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

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0036—Nitrogen-containing hetero ring
    • C07J71/0042—Nitrogen only
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005—Normal 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
    • C07J41/0011—Unsubstituted amino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005—Normal 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
    • C07J41/0027—Azides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal 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)
  • Pharmacology & Pharmacy (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Endocrinology (AREA)
  • Rheumatology (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
Publication number Priority date Publication date Assignee Title
DK0503630T3 (da) * 1991-03-13 1996-01-29 Kuraray Co Cyclohexantriolderivater
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.
DE69400495T2 (de) * 1993-04-05 1997-04-30 Wisconsin Alumni Res Found 19-Nor-vitamin-D3-Verbindung mit einem Substituent an die 2. Stelle
ATE210642T1 (de) * 1995-01-23 2001-12-15 Chugai Pharmaceutical Co Ltd 2-substituierte vitamin-d3-derivate
TW584627B (en) 1996-07-01 2004-04-21 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
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
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
US6316642B1 (en) 1997-03-17 2001-11-13 Wisconsin Alumni Research Foundation 26,27-Homologated-20-EPI-2alkyl-19-nor-vitamin D compounds
JP4357114B2 (ja) * 1998-02-24 2009-11-04 中外製薬株式会社 ２４−ヒドロキシビタミンｄ誘導体
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
CN1341213A (zh) * 1999-02-18 2002-03-20 中外制药株式会社 筛选具有维生素d受体亲和性的化合物的方法
AU2001256791A1 (en) * 2000-05-23 2001-12-03 Chugai Seiyaku Kabushiki Kaisha 5,6-trans-2-alkylvitamin d derivatives
US6806262B2 (en) * 2000-05-31 2004-10-19 Wisconsin Alumni Research Foundation 2-ethyl and 2-ethylidene-19-nor-vitamin D compounds
IL153395A0 (en) * 2000-06-15 2003-07-06 Chugai Pharmaceutical Co Ltd Vitamin d derivatives
WO2002005823A2 (en) * 2000-07-14 2002-01-24 Wisconsin Alumni Research Foundation USE OF 2-METHYLENE-19-NOR-20(S)-1α,25-DIHYDROXYVITAMIN D3 TO INCREASE BONE STRENGTH
WO2002012182A1 (fr) * 2000-08-08 2002-02-14 Chugai Seiyaku Kabushiki Kaisha Derives de 3-methyl-20-epi-vitamine d
WO2002020021A1 (en) 2000-09-08 2002-03-14 Wisconsin Alumni Research Foundation 1alpha-hydroxy-2-methylene-19-nor-homopregnacalciferol and its therapeutic applications
JPWO2002066424A1 (ja) * 2001-02-23 2004-06-17 中外製薬株式会社 ２位に置換基を有するビタミンｄ誘導体
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
BR0307896A (pt) * 2002-03-29 2004-12-07 Wisconsin Alumni Res Found Método de produção de 1(alfa)-hidroxi-2-metileno-19-nor-homopregnacalcif erol
WO2004012743A1 (ja) * 2002-08-01 2004-02-12 Chugai Seiyaku Kabushiki Kaisha 乾癬治療剤
AU2004207719B9 (en) * 2003-01-30 2009-10-01 Teijin Limited Vitamin D3 lactone derivative
BRPI0409194A (pt) * 2003-04-10 2006-04-11 Wisconsin Alumni Res Found compostos, composição farmacêutica e método de tratamento de doença metabólica do osso, da psorìase, da leucemia, cáncer do cólon, cáncer da mama, cáncer da pele ou cáncer da próstata, de doença auto-imune, de doença inflamatória do intestino e de aumento da resistência do osso
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
AU2004266706B2 (en) * 2003-08-20 2009-07-30 Wisconsin Alumni Research Foundation 2-methylene-19-nor-vitamin D2 compounds
WO2005074943A1 (ja) * 2004-02-06 2005-08-18 Chugai Seiyaku Kabushiki Kaisha Ｅｄ−７１製剤
US7713951B2 (en) * 2004-04-09 2010-05-11 Wisconsin Alumni Research Foundation 2-alkylidene-18,19-dinor-vitamin D compounds
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
CA2588412A1 (en) * 2004-11-22 2006-06-01 Wisconsin Alumni Research Foundation 2alpha-methyl-19-nor-1alpha-hydroxy-homopregnacalciferol and its uses
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
JP2008520708A (ja) * 2004-11-22 2008-06-19 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−（２０Ｒ）−１α−ヒドロキシ−ビスホモプレグナカルシフェロール
EP1827452B1 (de) * 2004-11-22 2011-03-02 Wisconsin Alumni Research Foundation 2-methylen-19,21-dinor-1alpha-hydroxy-bishomopregnacalciferol
US7541348B2 (en) * 2004-11-22 2009-06-02 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20S)-1α-hydroxy-trishomopregnacalciferol
NZ561076A (en) * 2005-02-11 2010-01-29 Wisconsin Alumni Res Found 2-methylene-19-nor-(20S-24EPI)-1alpha,25-dihydroxyvitamin-D2
AU2006213727B2 (en) * 2005-02-11 2011-08-18 Wisconsin Alumni Research Foundation 2-methylene-19-nor- (20S-24S) - 1alpha, 25-dihydroxyvitamin-D2
AU2006230296B2 (en) * 2005-03-29 2011-07-07 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(23s)-25-dehydro-1alpha-hydroxyvitamin D3-26,23-lactone and 2-methylene-19-nor-(23R)-25-dehydro-1alpha-hydroxyvitamin D3-26,23-lactone
CA2605727A1 (en) * 2005-05-03 2006-11-09 Wisconsin Alumni Research Foundation 19,26,27-trinor-1.alpha.,25-dihydroxyvitamin d3 compounds
AU2006284622B2 (en) * 2005-08-30 2011-10-06 Wisconsin Alumni Research Foundation Des-C,D analogs of 1alpha,25-dihydroxy-19-norvitamin D3
WO2007038094A1 (en) * 2005-09-22 2007-04-05 Wisconsin Alumni Research Foundation 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
US7648973B2 (en) * 2006-04-06 2010-01-19 Wisconsin Alumni Research Foundation 2-methylene-1α,25-dihydroxy-19,21-dinorvitamin D3 analogs and uses thereof
JP2009533483A (ja) * 2006-04-06 2009-09-17 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−１α，２５−ジヒドロキシ−１８，１９，２１−トリノルビタミンＤ３およびその使用
WO2008026078A2 (en) * 2006-04-06 2008-03-06 Wisconsin Alumni Research Foundation 19-nor-vitamin d analogs with 1,2,or 3,2 heterocyclic ring
MX2008012671A (es) 2006-04-06 2008-10-15 Wisconsin Alumni Res Found Analogos 1 a,25-dihidroxi- 19, 26,27-trinor vitamina d 2-sustituidos y sus usos.
