ATE41924T1 - Vitamin d3-derivate mit einem substituierten in position 2. - Google Patents

Vitamin d3-derivate mit einem substituierten in position 2.

Info

Publication number
ATE41924T1
ATE41924T1 AT85115418T AT85115418T ATE41924T1 AT E41924 T1 ATE41924 T1 AT E41924T1 AT 85115418 T AT85115418 T AT 85115418T AT 85115418 T AT85115418 T AT 85115418T AT E41924 T1 ATE41924 T1 AT E41924T1
Authority
AT
Austria
Prior art keywords
group
hydroxyl group
carbon atoms
vitamin
formula
Prior art date
Application number
AT85115418T
Other languages
English (en)
Inventor
Katsuhito Miyamoto
Noboru Kubodera
Kiyoshige Ochi
Isao Matsunaga
Eigoro Murayama
Original Assignee
Chugai Pharmaceutical Co Ltd
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 Chugai Pharmaceutical Co Ltd filed Critical Chugai Pharmaceutical Co Ltd
Application granted granted Critical
Publication of ATE41924T1 publication Critical patent/ATE41924T1/de

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J71/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0036Nitrogen-containing hetero ring
    • C07J71/0042Nitrogen only
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/02Nutrients, e.g. vitamins, minerals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/12Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C401/00Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J41/00Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
    • C07J41/0011Unsubstituted amino radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J41/00Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
    • C07J41/0027Azides
    • 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)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Rheumatology (AREA)
  • Endocrinology (AREA)
  • Nutrition Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
AT85115418T 1984-12-05 1985-12-04 Vitamin d3-derivate mit einem substituierten in position 2. ATE41924T1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP25571384 1984-12-05
EP85115418A EP0184206B1 (de) 1984-12-05 1985-12-04 Vitamin D3-Derivate mit einem Substituierten in Position 2

Publications (1)

Publication Number Publication Date
ATE41924T1 true ATE41924T1 (de) 1989-04-15

Family

ID=17282605

Family Applications (1)

Application Number Title Priority Date Filing Date
AT85115418T ATE41924T1 (de) 1984-12-05 1985-12-04 Vitamin d3-derivate mit einem substituierten in position 2.

Country Status (10)

Country Link
US (1) US4666634A (de)
EP (1) EP0184206B1 (de)
JP (1) JPH0623185B2 (de)
KR (1) KR940002981B1 (de)
CN (1) CN1008368B (de)
AT (1) ATE41924T1 (de)
CA (1) CA1330806C (de)
DE (1) DE3569238D1 (de)
DK (1) DK161197C (de)
IL (1) IL77122A (de)

Families Citing this family (89)

