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NO882075D0 - 9-alfa-hydroksysteroider, deres fremstilling, en fremgangsmaate for fremstilling av de tilsvarende 9(11)-dehydro-derivater samt farmasoeytiske preparater inneholdend - Google Patents

9-alfa-hydroksysteroider, deres fremstilling, en fremgangsmaate for fremstilling av de tilsvarende 9(11)-dehydro-derivater samt farmasoeytiske preparater inneholdend

Info

Publication number
NO882075D0
NO882075D0 NO1988882075A NO882075A NO882075D0 NO 882075 D0 NO882075 D0 NO 882075D0 NO 1988882075 A NO1988882075 A NO 1988882075A NO 882075 A NO882075 A NO 882075A NO 882075 D0 NO882075 D0 NO 882075D0
Authority
NO
Norway
Prior art keywords
preparation
hydroxysteroids
dehydro
alfa
derivatives
Prior art date
Application number
NO1988882075A
Other languages
English (en)
Other versions
NO174748C (no
NO882075L (no
NO174748B (no
Inventor
Jacobus Nicolaas Maria Batist
Arthur Friedrich Marx
Willem Johan Van Zoest
Jagdish Chander Kapur
Original Assignee
Gist Brocades Nv
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 filed Critical Gist Brocades Nv
Publication of NO882075L publication Critical patent/NO882075L/no
Publication of NO882075D0 publication Critical patent/NO882075D0/no
Publication of NO174748B publication Critical patent/NO174748B/no
Publication of NO174748C publication Critical patent/NO174748C/no

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24Benzimidazoles; 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
    • C07D235/28Sulfur atoms
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/12Heterocyclic 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
    • 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
    • C07J1/0011Androstane derivatives substituted in position 17 by a keto group
    • 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
    • C07J1/0014Androstane derivatives substituted in position 17 alfa, not substituted in position 17 beta
    • 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
    • C07J1/0033Androstane derivatives substituted in position 17 alfa and 17 beta
    • 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
    • C07J1/0033Androstane derivatives substituted in position 17 alfa and 17 beta
    • C07J1/004Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
    • C07J1/0048Alkynyl derivatives
    • 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
    • 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
    • C07J21/006Ketals at position 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J31/00Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • 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
    • C07J41/0038Normal 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
    • 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
    • C07J41/0094Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
    • 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
    • C07J5/0046Normal 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
    • 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
    • C07J7/004Normal 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
    • C07J7/0045Normal 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
    • 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
    • C07J7/004Normal 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
    • C07J7/005Normal 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
    • C07J7/0055Normal 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
    • 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
    • C07J7/008Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
    • C07J7/0085Normal 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Steroid Compounds (AREA)
NO882075A 1986-10-10 1988-05-11 9- av farmakologisk aktive pregnaner NO174748C (no)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP86201754 1986-10-10
EP87201340 1987-07-13
PCT/NL1987/000026 WO1988002753A2 (en) 1986-10-10 1987-10-09 9-alpha-hydroxy steroids and process for their preparation

Publications (4)

Publication Number Publication Date
NO882075L NO882075L (no) 1988-05-11
NO882075D0 true NO882075D0 (no) 1988-05-11
NO174748B NO174748B (no) 1994-03-21
NO174748C NO174748C (no) 1994-06-29

Family

ID=26103306

Family Applications (1)

Application Number Title Priority Date Filing Date
NO882075A NO174748C (no) 1986-10-10 1988-05-11 9- av farmakologisk aktive pregnaner

Country Status (19)

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

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EP0263569B1 (en) * 1986-10-10 1992-12-09 Roussel-Uclaf 9-alpha-hydroxysteroids, process for their preparation and process for the preparation of the corresponding 9(11)-dehydro-derivatives.
US4921638A (en) * 1986-11-05 1990-05-01 The Upjohn Company 17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one
EP0322081B1 (en) * 1987-12-23 1992-12-16 Roussel-Uclaf Microbiological preparation of 9-alpha-hydroxy-17-keto steroids
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
US5364847A (en) * 1989-03-10 1994-11-15 Endorecherche Inhibitors of sex steroid biosynthesis and methods for their production and use
US5372996A (en) * 1989-03-10 1994-12-13 Endorecherche, Inc. Method of treatment of androgen-related diseases
DE69034035T2 (de) * 1989-07-07 2004-01-22 Endorecherche Inc., Ste-Foy Methode zur behandlung androgenbedingter krankheiten
EP0485392B1 (en) * 1989-07-07 1998-09-09 Endorecherche Inc. Androgen derivatives for use in the inhibition of sex steroid activity
MY105302A (en) * 1989-11-27 1994-09-30 Schering Corp Process for dehydrating corticosteroid intermediates.
AU7556291A (en) * 1990-03-27 1991-10-21 Schering Corporation Process for 9alpha-hydroxy steroid dehydration
US5124154A (en) * 1990-06-12 1992-06-23 Insite Vision Incorporated Aminosteroids for ophthalmic use
US5252319A (en) * 1990-06-12 1993-10-12 Insite Vision Incorporated Aminosteroids for ophthalmic use
US5256408A (en) * 1990-06-12 1993-10-26 Insite Vision Incorporated Aminosteroids for ophthalmic use
US5209926A (en) * 1990-06-12 1993-05-11 Insite Vision Incorporated Aminosteroids for ophthalmic use
AU3582393A (en) * 1992-01-28 1993-09-01 Schering Corporation Novel steroid intermediates and processes for their preparation
WO1993023053A1 (en) * 1992-05-21 1993-11-25 Endorecherche Inc. 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.
EA009176B1 (ru) 1995-12-11 2007-12-28 Дж.Д.Серл Энд Ко. Способ получения 7-альфа-карбоксил-9,11-эпоксистероидов и промежуточных продуктов, используемых для их получения, и общий способ эпоксидирования по олефиновым двойным связям
US6887991B1 (en) * 1996-12-11 2005-05-03 G. D. Searle & Company Processes for preparation of 9, 11-epoxy steroids and intermediates useful therein
IL130182A0 (en) 1996-12-11 2000-06-01 Searle & Co Processes for preparation of 9,11-epoxy steroids and intermediates useful therein
US6610917B2 (en) * 1998-05-15 2003-08-26 Lester F. Ludwig Activity indication, external source, and processing loop provisions for driven vibrating-element environments
DE69942578D1 (de) 1998-05-22 2010-08-26 Univ R Bifunktionelle moleküle sowie darauf basierende therapien.
US7235655B2 (en) * 2002-03-22 2007-06-26 Pharmacia & Upjohn Company Processes to prepare eplerenone
RS90504A (en) * 2002-03-22 2006-10-27 Pharmacia Corporation C-17 spirolactonization and 6,7 oxidation of steroids
DK1889198T3 (da) 2005-04-28 2015-02-09 Proteus Digital Health Inc Farma-informatiksystem
US9062126B2 (en) 2005-09-16 2015-06-23 Raptor Pharmaceuticals Inc. Compositions comprising receptor-associated protein (RAP) variants specific for CR-containing proteins and uses thereof
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
AU2010216512B2 (en) 2009-02-20 2016-06-30 2-Bbb Medicines B.V. Glutathione-based drug delivery system
MY163048A (en) 2009-05-06 2017-08-15 Laboratory Skin Care Inc Dermal delivery compositions comprising active agent-calcium phosphate particle complexes and methods of using the same
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
HUE027821T2 (en) * 2011-12-23 2016-11-28 Crystal Pharma Sau A method for alkinylation of 16-substituted-17-ketosteroid derivatives
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
JP6781148B2 (ja) 2014-07-23 2020-11-04 スファエラ ファーマ プライベート リミテッド ヒドロキシステロイド化合物、それらの中間体、それらの調製方法、組成物および使用
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
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
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
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

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CA565369A (en) * 1958-10-28 P. Graber Robert 9,11-dihydroxy steroids and processes for preparing the same
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
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
US4383947A (en) * 1981-07-24 1983-05-17 The Upjohn Company Introduction of a fluorine atom
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
DE3585547D1 (de) * 1984-02-03 1992-04-16 Upjohn Co Steroide mit einer enamid- oder enimidgruppe sowie ihre herstellung.
US4705783A (en) * 1985-06-25 1987-11-10 Sri International 9α, 11β-substituted and 11β-substituted estranes
EP0263569B1 (en) * 1986-10-10 1992-12-09 Roussel-Uclaf 9-alpha-hydroxysteroids, process for their preparation and process for the preparation of the corresponding 9(11)-dehydro-derivatives.
US4921638A (en) * 1986-11-05 1990-05-01 The Upjohn Company 17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one

Also Published As

Publication number Publication date
IL84135A0 (en) 1988-03-31
GR3006576T3 (no) 1993-06-30
JPH01500907A (ja) 1989-03-30
EP0263569A3 (en) 1988-07-20
US5352809A (en) 1994-10-04
HU912420D0 (en) 1991-12-30
WO1988002753A3 (en) 1988-06-30
KR960010793B1 (ko) 1996-08-08
HU204063B (en) 1991-11-28
IE872722L (en) 1992-04-16
DK313188A (da) 1988-06-09
CN1036342C (zh) 1997-11-05
NO174748C (no) 1994-06-29
FI95710B (fi) 1995-11-30
ES2052550T3 (es) 1994-07-16
DK313188D0 (da) 1988-06-09
IE61985B1 (en) 1994-12-14
KR890700129A (ko) 1989-03-02
IL84135A (en) 1992-08-18
CN87106868A (zh) 1988-04-27
NO882075L (no) 1988-05-11
HU211080B (en) 1995-10-30
FI882461A0 (fi) 1988-05-25
PT85891A (en) 1987-11-01
AU607948B2 (en) 1991-03-21
CN1035182C (zh) 1997-06-18
NZ222103A (en) 1990-08-28
NO174748B (no) 1994-03-21
WO1988002753A2 (en) 1988-04-21
DE3783007D1 (de) 1993-01-21
CN1116208A (zh) 1996-02-07
HUT61568A (en) 1993-01-28
FI882461A (fi) 1988-05-25
FI95710C (fi) 1996-03-11
CA1334844C (en) 1995-03-21
JPH0826062B2 (ja) 1996-03-13
AU8106887A (en) 1988-05-06
DE3783007T2 (de) 1993-07-01
PT85891B (pt) 1990-07-31
DK175438B1 (da) 2004-10-18
EP0263569B1 (en) 1992-12-09
US5565588A (en) 1996-10-15
EP0263569A2 (en) 1988-04-13
HUT47130A (en) 1989-01-30

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