WO2012173504A3 - Method for synthesis of the substituted azetidinones and intermediates for their synthesis - Google Patents

Method for synthesis of the substituted azetidinones and intermediates for their synthesis Download PDF

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Publication number
WO2012173504A3
WO2012173504A3 PCT/PL2012/050022 PL2012050022W WO2012173504A3 WO 2012173504 A3 WO2012173504 A3 WO 2012173504A3 PL 2012050022 W PL2012050022 W PL 2012050022W WO 2012173504 A3 WO2012173504 A3 WO 2012173504A3
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WO
WIPO (PCT)
Prior art keywords
synthesis
intermediates
substituted azetidinones
azetidinones
substituted
Prior art date
Application number
PCT/PL2012/050022
Other languages
French (fr)
Other versions
WO2012173504A2 (en
Inventor
Marek Chmielewski
Sebastian Stecko
Bartłomiej FURMAN
Irma Panfil
Marcin ŚNIEŻEK
Michał MICHALAK
Margerita JURCZAK
Barbara GRZESZCZYK
Magdalena SOLUCH
Paulina MIKOŁAJCZYK
Original Assignee
Instytut Chemii Organicznej Polskiej Akademii Nauk
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 Instytut Chemii Organicznej Polskiej Akademii Nauk filed Critical Instytut Chemii Organicznej Polskiej Akademii Nauk
Publication of WO2012173504A2 publication Critical patent/WO2012173504A2/en
Publication of WO2012173504A3 publication Critical patent/WO2012173504A3/en

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    • 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
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The present invention refers to the method of synthesis of the substituted azetidinones of formula 1. In particular, the present invention refers to the method of synthesis of (3R,4S)-1-(4-fluorophenyl)-3-[(3´S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one.
PCT/PL2012/050022 2011-06-15 2012-06-15 Method for synthesis of the substituted azetidinones and intermediates for their synthesis WO2012173504A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PLP.395262 2011-06-15
PL395262A PL231215B1 (en) 2011-06-15 2011-06-15 Process for the preparation of substituted azetidinones and intermediates for the synthesis thereof

Publications (2)

Publication Number Publication Date
WO2012173504A2 WO2012173504A2 (en) 2012-12-20
WO2012173504A3 true WO2012173504A3 (en) 2013-02-21

Family

ID=46516810

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/PL2012/050022 WO2012173504A2 (en) 2011-06-15 2012-06-15 Method for synthesis of the substituted azetidinones and intermediates for their synthesis

Country Status (2)

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PL (1) PL231215B1 (en)
WO (1) WO2012173504A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107176920B (en) * 2017-04-19 2019-09-20 江苏恒盛药业有限公司 A kind of new technique for synthesizing of ezetimibe
CN114736250B (en) * 2022-04-07 2023-07-07 洛阳师范学院 Synthesis method of 2, 3-unsaturated glycoxyglycoside compounds based on organic fluorine mediation

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010097350A1 (en) * 2009-02-24 2010-09-02 Adamed Sp. Z O.O. A process for the preparation of an aldehyde beta-lactam compound

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5631365A (en) 1993-09-21 1997-05-20 Schering Corporation Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents
WO1997016424A1 (en) 1995-11-02 1997-05-09 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
US5739321A (en) 1996-05-31 1998-04-14 Schering Corporation 3-hydroxy γ-lactone based enantionselective synthesis of azetidinones
US6207822B1 (en) 1998-12-07 2001-03-27 Schering Corporation Process for the synthesis of azetidinones
CN1805926A (en) 2003-05-05 2006-07-19 兰贝克赛实验室有限公司 Process for the preparation of trans-isomers of diphenylazetidinone derivatives
US20090186834A1 (en) 2005-03-24 2009-07-23 Microbia, Inc. Diphenylheterocycle cholesterol absorption inhibitors
WO2008061238A2 (en) 2006-11-16 2008-05-22 Ironwood Pharmaceuticals, Inc. Processes for production of 4-biphenylyazetidin-2-ones

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010097350A1 (en) * 2009-02-24 2010-09-02 Adamed Sp. Z O.O. A process for the preparation of an aldehyde beta-lactam compound

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
GARANCE BROUSTAL ET AL: "A Stereoselective Approach to 1,3-Amino Alcohols Protected as Cyclic Carbamates: Kinetic vs. Thermodynamic Control", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2007, no. 26, 1 September 2007 (2007-09-01), pages 4293 - 4297, XP055037024, ISSN: 1434-193X, DOI: 10.1002/ejoc.200700503 *
GRANGE R L ET AL: "A convenient new route to enantiopure 3-hydroxy-5-oxo esters and 5,6-dihydropyran-2-ones: intricacies of the trithioorthoester protecting group", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 51, no. 8, 24 February 2010 (2010-02-24), pages 1158 - 1160, XP026861743, ISSN: 0040-4039, [retrieved on 20091216] *
KAILAS B. SAWANT ET AL: "Efficient Total Syntheses and Structural Verification of Both Diospongins A and B via a Common [delta]-Lactone Intermediate", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 71, no. 20, 1 September 2006 (2006-09-01), pages 7911 - 7914, XP055037035, ISSN: 0022-3263, DOI: 10.1021/jo061296f *
P. VEERARAGHAVAN RAMACHANDRAN ET AL: "Diastereoselective Dihydroxylation and Regioselective Deoxygenation of Dihydropyranones: A Novel Protocol for the Stereoselective Synthesis of C 1 -C 8 and C 15 -C 21 Subunits of (+)-Discodermolide", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 69, no. 19, 1 September 2004 (2004-09-01), pages 6294 - 6304, XP055037033, ISSN: 0022-3263, DOI: 10.1021/jo0492416 *

Also Published As

Publication number Publication date
PL395262A1 (en) 2012-12-17
PL231215B1 (en) 2019-02-28
WO2012173504A2 (en) 2012-12-20

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