IE40644B1 - N-deacylation of 7-acylamido-3-hydroxymethyl cephalosporins - Google Patents
N-deacylation of 7-acylamido-3-hydroxymethyl cephalosporinsInfo
- Publication number
- IE40644B1 IE40644B1 IE1626/74A IE162674A IE40644B1 IE 40644 B1 IE40644 B1 IE 40644B1 IE 1626/74 A IE1626/74 A IE 1626/74A IE 162674 A IE162674 A IE 162674A IE 40644 B1 IE40644 B1 IE 40644B1
- Authority
- IE
- Ireland
- Prior art keywords
- acylamido
- deacylation
- group
- iminoether
- imide
- Prior art date
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.
[GB1459212A]
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 (2)
| Publication Number | Publication Date |
|---|---|
| IE40644L IE40644L (en) | 1975-02-01 |
| IE40644B1 true IE40644B1 (en) | 1979-07-18 |
Family
ID=10388710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1626/74A IE40644B1 (en) | 1973-08-01 | 1974-07-31 | N-deacylation of 7-acylamido-3-hydroxymethyl 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 |
| ES428800A1 (en) | 1976-12-01 |
| 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 |
| 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 |
|---|---|---|
| CA1035787A (en) | Process for the production of malonic acid dinitrile | |
| 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 | |
| HK8385A (en) | Novel process for producing 7-(substituted)amino-3-substituted thiomethyl-δ 3-cephem-4-carboxylic acids | |
| CH608809A5 (en) | Process for the preparation of novel cephem derivatives | |
| IE40644B1 (en) | N-deacylation of 7-acylamido-3-hydroxymethyl cephalosporins | |
| IE40217B1 (en) | Process for the preparation of chorinated phenylhydroxylammines | |
| CA1022542A (en) | Process for the manufacture of methylene compounds | |
| CA1018786A (en) | Manufacture of fur articles | |
| CA1035100A (en) | Process for the production of fine-cell foams | |
| IE40926B1 (en) | Cephalosporin compounds and processes and compounds for their production | |
| FR2395255A1 (en) | NEW CATALYSTS USEFUL IN PARTICULAR IN THE PREPARATION OF POLYURETHANE FOAMS | |
| CA1025635A (en) | Process for the manufacture of high-purity lithlium hexafluoroarsenate | |
| IE35985B1 (en) | 6-aminopenicillanic acid derivatives and a process for the manufacture thereof | |
| CA1022283A (en) | Process for the production of aminoplast moulding compositions | |
| CA1028323A (en) | Process for preparing rifamycin s by hydrolysis of rifamycin o | |
| IE42191L (en) | 7ó-methoxy cephalosporin compounds. | |
| IE39233L (en) | Pyridino-dibenzo-azepine,-diazepine, -oxazepine and¹-thiazepine derivatives | |
| CA1008845A (en) | Process of manufacture of new derivatives of the cephalosporine family | |
| IE39591B1 (en) | Shaped articles made of acrylonitrile polymers containing antistatic additves | |
| CA1026377A (en) | Process for the preparation of oxamide | |
| IE41797L (en) | Sulphur-containing hydroxy aliphatic compounds | |
| CA1035782A (en) | Process for the preparation of benorilate | |
| CA1032099A (en) | Process for preparing 6-aminopenicillanic acid |