GB1244679A - Preparation of isoxazolyl penicillins - Google Patents

Preparation of isoxazolyl penicillins

Info

Publication number
GB1244679A
GB1244679A GB42890/69A GB4289069A GB1244679A GB 1244679 A GB1244679 A GB 1244679A GB 42890/69 A GB42890/69 A GB 42890/69A GB 4289069 A GB4289069 A GB 4289069A GB 1244679 A GB1244679 A GB 1244679A
Authority
GB
United Kingdom
Prior art keywords
penicillin
general formula
group
isoxazolyl
aug
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
GB42890/69A
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 GB1244679A publication Critical patent/GB1244679A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic 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
    • 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)
  • 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)

Abstract

1,244,679. Isoxazolyl penicillins. TOYO JOZO K.K. 28 Aug., 1969 [28 Aug., 1968; 12 April,. 1969; 31 May, 1969; 28 June, 1969], No. 42890/69. Heading C2A. Isoxazolyl penicillins of the general formula wherein R represents H or a C 1 -C 4 alkyl radical, and R 1 and R 2 , which may be the same or different, are H or halogen atoms, and the non-toxic salts of the compounds in which R is H, are prepared by reacting a penicillin G ester of the general formula in which R<SP>1</SP> is a protective group for the carboxyl group which is either an alkyl radical R or a group which can be easily eliminated without having a detrimental effect on the structure of the penicillin, with a chlorinating agent in the presence of a tertiary organic amine to give a compound of the general formula which is reacted with an isoxazolyl carboxylate of formula in which M represents a metal atom, to give a diacyl penicillin ester of general formula which is then subjected to dephenylacetylation, whereafter, when R<SP>1</SP> is a group capable of being easily eliminated without having a detrimental effect on the structure of the penicillin, the resulting product is so treated in order to eliminate the protective group from the carboxyl group, and the free acid thus obtained is, if desired, neutralized with a non-toxic inorganic or organic base.
GB42890/69A 1968-08-28 1969-08-28 Preparation of isoxazolyl penicillins Expired GB1244679A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP6197568 1968-08-28
JP2840169 1969-04-12
JP4274569 1969-05-31
JP5115069 1969-06-28

Publications (1)

Publication Number Publication Date
GB1244679A true GB1244679A (en) 1971-09-02

Family

ID=27458875

Family Applications (1)

Application Number Title Priority Date Filing Date
GB42890/69A Expired GB1244679A (en) 1968-08-28 1969-08-28 Preparation of isoxazolyl penicillins

Country Status (9)

Country Link
AT (1) AT291439B (en)
CH (1) CH543540A (en)
CS (1) CS167252B2 (en)
DE (1) DE1943667C3 (en)
DK (1) DK135535B (en)
FR (1) FR2017073A1 (en)
GB (1) GB1244679A (en)
HU (1) HU162501B (en)
NL (1) NL6913158A (en)

Also Published As

Publication number Publication date
AT291439B (en) 1971-07-12
NL6913158A (en) 1970-03-03
DE1943667B2 (en) 1979-04-12
DE1943667C3 (en) 1979-11-29
CH543540A (en) 1973-10-31
FR2017073A1 (en) 1970-05-15
CS167252B2 (en) 1976-04-29
DK135535B (en) 1977-05-16
DE1943667A1 (en) 1970-05-14
HU162501B (en) 1973-02-28
DK135535C (en) 1977-10-24

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