JP2008528647A5 - - Google Patents
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- Publication number
- JP2008528647A5 JP2008528647A5 JP2007553514A JP2007553514A JP2008528647A5 JP 2008528647 A5 JP2008528647 A5 JP 2008528647A5 JP 2007553514 A JP2007553514 A JP 2007553514A JP 2007553514 A JP2007553514 A JP 2007553514A JP 2008528647 A5 JP2008528647 A5 JP 2008528647A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- halogenated
- aliphatic
- group
- residue
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 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 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 210000002307 prostate Anatomy 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 201000011510 cancer Diseases 0.000 claims description 10
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 230000036210 malignancy Effects 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 150000008331 benzenesulfonamides Chemical class 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- -1 aliphatic primary amine Chemical class 0.000 claims description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 4
- 239000000051 antiandrogen Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 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 2
- 239000013543 active substance Substances 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- IPRJXAGUEGOFGG-UHFFFAOYSA-N N-butylbenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=CC=C1 IPRJXAGUEGOFGG-UHFFFAOYSA-N 0.000 claims 8
- 238000000034 method Methods 0.000 claims 6
- 239000012620 biological material Substances 0.000 claims 4
- 238000000605 extraction Methods 0.000 claims 3
- 241001553014 Myrsine salicina Species 0.000 claims 2
- 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 1
- 240000000968 Parkia biglobosa Species 0.000 claims 1
- 229960000997 bicalutamide Drugs 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 229960000978 cyproterone acetate Drugs 0.000 claims 1
- 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 1
- 239000003480 eluent Substances 0.000 claims 1
- 229960002074 flutamide Drugs 0.000 claims 1
- 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 1
- 238000005194 fractionation Methods 0.000 claims 1
- 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 1
- 238000002955 isolation Methods 0.000 claims 1
- 229960002653 nilutamide Drugs 0.000 claims 1
- 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 1
- 0 *c(cc1)c(*)cc1S(N*)(=O)=O Chemical compound *c(cc1)c(*)cc1S(N*)(=O)=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
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 true JP2008528647A5 (enExample) | 2008-09-18 |
| JP5191238B2 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
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