US 12,221,439 B2
Tetrahydropyridopyrimidine derivatives as AhR modulators
Antonio Mete, Leicestershire (GB); James Hitchin, Nottingham (GB); Mark Graham, Leicestershire (GB); John King-Underwood, Ledbury (GB); and Philip Vellacott Thorne, Nottingham (GB)
Assigned to JAGUAHR THERAPEUTICS PTE LTD, Singapore (SG)
Appl. No. 17/270,626
Filed by JAGUAHR THERAPEUTICS PTE LTD, Singapore (SG)
PCT Filed Aug. 23, 2019, PCT No. PCT/EP2019/072641
§ 371(c)(1), (2) Date Feb. 23, 2021,
PCT Pub. No. WO2020/039093, PCT Pub. Date Feb. 27, 2020.
Claims priority of application No. 10201807244X (SG), filed on Aug. 24, 2018.
Prior Publication US 2021/0332041 A1, Oct. 28, 2021
Int. Cl. C07D 471/04 (2006.01); C07D 487/04 (2006.01)
CPC C07D 471/04 (2013.01) [C07D 487/04 (2013.01)] 20 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
wherein:
Y is a 5 or 6 membered aromatic ring optionally containing 1, 2, or 3 heteroatoms selected from N, O and S, substituted with R5 and R6.;
R1 is H, C1-3 alkyl, (—CH2) pCN,—COC1-3 alkyl, —CO (CH2) qNR7R8,—SO2C1-3 alkyl, —SO2NR7R8, —(CH2)qPh, or —C(O)Z;
R2 is H or C1-3 alkyl;
R3 is H or C1-3 alkyl;
R4 is a 9 or 10 membered heteroaryl bearing substituents R9 and R10, wherein said heteroaryl haswith at least one heteroatom selected from N, O or S—;
R5 is H, hydroxy, halogen, CN, a C1-3 alkyl group, —CO(CH2) qNR7R8,-SO2C1-3 alkyl, or-SO2 NR7R8;
R6 is hydroxy, halogen, CN, a C1-3 alkyl group,-CO (CH2)qNR7R8, —SO2C1-3 alkyl, or-SO2 NR7R8.;
R7 is H or C1-3 alkyl;
R8 is H or C1-3 alkyl;
R9 is H, hydroxy, halogen, CN, a C1-3 alkyl group, —CO(CH2)q NR7R8, —SO2C1-3 alkyl, or —SO2 NR7R8,
R10 is H, hydroxy, halogen, CN, a C1-3 alkyl group, —CO(CH2)q NR7R8, —SO2C1-3 alkyl, or —SO2 NR7R8;
R11 is H or C1-3 alkyl;
X is NR11;
Z is a 5 or 6 membered heteroaryl with at least one heteroatom selected from N, O and S, optionally bearing one or two substituents selected from hydroxy, halogen, CN, or C1-3 alkyl;
b is an integer 1 or 2;
p is an integer 1, 2 or 3;
q is 0, 1, 2 or 3
wherein:
n is 2 and m is 1, or
n is 1 and m is 2,
or a pharmaceutically acceptable salt thereof.