ES428800A1 - N-deacylation of 7-acylamido-3-hydroxy-methyl cephalosporins - Google Patents
N-deacylation of 7-acylamido-3-hydroxy-methyl cephalosporinsInfo
- Publication number
- ES428800A1 ES428800A1 ES428800A ES428800A ES428800A1 ES 428800 A1 ES428800 A1 ES 428800A1 ES 428800 A ES428800 A ES 428800A ES 428800 A ES428800 A ES 428800A ES 428800 A1 ES428800 A1 ES 428800A1
- Authority
- ES
- Spain
- 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
- 229930186147 Cephalosporin Natural products 0.000 title abstract 2
- 229940124587 cephalosporin Drugs 0.000 title abstract 2
- 238000005947 deacylation reaction Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 abstract 1
- 229960003866 cefaloridine Drugs 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
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.
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 |
|---|---|
| ES428800A1 true ES428800A1 (en) | 1976-12-01 |
Family
ID=10388710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES428800A Expired ES428800A1 (en) | 1973-08-01 | 1974-07-31 | 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 AT AT628474A patent/AT338973B/en not_active IP Right Cessation
- 1974-07-31 NL NL7410295A patent/NL7410295A/en not_active Application Discontinuation
- 1974-07-31 IE IE1626/74A patent/IE40644B1/en unknown
- 1974-07-31 ZA ZA00744904A patent/ZA744904B/en unknown
- 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 CH CH1051974A patent/CH614958A5/en not_active IP Right Cessation
- 1974-07-31 DK DK408774A patent/DK146853C/en not_active IP Right Cessation
- 1974-07-31 SE SE7409887A patent/SE431754B/en unknown
- 1974-07-31 JP JP49087088A patent/JPS6326112B2/ja not_active Expired
- 1974-07-31 ES ES428800A patent/ES428800A1/en not_active Expired
- 1974-08-01 BE BE147179A patent/BE818366A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1459212A (en) | 1976-12-22 |
| JPS6326112B2 (en) | 1988-05-27 |
| AT338973B (en) | 1977-09-26 |
| DK146853C (en) | 1984-08-06 |
| IE40644L (en) | 1975-02-01 |
| JPS5076089A (en) | 1975-06-21 |
| IE40644B1 (en) | 1979-07-18 |
| DK408774A (en) | 1975-04-01 |
| SE7409887L (en) | 1975-02-03 |
| FR2254574B1 (en) | 1977-10-14 |
| ATA628474A (en) | 1977-01-15 |
| ZA744904B (en) | 1975-08-27 |
| NL7410295A (en) | 1975-02-04 |
| SE431754B (en) | 1984-02-27 |
| BE818366A (en) | 1975-02-03 |
| FR2254574A1 (en) | 1975-07-11 |
| DK146853B (en) | 1984-01-23 |
| DE2436771A1 (en) | 1975-02-20 |
| CH614958A5 (en) | 1979-12-28 |
| DE2436771C2 (en) | 1985-10-10 |
| AU7188174A (en) | 1976-02-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1032549A (en) | Process for the production of ferrocene derivatives | |
| CH610902A5 (en) | Process for the preparation of cephalosporanic acid derivatives | |
| EG11104A (en) | Process for preparation of alpha-aminoacyl-3-halo cephalosporins | |
| CH608809A5 (en) | Process for the preparation of novel cephem derivatives | |
| ES405276A1 (en) | Pyrimidinylphrazolone derivative and process of preparing the same | |
| ES428800A1 (en) | N-deacylation of 7-acylamido-3-hydroxy-methyl cephalosporins | |
| IE40217B1 (en) | Process for the preparation of chorinated phenylhydroxylammines | |
| ES441404A1 (en) | Process of preparing 5-fluoro-2-methyl-1-(paramethylsulfinylbenzylidene)-indenyl-3-acetic acid | |
| CA1018786A (en) | Manufacture of fur articles | |
| CA1022542A (en) | Process for the manufacture of methylene compounds | |
| EG11847A (en) | Process for preparing of novel acid derivatives | |
| EG11596A (en) | Process for preparing of cephem derivatives | |
| CH609041A5 (en) | Process for the preparation of novel benzylamines | |
| ES428969A1 (en) | 2,2,2-Trifluoro-1-chloroethyl ethers and process for preparing them | |
| CA1035100A (en) | Process for the production of fine-cell foams | |
| ES449699A1 (en) | Anti-allergic-3-carboxy-isocoumarin compositions and methods of use | |
| FR2395255A1 (en) | NEW CATALYSTS USEFUL IN PARTICULAR IN THE PREPARATION OF POLYURETHANE FOAMS | |
| ES404463A1 (en) | 6-Hydroxy-dihydro-uracils, process for their preparation | |
| CS189625B2 (en) | Process for preparing 3-halogenderivatives of cephalosporine | |
| IE39591B1 (en) | Shaped articles made of acrylonitrile polymers containing antistatic additves | |
| CA1008845A (en) | Process of manufacture of new derivatives of the cephalosporine family | |
| GB1408500A (en) | Manufacture of articles moulded from sheet moulding compounds | |
| AU7998475A (en) | Process for the manufacture of cephalosporins having an alpha-acyloxyacetic acid side chain | |
| HU168439B (en) | Process for production of modified dienpolimers | |
| NL154227B (en) | PROCESS FOR PREPARATION OF BUTYL RUBBER AS WELL AS MOLDED PRODUCT. |