GB1459212A - N-deacylation of 7-acylamido-3-hydroxy-methyl cephalosporins - Google Patents

N-deacylation of 7-acylamido-3-hydroxy-methyl cephalosporins

Info

Publication number
GB1459212A
GB1459212A GB3649773A GB3649773A GB1459212A GB 1459212 A GB1459212 A GB 1459212A GB 3649773 A GB3649773 A GB 3649773A GB 3649773 A GB3649773 A GB 3649773A GB 1459212 A GB1459212 A GB 1459212A
Authority
GB
United Kingdom
Prior art keywords
acylamido
deacylation
group
hydroxy
iminoether
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
GB3649773A
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories Ltd
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 Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Priority to GB3649773A priority Critical patent/GB1459212A/en
Priority to DE2436771A priority patent/DE2436771C2/en
Priority to IE1626/74A priority patent/IE40644B1/en
Priority to SE7409887A priority patent/SE431754B/en
Priority to CH1051974A priority patent/CH614958A5/en
Priority to AT628474A priority patent/AT338973B/en
Priority to ES428800A priority patent/ES428800A1/en
Priority to JP49087088A priority patent/JPS6326112B2/ja
Priority to AU71881/74A priority patent/AU486903B2/en
Priority to FR7426657A priority patent/FR2254574B1/fr
Priority to NL7410295A priority patent/NL7410295A/en
Priority to DK408774A priority patent/DK146853C/en
Priority to ZA00744904A priority patent/ZA744904B/en
Priority to BE147179A priority patent/BE818366A/en
Publication of GB1459212A publication Critical patent/GB1459212A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

A process for the N-deacylation of 7-acylamido-3-hydroxymethylcephalosporins, in which, in a multi-stage process, the 7-amino group is liberated and the hydroxyl group in the 3-hydroxymethyl group is replaced by a halogen atom. First, the starting compound is reacted with an imide-halide-forming reagent in the presence of a base and thereafter the imide-halide formed is reacted with an iminoether-forming compound, after which the iminoether thus obtained is cleaved hydrolytically. The products of the process may be used as starting material or as precursors for the preparation of antibiotically active cephalosporins. To prepare cephaloridine and cefalozine, the product of the process is first N-acylated in an appropriate manner, after which the halogen atom in the 3-halogenomethyl group is replaced by the appropriate radical.
GB3649773A 1973-08-01 1973-08-01 N-deacylation of 7-acylamido-3-hydroxy-methyl cephalosporins Expired GB1459212A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
GB3649773A GB1459212A (en) 1973-08-01 1973-08-01 N-deacylation of 7-acylamido-3-hydroxy-methyl cephalosporins
DE2436771A DE2436771C2 (en) 1973-08-01 1974-07-31 Process for the N-deacylation of 7-acylamido-3-hydroxymethyl-cephalosporin compounds
IE1626/74A IE40644B1 (en) 1973-08-01 1974-07-31 N-deacylation of 7-acylamido-3-hydroxymethyl cephalosporins
SE7409887A SE431754B (en) 1973-08-01 1974-07-31 PROCEDURE FOR N-DEACYLATION OF ESTARS OF 7-ACYLAMIDO-3-HYDROXMETHYLECEF-3-EM-4-CARBOXYLIC ACID TO ESTARS OF 7-AMINO-3-CHLORMETHYLECEF-3-EM-4-CARBOXYLIC ACID
CH1051974A CH614958A5 (en) 1973-08-01 1974-07-31 Process for the N-deacylation of 7-acylamido-3-hydroxymethylcephalosporins
AT628474A AT338973B (en) 1973-08-01 1974-07-31 PROCESS FOR THE PRODUCTION OF 7-AMINO-3-HALOGENMETHYL CEPHALOSPORANIC ACID ESTERS
ES428800A ES428800A1 (en) 1973-08-01 1974-07-31 N-deacylation of 7-acylamido-3-hydroxy-methyl cephalosporins
JP49087088A JPS6326112B2 (en) 1973-08-01 1974-07-31
AU71881/74A AU486903B2 (en) 1973-08-01 1974-07-31 Improvements in or relating to cephalospirin compounds
FR7426657A FR2254574B1 (en) 1973-08-01 1974-07-31
NL7410295A NL7410295A (en) 1973-08-01 1974-07-31 METHOD OF N-DEACYLATION OF A 7-ACYL-AMIDO-3-HYDROXYMETHYLCEPHALOSPORIN COMPOUND.
DK408774A DK146853C (en) 1973-08-01 1974-07-31 PROCEDURE FOR N-DEACYLATION OF 7-ACYLAMIDO-3-HYDROXYMETHYL CEPHALOSPORIN COMPOUNDS FOR THE CREATION OF 7-AMINO-3-CHLORMETHYLPHALOSPORINES
ZA00744904A ZA744904B (en) 1973-08-01 1974-07-31 Improvements in or relating to cephalosporin compounds
BE147179A BE818366A (en) 1973-08-01 1974-08-01 PROCESS FOR DEACYLATION OF THE AMINE GROUP OF CEPHALOSPORINS

