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WO2005066120A3 - Procede de synthese asymetrique de derives azetidinone hydroxy-alkyle-substitues ou de leurs intermediaires - Google Patents

Procede de synthese asymetrique de derives azetidinone hydroxy-alkyle-substitues ou de leurs intermediaires Download PDF

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Publication number
WO2005066120A3
WO2005066120A3 PCT/IB2004/004281 IB2004004281W WO2005066120A3 WO 2005066120 A3 WO2005066120 A3 WO 2005066120A3 IB 2004004281 W IB2004004281 W IB 2004004281W WO 2005066120 A3 WO2005066120 A3 WO 2005066120A3
Authority
WO
WIPO (PCT)
Prior art keywords
asymmetric synthesis
hydroxy
alkyl substituted
substituted azetidinone
azetidinone derivatives
Prior art date
Application number
PCT/IB2004/004281
Other languages
English (en)
Other versions
WO2005066120A2 (fr
Inventor
Yatendra Kumar
Hashim Nizar Poovanathi Meeran
Shailendra Kumar Singh
Parendu Dhirajlal Rathod
Kiran Kumar Ganagakhedkar
Prosenjit Bose
Pramod Kumar
Original Assignee
Ranbaxy Lab Ltd
Yatendra Kumar
Hashim Nizar Poovanathi Meeran
Shailendra Kumar Singh
Parendu Dhirajlal Rathod
Kiran Kumar Ganagakhedkar
Prosenjit Bose
Pramod Kumar
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 Ranbaxy Lab Ltd, Yatendra Kumar, Hashim Nizar Poovanathi Meeran, Shailendra Kumar Singh, Parendu Dhirajlal Rathod, Kiran Kumar Ganagakhedkar, Prosenjit Bose, Pramod Kumar filed Critical Ranbaxy Lab Ltd
Publication of WO2005066120A2 publication Critical patent/WO2005066120A2/fr
Publication of WO2005066120A3 publication Critical patent/WO2005066120A3/fr

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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procédés de synthèse asymétrique de dérivés azétidinone hydroxy-alkyle-substitués ou de leurs intermédiaires par réduction stéréosélective de cétone benzylique à l'aide de (-)-B-chlorodiisopinocampheylborane. On a également prévu des procédés de préparation d'ézétimibe.
PCT/IB2004/004281 2003-12-30 2004-12-23 Procede de synthese asymetrique de derives azetidinone hydroxy-alkyle-substitues ou de leurs intermediaires WO2005066120A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1643/DEL/2003 2003-12-30
IN1643DE2003 2003-12-30

Publications (2)

Publication Number Publication Date
WO2005066120A2 WO2005066120A2 (fr) 2005-07-21
WO2005066120A3 true WO2005066120A3 (fr) 2008-01-17

Family

ID=34746661

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2004/004281 WO2005066120A2 (fr) 2003-12-30 2004-12-23 Procede de synthese asymetrique de derives azetidinone hydroxy-alkyle-substitues ou de leurs intermediaires

Country Status (1)

Country Link
WO (1) WO2005066120A2 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0215579D0 (en) 2002-07-05 2002-08-14 Astrazeneca Ab Chemical compounds
DE602004029715D1 (de) 2003-12-23 2010-12-02 Astrazeneca Ab Diphenylazetidinonderivate mit die cholesterinabsorption hemmender wirkung
UY29607A1 (es) 2005-06-20 2007-01-31 Astrazeneca Ab Compuestos quimicos
AR057072A1 (es) 2005-06-22 2007-11-14 Astrazeneca Ab Compuestos quimicos derivados de 2-azetidinona, formulacion farmaceutica y un proceso de preparacion del compuesto
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
HUP0501164A2 (en) 2005-12-20 2007-07-30 Richter Gedeon Nyrt New industrial process for the production of ezetimibe
US7956182B2 (en) 2006-02-16 2011-06-07 Kotobuki Pharmaceutical Co., Ltd. Process for preparing optically active alcohols
TW200811098A (en) 2006-04-27 2008-03-01 Astrazeneca Ab Chemical compounds
US9388440B2 (en) 2009-04-01 2016-07-12 Mylan Laboratories Limited 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
CN107488173B (zh) * 2016-06-10 2021-05-04 山东新时代药业有限公司 一种依折麦布中间体及其合成方法
CN108586373A (zh) * 2018-06-22 2018-09-28 苏州市贝克生物科技有限公司 依折麦布中间体的合成方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5856473A (en) * 1995-11-02 1999-01-05 Schering Corporation Process for preparing 1-(4-fluorophenyl)-3(R)-(3(S)-hydroxy-3-( phenyl or 4-fluorophenyl!)-propyl)-4(S)-(4-hydroxyphenyl)-2-azetidinone
WO2005049592A1 (fr) * 2003-11-24 2005-06-02 Hetero Drugs Limited Nouveau procede de preparation d'intermediaire d'ezetimibe

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5856473A (en) * 1995-11-02 1999-01-05 Schering Corporation Process for preparing 1-(4-fluorophenyl)-3(R)-(3(S)-hydroxy-3-( phenyl or 4-fluorophenyl!)-propyl)-4(S)-(4-hydroxyphenyl)-2-azetidinone
WO2005049592A1 (fr) * 2003-11-24 2005-06-02 Hetero Drugs Limited Nouveau procede de preparation d'intermediaire d'ezetimibe

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEN ET AL.: "Asymetric Synthesis of Substituted 2-Azaspiro[3.5]nonan-1-ones: An Enantioselective Synthesis of the Cholesterol Absorption Inhibitor (+)-SCH 54016", JOURNAL OF ORGANIC CHEMISTRY, vol. 61, 1996, pages 8341 - 8343, XP002335913 *
FU X ET AL: "Process for preparing Ezetimibe intermediate by an acid enhanced chemo- and enantioselective CBS catalyzed ketone reduction", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 44, no. 4, 20 January 2003 (2003-01-20), pages 801 - 804, XP004405139, ISSN: 0040-4039 *
RAMACHANDRAN ET AL.: "Selective reductions", JOURNAL OF ORGANIC CHEMISTRY, vol. 67, 2002, pages 5315 - 5319, XP002327477 *
WU G ET AL: "A NOVEL ONE-STEP DIASTEREO- AND ENANTIOSELECTIVE FORMATION OF TRANS-AZETIDINONES AND ITS APPLICATION TO THE TOTAL SYNTHESIS OF CHOLESTEROL ABSORPTION INHIBITORS", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 64, 1999, pages 3714 - 3718, XP002296009, ISSN: 0022-3263 *

Also Published As

Publication number Publication date
WO2005066120A2 (fr) 2005-07-21

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