JP2005533004A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005533004A5 JP2005533004A5 JP2003576408A JP2003576408A JP2005533004A5 JP 2005533004 A5 JP2005533004 A5 JP 2005533004A5 JP 2003576408 A JP2003576408 A JP 2003576408A JP 2003576408 A JP2003576408 A JP 2003576408A JP 2005533004 A5 JP2005533004 A5 JP 2005533004A5
- Authority
- JP
- Japan
- Prior art keywords
- indazol
- phenyl
- benzenesulfonamide
- methanesulfonylbenzenesulfonamide
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000003107 substituted aryl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 4
- BWAGAWVSXXJADX-UHFFFAOYSA-N n-[4-[(3-phenyl-1h-indazol-5-yl)sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 BWAGAWVSXXJADX-UHFFFAOYSA-N 0.000 claims description 3
- 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 2
- SMCGMAXYINPFGK-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2-phenylethyl)-2h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2CCC=3C=CC=CC=3)C2=C1 SMCGMAXYINPFGK-UHFFFAOYSA-N 0.000 claims description 2
- DWWIPKOTLDERIH-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2-phenylethynyl)-2h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C#CC=3C=CC=CC=3)C2=C1 DWWIPKOTLDERIH-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- NCHATSXVPBRKKR-UHFFFAOYSA-N 3-fluoro-N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4NC5=CC=CC=C5C=4)=NNC3=CC=2)=C1 NCHATSXVPBRKKR-UHFFFAOYSA-N 0.000 claims description 2
- VRVWVMZURIDGGD-UHFFFAOYSA-N 4-amino-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 VRVWVMZURIDGGD-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- -1 6- (2-dimethylaminomethyl-5-methylmorpholin-4-yl) -1H-benzimidazol-2-yl Chemical group 0.000 claims 30
- 108091000080 Phosphotransferase Proteins 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 102000020233 phosphotransferase Human genes 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 229940124530 sulfonamide Drugs 0.000 claims 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- 101100481408 Danio rerio tie2 gene Proteins 0.000 claims 2
- 101100481410 Mus musculus Tek gene Proteins 0.000 claims 2
- SVOWCBCFXJLRIU-UHFFFAOYSA-N N-[3-(4-hydroxyphenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(O)=CC=3)C2=C1 SVOWCBCFXJLRIU-UHFFFAOYSA-N 0.000 claims 2
- 101150001535 SRC gene Proteins 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 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 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- ZBJBBHDHWHEJQB-UHFFFAOYSA-N 2-(3-phenyl-1H-indazol-5-yl)-3-thiophen-2-yl-3H-1,2-oxazole Chemical compound C1(=CC=CC=C1)C1=NNC2=CC=C(C=C12)N1OC=CC1C1=CC=CS1 ZBJBBHDHWHEJQB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- ZKDVCIAPCQMSJW-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-pyridin-4-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CN=CC=3)C2=C1 ZKDVCIAPCQMSJW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 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 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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 claims 1
- GMGAOIPGKMEZHC-UHFFFAOYSA-N 6-(4-methylpiperazin-1-yl)-1h-benzimidazole Chemical compound C1CN(C)CCN1C1=CC=C(N=CN2)C2=C1 GMGAOIPGKMEZHC-UHFFFAOYSA-N 0.000 claims 1
- 108090000461 Aurora Kinase A Proteins 0.000 claims 1
- 102100032311 Aurora kinase A Human genes 0.000 claims 1
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims 1
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims 1
- 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims 1
- 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 claims 1
- 101001034652 Homo sapiens Insulin-like growth factor 1 receptor Proteins 0.000 claims 1
- 102100039688 Insulin-like growth factor 1 receptor Human genes 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical compound NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 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 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- IBXPTSRLYBPVJO-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)piperidine-4-sulfonamide Chemical compound C1CNCCC1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 IBXPTSRLYBPVJO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- ZYRMFMZOLKOEFZ-UHFFFAOYSA-N n-[3-(3-aminophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(N)C=CC=3)C2=C1 ZYRMFMZOLKOEFZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- LGRLGKDJPSXDFD-UHFFFAOYSA-N oxadiazole-4-sulfonamide Chemical compound NS(=O)(=O)C1=CON=N1 LGRLGKDJPSXDFD-UHFFFAOYSA-N 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000005504 styryl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2005533004A JP2005533004A (ja) | 2005-11-04 |
| JP2005533004A5 true JP2005533004A5 (enExample) | 2006-04-20 |
| JP4643910B2 JP4643910B2 (ja) | 2011-03-02 |
Family
ID=27763684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003576408A Expired - Fee Related JP4643910B2 (ja) | 2002-03-11 | 2003-03-07 | 抗癌活性を有する置換インダゾール |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US6858638B2 (enExample) |
| EP (1) | EP1487803A1 (enExample) |
| JP (1) | JP4643910B2 (enExample) |
| KR (1) | KR20040091128A (enExample) |
| CN (1) | CN100369899C (enExample) |
| AR (1) | AR038914A1 (enExample) |
| AU (1) | AU2003242808B2 (enExample) |
| BR (1) | BR0308339A (enExample) |
| CA (1) | CA2478540A1 (enExample) |
| EC (1) | ECSP045286A (enExample) |
| FR (1) | FR2836914B1 (enExample) |
| GT (1) | GT200300031A (enExample) |
| HN (1) | HN2003000094A (enExample) |
| HR (1) | HRP20040825A2 (enExample) |
| IL (2) | IL163805A0 (enExample) |
| MA (1) | MA27176A1 (enExample) |
| MX (1) | MXPA04008446A (enExample) |
| NO (1) | NO20044261L (enExample) |
| OA (1) | OA12784A (enExample) |
| PA (1) | PA8566701A1 (enExample) |
| PE (1) | PE20040071A1 (enExample) |
| PL (1) | PL372389A1 (enExample) |
| RU (1) | RU2004130280A (enExample) |
| SV (1) | SV2003001493A (enExample) |
| TN (1) | TNSN04175A1 (enExample) |
| TW (1) | TW200303863A (enExample) |
| UY (1) | UY27712A1 (enExample) |
| WO (1) | WO2003078402A1 (enExample) |
| ZA (1) | ZA200406730B (enExample) |
Families Citing this family (43)
| 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 |
| WO2004037814A1 (en) * | 2002-10-25 | 2004-05-06 | 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 |
| EP1694686A1 (en) | 2003-12-19 | 2006-08-30 | Takeda San Diego, Inc. | Kinase inhibitors |
| 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 |
| 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 |
| WO2005105788A1 (en) * | 2004-04-23 | 2005-11-10 | Takeda San Diego, Inc. | Indole derivatives and use thereof as kinase inhibitors |
| JP2008510734A (ja) | 2004-08-18 | 2008-04-10 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
| SI1797042T1 (sl) * | 2004-09-29 | 2009-04-30 | Hoffmann La Roche | Indozolonski derivati kot inhibitorji 11b-hsd1 |
| EP1812439B2 (en) | 2004-10-15 | 2017-12-06 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| SE0402763D0 (sv) * | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Nitro indazole derivatives |
| SE0402762D0 (sv) * | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Indazole sulphonamide derivatives |
| BRPI0615094A2 (pt) * | 2005-08-25 | 2011-05-03 | Hoffmann La Roche | inibidores de p38 map cinase e métodos de uso dos mesmos |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| JP5131990B2 (ja) | 2006-01-31 | 2013-01-30 | アレイ バイオファーマ、インコーポレイテッド | キナーゼ阻害剤およびその使用方法 |
| EP2223925A1 (en) * | 2006-10-09 | 2010-09-01 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| JP2010505962A (ja) | 2006-10-09 | 2010-02-25 | 武田薬品工業株式会社 | キナーゼ阻害剤 |
| 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 |
| US8546399B2 (en) | 2009-05-26 | 2013-10-01 | Abbvie Inc. | Apoptosis inducing agents for the treatment of cancer and immune and autoimmune diseases |
| US20220315555A1 (en) | 2009-05-26 | 2022-10-06 | Abbvie Inc. | Apoptosis inducing agents for the treatment of cancer and immune and autoimmune diseases |
| UY32668A (es) * | 2009-05-26 | 2010-12-31 | Abbott Lab | Agentes inductores de la apoptosis para el tratamiento del cáncer y de enfermedades inmunes y autoinmunes |
| US9034875B2 (en) | 2009-05-26 | 2015-05-19 | 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 | |
| EP2632436B1 (en) | 2010-10-29 | 2018-08-29 | Abbvie Inc. | Solid dispersions containing an apoptosis-inducing agent |
| NZ708508A (en) | 2010-11-23 | 2016-06-24 | Abbvie Bahamas Ltd | Methods of treatment using selective bcl-2 inhibitors |
| JP6141188B2 (ja) | 2010-11-23 | 2017-06-07 | アッヴィ・インコーポレイテッド | アポトーシス誘導剤の塩および結晶の形態 |
| US20140275082A1 (en) | 2013-03-14 | 2014-09-18 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| KR102602947B1 (ko) | 2014-11-03 | 2023-11-16 | 아이오메트 파마 엘티디 | 제약 화합물 |
| GB201511382D0 (en) | 2015-06-29 | 2015-08-12 | Imp Innovations Ltd | Novel compounds and their use in therapy |
| JP2020528415A (ja) | 2017-07-21 | 2020-09-24 | カドモン コーポレイション，リミティド ライアビリティ カンパニー | Ｒｈｏ関連コイルドコイル含有プロテインキナーゼの阻害剤 |
| WO2019046467A1 (en) | 2017-08-29 | 2019-03-07 | Rutgers, The State University Of New Jersey | INDAZOLES THERAPEUTIC |
| EP4463441A1 (en) * | 2022-01-12 | 2024-11-20 | IFM Due, Inc. | Compounds and compositions for treating conditions associated with sting activity |
| CN116693519A (zh) | 2022-03-04 | 2023-09-05 | 上海璎黎药业有限公司 | 一种含五元杂芳环结构化合物、其药物组合物及应用 |
| 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 |
| EP4642764A2 (en) | 2022-12-30 | 2025-11-05 | Avicenna Biosciences, Inc. | Azaindole rock inhibitors |
| WO2025117661A1 (en) * | 2023-11-28 | 2025-06-05 | Quantx Biosciences Us, Inc. | Bicyclic heteroaryl compounds |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS514505Y2 (enExample) | 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 |
| EP0896533B1 (en) | 1996-02-22 | 2003-09-10 | Tularik, Inc. | Pentafluorobenzenesulfonamides and analogs |
| WO1998005315A1 (en) * | 1996-07-19 | 1998-02-12 | Tularik, Inc. | Pentafluorobenzenesulfonamides and analogs |
| 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 |
| WO2000027627A1 (en) | 1998-11-12 | 2000-05-18 | 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 |
| CN1300116C (zh) | 2001-04-16 | 2007-02-14 | 卫材株式会社 | 1h－吲唑化合物 |
| WO2002100833A1 (en) | 2001-06-12 | 2002-12-19 | Sumitomo Pharmaceuticals Company, Limited | Rho KINASE INHIBITORS |
| JP2004536113A (ja) * | 2001-07-03 | 2004-12-02 | カイロン コーポレイション | チロシンキナーゼおよびセリン／スレオニンキナーゼのインヒビターとしてのインダゾールベンズイミダゾール化合物 |
| US7101884B2 (en) | 2001-09-14 | 2006-09-05 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| FR2836914B1 (fr) * | 2002-03-11 | 2008-03-14 | Aventis Pharma Sa | Indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
| 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 |
-
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 RU RU2004130280/04A patent/RU2004130280A/ru not_active Application Discontinuation
- 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 CA CA002478540A patent/CA2478540A1/fr not_active Abandoned
- 2003-03-07 PL PL03372389A patent/PL372389A1/xx not_active Application Discontinuation
- 2003-03-07 EP EP03744395A patent/EP1487803A1/fr not_active Withdrawn
- 2003-03-07 PE PE2003000232A patent/PE20040071A1/es not_active Application Discontinuation
- 2003-03-07 KR KR10-2004-7014298A patent/KR20040091128A/ko not_active Ceased
- 2003-03-07 HR HR20040825A patent/HRP20040825A2/hr not_active Application Discontinuation
- 2003-03-07 OA OA1200400236A patent/OA12784A/fr unknown
- 2003-03-07 IL IL16380503A patent/IL163805A0/xx unknown
- 2003-03-07 WO PCT/FR2003/000751 patent/WO2003078402A1/fr not_active Ceased
- 2003-03-07 MX MXPA04008446A patent/MXPA04008446A/es active IP Right Grant
- 2003-03-07 JP JP2003576408A patent/JP4643910B2/ja not_active Expired - Fee Related
- 2003-03-07 BR BR0308339-0A patent/BR0308339A/pt not_active IP Right Cessation
- 2003-03-10 HN HN2003000094A patent/HN2003000094A/es unknown
- 2003-03-10 AR ARP030100807A patent/AR038914A1/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 TN TNP2004000175A patent/TNSN04175A1/fr unknown
- 2004-09-10 EC EC2004005286A patent/ECSP045286A/es unknown
- 2004-10-07 NO NO20044261A patent/NO20044261L/no unknown
- 2004-10-13 US US10/963,880 patent/US7473701B2/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005533004A5 (enExample) | ||
| RU2004130280A (ru) | Замещенные индазолы, обладающие притовораковой активностью | |
| AU2002342607B2 (en) | Aminoisoxazole derivatives active as kinase inhibitors | |
| HRP20100283T1 (hr) | Derivati n-'(1,5-difenil-1h-pirazol-3-il)sulfonamida s afinitetom za cb1 receptor | |
| RU2361860C2 (ru) | Новые замещенные 3-сера-индолы | |
| RU2392272C2 (ru) | Производные индазолона в качестве ингибиторов 11b-hsd1 | |
| CA2494695A1 (en) | 2-(3-aminoaryl)amino-4-aryl-thiazoles and their use as c-kit inhibitors | |
| RU2478632C2 (ru) | Гидроксилированные и метоксилированные циклопента[d]пиримидины в качестве ингибиторов акт протеинкиназ | |
| RU2326869C2 (ru) | Производные пиридазин-3(2h)-она в качестве ингибиторов фосфодиэстеразы 4 (pde4), способ их получения, фармацевтическая композиция и способ лечения | |
| CA2526430A1 (en) | Indazole, benzisoxazole, and benzisothiazole kinase inhibitors | |
| JP2004525951A5 (enExample) | ||
| RU2005121897A (ru) | Производные аминоиндазолов и их применение в качестве ингибиторов киназ | |
| CA2396824A1 (en) | Heteroaromatic carboxamide derivatives and their use as inhibitors of the enzyme ikk-2 | |
| JP2005511746A5 (enExample) | ||
| JP2006524248A5 (enExample) | ||
| JP2007500226A5 (enExample) | ||
| JP2008524119A5 (enExample) | ||
| RU2350609C2 (ru) | Производные бензофурана и бензотиофена, применяемые при лечении гиперпролиферативных заболеваний | |
| RU2007114080A (ru) | N-бензилсульфонил-замещенные аналоги анилинопиримидина | |
| RU2007107349A (ru) | Пиперазиновые производные, применение для лечения желудочно-кишечных расстройств | |
| JP2005505586A5 (enExample) | ||
| JP2005538955A5 (enExample) | ||
| JP2008509982A5 (enExample) | ||
| RU2005109561A (ru) | Новые производные аминоиндазолов в качестве лекарственных средств и содержащие их фармацевтические композиции | |
| RU2004122407A (ru) | Амидные производные в качестве активаторов gk |