ES2245803T3 - Compuestos bencenicos sustituidos como agentes antiproliferativos reductores. - Google Patents
Compuestos bencenicos sustituidos como agentes antiproliferativos reductores.Info
- Publication number
- ES2245803T3 ES2245803T3 ES98939384T ES98939384T ES2245803T3 ES 2245803 T3 ES2245803 T3 ES 2245803T3 ES 98939384 T ES98939384 T ES 98939384T ES 98939384 T ES98939384 T ES 98939384T ES 2245803 T3 ES2245803 T3 ES 2245803T3
- Authority
- ES
- Spain
- Prior art keywords
- aminosulfonyl
- methoxyphenyl
- alkyl
- ocf
- benzene
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 124
- 230000001028 anti-proliverative effect Effects 0.000 title description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 150000002367 halogens Chemical group 0.000 claims abstract description 22
- 125000001424 substituent group Chemical group 0.000 claims abstract description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 8
- 230000004663 cell proliferation Effects 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 41
- 229910052801 chlorine Inorganic materials 0.000 claims description 40
- 229910052794 bromium Inorganic materials 0.000 claims description 33
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 230000002062 proliferating effect Effects 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- 230000000973 chemotherapeutic effect Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 230000002792 vascular Effects 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 239000002254 cytotoxic agent Substances 0.000 claims 1
- 231100000599 cytotoxic agent Toxicity 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract description 2
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- -1 hydrocarbon radical Chemical class 0.000 description 62
- 239000002253 acid Substances 0.000 description 39
- 125000004494 ethyl ester group Chemical group 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 238000000034 method Methods 0.000 description 24
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 22
- 238000004458 analytical method Methods 0.000 description 20
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 19
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 19
- 210000004027 cell Anatomy 0.000 description 16
- RRONENSZKCGROA-UHFFFAOYSA-N 4-fluoro-3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=CC=C1F RRONENSZKCGROA-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- IAPZMOXNDIVGNQ-UHFFFAOYSA-N 3-bromo-2,4,5,6-tetrafluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=C(F)C(F)=C(F)C(Br)=C1F IAPZMOXNDIVGNQ-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- HIPCPVSKULEHBJ-UHFFFAOYSA-N 2-bromo-3,4,5-trifluoro-n-(3-hydroxy-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(O)C(OC)=CC=C1NS(=O)(=O)C1=CC(F)=C(F)C(F)=C1Br HIPCPVSKULEHBJ-UHFFFAOYSA-N 0.000 description 7
- OQUWAOHSHWXMPX-UHFFFAOYSA-N 2-bromo-3,4,5-trifluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC(F)=C(F)C(F)=C1Br OQUWAOHSHWXMPX-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical group COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- FTIFAPZODKUUQX-UHFFFAOYSA-N 5-bromo-2,3,4-trifluoro-n-(3-hydroxy-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(O)C(OC)=CC=C1NS(=O)(=O)C1=CC(Br)=C(F)C(F)=C1F FTIFAPZODKUUQX-UHFFFAOYSA-N 0.000 description 6
