GB1359811A - 3-unsubstituted cephalosporins - Google Patents

3-unsubstituted cephalosporins

Info

Publication number
GB1359811A
GB1359811A GB34973A GB34973A GB1359811A GB 1359811 A GB1359811 A GB 1359811A GB 34973 A GB34973 A GB 34973A GB 34973 A GB34973 A GB 34973A GB 1359811 A GB1359811 A GB 1359811A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
formula
unsubstituted
amino
cephalosporins
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
GB34973A
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.)
GlaxoSmithKline LLC
Original Assignee
SmithKline Corp
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 SmithKline Corp filed Critical SmithKline Corp
Publication of GB1359811A publication Critical patent/GB1359811A/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
    • 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
    • C07D501/02—Preparation
    • C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
    • 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)
  • Cephalosporin Compounds (AREA)

Abstract

1359811 3 - Unsubstituted cephalosporins SMITHKLINE CORP 3 Jan 1973 [12 Jan 1972 28 March 1972] 349/73 Heading C2A 3-Unsubstituted cephalosporins of the Formula I: wherein R is hydrogen or acyl and M is hydrogen or a protecting group are prepared by reacting a compound of the Formula II: (any COOH, NH 2 or OH group present being suitably protected) with a decarbonylation reagent, e.g. tris-(triphenylphosphine) chlororhodium, in a compatible solvent at a temperature and for a length of time sufficient to cause decarbonylation without significant decomposition and, where it is desired to prepare a compound where M is H, then removing any protecting groups. The solvent is preferably benzene, toluene, xylene, benzonitrile, acetonitrile or methylene chloride, the temperature from 40-175‹ C., and time from 0À5-24 hours. Preferred compounds are those wherein acyl is NCCH 2 CO, Het-S-CH 2 CO, wherein Het is a 5- or 6-membered heterocyclic ring containing one to four hetero atoms selected from N, O and S, unsubstituted or substituted with one or two groups selected from C 1-4 alkyl, C 1-4 alkoxy, CF 3 , SCH 3 , and halogen; Y is hydrogen, OH, or NH 2 ; R<SP>1</SP> is hydrogen or a protecting group; A is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, hydroxy, amino, halogen or carboalkoxy, and M is hydrogen, 2,2,2-trichloroethyl, benzhydryl, t-butyl, p-nitrophenyl, pmethoxyphenyl, p - nitrobenzyl, p - methoxybenzyl or benzyloxymethyl. Compounds of the formula wherein R 2 is mandeloyl, p-hydroxymandeloyl, 3-sydnone acetyl, α-amino-p-hydroxyphenylacetyl or α-amino-1,4-cyclohexadienylacetyl; and M is hydrogen, an alkali metal, alkaline earth metal or organic ammonium cation are stated to be novel. The starting materials of Formula II may be prepared according to the reaction scheme: Antibacterial compositions comprise the above 3-unsubstituted cephalosporins of Formula I and a carrier and may be in the form of injectable solutions or capsules.
GB34973A 1972-01-12 1973-01-03 3-unsubstituted cephalosporins Expired GB1359811A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US21728372A 1972-01-12 1972-01-12
US23893272A 1972-03-28 1972-03-28

Publications (1)

Publication Number Publication Date
GB1359811A true GB1359811A (en) 1974-07-10

Family

ID=26911792

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34973A Expired GB1359811A (en) 1972-01-12 1973-01-03 3-unsubstituted cephalosporins

Country Status (7)

Country Link
JP (1) JPS49108089A (en)
BE (1) BE793724A (en)
CH (1) CH584228A5 (en)
DE (1) DE2301509A1 (en)
FR (1) FR2181658B1 (en)
GB (1) GB1359811A (en)
NL (1) NL7300487A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1192287B (en) * 1977-11-14 1988-03-31 Fujisawa Pharmaceutical Co PHARMACEUTICAL ACTION DERIVATIVES OF CEPHALOSPORANIC ACID AND RELATED PREPARATION PROCEDURE

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL37879A (en) * 1970-10-27 1974-12-31 Ciba Geigy Ag 3-unsubstituted cephalosporin derivatives,process for their manufacture and compositions containing them

Also Published As

Publication number Publication date
FR2181658A1 (en) 1973-12-07
FR2181658B1 (en) 1976-06-25
NL7300487A (en) 1973-07-16
JPS49108089A (en) 1974-10-14
CH584228A5 (en) 1977-01-31
BE793724A (en) 1973-07-05
DE2301509A1 (en) 1973-07-19

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Legal Events

Date Code Title Description
414F Notice of opposition given (sect. 14/1949)
414A Case decided by the comptroller ** specification amended (sect. 14/1949)
49R Reference inserted (sect. 9/1949)
SPA Amended specification published
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee