CO4770966A1 - Sintesis enantioselectiva de azetidinonas a base de 3-hidro- xigamalactonas - Google Patents

Sintesis enantioselectiva de azetidinonas a base de 3-hidro- xigamalactonas

Info

Publication number
CO4770966A1
CO4770966A1 CO97029256A CO97029256A CO4770966A1 CO 4770966 A1 CO4770966 A1 CO 4770966A1 CO 97029256 A CO97029256 A CO 97029256A CO 97029256 A CO97029256 A CO 97029256A CO 4770966 A1 CO4770966 A1 CO 4770966A1
Authority
CO
Colombia
Prior art keywords
xigamalactones
azetidinones
hydro
enantioselective synthesis
formula
Prior art date
Application number
CO97029256A
Other languages
English (en)
Inventor
Guang-Zhong Wu
Xing Chen
Yee-Shing Wong
Doris P Schumacher
Martin Steinman
Original Assignee
Schering Corp
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 Schering Corp filed Critical Schering Corp
Publication of CO4770966A1 publication Critical patent/CO4770966A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • 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
    • A61P3/06—Antihyperlipidemics

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Obesity (AREA)
  • Diabetes (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Steroid Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La invención se relaciona con un proceso para producir uncompuesto de la fórmula I, en la cual R1 , R2 y R3 son tal como se definen en la memoria descriptiva, que comprende reaccionar una lactona con una imina para obtener un diol quiral de la fórmula, oxidando el diol, condensando el aldehido resultante con un enoléter, hidrogenando el producto, y reduciendo catalíticamente y quiralmente la cetona resultante.
CO97029256A 1996-05-31 1997-05-28 Sintesis enantioselectiva de azetidinonas a base de 3-hidro- xigamalactonas CO4770966A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US08/655,785 US5739321A (en) 1996-05-31 1996-05-31 3-hydroxy γ-lactone based enantionselective synthesis of azetidinones

Publications (1)

Publication Number Publication Date
CO4770966A1 true CO4770966A1 (es) 1999-04-30

Family

ID=24630339

Family Applications (1)

Application Number Title Priority Date Filing Date
CO97029256A CO4770966A1 (es) 1996-05-31 1997-05-28 Sintesis enantioselectiva de azetidinonas a base de 3-hidro- xigamalactonas

Country Status (14)

Country Link
US (1) US5739321A (es)
EP (1) EP0906278B1 (es)
JP (1) JP3155759B2 (es)
AR (1) AR007314A1 (es)
AT (1) ATE226191T1 (es)
AU (1) AU3299497A (es)
CA (1) CA2255662C (es)
CO (1) CO4770966A1 (es)
DE (1) DE69716426T2 (es)
DK (1) DK0906278T3 (es)
ES (1) ES2185026T3 (es)
PT (1) PT906278E (es)
WO (1) WO1997045406A1 (es)
ZA (1) ZA974678B (es)

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US20060287254A1 (en) * 2001-01-26 2006-12-21 Schering Corporation Use of substituted azetidinone compounds for the treatment of sitosterolemia
CA2442219C (en) * 2001-03-28 2007-09-11 Schering Corporation Enantioselective synthesis of azetidinone intermediate compounds
ATE345793T1 (de) * 2001-09-21 2006-12-15 Schering Corp Behandlung von xanthom mittels azetidinon- derivate als hemmer der sterol absorption
US20030204096A1 (en) * 2002-03-25 2003-10-30 Schering Corporation Enantioselective synthesis of azetidinone intermediate compounds
US7176193B2 (en) 2002-06-19 2007-02-13 Sanofi-Aventis Deutschland Gmbh Acid-group-substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use
US7671047B2 (en) 2002-06-19 2010-03-02 Sanofi-Aventis Deutschland Gmbh Cationically substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use
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US7135556B2 (en) * 2002-07-19 2006-11-14 Schering Corporation NPC1L1 (NPC3) and methods of use thereof
ATE406364T1 (de) * 2003-03-07 2008-09-15 Schering Corp Substituierte azetidinon-derivate, deren pharmazeutische formulierungen und deren verwendung zur behandlung von hypercholesterolemia
US7459442B2 (en) * 2003-03-07 2008-12-02 Schering Corporation Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof
ES2318274T3 (es) * 2003-03-07 2009-05-01 Schering Corporation Compuestos de azetidinona sustituida, formulaciones y uso de los mismos para el tratamiento de hipercolesterolemia.
AR041089A1 (es) 2003-05-15 2005-05-04 Merck & Co Inc Procedimiento y composiciones farmaceutiicas para tratar aterosclerosis, dislipidemias y afecciones relacionadas
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GB0329778D0 (en) * 2003-12-23 2004-01-28 Astrazeneca Ab Chemical compounds
BRPI0418004A (pt) * 2003-12-23 2007-04-17 Astrazeneca Ab composto ou um sal, solvato, solvato de um tal sal ou uma pró-droga deste farmaceuticamente aceitáveis, métodos para tratar ou prevenir condições hiperlipidêmicas, aterosclerose, mal de alzheimer, e tumores associados com colesterol, formulação farmacêutica, combinação, e, processo para preparar um composto ou um sal, solvato, solvato de um tal sal ou uma pró-droga deste farmaceuticamente aceitáveis
JP4590417B2 (ja) * 2004-01-16 2010-12-01 メルク・シャープ・エンド・ドーム・コーポレイション Ｎｐｃ１ｌ１（ｎｐｃ３）およびこのリガンドの同定方法
US20060211752A1 (en) 2004-03-16 2006-09-21 Kohn Leonard D Use of phenylmethimazoles, methimazole derivatives, and tautomeric cyclic thiones for the treatment of autoimmune/inflammatory diseases associated with toll-like receptor overexpression
US20070244107A1 (en) * 2004-08-25 2007-10-18 Waters M Gerard Method of Treating Atherosclerosis, Dyslipidemias and Related Conditions
US20060160785A1 (en) * 2004-12-03 2006-07-20 Judith Aronhime Ezetimibe polymorphs
US20060234996A1 (en) * 2005-04-14 2006-10-19 Itai Adin Novel crystalline form of ezetimibe and processes for the preparation thereof
ES2337727T3 (es) * 2005-06-20 2010-04-28 Schering Corporation Derivados de piperidina utiles como antagonistas de histamina h3.
SA06270191B1 (ar) * 2005-06-22 2010-03-29 استرازينيكا ايه بي مشتقات من 2- أزيتيدينون جديدة باعتبارها مثبطات لامتصاص الكوليسترول لعلاج حالات فرط نسبة الدهون في الدم
AR054482A1 (es) * 2005-06-22 2007-06-27 Astrazeneca Ab Derivados de azetidinona para el tratamiento de hiperlipidemias
US20070049748A1 (en) * 2005-08-26 2007-03-01 Uppala Venkata Bhaskara R Preparation of ezetimibe
CA2616058A1 (en) * 2005-09-08 2007-03-15 Vinod Kumar Kansal Processes for the preparation of (3r,4s)-4-((4-benzyloxy)phenyl)-1-(4-fluorophenyl)-3-((s)-3-(4-fluorophenyl)-3-hydroxypropyl)-2-azetidinone, an intermediate for the synthesis of ezetimibe
WO2007048027A2 (en) 2005-10-21 2007-04-26 Novartis Ag Combination of a renin-inhibitor and an anti-dyslipidemic agent and/or an antiobesity agent
HU0501164D0 (en) * 2005-12-20 2006-02-28 Richter Gedeon Vegyeszet New industrial process for the production of ezetimibe
US20090227786A1 (en) * 2005-12-22 2009-09-10 Ana Gavalda I Escude Processes for preparing intermediate compounds useful for the preparation of ezetimibe
WO2007100807A2 (en) 2006-02-24 2007-09-07 Schering Corporation Npc1l1 orthologues
WO2007108007A1 (en) * 2006-03-23 2007-09-27 Unichem Laboratories Limited A process for the preparation of ezetimibe via a novel intermediate
EP2007718A2 (en) * 2006-03-29 2008-12-31 Medichem, S.A. Processes for preparing ezetimibe and intermediate compounds useful for the preparation thereof
AR060623A1 (es) * 2006-04-27 2008-07-02 Astrazeneca Ab Compuestos derivados de 2-azetidinona y un metodo de preparacion
WO2008027081A1 (en) * 2006-08-29 2008-03-06 Teva Pharmaceutical Industries Ltd. Processes for the purification of (3r,4s)-4-(4-hydroxy-protected-phenyl)-1-(4-fluorophenyl)-3-(4-fluorophenyl)-3-oxopropyl] azetidin-2-one
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DE102007063671A1 (de) 2007-11-13 2009-06-25 Sanofi-Aventis Deutschland Gmbh Neue kristalline Diphenylazetidinonhydrate, diese Verbindungen enthaltende Arzneimittel und deren Verwendung
CZ305066B6 (cs) * 2008-02-25 2015-04-22 Zentiva, K.S. Způsob výroby (3R,4S)-1-(4-fluorfenyl)-3-[(3S)-3-(4-fluorfenyl)-3-hydroxypropyl)]-4-(4-hydroxyfenyl)-2-azetidinonu
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PL387331A1 (pl) * 2009-02-24 2010-08-30 Instytut Chemii Organicznej Polskiej Akademii Nauk Sposób wytwarzania aldehydowego związku beta-laktamowego, związek pośredni, sposób wytwarzania związku pośredniego oraz zastosowanie związku pośredniego
WO2010113175A2 (en) 2009-04-01 2010-10-07 Matrix Laboratories Ltd Enzymatic process for the preparation of (s)-5-(4-fluoro-phenyl)-5-hydroxy- 1morpholin-4-yl-pentan-1-one, an intermediate of ezetimibe and further conversion to ezetimibe
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CN102477008B (zh) * 2010-11-22 2014-05-21 沈阳药科大学 依泽替米贝的合成方法
WO2012076030A1 (en) * 2010-12-10 2012-06-14 Pharmathen S.A. Process for the preparation of intermediate compounds useful in the preparation of ezetimibe
WO2012155932A1 (en) 2011-05-17 2012-11-22 Pharmathen S.A. Improved process for the preparation of ezetimibe
PL231215B1 (pl) 2011-06-15 2019-02-28 Inst Chemii Organicznej Polskiej Akademii Nauk Sposób wytwarzania podstawionych azetydynonów oraz związków pośrednich do ich syntezy
CN103086938A (zh) * 2011-10-28 2013-05-08 沈阳药科大学 依泽替米贝的合成方法
CN102531986A (zh) * 2012-02-23 2012-07-04 苏州朗科生物技术有限公司 一种依替米贝的制备方法
CN103570574B (zh) 2012-07-20 2016-04-13 中国科学院上海有机化学研究所 一种依泽替米贝的合成方法及该方法中所用的中间体
CN103044305A (zh) * 2013-01-24 2013-04-17 上海现代制药股份有限公司 一种依折麦布中间体的制备方法
WO2015039675A1 (en) 2013-09-23 2015-03-26 Pharmathen S.A. Novel process for the preparation of ezetimibe intermediates
CN103739537B (zh) * 2013-12-24 2015-05-20 连云港恒运医药科技有限公司 依折麦布的新合成方法
CN104072398B (zh) * 2014-07-03 2016-02-03 河南省科学院化学研究所有限公司 一种合成依折麦布的方法
JP2016145173A (ja) * 2015-02-09 2016-08-12 株式会社トクヤマ （３ｒ，４ｓ）‐１‐（４‐フルオロフェニル）‐［３（ｓ）‐ヒドロキシ‐３‐（４‐フルオロフェニル）プロピル］‐（４‐ヒドロキシフェニル）‐２‐アゼチジノンの製造方法
CN107098841A (zh) * 2016-02-19 2017-08-29 常州方楠医药技术有限公司 一种依折麦布的制备方法及该方法中所用的中间体
CN107033051A (zh) * 2017-06-08 2017-08-11 武汉励合生物医药科技有限公司 一种依泽替米贝的制备方法

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US5631365A (en) * 1993-09-21 1997-05-20 Schering Corporation Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents
AU7472896A (en) * 1995-11-02 1997-05-22 Schering Corporation Process for preparing 1-(4-fluorophenyl)-3(r)-(3(s)-hydroxy-3-({phenyl or 4-fluorophenyl})-propyl)-4(s)-(4-hydroxyphenyl)-2-azetidinon

Also Published As

Publication number Publication date
ZA974678B (en) 1997-11-28
PT906278E (pt) 2003-01-31
EP0906278B1 (en) 2002-10-16
CA2255662A1 (en) 1997-12-04
JP3155759B2 (ja) 2001-04-16
DE69716426D1 (de) 2002-11-21
CA2255662C (en) 2005-11-08
US5739321A (en) 1998-04-14
DK0906278T3 (da) 2003-02-17
EP0906278A1 (en) 1999-04-07
ES2185026T3 (es) 2003-04-16
AR007314A1 (es) 1999-10-27
JPH11511754A (ja) 1999-10-12
DE69716426T2 (de) 2003-08-14
ATE226191T1 (de) 2002-11-15
WO1997045406A1 (en) 1997-12-04
AU3299497A (en) 1998-01-05

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