AU2007298651A1 (en) * 2006-04-06 2008-03-27 Wisconsin Alumni Research Foundation 2-methylene-1 alpha-hydroxy-18,19,21-trinorvitamin D3 analogs and uses thereof
CA2646909A1 (en) * 2006-04-06 2008-03-27 Hector F. Deluca 2-methylene-1alpha-hydroxy-19,21-dinorvitamin d3 analogs and uses thereof
DE602007012216D1 (de) * 2006-04-10 2011-03-10 Wisconsin Alumni Res Found 1-alpha-hydroxy-2-(3'-hydroxypropyliden)-19-nor-vitamin-d-verbindungen mit einer 1,1-dimethylpropyl-seitenkette
ATE552238T1 (de) * 2006-09-28 2012-04-15 Wisconsin Alumni Res Found 2-methylen-(20s,25s)-19,27-dinor-(22e)-vitamin- - analoga
MX2009003241A (es) * 2006-09-28 2009-05-05 Wisconsin Alumni Res Found Analogos de 2-metilen-(20r,25s)-19,27-dinor-(22e)-vitamina d.
US20090075953A1 (en) * 2007-09-15 2009-03-19 Protia, Llc Deuterium-enriched ed-71
ATE552239T1 (de) * 2007-12-28 2012-04-15 Wisconsin Alumni Res Found 2-methylen-20-methyl-19,24,25,26,27-pentanor- vitamin-d-analoga
CA2710954C (en) * 2007-12-28 2015-07-21 Wisconsin Alumni Research Foundation (20s)-23,23-difluoro-2-methylene-19-nor-bishomopregnacalciferol-vitamin d analogs
CA2710970A1 (en) * 2007-12-28 2009-07-09 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
US7718638B2 (en) * 2007-12-28 2010-05-18 Wisconsin Alumni Research Foundation (20R)-23,23-difluoro-2-methylene-19-nor-bishomopregnacalciferol-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
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
US8222236B2 (en) * 2008-07-10 2012-07-17 Wisconsin Alumni Research Foundation 2-methylene-(20E)-20(22)-dehydro-19-nor-vitamin D analogs
EP2525799B1 (de) 2009-10-02 2014-09-03 Wisconsin Alumni Research Foundation (20s,22e)-2-methylen-19-nor-22-en-1alpha,25-dihydroxyvitamin-d3-analoga
CA2776464C (en) 2009-10-02 2017-10-24 Wisconsin Alumni Research Foundation 1-desoxy-2-methylene-19-nor-vitamin d analogs and their uses
ES2437921T3 (es) 2009-10-21 2014-01-15 Wisconsin Alumni Research Foundation Método para prevenir la diabetes tipo 1
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
US8987235B2 (en) 2011-05-17 2015-03-24 Wisconsin Alumni Research Foundation N-cyclopropyl-(20R)-2-methylene-19,26,27-trinor-25-aza-vitamin D analogs and their uses
US9834512B2 (en) 2011-06-03 2017-12-05 Wisconsin Alumni Research Foundation (22E)-2-methylene-26,27-cyclo-22-dehydro-1α-hydroxy-19-norvitamin D3 derivatives
JP6035331B2 (ja) 2011-06-14 2016-11-30 ウイスコンシン アラムニ リサーチ ファンデーション ３−デスオキシ−２−メチレン−１９−ノル−ビタミンｄ類似体およびそれらの使用
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
US8410080B1 (en) 2011-10-21 2013-04-02 Wisconsin Alumni Research Foundation 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
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
DK561485D0 (da) 1985-12-04
EP0184206B1 (de) 1989-04-05
EP0184206A3 (en) 1987-01-14
EP0184206A2 (de) 1986-06-11
DK561485A (da) 1986-06-06
JPH0623185B2 (ja) 1994-03-30
CN85108857A (zh) 1986-07-09
CN1008368B (zh) 1990-06-13
CA1330806C (en) 1994-07-19
IL77122A (en) 1990-11-29
JPS61267549A (ja) 1986-11-27
DE3569238D1 (en) 1989-05-11
DK161197B (da) 1991-06-10
KR940002981B1 (ko) 1994-04-09
IL77122A0 (en) 1986-04-29
KR860004850A (ko) 1986-07-14
US4666634A (en) 1987-05-19
DK161197C (da) 1991-11-25

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