2',3'-dideoxy-2'-fluorokanamycin A and 1-N-(.alpha.-hydroxy-.ome

Details 2',3'-dideoxy-2'-fluorokanamycin A and 1-N-(.alpha.-hydroxy-.ome 2',3'-dideoxy-2'-fluorokanamycin A and 1-N-(.alpha.-hydroxy-.ome

1985-12-10

1987-04-28

Brown, Johnnie R.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

536 137, 536 138, 536 179, 536 41, 536 187, 536122, 536 55, A61K 3171, C07H 15234

Patent

active

046614745

ABSTRACT:
New compounds, 2',3'-dideoxy-2'-fluorokanamycin A and 1-N-(.alpha.-hydroxy-.omega.-aminoalkanoyl) derivatives thereof, particularly 1-N-(DL- or L-3-amino-2-hydroxypropionyl)- and 1-N-(L-4-amino-2-hydroxybutyryl)-2',3'-dideoxy-2'-fluorokanamycins A are now provided, which are each useful as antibacterial agent. 2',3'-Dideoxy-2'-fluorokanamycin A is prepared by a process comprising condensing a 6-azido-4-O-protected-2,3,6-trideoxy-2-fluoro-.alpha.-D-ribo-hexopyranosyl bromide with the 4-hydroxyl group of a 6-O-(2',4',6'-tri-O-protected-3'-N-protected-3'-amino-3'-deoxy-.alpha.-D-g lucopyranosyl)-1,3-bis-N-protected-2-deoxystreptamine, reducing the resulting condensation product to convert its azido group into an amino group, and removing the remaining amino-protecting and hydroxyl-protecting groups from the reduction product.

REFERENCES:
patent: 4029883 (1977-06-01), Hiraga et al.
patent: 4104372 (1978-08-01), Umezawa et al.
patent: 4410516 (1983-10-01), Umezawa et al.
patent: 4424343 (1984-01-01), Cron et al.

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