Aminoglycosides as antibiotics
The present invention provides aminoglycosides and pharmaceutical compositions that include the aminoglycosides. The aminoglycosides are useful to treat or prevent infectious diseases (e.g., bacterial infections) in a mammal (e.g., human).
1. A method of preparing a compound of formula I:
comprising contacting a compound of formula II:
wherein
R 1 is —NH 2 and R 2 is —NHP; or
R 1 is —NH(CO)—CH(OH)—(CH 2 ) 2 —NH 2 ; and R 2 is —NH(CO)—CH(OH)—(CH 2 ) 2 —NHP;
P is a protecting group; and
n is 2, 3, or 4;
with a catalytic transfer hydrogenation composition, to provide the compound of formula I.
2. The method of claim 1 , wherein P is a benzyloxycarbonyl group.
3. The method of claim 1 , wherein the catalytic transfer hydrogenation composition comprises a diene in the presence of a metal, in a solvent.
4. The method of claim 3 , wherein the metal is palladium.
5. The method of claim 4 , wherein the palladium is adsorbed on activated carbon.
6. The method of claim 3 , wherein the solvent comprises glacial acetic acid and the diene is 1,4-cyclohexadiene.
7. A method of preparing a compound of formula I:
comprising contacting a compound of formula (II):
wherein P is a protecting group; with a catalytic transfer hydrogenation composition, to provide the compound of formula I.
8. The method of claim 7 , wherein P is a benzyloxycarbonyl group.
9. The method of claim 7 , wherein the catalytic transfer hydrogenation composition comprises a diene in the presence of a metal, in a solvent.
10. The method of claim 9 , wherein the metal is palladium.
11. The method of claim 10 , wherein the palladium is absorbed on activated carbon.
12. The method of claim 9 wherein the solvent comprises glacial acetic acid and the diene is 1,4-cyclohexadiene.
13. A method of preparing a compound of formula (I):
comprising contacting a compound of formula (II):
wherein P is a protecting group; with a catalytic transfer hydrogenation composition, to provide the compound of formula (I).
14. The method of claim 13 , wherein P is a benzyloxycarbonyl group.
15. The method of claim 13 , wherein the catalytic transfer hydrogenation composition comprises a diene in the presence of a metal, in a solvent.
16. The method of claim 15 , wherein the metal is palladium.
17. The method of claim 16 , wherein the palladium is adsorbed on activated carbon.
18. The method of claim 15 , wherein the solvent comprises glacial acetic acid and the diene is 1,4-cyclohexadiene.
19. The method of claim 13 , wherein the —NH 2 substituent on the phenylethanoate group is in the para position.
20. The method of claim 13 , wherein the —NH 2 substituent on the phenylethanoate group is in the meta position.