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3649773A GB1459212A (en) 1973-08-01 1973-08-01 N-deacylation of 7-acylamido-3-hydroxy-methyl cephalosporins

Publications (1)

Publication Number Publication Date
GB1459212A true GB1459212A (en) 1976-12-22

Family

ID=10388710

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3649773A Expired GB1459212A (en) 1973-08-01 1973-08-01 N-deacylation of 7-acylamido-3-hydroxy-methyl cephalosporins

Country Status (13)

Country Link
JP (1) JPS6326112B2 (en)
AT (1) AT338973B (en)
BE (1) BE818366A (en)
CH (1) CH614958A5 (en)
DE (1) DE2436771C2 (en)
DK (1) DK146853C (en)
ES (1) ES428800A1 (en)
FR (1) FR2254574B1 (en)
GB (1) GB1459212A (en)
IE (1) IE40644B1 (en)
NL (1) NL7410295A (en)
SE (1) SE431754B (en)
ZA (1) ZA744904B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0238060B1 (en) 1986-03-19 1992-01-08 Banyu Pharmaceutical Co., Ltd. Cephalosporin derivatives, processes for their preparation and antibacterial agents
JP4659959B2 (en) * 2000-09-29 2011-03-30 大塚化学株式会社 3-CEPHEM COMPOUND AND PROCESS FOR PRODUCING THE SAME

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK118506B (en) * 1963-02-18 1970-08-31 Ciba Geigy Process for the preparation of 7-aminocephalosporanic acid or esters thereof.
GB1241657A (en) * 1967-08-21 1971-08-04 Glaxo Lab Ltd Improvements in or relating to cephalosporin compounds

Also Published As

Publication number Publication date
CH614958A5 (en) 1979-12-28
JPS5076089A (en) 1975-06-21
BE818366A (en) 1975-02-03
DK146853B (en) 1984-01-23
AU7188174A (en) 1976-02-05
ATA628474A (en) 1977-01-15
JPS6326112B2 (en) 1988-05-27
SE7409887L (en) 1975-02-03
SE431754B (en) 1984-02-27
DK408774A (en) 1975-04-01
DE2436771A1 (en) 1975-02-20
AT338973B (en) 1977-09-26
FR2254574B1 (en) 1977-10-14
IE40644L (en) 1975-02-01
DE2436771C2 (en) 1985-10-10
DK146853C (en) 1984-08-06
FR2254574A1 (en) 1975-07-11
ES428800A1 (en) 1976-12-01
NL7410295A (en) 1975-02-04
ZA744904B (en) 1975-08-27
IE40644B1 (en) 1979-07-18

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PCNP Patent ceased through non-payment of renewal fee