IP Library › Granted Patent US 12,440,484
Granted Patent B2
US 12,440,484 · App. 17/615,363 · Granted Oct 14, 2025

1,3,4-oxadiazole homophthalimide derivative compounds as histone deacetylase 6 inhibitor, and the pharmaceutical composition comprising the same

Inventors: Chang Sik Lee (Gyeonggi-do, KR); Jung Taek Oh (Gyeonggi-do, KR); Hokeun Yun (Gyeonggi-do, KR); Hyeseung Song (Gyeonggi-do, KR); Hyunjin Michael Kim (Gyeonggi-do, KR)
Assignee: Chong Kun Dang Pharmaceutical Corporation
A61K31/4439A61K31/4245A61K31/437A61K31/4725A61K31/496A61K31/506A61K31/517A61K31/5377
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,440,484
App. No.
17/615,363
Granted
Oct 14, 2025
Kind
B2
Abstract

The present invention relates to novel compounds having a histone deacetylase 6 (HDAC6) inhibitory activity, stereoisomers thereof or pharmaceutically acceptable salts thereof, a medicinal use thereof, and a method for preparing the same. The novel compounds according to the present invention, stereoisomers thereof or pharmaceutically acceptable salts thereof have the histone deacetylase 6 (HDAC6) inhibitory activity, and are effective in preventing or treating HDAC6-related diseases, comprising infectious diseases; neoplasm; endocrinopathy; nutritional and metabolic diseases; mental and behavioral disorders; neurological diseases; eye and ocular adnexal diseases; circulatory diseases; respiratory diseases; digestive diseases; skin and subcutaneous tissue diseases; musculoskeletal system and connective tissue diseases; and teratosis or deformities, or chromosomal aberration.

Claims (300)

1. A compound represented by a following chemical formula I, stereoisomers thereof or pharmaceutically acceptable salts thereof:

wherein,

X 1 to X 4 are each independently CR 0 or N, wherein at least two of X 1 to X 4 are CR 0 ,

in which each R 0 is independently hydrogen, halogen, straight or branched —C 1-7 alkyl, or straight or branched —O—C 1-7 alkyl,

R 1 is straight or branched —C 1-5 haloalkyl,

R 2 and R 3 are each independently H, halogen,

 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from group comprising N, O or S, 3- to 7-membered heterocycloalkenyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 —C 1-7 alkyl, 3- to 7-membered cycloalkyl, 3- to 7-membered cycloalkenyl, cyclopenta-1,3-diene, phenyl, indolyl,

wherein at least one hydrogen of said 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered heterocycloalkenyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 —C 1-7 alkyl, 3- to 7-membered cycloalkyl, 3- to 7-membered cycloalkenyl, cyclopenta-1,3-diene, phenyl, indolyl,

 can be substituted with R 4 ,

R 4 is halogen, —C 1-7 alkyl, —C 1-7 haloalkyl, —O—C 1-7 alkyl, —C(═O)—C 1-7 alkyl, —C(═O)—C 1-7 alkyl-OH, —C(═O)—O—C 1-7 alkyl, —S(═O) 2 —C 1-7 alkyl, 3- to 7-membered cycloalkyl, 3- to 7-membered halocycloalkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 —C 1-7 alkyl-C(═O)—R 5 , —C 1-7 alkyl-C(═O)—O—R 6 , —C 1-7 alkyl-R 7 , —C 1-7 alkyl-O—R 8 , —NR 9 R 10 , —C(═O)—NR 11 R 12 or —C 1-7 alkyl-NR 13 R 14 ,

in which R 5 is —C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, cyclopenta-1,3-diene or phenyl,

R 6 is —C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, cyclopenta-1,3-diene or phenyl,

R 7 is 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, cyclopenta-1,3-diene or phenyl,

R 8 is —C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, cyclopenta-1,3-diene or phenyl,

R 9 and R 10 are each independently H or —C 1-7 alkyl,

R 11 and R 12 are each independently H or —C 1-7 alkyl, and

R 13 and R 14 are each independently H or —C 1-7 alkyl,

R x and R y are each independently —C 1-7 alkyl, —C 1-7 alkyl-NR 15 R 16 , H, —C 1-7 alkyl-O-C 1-7 alkyl, —C(═O)—C 1-7 alkyl, heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)-heterocycloalkyl wherein the heterocycloalkyl is a 3-to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O) cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, —C 1-7 alkyl-O-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S or —C 1-7 alkyl-cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl wherein at least one hydrogen of —C 1-7 alkyl, —C 1-7 alkyl-O—C 1-7 alkyl, —C(═O)—C 1-7 alkyl, —C(═O)-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O) cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, —C 1-7 alkyl-O-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S or —C 1-7 alkyl-cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl can be substituted with —C 1-7 alkyl, halogen, —O—C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, —S(═O) 2 —C 1-7 alkyl, —CF 3 ,

 and

R 15 and R 16 are each independently H or —C 1-7 alkyl),

K is O or S,

Y is CR a R b or NR c ,

R a and R b are each independently hydrogen, —C 1-7 alkyl, 3- to 7-membered cycloalkyl, —C 1-7 alkyl-O—C 1-7 alkyl, —C 1-7 alkyl-NR 17 R 18 , 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-C(═O)—C 1-7 alkyl or —C 1-7 alkyl-C(═O)—O—C 1-7 alkyl, or R a and R b are linked to each other to form 3- to 7-membered cycloalkyl,

wherein at least one hydrogen of —C 1-7 alkyl, 3- to 7-membered cycloalkyl, —C 1-7 alkyl-O—C 1-7 alkyl, —C 1-7 alkyl-NR 17 R 18 , 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-C(═O)—C 1-7 alkyl or —C 1-7 alkyl-C(═O)—O—C 1-7 alkyl may be substituted with —C 1-7 alkyl, halogen, —O—C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, —S(═O) 2 —C 1-7 alkyl, —CF 3 ,

 and R 17 and R 18 are each independently H or —C 1-7 alkyl, R c is hydrogen, —C 1-7 alkyl, —C 1-7 alkyl-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-phenyl, —C 1-7 alkyl-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-O—C 1-7 alkyl, —C 1-7 alkyl-NR 19 R 20 , —C 1-7 alkyl-cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, a 3- to 7-membered cycloalkyl, a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, cyclopenta-1,3-diene, phenyl, —C(═O)—, —C(═O)-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O) cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, —C(═O)-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)-phenyl, —C(═O)—C 1-7 alkyl, —C(═O)—C 1-7 alkyl-O—C 1-7 alkyl or —C(═O)—C 1-7 alkyl-NR 19 R 20 , wherein at least one hydrogen of —C 1-7 alkyl, —C 1-7 alkyl-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-phenyl, —C 1-7 alkyl-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-O—C 1-7 alkyl, —C 1-7 alkyl-NR 19 R 20 , —C 1-7 alkyl-cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, a 3- to 7-membered cycloalkyl, a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, cyclopenta-1,3-diene, phenyl, —C(═O)—, —C(═O)-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O) cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, —C(═O)-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)-phenyl, —C(═O)—C 1-7 alkyl, —C(═O)—C 1-7 alkyl-O—C 1-7 alkyl or —C(═O)—C 1-7 alkyl-NR 19 R 20 , can be substituted with —C 1-7 alkyl, halogen, —O—C 1-7 alkyl, a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)—O—C 1-7 alkyl, a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, heteroaryl-C 1-5 haloalkyl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, —S(═O) 2 —C 1-7 alkyl, —CF 3 ,

 and R 19 and R 20 are each independently H or —C 1-7 alkyl,

 is phenylene or 5- or 6-membered heteroarylene comprising one to three heteroatoms selected from the group comprising N, O or S,

halogen is F, Cl, Br or I, and

n is 1.

