AU2004213148A1 - Antitumoral D-homoestra-1, 3, 5 (10)-trien-3-yl 2-substituted sulfamates - Google Patents
Antitumoral D-homoestra-1, 3, 5 (10)-trien-3-yl 2-substituted sulfamates Download PDFInfo
- Publication number
- AU2004213148A1 AU2004213148A1 AU2004213148A AU2004213148A AU2004213148A1 AU 2004213148 A1 AU2004213148 A1 AU 2004213148A1 AU 2004213148 A AU2004213148 A AU 2004213148A AU 2004213148 A AU2004213148 A AU 2004213148A AU 2004213148 A1 AU2004213148 A1 AU 2004213148A1
- Authority
- AU
- Australia
- Prior art keywords
- trien
- sulfamate
- methoxy
- homoestra
- dihomoestra
- 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.)
- Abandoned
Links
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10307103.2 | 2003-02-19 | ||
| DE10307103A DE10307103A1 (de) | 2003-02-19 | 2003-02-19 | Antitumor wirksame 2-substituierte D-Homostra-1,3,5(10)-trien-3-yl sulfamate |
| PCT/EP2004/001629 WO2004074309A1 (de) | 2003-02-19 | 2004-02-19 | Antitumor wirksame 2-substituierte d-homoestra-1,3,5(10)-trien-3-yl sulfamate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2004213148A1 true AU2004213148A1 (en) | 2004-09-02 |
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|---|---|---|---|
| AU2004213148A Abandoned AU2004213148A1 (en) | 2003-02-19 | 2004-02-19 | Antitumoral D-homoestra-1, 3, 5 (10)-trien-3-yl 2-substituted sulfamates |
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| Country | Link |
|---|---|
| US (2) | US7244762B2 (enExample) |
| EP (1) | EP1594886B1 (enExample) |
| JP (1) | JP4718439B2 (enExample) |
| CN (1) | CN100343272C (enExample) |
| AT (1) | ATE406375T1 (enExample) |
| AU (1) | AU2004213148A1 (enExample) |
| BR (1) | BRPI0407681A (enExample) |
| CA (1) | CA2516184A1 (enExample) |
| DE (2) | DE10307103A1 (enExample) |
| ES (1) | ES2312965T3 (enExample) |
| MX (1) | MXPA05008833A (enExample) |
| RU (1) | RU2005128830A (enExample) |
| WO (1) | WO2004074309A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10307103A1 (de) | 2003-02-19 | 2004-09-09 | Schering Ag | Antitumor wirksame 2-substituierte D-Homostra-1,3,5(10)-trien-3-yl sulfamate |
| DE102004032673A1 (de) * | 2004-07-02 | 2006-01-26 | Schering Ag | Neue 2-substituierte D-Homo-estra-1,3,5(10)-triene als Inhibitoren der 17ß-Hydroxysteroiddehydrogenase Typ 1 |
| US7435757B2 (en) | 2004-07-02 | 2008-10-14 | Schering Ag | 2-substituted D-homo-estra-1,3,5(10)-trienes as inhibitors of 17β-hydroxy steroid dehydrogenase type 1 |
| RU2629186C1 (ru) * | 2016-07-28 | 2017-08-25 | Федеральное государственное автономное образовательное учреждение высшего образования "Дальневосточный федеральный университет" (ДВФУ) | Рацемический 2,17аβ-дисульфамоилокси-3-метокси-D-гомо-8α-эстра-1,3,5(10)-триен в качестве ингибитора пролиферации опухолевых клеток MCF-7 |
| RU2680603C1 (ru) * | 2018-11-08 | 2019-02-25 | Ильясов Шамиль Сионович | Применение 3-о-сульфамата-16,16-диметил-d-гомоэквиленина для лечения онкологических заболеваний |
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| DK465481A (da) * | 1980-11-21 | 1982-05-22 | Hoffmann La Roche | Fremgangsmaade til fremstilling af d-homostemoider |
| US6011024A (en) * | 1991-08-28 | 2000-01-04 | Imperial College Of Science Technology & Medicine | Steroid sulphatase inhibitors |
| GB9625334D0 (en) * | 1996-12-05 | 1997-01-22 | Imperial College | Compound |
| GB9118478D0 (en) * | 1991-08-29 | 1991-10-16 | Imperial College | Steroid sulphatase inhibitors |
| US6903084B2 (en) * | 1991-08-28 | 2005-06-07 | Sterix Limited | Steroid sulphatase inhibitors |
| US6908910B2 (en) | 1993-08-06 | 2005-06-21 | The Children's Medical Center Corporation | Estrogenic compounds as anti-mitotic agents |
| DE4429397C2 (de) * | 1994-08-09 | 2003-11-20 | Jenapharm Gmbh | Estra-1,3,5(10)-trien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
| DE4429398C2 (de) * | 1994-08-09 | 1997-09-11 | Jenapharm Gmbh | Verwendung von Estra-1,3,5(10)-trien-Derivaten zur hormonalen Kontrazeption |
| DE19540233B4 (de) * | 1995-10-19 | 2005-08-25 | Schering Ag | Sulfamat-Derivate von 1,3,5(10)-Estratrien-Derivaten, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
| US5705495A (en) | 1995-10-19 | 1998-01-06 | Jenapharm Gmbh & Co. Kg. | Sulfamate derivatives of 1,3,5(10)-estratriene derivatives, methods for their production and pharmaceuticals containing these compounds |
| US20040127473A1 (en) * | 1996-12-05 | 2004-07-01 | Reed Michael John | Compound |
