IP Library › Granted Patent US 12,559,492
Granted Patent B2
US 12,559,492 · App. 18/084,380 · Granted Feb 24, 2026

BRAF degraders

Inventors: Christopher G. Nasveschuk (Stoneham, MA); Martin Duplessis (Somerville, MA); Mark E. Fitzgerald (Newton, MA); Victoria Garza (San Antonio, TX); Andrew Charles Good (Watertown, MA); Katrina L. Jackson (Weston, MA); Yanke Liang (Belmont, MA); Moses Moustakim (Cambridge, MA); Morgan Welzel O'Shea (Waltham, MA); Gesine Kerstin Veits (Somerville, MA); Jeremy L. Yap (Sudbury, MA); Robert T. Yu (Arlington, MA); Cosimo Dolente (Allschwil, CH); David Stephen Hewings (Basel, CH); Daniel Hunziker (Mohlin, CH); Bernd Kuhn (Reinach, CH); Piergiorgio Francesco Tommaso Pettazzoni (Regensdorf, CH); Fabienne Ricklin (Hombourg, FR); Claus Riemer (Freiburg, DE); Juergen Wichmann (Steinen, DE)
Assignee: C4 Therapeutics, Inc.
C07D471/04C07D519/00
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 12,559,492
App. No.
18/084,380
Granted
Feb 24, 2026
Kind
B2
Abstract

Present invention provides compounds that cause specifically the degradation of BRAF. The present compounds are useful for the treatment of various cancers.

Claims (67)

1 . A compound of Formula I:

or a pharmaceutically acceptable salt thereof;

wherein

R 2 and R 3 are independently selected from H and C 1-6 -alkyl;

or R 2 and R 3 together form —CH 2 —;

X is selected from —CH 2 —, —NR 4 —, and —O—;

R 4 is selected from H and C 1-6 -alkyl;

A is selected from:

R e is independently selected from halogen, cyano, and C 1-6 -alkyl;

t is selected from 0, 1, and 2;

R f is independently selected from H, C 3-8 -cycloalkyl, and C 1-6 -alkyl;

B is absent or selected from:

R g is independently selected from halogen, hydroxy, and C 1-6 -alkyl;

R t is independently selected from H, C 3-8 -cycloalkyl, and C 1-6 -alkyl;

u is independently selected from 0, 1, and 2;

E is absent or selected from

R i is independently selected from halogen, hydroxy, C 3-8 -cycloalkyl, and C 1-6 -alkyl;

v is independently selected from 0, 1, and 2;

m and n are independently selected from 0, 1, 2, and 3;

R a , R b , R c and R d are independently selected from H and C 1-6 -alkyl;

A 4 is selected from a bond and —NR 101 —;

R 101 is selected from H and C 1-6 -alkyl;

w is selected from 0 and 1;

A 3 is selected from a bond, —O—, —NR 200 —, and

R 200 is selected from H and C 1-6 -alkyl;

C is selected from:

R m is independently selected from halogen, hydroxy, C 3-8 -cycloalkyl, and C 1-6 -alkyl;

y is independently selected from 0, 1, and 2;

D is selected from:

R p is independently selected from halogen, C 3-8 -cycloalkyl, halo-C 1-6 -alkyl, C 1-6 -alkyl, cyano, C 1-6 -alkyl sulfonyl, and C 3-8 -cycloalkylsulfonyl;

z is independently selected from 0, 1, and 2;

R 100 is selected from H, halogen, and C 1-6 -alkyl;

R 7 and R 8 are independently selected from H, C 1-6 -alkyl, and halogen;

A 1 is selected from —NR 5 — and —CHR 6 —;

R 5 is selected from H and C 1-6 -alkyl;

or R 1 and R 5 together with the nitrogen atom to which they are attached form a heterocycloalkyl optionally substituted by R 14 , R 15 and R 16 ;

R 6 is selected from H and C 1-6 -alkyl;

or R 1 and R 6 together with the carbon atom to which they are attached form a cycloalkyl optionally substituted by R 14 , R 15 and R 16 ;

R 14 , R 15 and R 16 are independently selected from C 1-6 -alkyl and halogen; and

R 1 is selected from C 1-6 -alkyl and C 3-8 -cycloalkyl.

2 . The compound of claim 1 , wherein R 2 and R 3 are H.

3 . The compound of claim 2 , wherein X is —NR 4 —.

4 . The compound of claim 3 , wherein A is

5 . The compound of claim 4 , wherein R e is halogen and t is 1.

6 . The compound of claim 3 , wherein B is

7 . The compound of claim 6 , wherein R g is hydroxy and u is 1.

8 . The compound of claim 3 , wherein E is absent.