2. The compound represented by the chemical formula I, stereoisomers thereof or pharmaceutically acceptable salts thereof according to claim 1 , wherein

X 1 to X 4 are each independently CR 0 or N, wherein at least two of X 1 to X 4 are CR 0 ,

in which R 0 is hydrogen, halogen or —O—C 1-7 alkyl,

R 1 is —C 1-5 haloalkyl,

R 2 and R 3 are each independently H, halogen,

 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from group comprising N, O or S, 3- to 7-membered heterocycloalkenyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 phenyl, indolyl,

 or —C 1-7 alkyl,

(in which at least one hydrogen of said 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered heterocycloalkenyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 phenyl, indolyl,

 or —C 1-7 alkyl can be substituted with R 4 ,

R 4 is halogen, —C 1-7 alkyl, —C 1-7 haloalkyl, —O—C 1-7 alkyl, —C(═O)—C 1-7 alkyl, —C(═O)—C 1-7 alkyl-OH, —C(═O)—O—C 1-7 alkyl, —S(═O) 2 —C 1-7 alkyl, 3- to 7-membered cycloalkyl, 3- to 7-membered halocycloalkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 —C 1-7 alkyl-C(═O)—R 5 , —C 1-7 alkyl-C(═O)—O—R 6 , —C 1-7 alkyl-R 7 , —C 1-7 alkyl-O—R 8 , —NR 9 R 10 , —C(═O)—NR 11 R 12 or —C 1-7 alkyl-NR 13 R 14 ,

in which R 5 is —C 1-7 alkyl or 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S,

R 6 is —C 1-7 alkyl,

R 7 is 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S or 3- to 7-membered cycloalkyl,

R 8 is —C 1-7 alkyl,

R 9 and R 10 are each independently H or —C 1-7 alkyl,

R 11 and R 12 are each independently H or —C 1-7 alkyl, and

R 13 and R 14 are each independently H or —C 1-7 alkyl),

R x and R y are each independently —C 1-7 alkyl, —C 1-7 alkyl-NR 15 R 16 , H, —C 1-7 alkyl-O—C 1-7 alkyl, —C(═O)—C 1-7 alkyl, —C(═O)-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)-heterocycloalkyl wherein the heterocycloalkyl is a 3-to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S) or —C(═O) cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl wherein at least one hydrogen of —C 1-7 alkyl, —C 1-7 alkyl-O—C 1-7 alkyl, —C(═O)—C 1-7 alkyl, —C(═O)-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S or —C(═O)-cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl can be substituted with-C 1-7 alkyl, halogen, —O—C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, a 3- to 7-membered cycloalkyl, —S(═O) 2 —C 1-7 alkyl, —CF 3 ,

 and R 15 and R 16 are each independently H or —C 1-7 alkyl,

K is O or S,

Y is CR a R b or NR c ,

R a and R b are each independently hydrogen, —C 1-7 alkyl, 3- to 7-membered cycloalkyl, —C 1-7 alkyl-O—C 1-7 alkyl, —C 1-7 alkyl-NR 17 R 18 , or R a and R b are linked to each other to form 3- to 7-membered cycloalkyl,

wherein at least one hydrogen of —C 1-7 alkyl, 3- to 7-membered cycloalkyl, —C 1-7 alkyl-O—C 1-7 alkyl or —C 1-7 alkyl-NR 17 R 18 can be substituted with —C 1-7 alkyl, halogen, —O—C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, —S(═O) 2 —C 1-7 alkyl, —CF 3 ,

 and R 17 and R 18 are each independently H or —C 1-7 alkyl, R c is hydrogen, —C 1-7 alkyl, —C 1-7 alkyl-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-phenyl, —C 1-7 alkyl-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-O—C 1-7 alkyl, —C 1-7 alkyl-NR 19 R 20 , —C 1-7 alkyl-cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, a 3- to 7-membered cycloalkyl, a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, cyclopenta-1,3-diene, phenyl, —C(═O)—, —C(═O)-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O) cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, —C(═O)-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)-phenyl, —C(═O)—C 1-7 alkyl, —C(═O)—C 1-7 alkyl-O—C 1-7 alkyl or —C(═O)—C 1-7 alkyl-NR 19 R 20 , wherein at least one hydrogen of —C 1-7 alkyl, —C 1-7 alkyl-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-phenyl, —C 1-7 alkyl-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-O—C 1-7 alkyl, —C 1-7 alkyl-NR 19 R 20 , —C 1-7 alkyl-cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, a 3- to 7-membered cycloalkyl, a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, cyclopenta-1,3-diene, phenyl, —C(═O)—, —C(═O)-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O) cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, —C(═O)-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)-phenyl, —C(═O)—C 1-7 alkyl, —C(═O)—C 1-7 alkyl-O—C 1-7 alkyl or —C(═O)—C 1-7 alkyl-NR 19 R 20 , can be substituted with —C 1-7 alkyl, halogen, —O—C 1-7 alkyl, a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)—O—C 1-7 alkyl, a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, heteroaryl-C 1-5 haloalkyl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, —S(═O) 2 —C 1-7 alkyl, —CF 3 ,

and R 19 and R 20 are each independently H or —C 1-7 alkyl,

 is phenylene or 5- or 6-membered heteroarylene comprising one to three heteroatoms selected from the group comprising N, O or S,

halogen is F, Cl, Br or I, and

n is 1.

3. The compound represented by the chemical formula I, stereoisomers thereof or pharmaceutically acceptable salts thereof according to claim 1 , wherein

X 1 to X 4 are each independently CR 0 or N, wherein at least two of X 1 to X 4 are CR 0 ,

R 0 is hydrogen or halogen,

R 1 is —C 1-5 haloalkyl,

R 2 and R 3 are each independently H, halogen,

 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from group comprising N, O or S, 3- to 7-membered heterocycloalkenyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected

from the group comprising N, O or S,

 phenyl, indolyl,

 (in which at least one hydrogen of said 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered heterocycloalkenyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 phenyl, indolyl,

 can be substituted with R 4 ,

R 4 is halogen, —C 1-7 alkyl, —C 1-7 haloalkyl, —O—C 1-7 alkyl, —C(═O)—C 1-7 alkyl, —C(═O)—C 1-7 alkyl-OH, —C(═O)—O—C 1-7 alkyl, —S(═O) 2 —C 1-7 alkyl, 3- to 7-membered cycloalkyl, 3- to 7-membered halocycloalkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 —C 1-7 alkyl-C(═O)—R 5 , —C 1-7 alkyl-R 7 , —C 1-7 alkyl-O—R 8 , —NR 9 R 10 or —C(═O)—NR 11 R 12 ,

in which R 5 is 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S,

R 7 is 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S or 3- to 7-membered cycloalkyl,

