摘要:
Penicillin sulfoxide acid is obtained in higher, more economical yield and of surprisingly good purity from penicillin in fermentation filtered broth by concentrating the broth, diluting the concentrated broth with miscible organic liquid, optionally separating insolubles, treating the liquid mixture with a peracid oxidizing agent to form sulfoxide, adjusting the ph of the mixture to 1.5 to 2.5, and crystallizing the penicillin sulfoxide acid, with the aid of additional water, if necessary, and separating the solid penicillin sulfoxide.
WHEREIN A IS HYDROGEN, ALKYL HAVING 1 TO 4 CARBON ATOMS, ARALKYL SELECTED FROM THE GROUP WHICH CONSISTS OF BENZYL AND PHENYLETHYL UNSUBSTITUTED OR SUBSTITUTED WITH CHLORO, METHOXY OR ETHOXY, OR ARYL SELECTED FROM THE GROUP WICH CONSISTS OF PHENYL AND NAPHTHYL UNSUBSTITUED OR SUBSTITUTED WITH CHLORINE, METHOXY OR ETHOXY; B IS HYDROGEN OR ALKYL HAVING 1 TO 4 CARBON ATOMS, Y IS OXYGEN OR SULFUR, X IS HYDROGEN OR ALKYL HAVING 1 TO 4 CARBON ATOMS, WHICH COMPRISES REACTING 6-AMINOPENICILLANIC ACID OR A TRIALKYLXYLYL ESTER THEREOF WITH A CARBOXYLIC ACID OF THE FORMULA II
3-(HOOC-C(-B)(-X)-Y-),4-A-1,2,5-THIADIAZOLE
OR A REACTIVE DERIVATIVE THEREOF SELECTED THE GROUP WHICH CONSISTS OF THE AZIDES, ACID CHLORIDES, ACID BROMIDES AND HYDRIDES OF SAID CARBOXYLIC ACID.
摘要:
6-(N - (SUBSTITUTED - IMIDOYL) AMINOACETAMIDO)PENICILLANIC ACIDS AND THEIR SALTS ARE VALUABLE AS ANTIBACTERIAL AGENTS, NUTRITIONAL SUPPLEMENTS IN ANIMAL FEEDS, THERAPEUTIC AGENTS IN POULTRY AND ANIMALS, INCLUDING MAN, AND ARE ESPECIALLY USEFUL IN THE TREATMENT OF INFECTIOUS DISEASES CAUSED BY GRAM-POSITIVE AND CERTAIN GRAM-NEGATIVE BACTERIA, MOST PARTICULARLY THOSE CAUSED BY THE PROTEUS GENUS. 6-(N-PHENYLACETIMIDOYL) - AMINOACETAMIDO)PENICILLANIC ACID, A PREFERRED EMBODIMENT OF THE INVENTION, IS PREPARED BY RANEY NICKEL HYDROGENATION (50 P.S.I., R.T.) OF AQUEOUS SOLUTION OF SODIUM 6-(3-BENZYL-1,2,4-OXADIAZOLE-5ONE-4-ACETAMIDO)PENICILLANATE WHICH IS PREPARED IN TURN BY REACTION OF 6-AMINOPENICILLANIC ACID WITH 3-BENZYL-1,2, 4-OXADIAZOLE-5-ONE-4-ACETYL CHLORIDE.
摘要:
6-Aminopenicillanic acid, 3-acetoxymethyl-7-amino- Delta 3cephem-4-carboxylic acid and 3-methyl-7-amino- Delta 3-cephem-4car-boxylic acid and esters thereof are reacted with ketene in an aqueous or inert non-aqueous solvent at a temperature between about 5* and about 35* C. to provide the corresponding acetamido derivatives in superior yields. 6-Acetamidopenicillanic acid, 3acetoxymethyl-7-acetamido- Delta 3-cephem-4-carboxylic acid, 3methyl-7-acetamido- Delta 3-cephem-4-carboxylic acid and the esters thereof are useful intermediates for the preparation of cephalosporin antibiotics.