Crystalline form of tegavivint, method of preparation, and use thereof
Inventors
Ostovic, Drazen • Sukumar, Gowri
Assignees
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Publication Number
US-12297185-B2
Publication Date
2025-05-13
Expiration Date
Abstract
The present invention relates to crystalline forms of (9E,10E)-2,7-bis((3,5-dimethylpiperidin-1-yl)sulfonyl)anthracene-9,10-dione dioxime, pharmaceutical compositions comprising the crystalline form, processes for preparing the crystalline form and methods of use therefore.
Core Innovation
The patent discloses a crystalline form of a compound having the specified formula, designated as Form IV. Form IV is characterized by an endotherm before decomposition as shown by differential scanning calorimetry (DSC), with the endotherm peak maximum at about 115.9 °C.
Form IV is further described with solid-state characterization features, including X-ray powder diffraction (XRPD) diffraction peaks defined by 2θ angle values of 5.0±0.2°, 7.5±0.2°, 7.7±0.2°, 14.8±0.2°, 15.2±0.2°, 15.4±0.2°, 20.0±0.2°, and 22.2±0.2°. The document also characterizes Form IV by thermogravimetric analysis (TGA) weight loss and dynamic vapor sorption (DVS) water uptake.
The document further identifies Form IV as a hydrate and links Form IV to a nanosuspension preparation context by conversion of Form IV to Form I during milling, thereby enabling stable single-polymorph nanosuspensions.
Claims Coverage
The independent claim covers one inventive feature: a specific crystalline polymorph designation, Form IV, of the specified compound, defined by DSC thermal behavior with an endotherm peak maximum before decomposition at about 115.9 °C. Dependent claims further refine Form IV using XRPD peak positions, TGA weight loss, DVS water uptake, and hydrate status, and connect Form IV-derived materials to pharmaceutical use for treating cancer and tumor metastasis, including acute myeloid leukemia (AML).
Form IV DSC endotherm peak before decomposition
The crystalline form is designated as Form IV and is characterized by having an endotherm before decomposition as shown by differential scanning calorimetry (DSC), wherein the endotherm has a peak maximum at about 115.9 °C.
Form IV XRPD diffraction peak pattern
The crystalline form has an x-ray powder diffraction (XRPD) pattern with diffraction peaks having 2θ angle values comprising 5.0±0.2°; 7.5±0.2°; 7.7±0.2°; 14.8±0.2°; 15.2±0.2°; 15.4±0.2°; 20.0±0.2°; and 22.2±0.2°.
Form IV TGA weight loss constraint
Form IV is further characterized by a weight loss of about 8.4% up to 150 °C as shown by thermogravimetric analysis (TGA).
Form IV DVS water uptake at specified humidity
Form IV is further characterized by a water uptake of about 9.1% at 25 °C and 80% relative humidity (RH) as shown by dynamic vapor sorption (DVS).
Form IV hydrate designation
The crystalline form is specified such that Form IV is a hydrate.
Overall, the claim set defines Form IV by a DSC endotherm before decomposition at about 115.9 °C and further characterizes it by XRPD peak positions, TGA weight loss, DVS water uptake, and hydrate status. The document also ties Form IV-derived nanosuspension and/or compositions to treating cancer and tumor metastasis, including AML.
Stated Advantages
Stable single-polymorph nanosuspensions.
Documented Applications
Formulations and methods for preventing or treating cancer or tumor metastasis, including acute myeloid leukemia (AML).
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