Solid forms of cannabidiol and uses thereof
Inventors
Emanuele, R. Martin • Shattock-Gordon, Tanise • Williford, Tabitha • Andres, Mark • Andres, Patricia
Assignees
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Publication Number
US-11364202-B2
Publication Date
2022-06-21
Expiration Date
Abstract
Disclosed herein are cocrystals of cannabidiol and a coformer containing 5-6 membered rings comprised of carbon and nitrogen atoms, wherein the 5-6 membered rings can be unsaturated or saturated and the rings contain 1 to 2 nitrogen atoms. Cocrystals of cannabidiol and a coformer selected from L-proline, D-proline, tetramethylpyrazine, and 4,4′-dipyridyl are also disclosed herein.
Core Innovation
The invention relates to solid forms of cannabidiol (CBD) in the form of cocrystals with the coformer tetramethylpyrazine. The solid forms are characterized by an x-ray diffraction pattern obtained using Cu Kα radiation, comprising one or more peaks at about 9.1, 14.6, 18.3, and 19.6 degrees 2θ.
The description also discloses additional CBD solid-form embodiments formed with specific coformers, including L-proline, D-proline, tetramethylpyrazine, and 4,4′-dipyridyl. These cocrystal solid-form embodiments are identified by diffraction peak sets and characterized using XRPD peak sets, DSC thermogram behavior, TGA mass-loss behavior, and FT-IR and NMR reference information.
A specific example described is that a CBD 4,4′-dipyridyl cocrystal “Material A” converts to a unique “Material B” after exposure to 95% RH at room temperature for 1 week. The invention further includes methods for treating a disease or condition in a subject by administering pharmaceutical compositions comprising these CBD solid forms.
Claims Coverage
The provided independent claims cover methods of treating a disease or condition in a subject by administering a pharmaceutical composition containing a CBD solid form, with the solid form defined by an XRPD peak set measured using Cu Kα radiation and, in one case, additional constraints on cocrystal stoichiometry (molar ratio about 1:1). Across the independent claims, there are 2 inventive features.
XRPD-defined solid form of cannabidiol with tetramethylpyrazine
Administering a pharmaceutical composition comprising a solid form of cannabidiol and the coformer tetramethylpyrazine, wherein the solid form has an x-ray diffraction pattern comprising one or more peaks at about 9.1, 14.6, 18.3, and 19.6 degrees 2θ ±10 as obtained using Cu Kα radiation.
About 1:1 cannabidiol–tetramethylpyrazine cocrystal defined by XRPD peaks
Administering a pharmaceutical composition comprising a cocrystal of cannabidiol and the coformer tetramethylpyrazine in a molar ratio of about 1:1, wherein the cocrystal has an x-ray diffraction pattern comprising one or more peaks at about 9.1, 14.6, 18.3, and 19.6 degrees 2θ ±0.2 as obtained using Cu Kα radiation.
Both independent claims require treatment by administering a pharmaceutical composition containing a CBD solid form/cocrystal with tetramethylpyrazine, where the solid form is defined by an XRPD peak pattern using Cu Kα radiation; the second independent claim additionally requires an about 1:1 molar ratio and a tighter peak tolerance (2θ ±0.2). Dependent claims further define selectable disease/condition sets and, in some cases, add excipients/carriers and additional solid-state characterization constraints.
Stated Advantages
Not explicitly described in patent.
Documented Applications
Not explicitly described in patent.
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