* Cited by examiner, † Cited by third party
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JP3030157B2 (ja) * 1991-03-13 2000-04-10 株式会社クラレ シクロヘキサントリオール誘導体
US5403832A (en) * 1992-03-12 1995-04-04 The Johns Hopkins University Vitamin D3 analogues
IL107748A (en) * 1992-11-27 1998-08-16 Chugai Pharmaceutical Co Ltd A method for producing a history of vitamin D.
EP0619306B1 (de) * 1993-04-05 1996-09-11 Wisconsin Alumni Research Foundation 19-Nor-vitamin-D3-Verbindung mit einem Substituent an die 2. Stelle
EP0806413B1 (de) * 1995-01-23 2001-12-12 Chugai Seiyaku Kabushiki Kaisha 2-substituierte vitamin-d3-derivate
TWI247001B (en) 1996-07-01 2006-01-11 Chugai Pharmaceutical Co Ltd The method for purifying vitamin d derivatives and its crystalline products
KR100554560B1 (ko) * 1996-07-01 2006-05-25 쥬가이 세이야쿠 가부시키가이샤 비타민d유도체결정및그의제조방법
US6316642B1 (en) 1997-03-17 2001-11-13 Wisconsin Alumni Research Foundation 26,27-Homologated-20-EPI-2alkyl-19-nor-vitamin D compounds
US6306844B1 (en) 1997-03-17 2001-10-23 Wisconsin Alumni Research Foundation Use of 2α-methyl-19-nor-20(S)-1α, 25-dihydroxyvitamin D3 to increase bone strength
US5843928A (en) * 1997-03-17 1998-12-01 Wisconsin Alumni Research Foundation 2-alkylidene-19-nor-vitamin D compounds
US5945410A (en) * 1997-03-17 1999-08-31 Wisconsin Alumni Research Foundation 2-alkyl-19-nor-vitamin D compounds
US6392071B1 (en) 1997-03-17 2002-05-21 Wisconsin Alumni: Research Foundation 26,27-homologated-20-EPI-2-alkylidene-19-nor-vitamin D compounds
WO1999043645A1 (en) * 1998-02-24 1999-09-02 Chugai Seiyaku Kabushiki Kaisha 24-hydroxyvitamin d derivatives
AU3167699A (en) 1998-04-10 1999-11-01 Chugai Seiyaku Kabushiki Kaisha Vitamin d derivatives substituted at the 2beta-position
US6114317A (en) * 1998-05-21 2000-09-05 Wisconsin Alumni Research Foundation Method of locking 1α-OH of vitamin D compounds in axial orientation
EP1158297A4 (de) * 1999-02-18 2002-04-10 Chugai Pharmaceutical Co Ltd Screeningverfahren für eine verbindung, die eine affinität für den vitamin d rezeptor hat
WO2001090061A1 (fr) * 2000-05-23 2001-11-29 Chugai Seiyaku Kabushiki Kaisha Derives de 5, 6-trans-2-alkylevitamine d
CA2410880C (en) * 2000-05-31 2009-03-03 Wisconsin Alumni Research Foundation 2-ethyl and 2-ethylidene-19-nor-vitamin d compounds
ATE509910T1 (de) * 2000-06-15 2011-06-15 Chugai Pharmaceutical Co Ltd Vitamin d derivate mit einem 22-oxa- oder 22-thia-atom, einer sauer-, ester- oder amid- substitutierten c17-seitenkette und einer 16(17)- doppelbindung
CN1217664C (zh) * 2000-07-14 2005-09-07 威斯康星校友研究基金会 2-亚甲基-19-去甲-20(S)-1α,25-二羟维生素D3增加骨强度的用途
US20040030167A1 (en) * 2000-08-08 2004-02-12 Hiroaki Takayama 3-Methyl-20-epi-vitamin d derivatives
WO2002020021A1 (en) 2000-09-08 2002-03-14 Wisconsin Alumni Research Foundation 1alpha-hydroxy-2-methylene-19-nor-homopregnacalciferol and its therapeutic applications
WO2002066424A1 (en) * 2001-02-23 2002-08-29 Chugai Seiyaku Kabushiki Kaisha Vitamin d derivative having substituent in 2-position
US6627622B2 (en) * 2002-02-18 2003-09-30 Wisconsin Alumni Research Foundation (20S)-1α-hydroxy-2-methylene-19-nor-bishomopregnacalciferol and its uses
US6566352B1 (en) 2002-02-18 2003-05-20 Wisconsin Alumni Research Foudation 1 α-hydroxy-2-methylene-19-nor-pregnacalciferol and its uses
US20030195175A1 (en) * 2002-03-25 2003-10-16 Deluca Hector F. Use of carbon-2-modified-vitamin D analogs to induce the formation of new bone
ES2276062T3 (es) * 2002-03-29 2007-06-16 Wisconsin Alumni Research Foundation Metodo para sintetizar 1-alfa-hidroxi-2-metilen-19-nor-homopregnacalciferol.
WO2004012743A1 (ja) * 2002-08-01 2004-02-12 Chugai Seiyaku Kabushiki Kaisha 乾癬治療剤
BRPI0407104A (pt) * 2003-01-30 2006-01-24 Teijin Pharma Ltd Composto, agente terapêutico, composição farmacêutica, e, processo para sintetizar um composto
JP5005340B2 (ja) * 2003-04-10 2012-08-22 ウィスコンシン・アルムニ・リサーチ・ファウンデーション 2−プロピリデン−19−ノル−ビタミンd化合物
