JP2005533004A5 - - Google Patents
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- 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
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- 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
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- 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
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- 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
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- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 125000005504 styryl group Chemical group 0.000 claims 1
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| 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 |
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| 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 |
| 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 |
| EP1778669A2 (en) | 2004-08-18 | 2007-05-02 | Takeda San Diego, Inc. | Kinase inhibitors |
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| SE0402762D0 (sv) * | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Indazole sulphonamide derivatives |
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| CN101243051A (zh) * | 2005-08-25 | 2008-08-13 | 霍夫曼-拉罗奇有限公司 | p38 MAP激酶抑制剂及使用它的方法 |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
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| 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 |
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| FR2917735B1 (fr) * | 2007-06-21 | 2009-09-04 | Sanofi Aventis Sa | Nouveaux indazoles substitutes, leur preparation et leur utilisation en therapeutique |
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| 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 |
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| PT2643322T (pt) | 2010-11-23 | 2017-11-13 | Abbvie Inc | Sais e formas cristalinas de um agente indutor de apoptose |
| US20140275082A1 (en) | 2013-03-14 | 2014-09-18 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| RU2719446C2 (ru) | 2014-11-03 | 2020-04-17 | Айомет Фарма Лтд | Фармацевтическое соединение |
| GB201511382D0 (en) | 2015-06-29 | 2015-08-12 | Imp Innovations Ltd | Novel compounds and their use in therapy |
| EA202090304A1 (ru) * | 2017-07-21 | 2020-06-25 | Кадмон Корпорейшн, Ллк | ИНГИБИТОРЫ Rho-АССОЦИИРОВАННОЙ, СОДЕРЖАЩЕЙ СУПЕРСПИРАЛЬ ПРОТЕИНКИНАЗЫ |
| EP3676255B1 (en) | 2017-08-29 | 2025-04-16 | Rutgers, The State University University Of New Jersey | Therapeutic indazoles |
| UY39892A (es) | 2021-08-10 | 2023-03-31 | Novartis Pharma Ag | Compuestos y composiciones para tratar afecciones asociadas con la actividad de STING |
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| WO2023165571A1 (zh) | 2022-03-04 | 2023-09-07 | 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 |
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| JPS514505Y2 (https=) | 1971-02-13 | 1976-02-07 | ||
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| DE69724777T2 (de) | 1996-02-22 | 2004-07-15 | Tularik, Inc., South San Francisco | Pentafluorobenzensulfonamiden und analoge |
| PT939627E (pt) * | 1996-07-19 | 2004-02-27 | Tularik Inc | Pentafluorobenzenossulfonamidas e analogos |
| 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 |
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| 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 |
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| CN1300116C (zh) * | 2001-04-16 | 2007-02-14 | 卫材株式会社 | 1h－吲唑化合物 |
| JPWO2002100833A1 (ja) | 2001-06-12 | 2004-09-24 | 住友製薬株式会社 | Ｒｈｏキナーゼ阻害剤 |
| US7064215B2 (en) * | 2001-07-03 | 2006-06-20 | Chiron Corporation | Indazole benzimidazole compounds |
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| 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 |
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- 2003-03-07 CA CA002478540A patent/CA2478540A1/fr not_active Abandoned
- 2003-03-07 OA OA1200400236A patent/OA12784A/fr unknown
- 2003-03-07 EP EP03744395A patent/EP1487803A1/fr not_active Withdrawn
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