Solid forms, pharmaceutical compositions and preparation of heteroaromatic macrocyclic ether compounds
Inventors
Chen, Sibao • COOPER, Christopher G. F. • Gerard, Baudouin • Horan, Joshua Courtney • KROPP, Jason T. • LANE, Benjamin Stephen • Pearson, David James
Assignees
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Publication Number
US-12043626-B2
Publication Date
2024-07-23
Expiration Date
Abstract
Provided herein are solid forms comprising a compound of formula (I), or a stereoisomer, or a mixture of stereoisomers thereof, or a pharmaceutically acceptable salt thereof. Also provided herein are methods of synthesizing a compound of formula (I), pharmaceutical compositions comprising the same, and methods of treating, preventing, and managing various disorders using the compositions provided herein.
Core Innovation
The disclosure relates to preparation and characterization of solid forms comprising a compound of Formula (I) (Compound 1) and/or a pharmaceutically acceptable salt thereof. The solid forms include free base and pharmaceutically acceptable salt forms, including crystalline and amorphous forms, distinguished and identified using XRPD powder diffraction patterns measured with Cu Kα radiation.
The solid forms are described as crystalline solid forms of a compound of Formula (I), including Form 1 through Form 7, and as conversion among specific solid forms by crystallization, recrystallization, or solvent-mediated conversion of non-Form solids to target crystalline forms. The document also describes conversion to Forms 2 through 7, conversion from Form 1 through 6 to Form 7, and solvent and anti-solvent systems for obtaining crystalline solid forms.
In addition to free bases, the disclosure provides solid-form salt preparations for besylate and phosphate salts of Compound 1. It describes forming besylate and phosphate solid forms by exposure of Compound 1 to benzenesulfonic acid or phosphoric acid, optionally followed by crystallization and recrystallization, and characterizes the resulting solid forms using XRPD and thermal and vapor sorption signatures.
The patent further describes pharmaceutical compositions comprising the solid form and pharmaceutically acceptable excipients, including unit-dose tablet and granular formulation contexts, and states cancer treatment by administering such pharmaceutical compositions.
Claims Coverage
The independent claims center on solid forms of the compound of Formula (I) as a free base or specified pharmaceutically acceptable salts, each defined by XRPD patterns measured with Cu Kα radiation. The merged claim coverage includes free base, besylate, phosphate, and pharmaceutical composition features.
Xrpd-defined solid forms of free base
A solid form comprising a free base of a compound of Formula (I), characterized by an XRPD pattern measured using Cu Kα radiation comprising multiple alternative peak sets reported in the input.
Xrpd-defined solid form of besylate salt
A solid form comprising a besylate salt of a compound of Formula (I), characterized by an XRPD pattern measured using Cu Kα radiation comprising specified peaks at defined 2θ values.
Xrpd-defined solid form of phosphate salt
A solid form comprising a phosphate salt of a compound of Formula (I), characterized by an XRPD pattern measured using Cu Kα radiation comprising specified peaks at defined 2θ values.
Pharmaceutical composition comprising the solid form and an excipient
A pharmaceutical composition comprises the solid form and a pharmaceutically acceptable excipient.
Overall, the claim coverage is directed to solid forms of Formula (I) distinguished by XRPD peak patterns for free base, besylate, and phosphate forms, with pharmaceutical compositions including excipients.
Stated Advantages
Not explicitly described in patent.
Documented Applications
Cancer treatment by administering pharmaceutical compositions comprising the solid form and pharmaceutically acceptable excipients.
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