JP5191238B2 - Ｎ−ブチルベンゼンスルホンアミドの単離、ベンゼンスルホンアミド誘導体の合成ならびにｎ−ブチルベンゼンスルホンアミドおよびベンゼンスルホンアミド誘導体の良性前立腺過形成および／または前立腺悪性腫瘍の処置のための使用 - Google Patents
Ｎ−ブチルベンゼンスルホンアミドの単離、ベンゼンスルホンアミド誘導体の合成ならびにｎ−ブチルベンゼンスルホンアミドおよびベンゼンスルホンアミド誘導体の良性前立腺過形成および／または前立腺悪性腫瘍の処置のための使用 Download PDFInfo
- Publication number
- JP5191238B2 JP5191238B2 JP2007553514A JP2007553514A JP5191238B2 JP 5191238 B2 JP5191238 B2 JP 5191238B2 JP 2007553514 A JP2007553514 A JP 2007553514A JP 2007553514 A JP2007553514 A JP 2007553514A JP 5191238 B2 JP5191238 B2 JP 5191238B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- group
- benzenesulfonamide
- butylbenzenesulfonamide
- extract
- 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 - Fee Related
Links
- IPRJXAGUEGOFGG-UHFFFAOYSA-N N-butylbenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=CC=C1 IPRJXAGUEGOFGG-UHFFFAOYSA-N 0.000 title claims description 109
- 238000011282 treatment Methods 0.000 title claims description 37
- 210000002307 prostate Anatomy 0.000 title claims description 36
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 title claims description 26
- 208000004403 Prostatic Hyperplasia Diseases 0.000 title claims description 26
- 201000011510 cancer Diseases 0.000 title claims description 25
- 206010028980 Neoplasm Diseases 0.000 title claims description 21
- 230000036210 malignancy Effects 0.000 title claims description 19
- 150000008331 benzenesulfonamides Chemical class 0.000 title claims description 17
- 238000002955 isolation Methods 0.000 title claims description 5
- 230000015572 biosynthetic process Effects 0.000 title description 34
- 238000003786 synthesis reaction Methods 0.000 title description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 93
- 230000002280 anti-androgenic effect Effects 0.000 claims description 49
- 239000000284 extract Substances 0.000 claims description 34
- 239000000051 antiandrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 230000000694 effects Effects 0.000 claims description 17
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- 238000012360 testing method Methods 0.000 claims description 15
- 239000013543 active substance Substances 0.000 claims description 14
- 102000001307 androgen receptors Human genes 0.000 claims description 14
- 108010080146 androgen receptors Proteins 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- 239000003098 androgen Substances 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 206010060862 Prostate cancer Diseases 0.000 claims description 10
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- YPQLFJODEKMJEF-UHFFFAOYSA-N hydroxyflutamide Chemical compound CC(C)(O)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 YPQLFJODEKMJEF-UHFFFAOYSA-N 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- -1 aliphatic primary amine Chemical class 0.000 claims description 7
- 239000012620 biological material Substances 0.000 claims description 7
- AFMZGMJNKXOLEM-JXMROGBWSA-N (2e)-3,7-dimethylocta-2,6-dien-1-amine Chemical compound CC(C)=CCC\C(C)=C\CN AFMZGMJNKXOLEM-JXMROGBWSA-N 0.000 claims description 6
- 238000005194 fractionation Methods 0.000 claims description 6
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims description 5
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 5
- 229940088597 hormone Drugs 0.000 claims description 5
- 239000005556 hormone Substances 0.000 claims description 5
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims description 5
- 229950005143 sitosterol Drugs 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 108700008625 Reporter Genes Proteins 0.000 claims description 4
- 229940076810 beta sitosterol Drugs 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 229960000978 cyproterone acetate Drugs 0.000 claims description 4
- UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 claims description 4
- 239000000469 ethanolic extract Substances 0.000 claims description 4
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims description 3
- 229960000997 bicalutamide Drugs 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims description 3
- 229960002074 flutamide Drugs 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- NBWCUNOBPFBKJE-UKTHLTGXSA-N n-[(2e)-3,7-dimethylocta-2,6-dienyl]-4-nitro-3-(trifluoromethyl)benzenesulfonamide Chemical compound CC(C)=CCC\C(C)=C\CNS(=O)(=O)C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 NBWCUNOBPFBKJE-UKTHLTGXSA-N 0.000 claims description 3
- OBKZIFMEYWPBGE-NTCAYCPXSA-N n-[(2e)-3,7-dimethylocta-2,6-dienyl]benzenesulfonamide Chemical compound CC(C)=CCC\C(C)=C\CNS(=O)(=O)C1=CC=CC=C1 OBKZIFMEYWPBGE-NTCAYCPXSA-N 0.000 claims description 3
- PDPZYXBDZPXLPZ-UHFFFAOYSA-N n-butyl-3-(trifluoromethyl)benzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 PDPZYXBDZPXLPZ-UHFFFAOYSA-N 0.000 claims description 3
- ALSZROWBLQSOGL-UHFFFAOYSA-N n-butyl-4-nitro-3-(trifluoromethyl)benzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 ALSZROWBLQSOGL-UHFFFAOYSA-N 0.000 claims description 3
- XIDOZGRWMHOSFW-UHFFFAOYSA-N n-pentylbenzenesulfonamide Chemical compound CCCCCNS(=O)(=O)C1=CC=CC=C1 XIDOZGRWMHOSFW-UHFFFAOYSA-N 0.000 claims description 3
- XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 claims description 3
- 229960002653 nilutamide Drugs 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims description 2
- 230000010261 cell growth Effects 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- JDFQESJSEKBBIL-UHFFFAOYSA-N n-dodecylbenzenesulfonamide Chemical compound CCCCCCCCCCCCNS(=O)(=O)C1=CC=CC=C1 JDFQESJSEKBBIL-UHFFFAOYSA-N 0.000 claims description 2
- WNSXUAGCWVZDQC-UHFFFAOYSA-N n-ethylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=CC=C1 WNSXUAGCWVZDQC-UHFFFAOYSA-N 0.000 claims description 2
- SVDVKEBISAOWJT-UHFFFAOYSA-N n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1 SVDVKEBISAOWJT-UHFFFAOYSA-N 0.000 claims description 2
- OKPTYPHVKNNPSG-UHFFFAOYSA-N n-propylbenzenesulfonamide Chemical compound CCCNS(=O)(=O)C1=CC=CC=C1 OKPTYPHVKNNPSG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 240000000968 Parkia biglobosa Species 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000012258 culturing Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- VGTQGSDABZKXKF-GXDHUFHOSA-N n-[(2e)-3,7-dimethylocta-2,6-dienyl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound CC(C)=CCC\C(C)=C\CNS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 VGTQGSDABZKXKF-GXDHUFHOSA-N 0.000 claims 1
- MTNVHLMOGSREBQ-UHFFFAOYSA-N n-butyl-1-phenylmethanesulfonamide Chemical compound CCCCNS(=O)(=O)CC1=CC=CC=C1 MTNVHLMOGSREBQ-UHFFFAOYSA-N 0.000 claims 1
- RGFXUQFSTLVNLJ-UHFFFAOYSA-N n-butyl-4-fluorobenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=C(F)C=C1 RGFXUQFSTLVNLJ-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 210000004027 cell Anatomy 0.000 description 21
- 241000200478 Prunus africana Species 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229940124530 sulfonamide Drugs 0.000 description 8
- 150000003456 sulfonamides Chemical class 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 108060001084 Luciferase Proteins 0.000 description 6
- 239000005089 Luciferase Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 101000928259 Homo sapiens NADPH:adrenodoxin oxidoreductase, mitochondrial Proteins 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 5
- 102000046818 human AR Human genes 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- CCCIJQPRIXGQOE-XWSJACJDSA-N 17beta-hydroxy-17-methylestra-4,9,11-trien-3-one Chemical compound C1CC2=CC(=O)CCC2=C2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)C=C2 CCCIJQPRIXGQOE-XWSJACJDSA-N 0.000 description 4
- BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 101000775732 Homo sapiens Androgen receptor Proteins 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000002026 chloroform extract Substances 0.000 description 4
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 238000002953 preparative HPLC Methods 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- 206010020880 Hypertrophy Diseases 0.000 description 3
- 235000000719 Prunus africana Nutrition 0.000 description 3
- 229940030486 androgens Drugs 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000004663 cell proliferation Effects 0.000 description 3
- 238000011461 current therapy Methods 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 description 2
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- ONCAZCNPWWQQMW-UHFFFAOYSA-N 3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC(S(Cl)(=O)=O)=C1 ONCAZCNPWWQQMW-UHFFFAOYSA-N 0.000 description 2
- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 description 2
- LJQUNSRHHHYXEW-UHFFFAOYSA-N 4-nitro-3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1C(F)(F)F LJQUNSRHHHYXEW-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- SJZIEWHCBXFXEL-JXMROGBWSA-N CC(C)=CCC/C(\C)=C/CNS(=O)=O Chemical compound CC(C)=CCC/C(\C)=C/CNS(=O)=O SJZIEWHCBXFXEL-JXMROGBWSA-N 0.000 description 2
- 240000001980 Cucurbita pepo Species 0.000 description 2
- 241000701022 Cytomegalovirus Species 0.000 description 2
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 description 2
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 description 2
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000012980 RPMI-1640 medium Substances 0.000 description 2
- 240000006661 Serenoa repens Species 0.000 description 2
- 235000005318 Serenoa repens Nutrition 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- 239000008931 Tadenan Substances 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 102000005936 beta-Galactosidase Human genes 0.000 description 2
- 108010005774 beta-Galactosidase Proteins 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 210000004748 cultured cell Anatomy 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 2
- 229940114124 ferulic acid Drugs 0.000 description 2
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 2
- 235000001785 ferulic acid Nutrition 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 239000002035 hexane extract Substances 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 230000003211 malignant effect Effects 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000000401 methanolic extract Substances 0.000 description 2
- 229940100243 oleanolic acid Drugs 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 229940014903 tadenan Drugs 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 2
- 238000001890 transfection Methods 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 229940096998 ursolic acid Drugs 0.000 description 2
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 description 2
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 description 1
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- VUMLNGRYFJXOMK-UHFFFAOYSA-N 1-phenylpentane-1-sulfonamide Chemical compound CCCCC(S(N)(=O)=O)C1=CC=CC=C1 VUMLNGRYFJXOMK-UHFFFAOYSA-N 0.000 description 1
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 1
- BQNBPKRLDKHPIN-UHFFFAOYSA-N 2-(2-hydroxyethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1CCO BQNBPKRLDKHPIN-UHFFFAOYSA-N 0.000 description 1
- OMSYQBMPVKCLFB-UHFFFAOYSA-N 2-butyl-3-(trifluoromethyl)benzenesulfonamide Chemical compound CCCCC1=C(C(F)(F)F)C=CC=C1S(N)(=O)=O OMSYQBMPVKCLFB-UHFFFAOYSA-N 0.000 description 1
