KR100768415B1 - 치환된 스티릴 벤질설폰, 이의 제조방법 및 이를 포함하는 증식성 장애 치료용 약제학적 조성물 - Google Patents
치환된 스티릴 벤질설폰, 이의 제조방법 및 이를 포함하는 증식성 장애 치료용 약제학적 조성물 Download PDFInfo
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- KR100768415B1 KR100768415B1 KR1020027013708A KR20027013708A KR100768415B1 KR 100768415 B1 KR100768415 B1 KR 100768415B1 KR 1020027013708 A KR1020027013708 A KR 1020027013708A KR 20027013708 A KR20027013708 A KR 20027013708A KR 100768415 B1 KR100768415 B1 KR 100768415B1
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- alkoxy
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- amino
- alkyl
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- -1 styryl benzyl sulfone Chemical class 0.000 title claims abstract description 239
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 230000002062 proliferating effect Effects 0.000 title description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 128
- 150000002367 halogens Chemical class 0.000 claims abstract description 128
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 81
- 239000001257 hydrogen Substances 0.000 claims abstract description 81
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 73
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 70
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 68
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 64
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 58
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 47
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 241000209140 Triticum Species 0.000 claims abstract description 19
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- 150000001875 compounds Chemical class 0.000 claims description 138
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
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- 201000011510 cancer Diseases 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 206010016654 Fibrosis Diseases 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- SBSLPPMPINEXNI-YDWXAUTNSA-N 1,2,3,4,5-pentafluoro-6-[(e)-3-(4-fluorophenyl)-1-[(e)-3-(4-fluorophenyl)-1-(2,3,4,5,6-pentafluorophenyl)prop-2-enyl]sulfonylprop-2-enyl]benzene Chemical compound C1=CC(F)=CC=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C=CC(F)=CC=1)C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F SBSLPPMPINEXNI-YDWXAUTNSA-N 0.000 claims description 2
- JYQVQRVNPTWWPZ-WGDLNXRISA-N 1,2,3,4,5-pentafluoro-6-[(e)-3-(4-fluorophenyl)-3-[(e)-1-(4-fluorophenyl)-3-(2,3,4,5,6-pentafluorophenyl)prop-2-enyl]sulfonylprop-1-enyl]benzene Chemical compound C1=CC(F)=CC=C1C(S(=O)(=O)C(\C=C\C=1C(=C(F)C(F)=C(F)C=1F)F)C=1C=CC(F)=CC=1)\C=C\C1=C(F)C(F)=C(F)C(F)=C1F JYQVQRVNPTWWPZ-WGDLNXRISA-N 0.000 claims description 2
- ZBFGDONTPUMMDC-WGDLNXRISA-N 1,2,3,4,5-pentafluoro-6-[(e)-3-(4-iodophenyl)-3-[(e)-1-(4-iodophenyl)-3-(2,3,4,5,6-pentafluorophenyl)prop-2-enyl]sulfonylprop-1-enyl]benzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C(=C(F)C(F)=C(F)C=1F)F)C=1C=CC(I)=CC=1)C1=CC=C(I)C=C1 ZBFGDONTPUMMDC-WGDLNXRISA-N 0.000 claims description 2
