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WO1988002753A3 - Steroides 9-alpha-hydroxy et procede de preparation desdits steroides - Google Patents

Steroides 9-alpha-hydroxy et procede de preparation desdits steroides Download PDF

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Publication number
WO1988002753A3
WO1988002753A3 PCT/NL1987/000026 NL8700026W WO8802753A3 WO 1988002753 A3 WO1988002753 A3 WO 1988002753A3 NL 8700026 W NL8700026 W NL 8700026W WO 8802753 A3 WO8802753 A3 WO 8802753A3
Authority
WO
WIPO (PCT)
Prior art keywords
alpha
preparation
hydroxy steroids
hydroxy
steroids
Prior art date
Application number
PCT/NL1987/000026
Other languages
English (en)
Other versions
WO1988002753A2 (fr
Inventor
Jacobus Nicolaas Maria Batist
Arthur Friedrich Marx
Zoest Willem Johan Van
Jagdish Chander Kapur
Original Assignee
Gist Brocades Nv
Jacobus Nicolaas Maria Batist
Arthur Friedrich Marx
Zoest Willem Johan Van
Jagdish Chander Kapur
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 Gist Brocades Nv, Jacobus Nicolaas Maria Batist, Arthur Friedrich Marx, Zoest Willem Johan Van, Jagdish Chander Kapur filed Critical Gist Brocades Nv
Priority to US07/412,557 priority Critical patent/US5352809A/en
Priority to JP62506679A priority patent/JPH0826062B2/ja
Priority to KR1019880700547A priority patent/KR960010793B1/ko
Priority to HU875312A priority patent/HU204063B/hu
Publication of WO1988002753A2 publication Critical patent/WO1988002753A2/fr
Priority to NO882075A priority patent/NO174748C/no
Priority to FI882461A priority patent/FI95710C/fi
Priority to DK198803131A priority patent/DK175438B1/da
Publication of WO1988002753A3 publication Critical patent/WO1988002753A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/28—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0014—Androstane derivatives substituted in position 17 alfa, not substituted in position 17 beta
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
    • C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
    • C07J1/0048—Alkynyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/005—Normal 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)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J21/005—Ketals
    • C07J21/006—Ketals at position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • 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
    • C07J41/0038—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide group
    • 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
    • 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
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal 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
    • C07J5/0046—Normal 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
    • C07J5/0053—Normal 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal 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
    • C07J7/004—Normal 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 substituted in position 17 alfa
    • C07J7/0045—Normal 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 substituted in position 17 alfa not substituted in position 16
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal 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
    • C07J7/004—Normal 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 substituted in position 17 alfa
    • C07J7/005—Normal 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 substituted in position 17 alfa substituted in position 16
    • C07J7/0055—Normal 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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
    • C07J7/0085—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by an halogen atom

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Steroid Compounds (AREA)

Abstract

De nouveaux stéroïdes 9-alpha-hydroxy sont préparés par introduction de substituants dans l'anneau D d'un 9-alpha-hydroxy-androst-4-ène-3,17-dione. Les composés qui en résultent constituent des intermédiaires utiles dans la synthèse de corticostéroïdes.
PCT/NL1987/000026 1986-10-10 1987-10-09 Steroides 9-alpha-hydroxy et procede de preparation desdits steroides WO1988002753A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US07/412,557 US5352809A (en) 1986-10-10 1987-10-09 9-alpha-hydroxy steroids, process for their preparation, process for the preparation of the corresponding 9(11)-dehydro derivatives and pharmaceutical preparations containing such steroids
JP62506679A JPH0826062B2 (ja) 1986-10-10 1987-10-09 ９―α―ヒドロキシステロイド及びその製法
KR1019880700547A KR960010793B1 (ko) 1986-10-10 1987-10-09 9-알파-히드록시 스테로이드 및 그의 제조방법
HU875312A HU204063B (en) 1986-10-10 1987-10-09 Process for producing 9-alpha-hydroxy steroids
NO882075A NO174748C (no) 1986-10-10 1988-05-11 9- av farmakologisk aktive pregnaner
FI882461A FI95710C (fi) 1986-10-10 1988-05-25 9-alfa-hydroksi-steroidit, menetelmä niiden valmistamiseksi ja menetelmä vastaavien 9(11)-dehydro-johdannaisten valmistamiseksi
DK198803131A DK175438B1 (da) 1986-10-10 1988-06-09 9-alfa-hydroxy-steroider, fremgangsmåde til deres fremstilling og fremgangsmåde til fremstillingen af de tilsvarende 9(11)-dehydro-derivater

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
NL86201754.8(EP) 1986-10-10
EP86201754 1986-10-10
EP87201340 1987-07-13
NL87201340.4(EP) 1987-07-13

Publications (2)

Publication Number Publication Date
WO1988002753A2 WO1988002753A2 (fr) 1988-04-21
WO1988002753A3 true WO1988002753A3 (fr) 1988-06-30

Family

ID=26103306

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL1987/000026 WO1988002753A2 (fr) 1986-10-10 1987-10-09 Steroides 9-alpha-hydroxy et procede de preparation desdits steroides

Country Status (19)

Country Link
US (2) US5352809A (fr)
EP (1) EP0263569B1 (fr)
JP (1) JPH0826062B2 (fr)
KR (1) KR960010793B1 (fr)
CN (2) CN1035182C (fr)
AU (1) AU607948B2 (fr)
CA (1) CA1334844C (fr)
DE (1) DE3783007T2 (fr)
DK (1) DK175438B1 (fr)
ES (1) ES2052550T3 (fr)
FI (1) FI95710C (fr)
GR (1) GR3006576T3 (fr)
HU (2) HU204063B (fr)
IE (1) IE61985B1 (fr)
IL (1) IL84135A (fr)
NO (1) NO174748C (fr)
NZ (1) NZ222103A (fr)
PT (1) PT85891B (fr)
WO (1) WO1988002753A2 (fr)

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US4921638A (en) * 1986-11-05 1990-05-01 The Upjohn Company 17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one
EP0322081B1 (fr) * 1987-12-23 1992-12-16 Roussel-Uclaf Procédé de préparation microbiologique de 9-alpha-hydroxy-17-céto-stéroides
US5298398A (en) * 1987-12-23 1994-03-29 Gist-Brocades Nv Preparation of 9-α-hydroxy-17-keto steroids using Mycobacterium species CBS 482.86
US5372996A (en) * 1989-03-10 1994-12-13 Endorecherche, Inc. Method of treatment of androgen-related diseases
US5364847A (en) * 1989-03-10 1994-11-15 Endorecherche Inhibitors of sex steroid biosynthesis and methods for their production and use
ATE170753T1 (de) * 1989-07-07 1998-09-15 Endorecherche Inc Androgenderivate zur hemming der aktivität der sexualsteroide
ES2189784T3 (es) * 1989-07-07 2003-07-16 Endorech Inc Procedimiento para el tratamiento de enfermedades relacionadas con adrogenos.
ZA909444B (en) * 1989-11-27 1991-08-28 Schering Corp Process for dehydrating corticosteroid intermediates
EP0523132A1 (fr) * 1990-03-27 1993-01-20 Schering Corporation PROCEDE DE DESHYDRATATION DE 9$g(a)-HYDROXY STEROIDES
US5252319A (en) * 1990-06-12 1993-10-12 Insite Vision Incorporated Aminosteroids for ophthalmic use
US5209926A (en) * 1990-06-12 1993-05-11 Insite Vision Incorporated Aminosteroids for ophthalmic use
US5124154A (en) * 1990-06-12 1992-06-23 Insite Vision Incorporated Aminosteroids for ophthalmic use
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US5502183A (en) * 1992-01-28 1996-03-26 Schering Corporation Steroid intermediates and processes for their preparation
KR950701527A (ko) * 1992-05-21 1995-04-28 라브리 페르낭 테스토스테론 5α 환원효소 활성 저해제(INHIBITORS OF TESTOSTERONE 5α-REDUCTASE ACTIVITY)
FR2692580B1 (fr) * 1992-06-19 1994-08-26 Roussel Uclaf Nouveau Procédé de préparation d'un composé stéroïde DELTA9 (11).
CN1147816A (zh) * 1994-05-09 1997-04-16 法玛西雅厄普约翰公司 17β-氰基-3-乙氧基-17α-羟基-6-甲基雄甾-3，5，9(11)-三烯的合成
FR2720747B1 (fr) * 1994-06-02 1996-07-12 Roussel Uclaf Nouveau procédé de préparation d'un stéroïde 16béta-méthyl et nouveaux intermédiaires.
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JP2005523306A (ja) * 2002-03-22 2005-08-04 ファルマシア・アンド・アップジョン・カンパニー・エルエルシー エプレレノンの製法
PT1889198E (pt) 2005-04-28 2015-03-06 Proteus Digital Health Inc Sistema fármaco-informático
EP1945240B1 (fr) 2005-09-16 2016-12-28 Raptor Pharmaceutical Inc Compositions de proteines rap specifiques des proteines contenant du cr, et leurs utilisations
DE102007027635A1 (de) * 2007-06-12 2008-12-18 Bayer Schering Pharma Aktiengesellschaft 17ß-Cyano-19-androst-4-en-Derivat, dessen Verwendung und das Derivat enthaltende Arzneimittel
DK3395372T3 (da) 2009-02-20 2022-04-19 Enhanx Biopharm Inc System til afgivelse af glutathion-baseret medikament
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CN102516345B (zh) * 2011-11-01 2014-11-26 上海优拓医药科技有限公司 醋酸乌利司他及其关键中间体的制备方法
CN107955052B (zh) * 2011-12-23 2024-07-05 晶体制药独资有限公司 炔基化16-取代-17-酮基类固醇的方法
CN105073119A (zh) * 2013-01-23 2015-11-18 司菲埃拉制药私人有限公司 用于线粒体生物发生和与线粒体功能障碍或耗竭相关的疾病的新颖11β-羟基类固醇化合物
CN103361394B (zh) * 2013-08-07 2016-08-17 中国科学院上海高等研究院 利用微生物转化制备9α-羟基-雄烯二酮的方法
CN106714770B (zh) 2014-07-23 2024-04-19 斯法尔制药私人有限公司 羟基类固醇化合物、其中间体、制备方法、组合物及其用途
CN105440094B (zh) * 2015-11-27 2017-08-25 江苏佳尔科药业集团有限公司 地塞米松中间体的制备方法
CN109369759A (zh) * 2018-11-22 2019-02-22 湖南原野医药有限公司 氢化可的松中间体17β-氰基甾体化合物的合成方法
CN109734762B (zh) * 2018-12-05 2020-04-17 郑良彬 一锅法合成16-β甲基甾体化合物的方法
CN111320665A (zh) * 2020-03-04 2020-06-23 台州仙琚药业有限公司 制备17β-氰基-17α-羟基-9-去氢雄烯二酮的方法
CN113817016A (zh) * 2020-06-18 2021-12-21 天津天药药业股份有限公司 3位胺基保护的雄甾16ɑ-甲基的制备方法
CN113817011A (zh) * 2020-06-18 2021-12-21 天津天药药业股份有限公司 3位烯醇醚或酯保护的雄甾16ɑ-甲基的制备方法
CN113817015A (zh) * 2020-06-18 2021-12-21 天津天药药业股份有限公司 3位二醇保护的雄甾16ɑ-甲基的制备方法

Citations (5)

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Publication number Priority date Publication date Assignee Title
US4035236A (en) * 1975-10-24 1977-07-12 The Upjohn Company Process for preparing 9α-hydroxyandrostenedione
US4102907A (en) * 1977-03-07 1978-07-25 The Upjohn Company Desulfinylation process for preparing androsta-4,9(11)-diene-3,17-dione
GB2102805A (en) * 1981-07-24 1983-02-09 Upjohn Co Synthesis of 6-fluoro steroids
US4397947A (en) * 1981-06-12 1983-08-09 G. D. Searle & Co. Microbial process for 9α-hydroxylation of steroids
EP0153001A2 (fr) * 1984-02-03 1985-08-28 The Upjohn Company Stéroides porteurs d'un groupe énamide ou énimide et leur préparation

