IP Library Granted Patent US 12,018,045
Granted Patent B2
US 12,018,045 · App. 16/978,442 · Granted Jun 25, 2024

17-beta-hydroxywithanolides and use thereof in treating cancer

Inventors: Thomas J. Sayers (Boonsboro, MD); Poonam Tewary (Frederick, MD); Leslie Gunatilaka (Tucson, AZ); Alan D. Brooks (Frederick, MD); Kithsiri Wijeratne (Tucson, AZ); Yaming Xu (Tucson, AZ)
Assignees: The United States of America, as represented by the Secretary, Department of Health and Human Services; Arizona Board of Regents on Behalf of the University of Arizona
C07J71/001A61K45/06
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Quick Facts
Patent No.
US 12,018,045
App. No.
16/978,442
Granted
Jun 25, 2024
Kind
B2
Abstract

Disclosed are compounds suitable for enhancing cancer treatment, for example, a compound of formula (I): (I) wherein R 1 is as defined herein. Also disclosed is a method of enhancing the response of cancer cells in a mammal to treatment with an apoptosis inducing ligand, a method of inducing apoptosis in cancer cells in a mammal, and a method of treating prostate cancer in mammal in need thereof comprising administration of a compound described herein.

Claims (14)

1. A compound of formula (I):

wherein R 1 is C 3 -C 10 alkyl, C 3 -C 8 cycloalkyl, C 6 -C 10 aryl, C 6 -C 10 aryl-C 1 -C 10 alkyl, C 6 -C 10 aryl-C 2 -C 10 alkenyl, monocyclic heteroaryl, bicyclic heteroaryl, monocyclic heteroaryl-C 1 -C 10 alkyl, bicyclic heteroaryl-C 1 -C 10 alkyl, or 4-alkylenyl-tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one,

wherein the aryl or heteroaryl portion of R 1 is optionally substituted with one or more substituents selected from the group consisting of alkyl, alkoxy, aryl, thioalkoxy, heterocyclyl, and nitro.

2. The compound of claim 1 , wherein R 1 is C 3 -C 8 cycloalkyl, C 6 -C 10 aryl, C 6 -C 10 aryl-C 1 -C 10 alkyl, C 6 -C 10 aryl-C 2 -C 10 alkenyl, monocyclic heteroaryl, bicyclic heteroaryl, monocyclic heteroaryl-C 1 -C 10 alkyl, bicyclic heteroaryl-C 1 -C 10 alkyl, or 4-alkylenyl-tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one,

wherein the aryl or heteroaryl portion of R 1 is optionally substituted with one or more substituents selected from the group consisting of alkyl, alkoxy, aryl, thioalkoxy, heterocyclyl, and nitro.

3. The compound of claim 2 , wherein R 1 is

4. The compound of claim 2 ,

wherein R 1 is

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

6. A pharmaceutical composition comprising a compound of claim 2 and a pharmaceutically acceptable carrier.

7. A pharmaceutical composition comprising a compound of claim 3 and a pharmaceutically acceptable carrier.

8. A pharmaceutical composition comprising a compound of claim 4 and a pharmaceutically acceptable carrier.

9. The compound of claim 2 , which is selected from the group consisting of

10. A pharmaceutical composition comprising a compound of claim 9 and a pharmaceutically acceptable carrier.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 15, 2021
From: GUNATILAKA, LESLIE; XU, YAMING; WIJERATNE, KITHSIRI
To: ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA
Reel/Frame 058110/0617 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2021
From: SAYERS, THOMAS JOSEPH; BROOKS, ALAN DAVID; TEWARY, POONAM
To: THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES
Reel/Frame 056153/0927 →
CONFIRMATORY LICENSE Recorded Sep 9, 2020
From: UNIVERSITY OF ARIZONA
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 053730/0401 →
Continuity (2)
Provisional Application 62639337 · Mar 6, 2018
Related Publication 20210047363A1 · Feb 18, 2021