US 12,215,092 B2
Pleiotropic pathway modifier compounds and method of treating diseases
Mingwen Wang, Berkeley Heights, NJ (US); and Linghua Zhang, Berkeley Heights, NJ (US)
Assigned to PPM BIOPHARMA LLC, Berkeley Heights, NJ (US)
Filed by PPM BIOPHARMA LLC, Berkeley Heights, NJ (US)
Filed on Feb. 26, 2024, as Appl. No. 18/586,920.
Claims priority of provisional application 63/486,836, filed on Feb. 24, 2023.
Prior Publication US 2024/0300918 A1, Sep. 12, 2024
Int. Cl. C07D 401/04 (2006.01); A61P 35/00 (2006.01)
CPC C07D 401/04 (2013.01) [A61P 35/00 (2018.01)] 26 Claims
OG exemplary drawing
 
1. A compound represented by Formula I,

OG Complex Work Unit Chemistry
wherein
X is CH2 or C═O,
R1 in each instance is independently selected from the group consisting of 3-6 membered cycloalkyl, 3-6 membered heterocycloalkyl, C1-4alkyl, OC1-4alkyl, NRaRb, halo C1-4alkyl, halogen, OH, CN, phenyl and 5- or 6-membered heteroaryl, wherein the phenyl and 5- or 6-membered heteroaryl are optionally substituted with one or more substituents selected from the group consisting of C1-4alkyl, OC1-4alkyl, NRaRb, halo C1-4alkyl, halogen, OH, and CN;
R2 is OH;
Ra and Rb in each instance is independently H or C1-4alkyl;
A is C1-3alkylene or void,
M is O, OC1-3alkylene, NRa, NHC(O)NH, O(CO)NH, NHC(O)O, or NHC(O), wherein O of OC1-3alkylene is bonded to A or the B ring when A is void;
L1 is NH, 3-6 membered heterocyclic, 6-membered aryl or 6-membered heteroaryl, haloC1-2alkylene, C1-3alkylene or void, wherein the aryl or heteroaryl is optionally substituted with one or more substituents selected from the group consisting of C1-4alkyl, ORa, SH, NRaRb, 3-6 membered cycloalkyl, COORa, CN, halogen, 3-6 membered cycloalkyl, OC1-4alkyl, and haloC1-4alkyl,
L2 in each instance is independently selected from the group consisting of 3-6 membered heterocylic, 6-membered aryl, 6-membered heteroaryl, —(CH2)aC(O)NRa—, —C(O)NRa—, —(CH2)aC(O)NRa(CH2)b—, —(CH2)a—, —(CH2)aO(CH2CH2O)c—, —(CH2)aS, —(CH2)aheterocyclyl-, —(CH2)aC(O)—, —(CH2)a NRa—, —CRa═N—NRa—, —CRa═N—O—, —CRa═N—NRb—CO—, —N═N—CO—, —S—S—, and any combination thereof, wherein a, b, and c are each an integer selected from 0 to 25, all subunits included;
L3 is C1-20alkylene, halo-C1-20alkylene, C2-20alkenlene, C2-20alkynlene or void;
m is 0, 1, 2 or 3;
n is an integer selected from 0 to 25, all subunits included;
or a pharmaceutically acceptable salt thereof,
provided that when A, L1 and (L2)n are void and M is NHC(O)NH, or NHC(O), M is not in an ortho position to X.