AU2006210040B9 - Isolation of N-butylbenzenesulfonamide, synthesis of benzenesulfonamide derivatives, and use of N-butylbenzenesulfonamide and benzenesulfonamide derivatives for the treatment of benign prostate hyperplasia and/or prostate carcinoma - Google Patents
Isolation of N-butylbenzenesulfonamide, synthesis of benzenesulfonamide derivatives, and use of N-butylbenzenesulfonamide and benzenesulfonamide derivatives for the treatment of benign prostate hyperplasia and/or prostate carcinomaInfo
- Publication number
- AU2006210040B9 AU2006210040B9 AU2006210040A AU2006210040A AU2006210040B9 AU 2006210040 B9 AU2006210040 B9 AU 2006210040B9 AU 2006210040 A AU2006210040 A AU 2006210040A AU 2006210040 A AU2006210040 A AU 2006210040A AU 2006210040 B9 AU2006210040 B9 AU 2006210040B9
- Authority
- AU
- Australia
- Prior art keywords
- hydrogen
- residue
- completely
- nitro group
- aliphatic
- 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.)
- Ceased
Links
- IPRJXAGUEGOFGG-UHFFFAOYSA-N N-butylbenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=CC=C1 IPRJXAGUEGOFGG-UHFFFAOYSA-N 0.000 title claims description 121
- 206010060862 Prostate cancer Diseases 0.000 title claims description 47
- 201000001514 prostate carcinoma Diseases 0.000 title claims description 36
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 title claims description 32
- 150000008331 benzenesulfonamides Chemical class 0.000 title claims description 24
- 238000011282 treatment Methods 0.000 title claims description 22
- 238000002955 isolation Methods 0.000 title claims description 7
- 230000015572 biosynthetic process Effects 0.000 title description 36
- 238000003786 synthesis reaction Methods 0.000 title description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 95
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 239000000284 extract Substances 0.000 claims description 31
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 24
- 229930195733 hydrocarbon Natural products 0.000 claims description 22
- 150000002430 hydrocarbons Chemical class 0.000 claims description 22
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- 239000004215 Carbon black (E152) Substances 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical group CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
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- 239000003098 androgen Substances 0.000 claims description 13
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- 150000003139 primary aliphatic amines Chemical class 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 7
- 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 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
- -1 C 4 alcohols Chemical class 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000051 antiandrogen Substances 0.000 claims description 6
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- 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
- 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
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- 229910052736 halogen Inorganic materials 0.000 claims description 3
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- 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
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- 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 2
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- 206010020718 hyperplasia Diseases 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 58
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- 230000000694 effects Effects 0.000 description 12
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- 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
- 229940124530 sulfonamide Drugs 0.000 description 9
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- 150000003456 sulfonamides Chemical class 0.000 description 8
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-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
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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- 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 3
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Classifications
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- 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)
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- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
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- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
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- 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 |
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| AU2006210040A1 AU2006210040A1 (en) | 2006-08-10 |
| AU2006210040B2 AU2006210040B2 (en) | 2011-04-14 |
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| EP (1) | EP1845963A2 (enExample) |
| JP (1) | JP5191238B2 (enExample) |
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| AU (1) | AU2006210040B9 (enExample) |
| BR (1) | BRPI0606563A2 (enExample) |
| CA (1) | CA2596618C (enExample) |
| DE (1) | DE102005005397B4 (enExample) |
| 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 |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4997847A (en) * | 1987-08-20 | 1991-03-05 | Smith Kline & French Laboratories Limited | Biologically active compounds |
| US5723407A (en) * | 1993-08-16 | 1998-03-03 | Meiji Seika Kaisha, Ltd. | Sulfonylsemicarbazide derivatives and preservative composition for preserving the freshness of flower of cut flowers |
| WO1999050272A1 (en) * | 1998-03-30 | 1999-10-07 | Guilford Pharmaceuticals Inc. | Phosphinic acid derivatives |
| EP1085011A1 (en) * | 1999-09-15 | 2001-03-21 | Oridigm Corporation | Novel polyamine analogues as therapeutic and diagnostic agents |
| US6365605B1 (en) * | 1997-06-24 | 2002-04-02 | Les Laboratoires Servier | Substituted hydrochromenopyrroles |
| WO2005016859A2 (en) * | 2003-08-14 | 2005-02-24 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
| US20050107307A1 (en) * | 2003-08-14 | 2005-05-19 | Raffaella Bernadini | Proteasome inhibitors and methods of using the same |
| US20050267075A1 (en) * | 2004-05-21 | 2005-12-01 | Allen David R | Sulfonylethyl phosphorodiamidates |
| US20060047123A1 (en) * | 2004-09-02 | 2006-03-02 | Saleh Ahmed | Mercaptoamides as histone deacetylase inhibitors |
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| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
-
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
- 2007-07-17 ZA ZA200706061A patent/ZA200706061B/en unknown
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| US4997847A (en) * | 1987-08-20 | 1991-03-05 | Smith Kline & French Laboratories Limited | Biologically active compounds |
| US5723407A (en) * | 1993-08-16 | 1998-03-03 | Meiji Seika Kaisha, Ltd. | Sulfonylsemicarbazide derivatives and preservative composition for preserving the freshness of flower of cut flowers |
| US6365605B1 (en) * | 1997-06-24 | 2002-04-02 | Les Laboratoires Servier | Substituted hydrochromenopyrroles |
| WO1999050272A1 (en) * | 1998-03-30 | 1999-10-07 | Guilford Pharmaceuticals Inc. | Phosphinic acid derivatives |
| EP1085011A1 (en) * | 1999-09-15 | 2001-03-21 | Oridigm Corporation | Novel polyamine analogues as therapeutic and diagnostic agents |
| WO2005016859A2 (en) * | 2003-08-14 | 2005-02-24 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
| US20050107307A1 (en) * | 2003-08-14 | 2005-05-19 | Raffaella Bernadini | Proteasome inhibitors and methods of using the same |
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| US20060047123A1 (en) * | 2004-09-02 | 2006-03-02 | Saleh Ahmed | Mercaptoamides as histone deacetylase inhibitors |
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 |
| 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 |
| EP1845963A2 (de) | 2007-10-24 |
| KR20070100844A (ko) | 2007-10-11 |
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