IL77122A - Vitamin d3 derivatives having a substituent at 2-position and process for the their preparation - Google Patents

Vitamin d3 derivatives having a substituent at 2-position and process for the their preparation

Info

Publication number
IL77122A
IL77122A IL77122A IL7712285A IL77122A IL 77122 A IL77122 A IL 77122A IL 77122 A IL77122 A IL 77122A IL 7712285 A IL7712285 A IL 7712285A IL 77122 A IL77122 A IL 77122A
Authority
IL
Israel
Prior art keywords
group
hydroxyl group
carbon atoms
vitamin
substituent
Prior art date
Application number
IL77122A
Other languages
English (en)
Other versions
IL77122A0 (en
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
Publication of IL77122A0 publication Critical patent/IL77122A0/xx
Publication of IL77122A publication Critical patent/IL77122A/xx

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)
  • 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)
IL77122A 1984-12-05 1985-11-22 Vitamin d3 derivatives having a substituent at 2-position and process for the their preparation IL77122A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP25571384 1984-12-05

Publications (2)

Publication Number Publication Date
IL77122A0 IL77122A0 (en) 1986-04-29
IL77122A true IL77122A (en) 1990-11-29

Family

ID=17282605

Family Applications (1)

Application Number Title Priority Date Filing Date
IL77122A IL77122A (en) 1984-12-05 1985-11-22 Vitamin d3 derivatives having a substituent at 2-position and process for the their preparation

Country Status (10)

