Solid forms of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4A,5,10,10A-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid
The present invention relates to new solid forms of the compound (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid with the formula (Id) below. The compound of formula (Id) is a prodrug of a catecholamine for use in treatment of neurodegenerative diseases and disorders such as Parkinson's Disease.
1. A solid form of the compound of formula (Id)
wherein said solid form is selected from:
the group consisting of the dihydrate of the zwitterion of compound (Id), the heptahydrate of the zwitterion of compound (Id) and the potassium salt of the compound (Id).
2. The solid form according to claim 1 , wherein said solid form is the dihydrate of the zwitterion of compound (Id) or the potassium salt of the compound (Id).
3. The solid form according to claim 1 , wherein said solid form is the dihydrate characterized by an x-ray powder diffraction pattern as obtained using CuKα1 radiation (λ=1.5406 Å) comprising one or more XRPD peaks as listed for the dihydrate in Table 2, group (a).
4. The solid form according to claim 1 , wherein said solid form is the dihydrate characterized by an x-ray powder diffraction pattern as obtained using CuKα1 radiation (λ=1.5406 Å) comprising peaks at the following 2θ-angles ±0.2° 2θ:10.4, 11.6, 12.3, 13.1, and 13.6°.
5. The solid form according to claim 4 , wherein said x-ray powder diffraction pattern further comprises one or more peaks selected from the group consisting of peaks at the following 2θ-angles ±0.2° 2θ: 14.3, 15.6, 16.0, 16.8, and 18.5°.
6. The solid form according to claim 1 , wherein said solid form is a crystal form characterized by an x-ray powder diffraction pattern as obtained using CuKα1 radiation (λ=1.5406 Å) essentially as depicted in FIG. 8 a.
7. The solid form according to claim 1 , said solid form exhibiting a weight loss of about 7.6% w/w compared to the initial weight when heated from about 30° C. to about 150° C. (heating rate 10° C./min).
8. The solid form according to claim 1 , wherein said solid form is the potassium salt characterized by an x-ray powder diffraction pattern as obtained using CuKα1 radiation (λ=1.5406 Å) comprising one or more XRPD peaks as listed for the potassium salt in Table 2, group (a).
9. The solid form according to claim 8 , wherein said potassium salt has a crystal form characterized by an XRPD obtained using CuKα1 radiation (λ=1.5406 Å) comprising peaks at the following 2θ-angles ±0.2° 2θ: 3.0, 9.0, 12.6, 13.6, and 15.0°.
10. The solid form according to claim 9 , wherein said x-ray powder diffraction pattern further comprises one or more peaks selected from the group consisting of peaks at the following 2θ-angles ±0.2° 2θ: 17.1, 18.0, 18.4, 18.8 and 19.4°.
11. The solid form according to claim 1 , said form exhibiting a weight loss of less than about 1% w/w compared to the initial weight when heated from about 20° C. to about 150° C. (heating rate 10° C/min).
12. A pharmaceutical composition comprising a therapeutically effective amount of the solid form of the compound of formula (Id) according to claim 1 , and one or more pharmaceutically acceptable excipients.
13. A method for the manufacture of a medicament comprising combining the solid form of the compound of formula (Id) according to claim 1 with one or more pharmaceutically acceptable excipients.
14. The solid form according to claim 1 , wherein said solid form is the dihydrate of the zwitterion of compound (Id).
15. The solid form according to claim 1 , wherein said solid form is the heptahydrate of the zwitterion of compound (Id).
16. The solid form according to claim 1 , wherein said solid form is the potassium salt of the compound (Id).