GB1339605A - Penicillin synthesis - Google Patents

Penicillin synthesis

Info

Publication number
GB1339605A
GB1339605A GB1339605DA GB1339605A GB 1339605 A GB1339605 A GB 1339605A GB 1339605D A GB1339605D A GB 1339605DA GB 1339605 A GB1339605 A GB 1339605A
Authority
GB
United Kingdom
Prior art keywords
acid
derivative
amino
silylated
compounds
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
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
Publication of GB1339605A publication Critical patent/GB1339605A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1339605 Preparation of α-amino-(p-hydroxybenzyl) penicillins BEECHAM GROUP Ltd 28 March 1972 [1 April 1971] 8460/71 Heading C2A A process for the preparation of compounds of Formula I and salts thereof comprises reacting a silylated derivative of 6-aminopenicillanic acid with a reactive derivative of α-amino-p-hydroxyphenylacetic acid in which the amino group is protected, and thereafter removing the silyl groups by hydrolysis or alcoholysis. The silylated derivative of 6-aminopenicillanic acid may be the product of reaction between 6-aminopenicillanic acid or a salt thereof and a halotrialkylsilane, dihalodialkylsilane, halotrialkoxysilane, dihalodialkoxysilane or corresponding aryl or aralkyl silanes. Preferred silylated derivatives of 6-APA are compounds of Formula II wherein R 1 , R 2 and R 3 are each alkyl or aryl groups. The reactive derivative of α-amino-phydroxyphenylacetic acid may be an activated ester, an acid chloride, bromide or anhydride or the derivative obtained from the acid and a carbodiimide or N,N<SP>1</SP>-carbonyldiimidazole. Preferred reactive derivatives are those of Formulae III, IV and V.
GB1339605D 1972-03-28 1972-03-28 Penicillin synthesis Expired GB1339605A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB846071 1972-03-28

Publications (1)

Publication Number Publication Date
GB1339605A true GB1339605A (en) 1973-12-05

Family

ID=9852898

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1339605D Expired GB1339605A (en) 1972-03-28 1972-03-28 Penicillin synthesis

Country Status (2)

Country Link
ES (1) ES401263A1 (en)
GB (1) GB1339605A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3980637A (en) * 1975-03-17 1976-09-14 Bristol-Myers Company Production of amoxicillin
DE2732528A1 (en) * 1976-07-20 1978-01-26 Bristol Myers Co PROCESS FOR THE PRODUCTION OF AMOXICILLIN TRIHYDRATE
DE2822876A1 (en) * 1977-06-04 1978-12-14 Antibioticos Sa PROCESS FOR THE PRODUCTION OF HYDROXY-ALPHA-AMINOBENZYLPENICILLIN
US4240960A (en) * 1979-03-19 1980-12-23 Bristol-Myers Company Trimethylsilyl substituted penicillins
US4278600A (en) 1979-03-19 1981-07-14 Bristol-Myers Company Production of penicillins
US4310458A (en) 1979-03-19 1982-01-12 Bristol-Myers Company Production of penicillins
US4351766A (en) * 1979-07-12 1982-09-28 Bristol-Myers Company Production of penicillins
EP0197294A2 (en) 1985-03-16 1986-10-15 Bayer Ag Beta-lactam antibiotics, process for their preparation and their use as medicaments
DK151024B (en) * 1977-09-06 1987-10-12 Gist Brocades Nv METHOD FOR PREPARING 6- (D-ALFA-AMINO- (P-HYDROXYPHENYL) ACETIMIDO) -PENICILLANIC ACID
US7230097B2 (en) 2003-03-10 2007-06-12 Lupin Ltd. Process for preparation of 7-[α-Amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3980637A (en) * 1975-03-17 1976-09-14 Bristol-Myers Company Production of amoxicillin
DE2732528A1 (en) * 1976-07-20 1978-01-26 Bristol Myers Co PROCESS FOR THE PRODUCTION OF AMOXICILLIN TRIHYDRATE
DE2822876A1 (en) * 1977-06-04 1978-12-14 Antibioticos Sa PROCESS FOR THE PRODUCTION OF HYDROXY-ALPHA-AMINOBENZYLPENICILLIN
FR2392997A1 (en) * 1977-06-04 1978-12-29 Antibioticos Sa PROCESS FOR THE PREPARATION OF HYDROXY-A-AMINOBENZYLPENICILLINS
DK151024B (en) * 1977-09-06 1987-10-12 Gist Brocades Nv METHOD FOR PREPARING 6- (D-ALFA-AMINO- (P-HYDROXYPHENYL) ACETIMIDO) -PENICILLANIC ACID
US4240960A (en) * 1979-03-19 1980-12-23 Bristol-Myers Company Trimethylsilyl substituted penicillins
US4278600A (en) 1979-03-19 1981-07-14 Bristol-Myers Company Production of penicillins
US4310458A (en) 1979-03-19 1982-01-12 Bristol-Myers Company Production of penicillins
US4351766A (en) * 1979-07-12 1982-09-28 Bristol-Myers Company Production of penicillins
EP0197294A2 (en) 1985-03-16 1986-10-15 Bayer Ag Beta-lactam antibiotics, process for their preparation and their use as medicaments
US7230097B2 (en) 2003-03-10 2007-06-12 Lupin Ltd. Process for preparation of 7-[α-Amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid
US7427692B2 (en) 2003-03-10 2008-09-23 Lupin Ltd. Process for preparation of 7-[α-amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid

Also Published As

Publication number Publication date
ES401263A1 (en) 1975-02-16

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years