenyl)-1h-indazol-5-amine Chemical compound C12=CC(N)=CC=C2NN=C1C1=CC=C(F)C=C1 AGZGTCUSGGVSFV-UHFFFAOYSA-N 0.000 description 2
- AOKHRTSXJINPPJ-UHFFFAOYSA-N 3-bromo-2h-indazol-5-amine Chemical compound C1=C(N)C=CC2=NNC(Br)=C21 AOKHRTSXJINPPJ-UHFFFAOYSA-N 0.000 description 2
- SFOTVLKIYVFVPN-UHFFFAOYSA-N 4-(dimethylamino)-2,3,5,6-tetrafluoro-N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound FC1=C(F)C(N(C)C)=C(F)C(F)=C1S(=O)(=O)NC1=CC=C(NN=C2C=3NC4=CC=CC=C4C=3)C2=C1 SFOTVLKIYVFVPN-UHFFFAOYSA-N 0.000 description 2
- GFZWLZQOZGNKDW-UHFFFAOYSA-N 4-fluoro-1-methylsulfanyl-2-nitrobenzene Chemical compound CSC1=CC=C(F)C=C1[N+]([O-])=O GFZWLZQOZGNKDW-UHFFFAOYSA-N 0.000 description 2
- URLYIPCFQVDOEZ-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfonylamino]-1h-indazole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 URLYIPCFQVDOEZ-UHFFFAOYSA-N 0.000 description 2
- JTZWISIFAPIBCT-UHFFFAOYSA-N 5-nitro-1-(2-trimethylsilylethoxymethyl)indazole-3-carbaldehyde Chemical compound [O-][N+](=O)C1=CC=C2N(COCC[Si](C)(C)C)N=C(C=O)C2=C1 JTZWISIFAPIBCT-UHFFFAOYSA-N 0.000 description 2
- WXTZAAHDBOKXDI-UHFFFAOYSA-N 5-nitro-1h-indazole-3-carbonitrile Chemical compound [O-][N+](=O)C1=CC=C2NN=C(C#N)C2=C1 WXTZAAHDBOKXDI-UHFFFAOYSA-N 0.000 description 2
- HMMPHXCOTBASBC-UHFFFAOYSA-N 6-methyl-1h-indazole Chemical compound CC1=CC=C2C=NNC2=C1 HMMPHXCOTBASBC-UHFFFAOYSA-N 0.000 description 2
- OEBYMRZSEMWCPS-UHFFFAOYSA-N 6-methyl-3-phenyl-1h-indazol-5-amine Chemical compound C1=2C=C(N)C(C)=CC=2NN=C1C1=CC=CC=C1 OEBYMRZSEMWCPS-UHFFFAOYSA-N 0.000 description 2
- PMYDCSGPFKERNG-UHFFFAOYSA-N 6-methyl-3-phenyl-1h-indazole Chemical compound N=1NC2=CC(C)=CC=C2C=1C1=CC=CC=C1 PMYDCSGPFKERNG-UHFFFAOYSA-N 0.000 description 2
- 102000009088 Angiopoietin-1 Human genes 0.000 description 2
- 108010048154 Angiopoietin-1 Proteins 0.000 description 2
- 102100034608 Angiopoietin-2 Human genes 0.000 description 2
- 206010003571 Astrocytoma Diseases 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- 102000018691 Focal Adhesion Kinase 1 Human genes 0.000 description 2
- 230000010190 G1 phase Effects 0.000 description 2
- 230000004707 G1/S transition Effects 0.000 description 2
- DHCLVCXQIBBOPH-UHFFFAOYSA-N Glycerol 2-phosphate Chemical compound OCC(CO)OP(O)(O)=O DHCLVCXQIBBOPH-UHFFFAOYSA-N 0.000 description 2
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 241000721701 Lynx Species 0.000 description 2
- 239000007993 MOPS buffer Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229910003204 NH2 Inorganic materials 0.000 description 2
- 229910020700 Na3VO4 Inorganic materials 0.000 description 2
- 108700020796 Oncogene Proteins 0.000 description 2
- 102000043276 Oncogene Human genes 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 206010060862 Prostate cancer Diseases 0.000 description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 2
- 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 description 2
- 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 description 2
- 230000018199 S phase Effects 0.000 description 2
- 108050003452 SH2 domains Proteins 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 108010090804 Streptavidin Proteins 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 108091023040 Transcription factor Proteins 0.000 description 2
- 102000040945 Transcription factor Human genes 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- WZPOUEKWKYVQMH-UHFFFAOYSA-N [1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolo[2,3-b]pyridin-2-yl]boronic acid Chemical compound C1=CN=C2N(C(=O)OC(C)(C)C)C(B(O)O)=CC2=C1 WZPOUEKWKYVQMH-UHFFFAOYSA-N 0.000 description 2
- KKUSHICTVDIAKS-UHFFFAOYSA-N [5-methoxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolo[2,3-b]pyridin-2-yl]boronic acid Chemical compound COC1=CN=C2N(C(=O)OC(C)(C)C)C(B(O)O)=CC2=C1 KKUSHICTVDIAKS-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000002491 angiogenic effect Effects 0.000 description 2
- 230000001028 anti-proliverative effect Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000005441 aurora Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- HEGCWAOVTPVFBJ-UHFFFAOYSA-N benzyl 4-chlorosulfonylpiperidine-1-carboxylate Chemical compound C1CC(S(=O)(=O)Cl)CCN1C(=O)OCC1=CC=CC=C1 HEGCWAOVTPVFBJ-UHFFFAOYSA-N 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000005620 boronic acid group Chemical class 0.000 description 2
- 230000021164 cell adhesion Effects 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- 239000002299 complementary DNA Substances 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- MJWVCJUSRGLHFO-UHFFFAOYSA-N cyclohexanesulfonyl chloride Chemical compound ClS(=O)(=O)C1CCCCC1 MJWVCJUSRGLHFO-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 229960000684 cytarabine Drugs 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
- 238000002868 homogeneous time resolved fluorescence Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 230000026045 iodination Effects 0.000 description 2
- 238000006192 iodination reaction Methods 0.000 description 2
- 229910000358 iron sulfate Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 201000005202 lung cancer Diseases 0.000 description 2
- 208000020816 lung neoplasm Diseases 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 2
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 2
- 230000001613 neoplastic effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000001959 radiotherapy Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 230000019491 signal transduction Effects 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- KBAVLSAJSYZNDY-UHFFFAOYSA-M sodium;5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazole-3-carboxylate Chemical compound [Na+].CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C([O-])=O)C2=C1 KBAVLSAJSYZNDY-UHFFFAOYSA-M 0.000 description 2
- 238000000935 solvent evaporation Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
- 239000012414 tert-butyl nitrite Substances 0.000 description 2
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000001131 transforming effect Effects 0.000 description 2
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 2
- 230000004614 tumor growth Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 description 1
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 1
- ZKVYRAMVXZRYHM-UHFFFAOYSA-N (2-methylsulfonylphenyl) 3-(methylcarbamoyl)-1h-indazole-5-sulfonate Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1S(=O)(=O)OC1=CC=CC=C1S(C)(=O)=O ZKVYRAMVXZRYHM-UHFFFAOYSA-N 0.000 description 1
- QYIICACSZCMVJK-UHFFFAOYSA-N (2-methylsulfonylphenyl) 3-(phenylcarbamoyl)-1h-indazole-5-sulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1OS(=O)(=O)C1=CC=C(NN=C2C(=O)NC=3C=CC=CC=3)C2=C1 QYIICACSZCMVJK-UHFFFAOYSA-N 0.000 description 1
- HJAHYIZGOYXBIN-UHFFFAOYSA-N (2-methylsulfonylphenyl) 3-benzamido-1h-indazole-5-sulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1OS(=O)(=O)C1=CC=C(NN=C2NC(=O)C=3C=CC=CC=3)C2=C1 HJAHYIZGOYXBIN-UHFFFAOYSA-N 0.000 description 1
- BLCPRBJDXRVWQM-UHFFFAOYSA-N (2-methylsulfonylphenyl) 3-carbamoyl-1h-indazole-5-sulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1OS(=O)(=O)C1=CC=C(NN=C2C(N)=O)C2=C1 BLCPRBJDXRVWQM-UHFFFAOYSA-N 0.000 description 1
- BQXBCLZMBBFZCF-UHFFFAOYSA-N (2-methylsulfonylphenyl) 3-chloro-2h-indazole-5-sulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1OS(=O)(=O)C1=CC2=C(Cl)NN=C2C=C1 BQXBCLZMBBFZCF-UHFFFAOYSA-N 0.000 description 1
- KPLXBUUQLOMSGM-UHFFFAOYSA-N (2-methylsulfonylphenyl) 3-cyano-1h-indazole-5-sulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1OS(=O)(=O)C1=CC=C(NN=C2C#N)C2=C1 KPLXBUUQLOMSGM-UHFFFAOYSA-N 0.000 description 1
- OKIAITIBKJEVFJ-UHFFFAOYSA-N (2-methylsulfonylphenyl) 3-iodo-2h-indazole-5-sulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1OS(=O)(=O)C1=CC2=C(I)NN=C2C=C1 OKIAITIBKJEVFJ-UHFFFAOYSA-N 0.000 description 1
- WVXMQATYXBWEAO-UHFFFAOYSA-N (2-methylsulfonylphenyl) 3-methyl-2h-indazole-5-sulfonate Chemical compound C=1C2=C(C)NN=C2C=CC=1S(=O)(=O)OC1=CC=CC=C1S(C)(=O)=O WVXMQATYXBWEAO-UHFFFAOYSA-N 0.000 description 1
- MAIZCICTEPUVSR-UHFFFAOYSA-N (2-methylsulfonylphenyl) 3-oxo-1,2-dihydroindazole-5-sulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1OS(=O)(=O)C1=CC=C(NNC2=O)C2=C1 MAIZCICTEPUVSR-UHFFFAOYSA-N 0.000 description 1
- VYTBZZYJOFFPGR-UHFFFAOYSA-N (2-methylsulfonylphenyl) 3-phenyl-1h-indazole-5-sulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1OS(=O)(=O)C1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 VYTBZZYJOFFPGR-UHFFFAOYSA-N 0.000 description 1
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 1
- NAUJAQAXMHAJFN-UHFFFAOYSA-N (3,4-dichlorophenyl) 3-(methylcarbamoyl)-1h-indazole-5-sulfonate Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1S(=O)(=O)OC1=CC=C(Cl)C(Cl)=C1 NAUJAQAXMHAJFN-UHFFFAOYSA-N 0.000 description 1
- MKZKCVBELSIMQO-UHFFFAOYSA-N (3,4-dichlorophenyl) 3-(phenylcarbamoyl)-1h-indazole-5-sulfonate Chemical compound C1=C(Cl)C(Cl)=CC=C1OS(=O)(=O)C1=CC=C(NN=C2C(=O)NC=3C=CC=CC=3)C2=C1 MKZKCVBELSIMQO-UHFFFAOYSA-N 0.000 description 1
- WXRVHQACFMNLFZ-UHFFFAOYSA-N (3,4-dichlorophenyl) 3-benzamido-1h-indazole-5-sulfonate Chemical compound C1=C(Cl)C(Cl)=CC=C1OS(=O)(=O)C1=CC=C(NN=C2NC(=O)C=3C=CC=CC=3)C2=C1 WXRVHQACFMNLFZ-UHFFFAOYSA-N 0.000 description 1
- JJUWJRJYDZKQGW-UHFFFAOYSA-N (3,4-dichlorophenyl) 3-carbamoyl-1h-indazole-5-sulfonate Chemical compound C1=C2C(C(=O)N)=NNC2=CC=C1S(=O)(=O)OC1=CC=C(Cl)C(Cl)=C1 JJUWJRJYDZKQGW-UHFFFAOYSA-N 0.000 description 1
- RBTYQJXSZSJHJE-UHFFFAOYSA-N (3,4-dichlorophenyl) 3-chloro-2h-indazole-5-sulfonate Chemical compound C=1C2=C(Cl)NN=C2C=CC=1S(=O)(=O)OC1=CC=C(Cl)C(Cl)=C1 RBTYQJXSZSJHJE-UHFFFAOYSA-N 0.000 description 1
- KORVNWYSWKSCCM-UHFFFAOYSA-N (3,4-dichlorophenyl) 3-cyano-1h-indazole-5-sulfonate Chemical compound C1=C(Cl)C(Cl)=CC=C1OS(=O)(=O)C1=CC=C(NN=C2C#N)C2=C1 KORVNWYSWKSCCM-UHFFFAOYSA-N 0.000 description 1
- MYMGXDJHVUCMEB-UHFFFAOYSA-N (3,4-dichlorophenyl) 3-methyl-2h-indazole-5-sulfonate Chemical compound C=1C2=C(C)NN=C2C=CC=1S(=O)(=O)OC1=CC=C(Cl)C(Cl)=C1 MYMGXDJHVUCMEB-UHFFFAOYSA-N 0.000 description 1
- LOYGVNWWWDFJEV-UHFFFAOYSA-N (3,4-dichlorophenyl) 3-oxo-1,2-dihydroindazole-5-sulfonate Chemical compound C1=C(Cl)C(Cl)=CC=C1OS(=O)(=O)C1=CC=C(NNC2=O)C2=C1 LOYGVNWWWDFJEV-UHFFFAOYSA-N 0.000 description 1
- ZQGOOEBJTFNJFE-UHFFFAOYSA-N (3,4-dichlorophenyl) 3-phenyl-1h-indazole-5-sulfonate Chemical compound C1=C(Cl)C(Cl)=CC=C1OS(=O)(=O)C1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 ZQGOOEBJTFNJFE-UHFFFAOYSA-N 0.000 description 1
- QFXOPAKBUFBMJF-UHFFFAOYSA-N (3-benzamido-1h-indazol-5-yl) 2-methylsulfonylbenzenesulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)OC1=CC=C(NN=C2NC(=O)C=3C=CC=CC=3)C2=C1 QFXOPAKBUFBMJF-UHFFFAOYSA-N 0.000 description 1
- OFVCDTLWRRGKTJ-UHFFFAOYSA-N (3-benzamido-1h-indazol-5-yl) 3,4-dichlorobenzenesulfonate Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)OC1=CC=C(NN=C2NC(=O)C=3C=CC=CC=3)C2=C1 OFVCDTLWRRGKTJ-UHFFFAOYSA-N 0.000 description 1
- FGYCOGBDHUFJQE-UHFFFAOYSA-N (3-benzamido-1h-indazol-5-yl) 3-fluorobenzenesulfonate Chemical compound FC1=CC=CC(S(=O)(=O)OC=2C=C3C(NC(=O)C=4C=CC=CC=4)=NNC3=CC=2)=C1 FGYCOGBDHUFJQE-UHFFFAOYSA-N 0.000 description 1
- AFSSVCNPDKKSRR-UHFFFAOYSA-N (3-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Br)=C1 AFSSVCNPDKKSRR-UHFFFAOYSA-N 0.000 description 1
- UXTXUEYLIAZIEI-UHFFFAOYSA-N (3-carbamoyl-1h-indazol-5-yl) 2-methylsulfonylbenzenesulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)OC1=CC=C(NN=C2C(N)=O)C2=C1 UXTXUEYLIAZIEI-UHFFFAOYSA-N 0.000 description 1
- SZHDCDJTYKDRQV-UHFFFAOYSA-N (3-carbamoyl-1h-indazol-5-yl) 3,4-dichlorobenzenesulfonate Chemical compound C1=C2C(C(=O)N)=NNC2=CC=C1OS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 SZHDCDJTYKDRQV-UHFFFAOYSA-N 0.000 description 1
- MNSDNWOURMJFFE-UHFFFAOYSA-N (3-carbamoyl-1h-indazol-5-yl) 3-fluorobenzenesulfonate Chemical compound C1=C2C(C(=O)N)=NNC2=CC=C1OS(=O)(=O)C1=CC=CC(F)=C1 MNSDNWOURMJFFE-UHFFFAOYSA-N 0.000 description 1
- FMSIDUXIOWBIEN-UHFFFAOYSA-N (3-chloro-2h-indazol-5-yl) 2-methylsulfonylbenzenesulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)OC1=CC=C(NN=C2Cl)C2=C1 FMSIDUXIOWBIEN-UHFFFAOYSA-N 0.000 description 1
- HJHYWOSFWGIWSX-UHFFFAOYSA-N (3-chloro-2h-indazol-5-yl) 3,4-dichlorobenzenesulfonate Chemical compound C1=C2C(Cl)=NNC2=CC=C1OS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 HJHYWOSFWGIWSX-UHFFFAOYSA-N 0.000 description 1
- YQKMLWHDYYXXTN-UHFFFAOYSA-N (3-chloro-2h-indazol-5-yl) 3-fluorobenzenesulfonate Chemical compound FC1=CC=CC(S(=O)(=O)OC=2C=C3C(Cl)=NNC3=CC=2)=C1 YQKMLWHDYYXXTN-UHFFFAOYSA-N 0.000 description 1
- MGHRHGMXQJWOSU-UHFFFAOYSA-N (3-cyano-1h-indazol-5-yl) 2-methylsulfonylbenzenesulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)OC1=CC=C(NN=C2C#N)C2=C1 MGHRHGMXQJWOSU-UHFFFAOYSA-N 0.000 description 1
- WYNLVFYNEWBPGJ-UHFFFAOYSA-N (3-cyano-1h-indazol-5-yl) 3,4-dichlorobenzenesulfonate Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)OC1=CC=C(NN=C2C#N)C2=C1 WYNLVFYNEWBPGJ-UHFFFAOYSA-N 0.000 description 1
- NPPXXDAZMDIBKE-UHFFFAOYSA-N (3-cyano-1h-indazol-5-yl) 3-fluorobenzenesulfonate Chemical compound FC1=CC=CC(S(=O)(=O)OC=2C=C3C(C#N)=NNC3=CC=2)=C1 NPPXXDAZMDIBKE-UHFFFAOYSA-N 0.000 description 1
- XDBHWPLGGBLUHH-UHFFFAOYSA-N (3-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C#N)=C1 XDBHWPLGGBLUHH-UHFFFAOYSA-N 0.000 description 1
- FYCQYEPSONCEHU-UHFFFAOYSA-N (3-fluorophenyl) 3-(methylcarbamoyl)-1h-indazole-5-sulfonate Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1S(=O)(=O)OC1=CC=CC(F)=C1 FYCQYEPSONCEHU-UHFFFAOYSA-N 0.000 description 1
- MEQYVVLIRVFVIA-UHFFFAOYSA-N (3-fluorophenyl) 3-(phenylcarbamoyl)-1h-indazole-5-sulfonate Chemical compound FC1=CC=CC(OS(=O)(=O)C=2C=C3C(C(=O)NC=4C=CC=CC=4)=NNC3=CC=2)=C1 MEQYVVLIRVFVIA-UHFFFAOYSA-N 0.000 description 1
- BZFSAUYTSKBJHM-UHFFFAOYSA-N (3-fluorophenyl) 3-benzamido-1h-indazole-5-sulfonate Chemical compound FC1=CC=CC(OS(=O)(=O)C=2C=C3C(NC(=O)C=4C=CC=CC=4)=NNC3=CC=2)=C1 BZFSAUYTSKBJHM-UHFFFAOYSA-N 0.000 description 1
- TWDABOOPSLXMLX-UHFFFAOYSA-N (3-fluorophenyl) 3-carbamoyl-1h-indazole-5-sulfonate Chemical compound C1=C2C(C(=O)N)=NNC2=CC=C1S(=O)(=O)OC1=CC=CC(F)=C1 TWDABOOPSLXMLX-UHFFFAOYSA-N 0.000 description 1
- DENIOBLCBHJHAI-UHFFFAOYSA-N (3-fluorophenyl) 3-chloro-2h-indazole-5-sulfonate Chemical compound FC1=CC=CC(OS(=O)(=O)C2=CC3=C(Cl)NN=C3C=C2)=C1 DENIOBLCBHJHAI-UHFFFAOYSA-N 0.000 description 1
- GQLLNCFRRVCCQP-UHFFFAOYSA-N (3-fluorophenyl) 3-cyano-1h-indazole-5-sulfonate Chemical compound FC1=CC=CC(OS(=O)(=O)C=2C=C3C(C#N)=NNC3=CC=2)=C1 GQLLNCFRRVCCQP-UHFFFAOYSA-N 0.000 description 1
- WUMQZRCVGDMSNI-UHFFFAOYSA-N (3-fluorophenyl) 3-iodo-2h-indazole-5-sulfonate Chemical compound FC1=CC=CC(OS(=O)(=O)C2=CC3=C(I)NN=C3C=C2)=C1 WUMQZRCVGDMSNI-UHFFFAOYSA-N 0.000 description 1
- YSRCVDAQCJNXJL-UHFFFAOYSA-N (3-fluorophenyl) 3-methyl-2h-indazole-5-sulfonate Chemical compound C=1C2=C(C)NN=C2C=CC=1S(=O)(=O)OC1=CC=CC(F)=C1 YSRCVDAQCJNXJL-UHFFFAOYSA-N 0.000 description 1
- OTDOPBBGQYDQCS-UHFFFAOYSA-N (3-fluorophenyl) 3-oxo-1,2-dihydroindazole-5-sulfonate Chemical compound FC1=CC=CC(OS(=O)(=O)C=2C=C3C(=O)NNC3=CC=2)=C1 OTDOPBBGQYDQCS-UHFFFAOYSA-N 0.000 description 1
- XJUDLYCTUIOVTH-UHFFFAOYSA-N (3-fluorophenyl) 3-phenyl-1h-indazole-5-sulfonate Chemical compound FC1=CC=CC(OS(=O)(=O)C=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 XJUDLYCTUIOVTH-UHFFFAOYSA-N 0.000 description 1
- NVMKLAIFPKJIMX-UHFFFAOYSA-N (3-iodo-2h-indazol-5-yl) 2-methylsulfonylbenzenesulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)OC1=CC=C(NN=C2I)C2=C1 NVMKLAIFPKJIMX-UHFFFAOYSA-N 0.000 description 1
- VHZYYXQPLPYEHB-UHFFFAOYSA-N (3-iodo-2h-indazol-5-yl) 3,4-dichlorobenzenesulfonate Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)OC1=CC=C(NN=C2I)C2=C1 VHZYYXQPLPYEHB-UHFFFAOYSA-N 0.000 description 1
- JIGJZGYYUMDXPT-UHFFFAOYSA-N (3-iodo-2h-indazol-5-yl) 3-fluorobenzenesulfonate Chemical compound FC1=CC=CC(S(=O)(=O)OC=2C=C3C(I)=NNC3=CC=2)=C1 JIGJZGYYUMDXPT-UHFFFAOYSA-N 0.000 description 1
- ALTLCJHSJMGSLT-UHFFFAOYSA-N (3-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=CC(B(O)O)=C1 ALTLCJHSJMGSLT-UHFFFAOYSA-N 0.000 description 1