R a is —C 1-7 alkyl,

R 9 and R 10 are each independently —C 1-7 alkyl, and

R 11 and R 12 are each independently H or —C 1-7 alkyl),

R x and R y are each independently —C 1-7 alkyl or —C 1-7 alkyl-NR 15 R 16 ,

(in which R 15 and R 16 are each independently —C 1-7 alkyl),

K is O,

Y is CR a R b or NR c , R c is hydrogen, —C 1-7 alkyl, —C 1-7 alkyl-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-phenyl, —C 1-7 alkyl-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-O—C 1-7 alkyl or —C 1-7 alkyl-NR 19 R 20 , wherein at least one hydrogen of —C 1-7 alkyl, —C 1-7 alkyl-heterocycloalkyl (in this case, heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-phenyl, —C 1-7 alkyl-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-O—C 1-7 alkyl, or —C 1-7 alkyl-NR 19 R 20 can be substituted with —C 1-7 alkyl, —O—C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, heteroaryl-C 1-5 haloalkyl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S or —C(═O)—O—C 1-7 alkyl, and R 19 and R 20 are each independently —C 1-7 alkyl,

 is phenylene,

halogen is F or Br, and

n is 1.

4. The compound represented by the chemical formula I, stereoisomers thereof or pharmaceutically acceptable salts thereof according to claim 1 , wherein

X 1 to X 4 are each independently CR 0 or N, wherein at least two of X 1 to X 4 are CR 0 ,

R 0 is hydrogen or F,

R 1 is CF 2 H,

R 2 and R 3 are each independently H, F, Br,

 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from group comprising N, O or S, 3- to 7-membered heterocycloalkenyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 phenyl, indolyl,

wherein at least one hydrogen of said 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered heterocycloalkenyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 phenyl, indoyl,

 can be substituted with R 4 , R 4 is F, —C 1-7 alkyl, —C 1-7 haloalkyl, —O—C 1-7 alkyl, —C(═O)—C 1-7 alkyl, —C(═O)—C 1-7 alkylOH, —C(═O)—O—C 1-7 alkyl, —S(═O) 2 —C 1-7 alkyl, 3- to 7-membered cycloalkyl, 3- to 7-membered halocycloalkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 —C 1-7 alkyl-C(═O)—R 5 , —C 1-7 alkyl-R 7 , —C 1-7 alkyl-O—R 8 , —NR 9 R 10 or —C(═O)—NR 11 R 12 , in which R 5 is 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, R 7 is 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S or 3-to 7-membered cycloalkyl, R 8 is —C 1-7 alkyl, R 9 and R 10 are each independently —C 1-7 alkyl, and R 11 and 12 are each independently H or —C 1-7 alkyl), R x and R y are each independently —C 1-7 alkyl or —C 1-7 alkyl-NR 15 R 16 , wherein R 15 and R 16 are each independently —C 1-7 alkyl,

K is O,

Y is CR a R b or NR c ,

R a and R b are each independently hydrogen or —C 1-7 alkyl, or R a and R b are linked to each other to form 3- to 7-membered cycloalkyl, R c is hydrogen, —C 1-7 alkyl, —C 1-7 alkyl-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-phenyl, —C 1-7 alkyl-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-O—C 1-7 alkyl or —C 1 -7 alkyl-NR 19 R 20 , wherein at least one hydrogen of —C 1-7 alkyl, —C 1-7 alkyl-heterocycloalkyl (in this case, heterocycloalkyl is 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-phenyl, —C 1-7 alkyl-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-O—C 1-7 alkyl or —C 1-7 alkyl-NR 19 R 20 can be substituted with-C 1-7 alkyl, —O—C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, heteroaryl-C 1-5 haloalkyl wherein the heteroaryl is 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S or —C(═O)—O—C 1-7 alkyl, and R 19 and R 20 are each independently —C 1-7 alkyl,

 is phenylene,

halogen is F or Br, and

n is 1.

5. A compound represented by a following chemical formula II, stereoisomers thereof or pharmaceutically acceptable salts thereof:

wherein,

X 1 to X 4 are each independently CR 0 or N, wherein at least two of X 1 to X 4 are CR 0 ,

in which each R 0 is independently hydrogen, halogen, straight or branched —C 1-7 alkyl, or straight or branched —O—C 1-7 alkyl,

R 1 is straight or branched —C 1-5 haloalkyl,

R 2 and R 3 are each independently H, halogen,

 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from group comprising N, O or S, 3- to 7-membered heterocycloalkenyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 —C 1-7 alkyl, 3- to 7-membered cycloalkyl, 3- to 7-membered cycloalkenyl, cyclopenta-1,3-diene, phenyl, indolyl,

(in which at least one hydrogen of said 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered heterocycloalkenyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 —C 1-7 alkyl, 3- to 7-membered cycloalkyl, 3- to 7-membered cycloalkenyl, cyclopenta-1,3-diene, phenyl, indolyl,

 can be substituted with R 4 ,

R 4 is halogen, —C 1-7 alkyl, —C 1-7 haloalkyl, —O—C 1-7 alkyl, —C(═O)—C 1-7 alkyl, —C(═O)—C 1-7 alkyl-OH, —C(═O)—O—C 1-7 alkyl, —S(═O) 2 —C 1-7 alkyl, 3- to 7-membered cycloalkyl, 3- to 7-membered halocycloalkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S,

 —C 1-7 alkyl-C(═O)—R 5 , —C 1-7 alkyl-C(═O)—O—R 6 , —C 1-7 alkyl-R 7 , —C 1-7 alkyl-O—R 8 , —NR 9 R 10 , —C(═O)—NR 11 R 12 or —C 1-7 alkyl-NR 13 R 14 ,

in which R 5 is —C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, cyclopenta-1,3-diene or phenyl,

R 6 is —C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, cyclopenta-1,3-diene or phenyl,

R 7 is 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, cyclopenta-1,3-diene or phenyl,

R 8 is —C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, cyclopenta-1,3-diene or phenyl,

