IP Library › Granted Patent US 12,521,386
Granted Patent B2
US 12,521,386 · App. 17/413,139 · Granted Jan 13, 2026

Small molecule inhibitors of the androgen receptor activity and/or expression and uses thereof

Inventors: Christopher Hulme (Tucson, AZ); Yeng-Jeng Shaw (Tucson, AZ); Vijay Gokhale (Tucson, AZ)
Assignee: Arizona Board of Regents on Behalf of the University of Arizona
A61K31/496A61K31/454A61K45/06C07D213/74C07D257/04C07D401/12C07D401/14C07D405/12C07D405/14C07D409/14C07D413/14
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Quick Facts
Patent No.
US 12,521,386
App. No.
17/413,139
Granted
Jan 13, 2026
Kind
B2
Abstract

This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a piperazine (or similar) structure which function as antagonists of androgen receptor activity, and their use as therapeutics for the treatment of cancer (e.g., castration-resistant prostate cancer) and other conditions characterized with androgen receptor activity and/or androgen receptor expression.

Claims (13)

1 . A compound described by Formula I:

including pharmaceutically acceptable salts, solvates, and/or prodrugs thereof;

wherein X is Nitrogen rendering the resulting compound encompassed within Formula II:

or wherein X is C—H rendering the resulting compound encompassed within Formula III:

wherein R1 is selected from

wherein R2 is selected from hydrogen, methyl,

wherein R3 is selected from hydrogen, methyl,

and

wherein R4 is selected from hydrogen and methyl.

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

or a pharmaceutically acceptable salt, solvate, or prodrug thereof, and a pharmaceutically acceptable carrier.

3 . The compound of claim 1 , wherein the compound is comprised within a pharmaceutical composition.

4 . A kit comprising a compound of claim 1 , and instructions for administering said compound to a patient.

Assignments (2)
CONFIRMATORY LICENSE Recorded Dec 6, 2023
From: UNIVERSITY OF ARIZONA
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 065790/0690 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 10, 2022
From: HULME, CHRISTOPHER; SHAW, YENG-JENG; GOKHALE, VIJAY
To: ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA
Reel/Frame 060160/0635 →
Continuity (2)
Provisional Application 62778139 · Dec 11, 2018
Related Publication 20220062278A1 · Mar 3, 2022
References Cited (17)
US 3989816A · Rajadhyaksha · 1976 [cited by applicant]
US 4444762A · Rajadhyaksha · 1984 [cited by applicant]
US 5770581A · Weichselbaum et al. · 1998 [cited by applicant]
US 20040009969A1 · Cleve et al. · 2004 [cited by applicant]
US 20070249564A1 · Erion et al. · 2007 [cited by applicant]
US 20100016279A1 · Bradbury · 2010 [cited by examiner]
US 20140350015A1 · Mcdonald et al. · 2014 [cited by applicant]
WO WO2017165822 · 2017 [cited by applicant]
WO WO2017165822A1 · 2017 [cited by examiner]
Mak et al., Artificial intelligence in drug development: present status and future prospects, Drug Discovery Today; Drug Discovery Today vol. 24, No. 3, Mar. 2019 (pp. 773-780) (Year: 2019). [cited by examiner]
D. Taylor, in Pharmaceuticals in the Environment, ed. R. E. Hester and R. M. Harrison, The Royal Society of Chemistry, 2015, pp. 1-33. Doi: https://doi.org/10.1039/9781782622345-00001 (Year: 2015). [cited by examiner]
Kranz M, et al., “Bridging from Brain to Tumor Imaging: (S)-(-)- and (R)-(+)-[18F]Fluspidine for Investigation of Sigma-1 Receptors in Tumor-Bearing Mice”, Molecules. Mar. 20, 2018;23(3). [cited by applicant]
Sadeghzadeh M, et al., “Radioiodination and preclinical evaluation of 4-benzyl-1-(3-[125l]-iodobenzylsulfonyl)piperidine as a breast tumor imaging tracer in mouse”, Ann Nucl Med. May 2017;31(4):335-346. [cited by applicant]
Baum E, et al., “PET Imaging Evaluation of Four s1 Radiotracers in Nonhuman Primates”, J Nucl Med. Jun. 2017;58(6):982-988. [cited by applicant]
Yang D, et al., “Design and Investigation of a [18F]-labeled Benzamide Derivative as a High Affinity Dual Sigma Receptor Subtype Radioligand for Prostate Tumor Imaging”, Mol Pharm. Mar. 6, 2017;14(3):770-780. [cited by applicant]
International Search Report and Written Opinion of PCT/US19/65751; mailed Dec. 11, 2019; 9 pages. [cited by applicant]
“1-[(1-Tert-butyltetrazol-5-yl)methyl]-4-(4-methoxyphenyl)piperazine”, Pubchem CID 1436459, 2005, pp. 2, 7. [cited by applicant]