NO316977B1 - S-substituerte 11<beta>-benzaldoksim-ostra-4,9-dien-karboksylsyretiolestere, fremgangsmate for deres fremstilling, farmasoytiske preparater inneholdende disse forbindelser, samt anvendelse av forbindelsene til fremstilling av medikamenter og prevensjonsmi - Google Patents

S-substituerte 11<beta>-benzaldoksim-ostra-4,9-dien-karboksylsyretiolestere, fremgangsmate for deres fremstilling, farmasoytiske preparater inneholdende disse forbindelser, samt anvendelse av forbindelsene til fremstilling av medikamenter og prevensjonsmi Download PDF

Info

Publication number: NO316977B1
Authority: NO; Norway
Prior art keywords: benzaldehyde; dien; oxoestra; oxime; carbonyl
Prior art date: 1998-03-03

Application number

NO20004362A

Other languages

English (en)

Norwegian (no)

Other versions

NO20004362D0 (no

NO20004362L (no

Inventor

Walter Elger

Gerd Schubert

Guenther Kaufmann

Sven Ring

Birgit Schneider

Original Assignee

Schering Ag

Priority date (The priority date 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 date listed.)

1998-03-03

Filing date

2000-09-01

Publication date

2004-07-12

2000-09-01 Application filed by Schering Ag filed Critical Schering Ag

2000-09-01 Publication of NO20004362D0 publication Critical patent/NO20004362D0/no

2000-10-31 Publication of NO20004362L publication Critical patent/NO20004362L/no

2004-07-12 Publication of NO316977B1 publication Critical patent/NO316977B1/no

Links

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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/46—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of glucocorticosteroids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/006—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton spiro-condensed

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Endocrinology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Diabetes (AREA)
Reproductive Health (AREA)
Gynecology & Obstetrics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

NO20004362A 1998-03-03 2000-09-01 S-substituerte 11<beta>-benzaldoksim-ostra-4,9-dien-karboksylsyretiolestere, fremgangsmate for deres fremstilling, farmasoytiske preparater inneholdende disse forbindelser, samt anvendelse av forbindelsene til fremstilling av medikamenter og prevensjonsmi NO316977B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19809845A DE19809845A1 (de)	1998-03-03	1998-03-03	S-substituierte 11beta-Benzaldoxim-estra-4,9-dien-kohlensäurethiolester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen
PCT/DE1999/000408 WO1999045023A1 (de)	1998-03-03	1999-02-10	S-SUBSTITUIERTE 11β-BENZALDOXIM-ESTRA-4,9-DIEN-KOHLENSÄURETHIOLESTER, VERFAHREN ZU DEREN HERSTELLUNG UND DIESE VERBINDUNGEN ENTHALTENE PHARMAZEUTISCHE ZUBEREITUNGEN

Publications (3)

Publication Number	Publication Date
NO20004362D0 NO20004362D0 (no)	2000-09-01
NO20004362L NO20004362L (no)	2000-10-31
NO316977B1 true NO316977B1 (no)	2004-07-12

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NO20004362A NO316977B1 (no)	1998-03-03	2000-09-01	S-substituerte 11<beta>-benzaldoksim-ostra-4,9-dien-karboksylsyretiolestere, fremgangsmate for deres fremstilling, farmasoytiske preparater inneholdende disse forbindelser, samt anvendelse av forbindelsene til fremstilling av medikamenter og prevensjonsmi

Country Status (28)