9 . The compound of claim 3 , wherein v is 0 or 1.

10 . The compound of claim 1 , wherein m is 0 and n is 0.

11 . The compound of claim 3 , wherein R a and R b are H.

12 . The compound of claim 3 , wherein R c and R d are H.

13 . The compound of claim 3 , wherein C is

14 . The compound of claim 13 , wherein y is 0.

15 . The compound of claim 3 , wherein C is

16 . The compound of claim 15 , wherein R m is hydroxy.

17 . The compound of claim 3 , wherein D is

18 . The compound of claim 1 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

19 . The compound of claim 1 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

20 . The compound of claim 1 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

21 . The compound of claim 1 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

22 . The compound of claim 1 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

23 . A pharmaceutical composition comprising a compound of claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 24, 2025
From: NASVESCHUK, CHRISTOPHER G.; LIANG, YANKE; JACKSON, KATRINA L.; DUPLESSIS, MARTIN; FITZGERALD, MARK E.; GARZA, VICTORIA; O'SHEA, MORGAN WELZEL; VEITS, GESINE KERSTIN; MOUSTAKIM, MOSES; YAP, JEREMY L.; GOOD, ANDREW CHARLES; YU, ROBERT T.
To: C4 THERAPEUTICS, INC.
Reel/Frame 071821/0742 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 24, 2025
From: NASVESCHUK, CHRISTOPHER G.; LIANG, YANKE; JACKSON, KATRINA L.; DUPLESSIS, MARTIN; FITZGERALD, MARK E.; GARZA, VICTORIA; O'SHEA, MORGAN WELZEL; VEITS, GESINE KERSTIN; MOUSTAKIM, MOSES; YAP, JEREMY L.; GOOD, ANDREW CHARLES; YU, ROBERT T.
To: C4 THERAPEUTICS, INC.
Reel/Frame 071821/0789 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 24, 2025
From: DOLENTE, COSIMO; HEWINGS, DAVID STEPHEN; HUNZIKER, DANIEL; KUHN, BERND; RIEMER, CLAUS; PETTAZZONI, PIERGIORGIO FRANCESCO TOMMASO; RICKLIN, FABIENNE; WICHMANN, JUERGEN
To: F. HOFFMANN-LA ROCHE AG
Reel/Frame 071821/0815 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 24, 2025
From: F. HOFFMANN-LA ROCHE AG
To: HOFFMANN-LA ROCHE INC.
Reel/Frame 071821/0846 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 24, 2025
From: HOFFMANN-LA ROCHE INC.
To: C4 THERAPEUTICS, INC.
Reel/Frame 071821/0887 →
Continuity (4)
Continuation PCTEP2021066524 · Jun 18, 2021
Provisional Application 63136574 · Jan 12, 2021
Provisional Application 63041335 · Jun 19, 2020
Related Publication 20230145336A1 · May 11, 2023
References Cited (116)
US 6306663B1 · Kenten et al. · 2001 [cited by applicant]
US 9750816B2 · Bradner et al. · 2017 [cited by applicant]
US 9821068B2 · Bradner et al. · 2017 [cited by applicant]
US 10646575B2 · Phillips et al. · 2020 [cited by applicant]
US 10660968B2 · Phillips et al. · 2020 [cited by applicant]
US 10723717B2 · Crew et al. · 2020 [cited by applicant]
US 10849982B2 · Phillips et al. · 2020 [cited by applicant]
US 10899768B2 · Bradner et al. · 2021 [cited by applicant]
US 10905768B1 · Phillips et al. · 2021 [cited by applicant]
US 11173211B2 · Crew et al. · 2021 [cited by applicant]
US 11185592B2 · Phillips et al. · 2021 [cited by applicant]
US 11220515B2 · Crews et al. · 2022 [cited by applicant]
US 11254672B2 · Norcross et al. · 2022 [cited by applicant]
US 11401256B2 · Norcross et al. · 2022 [cited by applicant]
US 11407732B1 · Henderson et al. · 2022 [cited by applicant]
US 11459335B2 · Phillips et al. · 2022 [cited by applicant]
US 11578075B2 · Bradner et al. · 2023 [cited by applicant]
US 11584748B2 · Nasveschuk et al. · 2023 [cited by applicant]
US 11623929B2 · Nasveschuk et al. · 2023 [cited by applicant]
US 11623932B2 · Mainolfi et al. · 2023 [cited by applicant]
US 20190233433A1 · Crews et al. · 2019 [cited by applicant]
US 20200207733A1 · Norcross et al. · 2020 [cited by applicant]
US 20200207783A1 · Norcross et al. · 2020 [cited by applicant]
US 20210009559A1 · Henderson et al. · 2021 [cited by applicant]
US 20210198256A1 · Nasveschuk et al. · 2021 [cited by applicant]
US 20220098194A1 · Nasveschuk et al. · 2022 [cited by applicant]
US 20220251061A1 · Phillips et al. · 2022 [cited by applicant]
US 20220289738A1 · Norcross et al. · 2022 [cited by applicant]
US 20220313826A1 · Phillips et al. · 2022 [cited by applicant]
US 20220313827A1 · Phillips et al. · 2022 [cited by applicant]
US 20220372016A1 · Phillips et al. · 2022 [cited by applicant]
US 20230014124A1 · Phillips et al. · 2023 [cited by applicant]
US 20230019060A1 · Nasveschuk et al. · 2023 [cited by applicant]
US 20230060334A1 · Nasveschuk et al. · 2023 [cited by applicant]
US 20230082430A1 · Henderson et al. · 2023 [cited by applicant]
US 20230095223A1 · Phillips et al. · 2023 [cited by applicant]
US 20230110648A1 · Nasveschuk et al. · 2023 [cited by applicant]
WO WO2007002325A1 · 2007 [cited by applicant]
WO WO2007002433A1 · 2007 [cited by applicant]
WO WO2008079903A1 · 2008 [cited by applicant]
WO WO2008079906A1 · 2008 [cited by applicant]
WO WO2010104945A1 · 2010 [cited by applicant]
WO WO2010104973A1 · 2010 [cited by applicant]
WO WO2010129567A1 · 2010 [cited by applicant]
WO WO2010129570A1 · 2010 [cited by applicant]
WO WO2011079133A2 · 2011 [cited by applicant]
WO WO2012109075A1 · 2012 [cited by applicant]
WO WO2012118492A1 · 2012 [cited by applicant]
WO WO2012138809A1 · 2012 [cited by applicant]
WO WO2014194127A1 · 2014 [cited by applicant]
WO WO2015150472A2 · 2015 [cited by applicant]
WO WO2015160845A2 · 2015 [cited by applicant]
WO WO2016083956A1 · 2016 [cited by applicant]
WO WO2016149668A1 · 2016 [cited by applicant]
WO WO2016191296A1 · 2016 [cited by applicant]
WO WO2016191303A1 · 2016 [cited by applicant]
WO WO2016197032A1 · 2016 [cited by applicant]
WO WO2016197114A1 · 2016 [cited by applicant]
WO WO2017007612A1 · 2017 [cited by applicant]
WO WO2017024317A2 · 2017 [cited by applicant]
WO WO2017024319A1 · 2017 [cited by applicant]
WO WO2017066193A1 · 2017 [cited by applicant]
WO WO2017197046A1 · 2017 [cited by applicant]
WO WO2018053354A1 · 2018 [cited by applicant]
WO WO2018071606A1 · 2018 [cited by applicant]
WO WO2018098280A1 · 2018 [cited by applicant]
WO WO2018102067A2 · 2018 [cited by applicant]
WO WO2018102725A1 · 2018 [cited by applicant]
WO WO2018118598A1 · 2018 [cited by applicant]
WO WO2018119357A1 · 2018 [cited by applicant]
WO WO2018119441A1 · 2018 [cited by applicant]
WO WO2018119448A1 · 2018 [cited by applicant]
WO WO2018134254A1 · 2018 [cited by applicant]
WO WO2018140809A1 · 2018 [cited by applicant]
WO WO2018144649A1 · 2018 [cited by applicant]
WO WO2018148443A1 · 2018 [cited by applicant]
WO WO2019060742A1 · 2019 [cited by applicant]
WO WO2019084462A1 · 2019 [cited by applicant]
WO WO2019140380A1 · 2019 [cited by applicant]
WO WO2019148055A1 · 2019 [cited by applicant]
WO WO2019199816A1 · 2019 [cited by applicant]
WO WO2020016243A1 · 2020 [cited by applicant]
WO WO2020051564A1 · 2020 [cited by examiner]
WO WO2020176983A1 · 2020 [cited by applicant]
WO WO2021011634A1 · 2021 [cited by applicant]
WO WO2022047145A1 · 2022 [cited by applicant]
Bartlett, et al. “The evolution of thalidomide and its IMiD derivatives as anticancer agents,” Nat Rev Cancer, 4(4):314-322, Apr. 1, 2004. [cited by applicant]
Berndsen et al. “New insights into ubiquitin E3 ligase mechanism,” Nat. Struct. Mol. Biol. Nature America, Inc. 21:4, 301-307, Apr. 4, 2014. [cited by applicant]
Bondeson et al. “Catalytic in vivo protein knockdown by small-molecule PROTACs” Nature Chemical Biology, 11:611-617, Jun. 10, 2015. [cited by applicant]
