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

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Obesity (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Diabetes (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Nutrition Science (AREA)
  • Endocrinology (AREA)
  • Rheumatology (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
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.
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
WO1996022973A1 (fr) * 1995-01-23 1996-08-01 Chugai Seiyaku Kabushiki Kaisha Derives de vitamine d3 de 2-substitution
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
US6392071B1 (en) 1997-03-17 2002-05-21 Wisconsin Alumni: Research Foundation 26,27-homologated-20-EPI-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
US5843928A (en) * 1997-03-17 1998-12-01 Wisconsin Alumni Research Foundation 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
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
WO1999052863A1 (fr) 1998-04-10 1999-10-21 Chugai Seiyaku Kabushiki Kaisha DERIVES DE LA VITAMINE D SUBSTITUES A LA POSITION 2$g(b)
US6114317A (en) * 1998-05-21 2000-09-05 Wisconsin Alumni Research Foundation Method of locking 1α-OH of vitamin D compounds in axial orientation
HK1042337A1 (en) * 1999-02-18 2002-08-09 Chugai Seiyaku Kabushiki Kaisha Method for screening compound having affinity for vitamin d receptor
AU2001256791A1 (en) * 2000-05-23 2001-12-03 Chugai Seiyaku Kabushiki Kaisha 5,6-trans-2-alkylvitamin d derivatives
ES2309069T3 (es) 2000-05-31 2008-12-16 Wisconsin Alumni Research Foundation Compuestos de 2-etil y 2-etiliden-19-nor-vitamina d.
CN100469764C (zh) * 2000-06-15 2009-03-18 中外制药株式会社 维生素d衍生物
BR0112454A (pt) * 2000-07-14 2003-07-29 Wisconsin Alumni Res Found Métodos de tratamento de doença metabólica do osso, psorìase, leucemia, câncer do cólon, do seio ou da próstata e de aumento da força de um osso e uso de composto
US20040030167A1 (en) * 2000-08-08 2004-02-12 Hiroaki Takayama 3-Methyl-20-epi-vitamin d derivatives
BR0113703A (pt) 2000-09-08 2003-07-22 Wisconsin Alumni Researcg Foun Compostos e métodos de tratamento de psorìase, leucemia, câncer do cólon, do seio ou da próstata, osteodistrofia renal, de doenças auto-imune, inflamatória e de condição de pele
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
HK1079766B (zh) * 2002-03-29 2007-05-25 威斯康星校友研究基金会 合成1α-羟基-2-亚甲基-19-去甲-高孕钙化醇的方法
JPWO2004012743A1 (ja) * 2002-08-01 2006-09-21 中外製薬株式会社 乾癬治療剤
KR101092277B1 (ko) * 2003-01-30 2011-12-13 데이진 화-마 가부시키가이샤 비타민 ｄ3 락톤 유도체
KR20050120787A (ko) * 2003-04-10 2005-12-23 위스콘신 얼럼나이 리서어치 화운데이션 2-프로필리덴-19-노르-비타민 ｄ 화합물
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
ATE537834T1 (de) * 2003-08-20 2012-01-15 Wisconsin Alumni Res Found 2-methylen-19-nor-vitamin d2-verbindungen
EP1714656B8 (de) * 2004-02-06 2017-09-20 Chugai Seiyaku Kabushiki Kaisha Ed-71-präparat
US7713951B2 (en) * 2004-04-09 2010-05-11 Wisconsin Alumni Research Foundation 2-alkylidene-18,19-dinor-vitamin D compounds
CA2588412A1 (en) * 2004-11-22 2006-06-01 Wisconsin Alumni Research Foundation 2alpha-methyl-19-nor-1alpha-hydroxy-homopregnacalciferol and its uses
AU2005309818A1 (en) * 2004-11-22 2006-06-01 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20R)-1-alpha-hydroxy-bishomopregnacalciferol
DE602005020842D1 (de) * 2004-11-22 2010-06-02 Wisconsin Alumni Res Found 17,20(e)-dehydro-vitamin-d-analoga und deren 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
ATE499942T1 (de) * 2004-11-22 2011-03-15 Wisconsin Alumni Res Found 2-methylen-19,21-dinor-1alpha-hydroxy- bishomopregnacalciferol
US7244719B2 (en) * 2004-11-22 2007-07-17 Wisconsin Alumni Research Foundation 2-methylene-19,26,27-trinor-(20S)-1α-hydroxyvitamin D3 and its uses
EP1848442B1 (de) * 2005-02-11 2012-04-25 Wisconsin Alumni Research Foundation 2-methylen-19-nor-(20s-24epi)-1alpha,25-dihydrovitamin-d2
CA2597624C (en) * 2005-02-11 2012-08-14 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20s-24s)-1.alpha.,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
EP1877063A4 (de) * 2005-05-03 2009-11-04 Wisconsin Alumni Res Found 19,26,27-trinor-1alpha ,25-dihydroxyvitamin-d3-verbindungen
ES2533719T3 (es) * 2005-08-30 2015-04-14 Wisconsin Alumni Research Foundation Análogos Des-C,D de 1alfa,25-dihidroxi-19-norvitamina D3
EP1940415A4 (de) * 2005-09-22 2010-03-17 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
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
MX2008012673A (es) * 2006-04-06 2008-10-15 Wisconsin Alumni Res Found Analogos de 2-metilen-1a-hidroxi-19, 21-dinorvitamina d3 y sus usos.
EP2021320A2 (de) 2006-04-06 2009-02-11 Wisconsin Alumni Research Foundation 2-substituierte 1-alpha-25-dihydroxy-19,26,27-trinor-vitamin-d-analoge und deren anwendungen
AU2007291005A1 (en) * 2006-04-06 2008-03-06 Wisconsin Alumni Research Foundation 19-nor-vitamin D analogs with 1,2,or 3,2 heterocyclic ring
AU2007234717B2 (en) * 2006-04-06 2012-04-19 Wisconsin Alumni Research Foundation 2-methylene-1alpha,25-dihydroxy-19,21-dinorvitamin D3 analogs and uses thereof
US8575136B2 (en) * 2006-04-06 2013-11-05 Wisconsin Alumni Research Foundation 2-methylene-1α-hydroxy-18,19,21-trinorvitamin D3 analogs and uses thereof
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.
ATE496885T1 (de) * 2006-04-10 2011-02-15 Wisconsin Alumni Res Found 1-alpha-hydroxy-2-(3'-hydroxypropyliden)-19-nor vitamin-d-verbindungen mit einer 1,1- dimethylpropyl-seitenkette
EP2069297A1 (de) * 2006-09-28 2009-06-17 Wisconsin Alumni Research Foundation 2-methylen-(20r,25s)-19,27-dinor-(22e)-vitamin-d-analoga
CA2662864A1 (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
US8609643B2 (en) * 2007-12-28 2013-12-17 Wisconsin Alumni Research Foundation 2-methylene-(20S,25R)-19,26-dinor-vitamin D analogs
AU2008345082B2 (en) * 2007-12-28 2014-03-06 Wisconsin Alumni Research Foundation (20S)-23,23-difluoro-2-methylene-19-nor-bishomopregnacalciferol-vitamin D analogs
ES2387714T3 (es) * 2007-12-28 2012-09-28 Wisconsin Alumni Research Foundation Análogos de 2-metilen-20-metil-19,24,25,26,27-pentanor-vitamina D
WO2009086439A2 (en) * 2007-12-28 2009-07-09 Wisconsin Alumni Research Foundation 2-methylene-(20s,25s)-19,26-dinor-vitamin d analogs
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
US8222236B2 (en) * 2008-07-10 2012-07-17 Wisconsin Alumni Research Foundation 2-methylene-(20E)-20(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
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
US7888339B2 (en) * 2008-07-10 2011-02-15 Wisconsin Alumni Research Foundation 2-methylene-20(21)-dehydro-19-nor-vitamin D analogs
MX2012003883A (es) 2009-10-02 2012-06-27 Wisconsin Alumni Res Found Analogos de (20s,22e)-2-metileno-19-nor-22-ene-1a,25-dihidroxovita mina d3.
WO2011041590A2 (en) 2009-10-02 2011-04-07 Wisconsin Alumni Research Foundation 1-desoxy-2-methylene-19-nor-vitamin d analogs and their uses
US8349818B2 (en) * 2009-10-21 2013-01-08 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
WO2012166938A2 (en) 2011-06-03 2012-12-06 Wisconsin Alumni Research Foundation (22e)-2-methylene-26,27-cyclo-22-dehydro-1alpha-hydroxy-19-norvitamin d3 derivatives
US8993547B2 (en) 2011-06-14 2015-03-31 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
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
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
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
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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
KR860004850A (ko) 1986-07-14
IL77122A (en) 1990-11-29
CN85108857A (zh) 1986-07-09
EP0184206B1 (de) 1989-04-05
US4666634A (en) 1987-05-19
DK561485A (da) 1986-06-06
DK161197C (da) 1991-11-25
JPS61267549A (ja) 1986-11-27
DE3569238D1 (en) 1989-05-11
IL77122A0 (en) 1986-04-29
CN1008368B (zh) 1990-06-13
DK561485D0 (da) 1985-12-04
CA1330806C (en) 1994-07-19
KR940002981B1 (ko) 1994-04-09
EP0184206A2 (de) 1986-06-11
EP0184206A3 (en) 1987-01-14
DK161197B (da) 1991-06-10
JPH0623185B2 (ja) 1994-03-30

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