WO2004099132A3 - Process for the preparation of trans-isomers of diphenylazetidinone derivatives - Google Patents

Process for the preparation of trans-isomers of diphenylazetidinone derivatives Download PDF

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Publication number
WO2004099132A3
WO2004099132A3 PCT/IB2004/001396 IB2004001396W WO2004099132A3 WO 2004099132 A3 WO2004099132 A3 WO 2004099132A3 IB 2004001396 W IB2004001396 W IB 2004001396W WO 2004099132 A3 WO2004099132 A3 WO 2004099132A3
Authority
WO
WIPO (PCT)
Prior art keywords
isomers
trans
preparation
diphenylazetidinone derivatives
diphenylazetidinone
Prior art date
Application number
PCT/IB2004/001396
Other languages
French (fr)
Other versions
WO2004099132A2 (en
Inventor
Kiran Kumar Ganagakhed Karooti
Parendu Dhirajlal Rathod
Ram Chander Aryan
Yatendra Kumar
Original Assignee
Ranbaxy Lab Ltd
Kiran Kumar Ganagakhed Karooti
Parendu Dhirajlal Rathod
Ram Chander Aryan
Yatendra 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, Kiran Kumar Ganagakhed Karooti, Parendu Dhirajlal Rathod, Ram Chander Aryan, Yatendra Kumar filed Critical Ranbaxy Lab Ltd
Priority to EP04731224A priority Critical patent/EP1626954A2/en
Publication of WO2004099132A2 publication Critical patent/WO2004099132A2/en
Publication of WO2004099132A3 publication Critical patent/WO2004099132A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen 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
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen 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 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
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • 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

Abstract

The invention relates to processes for the preparation of trans-isomers of diphenylazetidinone derivatives of formula (I), using a chiral delta-lactone. It also relates to processes for the preparation of the chiral delta-lactone. The invention also relates to pharmaceutical compositions that include the trans-isomers of diphenylazetidinone derivatives.
PCT/IB2004/001396 2003-05-05 2004-05-05 Process for the preparation of trans-isomers of diphenylazetidinone derivatives WO2004099132A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP04731224A EP1626954A2 (en) 2003-05-05 2004-05-05 Process for the preparation of trans-isomers of diphenylazetidinone derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN668DE2003 2003-05-05
IN668/DEL/2003 2003-05-05

Publications (2)

Publication Number Publication Date
WO2004099132A2 WO2004099132A2 (en) 2004-11-18
WO2004099132A3 true WO2004099132A3 (en) 2005-03-24

Family

ID=33428285

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2004/001396 WO2004099132A2 (en) 2003-05-05 2004-05-05 Process for the preparation of trans-isomers of diphenylazetidinone derivatives

Country Status (4)

Country Link
EP (1) EP1626954A2 (en)
CN (1) CN1805926A (en)
AR (1) AR044177A1 (en)
WO (1) WO2004099132A2 (en)

Families Citing this family (23)

* 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
CA2550215A1 (en) 2003-12-23 2005-07-07 Astrazeneca Ab Diphenylazetidinone derivates possessing cholesterol absorption inhibitory activity
US20060160785A1 (en) * 2004-12-03 2006-07-20 Judith Aronhime Ezetimibe polymorphs
TW200726746A (en) 2005-05-06 2007-07-16 Microbia Inc Processes for production of 4-biphenylylazetidin-2-ones
CA2608075A1 (en) * 2005-05-11 2006-11-16 Microbia, Inc. Processes for production of phenolic 4-biphenylylazetidin-2-ones
EP1896135A2 (en) * 2005-05-25 2008-03-12 Microbia, Inc. Processes for production of 4-(biphenylyl)azetidin-2-one phosphonic acids
UY29607A1 (en) 2005-06-20 2007-01-31 Astrazeneca Ab CHEMICAL COMPOUNDS
MY148538A (en) 2005-06-22 2013-04-30 Astrazeneca Ab Novel 2-azetidinone derivatives as cholesterol absorption inhibitors for the treatment of hyperlipidaemic conditions
SA06270191B1 (en) 2005-06-22 2010-03-29 استرازينيكا ايه بي Novel 2-Azetidinone Derivatives as Cholesterol Absorption Inhibitors for the Treatment of Hyperlipidaemic Conditions
WO2007017705A1 (en) * 2005-08-09 2007-02-15 Glenmark Pharmaceuticals Limited Process for the preparation of azetidinones
WO2008061238A2 (en) * 2006-11-16 2008-05-22 Ironwood Pharmaceuticals, Inc. Processes for production of 4-biphenylyazetidin-2-ones
EP2128133A1 (en) 2008-05-26 2009-12-02 Lek Pharmaceuticals D.D. Ezetimibe process and composition
AU2009253877B2 (en) * 2008-06-02 2013-09-12 Cipla Limited Process for the synthesis of arformoterol
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
PL231215B1 (en) 2011-06-15 2019-02-28 Inst Chemii Organicznej Polskiej Akademii Nauk Process for the preparation of substituted azetidinones and intermediates for the synthesis thereof
CN103086938A (en) * 2011-10-28 2013-05-08 沈阳药科大学 Ezetimibe synthesis method
CN103121966A (en) * 2011-11-17 2013-05-29 重庆华邦胜凯制药有限公司 Method for directionally synthesizing (4-chlorphenyl)-(pyridine-2-base)-methanol
CN103204795B (en) * 2012-01-11 2016-12-14 重庆华邦胜凯制药有限公司 A kind of preparation method of chirality azetidinones
EP2864284B1 (en) 2012-06-22 2017-07-05 Henkel AG & Co. KGaA Photolabile pro-fragrances
CN104744331B (en) * 2013-12-31 2018-05-15 浙江九洲药业股份有限公司 A kind of synthesis technique of Ezetimible intermediate
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
CN108586373A (en) * 2018-06-22 2018-09-28 苏州市贝克生物科技有限公司 The synthetic method of Ezetimibe intermediate
CN110818606B (en) * 2018-08-08 2021-06-29 上海博志研新药物技术有限公司 Preparation method of ezetimibe and intermediate thereof

Citations (1)

* 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

Patent Citations (1)

* 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

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DOWNHAM R ET AL: "Dispiroketals in Synthesis (Part 19)<1>: Dispiroketals as Enantioselective and Regioselective Protective Agents for Symmetric Cyclic and Acyclic Polyols", TETRAHEDRON: ASYMMETRY, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 6, no. 10, 1 October 1995 (1995-10-01), pages 2403 - 2440, XP004047992, ISSN: 0957-4166 *
ROSENBLUM S B ET AL: "Discovery of 1-(4-Fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)- hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235): A Designed, Potent, Orally Active Inhibitor of Cholesterol Absorption", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 41, 1998, pages 973 - 980, XP002275926, ISSN: 0022-2623 *
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, vol. 64, 1999, pages 3714 - 3718, XP002296009 *

Also Published As

Publication number Publication date
WO2004099132A2 (en) 2004-11-18
AR044177A1 (en) 2005-08-24
EP1626954A2 (en) 2006-02-22
CN1805926A (en) 2006-07-19

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