GB958824A - Improvements in or relating to the production of penicillins - Google Patents
Improvements in or relating to the production of penicillinsInfo
- Publication number
- GB958824A GB958824A GB2892362A GB2892362A GB958824A GB 958824 A GB958824 A GB 958824A GB 2892362 A GB2892362 A GB 2892362A GB 2892362 A GB2892362 A GB 2892362A GB 958824 A GB958824 A GB 958824A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- benzyl
- amino
- formula
- hydrogen
- 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 N-(amino substituted) acyl derivative of a 6-aminopenicillanic acid of formula: <FORM:0958824/C2/1> wherein R3 is hydroxy, C1-C6 alkoxy, benzyl or NR4R5 wherein R4 is hydrogen, C1-C6 alkyl, di (C1-C6) alkylamino C1-C6 alkyl, phenyl, benzyl, phenethyl, cyclohexyl or b -morpholinoethyl, R5 is hydrogen, C1-C6 alkyl, benzyl or cyclohexyl, R4 and R5 when taken together are tetramethylene, pentamethylene, -CH2-CH2-O-CH2-CH2 or -CH2-CH2-NH-CH2-CH2, and X is an amino-substituted acyl group having up to 12 carbon atoms having the formula: <FORM:0958824/C2/2> wherein R1 is hydrogen, phenyl, benzyl, phenethyl, alicyclic, indolyl, pyrollidinyl, alkyl or substituted alkyl wherein the substituent is C1-C6 acyloxy, C1-C6 acylmercapto, C1-C6 alkoxy, C1-C6 alkylmercapto, carbobenzoxy, allylmercapto, benzylmercapto, benzyloxy, C1-C6 acylamino, carbobenzoxamido, carboxy or carboxamido, R2 is hydrogen, C1-C6 alkyl, phenyl, cyclohexyl or benzyl, and R6 is a bivalent alkylene radical having from 4 to 6 carbon atoms which, when taken together with the carbon atom to which it is attached, forms a saturated alicyclic ring having from 5 to 7 carbon atoms, is prepared by reacting a solution in a reaction inert solvent, of the N-carboxy anhydride of an amino acid having the formula: <FORM:0958824/C2/3> with a neutral aqueous solution of 6-aminopenicillanic acid, a C1-C6 alkyl ester of 6-aminopenicillanic acid in a reaction-inert solvent, or a 6-aminopenicillanic acid amide in a reaction-inert solvent wherein the amide has the formula: <FORM:0958824/C2/4> at a temperature of from -25 DEG C. to 50 DEG C. and recovering the product therefrom. The Specification describes the production of many penicillins of the above formula such as DL-a -amino-benzylpenicillin, D- and L-a -amino-benzyl-penicillins, the t-butyl ester of aminomethyl penicillin and penicillin amides and of salts formed by neutralizing the appropriate penicillin acid.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12746861A | 1961-07-28 | 1961-07-28 | |
US15435261A | 1961-11-22 | 1961-11-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB958824A true GB958824A (en) | 1964-05-27 |
Family
ID=26825646
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2892362A Expired GB958824A (en) | 1961-07-28 | 1962-07-27 | Improvements in or relating to the production of penicillins |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB958824A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2100904A1 (en) * | 1970-07-14 | 1972-03-24 | Sarath | |
DE2302184A1 (en) * | 1972-01-20 | 1973-07-26 | Beecham Group Ltd | NEW PENICILLINS, THE PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PREPARATIONS CONTAINING THESE COMPOUNDS |
FR2197571A1 (en) * | 1972-09-01 | 1974-03-29 | Aries Robert | Bacterial penicillanic acid amides - prepd. from the acid and a para amino benzoic acid deriv resistant to penicillinase |
US6232305B1 (en) * | 1997-01-23 | 2001-05-15 | Naeja Pharmaceutical Inc. | Substituted amino bicyclic-β-lactam penam and cepham derivatives as cysteine protease inhibitors |
-
1962
- 1962-07-27 GB GB2892362A patent/GB958824A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2100904A1 (en) * | 1970-07-14 | 1972-03-24 | Sarath | |
DE2302184A1 (en) * | 1972-01-20 | 1973-07-26 | Beecham Group Ltd | NEW PENICILLINS, THE PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PREPARATIONS CONTAINING THESE COMPOUNDS |
FR2197571A1 (en) * | 1972-09-01 | 1974-03-29 | Aries Robert | Bacterial penicillanic acid amides - prepd. from the acid and a para amino benzoic acid deriv resistant to penicillinase |
US6232305B1 (en) * | 1997-01-23 | 2001-05-15 | Naeja Pharmaceutical Inc. | Substituted amino bicyclic-β-lactam penam and cepham derivatives as cysteine protease inhibitors |
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