GB1341921A - Process for the preparation of semisynthetic penicillins - Google Patents
Process for the preparation of semisynthetic penicillinsInfo
- Publication number
- GB1341921A GB1341921A GB35371A GB1341921DA GB1341921A GB 1341921 A GB1341921 A GB 1341921A GB 35371 A GB35371 A GB 35371A GB 1341921D A GB1341921D A GB 1341921DA GB 1341921 A GB1341921 A GB 1341921A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penicillin
- penicillins
- formula
- acid
- alkali metal
- 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
- 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
- C07D499/04—Preparation
- C07D499/10—Modification of an amino radical directly attached in position 6
- C07D499/12—Acylation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1341921 Preparation of penicillins FABRICA DE ANTIBIOTICE IASI 4 Jan 1971 353/71 Heading C2A A process for the preparation of semisynthetic penicillins of Formulµ I and II: wherein in Formula I R and R 1 are methoxy groups or hydrogen, and R 2 is a nitro group or hydrogen, and in Formula II R is an alkyl, aralkyl or aryl group, by acylating 6-aminopenicillanic acid with the appropriate acid chloride in the case of penicillins of Formula I or with the appropriate mixed anhydride of an N-protected alpha-aminoacid in the case of penicillins of Formula II, wherein the acylation is carried out in solution in an organic solvent using the 6-aminopenicillanic acid in the form of its triethylammonium salt and the triethylammonium salt of the resulting penicillin is extracted with water from the organic solvent. The aqueous extract containing the triethylammonium salt may be acidified with mineral acid in the presence of dichloromethane and the resulting organic phase containing the penicillin in its acid form is separated from the aqueous phase. The separated organic phase containing the penicillin in its acid form may be treated with an aqueous solution of an alkali metal hydroxide and the aqueous phase containing the penicillin in the form of its alkali metal salt is separated from the organic phase. The alkali metal salt of the penicillin may be recovered by spray drying the aqueous solution thereof.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RO6210770 | 1970-01-12 | ||
| GB35371 | 1971-01-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1341921A true GB1341921A (en) | 1973-12-25 |
Family
ID=26235872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35371A Expired GB1341921A (en) | 1970-01-12 | 1971-01-04 | Process for the preparation of semisynthetic penicillins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1341921A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0126351A1 (en) * | 1983-05-19 | 1984-11-28 | Fried. Krupp Gesellschaft mit beschränkter Haftung | Process for the isolation and purification of antibiotics |
-
1971
- 1971-01-04 GB GB35371A patent/GB1341921A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0126351A1 (en) * | 1983-05-19 | 1984-11-28 | Fried. Krupp Gesellschaft mit beschränkter Haftung | Process for the isolation and purification of antibiotics |
| US4581166A (en) * | 1983-05-19 | 1986-04-08 | Fried. Krupp Gesellschaft Mit Beschrankter Haftung | Method for isolating and purifying antibiotics |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |