US 12,404,284 B2
Spirocyclic inhibitors of hepatitis B virus
Romano Di Fabio, Pomezia (IT); Vincenzo Summa, Pomezia (IT); Leda Ivanova Bencheva, Milan (IT); Raffaele De Francesco, Milan (IT); Lorena Donnici, Milan (IT); Luca Guidotti, Milan (IT); Matteo Iannacone, Milan (IT); Adolfo Prandi, Milan (IT); Marilenia De Matteo, Milan (IT); and Pietro Randazzo, Milan (IT)
Assigned to Ospedale San Raffaele S.r.l., Milan (IT); and Istituto Nazionale Genetica Molecolare—INGM, Milan (IT)
Appl. No. 17/798,784
Filed by Ospedale San Raffaele S.r.l., Milan (IT); and Istituto Nazionale Genetica Molecolare—INGM, Milan (IT)
PCT Filed Feb. 9, 2021, PCT No. PCT/EP2021/053099
§ 371(c)(1), (2) Date Aug. 10, 2022,
PCT Pub. No. WO2021/160617, PCT Pub. Date Aug. 19, 2021.
Claims priority of application No. 20156716 (EP), filed on Feb. 11, 2020; and application No. 20201798 (EP), filed on Oct. 14, 2020.
Prior Publication US 2023/0151027 A1, May 18, 2023
Int. Cl. C07D 515/14 (2006.01)
CPC C07D 515/14 (2013.01) 17 Claims
 
1. A compound of general formula (I):

OG Complex Work Unit Chemistry
wherein:
Cy is aryl or heteroaryl;
each of m and n is independently 1 or 2;
R1 is H, F, Br, Cl or CH3;
R2 is selected from the group consisting of:
5 or 6 membered heteroaryl ring optionally substituted with one or more substituents each independently selected from the group consisting of: OH, halogen, CN, C1-6alkyl, hydroxyC1-6alkyl, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxy and NH2;
haloC1-4alkyl; and
C(═O)NR3R4;
each of R3 and R4 is independently selected from the group consisting of:
hydrogen;
C1-3alkyl;
haloC1-4alkyl; and
C3-5-cycloalkyl optionally substituted with one or more substituents each independently selected from the group consisting of: methyl, F, Cl, CHF2 and CF3;
or R3 and R4 form together with the nitrogen atom to which they are attached a cyclic amine selected from the group consisting of: aziridine, azetidine, pyrrolidine, piperidine, morpholine and thiomorpholine each of said cyclic amine being optionally substituted with one or more substituents each independently selected from the group consisting of: methyl, fluorine, CHF2 and CF3;
Ra, Rb, Rc and Rd are each independently selected from the group consisting of: hydrogen, halogen, methyl, CN, CHF2 and CF3;
or a pharmaceutically acceptable salt, solvate or stereoisomer thereof.