WO2007030721A3 - 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 - Google Patents

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 Download PDF

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Publication number
WO2007030721A3
WO2007030721A3 PCT/US2006/035060 US2006035060W WO2007030721A3 WO 2007030721 A3 WO2007030721 A3 WO 2007030721A3 US 2006035060 W US2006035060 W US 2006035060W WO 2007030721 A3 WO2007030721 A3 WO 2007030721A3
Authority
WO
WIPO (PCT)
Prior art keywords
fluorophenyl
compound
processes
ezetimibe
azetidinone
Prior art date
Application number
PCT/US2006/035060
Other languages
French (fr)
Other versions
WO2007030721A2 (en
WO2007030721A9 (en
Inventor
Vinod Kumar Kansal
Suhail Ahmad
Bhupendra Tyagi
Nitin Gupta
Nurit Perlman
Original Assignee
Teva Pharma
Vinod Kumar Kansal
Suhail Ahmad
Bhupendra Tyagi
Nitin Gupta
Nurit Perlman
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 Teva Pharma, Vinod Kumar Kansal, Suhail Ahmad, Bhupendra Tyagi, Nitin Gupta, Nurit Perlman filed Critical Teva Pharma
Priority to EP06803223A priority Critical patent/EP1922304A2/en
Priority to MX2007005493A priority patent/MX2007005493A/en
Priority to BRPI0605934-1A priority patent/BRPI0605934A2/en
Priority to CA002616058A priority patent/CA2616058A1/en
Priority to JP2007538200A priority patent/JP2008517951A/en
Publication of WO2007030721A2 publication Critical patent/WO2007030721A2/en
Publication of WO2007030721A3 publication Critical patent/WO2007030721A3/en
Priority to IL186326A priority patent/IL186326A0/en
Publication of WO2007030721A9 publication Critical patent/WO2007030721A9/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D205/00Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06Heterocyclic 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
    • C07D205/08Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/04Anorexiants; Antiobesity agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/06Antihyperlipidemics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/12Antihypertensives
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

The invention encompasses (3R,4S)-4-((4-benzyloxy)phenyl)-l-(4-fluorophenyl)-3- (3-(4-fluorophenyl)-3-oxopropyl)-2-azetidinone (Compound 2a). The invention further encompasses processes tor preparing Compound 2a from Compound 1. The invention also encompasses processes for preparing a compound having Formula (A) from a compound having the formula (B); wherein R is selected from the group consisting of: H or a hydroxyl protecting group. The invention also encompasses processes for preparing Compound 2a, preferably to form Compound 2a-Form 01. Also included are processes for preparing ezetimibe from Compound 2a-Form 01 or Compound 2a prepared according to the invention, compositions containing such ezetimibe, and methods for reducing cholesterol using such compositions.
PCT/US2006/035060 2005-09-08 2006-09-08 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 WO2007030721A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP06803223A EP1922304A2 (en) 2005-09-08 2006-09-08 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
MX2007005493A MX2007005493A (en) 2005-09-08 2006-09-08 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.
BRPI0605934-1A BRPI0605934A2 (en) 2005-09-08 2006-09-08 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
CA002616058A CA2616058A1 (en) 2005-09-08 2006-09-08 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
JP2007538200A JP2008517951A (en) 2005-09-08 2006-09-08 (3R, 4S) -4-((4-Benzyloxy) phenyl) -1- (4-fluorophenyl) -3-((S) -3- (4-fluorophenyl) -3-hydroxypropyl) -2 -Preparation of intermediates for the synthesis of azetidinones, ie ezetimibe
IL186326A IL186326A0 (en) 2005-09-08 2007-10-07 Processes for the preparation of (3r,4s)-4-((4-benzyloxyl)phenyl)-1-(4-fluorophenyl)-3-hydroxypropyl)-2-azetidinone, an intermediate for the synthesis of ezetimibe

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US71591905P 2005-09-08 2005-09-08
US60/715,919 2005-09-08
US83243006P 2006-07-20 2006-07-20
US60/832,430 2006-07-20

Publications (3)

Publication Number Publication Date
WO2007030721A2 WO2007030721A2 (en) 2007-03-15
WO2007030721A3 true WO2007030721A3 (en) 2007-05-31
WO2007030721A9 WO2007030721A9 (en) 2008-04-24

Family

ID=37671943

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/035060 WO2007030721A2 (en) 2005-09-08 2006-09-08 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

Country Status (9)

Country Link
US (2) US20070259845A1 (en)
EP (1) EP1922304A2 (en)
JP (1) JP2008517951A (en)
KR (1) KR20070063592A (en)
BR (1) BRPI0605934A2 (en)
CA (1) CA2616058A1 (en)
IL (1) IL186326A0 (en)
MX (1) MX2007005493A (en)
WO (1) WO2007030721A2 (en)

Cited By (3)

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US7842684B2 (en) 2006-04-27 2010-11-30 Astrazeneca Ab Diphenylazetidinone derivatives possessing cholesterol absorption inhibitor activity
US7871998B2 (en) 2003-12-23 2011-01-18 Astrazeneca Ab Diphenylazetidinone derivatives possessing cholesterol absorption inhibitory activity
US7893048B2 (en) 2005-06-22 2011-02-22 Astrazeneca Ab 2-azetidinone derivatives as cholesterol absorption inhibitors for the treatment of hyperlipidaemic conditions