- ZPEITFHYQFMRLT-UHFFFAOYSA-N 2-butyl-4-nitro-3-(trifluoromethyl)benzenesulfonamide Chemical compound CCCCC1=C(S(N)(=O)=O)C=CC([N+]([O-])=O)=C1C(F)(F)F ZPEITFHYQFMRLT-UHFFFAOYSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- GRUAMSTZJXJEIF-UHFFFAOYSA-N 2-dodecylbenzenesulfonamide Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(N)(=O)=O GRUAMSTZJXJEIF-UHFFFAOYSA-N 0.000 description 1
- NMBWXBWFDHVLGS-UHFFFAOYSA-N 2-ethylbenzenesulfonamide Chemical compound CCC1=CC=CC=C1S(N)(=O)=O NMBWXBWFDHVLGS-UHFFFAOYSA-N 0.000 description 1
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- BEXJGSYJZVGRLZ-UHFFFAOYSA-N 2-pentylbenzenesulfonamide Chemical compound CCCCCC1=CC=CC=C1S(N)(=O)=O BEXJGSYJZVGRLZ-UHFFFAOYSA-N 0.000 description 1
- QZZZWEIWYVXIHQ-UHFFFAOYSA-N 2-propylbenzenesulfonamide Chemical compound CCCC1=CC=CC=C1S(N)(=O)=O QZZZWEIWYVXIHQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 description 1
- ZUTVRDMZQSHCID-UHFFFAOYSA-N 3-(trifluoromethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 ZUTVRDMZQSHCID-UHFFFAOYSA-N 0.000 description 1
- QOOWQTXTTMPMSX-UHFFFAOYSA-N 4-fluoro-2-(2-hydroxyethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(F)C=C1CCO QOOWQTXTTMPMSX-UHFFFAOYSA-N 0.000 description 1
- LMMQROYAOUDXDD-UHFFFAOYSA-N 4-fluoro-n-(2-hydroxyethyl)benzenesulfonamide Chemical compound OCCNS(=O)(=O)C1=CC=C(F)C=C1 LMMQROYAOUDXDD-UHFFFAOYSA-N 0.000 description 1
- JZDSLOPGYDEFOJ-UHFFFAOYSA-N 4-nitro-3-(trifluoromethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 JZDSLOPGYDEFOJ-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 201000003126 Anuria Diseases 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 206010069632 Bladder dysfunction Diseases 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- IGXWBGJHJZYPQS-SSDOTTSWSA-N D-Luciferin Chemical compound OC(=O)[C@H]1CSC(C=2SC3=CC=C(O)C=C3N=2)=N1 IGXWBGJHJZYPQS-SSDOTTSWSA-N 0.000 description 1
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 description 1
- CYCGRDQQIOGCKX-UHFFFAOYSA-N Dehydro-luciferin Natural products OC(=O)C1=CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 CYCGRDQQIOGCKX-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- BJGNCJDXODQBOB-UHFFFAOYSA-N Fivefly Luciferin Natural products OC(=O)C1CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 BJGNCJDXODQBOB-UHFFFAOYSA-N 0.000 description 1
- 102000002464 Galactosidases Human genes 0.000 description 1
- 108010093031 Galactosidases Proteins 0.000 description 1
- 101000836540 Homo sapiens Aldo-keto reductase family 1 member B1 Proteins 0.000 description 1
- 101000809450 Homo sapiens Amphiregulin Proteins 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- DDWFXDSYGUXRAY-UHFFFAOYSA-N Luciferin Natural products CCc1c(C)c(CC2NC(=O)C(=C2C=C)C)[nH]c1Cc3[nH]c4C(=C5/NC(CC(=O)O)C(C)C5CC(=O)O)CC(=O)c4c3C DDWFXDSYGUXRAY-UHFFFAOYSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 208000025844 Prostatic disease Diseases 0.000 description 1
- 206010051482 Prostatomegaly Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 206010065584 Urethral stenosis Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000009702 cancer cell proliferation Effects 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000006143 cell culture medium Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000001516 cell proliferation assay Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 206010013990 dysuria Diseases 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000013604 expression vector Substances 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 239000003673 groundwater Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000001794 hormone therapy Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 210000003292 kidney cell Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 238000003670 luciferase enzyme activity assay Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000020033 male sex differentiation Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- QHUJTQAJBPYVQF-UHFFFAOYSA-N n-(2-hydroxyethyl)benzenesulfonamide Chemical compound OCCNS(=O)(=O)C1=CC=CC=C1 QHUJTQAJBPYVQF-UHFFFAOYSA-N 0.000 description 1
