CA2294342A1 - Process for synthesizing carbapenem side chain intermediates - Google Patents

Process for synthesizing carbapenem side chain intermediates Download PDF

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Publication number
CA2294342A1
CA2294342A1 CA002294342A CA2294342A CA2294342A1 CA 2294342 A1 CA2294342 A1 CA 2294342A1 CA 002294342 A CA002294342 A CA 002294342A CA 2294342 A CA2294342 A CA 2294342A CA 2294342 A1 CA2294342 A1 CA 2294342A1
Authority
CA
Canada
Prior art keywords
compound
side chain
formula
synthesizing
chain intermediates
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
CA002294342A
Other languages
French (fr)
Other versions
CA2294342C (en
Inventor
Karel M. J. Brands
John M. Williams
Ulf H. Dolling
Ronald B. Jobson
Antony J. Davies
Ian F. Cottrell
Mark Cameron
Michael S. Ashwood
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
Priority claimed from GBGB9810184.3A external-priority patent/GB9810184D0/en
Application filed by Individual filed Critical Individual
Publication of CA2294342A1 publication Critical patent/CA2294342A1/en
Application granted granted Critical
Publication of CA2294342C publication Critical patent/CA2294342C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings

Abstract

A process of synthesizing a compound of formula (1) is described. A compound of formula (2) is reacted with diphenylphosphinic chloride to activate the carboxylic acid group, and then reacted with methanesulfonyl chloride to produce a compound of formula (4). Compound (4) is then reacted with a group II metal sulfide source in water to produce a compound of formula (1).
CA002294342A 1997-07-09 1998-07-02 Process for synthesizing carbapenem side chain intermediates Expired - Fee Related CA2294342C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US5203297P 1997-07-09 1997-07-09
US60/052,032 1997-07-09
GB9810184.3 1998-05-13
GBGB9810184.3A GB9810184D0 (en) 1998-05-13 1998-05-13 Process for synthisizing carbapenem side chain intermediates
PCT/US1998/013738 WO1999002531A1 (en) 1997-07-09 1998-07-02 Process for synthesizing carbapenem side chain intermediates

Publications (2)

Publication Number Publication Date
CA2294342A1 true CA2294342A1 (en) 1999-01-21
CA2294342C CA2294342C (en) 2006-03-14

Family

ID=26313663

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002294342A Expired - Fee Related CA2294342C (en) 1997-07-09 1998-07-02 Process for synthesizing carbapenem side chain intermediates

Country Status (5)

Country Link
EP (1) EP1019411A4 (en)
JP (1) JP2002504156A (en)
AU (1) AU731586B2 (en)
CA (1) CA2294342C (en)
WO (1) WO1999002531A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3378021B2 (en) * 1997-07-10 2003-02-17 メルク エンド カンパニー インコーポレーテッド Antibacterial side chain intermediate in crystalline form
AU4723501A (en) * 2000-03-01 2001-09-12 Merck & Co., Inc. Crystalline forms of antibiotic side chain intermediates
AU2002214325A1 (en) * 2000-11-20 2002-05-27 Sankyo Company Limited Process for producing carbapenem-type antibacterial
CA2576530A1 (en) * 2004-08-11 2006-02-23 Donald L. Barbeau Noncardiotoxic pharmaceutical compounds
CN102264744A (en) * 2008-12-25 2011-11-30 株式会社钟化 Improved process for producing intermediate for side chain of carbapenem
CN106565579A (en) * 2016-06-26 2017-04-19 宁夏海诚电化信息科技有限公司 Ertapenem side chain production technology

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4340738A (en) * 1979-06-21 1982-07-20 Janssen Pharmaceutica, N.V. 2,3-Dihydro-imidazo[2,1-b]benzothiazoles
AU644008B2 (en) * 1990-08-10 1993-12-02 Sumitomo Pharmaceuticals Company, Limited Beta-lactam compounds, and their production and use
JP3091297B2 (en) * 1992-01-10 2000-09-25 住友製薬株式会社 Pyrrolidine derivative and method for producing the same
CA2227696C (en) * 1995-08-04 2003-09-23 Merck & Co., Inc. Process for synthesizing carbapenem side chain intermediates

Also Published As

Publication number Publication date
WO1999002531A1 (en) 1999-01-21
AU8282198A (en) 1999-02-08
EP1019411A4 (en) 2003-08-13
JP2002504156A (en) 2002-02-05
AU731586B2 (en) 2001-04-05
CA2294342C (en) 2006-03-14
EP1019411A1 (en) 2000-07-19

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