US6894037B2 (en) * 2003-07-03 2005-05-17 Wisconsin Alumni Research Foundation 2-methylene-19-nor-20(S)-25-methyl-1α-hydroxycalciferol and its uses
US20050009792A1 (en) * 2003-07-08 2005-01-13 Deluca Hector F. (20S)-1alpha-hydroxy-2-methylene-19-nor-vitamin D3 and its uses
JP5009617B2 (ja) * 2003-08-20 2012-08-22 ウイスコンシン アラムニ リサーチ ファンデーション 2−メチレン−19−ノル−ビタミンd2化合物
JP4921794B2 (ja) * 2004-02-06 2012-04-25 中外製薬株式会社 Ed−71製剤
US7713951B2 (en) * 2004-04-09 2010-05-11 Wisconsin Alumni Research Foundation 2-alkylidene-18,19-dinor-vitamin D compounds
ATE467614T1 (de) * 2004-11-22 2010-05-15 Wisconsin Alumni Res Found 2-methylen-19,26,27-trinor-(20s)-1-alpha- hydroxyvitamin d3 and dessen verwendungen
US8222235B2 (en) * 2004-11-22 2012-07-17 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20R)-1α-hydroxy-bishomopregnacalciferol
AU2005309819A1 (en) * 2004-11-22 2006-06-01 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20S)-1alpha-hydroxy-trishomopregnacalciferol
CA2588063C (en) * 2004-11-22 2012-10-16 Wisconsin Alumni Research Foundation 2-methylene-19,21-dinor-1.alpha.-hydroxy-bishomopregnacalciferol
MX2007006545A (es) * 2004-11-22 2007-09-21 Wisconsin Alumni Res Found 2a-metil-19-nor-1a-hidroxi-homopregnacalciferol y sus usos.
JP5161582B2 (ja) * 2004-11-22 2013-03-13 ウィスコンシン・アルムニ・リサーチ・ファウンデーション 17,20(z)−デヒドロビタミンd類似体およびそれらの使用
US7563783B2 (en) * 2005-02-11 2009-07-21 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20S-24S)-1α,25-dihydroxyvitamin-D2
WO2006086608A1 (en) * 2005-02-11 2006-08-17 Wisconsin Alumni Research Foundation 2-METHYLENE-19-NOR-(20S-24EPI)-1α,25-DIHYDROXYVITAMIN-D2
EP1865965A4 (de) * 2005-03-29 2010-06-02 Wisconsin Alumni Res Found 2-methylen-19-nor-(23s)-25-dehydro-1 -hydroxyvitamin-d3-26,23-lacton und 2-methylen-19-nor-(23r)-25-dehydro-1 -hydroxyvitamin-d3-26,23-lacton
NZ563758A (en) * 2005-05-03 2010-04-30 Wisconsin Alumni Res Found 19,26,27-Trinor-1alpha,25-dihydroxyvitamin D3 compounds
ES2533719T3 (es) * 2005-08-30 2015-04-14 Wisconsin Alumni Research Foundation Análogos Des-C,D de 1alfa,25-dihidroxi-19-norvitamina D3
NZ567438A (en) * 2005-09-22 2010-11-26 Wisconsin Alumni Res Found 19,23,24,25,26,27-Hexanor-1alpha-hydroxyvitamin D3
US7528122B2 (en) * 2006-02-02 2009-05-05 Wisconsin Alumni Research Foundation Vitamin D analog—NEL, methods and uses thereof
US7803789B2 (en) 2006-02-02 2010-09-28 Wisconsin Alumni Research Foundation Vitamin D analog—RAK, methods and uses thereof
EP2010483A2 (de) * 2006-04-05 2009-01-07 Wisconsin Alumni Research Foundation 1.alpha.-hydroxy-2-(3'-hydroxypropyliden)-19-nor-vitamin-d-verbindungen sowie verfahren zu ihrer herstellung und verwendung
US20090281340A1 (en) * 2006-04-05 2009-11-12 Deluca Hector F 1alpha-hydroxy-2-(3'-hydroxypropylidene)-19-nor-vitamin d compounds and methods of making and treatment thereof
MX2008012672A (es) * 2006-04-06 2008-10-15 Wisconsin Alumni Res Found Analogos de 2-metilen-1a-hidroxi-18,19,21-trinor vitamina d3 y sus usos.
EP2001842B1 (de) * 2006-04-06 2012-06-06 Wisconsin Alumni Research Foundation 2-methylen-1-alpha-hydroxy-19,21-dinor-vitamin-d3-analoge und deren anwendungen
US7538098B2 (en) * 2006-04-06 2009-05-26 Wisconsin Alumni Research Foundation 19-nor-vitamin D analogs with 1,2 or 3,2 heterocyclic ring
ATE523487T1 (de) * 2006-04-06 2011-09-15 Wisconsin Alumni Res Found 2-methylen-1-alpha-dihydroxy-19,21-dinor-vitami - d3-analoga und ihre anwendung
CA2639585A1 (en) * 2006-04-06 2007-10-06 Wisconsin Alumni Research Foundation 2-methylene-1.alpha., 25-dihydroxy-18, 19, 21-trinorvitamin d3 and uses thereof
AU2007298673A1 (en) 2006-04-06 2008-03-27 Wisconsin Alumni Research Foundation 2- substituted-1alpha, 25-dihydroxy-19,26,27-trinor vitamin D analogs and uses thereof
US7763598B2 (en) * 2006-04-10 2010-07-27 Wisconsin Alumni Research Foundation 1α-hydroxy-2-(3′-hydroxypropylidene)-19-nor-vitamin D compounds with a 1,1-dimethylpropyl side chain