Country	Link
US (1)	US6365582B1 (xx)
EP (1)	EP1060187B1 (xx)
JP (1)	JP3796405B2 (xx)
KR (1)	KR100488823B1 (xx)
CN (1)	CN1208341C (xx)
AT (1)	ATE237627T1 (xx)
AU (1)	AU749163B2 (xx)
BG (1)	BG64735B1 (xx)
BR (1)	BR9908458A (xx)
CA (1)	CA2322471C (xx)
CZ (1)	CZ20003125A3 (xx)
DE (2)	DE19809845A1 (xx)
DK (1)	DK1060187T3 (xx)
EA (1)	EA002766B1 (xx)
EE (1)	EE04242B1 (xx)
ES (1)	ES2197634T3 (xx)
HU (1)	HUP0100962A3 (xx)
ID (1)	ID26972A (xx)
IL (1)	IL137851A (xx)
IS (1)	IS5579A (xx)
NO (1)	NO316977B1 (xx)
NZ (1)	NZ506048A (xx)
PL (1)	PL193687B1 (xx)
PT (1)	PT1060187E (xx)
SK (1)	SK284177B6 (xx)
TR (1)	TR200002506T2 (xx)
UA (1)	UA59437C2 (xx)
WO (1)	WO1999045023A1 (xx)

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Publication number	Priority date	Publication date	Assignee	Title
DE19906152B4 (de)	1999-02-10	2005-02-10	Jenapharm Gmbh & Co. Kg	Wirkstoffhaltige Laminate für Transdermalsysteme
PT1229906E (pt) *	1999-08-31	2008-01-18	Bayer Schering Pharma Ag	Mesoprogestinas para o tratamento e prevenção de distúrbios ginecológicos hormonodependentes benignos
RO122180B1 (ro) *	1999-08-31	2009-02-27	Jenapharm Gmbh & Co. Kg	Utilizarea mezoprogestinelor în terapia de substituţie hormonală
US7629334B1 (en) *	1999-08-31	2009-12-08	Bayer Schering Pharma Aktiengesellschaft	Mesoprogrestins (progesterone receptor modulations) as a component of compositions for hormone replacement therapy (HRT)
US8193252B1 (en)	1999-08-31	2012-06-05	Bayer Pharma AG	Mesoprogestins (progesterone receptor modulators) for the treatment and prevention of benign hormone dependent gynecological disorders
SI20853A (sl) *	1999-08-31	2002-10-31	Jenapharm Gmbh & Co. Kg	Mezoprogestini (modulatorji receptorja progesterona) kot sestavina ženskih kontraceptivov
EP1285927A3 (de) *	2001-08-16	2005-06-29	Schering Aktiengesellschaft	Verwendung von Glucocorticoid-Rezeptorantagonisten zur Vorbeugung und Behandlung von Erkrankungen des männlichen Reproduktionssystems
DE10221034A1 (de) *	2002-05-03	2003-11-20	Schering Ag	17alpha-Fluoralkyl-11ß-benzaldoxim-Steroide, Verfahren zu deren Herstellung, diese Steroide enthaltende pharmazeutische Präparate sowie deren Verwendung zur Herstellung von Arzneimitteln
DE10236405A1 (de) *	2002-08-02	2004-02-19	Schering Ag	Progesteronrezeptormodulatoren mit erhöhter antigonadotroper Aktivität für die weibliche Fertilitätskontrolle und Hormonersatztherapie
JP2005539016A (ja) *	2002-08-02	2005-12-22	シエーリングアクチエンゲゼルシャフト	女性用受胎調節及びホルモン置換療法のための高められた抗ゴナドトロピン活性を有するプロゲステロン受容体モジュレーター
DE102005059222B4 (de) *	2005-12-08	2007-10-11	Bayer Schering Pharma Ag	11ß-Benzaldoximderivate von D-Homoestra-4,9-dien-3-onen
HUE036870T2 (hu)	2006-10-24	2018-08-28	Repros Therapeutics Inc	Az endometriális proliferáció elnyomására szolgáló készítmények és módszerek
JP5583976B2 (ja) *	2007-03-07	2014-09-03	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	選択的プロゲステロン受容体モジュレーターとしてのステロイド誘導体
TWI539953B (zh)	2008-04-28	2016-07-01	瑞波若斯治療學公司	用於治療乳癌之組成物和方法
DE102009034525A1 (de) *	2009-07-21	2011-01-27	Bayer Schering Pharma Aktiengesellschaft	17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-aryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten
US20130018027A1 (en)	2010-03-22	2013-01-17	Repros Therapeutics Inc.	Compositions and methods for non-toxic delivery of antiprogestins
EP2664325A1 (en) *	2012-05-16	2013-11-20	PregLem S.A.	Methods for preventing or treating androgen mediated diseases

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4039677A (en) *	1976-03-01	1977-08-02	Syntex (U.S.A.) Inc.	Novel 1-phenethylimidazoles
ZA8231B (en) *	1981-01-09	1982-11-24	Roussel Uclaf	New 11 -substituted steroid derivatives, their preparation, their use as medicaments, the compositions containing them and the new intermediates thus obtained
DE3504421A1 (de) *	1985-02-07	1986-08-07	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue 11ss-phenyl-gonane, deren herstellung und diese enthaltende pharmazeutische praeparate
DE4332283A1 (de) *	1993-09-20	1995-04-13	Jenapharm Gmbh	Neue 11-Benzaldoximestradien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE4332284C2 (de) *	1993-09-20	1997-05-28	Jenapharm Gmbh	11-Benzaldoxim-17beta-methoxy-17alpha-methoxymethyl-estradien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
US5576310A (en) *	1994-09-20	1996-11-19	Jenapharm Gmbh	11-benzaldoxime-17β-methoxy-17α-methoxymethyl-estrasdiene derivatives, methods for their production and pharmaceuticals containing such compounds
NZ295365A (en)	1994-10-24	1999-07-29	Schering Ag	Competitive progesterone antagonists for regulating female fertility as required
ZA9510926B (en)	1994-12-23	1996-07-03	Schering Ag	Compounds with progesterone-antagonistic and antiestrogenic action to be used together for female contraception
CA2214779A1 (en)	1995-03-14	1996-09-19	Schering Aktiengesellschaft	Use of nitric oxide donor and/or substrate for inducing cervical dilation

1998
- 1998-03-03 DE DE19809845A patent/DE19809845A1/de not_active Ceased
1999
- 1999-02-10 CZ CZ20003125A patent/CZ20003125A3/cs unknown
- 1999-02-10 WO PCT/DE1999/000408 patent/WO1999045023A1/de not_active Ceased
- 1999-02-10 PL PL99342449A patent/PL193687B1/pl unknown
- 1999-02-10 KR KR10-2000-7009712A patent/KR100488823B1/ko not_active Expired - Fee Related
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- 1999-02-10 CA CA002322471A patent/CA2322471C/en not_active Expired - Fee Related
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- 1999-02-10 DK DK99915475T patent/DK1060187T3/da active
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- 1999-02-10 EA EA200000896A patent/EA002766B1/ru not_active IP Right Cessation
- 1999-02-10 AU AU34067/99A patent/AU749163B2/en not_active Ceased
- 1999-02-10 US US09/622,803 patent/US6365582B1/en not_active Expired - Fee Related
- 1999-02-10 BR BR9908458-9A patent/BR9908458A/pt not_active Application Discontinuation
- 1999-02-10 DE DE59905075T patent/DE59905075D1/de not_active Expired - Fee Related
- 1999-02-10 IL IL13785199A patent/IL137851A/xx not_active IP Right Cessation
- 1999-02-10 NZ NZ506048A patent/NZ506048A/en unknown
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- 1999-02-10 HU HU0100962A patent/HUP0100962A3/hu unknown
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- 1999-02-10 EP EP99915475A patent/EP1060187B1/de not_active Expired - Lifetime
- 1999-02-10 TR TR2000/02506T patent/TR200002506T2/xx unknown
- 1999-10-02 UA UA2000105635A patent/UA59437C2/uk unknown
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- 2000-07-28 IS IS5579A patent/IS5579A/is unknown
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Also Published As