- YFQFBQIGRJQFFS-BGPOSVGRSA-N 1,2,3-trifluoro-4-[(e)-3-(4-fluorophenyl)-3-[(e)-1-(4-fluorophenyl)-3-(2,3,4-trifluorophenyl)prop-2-enyl]sulfonylprop-1-enyl]benzene Chemical compound C1=CC(F)=CC=C1C(S(=O)(=O)C(\C=C\C=1C(=C(F)C(F)=CC=1)F)C=1C=CC(F)=CC=1)\C=C\C1=CC=C(F)C(F)=C1F YFQFBQIGRJQFFS-BGPOSVGRSA-N 0.000 claims description 2
- LSQPHWBCMFQPAP-XPWSMXQVSA-N 1,3,5-trimethoxy-2-[(e)-3-(4-methoxyphenyl)-3-[(e)-1-(4-methoxyphenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-enyl]sulfonylprop-1-enyl]benzene Chemical compound C1=CC(OC)=CC=C1C(S(=O)(=O)C(\C=C\C=1C(=CC(OC)=CC=1OC)OC)C=1C=CC(OC)=CC=1)\C=C\C1=C(OC)C=C(OC)C=C1OC LSQPHWBCMFQPAP-XPWSMXQVSA-N 0.000 claims description 2
- PZGCQHVZLVMFTO-FCXRPNKRSA-N 1-[(e)-3-(3,4-dichlorophenyl)-3-[(e)-1-(3,4-dichlorophenyl)-3-(2,3,4,5,6-pentafluorophenyl)prop-2-enyl]sulfonylprop-1-enyl]-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C(=C(F)C(F)=C(F)C=1F)F)C=1C=C(Cl)C(Cl)=CC=1)C1=CC=C(Cl)C(Cl)=C1 PZGCQHVZLVMFTO-FCXRPNKRSA-N 0.000 claims description 2
- YLDNMXSNYYBDFG-YDWXAUTNSA-N 1-[(e)-3-(4-bromophenyl)-1-[(e)-3-(4-bromophenyl)-1-(2,3,4,5,6-pentafluorophenyl)prop-2-enyl]sulfonylprop-2-enyl]-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1C(S(=O)(=O)C(\C=C\C=1C=CC(Br)=CC=1)C=1C(=C(F)C(F)=C(F)C=1F)F)\C=C\C1=CC=C(Br)C=C1 YLDNMXSNYYBDFG-YDWXAUTNSA-N 0.000 claims description 2
- BZTPAQNCKKWIPD-WGDLNXRISA-N 1-[(e)-3-(4-bromophenyl)-3-[(e)-1-(4-bromophenyl)-3-(2,3,4,5,6-pentafluorophenyl)prop-2-enyl]sulfonylprop-1-enyl]-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C(=C(F)C(F)=C(F)C=1F)F)C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 BZTPAQNCKKWIPD-WGDLNXRISA-N 0.000 claims description 2
- LBRHQENFVSXKJM-YDWXAUTNSA-N 1-[(e)-3-(4-chlorophenyl)-1-[(e)-3-(4-chlorophenyl)-1-(2,3,4,5,6-pentafluorophenyl)prop-2-enyl]sulfonylprop-2-enyl]-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1C(S(=O)(=O)C(\C=C\C=1C=CC(Cl)=CC=1)C=1C(=C(F)C(F)=C(F)C=1F)F)\C=C\C1=CC=C(Cl)C=C1 LBRHQENFVSXKJM-YDWXAUTNSA-N 0.000 claims description 2
- OHLGBRUJXZLENF-WGDLNXRISA-N 1-[(e)-3-(4-chlorophenyl)-3-[(e)-1-(4-chlorophenyl)-3-(2,3,4,5,6-pentafluorophenyl)prop-2-enyl]sulfonylprop-1-enyl]-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C(=C(F)C(F)=C(F)C=1F)F)C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 OHLGBRUJXZLENF-WGDLNXRISA-N 0.000 claims description 2
- ASWIUWIUYBQFRE-BGPOSVGRSA-N 1-[(e)-3-(4-chlorophenyl)-3-[(e)-1-(4-chlorophenyl)-3-(2,3,4-trifluorophenyl)prop-2-enyl]sulfonylprop-1-enyl]-2,3,4-trifluorobenzene Chemical compound FC1=C(F)C(F)=CC=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C(=C(F)C(F)=CC=1)F)C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 ASWIUWIUYBQFRE-BGPOSVGRSA-N 0.000 claims description 2
- PBMCWLMEWFGPBX-ZPUQHVIOSA-N 1-[(e)-3-[(e)-1,3-bis(2,3,4,5,6-pentafluorophenyl)prop-2-enyl]sulfonyl-3-(2,3,4,5,6-pentafluorophenyl)prop-1-enyl]-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C(=C(F)C(F)=C(F)C=1F)F)C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F PBMCWLMEWFGPBX-ZPUQHVIOSA-N 0.000 claims description 2