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

Families Citing this family (89)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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.
DE69400495T2 (de) * 1993-04-05 1997-04-30 Wisconsin Alumni Res Found 19-Nor-vitamin-D3-Verbindung mit einem Substituent an die 2. Stelle
EP0806413B1 (en) * 1995-01-23 2001-12-12 Chugai Seiyaku Kabushiki Kaisha 2-substituted vitamin d3 derivatives
KR100554560B1 (ko) * 1996-07-01 2006-05-25 쥬가이 세이야쿠 가부시키가이샤 비타민d유도체결정및그의제조방법
TWI247001B (en) * 1996-07-01 2006-01-11 Chugai Pharmaceutical Co Ltd The method for purifying vitamin d derivatives and its crystalline products
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
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
US5945410A (en) 1997-03-17 1999-08-31 Wisconsin Alumni Research Foundation 2-alkyl-19-nor-vitamin D compounds
DE69939106D1 (de) * 1998-02-24 2008-08-28 Chugai Pharmaceutical Co Ltd Verfahren zur Herstellung von ED-71
EP1070704A4 (en) 1998-04-10 2001-11-07 Chugai Pharmaceutical Co Ltd VITAMIN D DERIVATIVES SUBSTITUTED IN THE 2 BETA 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 (en) * 1999-02-18 2002-04-10 Chugai Pharmaceutical Co Ltd METHOD FOR IDENTIFYING A COMPONENT HAVING AFFINITY FOR THE VITAMIN D RECEPTOR
AU2001256791A1 (en) * 2000-05-23 2001-12-03 Chugai Seiyaku Kabushiki Kaisha 5,6-trans-2-alkylvitamin d derivatives
WO2001092221A1 (en) 2000-05-31 2001-12-06 Wisconsin Alumni Research Foundation 2-ethyl and 2-ethylidene-19-nor-vitamin d compounds
CN100469764C (zh) * 2000-06-15 2009-03-18 中外制药株式会社 维生素d衍生物
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
WO2002012182A1 (fr) * 2000-08-08 2002-02-14 Chugai Seiyaku Kabushiki Kaisha Derives de 3-methyl-20-epi-vitamine d
AU2001275445B2 (en) 2000-09-08 2006-07-27 Wisconsin Alumni Research Foundation 1alpha-hydroxy-2-methylene-19-nor-homopregnacalciferol and its therapeutic applications
WO2002066424A1 (fr) * 2001-02-23 2002-08-29 Chugai Seiyaku Kabushiki Kaisha Derive de vitamine d possedant un substituant en position 2
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.
JPWO2004012743A1 (ja) * 2002-08-01 2006-09-21 中外製薬株式会社 乾癬治療剤
JP4361528B2 (ja) * 2003-01-30 2009-11-11 帝人ファーマ株式会社 ビタミンｄ３ラクトン誘導体
US20060293291A1 (en) * 2003-04-10 2006-12-28 Deluca Hector F 2-Propylidene-19-nor-vitamin d compounds
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
WO2005018658A1 (en) * 2003-08-20 2005-03-03 Wisconsin Alumni Research Foundation 2-methylene-19-nor-vitamin d2 compounds
ES2638836T3 (es) * 2004-02-06 2017-10-24 Chugai Seiyaku Kabushiki Kaisha Preparación de ED-71
US7713951B2 (en) * 2004-04-09 2010-05-11 Wisconsin Alumni Research Foundation 2-alkylidene-18,19-dinor-vitamin D compounds
US8604008B2 (en) * 2004-11-22 2013-12-10 Wisconsin Alumni Research Foundation 2-methylene-19,21-dinor-1α-hydroxy-bishomopregnacalciferol
EP1831161B1 (en) * 2004-11-22 2017-07-26 Wisconsin Alumni Research Foundation Medical and cosmetic uses of 2-methylene-19-nor-(20r)-1-alpha-hydroxy-bishomopregnacalciferol
DE602005021245D1 (de) * 2004-11-22 2010-06-24 Wisconsin Alumni Res Found 2-methylen-19,26,27-trinor-(20s)-1-alpha-hydroxyvitamin d3 and dessen verwendungen
JP2008520709A (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−（２０Ｓ）−１α−ヒドロキシ−トリスホモプレグナカルシフェロール
EP1828114B1 (en) * 2004-11-22 2010-04-21 Wisconsin Alumni Research Foundation 17,20(e)-dehydro vitamin d analogs and their uses
NZ555279A (en) * 2004-11-22 2010-12-24 Wisconsin Alumni Res Found 2alpha-methyl-19-nor-1alpha-hydroxy-homopregnacalciferol and its uses
CA2597624C (en) * 2005-02-11 2012-08-14 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20s-24s)-1.alpha.,25-dihydroxyvitamin-d2
US7511030B2 (en) * 2005-02-11 2009-03-31 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20S-24epi)-1α,25-dihydroxyvitamin D2
CA2603328A1 (en) * 2005-03-29 2006-10-05 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(23s)-25-dehydro-1.alpha.-hydroxyvitamin d3-26,23-lactone and 2-methylene-19-nor-(23r)-25-dehydro-1.alpha.-hydroxyvitamin d3-26,23-lactone
WO2006119309A2 (en) * 2005-05-03 2006-11-09 Wisconsin Alumni Research Foundation 19,26,27-TRINOR-1α,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
US7803789B2 (en) 2006-02-02 2010-09-28 Wisconsin Alumni Research Foundation Vitamin D analog—RAK, methods and uses thereof
US7528122B2 (en) * 2006-02-02 2009-05-05 Wisconsin Alumni Research Foundation Vitamin D analog—NEL, methods and uses thereof
