4"-O-sulfonyl erythromycin-9-O-oxime derivatives

#This invention relates to antibiotic derivatives of erythromycin A and B, and more particularly to 4"-O-sulfonyl erythromycin A and B 9-O-oxime derivatives. The novel compounds of this invention have the following structural formula: ##STR2## where R is selected from the group consisting of oxygen, oxime, and substituted oxime, R.sub.1 is hydrogen or hydroxy and R.sub.2 is selected from the group consisting of phthalimide, substituted amides, benzamides, substituted benzamides, sulfonamides, substituted sulfonamides, amines, substituted amines, phenylurea, substituted phenylurea, phenylthiourea, substituted phenylthiourea, thiophenol and substituted thiophenol, phenoxides and substituted phenoxides and R.sub.3 is hydrogen or methyl. The present sulfonyl derivatives of erythromycin A, B and C are useful as antibiotics.

#Erythromycin is produced in three forms denoted A, B and C by cultivating a strain of Streptomyces erythreus in a suitable nutrient medium as is taught in U.S. Pat. No. 2,653,899, Bunch, et al. The structure of erythromycin is represented by the following formula: ##STR3##

#In this formula, when R.sub.3 is methyl and R.sub.1 is hydroxyl, the structure illustrated is erythromycin A. When R.sub.3 is methyl and R.sub.1 is hydrogen, the structure of erythromycin B is illustrated. When R.sub.3 is hydrogen and R.sub.1 is hydroxyl, the structure of erythromycin C is illustrated. The term "erythromycin" when used herein without modification is meant to embrace all three forms, that is, erythromycin A, B and C.

#The following examples more clearly illustrate the invention.

#To a cooling solution of 32.3 g. (0.045 M.) of Erythromycin B in 400 ml of pyridine, 23.8 g. (0.092 M.) of .beta.-Phthalimidoethane-sulfonyl chloride was added in one portion. After the addition, the reaction was allowed to stir in the ice bath for two hours. After this period of time, the reaction was poured into 3 liters of 5% NaHCO.sub.3 solution and extracted three times with 300 ml portions of chloroform. The extracts were combined, dried of MgSO.sub.4, filtered and concentrated to leave 43.4 grams of product. This material was recrystallized from Ethyl Acetate to obtain 27.8 grams of pure material. M.P. = 135.degree.-138.degree..

#Analysis: Theory: C:59.10; H:7.81; N:2.93; Found: C:58.51; H:7.82; N:2.97