Solid forms of (1r,4r)-6′-fluoro-N,N-dimethy1-4-phenyl-4′,9′-dihydro-3′ H-spiro-[cyclohexane-1,1′-pyrano-[3,4,b]indol]-4-amine hydrochloride

#The invention relates to solid forms of (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine hydrochloride, in particular crystalline forms and/or amorphous forms thereof, pharmaceutical compositions and medicaments comprising these solid forms, the use of these solid forms as well as to a process for obtaining them.

#Pharmaceutically active drugs can exist in different solid forms. For example, a drug may exist in different crystalline forms which have different physical and chemical properties.

#Different physical properties can cause different crystalline forms of the same drug to have largely different processing and storage performance. Such physical properties include, for example, thermodynamic stability, crystal morphology [form, shape, structure, particle size, particle size distribution, degree of crystallinity, color], ripple behavior, flowability, density, bulk density, powder density, apparent density, vibrated density, depletability, emptyability, hardness, deformability, grindability, compressability, compactability, brittleness, elasticity, caloric properties [particularly melting point], solubility [particularly equilibrium solubility, pH dependence of solubility], dissolution [particularly dissolution rate, intrinsic dissolution rate], reconstitutability, hygroscopicity, tackiness, adhesiveness, tendency to electrostatic charging, and the like.

#FIGS. 1a-g show the PXRD patterns of crystalline forms A, B, C, D, E, F and G.

#FIGS. 2a-g show the Raman spectra of crystalline forms A, B, C, D, E, F and G.

#The compound according to general formula (I) can systematically be referred to as “1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole (trans)” or as “(1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine”, respectively.

#In the solid form according to the invention the compound according to general formula (I) is present in form of the hydrochloride. The definition of the hydrochloride of the compound according to general formula (I) as used herein includes salts, solvates, co-crystals, polymorphs, amorphous forms and multi-component complex forms. For the purpose of the specification, “hydrochloride” preferably means that the compound according to general formula (I) is present in form of the hydrochloric acid-addition salt. The most basic functional group of the compound according to general formula (I) is its N,N-dimethylamino moiety, which thus according to the invention is preferably protonated. Methods to determine whether a chemical substance is present as a salt, co-crystalline form, crystalline form or as the free base, optionally in each case in a solvated from thereof, are known to the skilled artisan such as 14N or 15N solid state NMR, X-ray diffraction, IR, DSC, TGA, Raman and XPS. 1H-NMR recorded in solution may also be used to consider the presence of protonation.

#Unless explicitly stated otherwise, all 2Θ values refer to a X-ray diffractogram measured using CuKα radiation having a wavelength of 1.54060 Å determined at 23+/−3° C.