IP Library › Granted Patent US 11,858,954
Granted Patent B2
US 11,858,954 · App. 17/392,970 · Granted Jan 2, 2024

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); Karin Fredholt (Valby, DK); Frans Dennis Therkelsen (Valby, DK); Tobias Gylling Frihed (Valby, DK); Mikkel Fog Jacobsen (Valby, DK)
Assignee: H. Lundbeck A/S
C07H15/26C07B2200/13
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Quick Facts
Patent No.
US 11,858,954
App. No.
17/392,970
Granted
Jan 2, 2024
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 (33)

1. A method for the treatment of a neurodegenerative disease or disorder, or a neuropsychiatric disease or disorder; said method comprising administration of a therapeutically effective amount of a crystalline solid form of a compound of formula (Id)

wherein said crystalline 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 compound (Id).

2. The method of treatment according to claim 1 , wherein said crystalline solid form is the dihydrate of the zwitterion of compound (Id) or the potassium salt of compound (Id).

3. The method of treatment according to claim 1 , wherein said crystalline solid form is the dihydrate of the zwitterion of compound (Id) characterized by an x-ray powder diffraction pattern as obtained using CuKα1 radiation (λ=1.5406 Å) comprising one or more peaks at the following 2θ-angles±0.2° 2θ: 10.4, 11.6, 12.3, 13.1, 13.6, 14.3, 15.6, 16.0, 16.8, and 18.5°.

4. The method of treatment according to claim 3 , wherein said crystalline solid form is the dihydrate of the zwitterion of compound (Id) 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 method of treatment 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 method of treatment according to claim 1 , wherein said crystalline 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 method of treatment according to claim 1 , said crystalline 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 method of treatment according to claim 1 , wherein said crystalline solid form is the potassium salt of compound (Id) characterized by an x-ray powder diffraction pattern as obtained using CuKα1 radiation (λ=1.5406 Å) comprising one or more peaks at the following 2θ-angles±0.2° 2θ: 3.0, 9.0, 12.6, 13.6, 15.0, 17.1, 18.0, 18.4, 18.8, and 19.4°.

9. The method of treatment according to claim 8 , wherein said x-ray powder diffraction pattern comprises peaks at the following 2θ-angles±0.2° 2θ: 3.0, 9.0, 12.6, 13.6, and 15.0°.

10. The method of treatment 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 method of treatment according to claim 1 , said crystalline solid 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. The method of treatment according to claim 1 , for treatment of a neurodegenerative disease or disorder selected from the group consisting of Parkinson's Disease, Huntington's disease, Restless leg syndrome, and Alzheimer's disease.

13. The method of treatment according to claim 12 , for treatment of Parkinson's Disease.

14. The method of treatment according to claim 1 , wherein said crystalline solid form is the dihydrate of the zwitterion of compound (Id).

15. The method of treatment according to claim 1 , wherein said crystalline solid form is the heptahydrate of the zwitterion of compound (Id).

16. The method of treatment according to claim 1 , wherein said crystalline solid form is the potassium salt of compound (Id).

17. The method according to claim 13 , wherein the crystalline solid form is the dihydrate of the zwitterion of compound (Id).

18. The method according to claim 13 , wherein the crystalline solid form is the heptahydrate of the zwitterion of compound (Id).

19. The method according to claim 13 , wherein the crystalline solid form is the potassium salt of compound (Id).

20. The method of treatment according to claim 5 , wherein said crystalline 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: 10.4, 11.6, 12.3, 13.1, 13.6, 14.3, 15.6, 16.0, 16.8, and 18.5°.

21. The method of treatment according to claim 20 , wherein said crystalline 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: 10.4, 11.6, 12.3, 13.1, 13.6, 14.3, 15.6, 16.0, 16.8, and 18.5°.

22. The method of treatment according to claim 5 , wherein said crystalline 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: 12.3, 13.1, 13.6, 16.0, 16.8, 18.5, 18.9, 19.4, 20.5, 21.4, 23.5, 24.7, 25.4, 26.9, and 28.7°.

23. The method of treatment according to claim 5 , wherein said crystalline 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: 12.3, 13.1, 13.6, 16.0, 16.8, 18.5, 18.9, 19.4, 20.5, 21.4, 23.5, 24.7, 25.4, 26.9, and 28.7°.

24. The method of treatment according to claim 10 , 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, 15.0, 17.1, 18.0, 18.4, 18.8, and 19.4°.

25. The method of treatment according to claim 24 , 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±0.1° 2θ: 3.0, 9.0, 12.6, 13.6, 15.0, 17.1, 18.0, 18.4, 18.8, and 19.4°.

26. The method of treatment according to claim 24 , wherein said crystalline solid form has a crystal form characterized by an XRPD obtained using CuKα1 radiation (=1.5406 Å) comprising peaks at the following 2θ-angles±0.2° 2θ: 3.0, 9.0, 12.6, 13.6, 15.0, 18.0, 19.4, 21.8, 24.7, 27.1, 29.8, 33.3, 35.6, 38.6, and 39.6°.

27. The method of treatment according to claim 26 , wherein said crystalline solid form has a crystal form characterized by an XRPD obtained using CuKα1 radiation (=1.5406 Å) comprising peaks at the following 2θ-angles±0.1° 2θ: 3.0, 9.0, 12.6, 13.6, 15.0, 18.0, 19.4, 21.8, 24.7, 27.1, 29.8, 33.3, 35.6, 38.6, and 39.6°.

28. The method of treatment according to claim 20 , for treatment of Parkinson's Disease.

29. The method of treatment according to claim 22 , for treatment of Parkinson's Disease.

30. The method of treatment according to claim 24 , for treatment of Parkinson's Disease.

31. The method of treatment according to claim 26 , for treatment of Parkinson's Disease.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE SECOND INVENTOR NAME AND THIRD INVENTOR NAME PREVIOUSLY RECORDED ON REEL 58839 FRAME 881. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jul 31, 2025
From: JENSEN, KLAUS GJERVIG; KVÆRNØ, LISBET; JØRGENSEN, MORTEN; JUHL, MARTIN; DE DIEGO, HEIDI LOPEZ; FREDHOLT, KARIN
To: H. LUNDBECK A/S
Reel/Frame 072310/0030 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2022
From: JENSEN, KLAUS GJERVIG; KVAERNO, LISBET; JORGENSEN, MORTEN; JUHL, MARTIN; LOPEZ DE DIEGO, HEIDI; FREDHOLT, KARIN
To: H. LUNDBECK A/S
Reel/Frame 058839/0881 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2022
From: THERKELSEN, FRANS; JACOBSEN, MIKKEL FOG; FRIHED, TOBIAS GYLLING
To: H. LUNDBECK A/S
Reel/Frame 058839/0931 →
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 (2)
Continuation 16876908 · May 18, 2020
Related Publication 20220024962A1 · Jan 27, 2022
Cited By (8)
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