IP Library › Granted Patent US 12,486,256
Granted Patent B2
US 12,486,256 · App. 18/215,530 · Granted Dec 2, 2025

Crystal forms of crenolanib and methods of use thereof

Inventor: Vinay Jain (Dallas, TX)
Assignee: Arog Pharmaceuticals, Inc.
C07D405/14C07B2200/13
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Quick Facts
Patent No.
US 12,486,256
App. No.
18/215,530
Granted
Dec 2, 2025
Kind
B2
Abstract

present invention relates to novel crystalline polymorphs of 1-[2-[5-[(3-Methyl-3-oxetanyl) methoxy]-1H-benzimidazol-1-yl]-8-quinolinyl]-4-piperidinamine monobenzenesulfonate, and to methods for their preparation. The invention further relates to pharmaceutical compositions containing one or more forms and optionally one or more suitable pharmaceutical carriers. The invention also relates to methods of using the crystalline polymorphs of the invention in the treatment of disease.

Claims (7)

1 . Crystalline Form III of 1-[2-[5-[(3-Methyl-3-oxetanyl) methoxy]-1H-benzimidazol-1-yl]-8-quinolinyl]-4-piperidinamine monobenzenesulfonate which is anhydrous and has a melting point onset of 251° C., wherein said crystalline form has a powder x-ray diffraction pattern comprising peaks at diffraction angles (2Θ±0.2) 15.8, 19.8, and 21.7.

2 . The crystalline form of claim 1 , wherein the powder x-ray diffraction pattern has peaks at diffraction angles (2Θ±0.2) 12.6, 15.8, 19.8, 20.5, and 21.7.

3 . The crystalline form of claim 1 , wherein the powder x-ray diffraction pattern has peaks at diffraction angles (2Θ±0.2) 10.1, 12.6, 15.8, 19.8, 20.5, 21.7, 23.2, and 26.7.

4 . The crystalline form of claim 1 , wherein the powder x-ray diffraction pattern has peaks at diffraction angles (2Θ±0.2) 2.1, 3.0, 6.3, 7.4, 7.9, 8.7, 10.1, 12.1, 12.6, 13.2, 13.4, 13.9, 14.9, 15.8, 16.3, 16.5, 16.7, 16.9, 17.3, 17.6, 18.5, 19.1, 19.3, 19.8, 20.5, 20.8, 20.9, 21.7, 22.0, 22.4, 22.8, 22.9, 23.2, 23.8, 24.3, 24.5, 25.1, 25.9, 26.1, 26.7, 27.0, 27.4, 27.6, 28.2, 28.9, 29.9, 30.1, 30.6, 31.0, 31.4, and 31.9.

5 . A pharmaceutical composition comprising a crystalline form of claim 1 , and a pharmaceutically acceptable carrier.

6 . A method of treating a FLT3 mediated proliferative disorder, comprising administering to a subject in need thereof a therapeutically effective amount of the crystalline form of claim 1 , wherein the FLT3 mediated proliferative disorder is selected from the group consisting of Hodgkin's disease, myeloma, acute lymphocytic leukemia (ALL), acute myeloid leukemia (AML), acute promyelocytic leukemia (APL), chronic lymphocytic leukemia (CLL), chronic myeloid leukemia (CML), chronic neutrophilic leukemia (CNL), acute undifferentiated leukemia (AUL), anaplastic large-cell lymphoma (ALCL), prolymphocytic leukemia (PML), juvenile myelomonocytic leukemia (JMML), adult T-cell ALL, AML with trilineage myelodysplasia (AMLITMDS), mixed lineage leukemia (MLL), myelodysplastic syndromes (MDS), myeloproliferative disorders (MPD), multiple myeloma, biliary tract cancer, bladder cancer, breast cancer, cervical cancer, CNS cancer, colon cancer, colorectal carcinoma, esophageal cancer, gastric cancer, gastroesophageal junction (GEJ) adenocarcinoma, gastric adenocarcinoma, stage IIIB gastric adenocarcinoma, stage IV invasive gastric adenocarcinoma, metastatic esophageal adenocarcinoma, glioblastoma, head and neck cancer, hepatocellular carcinoma, liver cancer, lung cancer, melanoma, non-small cell cancer, nasopharyngeal cancer, neuroendocrine cancer, ovarian cancer, pancreatic cancer, prostate cancer, renal cancer, salivary gland cancer, small cell cancer lung cancer, squamous cell cancer, skin cancer, stomach cancer, testicular cancer, thyroid cancer, thymoma, and uterine cancer.

7 . A process for the preparation of the crystalline form of claim 1 , comprising suspending 1-[2-[5-[(3-Methyl-3-oxetanyl) methoxy]-1H-benzimidazol-1-yl]-8-quinolinyl]-4-piperidinamine monobenzenesulfonate in 99% ethanol/1% toluene (% v/v); and then shaking until precipitation.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2023
From: JAIN, VINAY
To: AROG PHARMACEUTICALS, INC.
Reel/Frame 065519/0137 →
Continuity (3)
Division 17326433 · May 21, 2021
Provisional Application 63053921 · Jul 20, 2020
Related Publication 20230339918A1 · Oct 26, 2023
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