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WO2007004028A3 - Procedes de preparation de penemes et de leurs intermediaires - Google Patents

Procedes de preparation de penemes et de leurs intermediaires 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
Application number
PCT/IB2006/001821
Other languages
English (en)
Other versions
WO2007004028A2 (fr
Inventor
Parendu Dhirajlal Rathod
Kiran Kumar Ganagakhedkar
Ram Chander Aryan
Original Assignee
Ranbaxy Lab Ltd
Parendu Dhirajlal Rathod
Kiran Kumar Ganagakhedkar
Ram Chander Aryan
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, Parendu Dhirajlal Rathod, Kiran Kumar Ganagakhedkar, Ram Chander Aryan filed Critical Ranbaxy Lab Ltd
Publication of WO2007004028A2 publication Critical patent/WO2007004028A2/fr
Publication of WO2007004028A3 publication Critical patent/WO2007004028A3/fr

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

La présente invention concerne un procédé de préparation de 4-acétoxy-azétidinone de formule (I), dans laquelle R2 est hydrogène ou un groupe amino-protecteur approprié et P est un groupe hydroxy-protecteur approprié, ainsi que l'utilisation de ces composés comme intermédiaires pour la préparation d'antibiotiques de β-lactame renfermant les systèmes cycliques carbapénème et pénème. La 4-acétoxy-azétidinone de formule (I) est un intermédiaire clé dans la synthèse d'antibiotiques de β-lactame, lesquels sont des agents antimicrobiens communément prescrits dont l'activité est dirigée contre un large éventail de bactéries gram-positives et gram-négatives.
PCT/IB2006/001821 2005-06-30 2006-06-30 Procedes de preparation de penemes et de leurs intermediaires WO2007004028A2 (fr)

Applications Claiming Priority (2)

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

Publications (2)

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

Family

ID=37205705

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2006/001821 WO2007004028A2 (fr) 2005-06-30 2006-06-30 Procedes de preparation de penemes et de leurs intermediaires

Country Status (1)

Country Link
WO (1) WO2007004028A2 (fr)

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 (zh) * 2008-04-30 2013-06-05 寿光富康制药有限公司 培南类药物中间体4aa的合成方法
CN101747250B (zh) * 2008-12-16 2012-09-05 上海医药工业研究院 一种制备4-酰氧基氮杂环丁酮类化合物的方法
WO2011048583A1 (fr) 2009-10-23 2011-04-28 Ranbaxy Laboratories Limited Procédé pour la préparation de composés de carbapénème
MX2012015096A (es) 2010-07-02 2013-05-28 Gilead Sciences Inc Compuestos heterociclicos fusionados como moduladores del canal ion.
CN102432632A (zh) * 2011-09-16 2012-05-02 上海悦昂化学有限公司 一种（3r，4r）-3-[（1r）叔丁基二甲基硅氧乙基]-4-乙酰氧基-2-氮杂环丁酮的制备方法
CN102827199A (zh) * 2012-08-28 2012-12-19 三峡大学 青霉烯和碳青霉烯类抗生素类关键中间体4aa的合成方法
CN102936262A (zh) * 2012-11-07 2013-02-20 凯莱英医药集团（天津）股份有限公司 培南类药物中间体4aa的制备方法
WO2014071565A1 (fr) * 2012-11-07 2014-05-15 凯莱英医药集团（天津）股份有限公司 Procédé de préparation d'un intermédiaire 4aa des médicaments à base d'imipénème
CN103242361A (zh) * 2013-05-23 2013-08-14 浙江海翔川南药业有限公司 一种培南类抗生素中间体的制备方法
CN109721521A (zh) * 2018-11-26 2019-05-07 广东药科大学 一种光学活性黄皮酰胺酮及其衍生物的制备方法
CN115385950B (zh) * 2022-10-27 2023-04-28 天津凯莱英医药科技发展有限公司 连续臭氧氧化制备4-乙酰氧基氮杂环丁酮的系统及方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0126587A1 (fr) * 1983-05-09 1984-11-28 Sumitomo Pharmaceuticals Company, Limited Dérivés de carboxyle thio-pyrrolidinyle-bêta-lactame et leur préparation
EP0367722A1 (fr) * 1988-11-04 1990-05-09 Ciba-Geigy Ag Procédé de préparation d'acyloxyazétidinones optiquement actives
EP0371875A2 (fr) * 1988-11-29 1990-06-06 Takasago International Corporation Procédé de préparation d'acétoxy-4-azétidinones
EP0528678A1 (fr) * 1991-08-20 1993-02-24 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Dérivé de pyrrolidylthiocarbapénème
WO1998007691A1 (fr) * 1996-08-24 1998-02-26 Choongwae Pharmaceutical Co., Ltd. Procede de preparation stereoselective de trans-azetidinones

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0126587A1 (fr) * 1983-05-09 1984-11-28 Sumitomo Pharmaceuticals Company, Limited Dérivés de carboxyle thio-pyrrolidinyle-bêta-lactame et leur préparation
US4943569A (en) * 1983-05-09 1990-07-24 Sumitomo Pharmaceuticals Co., Ltd. B-lactam compounds
EP0367722A1 (fr) * 1988-11-04 1990-05-09 Ciba-Geigy Ag Procédé de préparation d'acyloxyazétidinones optiquement actives
EP0371875A2 (fr) * 1988-11-29 1990-06-06 Takasago International Corporation Procédé de préparation d'acétoxy-4-azétidinones
US5081239A (en) * 1988-11-29 1992-01-14 Takasago International Corporation Ruthenium catalyzed process for preparing 4-acetoxyazetidinones
EP0528678A1 (fr) * 1991-08-20 1993-02-24 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Dérivé de pyrrolidylthiocarbapénème
US5317016A (en) * 1991-08-20 1994-05-31 Shionogi Seiyaku Kabushiki Kaisha Pyrrolidylthiocarbapenem derivative
WO1998007691A1 (fr) * 1996-08-24 1998-02-26 Choongwae Pharmaceutical Co., Ltd. Procede de preparation stereoselective de trans-azetidinones
WO1998007690A1 (fr) * 1996-08-24 1998-02-26 Choongwae Pharmaceutical Co., Ltd. Procede de preparation stereoselective de 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 (fr) 2007-01-11

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