- UYBARLRUHOODMT-JYFOCSDGSA-N 1-[(e)-3-[(e)-3-(4,5-dimethoxy-2-nitrophenyl)-1-(4-methoxyphenyl)prop-2-enyl]sulfonyl-3-(4-methoxyphenyl)prop-1-enyl]-4,5-dimethoxy-2-nitrobenzene Chemical compound C1=CC(OC)=CC=C1C(S(=O)(=O)C(\C=C\C=1C(=CC(OC)=C(OC)C=1)[N+]([O-])=O)C=1C=CC(OC)=CC=1)\C=C\C1=CC(OC)=C(OC)C=C1[N+]([O-])=O UYBARLRUHOODMT-JYFOCSDGSA-N 0.000 claims description 2
- IXKPKFXAOWLGBA-YTEMWHBBSA-N 2-[(e)-3-(4-bromophenyl)-3-[(e)-1-(4-bromophenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-enyl]sulfonylprop-1-enyl]-1,3,5-trimethoxybenzene Chemical compound COC1=CC(OC)=CC(OC)=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C(=CC(OC)=CC=1OC)OC)C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 IXKPKFXAOWLGBA-YTEMWHBBSA-N 0.000 claims description 2
- GMGWSYNUDNAELW-WXUKJITCSA-N 2-[(e)-3-(4-bromophenyl)-3-[(e)-1-(4-bromophenyl)-3-(4-fluoro-2,6-dimethoxyphenyl)prop-2-enyl]sulfonylprop-1-enyl]-5-fluoro-1,3-dimethoxybenzene Chemical compound COC1=CC(F)=CC(OC)=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C(=CC(F)=CC=1OC)OC)C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 GMGWSYNUDNAELW-WXUKJITCSA-N 0.000 claims description 2
- PNYMULXLZQBRJS-WXUKJITCSA-N 2-[(e)-3-(4-chlorophenyl)-3-[(e)-1-(4-chlorophenyl)-3-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-enyl]sulfonylprop-1-enyl]-3,5-dimethoxyphenol Chemical compound COC1=CC(OC)=CC(O)=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C(=CC(OC)=CC=1O)OC)C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 PNYMULXLZQBRJS-WXUKJITCSA-N 0.000 claims description 2
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- HOPUNXURSBBUQQ-YTEMWHBBSA-N 2-[(e)-3-[(e)-3-(2-hydroxy-4,6-dimethoxyphenyl)-1-(4-methoxyphenyl)prop-2-enyl]sulfonyl-3-(4-methoxyphenyl)prop-1-enyl]-3,5-dimethoxyphenol Chemical compound C1=CC(OC)=CC=C1C(S(=O)(=O)C(\C=C\C=1C(=CC(OC)=CC=1O)OC)C=1C=CC(OC)=CC=1)\C=C\C1=C(O)C=C(OC)C=C1OC HOPUNXURSBBUQQ-YTEMWHBBSA-N 0.000 claims description 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- GNBVPFITFYNRCN-UHFFFAOYSA-M sodium thioglycolate Chemical compound [Na+].[O-]C(=O)CS GNBVPFITFYNRCN-UHFFFAOYSA-M 0.000 description 1
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- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
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- 229940071127 thioglycolate Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
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- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
- C07C317/10—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Reproductive Health (AREA)
- Molecular Biology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Endocrinology (AREA)
- Dermatology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
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| US19784900P | 2000-04-14 | 2000-04-14 | |
| US60/197,849 | 2000-04-14 | ||
| US23470700P | 2000-09-22 | 2000-09-22 | |
| US60/234,707 | 2000-09-22 | ||
| US27164001P | 2001-02-27 | 2001-02-27 | |
| US60/271,640 | 2001-02-27 | ||
| PCT/US2001/012134 WO2001078712A1 (en) | 2000-04-14 | 2001-04-13 | Substituted styryl benzylsulfones for treating proliferative disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20030029044A KR20030029044A (ko) | 2003-04-11 |
| KR100768415B1 true KR100768415B1 (ko) | 2007-10-18 |
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| KR1020027013708A Expired - Lifetime KR100768415B1 (ko) | 2000-04-14 | 2001-04-13 | 치환된 스티릴 벤질설폰, 이의 제조방법 및 이를 포함하는 증식성 장애 치료용 약제학적 조성물 |
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| Country | Link |
|---|---|
| US (2) | US6486210B2 (enExample) |
| EP (2) | EP2359819A1 (enExample) |
| JP (1) | JP4677162B2 (enExample) |
| KR (1) | KR100768415B1 (enExample) |
| AU (2) | AU2001251615C1 (enExample) |
| CA (1) | CA2406212C (enExample) |
| DK (1) | DK1305015T3 (enExample) |
| ES (1) | ES2427088T3 (enExample) |
| IL (2) | IL152190A0 (enExample) |
| NZ (1) | NZ522551A (enExample) |
| PT (1) | PT1305015E (enExample) |
| SI (1) | SI1305015T1 (enExample) |
| WO (1) | WO2001078712A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6762207B1 (en) * | 1999-04-02 | 2004-07-13 | Temple University - Of The Commonwealth System Of Higher Education | (E)-styryl sulfone anticancer agents |
| US7053123B2 (en) | 2000-10-05 | 2006-05-30 | Temple University-Of The Commonwealth System Of Higher Education | Substituted (e)-styryl benzylsulfones for treating proliferative disorders |
| JP2004521126A (ja) * | 2001-02-27 | 2004-07-15 | 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 | (z)−スチリルベンジルスルホン及びそれらの医薬としての使用 |
| EP1370253B8 (en) | 2001-02-28 | 2008-11-26 | Temple University of the Commonwealth System of Higher Education | Use of alpha, beta unsaturated aryl sulfones for protecting cells and tissues from ionizing radiation toxicity |
| US7161031B2 (en) * | 2002-02-28 | 2007-01-09 | Temple University - Of The Commonwealth System Of Higher Education | Amino-substituted sulfonanilides and derivatives thereof for treating proliferative disorders |
| WO2003072062A2 (en) * | 2002-02-28 | 2003-09-04 | Temple University-Of The Commonwealth System Of Higher Education | Amino-substituted (e)-2,6-dialkoxystyryl 4-substituted benzylsulfones for treating proliferative disorders |
| JP4182844B2 (ja) * | 2003-09-03 | 2008-11-19 | 株式会社島津製作所 | 質量分析装置 |
| AU2004289281C1 (en) * | 2003-11-14 | 2011-12-08 | Onconova Therapeutics, Inc. | Alpha, beta-Unsaturated sulfoxides for treating proliferative disorders |
| EP3138832A1 (en) | 2004-03-16 | 2017-03-08 | Temple University - Of The Commonwealth System of Higher Education | Substituted phenoxy- and phenylthio- derivatives for treating proliferative disorders |
| US8058313B2 (en) | 2004-06-24 | 2011-11-15 | Temple University—Of the Commonwealth System of Higher Education | Alpha, beta-unsaturated sulfones, sulfoxides, sulfonimides, sulfinimides, acylsulfonamides and acylsulfinamides and therapeutic uses thereof |
| US20090306207A1 (en) * | 2005-01-05 | 2009-12-10 | Reddy M V Ramana | Treatment of Drug-Resistant Proliferative Disorders |
| SI1896401T1 (sl) * | 2005-02-25 | 2013-07-31 | Temple University - Of The Commonwealth System Of Higher Education | Sinteza nenasičenih sulfidov, sulfonov, sulfoksidov in sulfonamidov |
| WO2006104668A2 (en) * | 2005-03-11 | 2006-10-05 | Temple University - Of The Commonwealth System Of Higher Education | Composition and methods for the treatment of proliferative diseases |
