ES2083685T3 - Intermediarios para la sintesis de compuestos de la 19-nor-vitamina d. - Google Patents

Intermediarios para la sintesis de compuestos de la 19-nor-vitamina d.

Info

Publication number
ES2083685T3
ES2083685T3 ES92304838T ES92304838T ES2083685T3 ES 2083685 T3 ES2083685 T3 ES 2083685T3 ES 92304838 T ES92304838 T ES 92304838T ES 92304838 T ES92304838 T ES 92304838T ES 2083685 T3 ES2083685 T3 ES 2083685T3
Authority
ES
Spain
Prior art keywords
vitamin
compounds
synthesis
intermediaries
side chain
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
ES92304838T
Other languages
English (en)
Inventor
Hector Floyd Deluca
Heinrich Konstantine Schnoes
Kato Leonard Perlman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wisconsin Alumni Research Foundation
Original Assignee
Wisconsin Alumni Research Foundation
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 Wisconsin Alumni Research Foundation filed Critical Wisconsin Alumni Research Foundation
Application granted granted Critical
Publication of ES2083685T3 publication Critical patent/ES2083685T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/20Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/277Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/20Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/26Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C47/267Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups containing rings other than six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

COMPUESTOS INTERMEDIOS NUEVOS QUE SE PUEDEN UTILIZAR EFICAZMENTE PARA LA SINTESIS DE UNA AMPLIA GAMA DE COMPUESTOS DE 1O-HIDROXI-19-NOR VOS SE CARACTERIZAN POR UN GRUPO SELECCIONADO DE HIDROXI METILO (-CH2OH), CARBOXALDEHIDO (-CHO) Y ESTER DE CARBOXI (COOALQUILO) EN LA POSICION 22 DEL CARBONO DE LA CADENA LATERAL DE UN NUCLEO DE 19-NOR TIPO SON UTILES PARA LA INTRODUCCION DE UNIDADES DE CADENA LATERAL Y, POR LO TANTO, REPRESENTAN SINTONES IMPORTANTES PARA LA PREPARACION DE MUCHOS COMPUESTOS DISTINTOS DE 19-NOR VITAMINA D.
ES92304838T 1991-05-28 1992-05-28 Intermediarios para la sintesis de compuestos de la 19-nor-vitamina d. Expired - Lifetime ES2083685T3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US07/705,932 US5086191A (en) 1991-05-28 1991-05-28 Intermediates for the synthesis of 19-nor vitamin D compounds

Publications (1)

Publication Number Publication Date
ES2083685T3 true ES2083685T3 (es) 1996-04-16

Family

ID=24835525

Family Applications (1)

Application Number Title Priority Date Filing Date
ES92304838T Expired - Lifetime ES2083685T3 (es) 1991-05-28 1992-05-28 Intermediarios para la sintesis de compuestos de la 19-nor-vitamina d.

Country Status (8)

Country Link
US (1) US5086191A (es)
EP (1) EP0516411B1 (es)
JP (1) JP2668759B2 (es)
KR (1) KR0176979B1 (es)
AT (1) ATE134365T1 (es)
DE (1) DE69208395T2 (es)
DK (1) DK0516411T3 (es)
ES (1) ES2083685T3 (es)

Families Citing this family (120)

* Cited by examiner, † Cited by third party
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US5945410A (en) * 1997-03-17 1999-08-31 Wisconsin Alumni Research Foundation 2-alkyl-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
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AU2004266706B2 (en) 2003-08-20 2009-07-30 Wisconsin Alumni Research Foundation 2-methylene-19-nor-vitamin D2 compounds
WO2005027920A1 (en) * 2003-09-19 2005-03-31 Pfizer Products Inc. 2-alkylidene-19-nor-vitamin d derivatives for the treatment of rickets or vitamin d deficiency
NZ545393A (en) * 2003-09-19 2009-10-30 Wisconsin Alumni Res Found 2-Alkylidene-19-nor-vitamin D derivatives for the treatment of osteopenia or male osteoporosis
WO2005027925A1 (en) * 2003-09-19 2005-03-31 Pfizer Products Inc. 2-alkylidene-19-nor-vitamin d derivatives for the treatment of anorexia or low bone mass in females exhibiting aggressive athletic behavior
WO2005027914A1 (en) * 2003-09-19 2005-03-31 Pfizer Products Inc. 2-alkylidene-19-nor-vitamin d derivatives for the treatment of frailty, muscle damage or sarcopenia
KR20060058133A (ko) * 2003-09-19 2006-05-29 화이자 프로덕츠 인코포레이티드 2-알킬리덴-19-노르-비타민 d 유도체 및 부갑상선호르몬의 조합을 포함하는 약학 조성물 및 방법
CA2539361A1 (en) * 2003-09-19 2005-03-31 Pfizer Products Inc. Pharmaceutical compositions and methods comprising combinations of 2-alkylidene-19-nor-vitamin d derivatives and an estrogen agonist/antagonist
WO2005027916A1 (en) * 2003-09-19 2005-03-31 Pfizer Products Inc. Pharmaceutical compositions and methods comprising combinations of 2-alkylidene-19-nor-vitamin d derivatives and aromatase inhibitors
WO2005027927A1 (en) * 2003-09-19 2005-03-31 Pfizer Products Inc. 2-alkylidene-19-nor-vitamin d derivatives for enhancement of peak bone mass in adolescence
WO2005027926A1 (en) * 2003-09-19 2005-03-31 Pfizer Products Inc. Pharmaceutical compositions and methods comprising combinations of 2-alkylidene-19-nor-vitamin d derivatives and a bone morphogenetic protein
WO2005027929A1 (en) * 2003-09-19 2005-03-31 Pfizer Products Inc. Pharmaceutical compositions and methods comprising combinations of 2-alkylidene-19-nor-vitamin d derivatives and an estrogen
WO2005027921A1 (en) * 2003-09-19 2005-03-31 Pfizer Products Inc. Pharmaceutical compositions and methods comprising combinations of 2-alkylidene-19-nor-vitamin d derivatives and a bisphosphonate
WO2005027913A1 (en) * 2003-09-19 2005-03-31 Pfizer Products Inc. Pharmaceutical compositions and methods comprising combinations of 2-alkylidene-19-nor-vitamin d derivatives and a growth hormone secretagogue
WO2005027931A1 (en) * 2003-09-19 2005-03-31 Pfizer Products Inc. Pharmaceutical compositions and methods comprising combinations of 2-alkylidene-19-nor-vitamin d derivatives and an ep2 or ep4 selective agonist
US7053075B2 (en) 2003-11-25 2006-05-30 Deluca Hector F Methods for reducing body fat using vitamin D compounds
CA2544502A1 (en) * 2003-11-25 2005-06-09 Wisconsin Alumni Research Foundation Vitamin d analogs for obesity prevention and treatment
US7915242B2 (en) * 2004-02-17 2011-03-29 Wisconsin Alumni Research Foundation Vitamin D receptor antagonists and their use in treating asthma
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
US7541348B2 (en) * 2004-11-22 2009-06-02 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20S)-1α-hydroxy-trishomopregnacalciferol
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
EP1827452B1 (en) * 2004-11-22 2011-03-02 Wisconsin Alumni Research Foundation 2-methylene-19,21-dinor-1alpha-hydroxy-bishomopregnacalciferol
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
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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
EP1922303A2 (en) * 2005-07-18 2008-05-21 Teva Pharmaceutical Industries Ltd Purification of paricalcitol
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
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EP2010483A2 (en) * 2006-04-05 2009-01-07 Wisconsin Alumni Research Foundation 1.alpha.-hydroxy-2-(3'-hydroxypropylidene)-19-nor-vitamin d compounds and methods of making and use thereof
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US8193169B2 (en) * 2006-04-06 2012-06-05 Wisconsin Alumni Research Foundation (20R)-2α-methyl-19,26,2-trinor-vitamin D analogs
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US9040728B2 (en) * 2012-05-30 2015-05-26 Wisconsin Alumni Research Foundation Crystallization of (20R) 19-nor-24-difluoro-1α,25-dihydroxyvitamin D3
US8785422B2 (en) 2012-06-06 2014-07-22 Wisconsin Alumni Research Foundation A-ring modified 19-nor-vitamin D analogs and their uses
EP2746252A1 (en) 2012-12-21 2014-06-25 Wisconsin Alumni Research Foundation (WARF) Crystallization of 1alpha-hydroxy-2-methylene- 18,19-dinor-homopregnacalciferol
CN103086937A (zh) * 2013-01-08 2013-05-08 上海朴颐化学科技有限公司 合成帕立骨化醇的方法
US9416102B2 (en) 2013-01-23 2016-08-16 Wisconsin Alumni Research Foundation (22E)-2-methylene-22-dehydro-1α,24,25-trihydroxy-19-nor-vitamin D3 analogs
CN112156097A (zh) 2013-05-29 2021-01-01 博格有限责任公司 使用维生素d预防或减轻化疗诱发的脱发
CN103965087A (zh) * 2014-05-05 2014-08-06 湖南华腾制药有限公司 帕立骨化醇关键中间体的合成工艺
CN104558013B (zh) * 2015-01-29 2017-03-22 上海皓元生物医药科技有限公司 一种(z)‑2‑((3r,4r,5r)‑3,5‑双羟基‑4‑(3‑羟基‑丙氧基)‑2‑亚甲基环己基)乙醇的衍生物a的制备方法

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JP2668759B2 (ja) 1997-10-27
KR920021506A (ko) 1992-12-18
US5086191A (en) 1992-02-04
EP0516411A1 (en) 1992-12-02
KR0176979B1 (ko) 1999-05-15
JPH05186421A (ja) 1993-07-27
DE69208395T2 (de) 1996-06-27
EP0516411B1 (en) 1996-02-21

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