GB727481A - Improvements in or relating to the preparation of esters and amides of penicillin g and penicillin x - Google Patents
Improvements in or relating to the preparation of esters and amides of penicillin g and penicillin xInfo
- Publication number
- GB727481A GB727481A GB538452A GB538452A GB727481A GB 727481 A GB727481 A GB 727481A GB 538452 A GB538452 A GB 538452A GB 538452 A GB538452 A GB 538452A GB 727481 A GB727481 A GB 727481A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzyl
- penicillin
- penicillinate
- benzyl penicillin
- anhydride
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
An intermediate in the preparation of esters and amides of penicillin G and X, has the formula <FORM:0727481/IV (b)/1> where R1 is hydrogen or hydroxyl and R2 is alkyl, aralkyl or aryl. It is prepared by reacting a penicillin salt with a chloroformic ester in an inert solvent. For salts with metals e.g. sodium or potassium penicillin, preferred solvents are water-miscible e.g. acetone, dioxan and tetrahydrofuran and may contain up to 30 per cent of water. For salts with organic bases e.g. salts of tertiary amines such as triethylamine and N-ethylpiperidine, specified solvents are chloroform, ethyl acetate, acetone or ether. It is preferred that R2 be 1 to 4 carbon alkyl e.g. methyl, ethyl, propyl or butyl, or a benzyl group. Esters are produced by reacting a compound of the above general formula with a hydroxylic compound in an inert solvent under basic conditions i.e. in the presence of a tertiary amine such as pyridine, dimethyl aniline or triethylamine or by the use of a hydroxylic compound which itself contains a tertiary amino group. Amides are produced by reacting compounds of the above general formula with a primary or secondary amine. The said intermediate product need not be isolated. The preparation of the following is described: (a) methylbenzylpenicillinate (b) phenylbenzyl penicillinate (3) 2-diethyl aminoethyl benzyl penicillinate (d) benzyl penicillin cyclohexylamide (e) benzyl penicillin 2 : 2-dimethyl cyclohexylamide (f) benzylpenicillin p-toluidide (g) benzyl penicillin morphalide (h) benzyl penicillin - diethylaminoethylamide (i) benzyl penicillin ethanolamide (j) benzyl penicillin carbethoxyanhydride (k) benzyl penicillin p - amidobenzoic acid (l) benzyl penicillin carbobenzyloxy anhydride (m) furfuryl benzyl penicillinate (n) benzyl penicillin carboisobutyloxyanhydride (o) benzyl penicillin carboisopropyloxy anhydride (p) benzyl penicillin carbomethoxy anhydride (q) 3-morpholinoprop - 2 - yl benzyl penicillinate (r) N-ethyl diethanolamine bis-benzyl-penicillinate.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB538452A GB727481A (en) | 1952-02-29 | 1952-02-29 | Improvements in or relating to the preparation of esters and amides of penicillin g and penicillin x |
| ES0208018A ES208018A1 (en) | 1952-02-29 | 1953-02-27 | Improvements in or relating to the preparation of esters and amides of penicillin g and penicillin x |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB538452A GB727481A (en) | 1952-02-29 | 1952-02-29 | Improvements in or relating to the preparation of esters and amides of penicillin g and penicillin x |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB727481A true GB727481A (en) | 1955-04-06 |
Family
ID=9795130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB538452A Expired GB727481A (en) | 1952-02-29 | 1952-02-29 | Improvements in or relating to the preparation of esters and amides of penicillin g and penicillin x |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES208018A1 (en) |
| GB (1) | GB727481A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4081546A (en) * | 1976-06-24 | 1978-03-28 | Beecham Group Limited | 3-substituted aminocycloalkyl esters of penicillin antibiotics |
-
1952
- 1952-02-29 GB GB538452A patent/GB727481A/en not_active Expired
-
1953
- 1953-02-27 ES ES0208018A patent/ES208018A1/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4081546A (en) * | 1976-06-24 | 1978-03-28 | Beecham Group Limited | 3-substituted aminocycloalkyl esters of penicillin antibiotics |
Also Published As
| Publication number | Publication date |
|---|---|
| ES208018A1 (en) | 1953-11-01 |
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