US 11,952,383 B1
Aza-podophyllotoxin analogues as potential anti-cancer agents
Christophe Tratrat, Al-Ahsa (SA); and Michelyne Haroun, Al-Ahsa (SA)
Assigned to KING FAISAL UNIVERSITY, Al-Ahsa (SA)
Filed by KING FAISAL UNIVERSITY, Al-Ahsa (SA)
Filed on Jun. 30, 2023, as Appl. No. 18/216,994.
Application 18/216,994 is a division of application No. 18/122,047, filed on Mar. 15, 2023, granted, now 11,820,779.
Int. Cl. C07D 491/147 (2006.01); A61P 35/00 (2006.01); C07D 487/14 (2006.01); C07D 495/14 (2006.01)
CPC C07D 491/147 (2013.01) [A61P 35/00 (2018.01); C07D 487/14 (2013.01); C07D 495/14 (2013.01)] 12 Claims
 
1. A process for synthesizing a compound having the formula I:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof, wherein

OG Complex Work Unit Chemistry
represents a double bond,
n is 1;
W represents oxygen (O);
X represents an oxygen;
R1 represents:
a hydrogen atom;
R2, R3, R4, and R5, which may be the same or different, each represent:
a hydrogen atom;
and
R6 is an aryl or a heteroaryl optionally substituted in one or more positions with one or more of —OCH3, —OH, CH3, —NCH3, —NH2, —NHCOCH3, —F, —Cl, and —Br, the process comprising the following general reaction scheme:

OG Complex Work Unit Chemistry
wherein Ar is an aryl or a heteroaryl optionally substituted in one or more positions with one or more of —OCH3, —OH, CH3, —NCH3, —NH2, —NHCOCH3, —F, —Cl, and —Br; and
wherein 2-aminobenzimidazole and tetronic acid are reacted with aldehydes.