DK161197C - 1alfa-hydroxy-2-substituerede vitamin d3 derivater samt fremgangsmaade til fremstilling af disse - Google Patents

1alfa-hydroxy-2-substituerede vitamin d3 derivater samt fremgangsmaade til fremstilling af disse

Info

Publication number
DK161197C
DK161197C DK561485A DK561485A DK161197C DK 161197 C DK161197 C DK 161197C DK 561485 A DK561485 A DK 561485A DK 561485 A DK561485 A DK 561485A DK 161197 C DK161197 C DK 161197C
Authority
DK
Denmark
Prior art keywords
group
hydroxy
1alfa
procedures
derivatives
Prior art date
Application number
DK561485A
Other languages
Danish (da)
English (en)
Other versions
DK561485D0 (da
DK561485A (da
DK161197B (da
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
Publication of DK561485D0 publication Critical patent/DK561485D0/da
Publication of DK561485A publication Critical patent/DK561485A/da
Publication of DK161197B publication Critical patent/DK161197B/da
Application granted granted Critical
Publication of DK161197C publication Critical patent/DK161197C/da

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)
DK561485A 1984-12-05 1985-12-04 1alfa-hydroxy-2-substituerede vitamin d3 derivater samt fremgangsmaade til fremstilling af disse DK161197C (da)

Applications Claiming Priority (2)

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

Publications (4)

Publication Number Publication Date
DK561485D0 DK561485D0 (da) 1985-12-04
DK561485A DK561485A (da) 1986-06-06
DK161197B DK161197B (da) 1991-06-10
DK161197C true DK161197C (da) 1991-11-25

Family

ID=17282605

Family Applications (1)

Application Number Title Priority Date Filing Date
DK561485A DK161197C (da) 1984-12-05 1985-12-04 1alfa-hydroxy-2-substituerede vitamin d3 derivater samt fremgangsmaade til fremstilling af disse

Country Status (10)

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

Families Citing this family (89)

* Cited by examiner, † Cited by third party
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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.
JP2898882B2 (ja) * 1993-04-05 1999-06-02 ウイスコンシン アラムナイ リサーチ フオンデーシヨン ２−位に置換基を有する１９−ノル−ビタミンｄ３ 化合物
ES2169220T3 (es) * 1995-01-23 2002-07-01 Chugai Pharmaceutical Co Ltd Derivados de vitamina d3 con sustituyentes en la posicion 2.
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
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
US6316642B1 (en) * 1997-03-17 2001-11-13 Wisconsin Alumni Research Foundation 26,27-Homologated-20-EPI-2alkyl-19-nor-vitamin D compounds
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
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
US6410523B1 (en) 1998-04-10 2002-06-25 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
CA2362071A1 (en) * 1999-02-18 2000-08-24 Chugai Seiyaku Kabushiki Kaisha Method for screening compound having affinity for vitamin d receptor
WO2001090061A1 (fr) * 2000-05-23 2001-11-29 Chugai Seiyaku Kabushiki Kaisha Derives de 5, 6-trans-2-alkylevitamine d
IL152942A (en) * 2000-05-31 2007-09-20 Wisconsin Alumni Res Found Compounds 2 - Ethyl and 2 - Ethylaidine - 19 - Nur - Vitamin D and pharmaceutical preparations containing them
CA2664720C (en) * 2000-06-15 2011-11-22 Chugai Seiyaku Kabushiki Kaisha Vitamin d derivatives
AU7888801A (en) * 2000-07-14 2002-01-30 Wisconsin Alumni Res Found Use of 2-methylene-19-nor-20(s)-1alpha,25-dihydroxyvitamin D<sub>3</sub> to increase bone strength
US20040030167A1 (en) * 2000-08-08 2004-02-12 Hiroaki Takayama 3-Methyl-20-epi-vitamin d derivatives
ATE273709T1 (de) 2000-09-08 2004-09-15 Wisconsin Alumni Res Found 1alpha-hydroxy-2-methylene-19-nor- homopregnacalciferol und seine therapeutische verwendungen
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
JP3957303B2 (ja) * 2002-03-29 2007-08-15 ウィスコンシン・アルムニ・リサーチ・ファウンデーション １α−ヒドロキシ−２−メチレン−１９−ノル−ホモプレグナカルシフェロールの合成法
AU2003252332A1 (en) * 2002-08-01 2004-02-23 Chugai Seiyaku Kabushiki Kaisha Antipsoriatic agent
AU2004207719B9 (en) * 2003-01-30 2009-10-01 Teijin Limited Vitamin D3 lactone derivative
ATE556999T1 (de) * 2003-04-10 2012-05-15 Wisconsin Alumni Res Found 2-propyliden-19-nor-vitamin d verbindungen
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
NZ545862A (en) * 2003-08-20 2010-01-29 Wisconsin Alumni Res Found 2-Methylene-19-nor-vitamin D2 compounds
US20070129340A1 (en) * 2004-02-06 2007-06-07 Chugai Seiyaku Kabushiki Kaisha Ed-71 preparation
US7713951B2 (en) * 2004-04-09 2010-05-11 Wisconsin Alumni Research Foundation 2-alkylidene-18,19-dinor-vitamin D compounds
DE602005021538D1 (de) * 2004-11-22 2010-07-08 Wisconsin Alumni Res Found 17,20(z)-dehydro-vitamin-d-analoge und deren verwendungen
MX2007006094A (es) * 2004-11-22 2007-07-11 Wisconsin Alumni Res Found 2-metilen-19,21-dinor-1a-hidroxi-bishomopregnacalciferol.
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
MX2007006545A (es) * 2004-11-22 2007-09-21 Wisconsin Alumni Res Found 2a-metil-19-nor-1a-hidroxi-homopregnacalciferol y sus usos.
AU2005309818A1 (en) * 2004-11-22 2006-06-01 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20R)-1-alpha-hydroxy-bishomopregnacalciferol
CA2588060A1 (en) * 2004-11-22 2006-06-01 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20s)-1alpha-hydroxy-trishomopregnacalciferol
US7563783B2 (en) * 2005-02-11 2009-07-21 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20S-24S)-1α,25-dihydroxyvitamin-D2
ATE554774T1 (de) * 2005-02-11 2012-05-15 Wisconsin Alumni Res Found 2-methylen-19-nor-(20s-24epi)-1alpha,25- dihydrovitamin-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
NZ563758A (en) * 2005-05-03 2010-04-30 Wisconsin Alumni Res Found 19,26,27-Trinor-1alpha,25-dihydroxyvitamin D3 compounds
NZ567015A (en) * 2005-08-30 2010-12-24 Wisconsin Alumni Res Found Des-C,D analogs of 1alpha,25-dihydroxy-19-norvitamin D3
CA2623481A1 (en) * 2005-09-22 2007-04-05 Wisconsin Alumni Research Foundation 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
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
US8058265B2 (en) * 2006-04-05 2011-11-15 Wisconsin Alumni Research Foundation 1a-hydroxy-2-(3'-hydroxypropylidene)-19-nor-vitamin D compounds and methods of making and treatment thereof
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
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
EP2001842B1 (en) * 2006-04-06 2012-06-06 Wisconsin Alumni Research Foundation 2-methylene-1alpha-hydroxy-19,21-dinorvitamin d3 analogs and uses thereof
JP2009532460A (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−置換−１α，２５−ジヒドロキシ−１９，２６，２７−トリノルビタミンＤ類縁体およびその使用
MX2008012913A (es) * 2006-04-06 2009-03-06 Wisconsin Alumni Res Found 2-metilen-1a,25-dihidroxi-18,19,21-trinorvitamina d3 y sus usos.
CA2648324A1 (en) * 2006-04-06 2007-10-18 Wisconsin Alumni Research Foundation 2-methylene-1.alpha.,25-dihydroxy-19,21-dinorvitamin d3 analogs and uses thereof
EP2004597B1 (en) * 2006-04-10 2011-01-26 Wisconsin Alumni Research Foundation 1alpha-hydroxy-2-(3'-hydroxypropylidene)-19-nor-vitamin d compounds with a 1,1-dimethylpropyl side chain
WO2008039751A2 (en) * 2006-09-28 2008-04-03 Wisconsin Alumni Research Foundation 2-methylene-(20s,25s)-19,27-dinor-(22e)-vitamin d analogs
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
CA2710966C (en) * 2007-12-28 2015-10-13 Wisconsin Alumni Research Foundation (20r)-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
JP2011507965A (ja) * 2007-12-28 2011-03-10 ウィスコンシン アラムナイ リサーチ ファンデーション ２−メチレン−（２０ｓ，２５ｓ）−１９，２６−ジノル−ビタミンｄ類縁体
JP2011508743A (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 （２０ｓ）−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
AU2008345086B2 (en) * 2007-12-28 2014-02-13 Wisconsin Alumni Research Foundation 2-methylene-20-methyl-19,24,25,26,27-pentanor-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
US8399439B2 (en) * 2008-07-10 2013-03-19 Wisconsin Alumni Research Foundation 2-methylene-19,26-dinor-(20S,22E,25R)-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
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
US8222236B2 (en) * 2008-07-10 2012-07-17 Wisconsin Alumni Research Foundation 2-methylene-(20E)-20(22)-dehydro-19-nor-vitamin D analogs
WO2011041579A2 (en) 2009-10-02 2011-04-07 Wisconsin Alumni Research Foundation (20S,22E)-2-METHYLENE-19-NOR-22-ENE-1α,25-DIHYDROXYVITAMIN D3 ANALOGS
CA2776464C (en) 2009-10-02 2017-10-24 Wisconsin Alumni Research Foundation 1-desoxy-2-methylene-19-nor-vitamin d analogs and their uses
EP2490695B1 (en) 2009-10-21 2013-11-20 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
US8754067B2 (en) 2010-11-12 2014-06-17 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
CA2837882C (en) 2011-06-03 2019-03-26 Wisconsin Alumni Research Foundation (22e)-2-methylene-26,27-cyclo-22-dehydro-1.alpha.-hydroxy-19-norvitamin d3 derivatives
EP2721004B1 (en) 2011-06-14 2017-07-26 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
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
EP2768804B1 (en) 2011-10-21 2018-02-28 Wisconsin Alumni Research Foundation 2-methylene-vitamin d analogs and their uses
US8455467B2 (en) 2011-10-21 2013-06-04 Wisconsin Alumni Research Foundation 2-methylene-vitamin D analogs and their uses
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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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
DE3569238D1 (en) 1989-05-11
DK561485D0 (da) 1985-12-04
KR940002981B1 (ko) 1994-04-09
KR860004850A (ko) 1986-07-14
JPS61267549A (ja) 1986-11-27
IL77122A (en) 1990-11-29
EP0184206B1 (en) 1989-04-05
DK561485A (da) 1986-06-06
CN85108857A (zh) 1986-07-09
CN1008368B (zh) 1990-06-13
JPH0623185B2 (ja) 1994-03-30
ATE41924T1 (de) 1989-04-15
US4666634A (en) 1987-05-19
IL77122A0 (en) 1986-04-29
EP0184206A3 (en) 1987-01-14
DK161197B (da) 1991-06-10
CA1330806C (en) 1994-07-19
EP0184206A2 (en) 1986-06-11

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