US 11,945,798 B2
Substituted aminopyridine compounds as EGFR inhibitors
Hyunjoo Lee, Suwon-si (KR); Su Bin Choi, Hwaseong-si (KR); Young Ae Yoon, Seongnam-si (KR); Kwan Hoon Hyun, Incheon (KR); Jae Young Sim, Yongin-si (KR); Marian C. Bryan, Spring House, PA (US); Scott Kuduk, Spring House, PA (US); James Campbell Robertson, Spring House, PA (US); Jaekyoo Lee, North Andover, MA (US); Paresh Devidas Salgaonkar, Lexington, MA (US); Byung-Chul Suh, Lexington, MA (US); Jong Sung Koh, Cambridge, MA (US); and So Young Hwang, Lexington, MA (US)
Assigned to YUHAN CORPORATION, Seoul (KR); and JANSSEN BIOTECH, INC., Horsham, PA (US)
Filed by YUHAN CORPORATION, Seoul (KR); and JANSSEN BIOTECH, INC., Horsham, PA (US)
Filed on Aug. 26, 2022, as Appl. No. 17/822,438.
Claims priority of provisional application 63/237,653, filed on Aug. 27, 2021.
Prior Publication US 2023/0086795 A1, Mar. 23, 2023
Int. Cl. C07D 401/14 (2006.01); C07D 413/14 (2006.01)
CPC C07D 401/14 (2013.01) [C07D 413/14 (2013.01)] 39 Claims
 
1. A compound of formula (I) or a pharmaceutically acceptable salt thereof,

OG Complex Work Unit Chemistry
wherein
R1 is selected from the group consisting of
C1-6 alkyl optionally substituted by one or more substituents selected from the group consisting of OH, halogen, C3-6 cycloalkyl, —NHC1-6 alkyl, and N(C1-6 alkyl)2;
C1-3 alkoxy;
—C(O)—C1-6 alkyl, optionally substituted by one or more substituents selected from the group consisting of halogen, —NHC1-6 alkyl, —N(C1-6 alkyl)2, and 4-7 membered heterocyclyl;
—C(O)—C3-6 cycloalkyl, optionally substituted by one or more substituents selected from the group consisting of OH and halogen;
—C(O)—C6-10 aryl optionally substituted by one or more halogens;
—C(O)-5-6 membered heteroaryl optionally substituted by one or more halogens;
—N(C1-6 alkyl)2;
—NHC(O)C1-6 alkyl;
—NHC(O)C3-6 cycloalkyl, optionally substituted by one or more substituents selected from the group consisting of OH and halogen;
—C(O)NHC1-6 alkyl optionally substituted by one or more substituents selected from the group consisting of OH and halogen;
—C(O)NHC3-6 cycloalkyl optionally substituted by one or more substituents selected from the group consisting of OH, halogen and —N(C1-6 alkyl)2;
—C(O)-3-7 membered heterocyclyl optionally substituted by one or more substituents selected from the group consisting of OH, halogen, C1-6 alkyl, and C1-6 hydroxyalkyl; and
4-7 membered heterocyclyl optionally substituted by one or more substituents selected from the group consisting of OH and halogen,
R2 is selected from the group consisting of —XC1-6 alkyl optionally substituted by one or more substituents selected from the group consisting of OH, halogen, and —N(C1-6 alkyl)2; and —X(CH2)n-A-(R2A)o,
X is —NH—, —O—, bond or —C≡C—,
n is an integer of 0 to 2,
is an integer of 0 to 3,
A is selected from the group consisting of C3-8 cycloalkyl; C6-10 aryl; 4-11 membered heterocyclyl; and 5-6 membered heteroaryl,
R2A is independently selected from the group consisting of
H;
halogen;
OH;
NH2;
C1-6 alkyl optionally substituted by one or more substituents selected from the group consisting of OH, NH2, halogen, C3-6 cycloalkyl, C1-3 alkoxy, —NHC1-6 alkyl, —NHC1-6 hydroxyalkyl, —NHC1-6 haloalkyl, —NHC3-6 cycloalkyl, —N(C1-6 alkyl)2, —N(C1-6 haloalkyl)2, —NHC(O)C1-6 alkyl, —C(O)NHC1-6 alkyl, —C(O)N(C1-6 alkyl)2, 3-7 membered heterocyclyl and 5-6 membered heteroaryl;
C3-6 cycloalkyl;
C1-3 alkoxy optionally substituted by one or more halogens;
—C(O)NHC1-6 alkyl optionally substituted by one or more substituents selected from the group consisting of OH and halogen;
—C(O)N(C1-6 alkyl)2 optionally substituted by one or more substituents selected from the group consisting of OH and halogen;
—NHC1-6 alkyl optionally substituted by one or more substituents selected from the group consisting of OH, halogen, —NHC1-6 alkyl, —N(C1-6 alkyl)2, and 3-7 membered heterocyclyl optionally substituted by halogen or —N(C1-6 alkyl)2;
—N(C1-6 alkyl)2 where C1-6 alkyl is optionally substituted by one or more halogens;
—NH-4-7 membered heterocyclyl optionally substituted by C1-6 alkyl; and
4-7 membered heterocyclyl,
R3 is selected from the group consisting of
H;
C1-6 alkyl optionally substituted by one or more substituents selected from the group consisting of halogen and C3-6 cycloalkyl;
C3-6 cycloalkyl;
4-7 membered heterocyclyl;
—S(O)2C1-6 alkyl optionally substituted by one or more halogens; and
—S(O)2C3-6 cycloalkyl optionally substituted by one or more halogens, and
R4 is selected from the group consisting of H, halogen and C1-6 alkyl.