EA201001352A1 - Промежуточные соединения для получения (3r,4s)-1-(4-фторфенил)-3-[(3s)-3-(4-фторфенил)-3-гидроксипропил]-4-(4-гидроксифенил)-2-ацетидинона - Google Patents

Промежуточные соединения для получения (3r,4s)-1-(4-фторфенил)-3-[(3s)-3-(4-фторфенил)-3-гидроксипропил]-4-(4-гидроксифенил)-2-ацетидинона

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Publication number
EA201001352A1
EA201001352A1 EA201001352A EA201001352A EA201001352A1 EA 201001352 A1 EA201001352 A1 EA 201001352A1 EA 201001352 A EA201001352 A EA 201001352A EA 201001352 A EA201001352 A EA 201001352A EA 201001352 A1 EA201001352 A1 EA 201001352A1
Authority
EA
Eurasian Patent Office
Prior art keywords
fluoro
phenyl
propylene
general formula
obtaining
Prior art date
Application number
EA201001352A
Other languages
English (en)
Other versions
EA017362B1 (ru
Inventor
Гана Степанкова
Йосеф Гайицек
Маркета Славикова
Йосеф Зезула
Original Assignee
Зентива, К.С.
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 Зентива, К.С. filed Critical Зентива, К.С.
Publication of EA201001352A1 publication Critical patent/EA201001352A1/ru
Publication of EA017362B1 publication Critical patent/EA017362B1/ru

Links

Classifications

    • 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
    • C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
    • 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
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Способ получения (S)-спиртооксазолидидов общей формулы II, где PG представляет собой водород или гидроксильную защитную группу, такую как триметилсилил, трет-бутилдиметилсилил, бензилокарбонил, трет-бутоксикарбонил, бензил, бензгидрил или тритил, в котором с кеталь оксазолидида общей формулы III, где PG имеет то же значение, что и выше, и R означает алкил с 1-4 атомами углерода, линейный или разветвленный, такой как метил, этил, изопропил или бутил, или R+R вместе представляют дивалентный алкил, или замещенный 1 или 2 алкильными группами, например, 1,2-этилен, 1,2-пропилен, 1,2-бутилен, 1,3-пропилен или 2,2-диметил-1,3-пропилен; снимают защиту действием кислотных реагентов в смеси воды и смешиваемого с водой растворителя в температурном диапазоне от 0 до 100°С (стадия А) и полученный кетон оксазолидид общей формулы IV, где PG имеет то же значение, что и выше, восстанавливают асимметричными реагентами в инертном органическом растворителе в температурном диапазоне от -30 до +40°С (стадия В).
EA201001352A 2008-02-25 2009-02-13 Промежуточные соединения для получения (3r,4s)-1-(4-фторфенил)-3-[(3s)-3-(4-фторфенил)-3-гидроксипропил]-4-(4-гидроксифенил)-2-азетидинона EA017362B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CZ2008-107A CZ305066B6 (cs) 2008-02-25 2008-02-25 Způsob výroby (3R,4S)-1-(4-fluorfenyl)-3-[(3S)-3-(4-fluorfenyl)-3-hydroxypropyl)]-4-(4-hydroxyfenyl)-2-azetidinonu
PCT/CZ2009/000016 WO2009106021A1 (en) 2008-02-25 2009-02-13 Intermediates for the preparation of (3r, 4s) -1- (4-fluorophenyl) -3- [ (3s) -3- (4-fluorophenyl) -3-hydroxypropyl) ] -4- (4-hydroxyphenyl) -2-azetidinone

Publications (2)

Publication Number Publication Date
EA201001352A1 true EA201001352A1 (ru) 2011-02-28
EA017362B1 EA017362B1 (ru) 2012-11-30

Family

ID=40599664

Family Applications (1)

Application Number Title Priority Date Filing Date
EA201001352A EA017362B1 (ru) 2008-02-25 2009-02-13 Промежуточные соединения для получения (3r,4s)-1-(4-фторфенил)-3-[(3s)-3-(4-фторфенил)-3-гидроксипропил]-4-(4-гидроксифенил)-2-азетидинона

Country Status (6)

Country Link
US (1) US20110046389A1 (ru)
EP (1) EP2276753A1 (ru)
CZ (1) CZ305066B6 (ru)
EA (1) EA017362B1 (ru)
UA (1) UA103020C2 (ru)
WO (1) WO2009106021A1 (ru)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUP0501164A2 (en) * 2005-12-20 2007-07-30 Richter Gedeon Nyrt New industrial process for the production of ezetimibe
ATE445596T1 (de) * 2005-12-22 2009-10-15 Medichem Sa Verfahren zur herstellung von zwischenprodukten für die herstellung von ezetimibe
AR060216A1 (es) * 2006-03-29 2008-06-04 Medichem Sa Procesos para preparar ezetimibe y compuestos intermediarios utiles para su preparacion
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
CN102731489B (zh) * 2011-04-11 2016-10-26 天津药物研究院有限公司 一种依折麦布关键中间体的制备方法
CN102850390B (zh) * 2011-07-01 2017-02-08 江苏豪森药业集团有限公司 依折麦布的中间体及其制备方法
CN103159751A (zh) * 2011-12-13 2013-06-19 重庆华邦胜凯制药有限公司 苯酮酸酰胺缩酮衍生物的制备方法
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
EP3672939A1 (en) 2017-08-21 2020-07-01 Celgene Corporation Processes for preparation of (s)-tert-butyl 4,5-diamino-5-oxopentanoate

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
US5739321A (en) * 1996-05-31 1998-04-14 Schering Corporation 3-hydroxy γ-lactone based enantionselective synthesis of azetidinones
US5886171A (en) * 1996-05-31 1999-03-23 Schering Corporation 3-hydroxy gamma-lactone based enantioselective synthesis of azetidinones
WO2000034240A1 (en) * 1998-12-07 2000-06-15 Schering Corporation Process for the synthesis of azetidinones
EP1851197A2 (en) * 2005-02-09 2007-11-07 Microbia, Inc. Phenylazetidinone derivatives
ATE445596T1 (de) * 2005-12-22 2009-10-15 Medichem Sa Verfahren zur herstellung von zwischenprodukten für die herstellung von ezetimibe
US20080032964A1 (en) * 2006-04-10 2008-02-07 Kansal Vinod K Process for the synthesis of azetidinone

Also Published As

Publication number Publication date
US20110046389A1 (en) 2011-02-24
UA103020C2 (ru) 2013-09-10
EA017362B1 (ru) 2012-11-30
EP2276753A1 (en) 2011-01-26
CZ2008107A3 (cs) 2010-02-24
WO2009106021A1 (en) 2009-09-03
CZ305066B6 (cs) 2015-04-22

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Legal Events

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MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): AM AZ KG MD TJ TM

MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): BY KZ