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FI934861L - Foerfarande foer framstaellning av 3a-hydroxi, 3b-substituerade pregnaner - Google Patents

Foerfarande foer framstaellning av 3a-hydroxi, 3b-substituerade pregnaner Download PDF

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Publication number
FI934861L
FI934861L FI934861A FI934861A FI934861L FI 934861 L FI934861 L FI 934861L FI 934861 A FI934861 A FI 934861A FI 934861 A FI934861 A FI 934861A FI 934861 L FI934861 L FI 934861L
Authority
FI
Finland
Prior art keywords
pregnaner
substituerade
hydroxi
foerfarande foer
foer framstaellning
Prior art date
Application number
FI934861A
Other languages
English (en)
Other versions
FI111843B (fi
FI934861A0 (fi
Inventor
Syed Hasan Tahir
Michael Bruce Bolger
Richard Buswell
Richard Gabriel
Jay Stearns
Original Assignee
Cocensys Inc
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.)
Filing date
Publication date
Application filed by Cocensys Inc filed Critical Cocensys Inc
Publication of FI934861L publication Critical patent/FI934861L/fi
Publication of FI934861A0 publication Critical patent/FI934861A0/fi
Application granted granted Critical
Publication of FI111843B publication Critical patent/FI111843B/fi

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/568Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/58Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J1/00Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003Androstane derivatives
    • C07J1/0018Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C07J1/0022Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J13/00Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/005Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J13/00Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/007Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J21/00Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J21/00Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J21/005Ketals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J3/00Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
    • C07J3/005Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J41/00Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/005Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J43/00Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J5/00Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C07J5/0007Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond not substituted in position 17 alfa
    • C07J5/0015Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond not substituted in position 17 alfa not substituted in position 16
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J5/00Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C07J5/0046Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
    • C07J5/0053Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa not substituted in position 16
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J51/00Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J7/00Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/0015Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
    • C07J7/002Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J7/00Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/0065Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J71/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005Oxygen-containing hetero ring
    • C07J71/001Oxiranes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J9/00Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Diaphragms For Electromechanical Transducers (AREA)
  • External Artificial Organs (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Detergent Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
FI934861A 1992-03-04 1993-11-03 Menetelmä 3alfa-hydroksi-3beta-substituoitujen pregnaanien valmistamiseksi FI111843B (fi)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US07/846,193 US5319115A (en) 1987-08-25 1992-03-04 Method for making 3α-hydroxy, 3β-substituted-pregnanes
US84619392 1992-03-04
US9301602 1993-02-22
PCT/US1993/001602 WO1993018053A1 (en) 1992-03-04 1993-02-22 METHOD FOR MAKING 3α-HYDROXY,3β-SUBSTITUTED-PREGNANES

Publications (3)

Publication Number Publication Date
FI934861L true FI934861L (fi) 1993-11-03
FI934861A0 FI934861A0 (fi) 1993-11-03
FI111843B FI111843B (fi) 2003-09-30

Family

ID=25297208

Family Applications (1)

Application Number Title Priority Date Filing Date
FI934861A FI111843B (fi) 1992-03-04 1993-11-03 Menetelmä 3alfa-hydroksi-3beta-substituoitujen pregnaanien valmistamiseksi

Country Status (14)

Country Link
US (1) US5319115A (fi)
EP (1) EP0589034B1 (fi)
JP (2) JP3983796B2 (fi)
KR (1) KR100257031B1 (fi)
AT (1) ATE179715T1 (fi)
AU (1) AU668926B2 (fi)
CA (1) CA2102400C (fi)
DE (1) DE69324752T2 (fi)
DK (1) DK0589034T3 (fi)
ES (1) ES2132249T3 (fi)
FI (1) FI111843B (fi)
GR (1) GR3030660T3 (fi)
NO (1) NO305604B1 (fi)
WO (1) WO1993018053A1 (fi)

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US5232917A (en) * 1987-08-25 1993-08-03 University Of Southern California Methods, compositions, and compounds for allosteric modulation of the GABA receptor by members of the androstane and pregnane series
US5939545A (en) 1994-02-14 1999-08-17 Cocensys, Inc. Method, compositions, and compounds for allosteric modulation of the gaba receptor by members of the androstane and pregnane series
EP0837874B1 (en) * 1995-06-06 2004-12-15 Euro-Celtique S.A. Neuroactive steroids of the androstane and pregnane series
US6780853B1 (en) 1995-06-06 2004-08-24 Euro-Celtique S.A. Neuroactive steroids of the androstane and pregnane series
EP1177206A1 (en) * 1999-04-29 2002-02-06 Purdue Pharma Ltd. 3alpha-hydroxy-3beta methoxymethyl-21-heterocycle substituted steroids with anaesthetic activity
EP1928437A2 (en) 2005-08-26 2008-06-11 Braincells, Inc. Neurogenesis by muscarinic receptor modulation
EP2258359A3 (en) 2005-08-26 2011-04-06 Braincells, Inc. Neurogenesis by muscarinic receptor modulation with sabcomelin
JP2009512711A (ja) 2005-10-21 2009-03-26 ブレインセルス,インコーポレイティド Pde阻害による神経新生の調節
WO2007053596A1 (en) 2005-10-31 2007-05-10 Braincells, Inc. Gaba receptor mediated modulation of neurogenesis
US20100216734A1 (en) 2006-03-08 2010-08-26 Braincells, Inc. Modulation of neurogenesis by nootropic agents
WO2007134136A2 (en) 2006-05-09 2007-11-22 Braincells, Inc. Neurogenesis by modulating angiotensin
US20100184806A1 (en) 2006-09-19 2010-07-22 Braincells, Inc. Modulation of neurogenesis by ppar agents
WO2010099217A1 (en) 2009-02-25 2010-09-02 Braincells, Inc. Modulation of neurogenesis using d-cycloserine combinations
ES2524724T3 (es) 2009-08-13 2014-12-11 Marinus Pharmaceuticals, Inc. Método para preparar 3alfa-hidroxi,3beta-metil-5alfa-pregnán-20-ona (ganaxolona)
EP2766380B1 (en) 2011-10-14 2019-04-24 Sage Therapeutics, Inc. 3,3 disubstituted 19-nor pregnane compounds, compositions, and uses thereof
RS59734B1 (sr) 2012-01-23 2020-02-28 Sage Therapeutics Inc Formulacije neuroaktivnog steroida koje uključuju kompleks alopregnanolona i sulfobutil etar beta-ciklodekstrina
MX2015002252A (es) 2012-08-21 2015-07-21 Sage Therapeutics Inc Metodos para tratar epilepsia o estado de epilepsia.
JP2016501876A (ja) 2012-11-30 2016-01-21 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア ステロイドの抗痙攣活性
MX362543B (es) 2013-04-17 2019-01-24 Sage Therapeutics Inc Esteroides c21-n-pirazolilo 19-nor c3,3- disustituidos y metodos de uso de los mismos.
WO2014169836A1 (en) 2013-04-17 2014-10-23 Sage Therapeutics, Inc. 19-nor neuroactive steroids and methods of use thereof
WO2014169831A1 (en) 2013-04-17 2014-10-23 Sage Therapeutics, Inc. 19-nor c3,3-disubstituted c21-c-bound heteroaryl steroids and methods of use thereof
RU2019126333A (ru) 2013-04-17 2019-10-08 Сейдж Терапьютикс, Инк. 19-нор нейроактивные стероиды и способы их применения
SI3021852T1 (sl) 2013-07-19 2021-07-30 Sage Therapeutics, Inc. Nevroaktivni steroidi, sestavki in uporabe le-teh
CN105579043B (zh) 2013-08-23 2021-09-14 萨奇治疗股份有限公司 神经活性类固醇、组合物和其用途
US9629853B2 (en) 2014-05-21 2017-04-25 Wisconsin Alumni Research Foundation Uses of ganaxolone
US10246482B2 (en) 2014-06-18 2019-04-02 Sage Therapeutics, Inc. Neuroactive steroids, compositions, and uses thereof
MA40498A (fr) 2014-09-02 2021-05-19 Texas A & M Univ Sys Méthode de traitement de l'intoxication par organophosphates
JOP20200195A1 (ar) 2014-09-08 2017-06-16 Sage Therapeutics Inc سترويدات وتركيبات نشطة عصبياً، واستخداماتها
TW202426002A (zh) 2014-10-16 2024-07-01 美商賽吉醫療公司 用於治療中樞神經系統(cns)病症之組合物及方法
RS60642B1 (sr) 2014-10-16 2020-09-30 Sage Therapeutics Inc Kompozicije i postupci za lečenje poremećaja cns-a
EP3719029A1 (en) 2014-11-27 2020-10-07 Sage Therapeutics, Inc. Compositions for inducing sedation
DK3250210T3 (da) 2015-01-26 2021-03-08 Sage Therapeutics Inc Sammensætninger og fremgangsmåder til behandling af cns-forstyrrelser
ES2935476T3 (es) 2015-02-20 2023-03-07 Sage Therapeutics Inc Esteroides neuroactivos, composiciones y usos de los mismos
RU2766155C2 (ru) 2016-03-08 2022-02-08 Сейдж Терапьютикс, Инк. Нейроактивные стероиды, их композиции и применения
EP3481844B1 (en) 2016-07-11 2024-04-17 Sage Therapeutics, Inc. C7, c12, and c16 substituted neuroactive steroids and their methods of use
CN116162121A (zh) 2016-07-11 2023-05-26 萨奇治疗股份有限公司 C17、c20和c21取代的神经活性类固醇及其使用方法
PH12021553005A1 (en) 2019-05-31 2023-08-14 Sage Therapeutics Inc Neuroactive steroids and compositions thereof
WO2023060067A1 (en) 2021-10-04 2023-04-13 Marinus Pharmaceuticals, Inc. Amorphous solid dispersion ganaxolone formulation

