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WO2007004028A3 - Processes for the preparation of penems and its intermediate - Google Patents

Processes for the preparation of penems and its intermediate Download PDF

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Publication number
WO2007004028A3
WO2007004028A3 PCT/IB2006/001821 IB2006001821W WO2007004028A3 WO 2007004028 A3 WO2007004028 A3 WO 2007004028A3 IB 2006001821 W IB2006001821 W IB 2006001821W WO 2007004028 A3 WO2007004028 A3 WO 2007004028A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
gram
formula
protecting group
lactam antibiotics
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/IB2006/001821
Other languages
French (fr)
Other versions
WO2007004028A2 (en
Inventor
Parendu Dhirajlal Rathod
Kiran Kumar Ganagakhedkar
Ram Chander Aryan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ranbaxy Laboratories Ltd
Original Assignee
Ranbaxy Laboratories Ltd
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 Laboratories Ltd filed Critical Ranbaxy Laboratories Ltd
Publication of WO2007004028A2 publication Critical patent/WO2007004028A2/en
Publication of WO2007004028A3 publication Critical patent/WO2007004028A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • 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)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The present invention relates to a process for the preparation of 4-acetoxy azetidinone of Formula I, wherein R2 is hydrogen or a suitable amino protecting group and P is suitable hydroxy protecting group, and to the use of these compounds as intermediates for the preparation of ß-lactam antibiotics that possess the carbapenem and penem ring systems. 4-acetoxy azetidinone of Formula I is a key intermediate in the synthesis of ß-lactam antibiotics which are commonly prescribed antimicrobial agents having activity against a wide range of both Gram-positive and Gram-negative bacteria.
PCT/IB2006/001821 2005-06-30 2006-06-30 Processes for the preparation of penems and its intermediate Ceased WO2007004028A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1702DE2005 2005-06-30
IN1702/DEL/2005 2005-06-30

Publications (2)

Publication Number Publication Date
WO2007004028A2 WO2007004028A2 (en) 2007-01-11
WO2007004028A3 true WO2007004028A3 (en) 2007-03-29

Family

ID=37205705

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2006/001821 Ceased WO2007004028A2 (en) 2005-06-30 2006-06-30 Processes for the preparation of penems and its intermediate

Country Status (1)

Country Link
WO (1) WO2007004028A2 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8952034B2 (en) 2009-07-27 2015-02-10 Gilead Sciences, Inc. Fused heterocyclic compounds as ion channel modulators
US8962610B2 (en) 2011-07-01 2015-02-24 Gilead Sciences, Inc. Fused heterocyclic compounds as ion channel modulators
US9115096B2 (en) 2011-05-10 2015-08-25 Gilead Sciences, Inc. Fused heterocyclic compounds as ion channel modulators
US9193694B2 (en) 2011-07-01 2015-11-24 Gilead Sciences, Inc. Fused heterocyclic compounds as ion channel modulators

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101265271B (en) * 2008-04-30 2013-06-05 寿光富康制药有限公司 Method for synthesizing penem-like pharmaceutical intermediate 4AA
CN101747250B (en) * 2008-12-16 2012-09-05 上海医药工业研究院 Method for preparing 4 - acyloxo heterocyclic ketone compounds
WO2011048583A1 (en) 2009-10-23 2011-04-28 Ranbaxy Laboratories Limited Process for the preparation of carbapenem compounds
ES2529119T3 (en) 2010-07-02 2015-02-17 Gilead Sciences, Inc. Condensed heterocyclic compounds as ion channel modulators
CN102432632A (en) * 2011-09-16 2012-05-02 上海悦昂化学有限公司 Method for preparing (3R,4R)-3-[(1R)tert-butyl-dimethyl-silyloxyethyl]-4-acetoxyl-2-azetidinone
CN102827199A (en) * 2012-08-28 2012-12-19 三峡大学 Synthetic method for penem and carbapenem antibiotic type key intermediate 4AA
CN102936262A (en) * 2012-11-07 2013-02-20 凯莱英医药集团（天津）股份有限公司 Preparation method for imipenem medicine intermediate 4AA
WO2014071565A1 (en) * 2012-11-07 2014-05-15 凯莱英医药集团（天津）股份有限公司 Preparation method for intermediate 4aa of imipenem drugs
CN103242361A (en) * 2013-05-23 2013-08-14 浙江海翔川南药业有限公司 Preparation method of penem antibiotic intermediate
CN109721521A (en) * 2018-11-26 2019-05-07 广东药科大学 A kind of preparation method of optical activity clausenamide ketone and its derivative
CN115385950B (en) * 2022-10-27 2023-04-28 天津凯莱英医药科技发展有限公司 System and method for preparing 4-acetoxyazetidinone by continuous ozone oxidation

