IP Library › Granted Patent US 12,421,271
Granted Patent B2
US 12,421,271 · App. 18/511,231 · Granted Sep 23, 2025

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

Inventors: Klaus Gjervig Jensen (Valby, DK); Lisbet Kværnø (Valby, DK); Morten Jørgensen (Valby, DK); Martin Juhl (Valby, DK); Heidi Lopez de Diego (Valby, DK); Frans Dennis Therkelsen (Valby, DK)
Assignee: H. Lundbeck A/S
C07H15/26C07B2200/13
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Quick Facts
Patent No.
US 12,421,271
App. No.
18/511,231
Granted
Sep 23, 2025
Kind
B2
Abstract

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.

Claims (28)

1. A solid form of a compound of formula (Id)

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) comprising peaks at the following 2θ-angles±0.2° 2θ:8.5, 11.1, 12.4, 12.9, and 15.6°.

2. 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) comprising peaks at the following 2θ-angles±0.1° 2θ:8.5, 11.1, 12.4, 12.9, and 15.6°.

3. The solid form according to claim 1 , 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:16.7, 18.9, 19.3, 20.0 and 21.2°.

4. The solid form according to claim 1 , wherein said x-ray powder diffraction pattern comprises peaks at the following 2θ-angles±0.2° 2θ:8.5, 11.1, 12.4, 12.9, 15.6, 16.7, 18.9, 19.3, 20.0, and 21.2°.

5. The solid form according to claim 1 , wherein said x-ray powder diffraction pattern comprises peaks at the following 2θ-angles±0.1° 2θ:8.5, 11.1, 12.4, 12.9, 15.6, 16.7, 18.9, 19.3, 20.0, and 21.2°.

6. The solid form according to claim 1 , wherein said x-ray powder diffraction pattern comprises peaks at the following 2θ-angles±0.2° 2θ:8.5, 11.1, 12.4, 12.9, 15.6, 16.7, 18.9, 19.3, 20.0, 21.2, 21.5, 22.2, 23.0, 24.2, 27.3, and 28.3°.

7. The solid form according to claim 1 , wherein said x-ray powder diffraction pattern comprises peaks at the following 2θ-angles±0.1° 2θ:8.5, 11.1, 12.4, 12.9, 15.6, 16.7, 18.9, 19.3, 20.0, 21.2, 21.5, 22.2, 23.0, 24.2, 27.3, and 28.3°.

8. The solid form according to claim 1 , wherein said x-ray powder diffraction pattern is essentially as depicted in FIG. 9 a.

9. The solid form according to claim 1 , wherein said solid form exhibits a weight loss of less than 1% w/w compared to the initial weight when heated from about 30° C. to about 150° C. (heating rate 10° C./min).

10. The solid form according to claim 1 , wherein said solid form is characterized by thermogravimetric analysis (heating rate 10° C./min) essentially as depicted in FIG. 9 b.

11. A solid form of a compound of formula (Id),

wherein said solid form is a crystal form characterized by thermogravimetric analysis (heating rate 10° C./min) essentially as depicted in FIG. 9 b.

12. A solid form of a compound of formula (Id),

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) comprising peaks at the following 2θ-angles±0.2° 2θ:8.5, 12.4, 12.9, 15.6, 16.7, 18.9, 19.3, 20.0, 21.2, 21.5, 22.2, 23.0, 24.2, 27.3 and 28.3°.

13. A solid form of a compound of formula (Id),

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) comprising peaks at the following 2θ-angles±0.1° 2θ:8.5, 12.4, 12.9, 15.6, 16.7, 18.9, 19.3, 20.0, 21.2, 21.5, 22.2, 23.0, 24.2, 27.3 and 28.3°.

14. 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.

15. The pharmaceutical composition according to claim 14 , wherein said solid form is characterized by an x-ray powder diffraction pattern as obtained using CuKα1 radiation (λ=1.5406 Å) further comprising one or more peaks selected from the group consisting of peaks at the following 2θ-angles±0.2° 2θ:16.7, 18.9, 19.3, 20.0, and 21.2°.

16. The pharmaceutical composition according to claim 15 , wherein said x-ray powder diffraction pattern comprises peaks at the following 2θ-angles±0.2° 2θ:8.5, 11.1, 12.4, 12.9, 15.6, 16.7, 18.9, 19.3, 20.0, and 21.2°.

17. The pharmaceutical composition according to claim 15 , wherein said x-ray powder diffraction pattern comprises peaks at the following 2θ-angles±0.1° 2θ:8.5, 11.1, 12.4, 12.9, 15.6, 16.7, 18.9, 19.3, 20.0, and 21.2°.

18. The pharmaceutical composition according to claim 14 , wherein said pharmaceutical composition is for oral administration.

19. The pharmaceutical composition according to claim 14 , wherein said pharmaceutical composition is a solid oral dosage form.

20. The pharmaceutical composition according to claim 14 , wherein said pharmaceutical composition is a tablet or a capsule for oral administration.

21. The pharmaceutical composition according claim 14 , wherein said pharmaceutical composition further comprises another agent which is useful in the treatment of a neurodegenerative disease or disorder.

22. The pharmaceutical composition according to claim 14 , wherein said pharmaceutical composition further comprises a compound selected from the group consisting of L-DOPA, droxidopa, foliglurax, a MAO-B inhibitor, selegiline, rasagiline, a COMT inhibitor, entacapone, tolcapone, an adenosine 2a antagonist, istradefylline, an antiglutamatergic agent, amantadine or memantine, an acetylcholinesterase inhibitor, rivastigmine, donepezil, galantamine, an antipsychotic agent, quetiapine, clozapine, risperidone, pimavanserin, olanzapine, haloperidol, aripiprazole or brexpiprazole; and an antibody targeting alpha-synuclein, Tau or A-beta protein.

23. The pharmaceutical composition according to claim 15 , wherein said x-ray powder diffraction pattern is essentially as depicted in FIG. 9 a.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE SECOND INVENTOR NAME AND THIRD INVENTOR NAME PREVIOUSLY RECORDED ON REEL 65761 FRAME 229. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT.. Recorded Jul 30, 2025
From: JENSEN, KLAUS GJERVIG; KVÆRNØ, LISBET; JØRGENSEN, MORTEN; JUHL, MARTIN; DE DIEGO, HEIDI LOPEZ; FREDHOLT, KARIN
To: H. LUNDBECK A/S
Reel/Frame 072293/0773 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 5, 2023
From: JENSEN, KLAUS GJERVIG; KVAERNO, LISBET; JORGENSEN, MORTEN; JUHL, MARTIN; DE DIEGO, HEIDI LOPEZ; FREDHOLT, KARIN
To: H. LUNDBECK A/S
Reel/Frame 065761/0229 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 5, 2023
From: JACOBSEN, MIKKEL FOG; FRIHED, TOBIAS GYLLING; THERKELSEN, FRANS
To: H. LUNDBECK A/S
Reel/Frame 065761/0367 →
Priority Claims (4)
DK PA201900598 · May 20, 2019 · national
DK PA201900599 · May 20, 2019 · national
DK PA201900612 · May 21, 2019 · national
DK PA201900636 · May 24, 2019 · national
Continuity (3)
Continuation 17392970 · Aug 3, 2021
Continuation 16876908 · May 18, 2020
Related Publication 20240190909A1 · Jun 13, 2024
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