This invention relates to a process for the preparation of antibacterial aminoglycoside derivatives and with intermediates for use in said process. More particularly it is concerned with a novel process for the preparation of 1-N-[.omega.-amino-2-hydroxyalkyl] and 1-N-[.omega.-(N-benzylamino-)-2-hydroxyalkyl] derivatives of aminoglycoside antibiotics. Said 1-N-[.omega.-amino-2-hydroxyalkyl] derivatives are known antibacterial agents, described in West Germany Offenlegungsschrift 2,547,738 and Belgian Pat. No. 818,431, and said 1-N-[.omega.-(N-benzylamino)-2-hydroxyalkyl] derivatives are useful as intermediates to said 1-N-[.omega.-amino-2-hydroxyalkyl] compounds. Additionally, this invention is concerned with certain cyclic urethane compounds which are also useful as intermediates in the process of the invention.
Previous procedures for the introduction of an .omega.-amino-2-hydroxyalkyl group onto the 1-amino group of an aminoglycoside antibiotic have required a multistage process. For example, in one process described in West German Offenlegungsschrift 2,547,738, the group is introduced by acylation with an .omega.-amino-2-hydroxy-carboxylic acid derivative having a protected amino group. The amino-protecting group is then removed and the amide bond is reduced to give the desired product. Other methods are described in Belgian Pat. No. 818431.
It is an object of this present invention to provide a convenient process for the introduction of an .omega.-amino-2-hydroxyalkyl substituent onto the 1-amino group of aminoglycoside antibiotics, which has the additional advantage of allowing the stereochemistry of the substituent to be readily controlled.