Publication number	Publication date
DK1060187T3 (da)	2003-08-11
EA200000896A1 (ru)	2001-04-23
NZ506048A (en)	2003-05-30
WO1999045023A1 (de)	1999-09-10
NO20004362D0 (no)	2000-09-01
CA2322471C (en)	2007-04-24
HUP0100962A3 (en)	2002-07-29
AU3406799A (en)	1999-09-20
PL342449A1 (en)	2001-06-04
IL137851A0 (en)	2001-10-31
UA59437C2 (uk)	2003-09-15
JP3796405B2 (ja)	2006-07-12
IL137851A (en)	2005-06-19
CA2322471A1 (en)	1999-09-10
CN1291990A (zh)	2001-04-18
EA002766B1 (ru)	2002-08-29
CZ20003125A3 (cs)	2002-01-16
ATE237627T1 (de)	2003-05-15
BR9908458A (pt)	2000-11-14
NO20004362L (no)	2000-10-31
BG64735B1 (bg)	2006-01-31
JP2002505335A (ja)	2002-02-19
CN1208341C (zh)	2005-06-29
AU749163B2 (en)	2002-06-20
ID26972A (id)	2001-02-22
US6365582B1 (en)	2002-04-02
PT1060187E (pt)	2003-09-30
DE19809845A1 (de)	1999-09-09
IS5579A (is)	2000-07-28
PL193687B1 (pl)	2007-03-30
KR20010041536A (ko)	2001-05-25
EP1060187A1 (de)	2000-12-20
TR200002506T2 (tr)	2000-12-21
SK13052000A3 (sk)	2001-11-06
ES2197634T3 (es)	2004-01-01
EE04242B1 (et)	2004-02-16
EP1060187B1 (de)	2003-04-16
HUP0100962A2 (hu)	2001-09-28
BG104712A (en)	2001-02-28
SK284177B6 (sk)	2004-10-05
KR100488823B1 (ko)	2005-05-12
DE59905075D1 (de)	2003-05-22
EE200000500A (et)	2002-02-15

Publication	Publication Date	Title
NO316977B1 (no)	2004-07-12	S-substituerte 11<beta>-benzaldoksim-ostra-4,9-dien-karboksylsyretiolestere, fremgangsmate for deres fremstilling, farmasoytiske preparater inneholdende disse forbindelser, samt anvendelse av forbindelsene til fremstilling av medikamenter og prevensjonsmi
JP2753562B2 (ja)	1998-05-20	新規な１１−ベンズアルドキシム−エストラ−ジエン誘導体とその製造方法、及びその化合物を含有する医薬製剤
JP2696672B2 (ja)	1998-01-14	新規な１１−ベンズアルドキシム−１７β−メトキシ−１７α−メトキシメチル−エストラジエン誘導体、その製法およびその物質を含有する医薬製剤
AU8020887A (en)	1988-04-07	17 alpha-(substituted-methyl)-17 beta-hydroxy/esterified hydroxy steroids and pharmaceutical compositions containing them
US5576310A (en)	1996-11-19	11-benzaldoxime-17β-methoxy-17α-methoxymethyl-estrasdiene derivatives, methods for their production and pharmaceuticals containing such compounds
US7550451B2 (en)	2009-06-23	Progesterone receptor modulators with increased antigonadotropic activity for female birth control and hormone replacement therapy
JP2005539016A (ja)	2005-12-22	女性用受胎調節及びホルモン置換療法のための高められた抗ゴナドトロピン活性を有するプロゲステロン受容体モジュレーター
RU2137777C1 (ru)	1999-09-20	ПРОИЗВОДНЫЕ 11β-БЕНЗАЛЬДОКСИМ-ЭСТРА-4,9-ДИЕНА, СПОСОБ ИХ ПОЛУЧЕНИЯ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ
MXPA00007612A (en)	2002-06-05	S-SUBSTITUTED 11&bgr;-BENZALDOXIME-ESTRA-4,9-DIENE-CARBONIC ACID THIOLESTERS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING THESE COMPOUNDS
HK1036071A (en)	2001-12-21	S-SUBSTITUTED 11β-BENZALDOXIME-ESTRA-4,9-DIENE-CARBONIC ACID THIOLESTERS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING THESE COMPOUNDS
HK1120519A (en)	2009-04-03	Novel c18 modified retrosteroids as progesterone receptor modulator compounds