JP2007513877A5 - - Google Patents
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- Publication number
- JP2007513877A5 JP2007513877A5 JP2006539731A JP2006539731A JP2007513877A5 JP 2007513877 A5 JP2007513877 A5 JP 2007513877A5 JP 2006539731 A JP2006539731 A JP 2006539731A JP 2006539731 A JP2006539731 A JP 2006539731A JP 2007513877 A5 JP2007513877 A5 JP 2007513877A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- sulfinyl
- ethene
- chlorophenyl
- methoxyphenyl
- 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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- 150000001875 compounds Chemical class 0.000 claims description 74
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 43
- -1 2-imidazolyl Chemical group 0.000 claims description 32
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001151 peptidyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 230000002062 proliferating effect Effects 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- FUYCMDYFBXORQE-ZHACJKMWSA-N 1-[(e)-2-benzylsulfinylethenyl]-2-chlorobenzene Chemical compound ClC1=CC=CC=C1\C=C\S(=O)CC1=CC=CC=C1 FUYCMDYFBXORQE-ZHACJKMWSA-N 0.000 claims description 2
- JAWZDODXNRUZSP-MDZDMXLPSA-N 1-chloro-4-[[(e)-2-(4-chlorophenyl)ethenyl]sulfinylmethyl]benzene Chemical compound C1=CC(Cl)=CC=C1CS(=O)\C=C\C1=CC=C(Cl)C=C1 JAWZDODXNRUZSP-MDZDMXLPSA-N 0.000 claims description 2
- ASEKJCQKVZEWNW-MDZDMXLPSA-N 1-chloro-4-[[(e)-2-(4-fluorophenyl)ethenyl]sulfinylmethyl]benzene Chemical compound C1=CC(F)=CC=C1\C=C\S(=O)CC1=CC=C(Cl)C=C1 ASEKJCQKVZEWNW-MDZDMXLPSA-N 0.000 claims description 2
- PQBUVVWUDJFFPW-MDZDMXLPSA-N 1-fluoro-4-[[(e)-2-(4-fluorophenyl)ethenyl]sulfinylmethyl]benzene Chemical compound C1=CC(F)=CC=C1CS(=O)\C=C\C1=CC=C(F)C=C1 PQBUVVWUDJFFPW-MDZDMXLPSA-N 0.000 claims description 2
- KKPHLVVTRMKCLI-BQYQJAHWSA-N 2,4-difluoro-1-[(e)-2-[(4-fluorophenyl)methylsulfinyl]ethenyl]benzene Chemical compound C1=CC(F)=CC=C1CS(=O)\C=C\C1=CC=C(F)C=C1F KKPHLVVTRMKCLI-BQYQJAHWSA-N 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 31
- RBTBELHGVGPIBC-BQYQJAHWSA-N 1,2-dichloro-4-[(e)-2-[(4-chlorophenyl)methylsulfinyl]ethenyl]benzene Chemical compound C1=CC(Cl)=CC=C1CS(=O)\C=C\C1=CC=C(Cl)C(Cl)=C1 RBTBELHGVGPIBC-BQYQJAHWSA-N 0.000 claims 11
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 7
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 6
- 150000003462 sulfoxides Chemical class 0.000 claims 6
- 229920002554 vinyl polymer Polymers 0.000 claims 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 239000007795 chemical reaction product Substances 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 3
- PDXXCSZGKONJHN-MDZDMXLPSA-N 1-bromo-4-[[(e)-2-(4-chlorophenyl)ethenyl]sulfinylmethyl]benzene Chemical compound C1=CC(Cl)=CC=C1\C=C\S(=O)CC1=CC=C(Br)C=C1 PDXXCSZGKONJHN-MDZDMXLPSA-N 0.000 claims 2
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 claims 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- WBAKGKVJTHNGBX-VQHVLOKHSA-N 2-[(e)-2-[(4-bromophenyl)methylsulfinyl]ethenyl]furan Chemical compound C1=CC(Br)=CC=C1CS(=O)\C=C\C1=CC=CO1 WBAKGKVJTHNGBX-VQHVLOKHSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000005865 ionizing radiation Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 claims 2
- JOBKDFZYYWNWIV-JGXDSNKPSA-N (2r)-2-amino-3-hydroxy-n-[2-methoxy-5-[[(e)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfinylmethyl]phenyl]propanamide Chemical compound COC1=CC(OC)=CC(OC)=C1\C=C\S(=O)CC1=CC=C(OC)C(NC(=O)[C@H](N)CO)=C1 JOBKDFZYYWNWIV-JGXDSNKPSA-N 0.000 claims 1
- JOBKDFZYYWNWIV-LXUZMOMUSA-N (2s)-2-amino-3-hydroxy-n-[2-methoxy-5-[[(e)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfinylmethyl]phenyl]propanamide Chemical compound COC1=CC(OC)=CC(OC)=C1\C=C\S(=O)CC1=CC=C(OC)C(NC(=O)[C@@H](N)CO)=C1 JOBKDFZYYWNWIV-LXUZMOMUSA-N 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- GDIPCNUDYQWUOS-AATRIKPKSA-N 1,2,3,4,5-pentafluoro-6-[(e)-2-[(4-fluorophenyl)methylsulfinyl]ethenyl]benzene Chemical compound C1=CC(F)=CC=C1CS(=O)\C=C\C1=C(F)C(F)=C(F)C(F)=C1F GDIPCNUDYQWUOS-AATRIKPKSA-N 0.000 claims 1
- DAQBVOGRGJTPCI-AATRIKPKSA-N 1,2,3,4,5-pentafluoro-6-[(e)-2-[(4-iodophenyl)methylsulfinyl]ethenyl]benzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1\C=C\S(=O)CC1=CC=C(I)C=C1 DAQBVOGRGJTPCI-AATRIKPKSA-N 0.000 claims 1
- BUFVSMMJRYMHJH-VAWYXSNFSA-N 1,2,3-trimethoxy-4-[(e)-2-[(4-methoxyphenyl)methylsulfinyl]ethenyl]benzene Chemical compound C1=CC(OC)=CC=C1CS(=O)\C=C\C1=CC=C(OC)C(OC)=C1OC BUFVSMMJRYMHJH-VAWYXSNFSA-N 0.000 claims 1
- UFYGUEAEZBRXCT-VOTSOKGWSA-N 1,2,4,5-tetrafluoro-3-[(e)-2-[(4-methoxyphenyl)methylsulfinyl]ethenyl]benzene Chemical compound C1=CC(OC)=CC=C1CS(=O)\C=C\C1=C(F)C(F)=CC(F)=C1F UFYGUEAEZBRXCT-VOTSOKGWSA-N 0.000 claims 1
- QHTVHFAOAMRXEG-MDZDMXLPSA-N 1,2,4-trimethoxy-5-[(e)-2-[(4-methoxyphenyl)methylsulfinyl]ethenyl]benzene Chemical compound C1=CC(OC)=CC=C1CS(=O)\C=C\C1=CC(OC)=C(OC)C=C1OC QHTVHFAOAMRXEG-MDZDMXLPSA-N 0.000 claims 1
- RBHBDKPYJBROFN-CMDGGOBGSA-N 1,2-dichloro-3-[(e)-2-[(4-chlorophenyl)methylsulfinyl]ethenyl]benzene Chemical compound C1=CC(Cl)=CC=C1CS(=O)\C=C\C1=CC=CC(Cl)=C1Cl RBHBDKPYJBROFN-CMDGGOBGSA-N 0.000 claims 1
- HEXXRZOWCCEPOZ-BQYQJAHWSA-N 1,2-dichloro-4-[[(e)-2-(4-chlorophenyl)ethenyl]sulfinylmethyl]benzene Chemical compound C1=CC(Cl)=CC=C1\C=C\S(=O)CC1=CC=C(Cl)C(Cl)=C1 HEXXRZOWCCEPOZ-BQYQJAHWSA-N 0.000 claims 1
- VWOQTBSHQNJFPR-BQYQJAHWSA-N 1,2-dichloro-4-[[(e)-2-(4-fluorophenyl)ethenyl]sulfinylmethyl]benzene Chemical compound C1=CC(F)=CC=C1\C=C\S(=O)CC1=CC=C(Cl)C(Cl)=C1 VWOQTBSHQNJFPR-BQYQJAHWSA-N 0.000 claims 1
- NZHMXHXULYHYLC-CMDGGOBGSA-N 1,2-dimethoxy-4-[(e)-2-[(4-methoxyphenyl)methylsulfinyl]ethenyl]-5-nitrobenzene Chemical compound C1=CC(OC)=CC=C1CS(=O)\C=C\C1=CC(OC)=C(OC)C=C1[N+]([O-])=O NZHMXHXULYHYLC-CMDGGOBGSA-N 0.000 claims 1
- VDTUOTNUJFJOFE-MDZDMXLPSA-N 1,3,5-trimethoxy-2-[(e)-2-[(4-methoxyphenyl)methylsulfinyl]ethenyl]benzene Chemical compound C1=CC(OC)=CC=C1CS(=O)\C=C\C1=C(OC)C=C(OC)C=C1OC VDTUOTNUJFJOFE-MDZDMXLPSA-N 0.000 claims 1
- WHJRUOVKUWSOBT-BQYQJAHWSA-N 1-[(e)-2-[(4-bromophenyl)methylsulfinyl]ethenyl]-2,4-difluorobenzene Chemical compound FC1=CC(F)=CC=C1\C=C\S(=O)CC1=CC=C(Br)C=C1 WHJRUOVKUWSOBT-BQYQJAHWSA-N 0.000 claims 1
- LEFYSPKGRMSRMC-MDZDMXLPSA-N 1-[(e)-2-[(4-bromophenyl)methylsulfinyl]ethenyl]-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1\C=C\S(=O)CC1=CC=C(Br)C=C1 LEFYSPKGRMSRMC-MDZDMXLPSA-N 0.000 claims 1
- LXHFKZMJJQYWLF-MDZDMXLPSA-N 1-[(e)-2-[(4-bromophenyl)methylsulfinyl]ethenyl]-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1\C=C\S(=O)CC1=CC=C(Br)C=C1 LXHFKZMJJQYWLF-MDZDMXLPSA-N 0.000 claims 1
- JCTJJPCDTVPWGN-CMDGGOBGSA-N 1-[(e)-2-[(4-bromophenyl)methylsulfinyl]ethenyl]-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(\C=C\S(=O)CC=2C=CC(Br)=CC=2)=C1 JCTJJPCDTVPWGN-CMDGGOBGSA-N 0.000 claims 1
- LWZOPRYKNZWDCX-AATRIKPKSA-N 1-[(e)-2-[(4-chlorophenyl)methylsulfinyl]ethenyl]-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1\C=C\S(=O)CC1=CC=C(Cl)C=C1 LWZOPRYKNZWDCX-AATRIKPKSA-N 0.000 claims 1
- WZFLFLKBSOBJHN-BQYQJAHWSA-N 1-[(e)-2-[(4-chlorophenyl)methylsulfinyl]ethenyl]-2,3,4-trifluorobenzene Chemical compound FC1=C(F)C(F)=CC=C1\C=C\S(=O)CC1=CC=C(Cl)C=C1 WZFLFLKBSOBJHN-BQYQJAHWSA-N 0.000 claims 1
- PRRGVZUNONLDNC-MDZDMXLPSA-N 1-[(e)-2-[(4-chlorophenyl)methylsulfinyl]ethenyl]-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1\C=C\S(=O)CC1=CC=C(Cl)C=C1 PRRGVZUNONLDNC-MDZDMXLPSA-N 0.000 claims 1
- VWBFGNMOZXIKSI-MDZDMXLPSA-N 1-[(e)-2-[(4-chlorophenyl)methylsulfinyl]ethenyl]-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1\C=C\S(=O)CC1=CC=C(Cl)C=C1 VWBFGNMOZXIKSI-MDZDMXLPSA-N 0.000 claims 1
- QSFJWQVLRPTPMM-CMDGGOBGSA-N 1-[(e)-2-[(4-chlorophenyl)methylsulfinyl]ethenyl]-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(\C=C\S(=O)CC=2C=CC(Cl)=CC=2)=C1 QSFJWQVLRPTPMM-CMDGGOBGSA-N 0.000 claims 1
- SSASOYGSEMXWES-CMDGGOBGSA-N 1-[(e)-2-[(4-chlorophenyl)methylsulfinyl]ethenyl]-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(\C=C\S(=O)CC=2C=CC(Cl)=CC=2)=C1 SSASOYGSEMXWES-CMDGGOBGSA-N 0.000 claims 1
- CKQZUXOVSDWREV-BQYQJAHWSA-N 1-[(e)-2-[(4-chlorophenyl)methylsulfinyl]ethenyl]-4-fluoro-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(F)=CC=C1\C=C\S(=O)CC1=CC=C(Cl)C=C1 CKQZUXOVSDWREV-BQYQJAHWSA-N 0.000 claims 1
- UIRNWOCKMDNTTB-MDZDMXLPSA-N 1-[(e)-2-[(4-fluorophenyl)methylsulfinyl]ethenyl]-2-(trifluoromethyl)benzene Chemical compound C1=CC(F)=CC=C1CS(=O)\C=C\C1=CC=CC=C1C(F)(F)F UIRNWOCKMDNTTB-MDZDMXLPSA-N 0.000 claims 1
- OYHLFAFLWZYBGF-MDZDMXLPSA-N 1-[(e)-2-[(4-fluorophenyl)methylsulfinyl]ethenyl]-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1\C=C\S(=O)CC1=CC=C(F)C=C1 OYHLFAFLWZYBGF-MDZDMXLPSA-N 0.000 claims 1
- FJVMVHIWCIZWCF-CMDGGOBGSA-N 1-[(e)-2-[(4-fluorophenyl)methylsulfinyl]ethenyl]-3-(trifluoromethyl)benzene Chemical compound C1=CC(F)=CC=C1CS(=O)\C=C\C1=CC=CC(C(F)(F)F)=C1 FJVMVHIWCIZWCF-CMDGGOBGSA-N 0.000 claims 1
- RRLGUPGKFXMLTG-CMDGGOBGSA-N 1-[(e)-2-[(4-fluorophenyl)methylsulfinyl]ethenyl]-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(\C=C\S(=O)CC=2C=CC(F)=CC=2)=C1 RRLGUPGKFXMLTG-CMDGGOBGSA-N 0.000 claims 1
- JTTYGYPGZSWXKD-MDZDMXLPSA-N 1-[(e)-2-[(4-iodophenyl)methylsulfinyl]ethenyl]-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1\C=C\S(=O)CC1=CC=C(I)C=C1 JTTYGYPGZSWXKD-MDZDMXLPSA-N 0.000 claims 1
- XZOPBMJPTPAVQN-ZHACJKMWSA-N 1-[(e)-2-[(4-methylphenyl)methylsulfinyl]ethenyl]-2-nitrobenzene Chemical compound C1=CC(C)=CC=C1CS(=O)\C=C\C1=CC=CC=C1[N+]([O-])=O XZOPBMJPTPAVQN-ZHACJKMWSA-N 0.000 claims 1
- KGLVNFLYJUOPBG-ZHACJKMWSA-N 1-[(e)-2-benzylsulfinylethenyl]-4-chlorobenzene Chemical compound C1=CC(Cl)=CC=C1\C=C\S(=O)CC1=CC=CC=C1 KGLVNFLYJUOPBG-ZHACJKMWSA-N 0.000 claims 1
- QVSDGVRDGXKFDM-KHPPLWFESA-N 1-[(z)-2-[(4-fluorophenyl)methylsulfinyl]ethenyl]-4-methylbenzene Chemical compound C1=CC(C)=CC=C1\C=C/S(=O)CC1=CC=C(F)C=C1 QVSDGVRDGXKFDM-KHPPLWFESA-N 0.000 claims 1
- QFLOEICMSGNVAY-KHPPLWFESA-N 1-[(z)-2-benzylsulfinylethenyl]-4-bromobenzene Chemical compound C1=CC(Br)=CC=C1\C=C/S(=O)CC1=CC=CC=C1 QFLOEICMSGNVAY-KHPPLWFESA-N 0.000 claims 1
- DZVBOSXRVDQRGA-KHPPLWFESA-N 1-[(z)-2-benzylsulfinylethenyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1\C=C/S(=O)CC1=CC=CC=C1 DZVBOSXRVDQRGA-KHPPLWFESA-N 0.000 claims 1
- YHBYZEAXOULBKJ-OUKQBFOZSA-N 1-[[(e)-2-(2-nitrophenyl)ethenyl]sulfinylmethyl]naphthalene Chemical compound [O-][N+](=O)C1=CC=CC=C1\C=C\S(=O)CC1=CC=CC2=CC=CC=C12 YHBYZEAXOULBKJ-OUKQBFOZSA-N 0.000 claims 1
- XVHXJRBAWYKSCH-VAWYXSNFSA-N 1-[[(e)-2-(3-nitrophenyl)ethenyl]sulfinylmethyl]naphthalene Chemical compound [O-][N+](=O)C1=CC=CC(\C=C\S(=O)CC=2C3=CC=CC=C3C=CC=2)=C1 XVHXJRBAWYKSCH-VAWYXSNFSA-N 0.000 claims 1
- WEWBTLMGZRJAHQ-AATRIKPKSA-N 1-[[(e)-2-(4-bromophenyl)ethenyl]sulfinylmethyl]-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1CS(=O)\C=C\C1=CC=C(Br)C=C1 WEWBTLMGZRJAHQ-AATRIKPKSA-N 0.000 claims 1
- JYAIBVDTSIIRSH-MDZDMXLPSA-N 1-[[(e)-2-(4-bromophenyl)ethenyl]sulfinylmethyl]-4-(trifluoromethyl)benzene Chemical compound C1=CC(C(F)(F)F)=CC=C1CS(=O)\C=C\C1=CC=C(Br)C=C1 JYAIBVDTSIIRSH-MDZDMXLPSA-N 0.000 claims 1
- JESYEDRKXYIOPH-MDZDMXLPSA-N 1-[[(e)-2-(4-bromophenyl)ethenyl]sulfinylmethyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1CS(=O)\C=C\C1=CC=C(Br)C=C1 JESYEDRKXYIOPH-MDZDMXLPSA-N 0.000 claims 1
- IBEGWVJDNNKCPN-ZHACJKMWSA-N 1-[[(e)-2-(4-bromophenyl)ethenyl]sulfinylmethyl]-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1CS(=O)\C=C\C1=CC=C(Br)C=C1 IBEGWVJDNNKCPN-ZHACJKMWSA-N 0.000 claims 1
- CQHNBSGQBCNGNK-ZHACJKMWSA-N 1-[[(e)-2-(4-bromophenyl)ethenyl]sulfinylmethyl]-4-methylbenzene Chemical compound C1=CC(C)=CC=C1CS(=O)\C=C\C1=CC=C(Br)C=C1 CQHNBSGQBCNGNK-ZHACJKMWSA-N 0.000 claims 1
- YMHLVKDCEQQSMC-OUKQBFOZSA-N 1-[[(e)-2-(4-bromophenyl)ethenyl]sulfinylmethyl]naphthalene Chemical compound C1=CC(Br)=CC=C1\C=C\S(=O)CC1=CC=CC2=CC=CC=C12 YMHLVKDCEQQSMC-OUKQBFOZSA-N 0.000 claims 1
- DUTFXULNHUSNCY-AATRIKPKSA-N 1-[[(e)-2-(4-chlorophenyl)ethenyl]sulfinylmethyl]-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1CS(=O)\C=C\C1=CC=C(Cl)C=C1 DUTFXULNHUSNCY-AATRIKPKSA-N 0.000 claims 1
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| US60/520,523 | 2003-11-14 | ||
| PCT/US2004/037293 WO2005046599A2 (en) | 2003-11-14 | 2004-11-08 | Alpha, beta-unsaturated sulfoxides for treating proliferative disorders |
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| JP2007513877A JP2007513877A (ja) | 2007-05-31 |
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| JP5196787B2 JP5196787B2 (ja) | 2013-05-15 |
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| JP (1) | JP5196787B2 (enExample) |
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| WO (1) | WO2005046599A2 (enExample) |
Families Citing this family (12)
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| EP1740530B8 (en) * | 2004-03-16 | 2017-03-01 | Temple University - Of The Commonwealth System of Higher Education | Substituted phenoxy- and phenylthio-derivatives for treating proliferative disorders |
| EP1841420B1 (en) * | 2005-01-05 | 2011-12-07 | Temple University - Of The Commonwealth System of Higher Education | Treatment of drug-resistant proliferative disorders |
| US8106033B2 (en) * | 2005-03-11 | 2012-01-31 | Temple University - Of The Commonwealth System Of Higher Education | Composition and methods for the treatment of proliferative diseases |
| US20100080843A1 (en) * | 2005-06-30 | 2010-04-01 | The Research Foundation of the State University Of New York at Albany | Natural and synthetic sulfur and selenium analogs and polymer conjugated forms thereof for the modulation of angiogenesis |
| WO2010075026A2 (en) * | 2008-12-16 | 2010-07-01 | Onconova Therapeutics Inc | Methods for determining efficacy of a therapeutic regimen against deleterious effects of cytotoxic agents in human |
| GB201010359D0 (en) * | 2010-06-21 | 2010-08-04 | Univ Nottingham | Compounds for treating proliferative disorders |
| EP2486923B1 (en) * | 2011-02-11 | 2015-09-09 | Dr. Felix Jäger und Dr. Stefan Drinkuth Laborgemeinschaft OHG | Histone deacetylase (HDAC) inhibiting compounds and method of making same |
| CN110776447A (zh) | 2012-09-20 | 2020-02-11 | 坦普尔大学 | 取代的烷基二芳基衍生物、制备方法和用途 |