- RCTCBSDWAUCMEI-UHFFFAOYSA-N 5-bromo-2,3,4-trifluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC(Br)=C(F)C(F)=C1F RCTCBSDWAUCMEI-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- BLQFHJKRTDIZLX-UHFFFAOYSA-N 5-amino-2-methoxyphenol Chemical compound COC1=CC=C(N)C=C1O BLQFHJKRTDIZLX-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical class ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 5
- XFTDZYFHXRZLEF-UHFFFAOYSA-N 2,3,4-trifluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C(F)=C1F XFTDZYFHXRZLEF-UHFFFAOYSA-N 0.000 description 4
- IAYLRIOAUQKCBY-UHFFFAOYSA-N 2-bromo-3,4,5,6-tetrafluoro-n-(3-hydroxy-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(O)C(OC)=CC=C1NS(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1Br IAYLRIOAUQKCBY-UHFFFAOYSA-N 0.000 description 4
- GGPCFSHQXLVTSO-UHFFFAOYSA-N 2-bromo-3,4,5,6-tetrafluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1Br GGPCFSHQXLVTSO-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 230000002285 radioactive effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- COVHFELBSZZSOI-UHFFFAOYSA-N 2,3,4,5-tetrafluoro-n-(3-hydroxy-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(O)C(OC)=CC=C1NS(=O)(=O)C1=CC(F)=C(F)C(F)=C1F COVHFELBSZZSOI-UHFFFAOYSA-N 0.000 description 3
- QITZCKFTLJUUKY-UHFFFAOYSA-N 2,3,4,5-tetrafluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC(F)=C(F)C(F)=C1F QITZCKFTLJUUKY-UHFFFAOYSA-N 0.000 description 3
- SLXGUUYOJAEVJS-UHFFFAOYSA-N 3,4,5-trifluoro-n-(3-hydroxy-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(O)C(OC)=CC=C1NS(=O)(=O)C1=CC(F)=C(F)C(F)=C1 SLXGUUYOJAEVJS-UHFFFAOYSA-N 0.000 description 3
- VNGDFXNFUBUXKA-UHFFFAOYSA-N 3,4,5-trifluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC(F)=C(F)C(F)=C1 VNGDFXNFUBUXKA-UHFFFAOYSA-N 0.000 description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
- PTAPWFLHAVOUHJ-UHFFFAOYSA-N 3,5-dichloro-2,4,6-trifluoro-n-(3-hydroxy-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(O)C(OC)=CC=C1NS(=O)(=O)C1=C(F)C(Cl)=C(F)C(Cl)=C1F PTAPWFLHAVOUHJ-UHFFFAOYSA-N 0.000 description 3
- JAOHKGJZZPPKCS-UHFFFAOYSA-N 3,5-dichloro-2,4,6-trifluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=C(F)C(Cl)=C(F)C(Cl)=C1F JAOHKGJZZPPKCS-UHFFFAOYSA-N 0.000 description 3
- BBBAYGJTRRZKTC-UHFFFAOYSA-N 4-bromo-2,3,5,6-tetrafluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=C(F)C(F)=C(Br)C(F)=C1F BBBAYGJTRRZKTC-UHFFFAOYSA-N 0.000 description 3
- MEZPAKLVSGAERH-UHFFFAOYSA-N 4-chloro-2,3,5,6-tetrafluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=C(F)C(F)=C(Cl)C(F)=C1F MEZPAKLVSGAERH-UHFFFAOYSA-N 0.000 description 3
- XZDWZZHAPIJEDQ-UHFFFAOYSA-N 4-fluoro-n-(3-hydroxy-4-methoxyphenyl)-3-nitrobenzenesulfonamide Chemical compound C1=C(O)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(F)C([N+]([O-])=O)=C1 XZDWZZHAPIJEDQ-UHFFFAOYSA-N 0.000 description 3