R 9 and R 10 are each independently H or —C 1-7 alkyl,

R 11 and R 12 are each independently H or —C 1-7 alkyl, and

R 13 and R 14 are each independently H or —C 1-7 alkyl,

R x and R y are each independently —C 1-7 alkyl, —C 1-7 alkyl-NR 15 R 16 , H, —C 1-7 alkyl-O—C 1-7 alkyl, —C(═O)—C 1-7 alkyl, —C(═O)-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)-heterocycloalkyl wherein the heterocycloalkyl is a 3-to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O) cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, —C 1-7 alkyl-O-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S or —C 1-7 alkyl-cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl in which wherein at least one hydrogen of —C 1-7 alkyl, —C 1-7 alkyl-O—C 1-7 alkyl, —C(═O)—C 1-7 alkyl, —C(═O)-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O) cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, —C 1-7 alkyl-O-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S or —C 1-7 alkyl-cycloalkyl wherein the cycloalkyl is a 3-to 7-membered cycloalkyl can be substituted with —C 1-7 alkyl, halogen, —O—C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, —S(═O) 2 —C 1-7 alkyl, —CF 3 ,

 and

R 15 and R 16 are each independently H or —C 1-7 alkyl),

K is O or S,

Y is CR a R b or NR c ,

R a and R b are each independently hydrogen, —C 1-7 alkyl, 3- to 7-membered cycloalkyl, —C 1-7 alkyl-O—C 1-7 alkyl, —C 1-7 alkyl-NR 17 R 18 , 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-C(═O)—C 1-7 alkyl or —C 1-7 alkyl-C(═O)—O—C 1-7 alkyl, or R a and R b are linked to each other to form 3- to 7-membered cycloalkyl,

wherein at least one hydrogen of —C 1-7 alkyl 3- to 7-membered cycloalkyl, —C 1-7 alkyl-O—C 1-7 alkyl, —C 1-7 alkyl-NR 17 R 18 , 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-C(═O)—C 1-7 alkyl or —C 1-7 alkyl-C(═O)—O—C 1-7 alkyl may be substituted with-C 1-7 alkyl, halogen, —O—C 1-7 alkyl, 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, —S(═O) 2 —C 1-7 alkyl, —CF 3 ,

 and

R 17 and R 18 are each independently H or —C 1-7 alkyl, R c is hydrogen, —C 1-7 alkyl, —C 1-7 alkyl-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-phenyl, —C 1-7 alkyl-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-O—C 1-7 alkyl, —C 1-7 alkyl-NR 19 R 20 , —C 1-7 alkyl-cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, a 3- to 7-membered cycloalkyl, a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, cyclopenta-1,3-diene, phenyl, —C(═O)—, —C(═O)-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O) cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, —C(═O)-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)-phenyl, —C(═O)—C 1-7 alkyl, —C(═O)—C 1-7 alkyl-O—C 1-7 alkyl or —C(═O)—C 1-7 alkyl-NR 19 R 20 , wherein at least one hydrogen of —C 1-7 alkyl, —C 1-7 alkyl-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-phenyl, —C 1-7 alkyl-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C 1-7 alkyl-O—C 1-7 alkyl, —C 1-7 alkyl-NR 19 R 20 , —C 1-7 alkyl-cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, a 3- to 7-membered cycloalkyl, a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, cyclopenta-1,3-diene, phenyl, —C(═O)—, —C(═O)-heterocycloalkyl wherein the heterocycloalkyl is a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O) cycloalkyl wherein the cycloalkyl is a 3- to 7-membered cycloalkyl, —C(═O)-heteroaryl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)-phenyl, —C(═O)—C 1-7 alkyl, —C(═O)—C 1-7 alkyl-O—C 1-7 alkyl or —C(═O)—C 1-7 alkyl-NR 19 R 20 , can be substituted with —C 1-7 alkyl, halogen, —O—C 1-7 alkyl, a 3- to 7-membered heterocycloalkyl comprising one to three heteroatoms selected from the group comprising N, O or S, —C(═O)—O—C 1-7 alkyl, a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, heteroaryl-C 1-5 haloalkyl wherein the heteroaryl is a 5- or 6-membered heteroaryl comprising one to three heteroatoms selected from the group comprising N, O or S, 3- to 7-membered cycloalkyl, —S(═O) 2 —C 1-7 alkyl, —CF 3 ,

 and R 19 and R 20 are each independently H or —C 1-7 alkyl,

 is phenylene or 5- or 6-membered heteroarylene comprising one to three heteroatoms selected from the group comprising N, O or S,

halogen is F, Cl, Br or I, and

n is 1.

6. A compound described in a following table, stereoisomers thereof or pharmaceutically acceptable salts thereof:

Compound

Structure

 1

 2

 3

 4

 5

 6

 7

 8

 9

 10

 11

 12

 13

 14

 15

 16

 17

 18

 19

 20

 21

 22

 23

 24

 25

 26

 27

 28

 29

 30

 31

 32

 33

 34

 35

 36

 37

 38

 39

 40

 41

 42

 43

 44

 45

 46

 47

 48

 49

 50

 51

 52

 53

 54

 55

 56

 57

 58

 59

 60

 61

 62

 63

 64

 65

 66

 67

 68

 69

 70

 71

 72

 73

 74

 75

 76

 77

 78

 79

 80

 81

 82

 83

 84

 85

 86

 87

 88

 89

 90

 91

 92

 93

 94

 95

 96

 97

 98

 99

100

101

102

103

104

105

106

107

108

109

110

111

112

113

114

115

116

117

118

119

120

121

122

123

124

125

126

127

128

129

130

131

132

133

134

135

136

137

138

139

140

141

142

143

144

145

146

147

148

149

150

151

152

153

154

155

156

7. A pharmaceutical composition comprising the compound according to claim 1 , stereoisomers thereof or pharmaceutically acceptable salts thereof as an effective component.

8. A method for treating histone deacetylase 6 activity-related diseases, comprising administering a therapeutically effective amount of the compound according to claim 1 , stereoisomers thereof or pharmaceutically acceptable salts thereof.