| JP2016523830A (ja) * | 2013-05-07 | 2016-08-12 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 放射線緩和薬学的配合物 |
| CN104892471B (zh) * | 2015-05-15 | 2020-03-27 | 中国人民解放军军事医学科学院放射与辐射医学研究所 | 具有蛋白酪氨酸激酶抑制活性的物质、其制备方法及用途 |
| US10383831B2 (en) * | 2015-08-03 | 2019-08-20 | Temple University—Of the Commonwealth System of Higher Education | 2,4,6-trialkoxystryl aryl sulfones, sulfonamides and carboxamides, and methods of preparation and use |
| CN106432011B (zh) * | 2016-09-18 | 2018-11-02 | 中国医学科学院放射医学研究所 | 一类具有辐射防护作用的新化合物、其制备方法及其药物应用 |
Family Cites Families (26)
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| US3865867A (en) * | 1967-06-19 | 1975-02-11 | Monsanto Co | Meta-bifunctional benzenes |
| US3975435A (en) * | 1974-03-06 | 1976-08-17 | Givaudan Corporation | Substituted cinnamanilides |
| GB1527109A (en) * | 1974-12-28 | 1978-10-04 | Asahi Chemical Ind | Cephalosporin derivatives and process for preparing same |
| JPH05262733A (ja) * | 1992-03-23 | 1993-10-12 | Sapporo Breweries Ltd | 含硫黄化合物，その製造法及びそれを有効成分とする抗潰瘍剤 |
| US5523302A (en) * | 1993-11-24 | 1996-06-04 | The Du Pont Merck Pharmaceutical Company | Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists |
| CN1287783C (zh) * | 1997-05-14 | 2006-12-06 | 阿特罗吉尼克斯公司 | 普罗布考单酯在制备用于治疗心血管疾病和炎性疾病的药物中的应用 |
| CZ299718B6 (cs) * | 1997-10-03 | 2008-10-29 | Temple University - Of The Commonwealth System Ofhigher Education | Styrylsulfonová sloucenina a farmaceutický prostredek ji obsahující |
| US6548553B2 (en) * | 1997-10-03 | 2003-04-15 | Temple University-Of The Commonwealth System Of Higher Education | Styryl sulfone anticancer agents |
| US6201154B1 (en) * | 1999-03-31 | 2001-03-13 | Temple University-Of The Commonwealth Of Higher Education | Z-styryl sulfone anticancer agents |
| US6762207B1 (en) * | 1999-04-02 | 2004-07-13 | Temple University - Of The Commonwealth System Of Higher Education | (E)-styryl sulfone anticancer agents |
| JP4596651B2 (ja) * | 1999-04-02 | 2010-12-08 | テンプル・ユニバーシティ−オブ・ザ・コモンウェルス・システム・オブ・ハイアー・エデュケイション | （ｅ）−スチリルスルホン抗癌剤 |
| AU3381399A (en) * | 1999-04-02 | 2000-10-23 | Temple University - Of The Commonwealth System Of Higher Education | Styryl sulfone anticancer agents |
| US6117364A (en) * | 1999-05-27 | 2000-09-12 | Nalco/Exxon Energy Chemicals, L.P. | Acid corrosion inhibitor |
| WO2000077169A2 (en) * | 1999-06-16 | 2000-12-21 | Temple University - Of The Commonwealth System Of Higher Education | (z)-styryl acetoxyphenyl sulfides as cyclooxygenase inhibitors |
| US6767926B1 (en) * | 1999-10-12 | 2004-07-27 | Temple University - Of The Commonwealth System Of Higher Education | Method for protecting normal cells from cytotoxicity of chemotherapeutic agents |
| AU780844B2 (en) * | 1999-10-12 | 2005-04-21 | Temple University-Of The Commonwealth System Of Higher Education | Method for protecting normal cells from cytotoxicity of chemotherapeutic agents |
| US6486210B2 (en) * | 2000-04-14 | 2002-11-26 | Temple University—Of the Commonwealth System of Higher Education | Substituted styryl benzylsulfones for treating proliferative disorders |
| US6541475B2 (en) * | 2000-04-14 | 2003-04-01 | Temple University - Of The Commonwealth System Of Higher Education | α, β-unsaturated sulfones for treating proliferative disorders |
| WO2002028828A1 (en) * | 2000-10-05 | 2002-04-11 | Temple University - Of The Commonwealth System Of Higher Education | Substituted (e)-styryl benzylsulfones for treating proliferative disorders |
| EP1493913B1 (en) * | 2000-10-12 | 2005-12-28 | Yamaha Hatsudoki Kabushiki Kaisha | Fuel gas mixer |
| US6833480B2 (en) * | 2001-02-27 | 2004-12-21 | Temple University - Of The Commonwealth System Of Higher Education | (Z)-styrylbenzylsulfones and pharmaceutical uses thereof |
| JP4302986B2 (ja) * | 2001-02-28 | 2009-07-29 | テンプル・ユニバーシティ−オブ・ザ・コモンウェルス・システム・オブ・ハイアー・エデュケイション | 細胞及び組織をα，β不飽和アリールスルホンにより電離放射線から防護する方法 |
| CA2439255C (en) * | 2001-02-28 | 2011-01-04 | Temple University Of The Commonwealth System Of Higher Education | N-(aryl)-2-arylethenesulfonamides and therapeutic uses thereof |
| MXPA04008356A (es) * | 2002-02-28 | 2005-09-12 | Univ Temple | (e)-2,6-dialcoxiestiril bencilsulfonas sustituidas con un grupo amino y en la posicion 4 para tratar trastornos poliferativos. |
| EP1740530B8 (en) * | 2004-03-16 | 2017-03-01 | Temple University - Of The Commonwealth System of Higher Education | Substituted phenoxy- and phenylthio-derivatives for treating proliferative disorders |
| US8106033B2 (en) * | 2005-03-11 | 2012-01-31 | Temple University - Of The Commonwealth System Of Higher Education | Composition and methods for the treatment of proliferative diseases |
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2004
- 2004-11-08 US US10/574,993 patent/US7744889B2/en not_active Expired - Lifetime
- 2004-11-08 AU AU2004289281A patent/AU2004289281C1/en not_active Expired
- 2004-11-08 HU HUE04816944A patent/HUE032523T2/en unknown
- 2004-11-08 DK DK04816944.5T patent/DK1689706T3/da active
- 2004-11-08 JP JP2006539731A patent/JP5196787B2/ja not_active Expired - Fee Related
- 2004-11-08 KR KR1020067007327A patent/KR20060109871A/ko not_active Ceased
- 2004-11-08 CA CA2546495A patent/CA2546495C/en not_active Expired - Lifetime
- 2004-11-08 WO PCT/US2004/037293 patent/WO2005046599A2/en not_active Ceased
- 2004-11-08 NZ NZ545995A patent/NZ545995A/en not_active IP Right Cessation
- 2004-11-08 EP EP04816944.5A patent/EP1689706B1/en not_active Expired - Lifetime
- 2004-11-08 ES ES04816944.5T patent/ES2621802T3/es not_active Expired - Lifetime
-
2006
- 2006-03-20 IL IL174426A patent/IL174426A/en active IP Right Grant
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