- DJBHMKOOKJVGLV-UHFFFAOYSA-N (3-methyl-2h-indazol-5-yl) 2-methylsulfonylbenzenesulfonate Chemical compound C1=C2C(C)=NNC2=CC=C1OS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O DJBHMKOOKJVGLV-UHFFFAOYSA-N 0.000 description 1
- YDAWRHPGTMMAMM-UHFFFAOYSA-N (3-methyl-2h-indazol-5-yl) 3,4-dichlorobenzenesulfonate Chemical compound C1=C2C(C)=NNC2=CC=C1OS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 YDAWRHPGTMMAMM-UHFFFAOYSA-N 0.000 description 1
- FLBFPSHUCSVRFD-UHFFFAOYSA-N (3-methyl-2h-indazol-5-yl) 3-fluorobenzenesulfonate Chemical compound C1=C2C(C)=NNC2=CC=C1OS(=O)(=O)C1=CC=CC(F)=C1 FLBFPSHUCSVRFD-UHFFFAOYSA-N 0.000 description 1
- XGDGWJWPSBVIEM-UHFFFAOYSA-N (3-oxo-1,2-dihydroindazol-5-yl) 2-methylsulfonylbenzenesulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)OC1=CC=C(NN=C2O)C2=C1 XGDGWJWPSBVIEM-UHFFFAOYSA-N 0.000 description 1
- JYDMSENHNVSKTA-UHFFFAOYSA-N (3-oxo-1,2-dihydroindazol-5-yl) 3,4-dichlorobenzenesulfonate Chemical compound C1=C2C(O)=NNC2=CC=C1OS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 JYDMSENHNVSKTA-UHFFFAOYSA-N 0.000 description 1
- SXHYNDDARYDGPU-UHFFFAOYSA-N (3-oxo-1,2-dihydroindazol-5-yl) 3-fluorobenzenesulfonate Chemical compound C1=C2C(O)=NNC2=CC=C1OS(=O)(=O)C1=CC=CC(F)=C1 SXHYNDDARYDGPU-UHFFFAOYSA-N 0.000 description 1
- GHDCJSLCABLDLN-UHFFFAOYSA-N (3-phenyl-1h-indazol-5-yl) 2-methylsulfonylbenzenesulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)OC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 GHDCJSLCABLDLN-UHFFFAOYSA-N 0.000 description 1
- KORUZCVDNQTTDI-UHFFFAOYSA-N (3-phenyl-1h-indazol-5-yl) 3,4-dichlorobenzenesulfonate Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)OC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 KORUZCVDNQTTDI-UHFFFAOYSA-N 0.000 description 1
- BWEZEJBVLPIOBM-UHFFFAOYSA-N (3-phenyl-1h-indazol-5-yl) 3-fluorobenzenesulfonate Chemical compound FC1=CC=CC(S(=O)(=O)OC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 BWEZEJBVLPIOBM-UHFFFAOYSA-N 0.000 description 1
- PQCXFUXRTRESBD-UHFFFAOYSA-N (4-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=C(B(O)O)C=C1 PQCXFUXRTRESBD-UHFFFAOYSA-N 0.000 description 1
- FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 description 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 1
- PJDWOAACRMHASE-PMUSNMMLSA-N (E)-3-[5-[(2-methylsulfonylphenyl)sulfonylamino]-2H-indazol-3-yl]prop-2-enoic acid trihydrochloride Chemical compound Cl.Cl.Cl.CS(=O)(=O)c1ccccc1S(=O)(=O)Nc1ccc2n[nH]c(\C=C\C(O)=O)c2c1.CS(=O)(=O)c1ccccc1S(=O)(=O)Nc1ccc2n[nH]c(\C=C\C(O)=O)c2c1 PJDWOAACRMHASE-PMUSNMMLSA-N 0.000 description 1
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 1
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical class C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 1
- WIKBZUXHNPONPP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-iodo-2-(trifluoromethyl)propane Chemical compound FC(F)(F)C(I)(C(F)(F)F)C(F)(F)F WIKBZUXHNPONPP-UHFFFAOYSA-N 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- FLCVDDQJGBHDTD-UHFFFAOYSA-N 1-indazol-2-ylbenzimidazole Chemical class C1=C2C=CC=CC2=NN1N1C2=CC=CC=C2N=C1 FLCVDDQJGBHDTD-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- DGHHQBMTXTWTJV-BQAIUKQQSA-N 119413-54-6 Chemical compound Cl.C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 DGHHQBMTXTWTJV-BQAIUKQQSA-N 0.000 description 1
- ZYICAKHXUIQPJK-UHFFFAOYSA-N 1h-indazol-5-yl 2-methylsulfonylbenzenesulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)OC1=CC=C(NN=C2)C2=C1 ZYICAKHXUIQPJK-UHFFFAOYSA-N 0.000 description 1
- WOFLZHIWIMCOHJ-UHFFFAOYSA-N 1h-indazol-5-yl 3,4-dichlorobenzenesulfonate Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)OC1=CC=C(NN=C2)C2=C1 WOFLZHIWIMCOHJ-UHFFFAOYSA-N 0.000 description 1
- OHNCNPVNTFTJLX-UHFFFAOYSA-N 1h-indazole-5-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C2NN=CC2=C1 OHNCNPVNTFTJLX-UHFFFAOYSA-N 0.000 description 1
- USASUEYARBQNBM-UHFFFAOYSA-N 1h-indol-2-ylboronic acid Chemical compound C1=CC=C2NC(B(O)O)=CC2=C1 USASUEYARBQNBM-UHFFFAOYSA-N 0.000 description 1
- UOJCTEGNHXRPKO-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenesulfonyl chloride Chemical compound FC1=C(F)C(F)=C(S(Cl)(=O)=O)C(F)=C1F UOJCTEGNHXRPKO-UHFFFAOYSA-N 0.000 description 1
- PQODWTNHDKDHIW-UHFFFAOYSA-N 2,3-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC(S(Cl)(=O)=O)=C1Cl PQODWTNHDKDHIW-UHFFFAOYSA-N 0.000 description 1
- WGGKQIKICKLWGN-UHFFFAOYSA-N 2,6-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC(Cl)=C1S(Cl)(=O)=O WGGKQIKICKLWGN-UHFFFAOYSA-N 0.000 description 1
- QXWAUQMMMIMLTO-UHFFFAOYSA-N 2,6-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(F)=C1S(Cl)(=O)=O QXWAUQMMMIMLTO-UHFFFAOYSA-N 0.000 description 1
- ZEMZPXWZVTUONV-UHFFFAOYSA-N 2-(2-dicyclohexylphosphanylphenyl)-n,n-dimethylaniline Chemical group CN(C)C1=CC=CC=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 ZEMZPXWZVTUONV-UHFFFAOYSA-N 0.000 description 1
- HWSDRAPTZRYXHN-UHFFFAOYSA-N 2-(4-chlorophenyl)ethenylboronic acid Chemical compound OB(O)C=CC1=CC=C(Cl)C=C1 HWSDRAPTZRYXHN-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- ZSZKAQCISWFDCQ-UHFFFAOYSA-N 2-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC=C1S(Cl)(=O)=O ZSZKAQCISWFDCQ-UHFFFAOYSA-N 0.000 description 1
- FOYWCEUVVIHJKD-UHFFFAOYSA-N 2-methyl-5-(1h-pyrazol-5-yl)pyridine Chemical compound C1=NC(C)=CC=C1C1=CC=NN1 FOYWCEUVVIHJKD-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- XBQYQNDTMDLKEW-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-oxo-1,2-dihydroindazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2O)C2=C1 XBQYQNDTMDLKEW-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- CBFORTBWOFFDSO-UHFFFAOYSA-N 2-phenyl-1,3-dihydroindazol-5-amine Chemical compound C1C2=CC(N)=CC=C2NN1C1=CC=CC=C1 CBFORTBWOFFDSO-UHFFFAOYSA-N 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
- MJAHNNKQLXJQDX-UHFFFAOYSA-N 3,4,5-trimethoxybenzenesulfonamide Chemical group COC1=CC(S(N)(=O)=O)=CC(OC)=C1OC MJAHNNKQLXJQDX-UHFFFAOYSA-N 0.000 description 1
- APHOYGAXJBMUJN-UHFFFAOYSA-N 3,4-dichloro-n-(3-cyano-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C#N)C2=C1 APHOYGAXJBMUJN-UHFFFAOYSA-N 0.000 description 1
- MGKVYZFNGOENBH-UHFFFAOYSA-N 3,4-dichloro-n-(3-iodo-2h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2I)C2=C1 MGKVYZFNGOENBH-UHFFFAOYSA-N 0.000 description 1
- OIPHOLYBNCGEPV-UHFFFAOYSA-N 3,4-dichloro-n-(3-oxo-1,2-dihydroindazol-5-yl)benzenesulfonamide Chemical compound C1=C2C(O)=NNC2=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 OIPHOLYBNCGEPV-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
- IIQKIICAOXAXEJ-UHFFFAOYSA-N 3,5-difluorobenzenesulfonyl chloride Chemical compound FC1=CC(F)=CC(S(Cl)(=O)=O)=C1 IIQKIICAOXAXEJ-UHFFFAOYSA-N 0.000 description 1
- GTGDHOQVKFEHIX-UHFFFAOYSA-N 3-(1H-benzimidazol-2-yl)-5-phenylmethoxy-1H-indazole Chemical compound C=1C=C2NN=C(C=3NC4=CC=CC=C4N=3)C2=CC=1OCC1=CC=CC=C1 GTGDHOQVKFEHIX-UHFFFAOYSA-N 0.000 description 1
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 1
- DODDSXTWDSJCDN-UHFFFAOYSA-N 3-(trifluoromethoxy)benzenesulfonyl chloride Chemical compound FC(F)(F)OC1=CC=CC(S(Cl)(=O)=O)=C1 DODDSXTWDSJCDN-UHFFFAOYSA-N 0.000 description 1
- SVRLGCUVBOVREX-UHFFFAOYSA-N 3-[3-(1H-benzimidazol-2-yl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonic acid Chemical compound CS(=O)(=O)c1c(cccc1S(O)(=O)=O)-c1ccc2[nH]nc(-c3nc4ccccc4[nH]3)c2c1 SVRLGCUVBOVREX-UHFFFAOYSA-N 0.000 description 1
- SKDOLWSHDPLBQX-UHFFFAOYSA-N 3-chloro-n-(2-methylsulfonylphenyl)-2h-indazole-5-sulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=C(NN=C2Cl)C2=C1 SKDOLWSHDPLBQX-UHFFFAOYSA-N 0.000 description 1
- KCMAUJVSJNLYJS-UHFFFAOYSA-N 3-chloro-n-(3,4-dichlorophenyl)-2h-indazole-5-sulfonamide Chemical compound C1=C2C(Cl)=NNC2=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(Cl)=C1 KCMAUJVSJNLYJS-UHFFFAOYSA-N 0.000 description 1