C4 Therapeutics Presentation Phillips—“Small Molecule Driven Targeted Protein Degradation”, ChemBio in the Hub 47, Cambridge, MA, 47 pages, Oct. 22, 2018. [cited by applicant]
C4 Therapeutics Presentation Fisher—“Targeted Protein Degradation”, Targeted Protein Degradation Summit, Boston, MA, 39 pages, Oct. 24-25, 2018. [cited by applicant]
C4 Therapeutics Presentation Fisher—“Degrader Drugs: From cellular activity to in vivo pharmacology Discovery on Target,” Boston, MA, 21 pages, Sep. 18, 2019. [cited by applicant]
C4 Therapeutics Presentation Nasveschuk—“Degrader Drug Space: What Rules?” HT-ADME Conference Cambridge, MA, 20 pages, Jun. 20, 2019. [cited by applicant]
Chamberlain et al. “Structure of the human cereblon-DDB1-lenalidomide complex reveals basis for responsiveness to thalidomide analogs” Nature Structural and Molecule Biology, Nature American, Inc., 21(9):803-809, Aug. 1… [cited by applicant]
Chao Zhang et al. “RAF inhibitors that evade paradoxical MAPK pathway activation” Nature, vol. 526, pp. 583-586, Oct. 14, 2015. [cited by applicant]
Corson et al. “Design and applications of bifunctional small molecules: Why two heads are better than one” ACS Chemical Biology 3(11), 677-692, Oct. 24, 2008. [cited by applicant]
Fischer et al. “Structure of the DDB1-CRBN E3 ubiquitin ligase in complex with thalidomide” Nature, Macmillan Publisher Limited, 512:49-53, Jul. 16, 2014. [cited by applicant]
Fischer et al. “The Molecular Basis of CRL4 [cited by applicant]
International Search Report and Written Opinion for PCT/EP2021/066524 dated, 10 pages, Jul. 7, 2021. [cited by applicant]
Ross A. Okimoto et al. “Preclinical efficacy of a RAF inhibitor that evades paradoxical MAPK pathway activation in protein kinase BRAF-mutant lung cancer” Proceedings of the National Academy of Sciences of the United St… [cited by applicant]
Nobumichi Ohoka et al. “Development of a potent small-molecule degrader against oncogenic BRAF [cited by applicant]
C. S. A. Tutuka et al. “PLX8394, a new generation BRAF inhibitor, selectively inhibits BRAF in colonic adenocarcinoma cells and prevents paradoxical MAPK pathway activation” Molecular Cancer, 16:112, Jun. 28, 2017. [cited by applicant]
Xiao-Ran, Han et al. “Discovery of selective small molecule degraders of BRAF-V600E,” Journal of Medicinal Chemistry, vol. 63, No. 8, 23, pp. 4069-4080, Mar. 30, 2020. [cited by applicant]
Zhan Yao et al. “RAF inhibitor PLX8394 selectively disrupts BRAF dimers and RAS-independent BRAF-mutant-driven signaling” Nat. Med. 25, 284-291, DOI: 10.1038/s41591-018-0274-5, Dec. 17, 2018. [cited by applicant]
U.S. Appl. No. 18/100,992, Nasveschuk et al., filed Jan. 24, 2023. [cited by applicant]
U.S. Appl. No. 18/105,735, Henderson et al., filed Feb. 3, 2023. [cited by applicant]
U.S. Appl. No. 18/106,893, Proia et al., filed Feb. 7, 2023. [cited by applicant]
U.S. Appl. No. 18/117,978, Nasveschuk et al., filed Mar. 6, 2023. [cited by applicant]
U.S. Appl. No. 18/134,971, Nasveschuk et al., filed Apr. 14, 2023. [cited by applicant]
U.S. Appl. No. 18/134,985, Nasveschuk et al., filed Apr. 14, 2023. [cited by applicant]
U.S. Appl. No. 18/134,990, Nasveschuk et al., filed Apr. 14, 2023. [cited by applicant]
U.S. Appl. No. 18/144,800, Nasveschuk et al., filed May 8, 2023. [cited by applicant]
U.S. Appl. No. 17/878,753, Norcross et al., filed Aug. 1, 2022. [cited by applicant]
U.S. Appl. No. 17/959,144, Phillips et al., filed Oct. 3, 2022. [cited by applicant]
U.S. Appl. No. 17/965,569, Nasveschuk et al., filed Oct. 13, 2022. [cited by applicant]
U.S. Appl. No. 18/079,815, Phillips et al., filed Dec. 12, 2022. [cited by applicant]