US 12,122,769 B2
Synthesis of antibacterial aminoglycoside analogs
Raissa Trend, Warren, NJ (US); Michael Dappen, Warren, NJ (US); Christopher E. Henry, Warren, NJ (US); Adam Aaron Goldblum, Warren, NJ (US); James Bradley Aggen, Warren, NJ (US); Ricardo Filipe De Jesus Gonçalves Mendonça, Warren, NJ (US); and João Carlos Falcão Sardinha, Warren, NJ (US)
Assigned to CIPLA USA, INC., Warren, NJ (US)
Filed by Cipla USA, Inc., Warren, NJ (US)
Filed on Aug. 4, 2022, as Appl. No. 17/881,462.
Application 17/881,462 is a continuation of application No. 16/850,771, filed on Apr. 16, 2020, granted, now 11,453,658.
Application 16/850,771 is a continuation of application No. PCT/US2018/056536, filed on Oct. 18, 2018.
Claims priority of provisional application 62/574,544, filed on Oct. 19, 2017.
Prior Publication US 2023/0074115 A1, Mar. 9, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 407/12 (2006.01)
CPC C07D 407/12 (2013.01) [C07B 2200/13 (2013.01)] 17 Claims
 
1. A process for preparing a compound of formula (2), or a salt thereof, or solvate thereof, or an enantiomer thereof, or a diastereomer thereof comprising:
(a) contacting a compound of formula (1):

OG Complex Work Unit Chemistry
or an enantiomer thereof, or a diastereomer thereof, with 1-{[(p-nitrobenzyl)oxy]carbonyl}-1H-benzotriazole (PNZ-Bt) to form the compound of formula (2):

OG Complex Work Unit Chemistry
or a salt thereof, or a solvate thereof, or an enantiomer thereof, or a diastereomer thereof;
wherein - - - is a single bond or a double bond;
R1 is H or C1-C3 alkyl;
R2 is H or C1-C3 alkyl; and
R3 is H or C1-C3 alkyl.