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Publication Number
US-11643401-B2
Publication Date
2023-05-09
Expiration Date
Abstract
The invention relates to crystalline forms of a 3-substituted 1,2,4-oxadiazole compound, including an anhydrous crystalline form, methods of their preparation, and related pharmaceutical preparations thereof. The invention also relates to preparations suitable for pharmaceutical, veterinary, and agriculturally-relevant uses.
Core Innovation
The invention relates to an anhydrous crystalline compound having the structure of formula (I), where the solid is defined by specific powder X-ray diffraction (XRPD) 2θ values. The document describes crystalline anhydrous forms, including anhydrous polymorphic forms, of a 3-substituted 1,2,4-oxadiazole immunomodulator. Form A is identified by XRPD with selected 2θ diffraction peaks as set out in the disclosure.
The document further characterizes the anhydrous crystalline form using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), dynamic vapor sorption (DVS), and single crystal X-ray diffraction. The disclosed thermal behavior and partial hygroscopicity are reported for the anhydrous crystalline form, and the material is also described as optionally non-solvated.
The disclosure also provides representative preparation approaches for obtaining the anhydrous form, including crystallization and isolation of crystals, with optional seeding using Form A seed crystals. In addition, the disclosure describes formulation use of the anhydrous crystalline compound as a pharmaceutical composition, including dosage forms such as tablets, capsules, and suspensions, for modulating immune responses.
The therapeutic use cases explicitly include cancer, immune/inflammatory disorders, infections, and transplant rejection. The document connects the immunomodulator solid form to pharmaceutical composition embodiments across these disease areas.
Claims Coverage
The independent claim is directed to an anhydrous crystalline compound of formula (I) defined by a specified set of XRPD 2θ values. Dependent claims refine the independent claim primarily by specifying quantitative purity levels and by including a pharmaceutical composition with pharmaceutically acceptable excipients.
Anhydrous crystalline compound of formula (I) defined by XRPD 2θ values
An anhydrous crystalline compound having the structure of formula (I) and 2θ values of 10.2±0.2, 15.2±0.2, 15.8±0.2, 16.5±0.2, 17.6±0.2, 18.1±0.2, 18.8±0.2, 20.5±0.2, 21.8±0.2, 22.3±0.2, 22.9±0.2, 24.2±0.2, 25.4±0.2, 26.1±0.2, 26.4±0.2, 27.5±0.2, 28.1±0.2, 28.8±0.2, 29.3±0.2, 30.4±0.2, 30.6±0.2, 32.0±0.2, 33.4±0.2, 33.6±0.2, 34.6±0.2, 35.8±0.2, 36.7±0.2, 37.3±0.2, 38.2±0.2, 38.6±0.2, and 39.2±0.2.
Crystalline compound with specified purity
The crystalline compound of the XRPD-defined anhydrous crystalline compound has a purity of about 90%, and also about 92%, about 97%, and about 98%, as specifically recited in dependent claims.
Pharmaceutical composition with pharmaceutically acceptable excipients
A pharmaceutical composition comprising the anhydrous crystalline compound defined by the XRPD 2θ values and one or more pharmaceutically acceptable excipients.
Across the independent claim and dependent refinements, the claim coverage is anchored on an anhydrous crystalline compound of formula (I) defined by a specified XRPD peak list, with further coverage through purity constraints and formulation into pharmaceutical compositions with pharmaceutically acceptable excipients.
Stated Advantages
Not explicitly described in patent.
Documented Applications
Treating/modulating immune responses for cancer.
Treating/modulating immune responses for immune/inflammatory disorders.
Treating/modulating immune responses for infections.
Treating/modulating immune responses for transplant rejection.
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