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AU2004286838A1 (en) * 2003-10-30 2005-05-19 Merck & Co., Inc. 2-azetidinones as anti-hypercholesterolemic agents
UY29607A1 (en) 2005-06-20 2007-01-31 Astrazeneca Ab CHEMICAL COMPOUNDS
AR057072A1 (en) 2005-06-22 2007-11-14 Astrazeneca Ab CHEMICAL COMPOUNDS DERIVED FROM 2-AZETIDINONE, PHARMACEUTICAL FORMULATION AND A COMPOUND PREPARATION PROCESS
HU0501164D0 (en) * 2005-12-20 2006-02-28 Richter Gedeon Vegyeszet New industrial process for the production of ezetimibe
EP1971573B1 (en) * 2005-12-22 2009-10-14 Medichem S.A. Processes for preparing intermediate compounds useful for the preparation of ezetimibe
US7956182B2 (en) * 2006-02-16 2011-06-07 Kotobuki Pharmaceutical Co., Ltd. Process for preparing optically active alcohols
JP2009529055A (en) * 2006-03-06 2009-08-13 テバ ファーマシューティカル インダストリーズ リミティド Ezetimibe composition
EP2007718A2 (en) * 2006-03-29 2008-12-31 Medichem, S.A. Processes for preparing ezetimibe and intermediate compounds useful for the preparation thereof
WO2008032338A2 (en) * 2006-09-11 2008-03-20 Manne Satyanarayana Reddy Improved process for the preparation of ezetimibe and its intermediates
CN102285906B (en) * 2007-01-24 2014-11-19 克尔克公司 Process for preparation of ezetimibe and derivatives thereof
EP1953140A1 (en) * 2007-01-24 2008-08-06 Krka Process for the preparation of ezetimibe and derivatives thereof
EP2155667A1 (en) * 2007-06-07 2010-02-24 Teva Pharmaceutical Industries Ltd. Reduction processes for the preparation of ezetimibe
US20090047716A1 (en) * 2007-06-07 2009-02-19 Nurit Perlman Reduction processes for the preparation of ezetimibe
WO2009032264A1 (en) * 2007-08-30 2009-03-12 Teva Pharmaceutical Industries Ltd. Processes for preparing intermediates of ezetimibe by microbial reduction
US8013189B2 (en) * 2007-09-21 2011-09-06 Basf Se Accelerated amide and ester reductions with amine boranes and additives
CZ2007843A3 (en) * 2007-11-30 2009-06-10 Zentiva, A. S. Process for preparing (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl)]-4-(4-hydroxyphenyl)-2-azetidinone and intermediates thereof
CZ2008317A3 (en) * 2008-05-21 2009-12-02 Zentiva, A. S. Process for preparing (3R,4S)-1-(4-fluorphenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl)]-4-(4-hydroxyphenyl)-2-azetidinone
EP2149547A1 (en) * 2008-07-30 2010-02-03 LEK Pharmaceuticals D.D. Process for the synthesis of ezetimibe and intermediates useful therefor
AR074752A1 (en) * 2008-12-17 2011-02-09 Hanmi Pharm Ind Co Ltd METHOD FOR PREPARING EZETIMIBA AND INTERMEDIARIES USED IN THE SAME
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
US9040262B2 (en) 2010-05-04 2015-05-26 Codexis, Inc. Biocatalysts for ezetimibe synthesis
WO2014019166A1 (en) * 2012-08-01 2014-02-06 上海威智医药科技有限公司 Industrial production method for high-activity borane compound
WO2015039675A1 (en) 2013-09-23 2015-03-26 Pharmathen S.A. Novel process for the preparation of ezetimibe intermediates
WO2015133405A1 (en) * 2014-03-06 2015-09-11 日産化学工業株式会社 Method for manufacturing optically active azetidinone compound
US11126809B2 (en) 2019-11-08 2021-09-21 Zebra Technologies Corporation Bioptic barcode readers
CN114621126B (en) * 2020-12-12 2023-07-25 重庆圣华曦药业股份有限公司 Improved ezetimibe preparation method
WO2023004414A1 (en) * 2021-07-23 2023-01-26 Colorado Chromatography, Llc A method for preparing hexahydrocannabinol
WO2023177452A1 (en) * 2022-03-14 2023-09-21 Colorado Chromatography, Llc Hydrogenation of cannabigerol and cannabichromene
CN115453004B (en) * 2022-10-08 2023-10-13 南京科默生物医药有限公司 Detection method of related substances in ezetimibe atorvastatin calcium tablet

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Publication number Priority date Publication date Assignee Title
US7871998B2 (en) 2003-12-23 2011-01-18 Astrazeneca Ab Diphenylazetidinone derivatives possessing cholesterol absorption inhibitory activity
US7893048B2 (en) 2005-06-22 2011-02-22 Astrazeneca Ab 2-azetidinone derivatives as cholesterol absorption inhibitors for the treatment of hyperlipidaemic conditions
US7842684B2 (en) 2006-04-27 2010-11-30 Astrazeneca Ab Diphenylazetidinone derivatives possessing cholesterol absorption inhibitor activity

Also Published As

Publication number Publication date
WO2007030721A2 (en) 2007-03-15
IL186326A0 (en) 2008-01-20
BRPI0605934A2 (en) 2009-05-26
KR20070063592A (en) 2007-06-19
EP1922304A2 (en) 2008-05-21
MX2007005493A (en) 2007-09-11
US20100010212A1 (en) 2010-01-14
JP2008517951A (en) 2008-05-29
CA2616058A1 (en) 2007-03-15
US20070259845A1 (en) 2007-11-08
WO2007030721A9 (en) 2008-04-24

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