US 11,866,438 B2
Compositions, uses and methods for making them
Mustapha Haddach, San Diego, CA (US)
Assigned to PIMERA, INC., San Diego, CA (US)
Filed by Pimera, Inc., San Diego, CA (US)
Filed on Mar. 17, 2021, as Appl. No. 17/204,459.
Application 17/204,459 is a division of application No. 15/555,024, granted, now 10,975,076, previously published as PCT/US2016/020418, filed on Mar. 2, 2016.
Claims priority of provisional application 62/128,208, filed on Mar. 4, 2015.
Prior Publication US 2021/0317120 A1, Oct. 14, 2021
Int. Cl. A61K 31/4353 (2006.01); C07D 471/14 (2006.01); C07D 487/14 (2006.01); C07D 471/04 (2006.01); A61P 35/00 (2006.01); C07D 471/22 (2006.01)
CPC C07D 471/14 (2013.01) [A61K 31/4353 (2013.01); A61P 35/00 (2018.01); C07D 471/04 (2013.01); C07D 471/22 (2013.01); C07D 487/14 (2013.01)] 9 Claims
 
1. A method for treating cancer in a subject in need thereof, wherein the cancer is leukemia or breast cancer, comprising administering to the subject a compound of having the structure of Formula III(A)(1), III(B)(1), or III(C)(1), or a pharmaceutically acceptable salt, hydrate, or tautomer thereof:

OG Complex Work Unit Chemistry
wherein:
L is a bond, C1-C10 alkylene, C1-C10 heteroalkylene, C2-C10 alkenylene, or C2-C10 heteroalkenylene linker, each of which may be optionally substituted with one or more substituents selected from the group consisting of halogen, oxo (═O), and C1-C6 alkyl;
A is heterocycloalkyl, heteroaryl, or NR4R5,
R4 and R5 are independently H, optionally substituted C1-C8 alkyl, C2-C8 heteroalkyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C1-C8 acyl, C2-C8 heteroacyl, C6-C10 aryl, C5-C12 heteroaryl, C7-C12 arylalkyl, or C6-C12 heteroarylalkyl group; or R4 and R5 can be linked to form a 3-8 membered ring, optionally containing one or more N, O or S; and each R4 and R5 groups, and each ring formed by linking R4 and R5 groups together, is optionally substituted with one or more substituents selected from halo, ═O, ═N—CN, ═N—OR′, ═NR′, OR′, N(R′)2, SR′, SO2R′, SO2NR′2, NR′SO2R′, NR′CONR′2, NR′ COOR′, NR′COR′, CN, COOR′, CON(R′)2, OOCR′, COR′, and NO2,
wherein each R′ is independently H, C1-C6 alkyl, C2-C6 heteroalkyl, C1-C6 acyl, C2-C6 heteroacyl, C6-C10 aryl, C5-C10 heteroaryl, C7-C12 arylalkyl, or C6-C12 heteroarylalkyl, each of which is optionally substituted with one or more groups selected from halo, C1-C4 alkyl, C1-C4 heteroalkyl, C1-C6 acyl, C1-C6 heteroacyl, hydroxy, amino, and ═O; wherein two R′ can be linked to form a 3-7 membered ring optionally containing up to three heteroatoms selected from N, O and S;
X is NR6, O, or S;
R6 is H, optionally substituted C1-C8 alkyl, C2-C8 heteroalkyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C1-C8 acyl, C2-C8 heteroacyl, C6-C10 aryl, C5-C12 heteroaryl, C7-C12 arylalkyl, or C6-C12 heteroarylalkyl group; or
R6 can be linked to R4 or R5 to form a 3-8 membered ring;
or A-L-X— is:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
X2 is hydrogen, or an optionally substituted C1-C8 alkyl, C2-C8 heteroalkyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C1-C8 acyl, C2-C8 heteroacyl, C6-C10 aryl, C5-C12 heteroaryl, C7-C12 arylalkyl, or C6-C12 heteroarylalkyl; or
X2 is H, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, or C2-C10 heteroalkenyl, each of which is optionally substituted with one or more halogens, ═O, or an optionally substituted 3-7 membered carbocyclic or heterocyclic ring; and
(U)n and (U)m are each independently H, halogen, CF3, CN, OR7, NR8R9, SR7, SO2NR8R9, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, or C2-C10 heteroalkenyl, each of which may be optionally substituted with one or more halogens, ═O, or an optionally substituted 3-7 membered carbocyclic or heterocyclic ring;
wherein each R7, R8 and R9 is independently selected from H, C1-C6 alkyl, C2-C6 heteroalkyl, C1-C6 acyl, C2-C6 heteroacyl, C6-C10 aryl, C5-C10 heteroaryl, C7-C12 arylalkyl, or C6-C12 heteroarylalkyl; and
wherein the term “optionally substituted” means that the referenced group, if no optional substituents are specifically described for the referenced group, is substituted with a substituent selected from halogen, —CN, —NH2, —OH, —NH(CH3), —N(CH3)2, —CH3, —CH2CH3, —CF3, —OCH3, and —OCF3.