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CA565369A (fr) * 1958-10-28 P. Graber Robert Steroides 9,11-dihydroxy et procedes pour leur preparation
US2837545A (en) * 1957-04-29 1958-06-03 American Cyanamid Co 9alpha, 11beta, 16alpha, 17alpha, 21-penta-hydroxy-4-pregnene-3, 20 dione, its 16, 21 diesters and process of preparing the above compounds
US2840580A (en) * 1957-05-24 1958-06-24 Olin Mathieson 9alpha-hydroxy steroids
US4416821A (en) * 1982-02-17 1983-11-22 The Upjohn Company Process for preparing 16-methylene steroids
US4618456A (en) * 1984-03-20 1986-10-21 The Upjohn Company Ethynylation of 16-methyl-17-keto steroids
US4705783A (en) * 1985-06-25 1987-11-10 Sri International 9α, 11β-substituted and 11β-substituted estranes
US5352809A (en) * 1986-10-10 1994-10-04 Gist-Brocades N.V. 9-alpha-hydroxy steroids, process for their preparation, process for the preparation of the corresponding 9(11)-dehydro derivatives and pharmaceutical preparations containing such steroids
US4921638A (en) * 1986-11-05 1990-05-01 The Upjohn Company 17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4035236A (en) * 1975-10-24 1977-07-12 The Upjohn Company Process for preparing 9α-hydroxyandrostenedione
US4102907A (en) * 1977-03-07 1978-07-25 The Upjohn Company Desulfinylation process for preparing androsta-4,9(11)-diene-3,17-dione
US4397947A (en) * 1981-06-12 1983-08-09 G. D. Searle & Co. Microbial process for 9α-hydroxylation of steroids
GB2102805A (en) * 1981-07-24 1983-02-09 Upjohn Co Synthesis of 6-fluoro steroids
EP0153001A2 (fr) * 1984-02-03 1985-08-28 The Upjohn Company Stéroides porteurs d'un groupe énamide ou énimide et leur préparation

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DE3783007T2 (de) 1993-07-01
CN1116208A (zh) 1996-02-07
JPH0826062B2 (ja) 1996-03-13
GR3006576T3 (fr) 1993-06-30
DK313188D0 (da) 1988-06-09
EP0263569A2 (fr) 1988-04-13
IE872722L (en) 1992-04-16
FI95710B (fi) 1995-11-30
HUT47130A (en) 1989-01-30
ES2052550T3 (es) 1994-07-16
DK313188A (da) 1988-06-09
IL84135A (en) 1992-08-18
US5352809A (en) 1994-10-04
IL84135A0 (en) 1988-03-31
KR960010793B1 (ko) 1996-08-08
DK175438B1 (da) 2004-10-18
PT85891B (pt) 1990-07-31
FI882461L (fi) 1988-05-25
PT85891A (en) 1987-11-01
EP0263569A3 (en) 1988-07-20
CN87106868A (zh) 1988-04-27
US5565588A (en) 1996-10-15
AU607948B2 (en) 1991-03-21
NO882075D0 (no) 1988-05-11
NO174748C (no) 1994-06-29
KR890700129A (ko) 1989-03-02
AU8106887A (en) 1988-05-06
HUT61568A (en) 1993-01-28
HU204063B (en) 1991-11-28
DE3783007D1 (de) 1993-01-21
NO882075L (no) 1988-05-11
FI95710C (fi) 1996-03-11
FI882461A0 (fi) 1988-05-25
EP0263569B1 (fr) 1992-12-09
NZ222103A (en) 1990-08-28
CN1036342C (zh) 1997-11-05
IE61985B1 (en) 1994-12-14
CN1035182C (zh) 1997-06-18
CA1334844C (fr) 1995-03-21
HU912420D0 (en) 1991-12-30
JPH01500907A (ja) 1989-03-30
NO174748B (no) 1994-03-21
WO1988002753A2 (fr) 1988-04-21
HU211080B (en) 1995-10-30

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