GB1325846A - Process for the preparation of a 3-thiomethyl cephalosporin - Google Patents

Process for the preparation of a 3-thiomethyl cephalosporin

Info

Publication number
GB1325846A
GB1325846A GB1325846DA GB1325846A GB 1325846 A GB1325846 A GB 1325846A GB 1325846D A GB1325846D A GB 1325846DA GB 1325846 A GB1325846 A GB 1325846A
Authority
GB
United Kingdom
Prior art keywords
alkyl
formula
hydrogen
preparation
thiomethyl
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.)
Expired
Application number
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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 Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB1325846A publication Critical patent/GB1325846A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/36—Methylene radicals, substituted by sulfur atoms

Abstract

1325846 Preparation of 3-thiomethyl cephalosporins ELILILLY & CO 23 Feb 1972 8301/72 Heading C2A A process for the preparation of a 3-thiomethyl cephalosporin of Formula 1 or the sulphoxide thereof which comprises treating a 3-halomethyl cephalosporin having the Formula II or the sulphoxide thereof, at a temperature of 0‹ to 50‹C. with a mercaptan having the formula R<SP>2</SP>SH wherein X is chlorine, bromine or iodine, R is C 1 -C 6 alkyl, or Z-(CH 2 )mA-(CH 2 )n-; Z is thienyl, furyl or a grouping of Formula III Y is protected hydroxyl or protected amino; A is oxygen, sulphur or a carbon to carbon bond; m is an integer of 0 to 4; n is an integer of 1-4; Q is hydrogen, fluorine, chlorine, bromine, C 1 -C 6 alkyl, C 1 -C 2 alkoxy, nitro, cyano, hydroxyl, or trifluoromethyl; R 1 is hydrogen, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, benzyl, methoxybenzyl, nitrobenzyl, benzhydryl, trityl, phthalimidomethyl, succirimido-methyl, phenacyl, or trimethylsilyl ; R<SP>2</SP> is C 1 -C 6 alkyl ; C 2 -C 6 alkyl substituted with hydroxy, nitro, di(C 1 -C 4 alkyl) amino, cyano, or halo; C 3 -C 6 alkenyl; benzyl; phenyl; pyridyl; thienyl; furyl; thiadiazyl; tetrazyl; or R<SP>3</SP> is OR<SP>4</SP> or N(R<SP>4</SP>) 2 ; and R<SP>4</SP> is hydrogen or C 1 -C 4 alkyl; said treatment taking place in an inert solvent selected from dimethylformamide, dimethylacetamide, or hexamethylphosphoramide.
GB1325846D 1972-02-23 1972-02-23 Process for the preparation of a 3-thiomethyl cephalosporin Expired GB1325846A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB830172 1972-02-23

Publications (1)

Publication Number Publication Date
GB1325846A true GB1325846A (en) 1973-08-08

Family

ID=9849897

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1325846D Expired GB1325846A (en) 1972-02-23 1972-02-23 Process for the preparation of a 3-thiomethyl cephalosporin

Country Status (1)

Country Link
GB (1) GB1325846A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5686188A (en) * 1979-11-19 1981-07-13 Fujisawa Pharmaceut Co Ltd 7-acylamino-3-substituted cephalosporanic acid derivative and its preparation
EP0108977A2 (en) * 1979-11-19 1984-05-23 Fujisawa Pharmaceutical Co., Ltd. Starting compounds for preparing 7-acylamino-3-substituted cephalosporanic acid derivatives and process for their preparation
JPS6140291A (en) * 1984-07-31 1986-02-26 Shionogi & Co Ltd Hydroxyalkylthiocephalosporin
WO1999031110A1 (en) * 1997-12-12 1999-06-24 Eli Lilly And Company Cephalosporin antibiotics
US6369049B1 (en) 1998-04-30 2002-04-09 Eli Lilly And Company Treatment of mastitis

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5686188A (en) * 1979-11-19 1981-07-13 Fujisawa Pharmaceut Co Ltd 7-acylamino-3-substituted cephalosporanic acid derivative and its preparation
EP0108977A2 (en) * 1979-11-19 1984-05-23 Fujisawa Pharmaceutical Co., Ltd. Starting compounds for preparing 7-acylamino-3-substituted cephalosporanic acid derivatives and process for their preparation
EP0108977A3 (en) * 1979-11-19 1985-05-15 Fujisawa Pharmaceutical Co., Ltd. Starting compounds for preparing 7-acylamino-3-substituted cephalosporanic acid derivatives and process for their preparation
JPS6140291A (en) * 1984-07-31 1986-02-26 Shionogi & Co Ltd Hydroxyalkylthiocephalosporin
WO1999031110A1 (en) * 1997-12-12 1999-06-24 Eli Lilly And Company Cephalosporin antibiotics
US6329363B1 (en) * 1997-12-12 2001-12-11 Eli Lilly And Company Cephalosporin antibiotics
US6369049B1 (en) 1998-04-30 2002-04-09 Eli Lilly And Company Treatment of mastitis

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee