Aminoglycoside antibiotic derivatives and process for their prep

Details Aminoglycoside antibiotic derivatives and process for their prep Aminoglycoside antibiotic derivatives and process for their prep

1979-06-12

1981-01-27

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

424180, 536 10, 536 17R, C07H 1522

Patent

active

042476879

ABSTRACT:
A process is disclosed for preparing 4'-deoxy-neomycin B, having the formula: ##STR1## Chlorination with sulphuryl chloride in pyridine gives the corresponding 4'-6'-dichloro analog which is selectively dechlorinated at position 4' with tributyltin hydride. The 6'-chloro group is then subjected to azidolysis to introduce an azido group. De-O-benzoylation of the resulting 6'-azido derivative, followed by hydrogenolysis, gives 4'-deoxy neomycin B. The new compound displays an antibacterial activity with a higher grade and broader spectrum when compared with those of neomycin B and paromomycin I.

REFERENCES:
patent: 4024332 (1977-05-01), Fenner et al.
patent: 4065615 (1977-12-01), Horii et al.
patent: 4125707 (1978-11-01), Arcamone et al.

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