- RSNAVOPEYIKHAS-UHFFFAOYSA-N 3-chloro-n-(3-fluorophenyl)-2h-indazole-5-sulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C=C3C(Cl)=NNC3=CC=2)=C1 RSNAVOPEYIKHAS-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- CJLKWWSSHYURNF-UHFFFAOYSA-N 3-cyano-n-(2-methylsulfonylphenyl)-1h-indazole-5-sulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=C(NN=C2C#N)C2=C1 CJLKWWSSHYURNF-UHFFFAOYSA-N 0.000 description 1
- SNFSUFDGPAEIID-UHFFFAOYSA-N 3-cyano-n-(3,4-dichlorophenyl)-1h-indazole-5-sulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NS(=O)(=O)C1=CC=C(NN=C2C#N)C2=C1 SNFSUFDGPAEIID-UHFFFAOYSA-N 0.000 description 1
- IIMDJNKTZRTQFN-UHFFFAOYSA-N 3-cyano-n-(3-fluorophenyl)-1h-indazole-5-sulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C=C3C(C#N)=NNC3=CC=2)=C1 IIMDJNKTZRTQFN-UHFFFAOYSA-N 0.000 description 1
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 1
- DHCAQEOFFCQKNX-UHFFFAOYSA-N 3-iodo-n-(2-methylsulfonylphenyl)-2h-indazole-5-sulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=C(NN=C2I)C2=C1 DHCAQEOFFCQKNX-UHFFFAOYSA-N 0.000 description 1
- JJERDAVMCCTTBM-UHFFFAOYSA-N 3-methyl-n-(2-methylsulfonylphenyl)-2h-indazole-5-sulfonamide Chemical compound C1=C2C(C)=NNC2=CC=C1S(=O)(=O)NC1=CC=CC=C1S(C)(=O)=O JJERDAVMCCTTBM-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OBMVMHLMAYMFJV-UHFFFAOYSA-N 4-(trifluoromethoxy)benzenesulfonic acid hydrochloride Chemical compound Cl.OS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 OBMVMHLMAYMFJV-UHFFFAOYSA-N 0.000 description 1
- SINQIEAULQKUPD-UHFFFAOYSA-N 4-[4-(6-methoxy-2-naphthalenyl)-2-(4-methylsulfinylphenyl)-1H-imidazol-5-yl]pyridine Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C=1N=C(C=2C=CC(=CC=2)S(C)=O)NC=1C1=CC=NC=C1 SINQIEAULQKUPD-UHFFFAOYSA-N 0.000 description 1
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 1
- USPLMMSVYKCRII-UHFFFAOYSA-N 4-fluoro-n-[(2-hydroxy-4-nitrophenyl)carbamothioyl]benzamide Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=S)NC(=O)C1=CC=C(F)C=C1 USPLMMSVYKCRII-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical class OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- AZYKVYXJPVOTQX-UHFFFAOYSA-N 5-(sulfonylamino)-1h-indazole Chemical group O=S(=O)=NC1=CC=C2NN=CC2=C1 AZYKVYXJPVOTQX-UHFFFAOYSA-N 0.000 description 1
- NMUSYJAQQFHJEW-UHFFFAOYSA-N 5-Azacytidine Natural products O=C1N=C(N)N=CN1C1C(O)C(O)C(CO)O1 NMUSYJAQQFHJEW-UHFFFAOYSA-N 0.000 description 1
- CLBFTTDECPUTNU-UHFFFAOYSA-N 5-[(2-methylsulfonylphenyl)sulfamoyl]-1h-indazole-3-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=C(NN=C2C(N)=O)C2=C1 CLBFTTDECPUTNU-UHFFFAOYSA-N 0.000 description 1
- SKFVIQWJAYRVAH-UHFFFAOYSA-N 5-[(2-methylsulfonylphenyl)sulfamoyl]-n-phenyl-1h-indazole-3-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=C(NN=C2C(=O)NC=3C=CC=CC=3)C2=C1 SKFVIQWJAYRVAH-UHFFFAOYSA-N 0.000 description 1
- LGZKGOGODCLQHG-CYBMUJFWSA-N 5-[(2r)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C[C@@H](O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-CYBMUJFWSA-N 0.000 description 1
- XYAXDAIFDCSEBG-UHFFFAOYSA-N 5-[(3,4-dichlorophenyl)sulfamoyl]-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)N)=NNC2=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(Cl)=C1 XYAXDAIFDCSEBG-UHFFFAOYSA-N 0.000 description 1
- TZQAULVRDCPEDB-UHFFFAOYSA-N 5-[(3,4-dichlorophenyl)sulfamoyl]-n-methyl-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(Cl)=C1 TZQAULVRDCPEDB-UHFFFAOYSA-N 0.000 description 1
- XUNMHMHIKBLWJH-UHFFFAOYSA-N 5-[(3,4-dichlorophenyl)sulfamoyl]-n-phenyl-1h-indazole-3-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NS(=O)(=O)C1=CC=C(NN=C2C(=O)NC=3C=CC=CC=3)C2=C1 XUNMHMHIKBLWJH-UHFFFAOYSA-N 0.000 description 1
- KKZDKFAOOAWBJE-UHFFFAOYSA-N 5-[(3,4-dichlorophenyl)sulfonylamino]-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)N)=NNC2=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 KKZDKFAOOAWBJE-UHFFFAOYSA-N 0.000 description 1
- CQDBUFCAIQTRJX-UHFFFAOYSA-N 5-[(3,4-dichlorophenyl)sulfonylamino]-n-methyl-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 CQDBUFCAIQTRJX-UHFFFAOYSA-N 0.000 description 1
- WMGQWBXYCOXJER-UHFFFAOYSA-N 5-[(3,4-dichlorophenyl)sulfonylamino]-n-phenyl-1h-indazole-3-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C(=O)NC=3C=CC=CC=3)C2=C1 WMGQWBXYCOXJER-UHFFFAOYSA-N 0.000 description 1
- CEIZRMABBOHTQI-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfamoyl]-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)N)=NNC2=CC=C1S(=O)(=O)NC1=CC=CC(F)=C1 CEIZRMABBOHTQI-UHFFFAOYSA-N 0.000 description 1
- MVFMVYATFHOAPT-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfamoyl]-n-methyl-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1S(=O)(=O)NC1=CC=CC(F)=C1 MVFMVYATFHOAPT-UHFFFAOYSA-N 0.000 description 1
- MNSIYAZVJORFLR-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfamoyl]-n-phenyl-1h-indazole-3-carboxamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C=C3C(C(=O)NC=4C=CC=CC=4)=NNC3=CC=2)=C1 MNSIYAZVJORFLR-UHFFFAOYSA-N 0.000 description 1
- NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 description 1
- 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 description 1
- XGSFRTHYHRTUCC-UHFFFAOYSA-N 5-nitro-1,2-dihydroindazol-3-one Chemical compound [O-][N+](=O)C1=CC=C2NNC(=O)C2=C1 XGSFRTHYHRTUCC-UHFFFAOYSA-N 0.000 description 1
- NQAATCGJMPDXHK-UHFFFAOYSA-N 5-phenylmethoxy-1h-indazole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=NNC2=CC=C1OCC1=CC=CC=C1 NQAATCGJMPDXHK-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- VAFXGOUJAXXPOQ-UHFFFAOYSA-N 6-methyl-1h-indazol-5-amine Chemical compound C1=C(N)C(C)=CC2=C1C=NN2 VAFXGOUJAXXPOQ-UHFFFAOYSA-N 0.000 description 1
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 108010048036 Angiopoietin-2 Proteins 0.000 description 1
- 108020000948 Antisense Oligonucleotides Proteins 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 102000004000 Aurora Kinase A Human genes 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 108010006654 Bleomycin Proteins 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
- DFQYZPVVDSTGGU-UHFFFAOYSA-N C12=CC(NS(=O)=O)=CC=C2NN=C1C1=CC=CC=C1 Chemical compound C12=CC(NS(=O)=O)=CC=C2NN=C1C1=CC=CC=C1 DFQYZPVVDSTGGU-UHFFFAOYSA-N 0.000 description 1
- FVLVBPDQNARYJU-XAHDHGMMSA-N C[C@H]1CCC(CC1)NC(=O)N(CCCl)N=O Chemical compound C[C@H]1CCC(CC1)NC(=O)N(CCCl)N=O FVLVBPDQNARYJU-XAHDHGMMSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 108091026890 Coding region Proteins 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 102000003910 Cyclin D Human genes 0.000 description 1
- 108090000259 Cyclin D Proteins 0.000 description 1
- 102000003903 Cyclin-dependent kinases Human genes 0.000 description 1
- 108090000266 Cyclin-dependent kinases Proteins 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
- 108010092160 Dactinomycin Proteins 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010012689 Diabetic retinopathy Diseases 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 101100015729 Drosophila melanogaster drk gene Proteins 0.000 description 1
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229940124783 FAK inhibitor Drugs 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- 102100037813 Focal adhesion kinase 1 Human genes 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 101000924533 Homo sapiens Angiopoietin-2 Proteins 0.000 description 1
- 101000798300 Homo sapiens Aurora kinase A Proteins 0.000 description 1
- 101000878536 Homo sapiens Focal adhesion kinase 1 Proteins 0.000 description 1
- 101001077604 Homo sapiens Insulin receptor substrate 1 Proteins 0.000 description 1
- 101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 description 1
- 101000693728 Homo sapiens S-acyl fatty acid synthase thioesterase, medium chain Proteins 0.000 description 1
- 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 description 1
- 108090000144 Human Proteins Proteins 0.000 description 1
- 102000003839 Human Proteins Human genes 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 108700012441 IGF2 Proteins 0.000 description 1
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 102100025087 Insulin receptor substrate 1 Human genes 0.000 description 1
- 102000004218 Insulin-Like Growth Factor I Human genes 0.000 description 1
- 102000014429 Insulin-like growth factor Human genes 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 101710128836 Large T antigen Proteins 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
- 108091054455 MAP kinase family Proteins 0.000 description 1
- 102000043136 MAP kinase family Human genes 0.000 description 1
- 206010027452 Metastases to bone Diseases 0.000 description 1
- 206010027458 Metastases to lung Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229930192392 Mitomycin Natural products 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 description 1
- 208000008636 Neoplastic Processes Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 108010089610 Nuclear Proteins Proteins 0.000 description 1
- 102000007999 Nuclear Proteins Human genes 0.000 description 1
- 108010058765 Oncogene Protein pp60(v-src) Proteins 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 102000018546 Paxillin Human genes 0.000 description 1
- ACNHBCIZLNNLRS-UHFFFAOYSA-N Paxilline 1 Natural products N1C2=CC=CC=C2C2=C1C1(C)C3(C)CCC4OC(C(C)(O)C)C(=O)C=C4C3(O)CCC1C2 ACNHBCIZLNNLRS-UHFFFAOYSA-N 0.000 description 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
- 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HFVNWDWLWUCIHC-GUPDPFMOSA-N Prednimustine Chemical compound O=C([C@@]1(O)CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)[C@@H](O)C[C@@]21C)COC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 HFVNWDWLWUCIHC-GUPDPFMOSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 description 1
- 108050002653 Retinoblastoma protein Proteins 0.000 description 1
- NDPBMCKQJOZAQX-UHFFFAOYSA-N Ro 61-8048 Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 NDPBMCKQJOZAQX-UHFFFAOYSA-N 0.000 description 1
- 102100025541 S-acyl fatty acid synthase thioesterase, medium chain Human genes 0.000 description 1
- 102000014400 SH2 domains Human genes 0.000 description 1
- 229910005948 SO2Cl Inorganic materials 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 102000001332 SRC Human genes 0.000 description 1
- 108060006706 SRC Proteins 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 1
- 108700031954 Tgfb1i1/Leupaxin/TGFB1I1 Proteins 0.000 description 1
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 1
- 208000024770 Thyroid neoplasm Diseases 0.000 description 1
- IVTVGDXNLFLDRM-HNNXBMFYSA-N Tomudex Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-HNNXBMFYSA-N 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 1
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
- ZZXDRXVIRVJQBT-UHFFFAOYSA-M Xylenesulfonate Chemical compound CC1=CC=CC(S([O-])(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-M 0.000 description 1
- GBNJRIQSFJFDII-AATRIKPKSA-N [(e)-2-(4-fluorophenyl)ethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=C(F)C=C1 GBNJRIQSFJFDII-AATRIKPKSA-N 0.000 description 1
- VKIJXFIYBAYHOE-VOTSOKGWSA-N [(e)-2-phenylethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=CC=C1 VKIJXFIYBAYHOE-VOTSOKGWSA-N 0.000 description 1
- ZWGMJLNXIVRFRJ-UHFFFAOYSA-N [1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrol-2-yl]boronic acid Chemical compound CC(C)(C)OC(=O)N1C=CC=C1B(O)O ZWGMJLNXIVRFRJ-UHFFFAOYSA-N 0.000 description 1
- IOPQYDKQISFMJI-UHFFFAOYSA-N [1-[2-bis(4-methylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(4-methylphenyl)phosphane Chemical group C1=CC(C)=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 IOPQYDKQISFMJI-UHFFFAOYSA-N 0.000 description 1
- NLBRGDIMAOSKBT-UHFFFAOYSA-N [3-(methylcarbamoyl)-1h-indazol-5-yl] 2-methylsulfonylbenzenesulfonate Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1OS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O NLBRGDIMAOSKBT-UHFFFAOYSA-N 0.000 description 1
- RWOSOODQEPZUPE-UHFFFAOYSA-N [3-(methylcarbamoyl)-1h-indazol-5-yl] 3,4-dichlorobenzenesulfonate Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1OS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 RWOSOODQEPZUPE-UHFFFAOYSA-N 0.000 description 1
- PHDHDYXTAMBEOT-UHFFFAOYSA-N [3-(methylcarbamoyl)-1h-indazol-5-yl] 3-fluorobenzenesulfonate Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1OS(=O)(=O)C1=CC=CC(F)=C1 PHDHDYXTAMBEOT-UHFFFAOYSA-N 0.000 description 1
- LMWNETOFDONKGM-UHFFFAOYSA-N [3-(phenylcarbamoyl)-1h-indazol-5-yl] 2-methylsulfonylbenzenesulfonate Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)OC1=CC=C(NN=C2C(=O)NC=3C=CC=CC=3)C2=C1 LMWNETOFDONKGM-UHFFFAOYSA-N 0.000 description 1
- KWYIOWXCMMUCEN-UHFFFAOYSA-N [3-(phenylcarbamoyl)-1h-indazol-5-yl] 3,4-dichlorobenzenesulfonate Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)OC1=CC=C(NN=C2C(=O)NC=3C=CC=CC=3)C2=C1 KWYIOWXCMMUCEN-UHFFFAOYSA-N 0.000 description 1
- SKZQOYDTUQAUBK-UHFFFAOYSA-N [3-(phenylcarbamoyl)-1h-indazol-5-yl] 3-fluorobenzenesulfonate Chemical compound FC1=CC=CC(S(=O)(=O)OC=2C=C3C(C(=O)NC=4C=CC=CC=4)=NNC3=CC=2)=C1 SKZQOYDTUQAUBK-UHFFFAOYSA-N 0.000 description 1
- RIIPFHVHLXPMHQ-UHFFFAOYSA-N [4-(dimethylamino)phenyl]boronic acid Chemical compound CN(C)C1=CC=C(B(O)O)C=C1 RIIPFHVHLXPMHQ-UHFFFAOYSA-N 0.000 description 1
- PZLVPMBCKHDVKT-UHFFFAOYSA-N [5-methoxy-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic acid Chemical compound COC1=CC=C2N(C(=O)OC(C)(C)C)C(B(O)O)=CC2=C1 PZLVPMBCKHDVKT-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-GUEYOVJQSA-N acetic acid-d4 Chemical compound [2H]OC(=O)C([2H])([2H])[2H] QTBSBXVTEAMEQO-GUEYOVJQSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 108091005764 adaptor proteins Proteins 0.000 description 1
- 102000035181 adaptor proteins Human genes 0.000 description 1
- 150000003838 adenosines Chemical class 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 102000019997 adhesion receptor Human genes 0.000 description 1
- 108010013985 adhesion receptor Proteins 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- 229960000473 altretamine Drugs 0.000 description 1
- JKOQGQFVAUAYPM-UHFFFAOYSA-N amifostine Chemical compound NCCCNCCSP(O)(O)=O JKOQGQFVAUAYPM-UHFFFAOYSA-N 0.000 description 1
- 229960001097 amifostine Drugs 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229960001220 amsacrine Drugs 0.000 description 1
- XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 230000001656 angiogenetic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940044684 anti-microtubule agent Drugs 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940045695 antineooplastic colchicine derivative Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000000074 antisense oligonucleotide Substances 0.000 description 1
- 238000012230 antisense oligonucleotides Methods 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 229960003272 asparaginase Drugs 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012131 assay buffer Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229940090047 auto-injector Drugs 0.000 description 1
- 229960002756 azacitidine Drugs 0.000 description 1
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- PMPSDYLUXAVYKH-UHFFFAOYSA-N benzoic acid hexahydrate Chemical compound O.O.O.O.O.O.OC(=O)C1=CC=CC=C1 PMPSDYLUXAVYKH-UHFFFAOYSA-N 0.000 description 1
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229960001561 bleomycin Drugs 0.000 description 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 229960002092 busulfan Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000004900 c-terminal fragment Anatomy 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 208000001969 capillary hemangioma Diseases 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 229960005243 carmustine Drugs 0.000 description 1
- 108020001778 catalytic domains Proteins 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 210000003793 centrosome Anatomy 0.000 description 1
- 230000010129 centrosome duplication Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000003399 chemotactic effect Effects 0.000 description 1
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
- 229960004630 chlorambucil Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 208000020832 chronic kidney disease Diseases 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- LGZKGOGODCLQHG-UHFFFAOYSA-N combretastatin Natural products C1=C(O)C(OC)=CC=C1CC(O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical class O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 description 1
- 229960003901 dacarbazine Drugs 0.000 description 1
- 229960000640 dactinomycin Drugs 0.000 description 1
- 229960000975 daunorubicin Drugs 0.000 description 1
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 125000005534 decanoate group Chemical class 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229960000605 dexrazoxane Drugs 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
- 229960003668 docetaxel Drugs 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 230000008482 dysregulation Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- HKSZLNNOFSGOKW-UHFFFAOYSA-N ent-staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 HKSZLNNOFSGOKW-UHFFFAOYSA-N 0.000 description 1
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 1
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 1
- 229960001904 epirubicin Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
- 125000005469 ethylenyl group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229960000961 floxuridine Drugs 0.000 description 1
- ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 1
- 229960005304 fludarabine phosphate Drugs 0.000 description 1
- GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000005699 fluoropyrimidines Chemical class 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 210000001650 focal adhesion Anatomy 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- PZJSZBJLOWMDRG-UHFFFAOYSA-N furan-2-ylboronic acid Chemical compound OB(O)C1=CC=CO1 PZJSZBJLOWMDRG-UHFFFAOYSA-N 0.000 description 1
- CYEFKCRAAGLNHW-UHFFFAOYSA-N furan-3-ylboronic acid Chemical compound OB(O)C=1C=COC=1 CYEFKCRAAGLNHW-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
- 229960005277 gemcitabine Drugs 0.000 description 1
- 229940097042 glucuronate Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229940049906 glutamate Drugs 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 101150098203 grb2 gene Proteins 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940022353 herceptin Drugs 0.000 description 1
- UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 102000045648 human IGF1R Human genes 0.000 description 1
- 102000055590 human KDR Human genes 0.000 description 1
- 102000057090 human PTK2 Human genes 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229960000908 idarubicin Drugs 0.000 description 1
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 1
- 229960001101 ifosfamide Drugs 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000002055 immunohistochemical effect Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229960004768 irinotecan Drugs 0.000 description 1
- GURKHSYORGJETM-WAQYZQTGSA-N irinotecan hydrochloride (anhydrous) Chemical compound Cl.C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 GURKHSYORGJETM-WAQYZQTGSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- XEEYBQQBJWHFJM-OUBTZVSYSA-N iron-52 Chemical compound [57Fe] XEEYBQQBJWHFJM-OUBTZVSYSA-N 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000000021 kinase assay Methods 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- YTJXGDYAEOTOCG-UHFFFAOYSA-N lithium;di(propan-2-yl)azanide;oxolane Chemical compound [Li+].C1CCOC1.CC(C)[N-]C(C)C YTJXGDYAEOTOCG-UHFFFAOYSA-N 0.000 description 1
- 229960002247 lomustine Drugs 0.000 description 1
- YROQEQPFUCPDCP-UHFFFAOYSA-N losoxantrone Chemical compound OCCNCCN1N=C2C3=CC=CC(O)=C3C(=O)C3=C2C1=CC=C3NCCNCCO YROQEQPFUCPDCP-UHFFFAOYSA-N 0.000 description 1
- 229950008745 losoxantrone Drugs 0.000 description 1
- JMZFEHDNIAQMNB-UHFFFAOYSA-N m-aminophenylboronic acid Chemical compound NC1=CC=CC(B(O)O)=C1 JMZFEHDNIAQMNB-UHFFFAOYSA-N 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- USSBDBZGEDUBHE-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate Chemical compound [Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O USSBDBZGEDUBHE-UHFFFAOYSA-L 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 201000010893 malignant breast melanoma Diseases 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
- 229960001924 melphalan Drugs 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- NGNZFAUYMKENLA-UHFFFAOYSA-N methyl 4-[5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazol-3-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O NGNZFAUYMKENLA-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000002297 mitogenic effect Effects 0.000 description 1
- 229960004857 mitomycin Drugs 0.000 description 1
- 210000000479 mitotic spindle apparatus Anatomy 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- LWPPRJSDWVLOJV-UHFFFAOYSA-N n-(1h-indazol-5-yl)-3,4,5-trimethoxybenzenesulfonamide Chemical compound COC1=C(OC)C(OC)=CC(S(=O)(=O)NC=2C=C3C=NNC3=CC=2)=C1 LWPPRJSDWVLOJV-UHFFFAOYSA-N 0.000 description 1
- QMALYKLUMURRBE-UHFFFAOYSA-N n-(1h-indazol-5-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C2NN=CC2=C1 QMALYKLUMURRBE-UHFFFAOYSA-N 0.000 description 1
- BDWINDGEUDLSQY-UHFFFAOYSA-N n-(2-methylsulfonylphenyl)-1h-indazole-5-sulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=C(NN=C2)C2=C1 BDWINDGEUDLSQY-UHFFFAOYSA-N 0.000 description 1
- VBCXBODJQRCHPV-UHFFFAOYSA-N n-(2-methylsulfonylphenyl)-3-oxo-1,2-dihydroindazole-5-sulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=C(NN=C2O)C2=C1 VBCXBODJQRCHPV-UHFFFAOYSA-N 0.000 description 1
- XFVXUBQDJQXBAE-UHFFFAOYSA-N n-(2-methylsulfonylphenyl)-3-phenyl-1h-indazole-5-sulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 XFVXUBQDJQXBAE-UHFFFAOYSA-N 0.000 description 1
- DGUNWFWEAYBSBE-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-1h-indazole-5-sulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NS(=O)(=O)C1=CC=C(NN=C2)C2=C1 DGUNWFWEAYBSBE-UHFFFAOYSA-N 0.000 description 1
- XNFKDQMCCBLBSM-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-3-iodo-2h-indazole-5-sulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NS(=O)(=O)C1=CC=C(NN=C2I)C2=C1 XNFKDQMCCBLBSM-UHFFFAOYSA-N 0.000 description 1
- KFCJWDCLXKTDKE-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-3-methyl-2h-indazole-5-sulfonamide Chemical compound C1=C2C(C)=NNC2=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(Cl)=C1 KFCJWDCLXKTDKE-UHFFFAOYSA-N 0.000 description 1
- RPVRPOYQVFOBLL-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-3-oxo-1,2-dihydroindazole-5-sulfonamide Chemical compound C1=C2C(O)=NNC2=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(Cl)=C1 RPVRPOYQVFOBLL-UHFFFAOYSA-N 0.000 description 1
- MROBLLQULQJDQZ-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-3-phenyl-1h-indazole-5-sulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NS(=O)(=O)C1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 MROBLLQULQJDQZ-UHFFFAOYSA-N 0.000 description 1
- QLVSZMRLAHMVLT-UHFFFAOYSA-N n-(3-fluorophenyl)-3-iodo-2h-indazole-5-sulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C=C3C(I)=NNC3=CC=2)=C1 QLVSZMRLAHMVLT-UHFFFAOYSA-N 0.000 description 1
- ALXYQCGNBHORNA-UHFFFAOYSA-N n-(3-fluorophenyl)-3-methyl-2h-indazole-5-sulfonamide Chemical compound C1=C2C(C)=NNC2=CC=C1S(=O)(=O)NC1=CC=CC(F)=C1 ALXYQCGNBHORNA-UHFFFAOYSA-N 0.000 description 1
- UCYNBWABTRUMCI-UHFFFAOYSA-N n-(3-fluorophenyl)-3-oxo-1,2-dihydroindazole-5-sulfonamide Chemical compound C1=C2C(O)=NNC2=CC=C1S(=O)(=O)NC1=CC=CC(F)=C1 UCYNBWABTRUMCI-UHFFFAOYSA-N 0.000 description 1
- PDKYKGQJSBOCAS-UHFFFAOYSA-N n-(3-fluorophenyl)-3-phenyl-1h-indazole-5-sulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 PDKYKGQJSBOCAS-UHFFFAOYSA-N 0.000 description 1
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 1
- GEPXTWVOVXCXIU-UHFFFAOYSA-N n-[5-[(2-methylsulfonylphenyl)sulfamoyl]-1h-indazol-3-yl]benzamide Chemical compound CS(=O)(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=C(NN=C2NC(=O)C=3C=CC=CC=3)C2=C1 GEPXTWVOVXCXIU-UHFFFAOYSA-N 0.000 description 1