NZ571896A (en) * 2006-04-05 2011-09-30 Wisconsin Alumni Res Found 1-Alpha.-hydroxy-2-(3'-hydroxypropylidene)-19-nor-vitamin D compounds and methods of making and use thereof
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
NZ570711A (en) 2006-04-06 2012-10-26 Wisconsin Alumni Res Found 2-Substituted-1alpha, 25-dihydroxy-19,26,27-trinor vitamin D analogs and uses thereof
WO2007118198A2 (en) * 2006-04-06 2007-10-18 Wisconsin Alumni Research Foundation 2-METHYLENE-1α,25-DIHYDROXY-19,21-DINORVITAMIN D3 ANALOGS AND USES THEREOF
MX2008012114A (es) * 2006-04-06 2009-03-06 Wisconsin Alumni Res Found Analogos 19-nor-vitamina d con anillo 1,2, o 3,2 heterociclico.
JP2009532457A (ja) * 2006-04-06 2009-09-10 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−ヒドロキシ−１８，１９，２１−トリノルビタミンＤ３類縁体およびその使用
US7704981B2 (en) * 2006-04-06 2010-04-27 Wisconsin Alumni Research Foundation 2-methylene-1alpha,25-dihydroxy-18,19,21-trinorvitamin D3 and uses thereof
JP2009532458A (ja) * 2006-04-06 2009-09-10 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−ヒドロキシ−１９，２１−ジノルビタミンＤ３類縁体およびその使用
MX2008012674A (es) * 2006-04-10 2008-10-15 Wisconsin Alumni Res Found Compuestos de 1 a-hidroxi-2-(3'-hidroxipropiliden)-19-nor-vitamina d con una cadena lateral 1,1-dimetilpropilo.
AU2007300211A1 (en) * 2006-09-28 2008-04-03 Wisconsin Alumni Research Foundation 2-methylene-(20S,25S)-19,27-dinor-(22E)-vitamin D analogs
CA2662992A1 (en) * 2006-09-28 2008-04-03 Wisconsin Alumni Research Foundation 2-methylene-(20r,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
AU2008345085A1 (en) * 2007-12-28 2009-07-09 Wisconsin Alumni Research Foundation 2-methylene-(20S,25S)-19,26-dinor-vitamin D analogs
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
CA2710970A1 (en) * 2007-12-28 2009-07-09 Wisconsin Alumni Research Foundation 2-methylene-(20s,25r)-19,26-dinor-vitamin d analogs
WO2009086437A1 (en) * 2007-12-28 2009-07-09 Wisconsin Alumni Research Foundation (20r)-23,23-difluoro-2-methylene-19-nor-bishomopregnacalciferol-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
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
US8399439B2 (en) * 2008-07-10 2013-03-19 Wisconsin Alumni Research Foundation 2-methylene-19,26-dinor-(20S,22E,25R)-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
AU2010300539B9 (en) 2009-10-02 2018-07-19 Wisconsin Alumni Research Foundation 1-desoxy-2-methylene-19-nor-vitamin D analogs and their uses
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
WO2011050163A1 (en) 2009-10-21 2011-04-28 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
US9290447B2 (en) 2011-05-03 2016-03-22 Wisconsin Alumni Research Foundation (20R) and (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
EP2714656B1 (en) 2011-06-03 2017-05-03 Wisconsin Alumni Research Foundation (22e)-2-methylene-26,27-cyclo-22-dehydro-1alpha-hydroxy-19-norvitamin d3 derivatives
CA2824870C (en) 2011-06-14 2018-08-14 Wisconsin Alumni Research Foundation 3-desoxy-2-methylene-19-nor-vitamin d analogs and their uses
WO2013003307A1 (en) 2011-06-28 2013-01-03 Wisconsin Alumni Research Foundation 2-methylene-(22e)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-vitamin d analogs
WO2013012644A1 (en) 2011-07-18 2013-01-24 Wisconsin Alumni I Research Foundation 2-methylene-20(21)-dehydro-19,24,25,26,27,-pentanor-vitamin d analogs
AU2012326538B2 (en) * 2011-10-21 2016-12-08 Wisconsin Alumni Research Foundation 2-methylene-vitamin D analogs and their uses
JP6114292B2 (ja) * 2011-10-21 2017-04-12 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
US8729054B2 (en) 2011-10-21 2014-05-20 Wisconsin Alumni Research Foundation 3-desoxy-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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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5726272B2 (da) * 1974-01-11 1982-06-03
JPS5726273B2 (da) * 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
ATE41924T1 (de) 1989-04-15
JPS61267549A (ja) 1986-11-27
CA1330806C (en) 1994-07-19
JPH0623185B2 (ja) 1994-03-30
DK161197C (da) 1991-11-25
EP0184206A3 (en) 1987-01-14
US4666634A (en) 1987-05-19
CN85108857A (zh) 1986-07-09
DE3569238D1 (en) 1989-05-11
DK561485A (da) 1986-06-06
KR940002981B1 (ko) 1994-04-09
DK561485D0 (da) 1985-12-04
EP0184206A2 (en) 1986-06-11
IL77122A0 (en) 1986-04-29
DK161197B (da) 1991-06-10
CN1008368B (zh) 1990-06-13
KR860004850A (ko) 1986-07-14
EP0184206B1 (en) 1989-04-05

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