| WO2008027049A1 (en) * | 2006-08-30 | 2008-03-06 | Temple University - Of The Commonwealth System Of Higher Education | Composition and methods for the treatment of myelodysplastic syndrome and acute myeloid leukemia |
| WO2008033475A2 (en) * | 2006-09-15 | 2008-03-20 | Onconova Therapeutics, Inc. | Activated cytotoxic compounds for attachment to targeting molecules for the treatment of mammalian disease conditions |
| US8735620B2 (en) * | 2008-12-17 | 2014-05-27 | Epr Pharmaceuticals Pvt. Ltd | Processes for preparing (E)-styrylbenzylsulfone compounds and uses thereof for treating proliferative disorders |
| AU2013318206B2 (en) | 2012-09-20 | 2018-07-26 | Temple University - Of The Commonwealth System Of Higher Education | Substituted alkyl diaryl derivatives, methods of preparation and uses |
| ES2864681T3 (es) | 2012-12-07 | 2021-10-14 | Onconova Therapeutics Inc | Tratamiento del cáncer hematológico refractario a un agente contra el cáncer |
| 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 |
| WO2024186641A1 (en) * | 2023-03-03 | 2024-09-12 | Onconova Therapeutics, Inc. | Methods and compositions for treating cancer |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63150237A (ja) * | 1986-11-28 | 1988-06-22 | オリオン‐ユヒチュメ・オユ | カテコール誘導体 |
| WO1999018068A1 (en) | 1997-10-03 | 1999-04-15 | Temple University - Of The Commonwealth System Of Higher Education | Styryl sulfone anticancer agents |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2532612A (en) | 1945-08-29 | 1950-12-05 | Union Oil Co | Preparation of unsaturated thio-ethers |
| US3185743A (en) | 1960-08-24 | 1965-05-25 | Union Carbide Corp | Production of olefinic compounds from allyl sulfones |
| US3418101A (en) | 1965-12-15 | 1968-12-24 | Pennsalt Chemicals Corp | Process for plant desiccation |
| US3514386A (en) | 1967-12-11 | 1970-05-26 | Exxon Research Engineering Co | Stereoselective addition of thiols to acetylenic compounds |
| US3917714A (en) | 1972-09-06 | 1975-11-04 | American Cyanamid Co | Bis(alkylsulfonyl)vinylbenzenes |
| US4161407A (en) | 1977-10-06 | 1979-07-17 | Eastman Kodak Company | Crosslinkable polymers having vinylsulfonyl groups or styrylsulfonyl groups and their use as hardeners for gelatin |
| US4386221A (en) | 1981-10-28 | 1983-05-31 | Eastman Kodak Company | Process for the preparation of aryl alkyl sulfones and aryl vinyl sulfones |
| US4937388A (en) | 1985-08-09 | 1990-06-26 | Imperial Chemical Industries Plc | Insecticidal ethers |
| FR2621038B1 (fr) * | 1987-09-28 | 1989-12-29 | Rhone Poulenc Sante | Derives d'alcadienes, leurs preparations, les medicaments les contenant et produits intermediaires |
| GB8902409D0 (en) * | 1989-02-03 | 1989-03-22 | Ici Plc | Aliphatic compounds |
| US5659087A (en) | 1995-06-07 | 1997-08-19 | Eli Lilly And Company | Diarylvinyl sulfoxides |
| JP3660395B2 (ja) * | 1995-06-22 | 2005-06-15 | 大鵬薬品工業株式会社 | フェニルスルホン誘導体及びその製造方法 |
| BR9611232A (pt) * | 1995-10-19 | 2000-03-28 | Ciba Sc Holding Ag | Antioxidantes contendo grupos fenol e grupos de anima aromática |
| US6201154B1 (en) * | 1999-03-31 | 2001-03-13 | Temple University-Of The Commonwealth Of Higher Education | Z-styryl sulfone anticancer agents |
| CA2366750C (en) * | 1999-04-02 | 2010-06-01 | Temple University - Of The Commonwealth System Of Higher Education | (e)-styryl sulfone anticancer agents |
| JP2002541101A (ja) * | 1999-04-02 | 2002-12-03 | 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 | スチリルスルホン抗癌剤 |
| WO2001026645A1 (en) * | 1999-10-12 | 2001-04-19 | Temple University-Of The Commonwealth System Of Higher Education | Method for protecting normal cells from cytotoxicity of chemotherapeutic agents |
-
2001
- 2001-04-12 US US09/833,287 patent/US6486210B2/en not_active Expired - Lifetime
- 2001-04-13 NZ NZ522551A patent/NZ522551A/en not_active IP Right Cessation
- 2001-04-13 CA CA2406212A patent/CA2406212C/en not_active Expired - Lifetime
- 2001-04-13 PT PT1925014T patent/PT1305015E/pt unknown
- 2001-04-13 EP EP10178360A patent/EP2359819A1/en not_active Withdrawn
- 2001-04-13 JP JP2001576013A patent/JP4677162B2/ja not_active Expired - Lifetime
- 2001-04-13 DK DK01925014.1T patent/DK1305015T3/da active
- 2001-04-13 EP EP01925014.1A patent/EP1305015B1/en not_active Expired - Lifetime
- 2001-04-13 ES ES01925014T patent/ES2427088T3/es not_active Expired - Lifetime
- 2001-04-13 AU AU2001251615A patent/AU2001251615C1/en not_active Expired
- 2001-04-13 AU AU5161501A patent/AU5161501A/xx active Pending
- 2001-04-13 IL IL15219001A patent/IL152190A0/xx unknown
- 2001-04-13 WO PCT/US2001/012134 patent/WO2001078712A1/en not_active Ceased
- 2001-04-13 KR KR1020027013708A patent/KR100768415B1/ko not_active Expired - Lifetime
- 2001-04-13 SI SI200131022T patent/SI1305015T1/sl unknown
-
2002
- 2002-07-29 US US10/207,429 patent/US6642410B2/en not_active Expired - Lifetime
- 2002-10-08 IL IL152190A patent/IL152190A/en active IP Right Grant
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63150237A (ja) * | 1986-11-28 | 1988-06-22 | オリオン‐ユヒチュメ・オユ | カテコール誘導体 |
| JP2735834B2 (ja) * | 1986-11-28 | 1998-04-02 | オリオン‐ユヒチュメ・オユ | カテコール誘導体 |
| WO1999018068A1 (en) | 1997-10-03 | 1999-04-15 | Temple University - Of The Commonwealth System Of Higher Education | Styryl sulfone anticancer agents |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1305015A4 (en) | 2003-05-21 |
| US20030036536A1 (en) | 2003-02-20 |
| IL152190A (en) | 2010-11-30 |
| JP4677162B2 (ja) | 2011-04-27 |
| NZ522551A (en) | 2004-03-26 |
| US6486210B2 (en) | 2002-11-26 |
| AU2001251615C1 (en) | 2006-12-07 |
| AU2001251615B2 (en) | 2005-08-11 |
| DK1305015T3 (da) | 2013-08-26 |
| ES2427088T3 (es) | 2013-10-28 |
| EP1305015A1 (en) | 2003-05-02 |
| AU5161501A (en) | 2001-10-30 |
| IL152190A0 (en) | 2003-05-29 |
| EP1305015B1 (en) | 2013-06-12 |
| JP2003530433A (ja) | 2003-10-14 |
| PT1305015E (pt) | 2013-09-06 |
| US6642410B2 (en) | 2003-11-04 |
| WO2001078712A1 (en) | 2001-10-25 |
| US20020115643A1 (en) | 2002-08-22 |
| CA2406212A1 (en) | 2001-10-25 |
| SI1305015T1 (sl) | 2013-08-30 |
| KR20030029044A (ko) | 2003-04-11 |
| EP2359819A1 (en) | 2011-08-24 |
| CA2406212C (en) | 2011-02-01 |
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