US 12,466,819 B2
Tricyclic compounds with OMA1/OPA1 modulatory properties
Marcel Victor Alavi Khorassani Moghadam, Berkeley, CA (US)
Assigned to 712 North Inc., Oakland, CA (US)
Appl. No. 17/784,239
Filed by 712 North Inc., Oakland, CA (US)
PCT Filed Dec. 9, 2020, PCT No. PCT/US2020/064095
§ 371(c)(1), (2) Date Jun. 10, 2022,
PCT Pub. No. WO2021/119183, PCT Pub. Date Jun. 17, 2021.
Claims priority of provisional application 62/947,678, filed on Dec. 13, 2019.
Claims priority of provisional application 62/948,139, filed on Dec. 13, 2019.
Prior Publication US 2023/0065809 A1, Mar. 2, 2023
Int. Cl. C07D 409/12 (2006.01); C07D 265/34 (2006.01); C07D 267/16 (2006.01); C07D 279/20 (2006.01); C07D 405/12 (2006.01); C07D 407/06 (2006.01); C07D 409/04 (2006.01); C07D 409/14 (2006.01); C07D 413/04 (2006.01); C07D 413/12 (2006.01); C07D 471/10 (2006.01); C07D 471/22 (2006.01); C07D 487/04 (2006.01); C07D 498/04 (2006.01); C07D 513/04 (2006.01); C07F 7/08 (2006.01)
CPC C07D 409/12 (2013.01) [C07D 265/34 (2013.01); C07D 267/16 (2013.01); C07D 279/20 (2013.01); C07D 405/12 (2013.01); C07D 407/06 (2013.01); C07D 409/04 (2013.01); C07D 409/14 (2013.01); C07D 413/04 (2013.01); C07D 471/10 (2013.01); C07D 471/22 (2013.01); C07D 487/04 (2013.01); C07D 498/04 (2013.01); C07D 513/04 (2013.01); C07F 7/0807 (2013.01)] 14 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
or a stereochemical isomeric form thereof, wherein
A is an alkyl, alkylene, alkenyl, alkynyl, alkylidene, —N(H)—, —N(R11)—, —N(OH)—, —S(O)2—, —S(O)—, —O—, or the like;
B is C, N, O, P, or S provided that when B represents N or O then B may or may not be substituted at R6;
R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, or R12 is hydrogen, halo, hydroxy, carboxy, keto, alkyl, alkylene, haloalkyl, polyhaloalkyl, haloalkoxy, nitrile, carbocyclic residue, aryl, aryloxy, arylamino, arylalkylamino, arylthio, arylalkanoylamino, arylsulfonyl, arylalkoxy, arylsulfinyl, arylheteroaryl, arylalkylthio, arylcarbonyl, arylalkenyl, or arylalkylsulfonyl, alkynyl, alkenyl, alkyloxy, polyhaloalkyloxy, alkylidene, cycloalkyl, cycloalkanone, heterocyclic group, heteroaryl, —C(O)OR12, —NR13R14, —C(O)NR13R14 or the like, wherein NR13R14 may form a heterocyclic ring, or a chemical group;
and wherein at least one of R1, R2, R3, R4, R7, R8, R9, or R10 is a group of formula (II)

OG Complex Work Unit Chemistry
or a stereochemical isomeric form thereof, wherein
A′ is a sulfonyl group (—S(O)2—);
B′ is N, O, P or S; and
R′1 or R′2 is hydrogen, halo, hydroxy, carboxy, keto, alkyl, alkylene, haloalkyl, polyhaloalkyl, haloalkoxy, nitrile, carbocyclic residue, aryl, aryloxy, arylamino, arylalkylamino, arylthio, arylalkanoylamino, arylsulfonyl, arylalkoxy, arylsulfinyl, arylheteroaryl, arylalkylthio, arylcarbonyl, arylalkenyl, or arylalkylsulfonyl, alkynyl, alkenyl, alkyloxy, polyhaloalkyloxy, alkylidene, cycloalkyl, cycloalkanone, heterocyclic group, heteroaryl, —C(O)OR12, —NR13R14, —C(O)NR13R14 or the like, wherein NR13R14 may form a heterocyclic ring, or a chemical group;
or a pharmaceutically acceptable salt thereof, or an N-oxide thereof.