Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1995-11-20
1997-12-09
Peselev, Elli
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 136, 536 137, 536 185, C07H 100
Patent
active
056962444
ABSTRACT:
1-N-ethylsisomicin represented by the following structural formula I and pharmaceutically acceptable salts thereof are useful antibacterial agents and can be prepared in high yields by a characteristic method comprising the steps of: chelating sisomicin with a chelating agent in a protic solvent; protecting the 3-,2'-and 6'-amino groups of the chelated sisomicin derivative with an acylating reagent; removing the chelating metal from the sisomicin derivative by use of ammonia water, to obtain a 3, 2', 6-N-trisubstituted sisomicin derivative; reacting the trisubstituted sisomicin derivative with an ethylating reagent in an aprotic organic solvent, to selectively ethylate the 1-amino group of the trisubstituted sisomicin derivative; and deprotecting the ethylated sisomicin derivative: ##STR1##
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Wright, "Synthesis of 1-N-Ethylsisomicin: A Broad-spectrum Semisynthetic Aminoglycoside Antibiotic," J.C.S. Chem. Comm., 206-208 (1976).
Tattanahalli et al., "The Synthesis of Netilmicin via Complexing of Vicinal and non-Vicinal Amino-Hydroxyl Group Pairs with Divalent transition-Metal Cations," Carbohydrate Research, 130:243-249 (1984).
Kim Ha Young
Kim Joong-Hyup
Kim Sung Hoon
Nam Ghil Soo
Son Hyen Joo
Korea Institute of Science and Technology
Peselev Elli
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