KR20040091128A - 항암 활성을 갖는 치환된 인다졸 - Google Patents
항암 활성을 갖는 치환된 인다졸 Download PDFInfo
- Publication number
- KR20040091128A KR20040091128A KR10-2004-7014298A KR20047014298A KR20040091128A KR 20040091128 A KR20040091128 A KR 20040091128A KR 20047014298 A KR20047014298 A KR 20047014298A KR 20040091128 A KR20040091128 A KR 20040091128A
- Authority
- KR
- South Korea
- Prior art keywords
- indazol
- benzenesulfonamide
- phenyl
- methanesulfonylbenzenesulfonamide
- methylsulfonylbenzenesulfonamide
- 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.)
- Ceased
Links
- 150000002473 indoazoles Chemical group 0.000 title abstract 3
- 230000001093 anti-cancer Effects 0.000 title description 5
- 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 44
- 102000020233 phosphotransferase Human genes 0.000 claims abstract description 44
- -1 heterocycle Aryl Chemical group 0.000 claims description 166
- 150000001875 compounds Chemical class 0.000 claims description 158
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000002947 alkylene group Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 206010028980 Neoplasm Diseases 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003107 substituted aryl group Chemical group 0.000 claims description 17
- 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 108090000461 Aurora Kinase A Proteins 0.000 claims description 15
- 102100032311 Aurora kinase A Human genes 0.000 claims description 15
- 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 15
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 13
- 101150001535 SRC gene Proteins 0.000 claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 11
- 239000005711 Benzoic acid Substances 0.000 claims description 10
- 235000010233 benzoic acid Nutrition 0.000 claims description 10
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 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
- 229910052705 radium Inorganic materials 0.000 claims description 8
- 229910052701 rubidium Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 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 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims description 7
- 102100036239 Cyclin-dependent kinase 2 Human genes 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 Inorganic materials 0.000 claims description 7
- 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 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
- 229910052757 nitrogen Inorganic materials 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
- 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
- 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
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims description 6
- 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000003814 drug Substances 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
- 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
- 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 6
- LOVSSJYJNHKBJF-UHFFFAOYSA-N n-(3-cyano-1h-indazol-5-yl)-3-fluorobenzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(C#N)=NNC3=CC=2)=C1 LOVSSJYJNHKBJF-UHFFFAOYSA-N 0.000 claims description 6
- 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
- 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
- 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 6
- 229910052760 oxygen Inorganic materials 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
- 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
- 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
- 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 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
- 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 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
- 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
- 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
- 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 5
- 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 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
- 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 5
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- 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
- 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
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 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 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
- 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
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Classifications
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- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (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 (3)
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|---|---|---|---|
| FR0202996A FR2836914B1 (fr) | 2002-03-11 | 2002-03-11 | Indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
| FR02/02996 | 2002-03-11 | ||
| PCT/FR2003/000751 WO2003078402A1 (fr) | 2002-03-11 | 2003-03-07 | Indazoles substitues avec une activite anticancereuse |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040091128A true KR20040091128A (ko) | 2004-10-27 |
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| CA (1) | CA2478540A1 (enExample) |
| EC (1) | ECSP045286A (enExample) |
| FR (1) | FR2836914B1 (enExample) |
| GT (1) | GT200300031A (enExample) |
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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 |
| 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 |
| JP2007514759A (ja) | 2003-12-19 | 2007-06-07 | 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 |
| 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 |
| 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 |
| BRPI0515931A (pt) * | 2004-09-29 | 2008-08-12 | Hoffmann La Roche | compostos, processo para a sua preparação, composições farmacêuticas que os compreendem, método para o tratamento e/ou profilaxia de enfermidades e utilização desses compostos |
| DE602005023333D1 (de) | 2004-10-15 | 2010-10-14 | Takeda Pharmaceutical | Kinaseinhibitoren |
| 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 |
| KR20080031460A (ko) * | 2005-08-25 | 2008-04-08 | 에프. 호프만-라 로슈 아게 | Ｐ38 ｍａｐ 키나아제 저해제 및 이의 사용 방법 |
| 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 |
| BRPI0719883A2 (pt) | 2006-10-09 | 2015-05-05 | Takeda Pharmaceutical | Inibidores de quinase |
| 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 |
| EP2170834B1 (en) | 2007-07-16 | 2014-01-08 | AbbVie Inc. | Indazoles, benzisoxazoles and benzisothiazoles as inhibitors of protein kinases |
| 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 |
| RU2535347C3 (ru) * | 2009-05-26 | 2019-05-14 | ЭббВи Айэленд Анлимитед Компани | Индуцирующие апоптоз средства для лечения злокачественной опухоли и иммунных и аутоиммунных заболеваний |
| 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 |
| PT2642999T (pt) | 2010-11-23 | 2017-01-05 | Abbvie Ireland Unlimited Co | Métodos de tratamento que utilizam inibidores seletivos de bcl-2 |
| WO2012071336A1 (en) | 2010-11-23 | 2012-05-31 | Abbott Laboratories | 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 |
| CA2965741C (en) * | 2014-11-03 | 2022-05-17 | Iomet Pharma Ltd | Pharmaceutical compound |
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| US6482860B1 (en) * | 1996-07-19 | 2002-11-19 | Tularik Inc. | Pentafluorobenzenesulfonamides and analogs |
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