US 12,344,599 B2
Prodigiosin analogs and methods of use
Wafik S. El-Deiry, Philadelphia, PA (US); and Xiaobing Tian, Philadelphia, PA (US)
Assigned to Institute for Cancer Research, Philadelphia, PA (US)
Filed by Institute For Cancer Research, Philadelphia, PA (US)
Filed on Apr. 16, 2024, as Appl. No. 18/636,634.
Application 18/636,634 is a continuation of application No. 18/076,778, filed on Dec. 7, 2022, granted, now 11,993,589.
Application 18/076,778 is a continuation of application No. 17/076,469, filed on Oct. 21, 2020, granted, now 11,535,608, issued on Dec. 27, 2022.
Application 17/076,469 is a continuation of application No. 16/396,669, filed on Apr. 27, 2019, granted, now 10,870,640, issued on Dec. 22, 2020.
Application 16/396,669 is a continuation in part of application No. 16/091,701, granted, now 10,654,801, issued on May 19, 2020, previously published as PCT/US2017/026748, filed on Apr. 10, 2017.
Claims priority of provisional application 62/778,978, filed on Dec. 13, 2018.
Claims priority of provisional application 62/319,882, filed on Apr. 8, 2016.
Prior Publication US 2024/0352005 A1, Oct. 24, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 403/14 (2006.01); A61P 35/00 (2006.01)
CPC C07D 403/14 (2013.01) [A61P 35/00 (2018.01)] 16 Claims
 
1. A method of treating cancer in a subject, the method comprising administering to the subject a compound of formula XIV:

OG Complex Work Unit Chemistry
wherein n is an integer from 0 to 5;
wherein R1 and R2 are, independently, selected from the group consisting of —H,—OH, halogen —C1—C6 alkyl,—C1—C6 fluoroalkyl,—CN,—NO2,—OR7,—SR7,—S(═O)R7,—S(═O)2R7, —NHS(═O)2R7,—C(═O)R7,—OC(═O)R7,—CO2R7,—OCO2R7,—CH(R7)2,—N(R7)2, —C(═O)N(R7)2,—NHC(═O)NHR7,—NHC(═O)R7,—NHC(═O)OR7,—C(OH)(R7)2, and —C(NH2)(R7)2;
wherein R3 is an optionally substituted aryl or an optionally substituted heteroaryl;
wherein R4, R5, and R6 are, independently,—OH,—C1-C10 alkyl,—O(C1-C10 alkyl), or —S(C1-C10 alkyl), wherein each alkyl group is, independently, optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halogen, —OH, —CN, and —NO2; and
wherein each R7 is, independently, —H, halogen, or C1-C6 alkyl, wherein the alkyl group is optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halogen, —OH, —CN, and —NO2,
or a tautomer or solvate thereof, or a pharmaceutically acceptable salt thereof.