CA2433874A1 - Improved process for carbapenem synthesis - Google Patents

Improved process for carbapenem synthesis Download PDF

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Publication number
CA2433874A1
CA2433874A1 CA002433874A CA2433874A CA2433874A1 CA 2433874 A1 CA2433874 A1 CA 2433874A1 CA 002433874 A CA002433874 A CA 002433874A CA 2433874 A CA2433874 A CA 2433874A CA 2433874 A1 CA2433874 A1 CA 2433874A1
Authority
CA
Canada
Prior art keywords
improved process
carbapenem synthesis
carbapenem
synthesis
deprotection
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.)
Granted
Application number
CA002433874A
Other languages
French (fr)
Other versions
CA2433874C (en
Inventor
John M. Williams
Renato Skerlj
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.)
Merck Sharp and Dohme LLC
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2433874A1 publication Critical patent/CA2433874A1/en
Application granted granted Critical
Publication of CA2433874C publication Critical patent/CA2433874C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
    • C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
    • C07D477/20—Sulfur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/02—Preparation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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

Abstract

A process for synthesizing a compound represented by formula I: or a pharmaceutically acceptable salt thereof, wherein deprotection is conducted using a prereduced metal catalyst is disclosed.
CA002433874A 2001-01-16 2002-01-11 Improved process for carbapenem synthesis Expired - Fee Related CA2433874C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US26193301P 2001-01-16 2001-01-16
US60/261,933 2001-01-16
US29344001P 2001-05-24 2001-05-24
US60/293,440 2001-05-24
PCT/US2002/000821 WO2002057266A1 (en) 2001-01-16 2002-01-11 Improved process for carbapenem synthesis

Publications (2)

Publication Number Publication Date
CA2433874A1 true CA2433874A1 (en) 2002-07-25
CA2433874C CA2433874C (en) 2009-08-11

Family

ID=26948925

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002433874A Expired - Fee Related CA2433874C (en) 2001-01-16 2002-01-11 Improved process for carbapenem synthesis

Country Status (29)

Country Link
US (1) US7071330B2 (en)
EP (1) EP1353923B1 (en)
JP (1) JP4098626B2 (en)
KR (1) KR100827562B1 (en)
CN (1) CN1249065C (en)
AR (1) AR035728A1 (en)
AT (1) ATE278691T1 (en)
AU (1) AU2002234240B2 (en)
BR (1) BR0206372A (en)
CA (1) CA2433874C (en)
CZ (1) CZ301440B6 (en)
DE (1) DE60201498T2 (en)
DK (1) DK1353923T3 (en)
EA (1) EA006098B1 (en)
EG (1) EG23993A (en)
ES (1) ES2227423T3 (en)
HR (1) HRP20030566B1 (en)
HU (1) HUP0302764A3 (en)
IL (2) IL156507A0 (en)
MX (1) MXPA03006322A (en)
NZ (1) NZ527191A (en)
PL (1) PL362912A1 (en)
PT (1) PT1353923E (en)
RS (1) RS50494B (en)
SI (1) SI1353923T1 (en)
SK (1) SK287350B6 (en)
TW (1) TWI318627B (en)
UA (1) UA74870C2 (en)
WO (1) WO2002057266A1 (en)