CA2662992A1 (en) * 2006-09-28 2008-04-03 Wisconsin Alumni Research Foundation 2-methylene-(20r,25s)-19,27-dinor-(22e)-vitamin d analogs
AU2007300211A1 (en) * 2006-09-28 2008-04-03 Wisconsin Alumni Research Foundation 2-methylene-(20S,25S)-19,27-dinor-(22E)-vitamin D analogs
US20090075953A1 (en) * 2007-09-15 2009-03-19 Protia, Llc Deuterium-enriched ed-71
US7718637B2 (en) * 2007-12-28 2010-05-18 Wisconsin Alumni Research Foundation (20S)-23,23-difluoro-methylene-19-nor-bishomopregnacalciferol-vitamin D analogs
US8609643B2 (en) * 2007-12-28 2013-12-17 Wisconsin Alumni Research Foundation 2-methylene-(20S,25R)-19,26-dinor-vitamin D analogs
EP2240440A2 (de) * 2007-12-28 2010-10-20 Wisconsin Alumni Research Foundation 2-methylen-(20s,25s)-19,26-dinor-vitamin-d-analoga
JP2011508744A (ja) * 2007-12-28 2011-03-17 ウィスコンシン アラムナイ リサーチ ファンデーション (20r)−23,23−ジフルオロ−2−メチレン−19−ノル−ビスホモプレグナカルシフェロール−ビタミンd類縁体
WO2009086440A1 (en) * 2007-12-28 2009-07-09 Wisconsin Alumni Research Foundation 2-methylene-20-methyl-19,24,25,26,27-pentanor-vitamin d analogs
US8399439B2 (en) * 2008-07-10 2013-03-19 Wisconsin Alumni Research Foundation 2-methylene-19,26-dinor-(20S,22E,25R)-vitamin D analogs
US7713953B2 (en) * 2008-07-10 2010-05-11 Wisconsin Alumni Research Foundation 2-methylene-(22E)-25-(1-methylene-hexyl)-26,27-cyclo-22-dehydro-19-nor-vitamin D analogs
US7888339B2 (en) * 2008-07-10 2011-02-15 Wisconsin Alumni Research Foundation 2-methylene-20(21)-dehydro-19-nor-vitamin D analogs
US7893043B2 (en) * 2008-07-10 2011-02-22 Wisconsin Alumni Research Foundation 2-methylene-(17Z)-17(20)-dehydro-19,21-dinor-vitamin D analogs
US8222236B2 (en) * 2008-07-10 2012-07-17 Wisconsin Alumni Research Foundation 2-methylene-(20E)-20(22)-dehydro-19-nor-vitamin D analogs
JP2013506685A (ja) 2009-10-02 2013-02-28 ウィスコンシン・アルムニ・リサーチ・ファウンデーション (20S,22E)−2−メチレン−19−ノル−22−エン−1α,25−ジヒドロキシビタミンD3類似体
US8642579B2 (en) 2009-10-02 2014-02-04 Wisconsin Alumni Research Foundation 1-desoxy-2-methylene-19-nor-vitamin D analogs and their uses
AU2010310654B2 (en) 2009-10-21 2015-05-14 Wisconsin Alumni Research Foundation Method of preventing Type 1 diabetes
JP2011241170A (ja) * 2010-05-18 2011-12-01 Mercian Corp ビタミンd誘導体およびその製造方法
WO2012065050A1 (en) 2010-11-12 2012-05-18 Wisconsin Alumni Research Foundation 22-haloacetoxy-homopregnacalciferol analogs and their uses
WO2012151058A1 (en) 2011-05-03 2012-11-08 Wisconsin Alumni Research Foundation (20s)-24-(p-toluenesulfonyloxy)-25,26,27-trinorvitamin d3 analogs and their uses
WO2012158794A1 (en) 2011-05-17 2012-11-22 Wisconsin Alumni Research Foundation N-cyclopropyl-(20r)-2-methylene-19,26,27-trinor-25-aza-vitamin d analogs and their uses
EP2714656B1 (de) 2011-06-03 2017-05-03 Wisconsin Alumni Research Foundation (22e) -2-methylen-26,27-cyclo-22-dehydro-1alpha-hydroxy-19-norvitamin-d3-derivate
WO2012174095A1 (en) 2011-06-14 2012-12-20 Wisconsin Alumni Research Foundation 3-desoxy-2-methylene-19-nor-vitamin d analogs and their uses
US10479764B2 (en) 2011-06-28 2019-11-19 Wisconsin Alumni Research Foundation 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-vitamin D analogs
US20130178449A1 (en) 2011-07-18 2013-07-11 Wisconsin Alumni Research Foundation 2-Methylene-20(21)-Dehydro-19,24,25,26,27-Pentanor-Vitamin D Analogs
US8729054B2 (en) 2011-10-21 2014-05-20 Wisconsin Alumni Research Foundation 3-desoxy-2-methylene-vitamin D analogs and their uses
JP6072811B2 (ja) * 2011-10-21 2017-02-01 ウイスコンシン アラムニ リサーチ ファンデーション 2−メチレン−ビタミンd類似体およびそれらの使用
WO2013059060A1 (en) 2011-10-21 2013-04-25 Wisconson Alumni Research Foundation 2-methylene-vitamin d analogs and their uses
US8785422B2 (en) * 2012-06-06 2014-07-22 Wisconsin Alumni Research Foundation A-ring modified 19-nor-vitamin D analogs and their uses
JP2018030839A (ja) * 2016-08-23 2018-03-01 日産化学工業株式会社 ビタミンd3誘導体の新規な結晶形及びその製造方法
CN107540589B (zh) * 2017-09-14 2022-05-03 上海彩迩文生化科技有限公司 一种艾尔骨化醇晶型、药物组合物及制备方法和应用
CN109456244A (zh) * 2018-12-12 2019-03-12 无锡福祈制药有限公司 一种维生素d3类化合物及其制备方法

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JPS5726273B2 (de) * 1974-01-11 1982-06-03
JPS5726272B2 (de) * 1974-01-11 1982-06-03
JPS5119752A (en) * 1974-08-07 1976-02-17 Masayuki Ishikawa 1 arufua* 2 arufuaa jihidorokishikorekarushifuerooruno seiho
US4254045A (en) * 1980-04-21 1981-03-03 Wisconsin Alumni Research Foundation 1α-Hydroxy-2β-fluorocholecalciferol
US4307025A (en) * 1981-02-17 1981-12-22 Wisconsin Alumni Research Foundation 1α, 25-dihydroxy-2β-fluorovitamin D3

Also Published As

Publication number Publication date
IL77122A (en) 1990-11-29
KR860004850A (ko) 1986-07-14
DK561485D0 (da) 1985-12-04
EP0184206A2 (de) 1986-06-11
DK161197C (da) 1991-11-25
CN1008368B (zh) 1990-06-13
CA1330806C (en) 1994-07-19
US4666634A (en) 1987-05-19
EP0184206B1 (de) 1989-04-05
EP0184206A3 (en) 1987-01-14
JPS61267549A (ja) 1986-11-27
CN85108857A (zh) 1986-07-09
DK561485A (da) 1986-06-06
JPH0623185B2 (ja) 1994-03-30
KR940002981B1 (ko) 1994-04-09
DK161197B (da) 1991-06-10
DE3569238D1 (en) 1989-05-11
IL77122A0 (en) 1986-04-29

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