FI113657B - Förfarande för framställning av 11beeta-bensaldoxim-estra-4,9-dien-derivat för användning i farmaceutiska sammansättningar - Google Patents
Förfarande för framställning av 11beeta-bensaldoxim-estra-4,9-dien-derivat för användning i farmaceutiska sammansättningar Download PDFInfo
- Publication number
- FI113657B FI113657B FI943687A FI943687A FI113657B FI 113657 B FI113657 B FI 113657B FI 943687 A FI943687 A FI 943687A FI 943687 A FI943687 A FI 943687A FI 113657 B FI113657 B FI 113657B
- Authority
- FI
- Finland
- Prior art keywords
- phenyl
- estra
- dien
- hydroxy
- carbon atoms
- Prior art date
Links
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
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
-
- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
- A61P35/00—Antineoplastic agents
-
- 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
- A61P5/32—Antioestrogens
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Toxicology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (3)
1. Förfarande för framställning av Ιΐβ-bensaldoxim-estra-4,9-dien-derivat med den allmänna formeln I för användning i farmaceutiska sammansättningar med antigestagen verkning, NOZ i OR2 1 : ^_I (I) * i vilken R1 är en alkylgrupp innehällande 1-6 kolatomer, • R2 är en väteatom eller en alkylgrupp innehällande 1-6 • kolatomer,
20 R3 är -CH X, , 2 • i vilken X är en halogen eller gruppen ORs, varvid R5 är en alkylgrupp innehällande 1-6 kolatomer, 113657 eller gruppen C=CR7, i vilken R7 är en hydroxialkylgrupp innehällande 1-6 kolatomer, Z är en väteatom, en alkylgrupp innehällande 1-6 kolatomer, 5 gruppen -CONH-fenyl eller -COOR4, i vilken R4 är en alkylgrupp innehällande 1-6 kolatomer, kännetecknat av att en förening med den allmänna formeln II o ^1^1 (ll) ’· 10 i vilken R1, R2 ja R3 betecknar detsamma som ovan, * · , . fär reagera med en förening med den allmänna formeln Ha : NH -O-Y (Ha) 2 » · I vilken Y betecknar detsamma som Z ovan, och varvid en förening med den allmänna formeln Ha eventu-: · 15 elit är en dylik förening, eller en förening med den all männa formeln Ha separeras under valda reaktionsförhällan-: den, * » * och varvid en eventuellt förekommande hydroxylamingrupp för esteras eller för etras. 20 2. Förfarande enligt patentkrav 1, kännetecknat av att föl- jande föreningar framställs: 113657 11β- [4- (hydroxi-iminometyl) fenyl] -17β-1ιγάηοχϊ-17α-π^οχϊ-metyl-estra-4,9-dien-3-on, 11β- [4- (hydroxi-iminometyl) fenyl] -17p-metoxi-17a-metoxime-tyl-estra-4,9-dien-3-on, 5 11β-[4-(hydroxi-iminometyl)fenyl]-17β-1^άηοχί-17α-(3-hydr- oxiprop-l-in-yl)-estra-4,9-dien-3-on, 17(x-klormetyl-l^- [4- (hydroxi-iminometyl) fenyl] -17β-ϊ^άΓ-oxi-estra-4,9-dien-3-on, 11β— [4- (metyloxi-iminometyl) fenyl] -17β-ιηβ^χί-17α-:π·^οχίιηθ-10 tyl-estra-4,9-dien-3-on, 11β— [4- (acetoxi-iminometyl) fenyl] -17β-ιη6^χί-17(χ-ιηβ^χίιη6-tyl-estra-4,9-dien-3-on, 11β-{4- [ (etoxikarbonyl) oxi-iminometyl] fenyl}-17β-π^οχϊ-17a-metoximetyl-estra-4,9-dien-3-on, 15 17β-metoxi-17(χ-metoximetyl-llβ-{4-[(fenylaminokarbonyl)oxi- iminometyl] fenyl}-estra-4,9-dien-3-on, 17a-etoximetyl-l^- [4- (hydroxi-iminometyl) fenyl] -17β-ιηθ^ oxi-estra-4,9-dien-3-on, och ·. 17a-etoximetyl-l^- [4- (hydroxi-iminometyl) fenyl] -17p-hydr- :, 20 oxi-estra-4,9-dien-3-on. *
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4332283A DE4332283A1 (de) | 1993-09-20 | 1993-09-20 | Neue 11-Benzaldoximestradien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
DE4332283 | 1993-09-20 | ||
US30917594 | 1994-09-20 | ||
US08/309,175 US5693628A (en) | 1993-09-20 | 1994-09-20 | 11-benzaldoxime-estra-diene derivatives, methods for their production and pharmaceuticals containing these compounds |
Publications (3)
Publication Number | Publication Date |
---|---|
FI943687A0 FI943687A0 (sv) | 1994-08-09 |
FI943687A FI943687A (sv) | 1995-03-21 |
FI113657B true FI113657B (sv) | 2004-05-31 |
Family
ID=25929786
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI943687A FI113657B (sv) | 1993-09-20 | 1994-08-09 | Förfarande för framställning av 11beeta-bensaldoxim-estra-4,9-dien-derivat för användning i farmaceutiska sammansättningar |
Country Status (16)
Country | Link |
---|---|
US (1) | US5693628A (sv) |
EP (1) | EP0648778B1 (sv) |
JP (1) | JP2753562B2 (sv) |
AT (1) | ATE156835T1 (sv) |
AU (1) | AU682195B2 (sv) |
CA (1) | CA2130516C (sv) |
CZ (1) | CZ292298B6 (sv) |
DE (2) | DE4332283A1 (sv) |
DK (1) | DK0648778T3 (sv) |
ES (1) | ES2108371T3 (sv) |
FI (1) | FI113657B (sv) |
HU (1) | HU223339B1 (sv) |
NO (1) | NO304989B1 (sv) |
NZ (1) | NZ264229A (sv) |
PL (1) | PL183181B1 (sv) |
SK (1) | SK280137B6 (sv) |
Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
DE19548450A1 (de) * | 1995-12-22 | 1997-06-26 | Jenapharm Gmbh | 17alpha-Cyanomethylestra-4,9-dien-3-on-17beta-yl- derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
DE19745085A1 (de) * | 1997-10-11 | 1999-04-15 | Jenapharm Gmbh | 11ß-Benzaldoxim-9alpha,10alpha-epoxy-estr-4-en-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate |
DE19809845A1 (de) | 1998-03-03 | 1999-09-09 | Jenapharm Gmbh | S-substituierte 11beta-Benzaldoxim-estra-4,9-dien-kohlensäurethiolester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen |
DE19906152B4 (de) | 1999-02-10 | 2005-02-10 | Jenapharm Gmbh & Co. Kg | Wirkstoffhaltige Laminate für Transdermalsysteme |
PL353994A1 (en) * | 1999-08-31 | 2003-12-15 | Jenapharm Gmbh & Co.Kgjenapharm Gmbh & Co.Kg | Mesoprogestins (progesterone receptor modulators) as a component of female contraceptives |
CZ301412B6 (cs) | 1999-08-31 | 2010-02-24 | Bayer Schering Pharma Aktiengesellschaft | Použití specifických mesoprogestinu jako farmaceutické složky pro výrobu léciva pro hormonální substitucní lécbu |
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) |
KR100864547B1 (ko) * | 1999-08-31 | 2008-10-20 | 바이엘 쉐링 파마 악티엔게젤샤프트 | 양성 호르몬 의존성 부인과 질병의 치료 및 예방을 위한메조프로게스틴 (프로게스테론 수용체 조절물질) |
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 |
DE19961219A1 (de) * | 1999-12-15 | 2001-07-19 | Jenapharm Gmbh | 11beta-Phenylestratrien-Derivate mit Fluoralkylgruppen in der aromatischen Seitenkette, deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
EP1157996A1 (de) * | 2000-05-23 | 2001-11-28 | JENAPHARM GmbH | Neue Festkörperformen des Mesoprogestins 11Beta-[4E-(Hydroxyiminomethyl)-phenyl]-17Alpha-methoxymethyl-17Beta-methoxy-estra-4,9-dien-3-on |
JP4593754B2 (ja) * | 2000-10-13 | 2010-12-08 | 一般財団法人 化学物質評価研究機構 | 化学物質の50%阻害濃度決定方法 |
DE10056675A1 (de) | 2000-11-10 | 2002-05-16 | Jenapharm Gmbh | Verfahren zur Herstellung von 4-(17alpha-Methylsubstituierten 3-Oxoestra-4,9-dien-11ß-yl)-benzaldehyd-(1E oder 1Z)-oximen |
DE10056676A1 (de) * | 2000-11-10 | 2002-05-16 | Jenapharm Gmbh | Verfahren zur Herstellung von 4-/17alpha-substituierten-3-oxoestra-4,9-dien-11beta-yl)benzaldehyd-(1E oder 1Z)-oximen |
EP1285927A3 (de) * | 2001-08-16 | 2005-06-29 | Schering Aktiengesellschaft | Verwendung von Glucocorticoid-Rezeptorantagonisten zur Vorbeugung und Behandlung von Erkrankungen des männlichen Reproduktionssystems |
DE10218109A1 (de) * | 2002-04-23 | 2003-11-20 | Jenapharm Gmbh | Verfahren zum Herstellen von Kristallen, danach erhältliche Kristalle und deren Verwendung in pharmazeutischen Formulierungen |
DE10218107A1 (de) * | 2002-04-23 | 2003-11-20 | Jenapharm Gmbh | Verfahren zum Herstellen von Kristallen von Steroiden, danach erhältliche Kristalle und deren Verwendung in pharmazeutischen Formulierungen |
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 |
EP1525215B1 (de) * | 2002-08-02 | 2006-09-06 | Schering Aktiengesellschaft | Progesteronrezeptormodulatoren mit erhöhter antigonadotroper aktivität für die weibliche fertilitätskontrolle und hormonersatztherapie |
US20050215536A1 (en) * | 2004-03-24 | 2005-09-29 | Kristof Chwalisz | Sequential SPRM/ progestin treatment |
US20050215535A1 (en) * | 2004-03-24 | 2005-09-29 | Kristof Chwalisz | Sequential SPRM/progestin treatment |
DE102005059222B4 (de) * | 2005-12-08 | 2007-10-11 | Bayer Schering Pharma Ag | 11ß-Benzaldoximderivate von D-Homoestra-4,9-dien-3-onen |
DE102006018888A1 (de) * | 2006-04-18 | 2007-10-25 | Bayer Schering Pharma Ag | Verfahren zur Herstellung von 4-[17beta-Methoxy-17alpha-methoxymethyl-3-oxoestra-4,9-dien-11beta-yl]benzaldehyd-(E)-oxims (Asoprisnil) |
SI3263112T1 (sl) | 2006-10-24 | 2020-10-30 | Allergan Pharmaceuticals International Limited | Sestavki in metode za zaviranje endometrijskih proliferacij |
DE102006054535A1 (de) * | 2006-11-15 | 2008-05-21 | Bayer Schering Pharma Aktiengesellschaft | Progesteronrezeptorantagonisten |
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 |
DE102009034368A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-acyloxyalkylenphenyl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
DE102009034366A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-methylenoxyalkylenaryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
DE102009034367A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-benzyliden-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Behandlung von Krankheiten |
DE102009034526A1 (de) | 2009-07-21 | 2011-02-10 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-ethinylphenyl-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Behandlung von Krankheiten |
DE102010007722A1 (de) | 2010-02-10 | 2011-08-11 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Progesteronrezeptorantagonisten |
DE102010007719A1 (de) | 2010-02-10 | 2011-08-11 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Progesteronrezeptorantagonisten |
KR102166867B1 (ko) | 2010-03-22 | 2020-10-19 | 앨러간 파마슈티컬스 인터내셔널 리미티드 | 항프로게스틴의 비독성 전달을 위한 조성물들과 그 방법들 |
CN113559075A (zh) | 2014-11-17 | 2021-10-29 | 康泰科思特生物制药公司 | 奥那司酮延长释放组合物和方法 |
BR112018005999A2 (pt) | 2015-09-25 | 2019-01-08 | Context Biopharma Inc | métodos para a produção de intermediários de onapristona |
MX2018007154A (es) | 2015-12-15 | 2019-01-10 | Context Biopharma Inc | Composiciones de onapristona amorfa y metodos para hacer las mismas. |
US20180148471A1 (en) | 2016-11-30 | 2018-05-31 | Arno Therapeutics, Inc. | Methods for onapristone synthesis dehydration and deprotection |
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AU580843B2 (en) * | 1985-02-07 | 1989-02-02 | Schering Aktiengesellschaft | 11``-phenyl-gonanes, their manufacture and pharmaceutical preparations containing them |
DE3506785A1 (de) * | 1985-02-22 | 1986-08-28 | Schering AG, Berlin und Bergkamen, 1000 Berlin | 11ss-n,n-dimethylaminophenyl-estradiene, deren herstellung und diese enthaltende pharmazeutische praeparate |
