SE503843C2 - Process for the preparation of the 1-ethoxycarbonyloxyethyl ester ab 6- (D (-) - α-amino-α-phenyl-acetamido) -penicillanic acid - Google Patents

Process for the preparation of the 1-ethoxycarbonyloxyethyl ester ab 6- (D (-) - α-amino-α-phenyl-acetamido) -penicillanic acid

Info

Publication number
SE503843C2
SE503843C2 SE9100548A SE9100548A SE503843C2 SE 503843 C2 SE503843 C2 SE 503843C2 SE 9100548 A SE9100548 A SE 9100548A SE 9100548 A SE9100548 A SE 9100548A SE 503843 C2 SE503843 C2 SE 503843C2
Authority
SE
Sweden
Prior art keywords
amino
acetamido
phenyl
preparation
alpha
Prior art date
Application number
SE9100548A
Other languages
Swedish (sv)
Other versions
SE503843C3 (en
SE9100548L (en
SE9100548D0 (en
Inventor
Luigi Ratti
Derek Reginald Palmer
Robert Graham Tyson
Original Assignee
Astra Laekemedel Ab
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
Priority claimed from IT22141/82A external-priority patent/IT1190897B/en
Priority claimed from GB838300331A external-priority patent/GB8300331D0/en
Application filed by Astra Laekemedel Ab filed Critical Astra Laekemedel Ab
Publication of SE503843C3 publication Critical patent/SE503843C3/en
Publication of SE9100548L publication Critical patent/SE9100548L/en
Publication of SE9100548D0 publication Critical patent/SE9100548D0/en
Publication of SE503843C2 publication Critical patent/SE503843C2/en

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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids
    • 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)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

alpha -Bromo diethylcarbonate is used to prepare ethylcarbonyloxyethyl esters of penicillins and caphalosporins. The amino group in ampicillin can first be protected by reaction with an acetoacetate derivative and the protecting group removed after the esterification step. alpha -Bromo diethylcarbonate can be used without an esterification catalyst and is obtained by reacting acetaldehyde with carbonyl bromide followed by reaction with ethanol or by a halogen exchange reaction with the corresponding alpha -chloro compound.
SE9100548A 1982-06-29 1991-02-26 Process for the preparation of the 1-ethoxycarbonyloxyethyl ester ab 6- (D (-) - α-amino-α-phenyl-acetamido) -penicillanic acid SE503843C2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
IT22141/82A IT1190897B (en) 1982-06-29 1982-06-29 PROCEDURE FOR THE PREPARATION OF THE 1-ETHOXYCARBONYLOXYETHYL ACID ACID 6- (D (-) - ALPHA AMINOALPHA-PHENYLACETAMIDE) -PENICILLANIC
GB8226751 1982-09-20
GB8228622 1982-10-06
GB8232629 1982-11-16
GB838300331A GB8300331D0 (en) 1983-01-07 1983-01-07 Preparation of bromo carbonates

Publications (4)

Publication Number Publication Date
SE503843C3 SE503843C3 (en) 1991-02-26
SE9100548L SE9100548L (en) 1991-02-26
SE9100548D0 SE9100548D0 (en) 1991-02-26
SE503843C2 true SE503843C2 (en) 1996-09-16

Family

ID=27516485

Family Applications (2)

Application Number Title Priority Date Filing Date
SE8303414A SE454879B (en) 1982-06-29 1983-06-15 ALFA-BROMODYTHYL CARBONATE AND ITS USE AS INTERMEDIATE IN PENICILLIN G PREPARATION
SE9100548A SE503843C2 (en) 1982-06-29 1991-02-26 Process for the preparation of the 1-ethoxycarbonyloxyethyl ester ab 6- (D (-) - α-amino-α-phenyl-acetamido) -penicillanic acid

Family Applications Before (1)

Application Number Title Priority Date Filing Date
SE8303414A SE454879B (en) 1982-06-29 1983-06-15 ALFA-BROMODYTHYL CARBONATE AND ITS USE AS INTERMEDIATE IN PENICILLIN G PREPARATION

Country Status (23)

Country Link
JP (2) JPH0730082B2 (en)
AT (1) AT383128B (en)
AU (1) AU566803B2 (en)
BG (3) BG37527A3 (en)
CH (2) CH657620B (en)
CY (2) CY1520A (en)
DD (1) DD211561A5 (en)
DE (2) DE3322783A1 (en)
DK (3) DK160039C (en)
FI (1) FI79115C (en)
FR (1) FR2543957B1 (en)
GB (3) GB2168050A (en)
GR (1) GR78585B (en)
HU (1) HU191534B (en)
IE (1) IE56712B1 (en)
IL (1) IL68992A (en)
IS (1) IS1361B6 (en)
NL (1) NL194081C (en)
NO (3) NO157696C (en)
NZ (1) NZ204736A (en)
PT (1) PT76944B (en)
SE (2) SE454879B (en)
YU (2) YU43926B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2573756B1 (en) * 1984-11-23 1987-01-16 Poudres & Explosifs Ste Nale PROCESS FOR THE PREPARATION OF BROMO-1 ETHYL AND HYDROCARBYL CARBONATES AND NOVEL BROMO-1 ETHYL AND HYDROCARBYL CARBONATES

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH516593A (en) * 1967-09-29 1971-12-15 Leo Pharm Prod Ltd Alpha amino-benzyl penicillins - useful as oral antibiotics
US3873521A (en) * 1970-09-17 1975-03-25 Astra Laekemedel Ab Esters of {60 -amino penicillins
IE35648B1 (en) * 1970-09-25 1976-04-14 Beecham Group Ltd Penicillins
DE2161420A1 (en) * 1970-12-30 1972-07-27 Toyama Chemical Co. Ltd., Tokio Penicillin derivatives and processes for their preparation
BE784800A (en) * 1971-06-15 1972-10-02 Yamanouchi Pharma Co Ltd PROCESS FOR PREPARING NEW OXYMETHYL ESTERS OF PENICILLIN AND CEPHALOSPORIN
IL41313A (en) * 1972-02-15 1976-08-31 Harrison Ltd Preparation of the lh-and fsh-releasing hormone and compositions containing it
GB1425571A (en) * 1972-03-13 1976-02-18 Astra Laekemedel Ab Penicillins and cephaosporins
GB1426869A (en) * 1972-03-13 1976-03-03 Astra Laekemedel Ab Penicillins
GB1426717A (en) * 1972-03-13 1976-03-03 Astra Laekemedel Ab Penicillins
SE397981B (en) * 1973-02-19 1977-11-28 Astra Laekemedel Ab NEW TETRAALKYLAMMONIUM SALTS OF 6-AMINOPENICILLANIC ACID AND OF BENZYLPENICILLIN INTENDED TO BE USED AS INTERMEDIATE PRODUCTS IN THE PREPARATION OF CERTAIN ESTERS OF 6-AMINOPENICILLANIC ACID AND OF BENZYLPENIC
GB1565656A (en) * 1975-12-13 1980-04-23 Beecham Group Ltd Preparation of substituted penicillin acid esters
GB1598568A (en) * 1977-04-19 1981-09-23 Glaxo Lab Ltd Esters of(6r,7r)-3-carbamoyloxymethyl-7-((z)-2-(fur-2-yl)-2-methoxyiminoacetamido)-ceph-3-em-4-carboxylic acid
JPS5444694A (en) * 1977-09-06 1979-04-09 Kou Kamata Aminobenzylpenicillin derivative
DE3323462A1 (en) * 1982-06-30 1984-01-12 Glaxo Group Ltd., London CEPHALOSPORINE ANTIBIOTICS
DE3380024D1 (en) * 1982-11-04 1989-07-13 Astra Laekemedel Ab Process for the preparation of the 1'-ethoxycarbonyloxyethyl ester of benzylpenicillin

Also Published As

Publication number Publication date
YU43693B (en) 1989-10-31
IS2825A7 (en) 1984-07-08
DK296683D0 (en) 1983-06-28
BG38336A3 (en) 1985-11-15
GB8522827D0 (en) 1985-10-23
DK105990D0 (en) 1990-04-30
NZ204736A (en) 1986-11-12
DE3348299C2 (en) 1990-12-20
FR2543957A1 (en) 1984-10-12
FI79115C (en) 1989-11-10
NL194081B (en) 2001-02-01
DK106090A (en) 1990-04-30
IE56712B1 (en) 1991-11-20
NL8302286A (en) 1984-01-16
GB2169287A (en) 1986-07-09
CH657620B (en) 1986-09-15
NO851255L (en) 1983-12-30
JPH0730082B2 (en) 1995-04-05
PT76944A (en) 1983-07-01
BG37527A3 (en) 1985-06-14
FR2543957B1 (en) 1986-10-24
JPH0543583A (en) 1993-02-23
DK159821B (en) 1990-12-10
IS1361B6 (en) 1989-05-25
SE8303414L (en) 1983-12-30
FI832363L (en) 1983-12-30
NO832351L (en) 1983-12-30
GR78585B (en) 1984-09-27
GB8528958D0 (en) 1986-01-02
JPH0819052B2 (en) 1996-02-28
DK106090D0 (en) 1990-04-30
GB2168699B (en) 1987-04-15
DE3322783C2 (en) 1991-01-31
GB8522826D0 (en) 1985-10-23
BG38335A3 (en) 1985-11-15
NL194081C (en) 2001-06-05
DK160039B (en) 1991-01-21
GB2168699A (en) 1986-06-25
DK296683A (en) 1983-12-30
SE454879B (en) 1988-06-06
DK167807B1 (en) 1993-12-20
IE831445L (en) 1983-12-29
FI79115B (en) 1989-07-31
AU1632883A (en) 1984-01-05
DD211561A5 (en) 1984-07-18
PT76944B (en) 1986-04-09
NO157696B (en) 1988-01-25
YU141583A (en) 1986-06-30
SE9100548L (en) 1991-02-26
CY1519A (en) 1990-11-16
IL68992A (en) 1991-06-10
SE8303414D0 (en) 1983-06-15
AU566803B2 (en) 1987-10-29
CH656377A5 (en) 1986-06-30
NO851254L (en) 1983-12-30
JPH0717918A (en) 1995-01-20
DK159821C (en) 1991-04-29
NO157696C (en) 1988-05-04
GB2168050A (en) 1986-06-11
YU43926B (en) 1989-12-31
FI832363A0 (en) 1983-06-28
CY1520A (en) 1990-11-16
DE3322783A1 (en) 1984-02-09
YU21886A (en) 1987-10-31
DK160039C (en) 1991-06-10
HU191534B (en) 1987-03-30
SE9100548D0 (en) 1991-02-26
DK105990A (en) 1990-04-30
ATA238483A (en) 1986-10-15
AT383128B (en) 1987-05-25
GB2169287B (en) 1987-04-08

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Legal Events

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NUG Patent has lapsed