- XMRWHKXOGDGNHJ-UHFFFAOYSA-N 4-fluoro-n-(4-methoxyphenyl)-3-nitrobenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC=C(F)C([N+]([O-])=O)=C1 XMRWHKXOGDGNHJ-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229960000485 methotrexate Drugs 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
- PCGXALSKZRHXOX-UHFFFAOYSA-N 2,3,4,5-tetrafluoro-n-(3-fluoro-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1NS(=O)(=O)C1=CC(F)=C(F)C(F)=C1F PCGXALSKZRHXOX-UHFFFAOYSA-N 0.000 description 2
- WCPZRJPXQPEWOJ-UHFFFAOYSA-N 2,3,4,6-tetrafluoro-5-[(3-fluoro-4-methoxyphenyl)sulfamoyl]benzoic acid Chemical compound C1=C(F)C(OC)=CC=C1NS(=O)(=O)C1=C(F)C(F)=C(F)C(C(O)=O)=C1F WCPZRJPXQPEWOJ-UHFFFAOYSA-N 0.000 description 2
- FBAXNZWDMOJIFL-UHFFFAOYSA-N 2,3,4,6-tetrafluoro-5-[(4-methoxyphenyl)sulfamoyl]benzoic acid Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=C(F)C(F)=C(F)C(C(O)=O)=C1F FBAXNZWDMOJIFL-UHFFFAOYSA-N 0.000 description 2
- ILLJRJUJVYZWEZ-UHFFFAOYSA-N 2,3,4,6-tetrafluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=C(F)C=C(F)C(F)=C1F ILLJRJUJVYZWEZ-UHFFFAOYSA-N 0.000 description 2
- UHYIENZZAVUHSX-UHFFFAOYSA-N 2,3,4-trifluoro-5-[(4-methoxyphenyl)sulfamoyl]benzoic acid Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC(C(O)=O)=C(F)C(F)=C1F UHYIENZZAVUHSX-UHFFFAOYSA-N 0.000 description 2
- AYUOWVFSPKPEMA-UHFFFAOYSA-N 2,3,4-trifluoro-n-(3-fluoro-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(F)C(F)=C1F AYUOWVFSPKPEMA-UHFFFAOYSA-N 0.000 description 2
- ZEGWRALLTDGCBL-UHFFFAOYSA-N 2,3,4-trifluoro-n-(3-hydroxy-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(O)C(OC)=CC=C1NS(=O)(=O)C1=CC=C(F)C(F)=C1F ZEGWRALLTDGCBL-UHFFFAOYSA-N 0.000 description 2
- LBSHLAUHXYJGJZ-UHFFFAOYSA-N 2,3,4-trifluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC=C(F)C(F)=C1F LBSHLAUHXYJGJZ-UHFFFAOYSA-N 0.000 description 2
- XINCBNCLCIQIJM-UHFFFAOYSA-N 2,4,6-trifluorobenzenesulfonyl chloride Chemical compound FC1=CC(F)=C(S(Cl)(=O)=O)C(F)=C1 XINCBNCLCIQIJM-UHFFFAOYSA-N 0.000 description 2
- KZMVSDGUYVLTTH-UHFFFAOYSA-N 2-bromo-3,4,5,6-tetrafluoro-n-(3-fluoro-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1NS(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1Br KZMVSDGUYVLTTH-UHFFFAOYSA-N 0.000 description 2
- GVUZWQXNPLQRKC-UHFFFAOYSA-N 2-bromo-3,4,5,6-tetrafluorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1Br GVUZWQXNPLQRKC-UHFFFAOYSA-N 0.000 description 2
- GRBJVYGMFKVYOF-UHFFFAOYSA-N 3,4,5-trifluoro-n-(3-fluoro-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1NS(=O)(=O)C1=CC(F)=C(F)C(F)=C1 GRBJVYGMFKVYOF-UHFFFAOYSA-N 0.000 description 2
- ADUDCACBCWTINI-UHFFFAOYSA-N 3,4-difluoro-n-(3-fluoro-4-methoxyphenyl)-5-nitrobenzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1NS(=O)(=O)C1=CC(F)=C(F)C([N+]([O-])=O)=C1 ADUDCACBCWTINI-UHFFFAOYSA-N 0.000 description 2
- GLRMXHFJNKBGHG-UHFFFAOYSA-N 3,4-difluoro-n-(3-hydroxy-4-methoxyphenyl)-5-nitrobenzenesulfonamide Chemical compound C1=C(O)C(OC)=CC=C1NS(=O)(=O)C1=CC(F)=C(F)C([N+]([O-])=O)=C1 GLRMXHFJNKBGHG-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US917025 | 1997-08-22 | ||