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US3466276A (en) * 1967-09-05 1969-09-09 Upjohn Co 2-piperidylglycol ketals of steroidal compounds
US3697509A (en) * 1970-04-13 1972-10-10 Searle & Co N-(3-oxopregna-4, 17(20)-dien-21-yl) quaternary salts and }9-nor derivatives corresponding
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DE2237143A1 (de) * 1972-07-28 1974-02-14 Hoechst Ag Verfahren zur herstellung von beta(3-keto-7alpha-acetylthio-17beta-hydroxy4-androsten-17alpha-yl)-propionsaeuregamma-lacton und dessen 1-dehydro-derivat
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US5120723A (en) * 1987-08-25 1992-06-09 University Of Southern California Method, compositions, and compounds for modulating brain excitability
US5232917A (en) * 1987-08-25 1993-08-03 University Of Southern California Methods, compositions, and compounds for allosteric modulation of the GABA receptor by members of the androstane and pregnane series
FR2644788B1 (fr) * 1989-03-22 1995-02-03 Roussel Uclaf Nouveaux steroides 3-ceto comportant une chaine en 17 amino-substituee, leur procede de preparation et les intermediaires de ce procede, leur application comme medicaments et les compositions pharmaceutiques les contenant

Also Published As

Publication number Publication date
ATE179715T1 (de) 1999-05-15
JP2006151994A (ja) 2006-06-15
FI111843B (fi) 2003-09-30
JPH06507427A (ja) 1994-08-25
JP3983796B2 (ja) 2007-09-26
EP0589034A1 (en) 1994-03-30
EP0589034A4 (en) 1996-05-22
NO305604B1 (no) 1999-06-28
WO1993018053A1 (en) 1993-09-16
EP0589034B1 (en) 1999-05-06
DK0589034T3 (da) 1999-11-01
US5319115A (en) 1994-06-07
ES2132249T3 (es) 1999-08-16
DE69324752T2 (de) 1999-09-09
DE69324752D1 (de) 1999-06-10
CA2102400A1 (en) 1993-09-05
NO933972D0 (no) 1993-11-03
AU668926B2 (en) 1996-05-23
FI934861A0 (fi) 1993-11-03
GR3030660T3 (en) 1999-10-29
NO933972L (no) 1993-11-03
CA2102400C (en) 2004-08-10
AU3775893A (en) 1993-10-05
KR100257031B1 (ko) 2000-08-01

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