- RQUXYBHREKXNKT-UHFFFAOYSA-N n-butyl-4-methylbenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=C(C)C=C1 RQUXYBHREKXNKT-UHFFFAOYSA-N 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940068065 phytosterols Drugs 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 210000005267 prostate cell Anatomy 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000013102 re-test Methods 0.000 description 1
- 230000030541 receptor transactivation Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000010018 saw palmetto extract Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000015500 sitosterol Nutrition 0.000 description 1
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003505 terpenes Chemical group 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 201000001988 urethral stricture Diseases 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
- A61K36/736—Prunus, e.g. plum, cherry, peach, apricot or almond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Botany (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Urology & Nephrology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Tropical Medicine & Parasitology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005005397.1 | 2005-02-05 | ||
| DE102005005397A DE102005005397B4 (de) | 2005-02-05 | 2005-02-05 | Isolierung von N-Butylbenzolsulfonamid, Synthese von Benzolsulfonamid-Derivaten sowie Verwendung von N-Butylbenzolsulfonamid und Benzolsulfonamid-Derivaten zur Behandlung der benignen Prostatahyperplasie und/oder des Prostatakarzinoms |
| PCT/EP2006/000746 WO2006081994A2 (de) | 2005-02-05 | 2006-01-28 | Isolierung von n-butylbenzolsulfonamid, synthese von benzolsulfonamid-derivaten sowie verwendung von n-butylbenzolsulfonamid und benzolsulfonamid-derivaten zur behandlung der benignen prostatahyperplasie und/oder des prostatakarzinoms |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008528647A JP2008528647A (ja) | 2008-07-31 |
| JP2008528647A5 JP2008528647A5 (enExample) | 2008-09-18 |
| JP5191238B2 true JP5191238B2 (ja) | 2013-05-08 |
Family
ID=36129940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007553514A Expired - Fee Related JP5191238B2 (ja) | 2005-02-05 | 2006-01-28 | Ｎ−ブチルベンゼンスルホンアミドの単離、ベンゼンスルホンアミド誘導体の合成ならびにｎ−ブチルベンゼンスルホンアミドおよびベンゼンスルホンアミド誘導体の良性前立腺過形成および／または前立腺悪性腫瘍の処置のための使用 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7700654B2 (enExample) |
| EP (1) | EP1845963A2 (enExample) |
| JP (1) | JP5191238B2 (enExample) |
| KR (1) | KR20070100844A (enExample) |
| CN (1) | CN101111240B (enExample) |
| AU (1) | AU2006210040B9 (enExample) |
| BR (1) | BRPI0606563A2 (enExample) |
| CA (1) | CA2596618C (enExample) |
| DE (1) | DE102005005397B4 (enExample) |
| MX (1) | MX2007009402A (enExample) |
| WO (1) | WO2006081994A2 (enExample) |
| ZA (1) | ZA200706061B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2734215B1 (en) * | 2011-07-22 | 2019-06-05 | Goel, Pawan Kumar | Improved process for pygeum extraction |
| US20130085283A1 (en) * | 2011-10-04 | 2013-04-04 | Coyote Pharmaceuticals, Inc. | Geranylgeranylacetone derivatives |
| WO2013157926A1 (en) * | 2012-04-19 | 2013-10-24 | Nyken Holding B.V. | Geranyl geranyl acetone analogs and uses thereof |
| CN104892470B (zh) * | 2015-06-11 | 2017-04-12 | 嘉兴学院 | 制备n‑烷基对甲苯磺酰胺的方法 |
| US9782370B2 (en) * | 2015-12-21 | 2017-10-10 | Gongwin Biopharm Holdings Co., Ltd. | Pharmaceutical compositions of benzenesulfonamide derivatives for treatment of adenoid cystic carcinoma |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3518075A (en) * | 1963-01-28 | 1970-06-30 | Stauffer Chemical Co | Method of controlling weeds |
