1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols, methods for their manufacture, methods for their use as antibacterial agents, and compositions useful therefor
US4002742A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jul 30, 1974 |
| Grant date | Jan 11, 1977 |
| Priority date | — |
| Expiry date | Jul 30, 1994 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H15/236
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
1-N-Alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols, valuable as antibacterial agents, are prepared by treating an acid addition salt of a 4,6-di-(aminoglycosyl)-1,3-diamonocyclitol antibacterial agent in an inert solvent, preferably a protic solvent containing water, with one equivalent of a hydride donor reducing agent and with at least one equivalent of an aldehyde. The 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols are also prepared by treating the corresponding 1-N-acyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitol with an amide-reducing hydride reagent in an inert organic solvent. Other methods of preparing 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols include carrying out the foregoing processes with partially N-protected intermediates. Another useful process involves preparing a Schiff base of the 1-amino function of a partially N-protected 4,6-di-(aminoglycosyl)-1,3-diaminocyclitol followed by reduction of said Schiff base and removal of the N-protecting groups. Pharmaceutical compositions comprising 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols are described as well as the method of using said compositions to elicit an antibacterial response in a war…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.