9. A method according to claim 8 , wherein histone deacetylase 6 activity-related diseases are at least one selected from the group consisting of infectious diseases; neoplasm; endocrinopathy; nutritional and metabolic diseases; mental and behavioral disorders; neurological diseases; eye and ocular adnexal diseases; circulatory diseases; respiratory diseases; digestive diseases; skin and subcutaneous tissue diseases; musculoskeletal system and connective tissue diseases; and teratosis or deformities, and chromosomal aberration.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 25, 2022
From: LEE, CHANG SIK; OH, JUNG TAEK; YUN, HOKEUN; SONG, HYESEUNG; KIM, HYUNJIN MICHAEL
To: CHONG KUN DANG PHARMACEUTICAL CORPORATION
Reel/Frame 059400/0149 →
Priority Claims (1)
KR 10-2019-0064666 · May 31, 2019 · national
Continuity (1)
Related Publication 20230079386A1 · Mar 16, 2023
References Cited (268)
US 4871753A · Rorh · 1989 [cited by applicant]
US 6075039A · Gallagher et al. · 2000 [cited by applicant]
US 8901156B2 · Baloglu et al. · 2014 [cited by applicant]
US 8981084B2 · Baloglu et al. · 2015 [cited by applicant]
US 9670193B2 · Hebach et al. · 2017 [cited by applicant]
US 10464911B2 · Lee et al. · 2019 [cited by applicant]
US 10494355B2 · Kim et al. · 2019 [cited by applicant]
US 10538498B2 · Lee et al. · 2020 [cited by applicant]
US 10584117B2 · Lee et al. · 2020 [cited by applicant]
US 10717716B2 · Lee et al. · 2020 [cited by applicant]
US 11958844B2 · Lee et al. · 2024 [cited by applicant]
US 20050288282A1 · Delorme et al. · 2005 [cited by applicant]
US 20060058298A1 · Delorme et al. · 2006 [cited by applicant]
US 20070293530A1 · Smil et al. · 2007 [cited by applicant]
US 20120027874A1 · Charrier et al. · 2012 [cited by applicant]
US 20120289495A1 · Baloglu et al. · 2012 [cited by applicant]
US 20130059883A1 · Baloglu et al. · 2013 [cited by applicant]
US 20140005133A1 · Trivedi et al. · 2014 [cited by applicant]
US 20140005164A1 · Varrone et al. · 2014 [cited by applicant]
US 20140142105A1 · Hebach et al. · 2014 [cited by applicant]
US 20140329825A1 · Hebach et al. · 2014 [cited by applicant]
US 20150307497A1 · Sugimoto et al. · 2015 [cited by applicant]
US 20160244449A1 · Lu et al. · 2016 [cited by applicant]
US 20170015809A1 · Hawkins et al. · 2017 [cited by applicant]
US 20170145012A1 · Buckmelter et al. · 2017 [cited by applicant]
US 20180215743A1 · Lee et al. · 2018 [cited by applicant]
US 20180230113A1 · Lee et al. · 2018 [cited by applicant]
US 20180230114A1 · Lee et al. · 2018 [cited by applicant]
US 20180251437A1 · Lee et al. · 2018 [cited by applicant]
US 20180273495A1 · Kim et al. · 2018 [cited by applicant]
US 20190008836A1 · Kaieda et al. · 2019 [cited by applicant]
US 20210188831A1 · Lee et al. · 2021 [cited by applicant]
US 20210355089A1 · Chern et al. · 2021 [cited by applicant]
US 20230092890A1 · Lee et al. · 2023 [cited by applicant]
CN 101263121 · 2008 [cited by applicant]
CN 102448461 · 2012 [cited by applicant]
CN 102802623 · 2012 [cited by applicant]
CN 103221047 · 2013 [cited by applicant]
CN 103339111 · 2013 [cited by applicant]
CN 104744446 · 2015 [cited by applicant]
CN 103998446 · 2016 [cited by applicant]
CN 107438607 · 2017 [cited by applicant]
CN 108026056 · 2018 [cited by applicant]
CN 108137518 · 2018 [cited by applicant]
CN 108473495 · 2018 [cited by applicant]
CN 108699048 · 2018 [cited by applicant]
CN 114269739 · 2022 [cited by applicant]
EA 201491060 · 2014 [cited by applicant]
EP 0816356 · 1998 [cited by applicant]
EP 3327019 · 2018 [cited by applicant]
EP 3330259 · 2018 [cited by applicant]
JP H10059962 · 1998 [cited by applicant]
JP 2005513123 · 2005 [cited by applicant]
JP 2009542752 · 2009 [cited by applicant]
JP 2011008205 · 2011 [cited by applicant]
JP 2011502133 · 2011 [cited by applicant]
JP 2012211149 · 2012 [cited by applicant]
JP 2013517278 · 2013 [cited by applicant]
JP 2013517281 · 2013 [cited by applicant]
JP 2013533279 · 2013 [cited by applicant]
JP 2014513071 · 2014 [cited by applicant]
JP WO2014077401 · 2014 [cited by applicant]
JP 2014520794 · 2014 [cited by applicant]
JP 2014524922 · 2014 [cited by applicant]
JP 2014533721 · 2014 [cited by applicant]
JP 2014533734 · 2014 [cited by applicant]
JP 2018511573 · 2018 [cited by applicant]
JP 2018521110 · 2018 [cited by applicant]
JP 2019504821 · 2019 [cited by applicant]
JP 2021532130 · 2021 [cited by applicant]
JP 2022529695 · 2022 [cited by applicant]
JP 2022537904 · 2022 [cited by applicant]
KR 100265385 · 2000 [cited by applicant]
KR 100903743 · 2009 [cited by applicant]
KR 101262870 · 2013 [cited by applicant]
KR 101320198 · 2013 [cited by applicant]
KR 20130112911 · 2013 [cited by applicant]
KR 20140097459 · 2014 [cited by applicant]
KR 20147017436 · 2014 [cited by applicant]
KR 101561860 · 2015 [cited by applicant]
KR 20170013186 · 2017 [cited by applicant]
KR 1020220012243 · 2022 [cited by applicant]
RU 2515611 · 2012 [cited by applicant]
WO WO2003028729 · 2003 [cited by applicant]
WO WO2007011626 · 2007 [cited by applicant]
WO WO2007032445 · 2007 [cited by applicant]
WO WO2007093827 · 2007 [cited by applicant]
WO WO2007107758 · 2007 [cited by applicant]
WO WO2009010479 · 2009 [cited by applicant]
WO WO2010109148 · 2010 [cited by applicant]
WO WO2010123933 · 2010 [cited by applicant]
WO WO2010126002 · 2010 [cited by applicant]
WO WO2011011186 · 2011 [cited by applicant]
WO WO2011088181 · 2011 [cited by applicant]
WO WO2011088192 · 2011 [cited by applicant]
WO WO2011091213 · 2011 [cited by applicant]
WO WO2011104680 · 2011 [cited by applicant]
WO WO2011133888 · 2011 [cited by applicant]
WO WO2012011592 · 2012 [cited by applicant]
WO WO2012013716 · 2012 [cited by applicant]
WO WO2012136492 · 2012 [cited by applicant]
WO WO2013008162 · 2013 [cited by applicant]
WO WO2013041407 · 2013 [cited by applicant]
WO WO2013052110 · 2013 [cited by applicant]
WO WO2013066833 · 2013 [cited by applicant]
WO WO2013066835 · 2013 [cited by applicant]
WO WO2013066838 · 2013 [cited by applicant]
WO WO2013066839 · 2013 [cited by applicant]
WO WO2013080120 · 2013 [cited by applicant]
WO WO2013134467 · 2013 [cited by applicant]
WO WO2015033301 · 2015 [cited by applicant]
WO WO2015087151 · 2015 [cited by applicant]
WO WO2016082930 · 2016 [cited by applicant]
WO WO2016134320 · 2016 [cited by applicant]
WO WO2017014170 · 2017 [cited by applicant]
WO WO2017014321 · 2017 [cited by applicant]
WO WO2017018803 · 2017 [cited by applicant]
WO WO2017018804 · 2017 [cited by applicant]
WO WO2017018805 · 2017 [cited by applicant]
WO WO2017023133 · 2017 [cited by applicant]
WO WO2017065473 · 2017 [cited by applicant]
WO WO2017222951 · 2017 [cited by applicant]
WO WO2017222952 · 2017 [cited by applicant]
WO WO2018213364 · 2018 [cited by applicant]
WO WO2020022794 · 2020 [cited by applicant]
WO WO2020212479 · 2020 [cited by applicant]
WO WO2021127643 · 2021 [cited by applicant]
Schafer et al. Drug Discovery Today 2008, 13 (21/22), 913-916 (Year: 2008). [cited by examiner]
Horig et al. Journal of Translational Medicine 2004, 2(44) (Year: 2004). [cited by examiner]
Zhang et al. J Hematol Oncol, 2018 11, 111 (Year: 2018). [cited by examiner]
Zhang et al. Circulation. 2014. 129(3). 346-358 (Year: 2014). [cited by examiner]
Office Action in Canadian Appln. No. 3,139,026, mailed on Sep. 14, 2023, 5 pages. [cited by applicant]
Office Action in Chinese Appln. No. 202080039276.4, mailed on Nov. 24, 2024, 17 pages (with English translation). [cited by applicant]
Office Action in Chinese Appln. No. 202080039677, mailed on Nov. 25, 2023, 13 pages (with English translation). [cited by applicant]
Office Action in Indonesian Appln. No. P00202110627, mailed on May 22, 2023, 6 pages (with English translation). [cited by applicant]
Office Action in Indonesian Appln. No. P00202111108, mailed on Jul. 6, 2023, 6 pages (with English translation). [cited by applicant]
Office Action in New Zealand Appln. No. 782015, mailed on Mar. 7, 2024, 3 pages. [cited by applicant]
Office Action in New Zealand Appln. No. 782551, mailed on Mar. 7, 2024, 3 pages. [cited by applicant]
Office Action in Vietnamese Appln. No. 1-2021-07143, mailed on Dec. 27, 2023, 4 pages (with English translation). [cited by applicant]
Office Action in Vietnamese Appln. No. 1-2021-07370, mailed on Dec. 27, 2023, 4 pages (with English translation). [cited by applicant]
Office Action for Korean Appln, No. 10-2020-0065508, dated Mar. 2, 2022, 15 pages (with Machine Translation). [cited by applicant]
ACS RN 904568-68-9, “Benz amide, 3,4,5-trimethoxy-N-[4-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]phenyl]” STN-Registry, Aug. 25, 2006, 1 page. [cited by applicant]
ACS RN 904653-05-0, “Benzamide, 3-methoxy-N-[4-[5-(trichloromethyl)-1,3,4-oxadiazol-2-yl]phenyl]”, STN-Registry, dated Aug. 25, 2006, 1 page. [cited by applicant]
Office Action and Search Report for Chinese Application No. 201680044430.0, dated Aug. 21, 2020. 9 pages (with English translation). [cited by applicant]
Office Action and Search Report for Chinese Application No. 201680053218.0, dated Nov. 8, 2020, 14 pages (with English translation). [cited by applicant]
Office Action and Search Report for Chinese Application No. 201680058155.8, dated Jan. 6, 2021, 13 pages (with English translation). [cited by applicant]
Office Action and Search Report for Chinese Application No. 201680072029.8, dated Oct. 26, 2020, 12 pages (with English translation). [cited by applicant]
U.S. Appl. No. 17/263,333, filed Jan. 26, 2021, Chang Sik Lee. [cited by applicant]
Baijika, et al., “Synthesis and biological activities of 1, 3, 4-oxadiazole derivatives: A Review of Literature,” Int. J. Adv. Res., [Published] Jan. 2018, vol. 6, No. 1, pp. 1114-1122. [cited by applicant]
Bolden et al., “Anticancer activities of histone deacetylase inhibitors”, National Reviews, Drug Discovery, vol. 5, Sep. 2006, pp. 769-784. [cited by applicant]
Hassig et al., “Nuclear histone acetylases and deacetylases and transcriptional regulation: HATs off to HDACs,” Current Opinion In Chemical Biology 1997, 1, pp. 300-308. [cited by applicant]
Hu et al., “HDAC6 α-tubulin deacetylase: A potential therapeutic target in neurodegenerative diseases,” Journal of the Neurological Sciences, 304, 2011, pp. 1-8. [cited by applicant]
Matthias et al., “Mice Lacking Histone Deacetylase 6 Have Hyperacetylated Tubulin but Are Viable and Develop Normally,” Molecular and Cellular Biology, Mar. 2008, vol. 28, pp. 1688-1701. [cited by applicant]
Methot et al., “Exploration of the internal cavity of histone deacetylase (HDAC) with selective HDAC1/HDAC2 inhibitors (SHI-1:2),” Bioorganic & Medicinal Chemistry Letters, 18, (2008), pp. 973-978. [cited by applicant]
Notice of Allowance in Korean Appln. No. 2018-0087455, dated Oct. 7, 2021, 4 pages (with English translation). [cited by applicant]
Office Action for TW108126316, dated Oct. 22, 2020 and English translation, 7 pages. [cited by applicant]
Office Action for TW109118219, dated Mar. 19, 2021 and English translation, 9 pages. [cited by applicant]
Office Action for TW109118221, dated Apr. 15, 2021 and English translation, 9 pages. [cited by applicant]
Office Action in Russian Appln. No. 2021104625, dated Jul. 23, 2021, 22 pages (with English translation). [cited by applicant]
PCT International Preliminary Report on Patentability in International Appln. No. PCT/KR2019/009228, dated Feb. 4, 2021, 6 pages. [cited by applicant]
PCT International Search Report and Written Opinion in International Application No. PCT/IB2020/055109, dated Sep. 4, 2020, 10 pages. [cited by applicant]
PCT International Search Report and Written Opinion in International Application No. PCT/IB2020/055110, dated Sep. 4, 2020, 12 pages. [cited by applicant]
PCT International Search Report and Written Opinion in International Application No. PCT/KR2019/009228, Nov. 11, 2019, 8 pages. [cited by applicant]
Piekarz et al., “Clinical Toxicities of Histone Deacetylase Inhibitors”, Pharmaceuticals 2010, 3, pp. 2751-2767. [cited by applicant]
Santo et al., “Preclinical activity, pharmacodynamic, and pharmacokinetic properties of a selective HDAC6 inhibitor, ACY-1215, in combination with bortezomib in multiple myeloma,” Blood, Mar. 15, 2012, vol. 119, No. 11,… [cited by applicant]
Vishwakarma et al., “Tubastatin, a selective histone deacetylase 6 inhibitor shows anti-inflammatory and anti-rheumatic effects,” International Immunopharmacology, 2013, 16, pp. 72-78. [cited by applicant]
Warrell et al., “Therapeutic Targeting of Transcription in Acute Promyelocytic Leukemia by Use of an Inhibitor of Histone Deacetylase,” Journal of the National Cancer Institute, vol. 90, No. 21, Nov. 4, 1998, pp. 1621-1… [cited by applicant]
Wiest et al., “Computational Exploration of Zinc Binding Groups for HDAC Inhibition,” J. Org. Chem., May 17, 2013, 78, pp. 5051-5055. [cited by applicant]
Witt et al., “HDAC family: What are the cancer relevant targets?,” Cancer Letters 277, 2009, 2, pp. 8-21. [cited by applicant]