- XBWHMYWCWPRDEL-UHFFFAOYSA-N n-[5-[(3,4-dichlorophenyl)sulfamoyl]-1h-indazol-3-yl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NS(=O)(=O)C1=CC=C(NN=C2NC(=O)C=3C=CC=CC=3)C2=C1 XBWHMYWCWPRDEL-UHFFFAOYSA-N 0.000 description 1
- PEQIKACFLWKMEE-UHFFFAOYSA-N n-[5-[(3,4-dichlorophenyl)sulfonylamino]-1h-indazol-3-yl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2NC(=O)C=3C=CC=CC=3)C2=C1 PEQIKACFLWKMEE-UHFFFAOYSA-N 0.000 description 1
- DMJLGEKNPNRGMY-UHFFFAOYSA-N n-[5-[(3-fluorophenyl)sulfamoyl]-1h-indazol-3-yl]benzamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C=C3C(NC(=O)C=4C=CC=CC=4)=NNC3=CC=2)=C1 DMJLGEKNPNRGMY-UHFFFAOYSA-N 0.000 description 1
- YMJYTQZTJSPUNA-UHFFFAOYSA-N n-methyl-5-[(2-methylsulfonylphenyl)sulfamoyl]-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1S(=O)(=O)NC1=CC=CC=C1S(C)(=O)=O YMJYTQZTJSPUNA-UHFFFAOYSA-N 0.000 description 1
- SHNYHNHKJNKNNH-UHFFFAOYSA-N n-methyl-5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O SHNYHNHKJNKNNH-UHFFFAOYSA-N 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000004940 nucleus Anatomy 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical class CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 230000002246 oncogenic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229960001756 oxaliplatin Drugs 0.000 description 1
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- ACNHBCIZLNNLRS-UBGQALKQSA-N paxilline Chemical compound N1C2=CC=CC=C2C2=C1[C@]1(C)[C@@]3(C)CC[C@@H]4O[C@H](C(C)(O)C)C(=O)C=C4[C@]3(O)CC[C@H]1C2 ACNHBCIZLNNLRS-UBGQALKQSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960002340 pentostatin Drugs 0.000 description 1
- FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000003668 pericyte Anatomy 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 238000003566 phosphorylation assay Methods 0.000 description 1
- 208000017983 photosensitivity disease Diseases 0.000 description 1
- 231100000434 photosensitization Toxicity 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- WLJVNTCWHIRURA-UHFFFAOYSA-M pimelate(1-) Chemical compound OC(=O)CCCCCC([O-])=O WLJVNTCWHIRURA-UHFFFAOYSA-M 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 229960004694 prednimustine Drugs 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
- 229960000624 procarbazine Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- CDRNYKLYADJTMN-UHFFFAOYSA-N pyridine-3-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CN=C1 CDRNYKLYADJTMN-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- KXJJSKYICDAICD-UHFFFAOYSA-N quinolin-8-ylboronic acid Chemical compound C1=CN=C2C(B(O)O)=CC=CC2=C1 KXJJSKYICDAICD-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229960004432 raltitrexed Drugs 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229960003440 semustine Drugs 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- LKYIPGJOXSVWPX-UHFFFAOYSA-M sodium;thiophene-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=CS1 LKYIPGJOXSVWPX-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000024477 spindle organization Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 description 1
- CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960001052 streptozocin Drugs 0.000 description 1
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229960005314 suramin Drugs 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 229960004964 temozolomide Drugs 0.000 description 1
- 229960001278 teniposide Drugs 0.000 description 1
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
- AXKRSZJROHSNKO-UHFFFAOYSA-N tert-butyl 5-[(3-fluorophenyl)sulfonyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-iodo-1,2-dihydroindazole-3-carboxylate Chemical compound C=1C=C2NNC(I)(C(=O)OC(C)(C)C)C2=CC=1N(C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CC(F)=C1 AXKRSZJROHSNKO-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 102000027257 transmembrane receptors Human genes 0.000 description 1
- 108091008578 transmembrane receptors Proteins 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 239000004066 vascular targeting agent Substances 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0202996A FR2836914B1 (fr) | 2002-03-11 | 2002-03-11 | Indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
PCT/FR2003/000751 WO2003078402A1 (fr) | 2002-03-11 | 2003-03-07 | Indazoles substitues avec une activite anticancereuse |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20040825A2 true HRP20040825A2 (en) | 2005-06-30 |
Family
ID=27763684
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20040825A HRP20040825A2 (en) | 2002-03-11 | 2004-09-10 | Indazoles substituted with an anti-cancerous activity |
Country Status (29)
Country | Link |
---|---|
US (2) | US6858638B2 (zh) |
EP (1) | EP1487803A1 (zh) |
JP (1) | JP4643910B2 (zh) |
KR (1) | KR20040091128A (zh) |
CN (1) | CN100369899C (zh) |
AR (1) | AR038914A1 (zh) |
AU (1) | AU2003242808B2 (zh) |
BR (1) | BR0308339A (zh) |
CA (1) | CA2478540A1 (zh) |
EC (1) | ECSP045286A (zh) |
FR (1) | FR2836914B1 (zh) |
GT (1) | GT200300031A (zh) |
HN (1) | HN2003000094A (zh) |
HR (1) | HRP20040825A2 (zh) |
IL (2) | IL163805A0 (zh) |
MA (1) | MA27176A1 (zh) |
MX (1) | MXPA04008446A (zh) |
NO (1) | NO20044261L (zh) |
OA (1) | OA12784A (zh) |
PA (1) | PA8566701A1 (zh) |
PE (1) | PE20040071A1 (zh) |
PL (1) | PL372389A1 (zh) |
RU (1) | RU2004130280A (zh) |
SV (1) | SV2003001493A (zh) |
TN (1) | TNSN04175A1 (zh) |
TW (1) | TW200303863A (zh) |
UY (1) | UY27712A1 (zh) |
WO (1) | WO2003078402A1 (zh) |
ZA (1) | ZA200406730B (zh) |
Families Citing this family (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2836914B1 (fr) * | 2002-03-11 | 2008-03-14 | Aventis Pharma Sa | Indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
GB0218625D0 (en) * | 2002-08-10 | 2002-09-18 | Astex Technology Ltd | Pharmaceutical compounds |
AU2003286711A1 (en) | 2002-10-25 | 2004-05-13 | Vertex Pharmaceuticals Incorporated | Indazolinone compositions useful as kinase inhibitors |
US7135575B2 (en) | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
WO2005014554A1 (en) * | 2003-08-08 | 2005-02-17 | Astex Therapeutics Limited | 1h-indazole-3-carboxamide compounds as mapkap kinase modulators |
FR2864084B1 (fr) * | 2003-12-17 | 2006-02-10 | Aventis Pharma Sa | Nouveaux derives organophosphores des indazoles et leur utilisation comme medicaments |
WO2005061519A1 (en) * | 2003-12-19 | 2005-07-07 | Takeda San Diego, Inc. | Kinase inhibitors |
GB0330043D0 (en) * | 2003-12-24 | 2004-01-28 | Pharmacia Italia Spa | Pyrrolo [2,3-b] pyridine derivatives active as kinase inhibitors process for their preparation and pharmaceutical compositions comprising them |
GB0330042D0 (en) * | 2003-12-24 | 2004-01-28 | Pharmacia Italia Spa | Pyrrolo [2,3-b] pyridine derivatives active as kinase inhibitors process for their preparation and pharmaceutical compositions them |
JP2007533753A (ja) * | 2004-04-23 | 2007-11-22 | タケダ サン ディエゴ インコーポレイテッド | インドール誘導体及びキナーゼ阻害剤としてのその使用 |
EP1778669A2 (en) * | 2004-08-18 | 2007-05-02 | Takeda San Diego, Inc. | Kinase inhibitors |
PT1797042E (pt) * | 2004-09-29 | 2009-02-12 | Hoffmann La Roche | Derivados de indozolona como inibidores de 11b-hsd1 |
US7713973B2 (en) | 2004-10-15 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
SE0402762D0 (sv) * | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Indazole sulphonamide derivatives |
SE0402763D0 (sv) * | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Nitro indazole derivatives |
EP1919877A1 (en) * | 2005-08-25 | 2008-05-14 | F.Hoffmann-La Roche Ag | P38 map kinase inhibitors and methods for using the same |
US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
CA2635813C (en) | 2006-01-31 | 2014-01-07 | Array Biopharma, Inc. | Urea derivatives as kinase inhibitors and methods of use thereof |
SG158147A1 (en) | 2006-10-09 | 2010-01-29 | Takeda Pharmaceutical | Kinase inhibitors |
EP2223925A1 (en) * | 2006-10-09 | 2010-09-01 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