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0126587A1 (en) * 1983-05-09 1984-11-28 Sumitomo Pharmaceuticals Company, Limited Carboxylic thio-pyrrolidinyl beta-lactam compounds and production thereof
EP0367722A1 (en) * 1988-11-04 1990-05-09 Ciba-Geigy Ag Process for preparing optically active acyloxyazetidinones
EP0371875A2 (en) * 1988-11-29 1990-06-06 Takasago International Corporation Process for preparing 4-acetoxyazetidinones
EP0528678A1 (en) * 1991-08-20 1993-02-24 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. A pyrrolidylthiocarbapenem derivative
WO1998007691A1 (en) * 1996-08-24 1998-02-26 Choongwae Pharmaceutical Co., Ltd. Process for stereoselective preparation of trans-azetidinones

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0126587A1 (en) * 1983-05-09 1984-11-28 Sumitomo Pharmaceuticals Company, Limited Carboxylic thio-pyrrolidinyl beta-lactam compounds and production thereof
US4943569A (en) * 1983-05-09 1990-07-24 Sumitomo Pharmaceuticals Co., Ltd. B-lactam compounds
EP0367722A1 (en) * 1988-11-04 1990-05-09 Ciba-Geigy Ag Process for preparing optically active acyloxyazetidinones
EP0371875A2 (en) * 1988-11-29 1990-06-06 Takasago International Corporation Process for preparing 4-acetoxyazetidinones
US5081239A (en) * 1988-11-29 1992-01-14 Takasago International Corporation Ruthenium catalyzed process for preparing 4-acetoxyazetidinones
EP0528678A1 (en) * 1991-08-20 1993-02-24 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. A pyrrolidylthiocarbapenem derivative
US5317016A (en) * 1991-08-20 1994-05-31 Shionogi Seiyaku Kabushiki Kaisha Pyrrolidylthiocarbapenem derivative
WO1998007691A1 (en) * 1996-08-24 1998-02-26 Choongwae Pharmaceutical Co., Ltd. Process for stereoselective preparation of trans-azetidinones
WO1998007690A1 (en) * 1996-08-24 1998-02-26 Choongwae Pharmaceutical Co., Ltd. Process for stereoselective preparation of 4-acetoxyazetidinones

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
CAINELLI, GIANFRANCO ET AL: "Stereocontrolled total synthesis of the chiral building block (3S,4R)-3-[(R)-1-hydroxyethyl]-4-acetyloxy-azetidin-2-one: a useful synthon for the synthesis of (+)-thienamycin, carbapenems and penems", TETRAHEDRON LETTERS, vol. 26, no. 7, 1985, pages 937 - 940, XP002406363 *
COZZI, FRANCO ET AL: "A short, stereoselective synthesis of (3R,4R)-4-acetoxy-3-[(R)-1'((t- butyldimethylsilyl)oxy)ethyl]-2-azetidinone, key intermediate for the preparation of carbapenem antibiotics", CHIRALITY, vol. 10, no. 1/2, 1998, pages 91 - 94, XP002406364 *
LAURENT, MATHIEU ET AL: "A new method of N-benzhydryl deprotection in 2-azetidinone series", SYNTHESIS, vol. 4, 2003, pages 570 - 576, XP002406359 *
LAURENT, MATHIEU ET AL: "Regioselective Baeyer-Villiger Oxidation in 4-Carbonyl-2-azetidinone Series: A Revisited Route toward Carbapenem Precursor", JOURNAL OF ORGANIC CHEMISTRY, vol. 69, no. 9, 2004, pages 3194 - 3197, XP002406360 *
SHIOZAKI, MASAO ET AL: "Stereocontrolled syntheses of chiral intermediates of thienamycin from threonines", TETRAHEDRON LETTERS, vol. 22, no. 51, 1981, pages 5205 - 5208, XP002406361 *
SHIOZAKI, MASAO ET AL: "Stereospecific synthesis of chiral precursors of thienamycin from L-threonine", TETRAHEDRON, vol. 40, no. 10, 1984, pages 1795 - 1802, XP002406362 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8952034B2 (en) 2009-07-27 2015-02-10 Gilead Sciences, Inc. Fused heterocyclic compounds as ion channel modulators
US9371329B2 (en) 2009-07-27 2016-06-21 Gilead Sciences, Inc. Fused heterocyclic compounds as ion channel modulators
US9115096B2 (en) 2011-05-10 2015-08-25 Gilead Sciences, Inc. Fused heterocyclic compounds as ion channel modulators
US9403782B2 (en) 2011-05-10 2016-08-02 Gilead Sciences, Inc. Fused heterocyclic compounds as ion channel modulators
US8962610B2 (en) 2011-07-01 2015-02-24 Gilead Sciences, Inc. Fused heterocyclic compounds as ion channel modulators
US9193694B2 (en) 2011-07-01 2015-11-24 Gilead Sciences, Inc. Fused heterocyclic compounds as ion channel modulators

Also Published As

Publication number Publication date
WO2007004028A2 (en) 2007-01-11

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