US 12,084,416 B2
Substituted sulfonylurea derivatives
Rajiv Sharma, Gujarat (IN); and Sameer Agarwal, Gujarat (IN)
Assigned to Zydus Lifesciences Limited, Gujarat (IN)
Appl. No. 17/422,500
Filed by Zydus Lifesciences Limited, Gujarat (IN)
PCT Filed Jan. 13, 2020, PCT No. PCT/IB2020/050216
§ 371(c)(1), (2) Date Jul. 13, 2021,
PCT Pub. No. WO2020/148619, PCT Pub. Date Jul. 23, 2020.
Claims priority of application No. 201921001555 (IN), filed on Jan. 14, 2019.
Prior Publication US 2022/0169605 A1, Jun. 2, 2022
Int. Cl. C07D 207/48 (2006.01); C07D 205/04 (2006.01); C07D 207/08 (2006.01); C07D 211/24 (2006.01); C07D 211/96 (2006.01); C07D 401/04 (2006.01); C07D 403/04 (2006.01); C07D 403/06 (2006.01); C07D 405/04 (2006.01); C07D 405/06 (2006.01); C07D 409/04 (2006.01); C07D 409/06 (2006.01); C07D 409/12 (2006.01); C07D 417/04 (2006.01); C07D 417/06 (2006.01)
CPC C07D 207/48 (2013.01) [C07D 205/04 (2013.01); C07D 207/08 (2013.01); C07D 211/24 (2013.01); C07D 211/96 (2013.01); C07D 401/04 (2013.01); C07D 403/04 (2013.01); C07D 403/06 (2013.01); C07D 405/04 (2013.01); C07D 405/06 (2013.01); C07D 409/04 (2013.01); C07D 409/06 (2013.01); C07D 409/12 (2013.01); C07D 417/04 (2013.01); C07D 417/06 (2013.01)] 13 Claims
 
1. A compound having the structure of general formula (I)

OG Complex Work Unit Chemistry
or a tautomeric form, a stereoisomer, an enantiomer, or a pharmaceutically acceptable salt, thereof,
wherein,
R1 at each occurrence is independently selected from hydrogen, halogen, haloalkyl, cyano, and optionally substituted groups selected from (C1-C6)alkyl, (C1-C6)haloalkyl, (C2-C6)alkenyl, (C1-C6)alkoxy, (C3-C7)cycloalkyl, NH2, NH(C1-C6)alkyl, N(C3-C7)cycloalkyl, N(C1-C6 alkyl)2, aryl, heteroaryl, heterocyclyl, benzyl, thiol, mercapto alkyl, SO2(C1-C6)alkyl, (C1-C6)thio-alkoxy, and amide;
X is N—R5, O, S, or SO2;
R5 at each occurrence is independently selected from hydrogen, halogen, haloalkyl, cyano, and optionally substituted groups selected from (C1-C6)alkyl, (C1-C6)haloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C3-C7)cycloalkyl, (C1-C6)alkylSO2(C1-C6)alkyl, (C1-C6)alkylN(C1-C6)alkyl, (C1-C6)alkylN(C3-C7)cycloalkyl, aryl, heteroaryl, heterocyclyl, benzyl, tert-butyloxycarbonyl, thiol, mercapto alkyl, SO2(C1-C6)alkyl, SO2(C3-C7)cycloalkyl, SO2-aryl, SO2-heterocyclyl, (C1-C6)thioalkyl, (C1-C6)thioalkoxy, (C1-C6)alkylSO2NH2, —CONH2, —CO(C1-C6)alkyl, —CO(C1-C6)haloalkyl, —CO-aryl, —CO-heteroaryl, —CO-heterocyclyl, 4- to 7-membered heterocyclic ring, 7- to 14-membered bicyclic heterocyclic ring system, and bridged or spiro ring system having optionally one or more than one heteroatoms;
m and n is independently selected from integer 0-3;
q and r is independently selected from integer 1-4;
R2 at each occurrence is independently selected from hydrogen, halogen, cyano, and optionally substituted groups selected from (C1-C6)alkyl, (C2-C6)alkenyl, (C1-C6)alkoxy, (C3-C7)cycloalkyl, benzyl, aryl, heteroaryl, heterocyclyl, thiol, thioalkyl, thio-alkoxy, SO2(C1-C6)alkyl, SO(C1-C6)alkyl, and bridged or spiro ring system having optionally one or more than one heteroatoms;
each of R3 and R4 at each occurrence is independently selected from hydrogen, halogen, haloalkyl, cyano, nitro, amide, sulphonamide, acyl, hydroxyl, and optionally substituted groups selected from (C1-C6)alkyl, (C1-C6)haloalkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, SO2(C1-C6)alkyl, thiol, mercapto alkyl, benzyl, aryl, heteroaryl, and heterocyclyl; alternatively R3 and R4 forms a bond;
‘B’ is selected from the following ring systems

OG Complex Work Unit Chemistry
wherein X, Y, Z at each occurrence are independently selected from C, N, S, SO2 and O, which may, wherever possible be optionally substituted;
each of R6, R7, R8, R9, R10 and R11 at each occurrence are independently selected from hydrogen, halogen, cyano, amide, sulphonamide, acyl, hydroxyl, and optionally substituted groups selected from (C1-C6)alkyl, (C1-C6)haloalkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, benzyl, aryl, heteroaryl, and heterocyclyl; alternatively each of R7 and R8, R8 and R9, R9 and R10 or R10 and R11 wherever possible, together may form a 4 to 7 membered saturated or partially saturated ring containing from 0-2 additional heteroatoms selected from the group consisting of N, O, and S(O)p; and
p is 1 or 2.