IP Library Granted Patent US 12,534,457
Granted Patent B2
US 12,534,457 · App. 18/731,285 · Granted Jan 27, 2026

Heteroaryl derivative compounds, and uses thereof

Inventors: Youn Ho Lee (Incheon, KR); Seon Ah Hwang (Incheon, KR); In Seob Shim (Incheon, KR); Hyeon Ho Jeon (Incheon, KR); Woo Mi Do (Incheon, KR); Hee Sun Ryu (Incheon, KR); Jung Beom Son (Incheon, KR); Nam Doo Kim (Incheon, KR); Sung Hwan Kim (Incheon, KR); Hong Ryul Jung (Incheon, KR); Young Yi Lee (Incheon, KR)
Assignee: Voronoi Inc.
C07D413/14C07D413/04C07D471/04C07D471/10C07D487/04C07D487/08C07D487/10C07D498/04C07D498/08C07F9/6584
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 12,534,457
App. No.
18/731,285
Granted
Jan 27, 2026
Kind
B2
Abstract

The present disclosure relates to a heteroaryl derivative and uses thereof. The heteroaryl derivative of the present disclosure exhibits excellent inhibitory activity against EGFR and/or HER2, and thus may be usefully employed as a therapeutic agent for EGFR- and/or HER2-related diseases.

Claims (27)

1 . A compound represented by the following Chemical Formula 1B, an optical isomer thereof, or a pharmaceutically acceptable salt thereof:

wherein

Y is phenyl in which at least one H of the phenyl ring may be substituted with -halo, L is —(CH 2 ) m —, or null,

m is 0 or 1,

a ring Z is phenyl or 5- to 6-membered heteroaryl in which at least one H of the phenyl or 5- to 6-membered heteroaryl ring may be substituted with —C 1-3 alkyl, —C 1-3 haloalkyl, —C 1-3 alkenyl, —O—C 1-3 alkyl, —O—C 1-3 haloalkyl, —C(═O)—C 1-3 alkyl, -halo, or Z 1 , wherein at least one H of the phenyl in the meta position relative to the L is unsubstituted or substituted with at least one selected from the group consisting of —C 1-3 alkyl, —C 1-3 alkenyl, —O—C 1-3 alkyl, —O—C 1-3 haloalkyl, —C(═O)—C 1-3 alkyl, -halo, and Z 1 when the ring Z is phenyl,

Z 1 is 3- to 7-membered cycloalkyl, 5- to 7-membered heterocycloalkyl, or heteroaryl in which the 5- to 7-membered heterocycloalkyl contains, in the ring, at least one selected from the group consisting of N and O, and at least one H of the 5- to 7-membered heterocycloalkyl or heteroaryl ring may be substituted with —C 1-3 alkyl, —N(C 1-3 alkyl) (C 1-3 alkyl), or Z 2 ,

Z 2 is 5- to 7-membered heterocycloalkyl or 6- to 10-membered heterobicycloalkyl in which the 5- to 7-membered heterocycloalkyl or 6- to 10-membered heterobicycloalkyl contains, in the ring, at least one selected from the group consisting of N and O, and at least one H of the 5- to 7-membered heterocycloalkyl or 6- to 10-membered heterobicycloalkyl ring may be substituted with —C 1-6 alkyl, —C 1-3 hydroxyalkyl, —C 1-3 alkenyl, —C 1-3 alkyl-S(═O) 2 —C 1-3 alkyl, ═O, 3- to 7-membered cycloalkyl, or Z 3 , and

Z 3 is 4- to 6-membered heterocycloalkyl or —C 1-3 alkyl-heterocycloalkyl in which the 4- to 6-membered heterocycloalkyl or —C 1-3 alkyl-heterocycloalkyl contains, in the ring, at least one selected from the group consisting of N and O.