| DE19712488A1 (de) * | 1997-03-25 | 1998-10-01 | Knoell Hans Forschung Ev | Steroidsulfamate, Verfahren zu ihrer Herstellung und Anwendung derselben |
| GB2331988B (en) * | 1997-12-04 | 2003-04-16 | Imperial College | Polycyclic sulphamate inhibitors or oestrone sulphatase |
| US6054446A (en) * | 1997-12-24 | 2000-04-25 | Sri International | Anti-estrogenic steroids, and associated pharmaceutical compositions and methods of use |
| US6548491B2 (en) | 1997-12-24 | 2003-04-15 | Sri International | Anti-estrogenic steroids, and associated pharmaceutical compositions and methods of use |
| US6046186A (en) * | 1997-12-24 | 2000-04-04 | Sri International | Estrone sulfamate inhibitors of estrone sulfatase, and associated pharmaceutical compositions and methods of use |
| ATE401896T1 (de) * | 1998-06-10 | 2008-08-15 | Sterix Ltd | Pharmazeutische zusammensetzungen mit tumor nekrose faktor und 2-methoxyestron-3-o-sulphamat als estrone sulphatasehemmern |
| GB9913536D0 (en) * | 1999-06-10 | 1999-08-11 | Sterix Ltd | Use |
| DE19943708B4 (de) * | 1999-09-08 | 2007-12-20 | Bayer Schering Pharma Ag | Neue C13-substituierte Estra-1,3,5(10)-trien-3-yl-sulfamate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
| US6583130B1 (en) * | 1999-09-13 | 2003-06-24 | Schering Ag | C13-substituted estra-1,3,5,(10)-trien-3-yl sulfamates, methods of preparing same, and pharmaceutical compositions containing these compounds |
| AU1199701A (en) * | 1999-10-26 | 2001-05-08 | Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The | B-homoestra-1,3,5(10)-trienes as modulators of tubulin polymerization |
| GB0025788D0 (en) * | 2000-10-20 | 2000-12-06 | Sterix Ltd | Use |
| AU8838601A (en) | 2000-11-27 | 2002-06-03 | Entremed Inc | Antiangiogenic agents |
| GB2371299A (en) * | 2001-01-17 | 2002-07-24 | Sabbir Ahmed | Sulfamate oestrone sulfatase inhibitors |
| DE10114364A1 (de) * | 2001-03-22 | 2002-10-02 | Heraeus Kulzer Gmbh & Co Kg | Verfahren zur Herstellung von antibiotischen Kompositen |
| DE10307103A1 (de) | 2003-02-19 | 2004-09-09 | Schering Ag | Antitumor wirksame 2-substituierte D-Homostra-1,3,5(10)-trien-3-yl sulfamate |
| DE10307105A1 (de) * | 2003-02-19 | 2004-09-09 | Schering Ag | Antitumor wirksame 2-substituierte 18a-Homoestra-1,3,5(10)-trien-3-yl sulfamate |
| DE10307104A1 (de) * | 2003-02-19 | 2004-09-23 | Schering Ag | Antitumor wirksame 2-substituierte Estra-1,3,5(10)-trien-3-yl sulfamate |
-
2003
- 2003-02-19 DE DE10307103A patent/DE10307103A1/de not_active Ceased
-
2004
- 2004-02-19 JP JP2006501900A patent/JP4718439B2/ja not_active Expired - Fee Related
- 2004-02-19 AT AT04712555T patent/ATE406375T1/de not_active IP Right Cessation
- 2004-02-19 CN CNB2004800045952A patent/CN100343272C/zh not_active Expired - Fee Related
- 2004-02-19 US US10/546,230 patent/US7244762B2/en not_active Ceased
- 2004-02-19 EP EP04712555A patent/EP1594886B1/de not_active Expired - Lifetime
- 2004-02-19 DE DE502004007950T patent/DE502004007950D1/de not_active Expired - Lifetime
- 2004-02-19 ES ES04712555T patent/ES2312965T3/es not_active Expired - Lifetime
- 2004-02-19 AU AU2004213148A patent/AU2004213148A1/en not_active Abandoned
- 2004-02-19 WO PCT/EP2004/001629 patent/WO2004074309A1/de not_active Ceased
- 2004-02-19 MX MXPA05008833A patent/MXPA05008833A/es not_active Application Discontinuation
- 2004-02-19 BR BRPI0407681-8A patent/BRPI0407681A/pt not_active IP Right Cessation
- 2004-02-19 CA CA002516184A patent/CA2516184A1/en not_active Abandoned
- 2004-02-19 US US12/351,271 patent/USRE42132E1/en not_active Expired - Fee Related
- 2004-02-19 RU RU2005128830/04A patent/RU2005128830A/ru not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004074309A8 (de) | 2004-12-16 |
| BRPI0407681A (pt) | 2006-03-01 |
| DE10307103A1 (de) | 2004-09-09 |
| CN1751061A (zh) | 2006-03-22 |
| ATE406375T1 (de) | 2008-09-15 |
| EP1594886B1 (de) | 2008-08-27 |
| RU2005128830A (ru) | 2007-03-27 |
| ES2312965T3 (es) | 2009-03-01 |
| CA2516184A1 (en) | 2004-09-02 |
| MXPA05008833A (es) | 2005-10-05 |
| US7244762B2 (en) | 2007-07-17 |
| US20060154985A1 (en) | 2006-07-13 |
| CN100343272C (zh) | 2007-10-17 |
| USRE42132E1 (en) | 2011-02-08 |
| JP2006517946A (ja) | 2006-08-03 |
| DE502004007950D1 (en) | 2008-10-09 |
| WO2004074309A1 (de) | 2004-09-02 |
| EP1594886A1 (de) | 2005-11-16 |
| DE10307103A8 (de) | 2004-12-16 |
| JP4718439B2 (ja) | 2011-07-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |