MX2007009402A - Separacion de n-butilbencenosulfonamida, sintesis de derivados de bencenosulfonamida y utilizacion de n-butilbencenosulfonamida y derivados de bencenosulfonamida en el tratamiento de hiperplasias prostaticas benignas y/o carcinoma de prostata. - Google Patents
Separacion de n-butilbencenosulfonamida, sintesis de derivados de bencenosulfonamida y utilizacion de n-butilbencenosulfonamida y derivados de bencenosulfonamida en el tratamiento de hiperplasias prostaticas benignas y/o carcinoma de prostata.Info
- Publication number
- MX2007009402A MX2007009402A MX2007009402A MX2007009402A MX2007009402A MX 2007009402 A MX2007009402 A MX 2007009402A MX 2007009402 A MX2007009402 A MX 2007009402A MX 2007009402 A MX2007009402 A MX 2007009402A MX 2007009402 A MX2007009402 A MX 2007009402A
- Authority
- MX
- Mexico
- Prior art keywords
- hydrogen
- prostate
- formula
- radical
- benzenesulfonamide
- Prior art date
Links
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (1)
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| MX2007009402A true MX2007009402A (es) | 2007-09-25 |
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| MX2007009402A MX2007009402A (es) | 2005-02-05 | 2006-01-28 | Separacion de n-butilbencenosulfonamida, sintesis de derivados de bencenosulfonamida y utilizacion de n-butilbencenosulfonamida y derivados de bencenosulfonamida en el tratamiento de hiperplasias prostaticas benignas y/o carcinoma de prostata. |
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| JP (1) | JP5191238B2 (enExample) |
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| MX (1) | MX2007009402A (enExample) |
| WO (1) | WO2006081994A2 (enExample) |
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| 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 |
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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
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- 2007-07-17 ZA ZA200706061A patent/ZA200706061B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006081994A2 (de) | 2006-08-10 |
| JP5191238B2 (ja) | 2013-05-08 |
| WO2006081994A3 (de) | 2007-03-22 |
| JP2008528647A (ja) | 2008-07-31 |
| AU2006210040B2 (en) | 2011-04-14 |
| 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 |
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