GB1217143A - Penicillins - Google Patents

Penicillins

Info

Publication number
GB1217143A
GB1217143A GB668467A GB668467A GB1217143A GB 1217143 A GB1217143 A GB 1217143A GB 668467 A GB668467 A GB 668467A GB 668467 A GB668467 A GB 668467A GB 1217143 A GB1217143 A GB 1217143A
Authority
GB
United Kingdom
Prior art keywords
ester
formula
penicillin
group
rco
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
GB668467A
Inventor
Martin Cole
Frank Peter Doyle
Maurice John Soulal
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 Beecham Group PLC filed Critical Beecham Group PLC
Priority to GB668467A priority Critical patent/GB1217143A/en
Priority to BE710202D priority patent/BE710202A/xx
Priority to DE19681670313 priority patent/DE1670313A1/en
Priority to NL6801919A priority patent/NL6801919A/xx
Priority to FR1564647D priority patent/FR1564647A/fr
Priority to ES350402A priority patent/ES350402A1/en
Priority to CH213468A priority patent/CH496731A/en
Publication of GB1217143A publication Critical patent/GB1217143A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

1,217,143. Penicillin esters. BEECHAM GROUP Ltd. 12 Feb., 1968 [13 Feb., 1967], No. 6684/67. Heading C2A. Penicillin esters of general Formula I wherein RCO- is an organic acyl radical and R<SP>11</SP> is an organic ester group that can be removed under mild conditions without distruction of the penicillin nucleus, chemically or enzymatically using an esterase which does not affect the acyl group of the 6-acylamino side chain, are prepared by a process which comprises subjecting a penicillin ester of Formula II wherein R<SP>1</SP>CO is an organic radical different from RCO- in Formula I either to the action of a deacylase enzyme which does not affect the ester group R<SP>11</SP> or to the action of reagents that form a 6-imino ether and treating this ether with a hydroxylic reagent to give a 6- aminopenicillanic acid ester of Formula III and then acylating this ester with an acid of formula R.CO-OH, wherein RCO- is as defined above. R<SP>1</SP>CO of Formula II is preferably the 6-acyl group of a natural penicillin, e.g. benzyl, 2- thienylmethyl or 2-furylmethyl. The ester group R<SP>11</SP> may be alkoxyalkyl, acyloxyalkyl, benzyl, cyanomethyl, phenacyl or substituted phenacyl. The acylation of the 6-APA ester is by means of the aforesaid acid, or a reactive derivative thereof, e.g. halide.
GB668467A 1967-02-13 1967-02-13 Penicillins Expired GB1217143A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
GB668467A GB1217143A (en) 1967-02-13 1967-02-13 Penicillins
BE710202D BE710202A (en) 1967-02-13 1968-02-01
DE19681670313 DE1670313A1 (en) 1967-02-13 1968-02-08 Process for the production of penicillins
NL6801919A NL6801919A (en) 1967-02-13 1968-02-09
FR1564647D FR1564647A (en) 1967-02-13 1968-02-12
ES350402A ES350402A1 (en) 1967-02-13 1968-02-12 Penicillins
CH213468A CH496731A (en) 1967-02-13 1968-02-13 Process for the production of penicillins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB668467A GB1217143A (en) 1967-02-13 1967-02-13 Penicillins

Publications (1)

Publication Number Publication Date
GB1217143A true GB1217143A (en) 1970-12-31

Family

ID=9818917

Family Applications (1)

Application Number Title Priority Date Filing Date
GB668467A Expired GB1217143A (en) 1967-02-13 1967-02-13 Penicillins

Country Status (7)

Country Link
BE (1) BE710202A (en)
CH (1) CH496731A (en)
DE (1) DE1670313A1 (en)
ES (1) ES350402A1 (en)
FR (1) FR1564647A (en)
GB (1) GB1217143A (en)
NL (1) NL6801919A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3996236A (en) * 1973-03-24 1976-12-07 Bristol-Myers Company Methoxymethyl D-6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)penicillanate
US4185015A (en) * 1975-02-11 1980-01-22 Bristol-Myers Company Methoxymethyl 6-[D-2,2-dimethyl-4-(4-hydroxyphenyl)-5-oxo-1-imidazolyl]penicillanate
EP0051481A1 (en) * 1980-11-05 1982-05-12 Beecham Group Plc Process for the preparation of penicillins and penicillin derivatives
CN111909067A (en) * 2020-08-28 2020-11-10 浙江凯普化工有限公司 Organic total synthesis method of D-penicillamine

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2141796T3 (en) * 1993-08-05 2000-04-01 Dsm Nv NEW USE OF PENICILLIN ACILASE G FROM ALCALIGENES FAECALIS.

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3996236A (en) * 1973-03-24 1976-12-07 Bristol-Myers Company Methoxymethyl D-6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)penicillanate
US4185015A (en) * 1975-02-11 1980-01-22 Bristol-Myers Company Methoxymethyl 6-[D-2,2-dimethyl-4-(4-hydroxyphenyl)-5-oxo-1-imidazolyl]penicillanate
EP0051481A1 (en) * 1980-11-05 1982-05-12 Beecham Group Plc Process for the preparation of penicillins and penicillin derivatives
CN111909067A (en) * 2020-08-28 2020-11-10 浙江凯普化工有限公司 Organic total synthesis method of D-penicillamine
CN111909067B (en) * 2020-08-28 2022-03-15 浙江凯普化工有限公司 Organic total synthesis method of D-penicillamine

Also Published As

Publication number Publication date
BE710202A (en) 1968-08-01
DE1670313A1 (en) 1970-07-16
NL6801919A (en) 1968-08-14
ES350402A1 (en) 1969-05-01
FR1564647A (en) 1969-04-25
CH496731A (en) 1970-09-30

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