GB1459212A - N-deacylation of 7-acylamido-3-hydroxy-methyl cephalosporins - Google Patents
N-deacylation of 7-acylamido-3-hydroxy-methyl cephalosporinsInfo
- 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
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.
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)
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)
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 |
-
1973
- 1973-08-01 GB GB3649773A patent/GB1459212A/en not_active Expired
-
1974
- 1974-07-31 NL NL7410295A patent/NL7410295A/en not_active Application Discontinuation
- 1974-07-31 ZA ZA00744904A patent/ZA744904B/en unknown
- 1974-07-31 JP JP49087088A patent/JPS6326112B2/ja not_active Expired
- 1974-07-31 CH CH1051974A patent/CH614958A5/en not_active IP Right Cessation
- 1974-07-31 ES ES428800A patent/ES428800A1/en not_active Expired
- 1974-07-31 FR FR7426657A patent/FR2254574B1/fr not_active Expired
- 1974-07-31 DE DE2436771A patent/DE2436771C2/en not_active Expired
- 1974-07-31 DK DK408774A patent/DK146853C/en not_active IP Right Cessation
- 1974-07-31 IE IE1626/74A patent/IE40644B1/en unknown
- 1974-07-31 SE SE7409887A patent/SE431754B/en unknown
- 1974-07-31 AT AT628474A patent/AT338973B/en not_active IP Right Cessation
- 1974-08-01 BE BE147179A patent/BE818366A/en not_active IP Right Cessation
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 |