Woster et al., “Discovery of a new class of histone deacetylase inhibitors with a novel zinc binding group,” Med. Chem. Commun., 2015, online publication, 6 pages. [cited by applicant]
Yao et al., “HDAC6 Regulates Hsp90 Acetylation and Chaperone-Dependent Activation of Glucocorticoid Receptor,” Molecular Cell, vol. 18, May 27, 2005, pp. 601-607. [cited by applicant]
Belikov, “Farmatsevticheskaya khimiya [Pharmaceutical Chemistry]”, textbook, 4th ed., M.: “MEDpress-inform”, Moscow, 2007, 622 p, pp. 27-29 (with English translation, 14 pages in total). [cited by applicant]
Gavrilov, “Pharmaceutical technology. The manufacturing of drugs,” Textbook, M.: GEOTAR-Media, 2010, 624 p, p. 20 (with Machine translation, 6 pages in total). [cited by applicant]
Office Action in Malaysian Appln. No. PI2021006507, mailed on Sep. 25, 2024, 3 pages (with English translation). [cited by applicant]
Office Action in Mexican Appln. No. MX/a/2021/014315, mailed on Jul. 15, 2024, 9 pages (with English translation). [cited by applicant]
Office Action in New Zealand Appln. No. 782015, mailed on Sep. 24, 2024, 3 pages. [cited by applicant]
Dyson G., May P. “Chemistry of synthetic drugs”, translated from English by Professor M.L. Belenky, Publishing House “MIR”, Moscow, 1964, pp. 12-19 (with English translation, 21 pages in total). [cited by applicant]
Office Action in Mexican Appln. No. MX/a/2021/014372, mailed on Jul. 16, 2024, 8 pages (with English translation). [cited by applicant]
Popular Medical Encyclopedia, editor-in-chief V.I. Pokrovsky, 4th ed., St., “Book”, 1997, p. 317 (drugs) (with Machine translation, 5 pages in total). [cited by applicant]
Cancer [online], “Cancer,” Jun. 27, 2007, retrieved on Jul. 6, 2007, retrieved from URL <http://www.nlm.nih.gov/mededlineplus/cancer.html>, 10 pages. [cited by applicant]
CAS No. 904635-69-4, “4-Morpholinecarboxamide, N-[4-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]phenyl],” STN Easy, dated Aug. 25, 2006, 1 page. [cited by applicant]
CAS No. 904652-71-7, “4-Morpholinecarboxamide, N-[4-[5-(dichloromethyl)-1,3,4-oxadiazol-2-yl]phenyl],” STN Easy, dated Aug. 25, 2006, 1 page. [cited by applicant]
CAS No. 904653-13-0, “4-Morpholinecarboxamide, N-[4-[5-(trichloromethyl)-1, 3,4-oxadiazol-2-yl]phenyl],” STN Easy, dated Aug. 25, 2006, 1 page. [cited by applicant]
Chemical Abstract compound RN No. 1355844-43-7, STN Express, dated Feb. 8, 2012, 1 page. [cited by applicant]
Chemical Abstract compound RN No. 1384673-31-7, STN Express, dated Jul. 27, 2012, 1 page. [cited by applicant]
Chemical Abstract compound RN No. 1436149-02-8, STN Express, dated Jun. 9, 2013, 1 page. [cited by applicant]
Chemical Abstract compound RN No. 1708354-35-1, STN Express, dated May 20, 2015, 1 page. [cited by applicant]
Chemical Abstract compound RN No. 1790675-44-3, STN Express, dated Jun. 29, 2015, 1 page. [cited by applicant]
Chemical Abstract compound RN No. 1798074-73-3, STN Express, dated Jul. 9, 2015, 1 page. [cited by applicant]
Chemical Abstract compound RN No. 904653-15-2, STN Express, dated Aug. 25. 2006, 1 page. [cited by applicant]
Chemical Abstract compound RN No. 904653-17-4, STN Express, Aug. 25, 2006, 1 page. [cited by applicant]
Chemical Abstract compound RN No. 904653-20-9, STN Express, dated Aug. 25, 2006, 2 pages. [cited by applicant]
Chemical Abstract compound RN No. 904653-21-0, STN Express, dated Aug. 25, 2006, 1 page. [cited by applicant]
Chemical Abstract compound RN No. 904653-22-1, STN Express, dated Aug. 25, 2006, 1 page. [cited by applicant]
Chen et al., “Computational exploration of zine binding groups for HDAC inhibition,” J. Org. Chem., May 2013, 78(10):5051-5055. [cited by applicant]
Chen et al., “Discovery of 2-methylpyridine-based biaryl amides as y-secretase modulators for the treatment of Alzheimer's disease, ”Bioorg. Med. Chem, 2013, 23(23):6447-6454. [cited by applicant]
Decision to Grant in Russian Appln. No. 2021104625, dated Dec. 3, 2021, 29 pages (with English Translation). [cited by applicant]
El-Din. et al., “Synthesis and in vitro antiproliferative activity of new 1,3,4-oxadiazole derivatives possessing sulfonamide moiety,” Eur. J. Med. Chem, Jan. 2015, 90:45-52. [cited by applicant]
Extended European Search Report in European Appln. No. 16830836.9, dated Dec. 19, 2018, 7 pages. [cited by applicant]
Extended European Search Report in European Appln. No. 16830837.7, dated Dec. 17, 2018, 9 pages. [cited by applicant]
Extended European Search Report in European Appln. No. 16830838.5, dated Nov. 19, 2018, 7 pages. [cited by applicant]
Extended European Search Report in European Appln. No. 16833369.8, dated Apr. 1, 2019, 6 pages. [cited by applicant]
Golub et al., “Molecular Classification of Cancer: Class Discovery and Class Prediction by Gene Expression Monitoring,” Science, Oct. 1991, 286:531-537. [cited by applicant]
International Preliminary Report on Patentability and Written Opinion for International Appln. No. PCT/KR2016/008214, dated Jan. 30, 2018, 8 pages. [cited by applicant]
International Preliminary Report on Patentability and Written Opinion for International Appln. No. PCT/KR2016/008216, dated Jan. 30, 2018, 9 pages. [cited by applicant]
International Preliminary Report on Patentability and Written Opinion for International Appln. No. PCT/KR2016/008218, dated Jan. 30, 2018, 8 pages. [cited by applicant]
International Preliminary Report on Patentability and Written Opinion for International Appln. No. PCT/KR2016/008622, dated Feb. 6, 2018, 8 pages. [cited by applicant]
International Preliminary Report on Patentability and Written Opinion for International Appln. No. PCT/KR2016/011355, dated Apr. 17, 2018, 6 pages. [cited by applicant]
International Search Report for International Appln. No. PCT/KR2016/008214, dated Nov. 24, 2016, 5 pages. [cited by applicant]
International Search Report for International Appln. No. PCT/KR2016/008216, dated Nov. 21, 2016, 12 pages (with English Translation). [cited by applicant]
International Search Report for International Appln. No. PCT/KR2016/008218, dated Nov. 21, 2016, 5 pages. [cited by applicant]
International Search Report for International Appln. No. PCT/KR2016/008622, dated Feb. 17. 2017, 5 pages. [cited by applicant]
International Search Report for International Appln. No. PCT/KR2016/011355, dated Jan. 26, 2017, 5 pages. [cited by applicant]
Lala et al., “Role of nitric oxide in tumor progression: Lessons from experimental tumors,” Cancer Metastasis Rev., 1998, 17(1):91-106. [cited by applicant]
