GB1284974A - Novel diacyl penicillins and process for their production - Google Patents

Novel diacyl penicillins and process for their production

Info

Publication number
GB1284974A
GB1284974A GB06961/70A GB1696170A GB1284974A GB 1284974 A GB1284974 A GB 1284974A GB 06961/70 A GB06961/70 A GB 06961/70A GB 1696170 A GB1696170 A GB 1696170A GB 1284974 A GB1284974 A GB 1284974A
Authority
GB
United Kingdom
Prior art keywords
penicillins
diacyl
reaction
group
reacting
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
GB06961/70A
Inventor
J Abe
T Watanabe
T Take
K Fujimoto
T Fujii
K Takemura
K Nishiie
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.)
Toyo Jozo KK
Original Assignee
Toyo Jozo KK
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 Toyo Jozo KK filed Critical Toyo Jozo KK
Publication of GB1284974A publication Critical patent/GB1284974A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D499/00Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

1284974 Diacyl penicillins TOYO JOZO KK 9 April 1970 [11 April 1969] 16961/70 Heading C2A Novel diacyl penicillins of formula wherein R is a carboxyl-protecting group and R 1 and R 2 are the same or different and are hydrogen or halogen, are prepared by reacting a benzylpenicillin ester in which the esterifying group is the group R as above, with a chlorinating agent in the presence of a tertiary organic base to give an imide chloride group-containing compound of formula wherein R is as above, and then reacting this compound with an isoxazole carboxylate of formula in which M is a metal atom and R 1 and R 2 are as above. Suitable carboxyl-protecting groups R are methyl, ethyl, t-butyl, p-methoxybenzyl, benzyl, p-nitrobenzyl, benzhydryl, phenacyl, p-bromophenacyl or trimethylsilyl. The preparation of the p-bromophenacyl and p-nitrobenzyl esters of benzylpenicillin by reacting the penicillin with the appropriate acyl bromide is described. The preferred chlorinating agent is PCl 5 , others suitable being PCl 3 , POCl 3 , COCl 2 or SOCl 2 ; the reaction is performed in an anhydrous organic solvent which is preferably water-immiscible, at about - 20‹ to 25‹ C. The tertiary organic base is preferably a weak base such as pyridine, quinoline or dimethylaniline. After the imide chloride preparation step, the reaction solution may be used for the next stage without further purification, or, if desired, may be filtered to remove any precipitated tertiary base hydrochloride, washed with dilute aqueous alkali to remove chlorinating agent derived compounds (e.g. POCl 3 and HCl) and then concentrated and redissolved in another reaction solvent. The isoxazole carboxylate salt may be that of K, Na, Li or Ag. The reaction may be effected by simply adding the salt to the imide chloride solution from the first stage, if necessary with heating to 40‹ to 50‹ C. The reaction mixture is then washed with water, aqueous acid and alkali, concentrated and chromatographed on a silica gel column using, e.g., benzene-ethyl acetate. The required diacyl penicillin may be isolated by freeze-drying the eluate. The diacyl penicillins may be de-esterified, to the corresponding penicillanic acid; dephenylacetylation of the latter provides a means for preparing useful isoxazolyl penicillins.
GB06961/70A 1969-04-11 1970-04-09 Novel diacyl penicillins and process for their production Expired GB1284974A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2839569 1969-04-11

Publications (1)

Publication Number Publication Date
GB1284974A true GB1284974A (en) 1972-08-09

Family

ID=12247455

Family Applications (1)

Application Number Title Priority Date Filing Date
GB06961/70A Expired GB1284974A (en) 1969-04-11 1970-04-09 Novel diacyl penicillins and process for their production

Country Status (11)

Country Link
AT (1) AT297928B (en)
BE (1) BE748774A (en)
CH (1) CH553812A (en)
CS (1) CS160125B2 (en)
DE (1) DE2016892A1 (en)
FR (1) FR2043154A5 (en)
GB (1) GB1284974A (en)
NL (1) NL7005198A (en)
PL (1) PL80598B1 (en)
RO (1) RO56560A (en)
SE (1) SE373590B (en)

Also Published As

Publication number Publication date
FR2043154A5 (en) 1971-02-12
DE2016892A1 (en) 1970-10-22
BE748774A (en) 1970-09-16
CH553812A (en) 1974-09-13
SE373590B (en) 1975-02-10
CS160125B2 (en) 1975-02-28
NL7005198A (en) 1970-10-13
PL80598B1 (en) 1975-08-30
AT297928B (en) 1972-04-10
RO56560A (en) 1974-09-01

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees