JP2013507397A5 - - Google Patents

Info

Publication number

JP2013507397A5

JP2013507397A5 JP2012533376A JP2012533376A JP2013507397A5 JP 2013507397 A5 JP2013507397 A5 JP 2013507397A5 JP 2012533376 A JP2012533376 A JP 2012533376A JP 2012533376 A JP2012533376 A JP 2012533376A JP 2013507397 A5 JP2013507397 A5 JP 2013507397A5

Authority

JP

Japan

Prior art keywords

thiazolidine

benzylidene

dione

pharmaceutical composition

methyl

Prior art date

2010-10-11

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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• -1 amino, methyl Chemical group 0.000 claims description 83
• 150000001875 compounds Chemical class 0.000 claims description 46
• 239000008194 pharmaceutical composition Substances 0.000 claims description 43
• 125000000217 alkyl group Chemical group 0.000 claims description 30
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 28
• 150000002431 hydrogen Chemical group 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 125000005843 halogen group Chemical group 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 150000001467 thiazolidinediones Chemical class 0.000 claims description 9
• 206010028980 Neoplasm Diseases 0.000 claims description 8
• 201000011510 cancer Diseases 0.000 claims description 8
• 230000034659 glycolysis Effects 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
• LUWDHPGEGGQSDG-UHFFFAOYSA-N 4-methoxy-N-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1C=C1C(=O)N(CC2(C)CCCCC2)C(=O)S1 LUWDHPGEGGQSDG-UHFFFAOYSA-N 0.000 claims description 6
• DKGMGNBUZOAOCL-UHFFFAOYSA-N 5-[[3-bromo-4-[(6-ethoxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CC2=C(C)C(OCC)=C(C)C(C)=C2OC1(C)COC(C(=C1)Br)=CC=C1C=C1SC(=O)NC1=O DKGMGNBUZOAOCL-UHFFFAOYSA-N 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000001188 haloalkyl group Chemical group 0.000 claims description 6
• FANMQRSNMHKZCR-UHFFFAOYSA-N n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]-4-nitro-3-(trifluoromethyl)benzenesulfonamide Chemical compound O=C1SC(=CC=2C=CC(NS(=O)(=O)C=3C=C(C(=CC=3)[N+]([O-])=O)C(F)(F)F)=CC=2)C(=O)N1CC1(C)CCCCC1 FANMQRSNMHKZCR-UHFFFAOYSA-N 0.000 claims description 6
• 125000002528 4-isopropyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• MADFJWDIMPOGOZ-UHFFFAOYSA-N 5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-3-[(1-methylcyclohexyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound O=C1SC(=CC=2C=C(C(O)=CC=2)C(F)(F)F)C(=O)N1CC1(C)CCCCC1 MADFJWDIMPOGOZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• WLUKQYQUWXIKFA-UHFFFAOYSA-N CC(C1=CC=CC=C1)=C1C(N(C(S1)=O)CCC)=O Chemical compound CC(C1=CC=CC=C1)=C1C(N(C(S1)=O)CCC)=O WLUKQYQUWXIKFA-UHFFFAOYSA-N 0.000 claims description 3
• 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 2
• 102000014156 AMP-Activated Protein Kinases Human genes 0.000 claims description 2
• 108010011376 AMP-Activated Protein Kinases Proteins 0.000 claims description 2
• TZAHCHGLQAMISI-IUXPMGMMSA-N BrC=1C=C(\C=C/2\CN(CS2)CC(CCC)CC)C=C(C1)Br Chemical compound BrC=1C=C(\C=C/2\CN(CS2)CC(CCC)CC)C=C(C1)Br TZAHCHGLQAMISI-IUXPMGMMSA-N 0.000 claims description 2
• 102000004889 Interleukin-6 Human genes 0.000 claims description 2
• 108090001005 Interleukin-6 Proteins 0.000 claims description 2
• 230000003213 activating effect Effects 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• 125000001072 heteroaryl group Chemical group 0.000 claims description 2
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
• 125000006178 methyl benzyl group Chemical group 0.000 claims description 2
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
• 239000000203 mixture Substances 0.000 claims 4
• 239000003814 drug Substances 0.000 claims 3
• QFYXSLAAXZTRLG-UHFFFAOYSA-N pyrrolidine-2,3-dione Chemical class O=C1CCNC1=O QFYXSLAAXZTRLG-UHFFFAOYSA-N 0.000 claims 1
• 0 *c(ccc(S(Nc1ccc(C=C(C(N2*)=O)SC2=O)cc1)(=O)=O)c1)c1I Chemical compound *c(ccc(S(Nc1ccc(C=C(C(N2*)=O)SC2=O)cc1)(=O)=O)c1)c1I 0.000 description 2