IP Library Granted Patent US 12,077,554
Granted Patent B2
US 12,077,554 · App. 18/054,435 · Granted Sep 3, 2024

CDK9 inhibitors and polymorphs thereof for use as agents for treatment of cancer

Inventors: Adam Siddiqui-Jain (South Jordan, UT); Paul Flynn (Citrus Heights, CA); Yuji Fujiwara (Draper, UT); Shuji Masumoto (Toyonaka, JP); Hiroaki Tanaka (Toyonaka, JP); Hirotaka Kurebayashi (Minoh, JP); Takahiko Hashizuka (Matsubara, JP); Yuka Arikawa (Minoh, JP)
Assignee: Sumitomo Pharma Oncology, Inc.
C07F9/65586A61K9/0053A61P35/00C07B2200/13
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Quick Facts
Patent No.
US 12,077,554
App. No.
18/054,435
Granted
Sep 3, 2024
Kind
B2
Abstract

A crystalline form and/or polymorph of a compound having the following structure (I), including tautomeric and zwitterionic forms thereof, are provided: Methods associated with preparation and use of the polymorphs, and pharmaceutical compositions comprising the same are also provided. Also provided are methods for preparing a compound having formula (I), or a salt, tautomer or zwitterionic form thereof.

Claims (22)

1. A method for treating a cancer in a mammal in need thereof, comprising administering to the mammal crystalline Form B of a compound having the following structure (I):

or a zwitterionic form thereof, in an amount of from about 1 mg to about 50 mg per day, wherein crystalline Form B is characterized by an x-ray powder diffraction pattern comprising at least three peaks at 2-theta angles selected from the group consisting of 4.8±0.2°, 10.8±0.2°, 13.7±0.2°, 14.9±0.2°, 20.0±0.2° and 24.6±0.2°.

2. The method of claim 1 , wherein crystalline Form B is characterized by an x-ray powder diffraction pattern comprising peaks at the following 2-theta angles: 10.8±0.2°, 14.9±0.2° and 20.0±0.2°.

3. The method of claim 1 , wherein crystalline Form B has an x-ray powder diffraction pattern substantially in accordance with that depicted in FIG. 1 .

4. The method of claim 1 , wherein crystalline Form B is a compound having structure (II):

5. The method of claim 1 , wherein about 32 mg per day of crystalline Form B of a compound having structure (I), or a zwitterionic form thereof, is administered to the mammal.

6. The method of claim 1 , wherein crystalline Form B of a compound having structure (I), or a zwitterionic form thereof, is administered to the mammal once per day.

7. The method of claim 1 , wherein crystalline Form B of a compound having structure (I), or a zwitterionic form thereof, is administered to the mammal twice per day.

8. The method of claim 1 , wherein crystalline Form B of a compound having structure (I), or a zwitterionic form thereof, is administered to the mammal daily.

9. The method of claim 1 , wherein the cancer comprises a solid tumor.

10. The method of claim 1 , wherein the cancer is prostate cancer.

11. The method of claim 1 , wherein the cancer is a sarcoma.

12. The method of claim 11 , wherein the sarcoma is Kaposi sarcoma, Ewing sarcoma, osteosarcoma, rhabdomyosarcoma, soft tissue sarcoma or uterine sarcoma.

13. The method of claim 1 , wherein the cancer is a sarcoma, bladder cancer or renal cancer.

14. The method of claim 1 , wherein the cancer is a renal cell carcinoma.

15. The method of claim 1 , wherein the cancer is a hematologic cancer.

16. The method of claim 15 , wherein the hematologic cancer is selected from acute myelogenous leukemia (AML), follicular lymphoma, acute lymphoblastic leukemia (ALL), chronic lymphocytic leukemia (CLL), multiple myeloma (MM) or non-Hodgkin's lymphoma.

17. The method of claim 1 , wherein crystalline Form B of a compound having structure (I), or a zwitterionic form thereof, is administered to the mammal continuously.

18. The method of claim 1 , wherein crystalline Form B of a compound having structure (I), or a zwitterionic form thereof, is administered to the mammal once or twice daily for the first 21 days out of a 28-day cycle.

19. The method of claim 1 , wherein the cancer is MCL-1 dependent.

20. A method for treating a renal cancer in a mammal in need thereof, comprising administering to the mammal crystalline Form B of a compound having the following structure (I):

or a zwitterionic form thereof, in an amount of from about 1 mg to about 50 mg per day, wherein crystalline Form B is characterized by an x-ray powder diffraction pattern comprising at least three peaks at 2-theta angles selected from the group consisting of 4.8±0.2°, 10.8±0.2°, 13.7±0.2°, 14.9±0.2°, 20.0±0.2° and 24.6±0.2°.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2022
From: SIDDIQUI-JAIN, ADAM; FLYNN, PAUL; FUJIWARA, YUJI
To: TOLERO PHARMACEUTICALS, INC.
Reel/Frame 061954/0230 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2022
From: MASUMOTO, SHUJI; TANAKA, HIROAKI; KUREBAYASHI, HIROTAKA; HASHIZUKA, TAKAHIKO; ARIKAWA, YUKA
To: SUMITOMO DAINIPPON PHARMA COMPANY, LIMITED
Reel/Frame 061954/0350 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2022
From: SUMITOMO DAINIPPON PHARMA COMPANY, LIMITED
To: TOLERO PHARMACEUTICALS, INC.
Reel/Frame 061954/0448 →
MERGER Recorded Dec 2, 2022
From: TOLERO PHARMACEUTICALS, INC.
To: BOSTON BIOMEDICAL, INC.
Reel/Frame 061954/0493 →
CHANGE OF NAME Recorded Dec 2, 2022
From: BOSTON BIOMEDICAL, INC.
To: SUMITOMO DAINIPPON PHARMA ONCOLOGY, INC.
Reel/Frame 062050/0980 →
CHANGE OF NAME Recorded Dec 2, 2022
From: SUMITOMO DAINIPPON PHARMA ONCOLOGY, INC.
To: SUMITOMO PHARMA ONCOLOGY, INC.
Reel/Frame 062051/0070 →
Continuity (4)
Continuation 17225836 · Apr 8, 2021
Continuation 16703773 · Dec 4, 2019
Provisional Application 62775303 · Dec 4, 2018
Related Publication 20230250116A1 · Aug 10, 2023