GB1385895A - Antibiotics - Google Patents

Antibiotics

Info

Publication number
GB1385895A
GB1385895A GB570671A GB570671A GB1385895A GB 1385895 A GB1385895 A GB 1385895A GB 570671 A GB570671 A GB 570671A GB 570671 A GB570671 A GB 570671A GB 1385895 A GB1385895 A GB 1385895A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
acid
amino
carboxyl
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
GB570671A
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo 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 Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Priority to GB570671A priority Critical patent/GB1385895A/en
Priority to BE780020A priority patent/BE780020R/en
Priority to FR7206794A priority patent/FR2128396B2/fr
Publication of GB1385895A publication Critical patent/GB1385895A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1385895 3-Methylthiomethylcephalosporins GLAXO LABORATORIES Ltd 28 Feb 1972 [1 March 1971] 5706/71 Addition to 1277415 Heading C2C The invention comprises 3-methylthiomethylceph-3-en-4-carboxylic acids of Formula I: wherein R is the grouping R<SP>1</SP>CH(NH 2 )CO- wherein R<SP>1</SP> is o or m-tolyl, m-methoxyphenyl or thien-3-yl or R is D-2-amino-2-(thien-2-yl)- acetyl or R is 2-hydroxy-2-phenylacetyl, carboxylic acid derivatives thereof, acid addition salts thereof and carboxyl and/or amino protected forms of the above compounds. A process for the preparation of compounds of Formula I comprises acylating a compound of the Formula II: wherein R<SP>2</SP> is hydrogen or a carboxyl-blocking group and Z is >S or >S # O (α- or #-) with an acylating agent corresponding to the acid ROH wherein R has the above-defined meaning or reacting a compound of Formula III: with methane thiol or reacting a compound of Formula IV: wherein the acid HX has a pHa of not more than 4 (as measured in water at 25‹ C.) with methane thiol whereafter, if necessary, any of the following reactions are carried out: (i) conversion of a #<SP>2</SP> isomer into the desired #<SP>3</SP> isomer, (ii) removal of any groups protecting any amino, hydroxy or carboxyl groups and (iii) reduction of a compound in which Z is >S # O to form the desired Z=>S compound. Pharmaceutical compositions which may be adapted for use in human or veterinary medicine comprise a 7-#-acylamido-3-methylthiomethylceph-3-em-4-carboxylic acid of Formula I or a non-toxic derivative in conjunction with a pharmaceutically acceptable excipient or carrier. Such compositions may be adapted for oral, parenteral or topical use.
GB570671A 1971-03-01 1971-03-01 Antibiotics Expired GB1385895A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB570671A GB1385895A (en) 1971-03-01 1971-03-01 Antibiotics
BE780020A BE780020R (en) 1971-03-01 1972-02-29 ACTIVE CEPHALOSPORIN COMPOUNDS
FR7206794A FR2128396B2 (en) 1971-03-01 1972-02-29

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB570671A GB1385895A (en) 1971-03-01 1971-03-01 Antibiotics

Publications (1)

Publication Number Publication Date
GB1385895A true GB1385895A (en) 1975-03-05

Family

ID=9801113

Family Applications (1)

Application Number Title Priority Date Filing Date
GB570671A Expired GB1385895A (en) 1971-03-01 1971-03-01 Antibiotics

Country Status (3)

Country Link
BE (1) BE780020R (en)
FR (1) FR2128396B2 (en)
GB (1) GB1385895A (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1337775A (en) * 1962-05-16 1963-09-20 Glaxo Lab Ltd New cephalosporin c derivatives and their preparation methods
CH550202A (en) * 1968-06-14 1974-06-14 Glaxo Lab Ltd PROCESS FOR PRODUCING NEW CEPHALOSPORIN COMPOUNDS.
ZA698494B (en) * 1969-02-26 1971-07-28 Lilly Co Eli Sulfur-containing cephalosporing antibiotics

Also Published As

Publication number Publication date
BE780020R (en) 1972-08-29
FR2128396B2 (en) 1976-04-16
FR2128396A2 (en) 1972-10-20

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Legal Events

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