Manku, et al., “Synthesis and evaluation of lysine derived sulfamides as histone deacetylase inhibitors,” Bioorg. Med. Chem. Lett., Feb. 2009, 19:1866-1870. [cited by applicant]
Murphy et al., “Regulation of the Dynamics of hsp90 Action on the Glucocorticoid Receptor by Acetylation/Deacetylation of the Chaperone,” J. Biol. Chem., Oct. 2005, 280(40):33792-33799. [cited by applicant]
Office Action for Australian Appln. No. 2016299484, dated Aug. 28, 2018, 6 pages. [cited by applicant]
Office Action for Australian Appln. No. 2016299484, dated Dec. 18, 2018, 3 pages. [cited by applicant]
Office Action for Australian Appln. No. 2016299485, dated Sep. 13, 2018, 7 pages. [cited by applicant]
Office Action for Australian Appln. No. 2016299486, dated Jul. 21, 2018, 5 pages. [cited by applicant]
Office Action for Australian Appln. No. 2016303891, dated Nov. 16, 2018, 7 pages. [cited by applicant]
Office Action for Canadian Appln. No. 2987570, dated Oct. 18, 2018, 5 pages. [cited by applicant]
Office Action for Canadian Appln. No. 2993918, dated Dec. 4, 2018, 5 pages. [cited by applicant]
Office Action for Canadian Appln. No. 2993929, dated Dec. 4, 2018, 4 pages. [cited by applicant]
Office Action for Indian Appln. No. 201727037873, dated May 21, 2019, 7 pages. [cited by applicant]
Office Action for Indian Appln. No. 201817006324, dated Jun. 27, 2019, 6 pages. [cited by applicant]
Office Action for Japanese Appln. No. 2018-503804, dated Feb. 15, 2019, 4 pages (with English Translation). [cited by applicant]
Office Action for Japanese Appln. No. 2018-504096, dated Jan. 8, 2019, 5 pages (with English Translation). [cited by applicant]
Office Action for Japanese Appln. No. 2018-504720, dated Jan. 8, 2019, 19 pages (with English Translation). [cited by applicant]
Office Action for Japanese Appln. No. 2018-505725, dated Sep. 12, 2018, 3 pages. [cited by applicant]
Office Action for Japanese Appln. No. 2021-503874, dated Feb. 8, 2022, 7 pages (with English Translation). [cited by applicant]
Office Action for Korean Appln, No. 10-2016-0095332, dated May 9, 2017, 15 pages. [cited by applicant]
Office Action for Korean Appln, No. 10-2016-0095334, dated May 9, 2017, 17 pages. [cited by applicant]
Office Action for Korean Appln, No. 10-2016-0099508, dated May 9, 2017. 20 pages. [cited by applicant]
Office Action for Korean Appln, No. 10-2016-0131245, dated May 9, 2017, 7 pages. [cited by applicant]
Office Action for New Zealand Appln. No. 739211, dated Jun. 14, 2018, 3 pages. [cited by applicant]
Office Action for Russian Appln. No. 2018106877, dated Oct. 18, 2018, 16 pages (with English translation). [cited by applicant]
Office Action for Russian Appln. No. 2018106904, dated Sep. 20, 2018, 14 pages (with English translation). [cited by applicant]
Office Action for Russian Appln. No. 2018106914, dated Nov. 15, 2018, 14 pages (with English translation). [cited by applicant]
Office Action for Taiwanese Appln. No. 105132939, dated Nov. 2, 2017, 8 pages (with English translation). [cited by applicant]
Othman et al., “1,3,4-Oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole derivatives as potential antibacterial agents,” Arab. J. Chem., 2014:1-16. [cited by applicant]
Pal et al., “Hydroxamic acid—A novel molecule for anticancer therapy,” J. Adv. Pharm. Technol. Res., 2012, 3(2):92-99. [cited by applicant]
Rajak et al., “2,5-Disubstituted-1,3,4-oxadiazoles/thiadiazole as surface recognition moiety: Design and synthesis of novel hydroxamic acid based histone deacetylase inhibitors,” Bioorg. Med. Chem. Lett., Aug. 2011, 21:… [cited by applicant]
Rossi et al., “4-N-Hydroxy-4-[ 1-( sulfonyl )piperidin-4-yl ]-butyramides as HDAC inhibitors,” Bioorg. Med. Chem. Lett., Sep. 2011, 21:6767-6769. [cited by applicant]
Extended European Search Report in European Appln. No. 20814548.2, dated Nov. 8, 2022, 5 pages. [cited by applicant]
Extended European Search Report in European Appln. No. 20815468.2, dated May 4, 2023, 13 pages. [cited by applicant]
Notice of Allowance in Australian Appln. No. 2020284167, dated May 1, 2023, 3 pages. [cited by applicant]
Notice of Allowance in Korean Appln. No. 2020-0065507, dated Nov. 10, 2022, 10 pages (with English translation). [cited by applicant]
Office Action for Australian Appln. No. 2020284167, dated Nov. 3, 2022, 3 pages. [cited by applicant]
Office Action for Australian Appln. No. 2020284606, dated Aug. 11, 2022, 8 pages. [cited by applicant]
Office Action for Canadian Appln. No. 3136223, dated Nov. 30, 2022, 4 pages. [cited by applicant]
Office Action for Canadian Appln. No. 3139026, dated Dec. 14, 2022, 6 pages. [cited by applicant]
Office Action for Indian Appln. No. 202137058528, dated Jul. 6, 2022, 5 pages. [cited by applicant]
Office Action for Indian Appln. No. 202137061193, dated Jul. 7, 2022, 6 pages. [cited by applicant]
Office Action for Japanese Appln. No. 2021-571486, dated Jan. 10, 2023, 12 pages (with English Translation). [cited by applicant]
Office Action for Japanese Appln. No. 2021-571498, dated Nov. 8, 2022, 12 pages (with English Translation). [cited by applicant]
Office Action for Malaysian Appln. No. PI2021006507, dated May 22, 2023, 4 pages. [cited by applicant]
Office Action for Russian Appln. No. 2021139516, dated Aug. 11, 2022, 20 pages (with English Translation). [cited by applicant]
Office Action for Russian Appln. No. 2021139540, dated Aug. 17, 2022, 32 pages (with English Translation). [cited by applicant]
Office Action in Chinese Appln. No. 201980049375.8, mailed on Sep. 20, 2023, 13 pages (with English translation). [cited by applicant]
Office Action in Malaysia Appln. No. PI2021000199, mailed on Dec. 1, 2023, 2 pages (with English translation). [cited by applicant]
Office Action in Mexico Appln. No. MX/a/2021/000737, mailed on Jun. 15, 2023, 8 pages (with English translation). [cited by applicant]
Office Action in New Zealand Appln. No. 771899, mailed on Aug. 22, 2023, 4 pages. [cited by applicant]
Office Action in Vietnam Appln. No. 51472w/SHTT-SC, mailed on Aug. 23, 2023, 4 pages (with English translation). [cited by applicant]
Silverman, “The Organic Chemistry of Drug Design and Drug Action,” Second Edition, 2008, pp. 17-23. [cited by applicant]
Patani, G. A et al. Bioisosterism: A Rational Approach in Drug Design. Chemical reviews 1996, vol. 96, 8: 3147-3176. (Year: 1996). [cited by applicant]
U.S. Appl. No. 17/263,333 (U.S. Pat. No. 11,958,844), filed Jan. 26, 2021 (Apr. 16, 2024), Chang Sik Lee. [cited by applicant]
U.S. Appl. No. 17/614,967, filed Nov. 29, 2021, Chang Sik Lee. [cited by applicant]