2 . A compound, an optical isomer thereof, or a pharmaceutically acceptable salt thereof selected from the group consisting of the following compounds:

3 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

4 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

5 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

6 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

7 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

8 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

9 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

10 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

11 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

12 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

13 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

14 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

15 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

16 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 selected from the group consisting of the following compounds:

17 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 having the formula

18 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 having the formula

19 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 having the formula

20 . The compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of claim 2 having the formula

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2024
From: LEE, YOUN HO; HWANG, SEON AH; SHIM, IN SEOB; JEON, HYEON HO; DO, WOO MI; RYU, HEE SUN; SON, JUNG BEOM; KIM, NAM DOO
To: VORONOIBIO INC.
Reel/Frame 067588/0028 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2024
From: KIM, SUNG HWAN; JUNG, HONG RYUL; LEE, YOUNG YI
To: VORONOI INC.
Reel/Frame 067588/0033 →
MERGER Recorded Jun 1, 2024
From: VORONOIBIO INC.
To: VORONOI INC.
Reel/Frame 067588/0038 →
Priority Claims (1)
KR 10-2021-0063733 · May 17, 2021 · national
Continuity (2)
Continuation 17927324
Related Publication 20240317730A1 · Sep 26, 2024
References Cited (29)
US 7514445B2 · Freyne et al. · 2009 [cited by applicant]
US 8552002B2 · Ding et al. · 2013 [cited by applicant]
US 8962834B2 · Baumann et al. · 2015 [cited by applicant]
US 11440899B2 · Karra et al. · 2022 [cited by applicant]
US 12037330B2 · Lee · 2024 [cited by examiner]
US 20170313714A1 · Wei et al. · 2017 [cited by applicant]
US 20220162203A1 · Lee et al. · 2022 [cited by applicant]
US 20220242870A1 · Jo et al. · 2022 [cited by applicant]
US 20230322753A1 · Lee et al. · 2023 [cited by applicant]
EP 1761505B1 · 2011 [cited by applicant]
EP 2257541B1 · 2013 [cited by applicant]
EP 3943491A1 · 2022 [cited by applicant]
KR 1020170066650A · 2017 [cited by applicant]
KR 1020200111644A · 2020 [cited by applicant]
KR 1020200133188A · 2020 [cited by applicant]
WO 2019010295A1 · 2019 [cited by applicant]
WO 2020190119A1 · 2020 [cited by applicant]
WO 2020235902A1 · 2020 [cited by applicant]
WO 2022060196A1 · 2022 [cited by applicant]
WO 2022131741A1 · 2022 [cited by applicant]
International Patent Application PCT/KR2022/006994 International Search Report dated Aug. 29, 2022. [cited by applicant]
International Patent Application PCT/KR2022/O06994 Written Opinion dated Aug. 29, 2022. [cited by applicant]
Di Fiore et al., “erbB-2 Is a Potent Oncogene When Overexpressed in NIH/3T3 Cells”, Science, vol. 237, No. 481, pp. 178-182 (1987). [cited by applicant]
Hardwick et al., “Immunohistochemical detection of p53 and c-erbB-2 in oesophageal carcinoma; no correlation with prognosis”, Eur. J. Surg. Oncol., vol. 23, pp. 30-35 (1997). [cited by applicant]
Korkaya et al., “HER2 regulates the mammary stem/progenitor cell population driving tumorigenesis and invasion”, Oncogene, vol. 27, No. 47, pp. 6120-6130 (2008). [cited by applicant]
Niederst et al., “The Allelic Context of the C797S Mutation Acquired upon Treatment with Third-Generation EGFR Inhibitors Impacts Sensitivity to Subsequent Treatment Strategies”, Clin. Cancer Res., vol. 21, No. 17, pp. … [cited by applicant]
Thress et al., “Acquired EGFR C797S mutation mediates resistance to AZD9291 in non-small cell lung cancer harboring EGFR T790M”, Nature Medicine, vol. 21, pp. 560-562 (2015). [cited by applicant]
Notice of Allowance & Notice of Allowability of U.S. Appl. No. 17/927,324 dated Mar. 4, 2024. [cited by applicant]
Corrected Notice of Allowability of U.S. Appl. No. 17/927,324 dated Mar. 15, 2024. [cited by applicant]