| US08/917,025 US6284923B1 (en) | 1997-08-22 | 1997-08-22 | Substituted benzene compounds as antiproliferative and cholesterol lowering action |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2245803T3 true ES2245803T3 (es) | 2006-01-16 |
Family
ID=25438246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98939384T Expired - Lifetime ES2245803T3 (es) | 1997-08-22 | 1998-08-13 | Compuestos bencenicos sustituidos como agentes antiproliferativos reductores. |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US6284923B1 (show.php) |
| EP (1) | EP1005453B1 (show.php) |
| JP (1) | JP4309041B2 (show.php) |
| AT (1) | ATE280756T1 (show.php) |
| AU (1) | AU748826B2 (show.php) |
| CA (1) | CA2301842C (show.php) |
| DE (1) | DE69827267T2 (show.php) |
| ES (1) | ES2245803T3 (show.php) |
| PT (1) | PT1005453E (show.php) |
| WO (1) | WO1999010320A1 (show.php) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0896533B1 (en) * | 1996-02-22 | 2003-09-10 | Tularik, Inc. | Pentafluorobenzenesulfonamides and analogs |
| WO1998005315A1 (en) * | 1996-07-19 | 1998-02-12 | Tularik, Inc. | Pentafluorobenzenesulfonamides and analogs |
| US6583157B2 (en) | 1998-01-29 | 2003-06-24 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| ES2317688T3 (es) | 1998-01-29 | 2009-04-16 | Amgen Inc. | Moduladores ppar-gamma. |
| JP2002518506A (ja) * | 1998-06-25 | 2002-06-25 | テュラリク インコーポレイテッド | アリールスルホンアニリドホスフェート |
| HUP0201215A2 (en) * | 1998-12-02 | 2002-08-28 | Pfizer Prod Inc | Methods and compositions for restoring conformational stability of a protein of the p53 family |
| US7041691B1 (en) | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| DK1192137T3 (da) * | 1999-06-30 | 2013-11-11 | Amgen Inc | Forbindelser til modulering af PPAR-gamma aktivitet |
| US6306615B1 (en) | 1999-08-19 | 2001-10-23 | Tularik Inc. | Detection method for monitoring β tubulin isotype specific modification |
| WO2001082916A2 (en) | 2000-05-03 | 2001-11-08 | Tularik Inc. | Combination therapeutic compositions and methods of use |
| US20030171399A1 (en) | 2000-06-28 | 2003-09-11 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| WO2002039958A2 (en) | 2000-11-03 | 2002-05-23 | Tularik Inc. | Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents |
| US20050250854A1 (en) * | 2000-11-03 | 2005-11-10 | Amgen Inc. | Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents |
| US7547716B2 (en) * | 2001-06-08 | 2009-06-16 | Institute Of Medicinal Molecular Design, Inc. | Sulfonamide derivatives |
| JP2003081937A (ja) * | 2001-09-07 | 2003-03-19 | Bayer Ag | ベンゼンスルホンアミド誘導体 |
| US7550424B2 (en) * | 2002-11-26 | 2009-06-23 | Institute Of Virology Slovak Academy Of Sciences | CA IX-specific inhibitors |
| US7833734B2 (en) * | 2002-11-26 | 2010-11-16 | Institute Of Virology Of The Slovak Academy Of Sciences | CA IX-specific inhibitors |
| US7223761B2 (en) | 2003-10-03 | 2007-05-29 | Amgen Inc. | Salts and polymorphs of a potent antidiabetic compound |
| FI20055498A0 (fi) * | 2005-09-16 | 2005-09-16 | Biotie Therapies Corp | Sulfonamidijohdannaisia |
| GB0526252D0 (en) * | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| EP2590957B1 (en) | 2010-07-09 | 2014-11-12 | Pfizer Limited | N-sulfonylbenzamides as inhibitors of voltage-gated sodium channels |
| US8692001B2 (en) | 2010-10-27 | 2014-04-08 | Dynamix Pharmaceuticals Ltd. | Sulfonamides for the modulation of PKM2 |
| EP2925717A4 (en) * | 2012-11-28 | 2016-08-03 | Stichting Dienst Landbouwkundi | BENZOLSULFONAMIDE COMPOUNDS FOR PLANTS WITH SOMATIC EMBRYOGENESIS I |
| CN105452745B (zh) * | 2013-08-28 | 2019-03-19 | 博格华纳公司 | 高温阀轴密封 |
| GB201514021D0 (en) | 2015-08-07 | 2015-09-23 | Arner Elias Set Jeno | Novel Pyridines and their use in the treatment of cancer |
| EP3580204A1 (en) | 2017-02-07 | 2019-12-18 | Oblique Therapeutics AB | Sulfinylpyridines and their use in the treatment of cancer |
| MA47452A (fr) | 2017-02-07 | 2019-12-18 | Oblique Therapeutics Ab | Pyridines à substitution hétérocyclylsulfonyle et leur utilisation dans le traitement du cancer |
| JP7229176B2 (ja) | 2017-02-07 | 2023-02-27 | オブリーク セラピューティクス アーベー | ヒドロカルビルスルホニル置換ピリジンおよび癌の治療におけるそれらの使用 |
| AU2018218519B2 (en) | 2017-02-07 | 2021-08-05 | Oblique Therapeutics Ab | Heteroarylsulfonyl-substituted pyridines and their use in the treatment of cancer |
| US11555012B2 (en) * | 2018-11-09 | 2023-01-17 | Nimbus Artemis, Inc. | ACLY inhibitors and uses thereof |
| AU2020315192A1 (en) * | 2019-07-17 | 2022-02-24 | 2692372 Ontario, Inc. | Benzenesulfonamide derivatives and uses thereof |
| JP2025510669A (ja) * | 2022-03-21 | 2025-04-15 | ケモセントリックス，インコーポレイティド | Ｃｘｃｒ６スルホンアミド化合物 |
| WO2024175999A2 (en) * | 2023-02-23 | 2024-08-29 | Dunad Therapeutics Ltd. | Benzenesulfonamide derivatives and uses thereof |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1955207A (en) | 1931-09-16 | 1934-04-17 | Ig Farbenindustrie Ag | Mothproofing agent |
| DE622494C (de) | 1932-01-03 | 1935-11-29 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von Mono- bzw. Polynitropolysulfonen und deren Reduktionsprodukten |
| US2358365A (en) | 1940-08-03 | 1944-09-19 | Parke Davis & Co | Sulphonamide derivatives and process for obtaining the same |
| US2450863A (en) | 1946-03-07 | 1948-10-05 | Socony Vacuum Oil Co Inc | Amides from sulfonyl fluorides |
| CH362688A (de) | 1957-09-10 | 1962-06-30 | Geigy Ag J R | Verfahren zur Herstellung von neuen Arylsulfonarylamiden |
| US2937202A (en) | 1958-05-19 | 1960-05-17 | Dow Chemical Co | Substituted benzenesulfonanilides |
| GB938890A (en) | 1961-02-03 | 1963-10-09 | Boots Pure Drug Co Ltd | New fungicidal compositions and compounds |
| NL301745A (show.php) | 1962-12-17 | |||
| CH504416A (de) * | 1966-12-05 | 1971-03-15 | Ciba Geigy Ag | Verfahren zur Herstellung von aromatischen Sulfamoylverbindungen |
| US3505455A (en) | 1966-12-15 | 1970-04-07 | Ansul Co | Nematocidal method |
| NL174644C (nl) | 1970-04-13 | 1984-07-16 | Minnesota Mining & Mfg | Werkwijze ter bereiding van een herbicide verbinding; tevens werkwijze voor de bereiding van een preparaat met herbicide werking. |
| US3951910A (en) * | 1973-12-28 | 1976-04-20 | General Electric Company | Flame retardant polycarbonate composition |
| US4013621A (en) | 1975-04-29 | 1977-03-22 | Ciba-Geigy Corporation | Substituted sulfonamide derivatives of hindered phenols and stabilized compositions |
| DE2528697C2 (de) | 1975-06-27 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Salicylaldehyden |
| US4034110A (en) | 1976-09-20 | 1977-07-05 | Hoffmann-La Roche Inc. | Anthelmintics effective against liver flukes |
| US4239699A (en) | 1978-05-24 | 1980-12-16 | Henkel Corporation | Sulfonamidophenols, metal complexes thereof, and solutions containing such compounds for use in extraction of metal values |
| US4373017A (en) | 1980-03-05 | 1983-02-08 | Konishiroku Photo Industry Co., Ltd. | Photosensitive compound and photosensitive material containing it |
| US4483986A (en) | 1982-05-03 | 1984-11-20 | Eli Lilly And Company | 4-Nitrobenzophenone compounds |
| NZ215272A (en) | 1985-02-27 | 1989-08-29 | Mitsui Toatsu Chemicals | Fungicidal n-(2-chloro-4-nitrophenyl)-benzenesulphonamide derivatives and compositions thereof |
| US4692466A (en) | 1985-02-28 | 1987-09-08 | Mitsui Toatsu Chemicals, Incorporated | N-(2-chloro-4-trifluoromethylphenyl)-3-trifluoromethylbenzenesulfonamide derivative and agricultural fungicide containing same |
| US5280043A (en) | 1988-10-10 | 1994-01-18 | Smith Kline & French Laboratories Ltd. | Sulphonamido containing phenylalkanoic acids as thromboxane A2 antagonists |
| DE3905075A1 (de) | 1989-02-18 | 1990-08-30 | Hoechst Ag | Benzolsulfonamide und verfahren zu ihrer herstellung |
| ATE167473T1 (de) | 1990-08-20 | 1998-07-15 | Eisai Co Ltd | Sulfonamid-derivate |
| WO1996040629A1 (en) * | 1995-06-07 | 1996-12-19 | Sugen, Inc. | Tyrphostin-like compounds for the treatment of cell proliferative disorders or cell differentiation disorders |
-
1997
- 1997-08-22 US US08/917,025 patent/US6284923B1/en not_active Expired - Fee Related
-
1998
- 1998-08-13 AU AU87824/98A patent/AU748826B2/en not_active Ceased
- 1998-08-13 ES ES98939384T patent/ES2245803T3/es not_active Expired - Lifetime
- 1998-08-13 EP EP98939384A patent/EP1005453B1/en not_active Expired - Lifetime
- 1998-08-13 JP JP2000507650A patent/JP4309041B2/ja not_active Expired - Fee Related
- 1998-08-13 PT PT98939384T patent/PT1005453E/pt unknown
- 1998-08-13 DE DE69827267T patent/DE69827267T2/de not_active Expired - Lifetime
- 1998-08-13 AT AT98939384T patent/ATE280756T1/de not_active IP Right Cessation
- 1998-08-13 WO PCT/US1998/016781 patent/WO1999010320A1/en not_active Ceased
- 1998-08-13 CA CA2301842A patent/CA2301842C/en not_active Expired - Fee Related
-
2001
- 2001-05-31 US US09/872,463 patent/US6388131B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PT1005453E (pt) | 2005-02-28 |
| WO1999010320A8 (en) | 1999-09-23 |
| JP4309041B2 (ja) | 2009-08-05 |
| ATE280756T1 (de) | 2004-11-15 |
| DE69827267D1 (de) | 2004-12-02 |
| AU748826B2 (en) | 2002-06-13 |
| CA2301842A1 (en) | 1999-03-04 |
| EP1005453A1 (en) | 2000-06-07 |
| US6388131B2 (en) | 2002-05-14 |
| WO1999010320A1 (en) | 1999-03-04 |
| JP2001514167A (ja) | 2001-09-11 |
| AU8782498A (en) | 1999-03-16 |
| EP1005453B1 (en) | 2004-10-27 |
| US20020013496A1 (en) | 2002-01-31 |
| CA2301842C (en) | 2010-04-27 |
| DE69827267T2 (de) | 2006-02-02 |
| US6284923B1 (en) | 2001-09-04 |
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