WO2008063888A2 (en) * | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
FR2917735B1 (fr) * | 2007-06-21 | 2009-09-04 | Sanofi Aventis Sa | Nouveaux indazoles substitutes, leur preparation et leur utilisation en therapeutique |
ES2457418T3 (es) | 2007-07-16 | 2014-04-25 | Abbvie Inc. | Indazoles, bencisoxazoles y bencisotiazoles como inhibidores de proteína cinasas |
US9034875B2 (en) | 2009-05-26 | 2015-05-19 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
ME02205B (me) | 2009-05-26 | 2016-02-20 | Abbvie Bahamas Ltd | INDUKUJUĆI AGENSI APOPTOZE ZA LEČENJE KANCERA I IMUNIH l AUTOIMUNIH OBOLJENJA |
US20220315555A1 (en) | 2009-05-26 | 2022-10-06 | Abbvie Inc. | Apoptosis inducing agents for the treatment of cancer and immune and autoimmune diseases |
US8546399B2 (en) | 2009-05-26 | 2013-10-01 | Abbvie Inc. | Apoptosis inducing agents for the treatment of cancer and immune and autoimmune diseases |
WO2011050245A1 (en) * | 2009-10-23 | 2011-04-28 | Yangbo Feng | Bicyclic heteroaryls as kinase inhibitors |
CN102247361B (zh) * | 2010-05-20 | 2015-04-29 | 中国医学科学院药物研究所 | 5-硝基-1氢-吲唑-3-腈在制备药物中的应用 |
UA113500C2 (xx) | 2010-10-29 | 2017-02-10 | Одержані екструзією розплаву тверді дисперсії, що містять індукуючий апоптоз засіб | |
KR20180059560A (ko) | 2010-10-29 | 2018-06-04 | 애브비 인코포레이티드 | 아폽토시스―유도제를 포함하는 고체 분산체 |
UY33746A (es) | 2010-11-23 | 2012-06-29 | Abbott Lab | Método de tratamiento que usa inhibidores selectivos de bcl-2 |
AU2011332043C1 (en) | 2010-11-23 | 2016-11-10 | Abbvie Inc. | Salts and crystalline forms of an apoptosis-inducing agent |
US20140275082A1 (en) | 2013-03-14 | 2014-09-18 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
AU2015341913B2 (en) | 2014-11-03 | 2020-07-16 | Iomet Pharma Ltd | Pharmaceutical compound |
GB201511382D0 (en) | 2015-06-29 | 2015-08-12 | Imp Innovations Ltd | Novel compounds and their use in therapy |
US11926596B2 (en) | 2017-07-21 | 2024-03-12 | Kadmon Corporation, Llc | Inhibitors of Rho associated coiled-coil containing protein kinase |
EP3676255A1 (en) | 2017-08-29 | 2020-07-08 | Rutgers, The State University University Of New Jersey | Therapeutic indazoles |
WO2023137041A1 (en) * | 2022-01-12 | 2023-07-20 | Ifm Due, Inc. | Compounds and compositions for treating conditions associated with sting activity |
CN114605329B (zh) * | 2022-03-28 | 2024-01-26 | 河南中医药大学 | 取代的吲唑甲酰胺或取代的氮杂吲唑甲酰胺类flt3抑制剂及其用途 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS514505Y2 (zh) | 1971-02-13 | 1976-02-07 | ||
JPH061350B2 (ja) * | 1985-07-26 | 1994-01-05 | コニカ株式会社 | ハロゲン化銀写真感光材料 |
DK0896533T3 (da) | 1996-02-22 | 2004-01-26 | Tularik Inc | Pentafluorbenzensulfonamider og analoger |
CN1147294C (zh) * | 1996-07-19 | 2004-04-28 | 图拉列克股份有限公司 | 五氟苯磺酰胺及其类似物 |
GB9718913D0 (en) * | 1997-09-05 | 1997-11-12 | Glaxo Group Ltd | Substituted oxindole derivatives |
US6087368A (en) * | 1998-06-08 | 2000-07-11 | Bristol-Myers Squibb Company | Quinazolinone inhibitors of cGMP phosphodiesterase |
AU1818400A (en) | 1998-11-12 | 2000-05-29 | Eli Lilly And Company | Aryloxime linkers in the solid-phase synthesis of 3-aminobenzisoxazoles |
CO5170498A1 (es) * | 1999-05-28 | 2002-06-27 | Abbott Lab | Biaril sulfonamidas son utiles como inhibidores de proliferacion celular |
YU54202A (sh) | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
KR100423899B1 (ko) * | 2000-05-10 | 2004-03-24 | 주식회사 엘지생명과학 | 세포 증식 억제제로 유용한 1,1-디옥소이소티아졸리딘을갖는 인다졸 |
US6897231B2 (en) * | 2000-07-31 | 2005-05-24 | Signal Pharmaceuticals, Inc. | Indazole derivatives as JNK inhibitors and compositions and methods related thereto |
CA2440842A1 (en) * | 2001-04-16 | 2002-10-24 | Eisai Co., Ltd. | Novel 1h-indazole compounds |
EP1403255A4 (en) | 2001-06-12 | 2005-04-06 | Sumitomo Pharma | INHIBITORS OF RHO KINASE |
US7064215B2 (en) * | 2001-07-03 | 2006-06-20 | Chiron Corporation | Indazole benzimidazole compounds |
US7101884B2 (en) | 2001-09-14 | 2006-09-05 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
FR2836915B1 (fr) | 2002-03-11 | 2008-01-11 | Aventis Pharma Sa | Derives d'aminoindazoles, procede de preparation et intermediaires de ce procede a titre de medicaments et compositions pharmaceutiques les renfermant |
FR2836914B1 (fr) * | 2002-03-11 | 2008-03-14 | Aventis Pharma Sa | Indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
-
2002
- 2002-03-11 FR FR0202996A patent/FR2836914B1/fr not_active Expired - Fee Related
-
2003
- 2003-02-06 GT GT200300031A patent/GT200300031A/es unknown
- 2003-02-13 PA PA20038566701A patent/PA8566701A1/es unknown
- 2003-02-24 TW TW092103799A patent/TW200303863A/zh unknown
- 2003-03-03 SV SV2003001493A patent/SV2003001493A/es not_active Application Discontinuation
- 2003-03-07 EP EP03744395A patent/EP1487803A1/fr not_active Withdrawn
- 2003-03-07 IL IL16380503A patent/IL163805A0/xx unknown
- 2003-03-07 KR KR10-2004-7014298A patent/KR20040091128A/ko not_active Application Discontinuation
- 2003-03-07 BR BR0308339-0A patent/BR0308339A/pt not_active IP Right Cessation
- 2003-03-07 JP JP2003576408A patent/JP4643910B2/ja not_active Expired - Fee Related
- 2003-03-07 OA OA1200400236A patent/OA12784A/fr unknown
- 2003-03-07 AU AU2003242808A patent/AU2003242808B2/en not_active Ceased
- 2003-03-07 CN CNB038058731A patent/CN100369899C/zh not_active Expired - Fee Related
- 2003-03-07 PE PE2003000232A patent/PE20040071A1/es not_active Application Discontinuation
- 2003-03-07 CA CA002478540A patent/CA2478540A1/fr not_active Abandoned
- 2003-03-07 MX MXPA04008446A patent/MXPA04008446A/es active IP Right Grant
- 2003-03-07 WO PCT/FR2003/000751 patent/WO2003078402A1/fr active Application Filing
- 2003-03-07 RU RU2004130280/04A patent/RU2004130280A/ru not_active Application Discontinuation
- 2003-03-07 PL PL03372389A patent/PL372389A1/xx not_active Application Discontinuation
- 2003-03-10 AR ARP030100807A patent/AR038914A1/es unknown
- 2003-03-10 HN HN2003000094A patent/HN2003000094A/es unknown
- 2003-03-11 US US10/385,870 patent/US6858638B2/en not_active Expired - Lifetime
- 2003-03-11 UY UY27712A patent/UY27712A1/es unknown
-
2004
- 2004-08-12 MA MA27825A patent/MA27176A1/fr unknown
- 2004-08-24 ZA ZA200406730A patent/ZA200406730B/en unknown
- 2004-08-30 IL IL163805A patent/IL163805A/en not_active IP Right Cessation
- 2004-09-10 EC EC2004005286A patent/ECSP045286A/es unknown
- 2004-09-10 HR HR20040825A patent/HRP20040825A2/hr not_active Application Discontinuation
- 2004-09-10 TN TNP2004000175A patent/TNSN04175A1/fr unknown
- 2004-10-07 NO NO20044261A patent/NO20044261L/no unknown
- 2004-10-13 US US10/963,880 patent/US7473701B2/en not_active Expired - Lifetime
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HRP20040825A2 (en) | Indazoles substituted with an anti-cancerous activity | |
AU2007248341B2 (en) | Benzimidazole modulators of VR1 | |
US8017641B2 (en) | P38 inhibitors and methods of use thereof | |
SK19252001A3 (sk) | Indazolové zlúčeniny, farmaceutické prípravky na inhibíciu proteínkináz a ich použitie | |
ZA200500153B (en) | -3 (sulfonamidoethyl)-indole derivatives for use as glucocorticoid mimetics in the treatment of inflammatory, allergic and proliferative diseases | |
EP1606283A2 (en) | P38 inhibitors and methods of use thereof | |
FR2917735A1 (fr) | Nouveaux indazoles substitutes, leur preparation et leur utilisation en therapeutique | |
AU2006209712A1 (en) | IGF-1R inhibitor | |
JP2008501669A (ja) | 置換インダゾール、それらを含有する組成物、それらの調製及びそれらの使用 | |
CA2642232A1 (en) | Mandelic hydrazides | |
JP2005529954A (ja) | 化学プロセス | |
EP1841762A1 (fr) | Indoles substitues, compositions les contenant, procede de fabrication et utilisation | |
JP2005519074A (ja) | 治療用の置換インダゾール誘導体 | |
JPWO2005012258A1 (ja) | タンパク質キナーゼ阻害剤 | |
CN110835333B (zh) | 苯并咪唑取代唑类化合物及其用途 | |
JP2008534633A (ja) | Chk1、chk2およびsgk阻害剤としてのインダゾールスクアリン酸誘導体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A1OB | Publication of a patent application | ||
ARAI | Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application | ||
ODRP | Renewal fee for the maintenance of a patent |
Payment date: 20060227 Year of fee payment: 4 |
|
OBST | Application withdrawn |