US 12,128,028 B2
Heterocyclic sulfonamide derivatives and pharmaceutical uses thereof
Marc Rogers, Great Abingdon (GB); Robert Kirby, Great Abingdon (GB); Gakujun Shomi, Great Abingdon (GB); Takuya Matsuo, Great Abingdon (GB); Satoru Kobayashi, Great Abingdon (GB); Junichiro Kanazawa, Great Abingdon (GB); Nobutaka Yamaoka, Great Abingdon (GB); Makoto Torizuka, Great Abingdon (GB); and Koichi Suzawa, Great Abingdon (GB)
Assigned to METRION BIOSCIENCES LIMITED, Great Abingdon (GB)
Appl. No. 17/258,273
Filed by METRION BIOSCIENCES LIMITED, Great Abingdon (GB)
PCT Filed Jul. 5, 2019, PCT No. PCT/GB2019/051903
§ 371(c)(1), (2) Date Jan. 6, 2021,
PCT Pub. No. WO2020/008206, PCT Pub. Date Jan. 9, 2020.
Claims priority of application No. 1811165 (GB), filed on Jul. 6, 2018.
Prior Publication US 2021/0275499 A1, Sep. 9, 2021
Int. Cl. A61K 31/4164 (2006.01); A61K 31/4178 (2006.01); A61K 31/439 (2006.01); A61K 31/4439 (2006.01); A61K 31/454 (2006.01); A61K 31/46 (2006.01); A61K 31/5377 (2006.01); A61K 31/55 (2006.01); C07D 233/28 (2006.01); C07D 235/02 (2006.01); C07D 401/06 (2006.01); C07D 401/12 (2006.01); C07D 403/06 (2006.01); C07D 403/12 (2006.01); C07D 405/12 (2006.01); C07D 409/12 (2006.01); C07D 471/08 (2006.01); C07D 491/107 (2006.01)
CPC A61K 31/4164 (2013.01) [A61K 31/4178 (2013.01); A61K 31/439 (2013.01); A61K 31/4439 (2013.01); A61K 31/454 (2013.01); A61K 31/46 (2013.01); A61K 31/5377 (2013.01); A61K 31/55 (2013.01); C07D 233/28 (2013.01); C07D 235/02 (2013.01); C07D 401/06 (2013.01); C07D 401/12 (2013.01); C07D 403/06 (2013.01); C07D 403/12 (2013.01); C07D 405/12 (2013.01); C07D 409/12 (2013.01); C07D 471/08 (2013.01); C07D 491/107 (2013.01)] 23 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt or a solvate thereof, wherein:
R1 represents C1-6 alkyl, C1-6 alkoxy, C1-6 alkanol, —X—C3-8 cycloalkyl, haloC1-6 alkyl, aryl, heterocyclyl or heteroaryl, wherein said cycloalkyl, aryl, heterocyclyl or heteroaryl groups may be optionally substituted by one or more Ra groups;
Ra represents C1-6 alkyl, halogen, haloC1-6 alkyl, hydroxy, cyano, nitro, oxo, CONRxRy or C3-8 cycloalkyl;
Rx and Ry independently represent hydrogen or C1-6 alkyl;
X represents a bond, —CH2— or —(CH2)2—;
R2 represents halogen, haloC1-6 alkyl or cyano;
n represents an integer selected from 0 to 4;
R3 represents hydrogen, C1-6 alkyl, —X—C3-8 cycloalkyl, haloC1-6 alkyl or —X-aryl,
wherein said alkyl may be optionally substituted by one or more cycloalkyl groups,
wherein said cycloalkyl may be optionally substituted by one or more C1-6 alkyl, C1-6 alkoxy, haloC1-6 alkyl, halogen, hydroxy or cyano groups,
wherein said haloalkyl may be optionally substituted by one or more hydroxy groups,
wherein said aryl may be optionally substituted by one or more halogen groups,
wherein R3 and R4 together with the nitrogen atom to which they are attached may join to form a heterocyclyl ring optionally substituted by one or more C1-6 alkyl, haloC1-6 alkyl, or halogen;
R4 represents hydrogen, C1-6 alkyl or C3-8 cycloalkyl;
R5 represents C1-6 alkyl or —X-aryl; and
m represents an integer selected from 0 to 4, such that when m represents 2, said R5 groups may join to form a C3-8 cycloalkyl group.