IP Library Granted Patent US 12668599
Granted Patent B2
US 12668599 · App. 18/920,528 · Granted Jun 30, 2026

Heterobifunctional compounds and methods of treating disease

Inventors: Kyle J. Eastman (Killingworth, CT); Katherine J. Kayser-Bricker (Branford, CT); James John Mousseau (Salem, CT); Kanak Shail Raina (Branford, CT)
Assignee: Halda Therapeutics OpCo, Inc.
C07D495/14A61K31/551A61P35/00C07D519/00
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Quick Facts
Patent No.
US 12668599
App. No.
18/920,528
Granted
Jun 30, 2026
Kind
B2
Abstract

The invention provides heterobifunctional compounds, pharmaceutical compositions, and their use treating disease, such as cancer.

Claims (37)

1 . A compound represented by Formula It or Iv, or a pharmaceutically acceptable salt thereof:

wherein

L is one of the following:

(i)-(7-11 membered spirocyclic or fused bicyclic saturated heterocyclic ring containing 1, 2, or 3 heteroatoms independently selected from nitrogen and oxygen)-O-***, wherein *** is the point of attachment to the phenylene group in said formula;

(ii) a 7-11 membered spirocyclic or fused bicyclic saturated heterocyclic ring containing 1, 2, or 3 heteroatoms independently selected from nitrogen and oxygen; or

(iii)-(7-11 membered spirocyclic saturated heterocyclic ring containing 1 or 2 heteroatoms selected from nitrogen)-(C 2-4 alkynylene)-***, wherein *** is the point of attachment to the phenylene group in said formula; and

t is 0 or 1.

2 . The compound of claim 1 , wherein the compound is a compound of Formula It.

3 . The compound of claim 2 , wherein tis 0 .

4 . The compound of claim 3 , wherein L is a -(7-11 membered spirocyclic or fused bicyclic saturated heterocyclic ring containing 1, 2, or 3 heteroatoms independently selected from nitrogen and oxygen)-O-***, wherein * is the point of attachment to the phenylene group in said formula.

5 . The compound of claim 3 , wherein L is -(7-11 membered spirocyclic saturated heterocyclic ring containing 1 or 2 heteroatoms selected from nitrogen)-(C 2-4 alkynylene)-***, wherein *** is the point of attachment to the phenylene group in said formula.

6 . The compound of claim 1 , wherein the compound is represented by Formula Iab or a pharmaceutically acceptable salt thereof:

7 . The compound of claim 1 , wherein the compound is represented by Formula Iac or a pharmaceutically acceptable salt thereof:

8 . The compound of claim 1 , wherein the compound is

9 . A compound represented by:

or a pharmaceutically acceptable salt thereof.

10 . The compound of claim 9 , wherein the compound is

11 . A compound selected from the following or a pharmaceutically acceptable salt thereof:

12 . The compound of claim 11 , wherein the compound is

13 . The compound of claim 11 , wherein the compound is

14 . A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.

15 . A pharmaceutical composition comprising a compound of claim 7 and a pharmaceutically acceptable carrier.

16 . A pharmaceutical composition comprising a compound of claim 10 and a pharmaceutically acceptable carrier.

17 . A pharmaceutical composition comprising a compound of claim 13 and a pharmaceutically acceptable carrier.

18 . A method of treating cancer, comprising administering to a patient in need thereof a therapeutically effective amount of a compound of claim 1 to treat the cancer, wherein the cancer is prostate cancer or breast cancer.

19 . The method of claim 18 , wherein the compound is a compound of claim 10 .

20 . A method of treating cancer, comprising administering to a patient in need thereof a therapeutically effective amount of a compound of claim 13 to treat the cancer, wherein the cancer is prostate cancer, or breast cancer.

21 . A method of treating prostate cancer, comprising administering to a patient in need thereof a therapeutically effective amount of a compound of claim 1 to treat the prostate cancer.

22 . A method of treating prostate cancer, comprising administering to a patient in need thereof a therapeutically effective amount of a compound of claim 10 to treat the prostate cancer.

23 . The method of claim 22 , wherein the patient is a human.

24 . A method of treating prostate cancer, comprising administering to a patient in need thereof a therapeutically effective amount of a compound of claim 13 to treat the prostate cancer.

25 . A method of treating castrate resistant metastatic prostate cancer, comprising administering to a patient in need thereof a therapeutically effective amount of a compound of claim 1 to treat the castrate resistant metastatic prostate cancer.

26 . A method of treating castrate resistant metastatic prostate cancer, comprising administering to a patient in need thereof a therapeutically effective amount of a compound of claim 10 to treat the castrate resistant metastatic prostate cancer.

27 . The method of claim 26 , wherein the patient is a human.

28 . A method of causing death of a cancer cell, comprising contacting a cancer cell with an effective amount of a compound of claim 1 to cause death of the cancer cell, wherein the cancer cell is selected from a prostate cancer, or breast cancer cell.

29 . A method of causing death of a prostate cancer cell, comprising contacting a prostate cancer cell with an effective amount of a compound of claim 1 to cause death of the prostate cancer cell.

30 . A method of causing death of a prostate cancer cell, comprising contacting a prostate cancer cell with an effective amount of a compound of claim 10 to cause death of the prostate cancer cell.