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WO2003016312A1 (en) * 2001-08-13 2003-02-27 Eisai Co., Ltd. Process for preparation of carbapenem antibiotics
CA2457642C (en) * 2001-09-26 2009-01-06 Merck & Co., Inc. Crystalline forms of ertapenem sodium
AU2002341747B2 (en) * 2001-09-26 2007-10-18 Merck Sharp & Dohme Corp. Process for making carbapenem compounds
JP2005509037A (en) * 2001-11-16 2005-04-07 ランバクシー ラボラトリーズ リミテッド Crystalline imipenem production method
CN101172962B (en) * 2002-11-13 2010-09-08 株式会社钟化 Synthetic intermediate for carbapenem compound for oral administration
DE102005025899A1 (en) * 2005-06-06 2006-12-07 Basf Ag Process for the preparation of a reaction mixture containing alkoxycarbonylaminotriazine
BRPI0616563A2 (en) * 2005-09-15 2012-12-25 Orchid Chemicals & Pharm Ltd improved process for the preparation of beta-lactam antibiotic
TW200801004A (en) * 2006-03-28 2008-01-01 Kaneka Corp Improved process for producing carbapenem compound
US8293894B2 (en) 2006-11-20 2012-10-23 Orchid Chemicals & Pharmaceuticals Limited Process for the preparation of carbapenem antibiotic
CN101357920B (en) * 2007-06-22 2011-01-12 山东轩竹医药科技有限公司 Penem derivative containing sulfhydryl pyrrolidine formamido triazine
CN101367807B (en) * 2007-06-28 2011-01-12 山东轩竹医药科技有限公司 Sulfhydryl pyrrolidine formamido pyridine substituted penem derivant
KR101694506B1 (en) 2009-04-30 2017-01-10 씨에스피씨 종콰이 팔마씨우티컬 테크놀로지 (스자좡) 컴퍼니 리미티드 Intermediates of ertapenem, compositions containing them and preparation methods thereof
US20130079322A1 (en) * 2010-05-21 2013-03-28 Xuanzhu Pharama Co., Ltd. Crystalline of carbapenem derivative or its hydrate, preparation methods and uses thereof
CN103025733B (en) * 2010-06-03 2015-11-25 山东轩竹医药科技有限公司 Crystal formation of Carbpenem derivants or its hydrate and preparation method thereof and purposes
WO2012038979A2 (en) * 2010-09-24 2012-03-29 Sequent Anti Biotics Private Limited A process for preparation of ertapenem
CN102558182B (en) 2010-12-31 2015-02-11 石药集团中奇制药技术（石家庄）有限公司 Ertapenem sodium crystal form E and preparation method thereof
WO2013121279A2 (en) * 2012-02-14 2013-08-22 Aurobindo Pharma Limited Process to prepare ertapenem
WO2014097221A1 (en) * 2012-12-21 2014-06-26 Ranbaxy Laboratories Limited Process for the purification of biapenem
GB2529738B (en) * 2014-03-27 2018-10-17 Johnson Matthey Plc Process for preparing a carbapenem antibiotic

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US3925372A (en) * 1973-02-23 1975-12-09 Lilly Co Eli Alpha-aminoacyl-3-halo cephalosporins
US3897424A (en) * 1973-07-23 1975-07-29 Lilly Co Eli Process for 7-{62 -amino-7-{60 -methoxy-cephalosporanic acid esters and related compounds
AR207327A1 (en) * 1974-02-06 1976-09-30 Lilly Co Eli A PROCEDURE FOR PREPARING 3-CEFEM 3-SULFONATES ACIDS AND THEIR ESTERS
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Also Published As

Publication number Publication date
CZ20031911A3 (en) 2003-10-15
PL362912A1 (en) 2004-11-02
EP1353923A1 (en) 2003-10-22
PT1353923E (en) 2005-01-31
DE60201498T2 (en) 2005-11-17
ES2227423T3 (en) 2005-04-01
SK8972003A3 (en) 2003-10-07
IL156507A (en) 2010-06-30
EA200300804A1 (en) 2003-12-25
WO2002057266A1 (en) 2002-07-25
KR100827562B1 (en) 2008-05-07
TWI318627B (en) 2009-12-21
RS50494B (en) 2010-03-02
US7071330B2 (en) 2006-07-04
YU55003A (en) 2006-05-25
CN1249065C (en) 2006-04-05
ATE278691T1 (en) 2004-10-15
CA2433874C (en) 2009-08-11
UA74870C2 (en) 2006-02-15
AR035728A1 (en) 2004-07-07
EG23993A (en) 2008-03-10
IL156507A0 (en) 2004-01-04
HRP20030566A2 (en) 2005-06-30
SI1353923T1 (en) 2005-02-28
DE60201498D1 (en) 2004-11-11
MXPA03006322A (en) 2003-10-06
JP2004518672A (en) 2004-06-24
CZ301440B6 (en) 2010-03-03
BR0206372A (en) 2003-12-23
DK1353923T3 (en) 2005-01-31
KR20040007438A (en) 2004-01-24
EA006098B1 (en) 2005-08-25
HRP20030566B1 (en) 2011-08-31
US20040063931A1 (en) 2004-04-01
CN1486318A (en) 2004-03-31
HUP0302764A2 (en) 2003-11-28
HUP0302764A3 (en) 2005-11-28
NZ527191A (en) 2004-04-30
EP1353923B1 (en) 2004-10-06
SK287350B6 (en) 2010-08-09
AU2002234240B2 (en) 2006-04-27
JP4098626B2 (en) 2008-06-11

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