FR2598421B1 (fr) * | 1986-05-06 | 1988-08-19 | Roussel Uclaf | Nouveaux produits 19-nor ou 19-nor d-homo steroides substitues en position 11b par un radical phenyle portant un radical alkynyle, leur procede de preparation, leur application comme medicaments et les compositions les renfermant |
US5272140A (en) * | 1987-01-23 | 1993-12-21 | Akzo N.V. | 11-aryl steroid derivatives |
ATE69820T1 (de) * | 1987-04-24 | 1991-12-15 | Akzo Nv | 11-arylestranderivate und 11-arylpregnanderivate. |
DD287510A5 (de) * | 1989-04-19 | 1991-02-28 | Adw,Zi Fuer Mikrobiologie Und Experimentelle Therapie,De | Verfahren zur herstellung von 17 alpha-ch tief 2x-substituierten 11 beta-aryl-4,9-diensteroiden |
EP0411733B1 (de) * | 1989-08-04 | 1998-10-21 | Schering Aktiengesellschaft | 11 Beta-Aryl-gona-4,9-dien-3-one |
US5276023A (en) * | 1989-08-08 | 1994-01-04 | Roussel Uclaf | 19-nor-steroid esters |
DD289539A5 (de) * | 1989-10-12 | 1991-05-02 | Zi F. Mikrobiologie U. Experimentelle Therapie,De | Verfahren zur herstellung von 11 beta-(4-acetylphenyl)-17alpha-alkoxy-methyl-estra-4,9-dien-3-onen |
US5407928A (en) * | 1990-08-15 | 1995-04-18 | Schering Aktiengesellschaft | 11β-aryl-gona-4,9-dien-3-ones |
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 |
DE4332283A1 (de) * | 1993-09-20 | 1995-04-13 | Jenapharm Gmbh | Neue 11-Benzaldoximestradien-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 |
-
1993
- 1993-09-20 DE DE4332283A patent/DE4332283A1/de not_active Withdrawn
-
1994
- 1994-07-07 DK DK94250178.4T patent/DK0648778T3/da active
- 1994-07-07 AT AT94250178T patent/ATE156835T1/de not_active IP Right Cessation
- 1994-07-07 DE DE59403717T patent/DE59403717D1/de not_active Expired - Fee Related
- 1994-07-07 EP EP94250178A patent/EP0648778B1/de not_active Expired - Lifetime
- 1994-07-07 ES ES94250178T patent/ES2108371T3/es not_active Expired - Lifetime
- 1994-08-09 NO NO942953A patent/NO304989B1/no not_active IP Right Cessation
- 1994-08-09 FI FI943687A patent/FI113657B/sv active
- 1994-08-10 SK SK957-94A patent/SK280137B6/sk not_active IP Right Cessation
- 1994-08-12 NZ NZ264229A patent/NZ264229A/en not_active IP Right Cessation
- 1994-08-15 CZ CZ19941970A patent/CZ292298B6/cs not_active IP Right Cessation
- 1994-08-18 AU AU70350/94A patent/AU682195B2/en not_active Ceased
- 1994-08-19 CA CA002130516A patent/CA2130516C/en not_active Expired - Lifetime
- 1994-09-19 HU HU9402694A patent/HU223339B1/hu not_active IP Right Cessation
- 1994-09-19 PL PL94305092A patent/PL183181B1/pl not_active IP Right Cessation
- 1994-09-20 US US08/309,175 patent/US5693628A/en not_active Expired - Lifetime
- 1994-09-20 JP JP6224379A patent/JP2753562B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2753562B2 (ja) | 1998-05-20 |
NO942953D0 (no) | 1994-08-09 |
HU9402694D0 (en) | 1994-11-28 |
FI943687A0 (sv) | 1994-08-09 |
EP0648778A3 (de) | 1995-08-09 |
AU682195B2 (en) | 1997-09-25 |
SK280137B6 (sk) | 1999-08-06 |
PL305092A1 (en) | 1995-04-03 |
CZ292298B6 (cs) | 2003-09-17 |
SK95794A3 (en) | 1995-04-12 |
NO304989B1 (no) | 1999-03-15 |
NO942953L (no) | 1995-03-21 |
US5693628A (en) | 1997-12-02 |
PL183181B1 (pl) | 2002-06-28 |
DE4332283A1 (de) | 1995-04-13 |
DK0648778T3 (da) | 1998-03-30 |
EP0648778A2 (de) | 1995-04-19 |
NZ264229A (en) | 1995-04-27 |
CZ197094A3 (en) | 1995-04-12 |
CA2130516A1 (en) | 1995-03-21 |
DE59403717D1 (de) | 1997-09-18 |
AU7035094A (en) | 1995-03-30 |
ATE156835T1 (de) | 1997-08-15 |
CA2130516C (en) | 2003-04-15 |
FI943687A (sv) | 1995-03-21 |
JPH07149789A (ja) | 1995-06-13 |
HUT68029A (en) | 1995-05-29 |
ES2108371T3 (es) | 1997-12-16 |
HU223339B1 (hu) | 2004-06-28 |
EP0648778B1 (de) | 1997-08-13 |
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