| JPS5829784B2 (ja) * | 1975-08-22 | 1983-06-24 | 萬有製薬株式会社 | オメガ − （ アリ−ルスルホンアミド ）− アルキルアミンノ セイホウ |
| DE2948186A1 (de) * | 1979-11-30 | 1981-07-23 | Henkel KGaA, 4000 Düsseldorf | Neue sulfonamide, ihre herstellung und ihre verwendung als antimikrobielle substanzen |
| CA1241967A (en) * | 1984-05-11 | 1988-09-13 | George C. Buzby Jr. | Sulfonamides useful as anti-arrhythmic agents |
| HU208113B (en) * | 1987-08-20 | 1993-08-30 | Smith Kline French Lab | Process for producing sulfonamide derivatives and pharmaceutical compositions comprising same as active ingredient |
| US5962490A (en) * | 1987-09-25 | 1999-10-05 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
| JPH02266351A (ja) * | 1989-04-06 | 1990-10-31 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料の処理方法 |
| ES2125468T3 (es) * | 1993-08-16 | 1999-03-01 | Meiji Seika Kaisha | Derivado de sulfonilsemicarbazida y composicion para mantener la frescura de las flores cortadas. |
| ATE169298T1 (de) * | 1994-03-28 | 1998-08-15 | Pfizer | Benzisothiazol-derivate als inhibitoren der 5- lipoxygenase biosynthese |
| US5891454A (en) * | 1997-03-28 | 1999-04-06 | Alexander Wu | Anti-cancer drug and special tumor necrotizing agent |
| FR2764890B1 (fr) * | 1997-06-24 | 1999-08-27 | Adir | Nouveaux derives chromeniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6121252A (en) * | 1998-03-30 | 2000-09-19 | Guilford Pharmaceuticals Inc. | Phosphinic acid derivatives |
| JP2000338660A (ja) * | 1999-05-27 | 2000-12-08 | Toray Ind Inc | ポジ型電子線レジスト組成物およびこれを用いたレジストパターンの製造法 |
| CA2318004A1 (en) * | 1999-09-15 | 2001-03-15 | Oridigm Corporation | Novel polyamine analogues as therapeutic and diagnostic agents |
| CA2422767A1 (en) * | 1999-10-22 | 2001-04-22 | Glaxo Group Limited | In vivo imaging |
| US6727287B2 (en) * | 2001-04-16 | 2004-04-27 | Pts International, Inc. | Toluene sulfonamide-containing anti-tumor composition and method of use thereof |
| US7332525B2 (en) * | 2003-01-17 | 2008-02-19 | Castle Erik P | Method of treatment of prostate cancer and composition for treatment thereof |
| ATE291413T1 (de) * | 2003-07-17 | 2005-04-15 | 3M Espe Ag | Dentalzusammensetzungen mit ethyleniminverbindungen und nicht-reaktiven beschleunigern |
| US7576206B2 (en) * | 2003-08-14 | 2009-08-18 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
| US7223745B2 (en) * | 2003-08-14 | 2007-05-29 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
| TW200600091A (en) * | 2004-05-21 | 2006-01-01 | Telik Inc | Sulfonylethyl phosphorodiamidates |
| AR050552A1 (es) * | 2004-09-02 | 2006-11-01 | Osi Pharm Inc | Mercaptoamidas como inhibidores de histona desacetilasa |
-
2005
- 2005-02-05 DE DE102005005397A patent/DE102005005397B4/de not_active Expired - Fee Related
-
2006
- 2006-01-28 EP EP06706462A patent/EP1845963A2/de not_active Withdrawn
- 2006-01-28 WO PCT/EP2006/000746 patent/WO2006081994A2/de not_active Ceased
- 2006-01-28 MX MX2007009402A patent/MX2007009402A/es active IP Right Grant
- 2006-01-28 US US11/883,415 patent/US7700654B2/en not_active Expired - Fee Related
- 2006-01-28 KR KR1020077020245A patent/KR20070100844A/ko not_active Abandoned
- 2006-01-28 BR BRPI0606563-5A patent/BRPI0606563A2/pt not_active IP Right Cessation
- 2006-01-28 JP JP2007553514A patent/JP5191238B2/ja not_active Expired - Fee Related
- 2006-01-28 CA CA2596618A patent/CA2596618C/en not_active Expired - Fee Related
- 2006-01-28 CN CN2006800037419A patent/CN101111240B/zh not_active Expired - Fee Related
- 2006-01-28 AU AU2006210040A patent/AU2006210040B9/en not_active Ceased
-
2007
- 2007-07-17 ZA ZA200706061A patent/ZA200706061B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006081994A2 (de) | 2006-08-10 |
| WO2006081994A3 (de) | 2007-03-22 |
| JP2008528647A (ja) | 2008-07-31 |
| AU2006210040B2 (en) | 2011-04-14 |
| MX2007009402A (es) | 2007-09-25 |
| ZA200706061B (en) | 2008-07-30 |
| US7700654B2 (en) | 2010-04-20 |
| CN101111240B (zh) | 2011-09-21 |
| DE102005005397B4 (de) | 2008-08-21 |
| BRPI0606563A2 (pt) | 2009-11-17 |
| CA2596618A1 (en) | 2006-08-10 |
| DE102005005397A1 (de) | 2006-08-10 |
| US20080177107A1 (en) | 2008-07-24 |
| CN101111240A (zh) | 2008-01-23 |
| CA2596618C (en) | 2013-05-07 |
| AU2006210040A1 (en) | 2006-08-10 |
| AU2006210040B9 (en) | 2011-05-26 |
| EP1845963A2 (de) | 2007-10-24 |
| KR20070100844A (ko) | 2007-10-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013063986A (ja) | アトラル酸の単離、アトラル酸誘導体の合成、ならびにアトラル酸およびその誘導体の、良性前立腺過形成、前立腺悪性腫瘍および球脊髄性筋萎縮症の処置のための使用 | |
| FR2476093A1 (fr) | Nouveaux composes 3-hydroxy ou 3-acyloxy 1,3,5(10)-estratriene-17b-oxycarbonylmethyle et leur application en therapeutique | |
| JP5191238B2 (ja) | Ｎ−ブチルベンゼンスルホンアミドの単離、ベンゼンスルホンアミド誘導体の合成ならびにｎ−ブチルベンゼンスルホンアミドおよびベンゼンスルホンアミド誘導体の良性前立腺過形成および／または前立腺悪性腫瘍の処置のための使用 | |
| US8685469B2 (en) | In vitro anti-sickling activity of betulinic acid, oleanolic acid and their derivatives | |
| US11173142B2 (en) | Cancer treatment composition | |
| CN102697821B (zh) | 荒漠寄生植物锁阳的综合利用方法及其产物和它们的应用 | |
| Nyasse et al. | Trypanocidal activity of bergenin, the major constituent of Flueggea virosa, on Trypanosoma brucei | |
| US9061023B2 (en) | Management and treatment of benign prostatic hyperplasia | |
| Satpathy et al. | Amelioration of postmenopausal osteoporosis and anticancer properties of an antioxidant enriched fraction from Hygrophila spinosa T. Anders | |
| JPS63284125A (ja) | テストステロン５α−リダクタ−ゼ阻害剤 | |
| Mangathayaru et al. | Estrogenic effect of Erythrina variegata L. in prepubertal female rats | |
| Jiang et al. | Mai Guan Fu Kang tablet (MGFK) Accelerates Diabetic Foot Ulcer Healing via Antioxidant Defense and inflammation Suppression | |
| EP1945238A2 (de) | Extrakte aus der rinde von corynanthe-arten und deren verwendung sowie diese extrakte enthaltende arzneimittel, diätetische lebensmittel und pharmazeutische zubereitungen | |
| CN115300498A (zh) | 阿格拉宾在制备治疗或预防糖尿病肾病药物中的应用及其提取方法 | |
| Devaraji et al. | GC-MS Profiling, Anticancer Activity of Moringa oleifera Lam. Hydroalcoholic Fruit Extract Against Colorectal Cancer Cells, and In Silico Targeting of BRAF in the Serrated Pathway | |
| Singh et al. | EVALUATION OF ANTI-INFLAMATORY AND ANALGESIC ACTIVITY OF ETHANOLIC EXTRACT OF PRAECITRULLUS FISTULOSUS IN MICE | |
| CN106727564A (zh) | Atropurpuran的哌嗪基和二羟乙胺基衍生物组合物用于防治肾纤维化 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A072 | Dismissal of procedure [no reply to invitation to correct request for examination] |
Free format text: JAPANESE INTERMEDIATE CODE: A072 Effective date: 20080603 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080801 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080801 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110920 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20111220 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20111228 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120120 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120127 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120220 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120227 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120321 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120508 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120808 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120911 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20121210 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130115 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130129 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20160208 Year of fee payment: 3 |
|
| LAPS | Cancellation because of no payment of annual fees |