IP Library Granted Patent US 10,045,988
Granted Patent B2
US 10,045,988 · App. 15/645,054 · Granted Aug 14, 2018

Spirocyclic compounds as tryptophan hydroxylase inhibitors

Inventors: Stéphane De Lombaert (Brisbane, CA); Daniel R. Goldberg (Seattle, WA); Kenneth Brameld (Menlo Park, CA); Eric Brian Sjogren (Mountain View, CA); Andrew Scribner (Durham, NC)
Assignee: Roivant Sciences GmbH
A61K31/506A61K9/0014A61K9/0019A61K9/0053A61K9/0078
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Quick Facts
Patent No.
US 10,045,988
App. No.
15/645,054
Granted
Aug 14, 2018
Kind
B2
Abstract

The present invention is directed to spirocyclic compounds which are inhibitors of tryptophan hydroxylase (TPH), particularly isoform 1 (TPH1), that are useful in the treatment of diseases or disorders associated with peripheral serotonin including, for example, gastrointestinal, cardiovascular, pulmonary, inflammatory, metabolic, and low bone mass diseases, as well as serotonin syndrome, and cancer.

Claims (26)

1. A pharmaceutical composition suitable for administration to a patient by inhalation comprising (S)-8-(2-amino-6-((R)-1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

2. The composition of claim 1 , wherein the composition is in the form of a powder.

3. The composition of claim 1 , wherein the composition is administered as a spray or aerosol.

4. The composition of claim 3 , wherein the aerosol is administered by a sonic nebulizer.

5. A method of lowering peripheral serotonin in a patient comprising administering by inhalation to the patient a composition of claim 1 .

6. A method of treating pulmonary arterial hypertension (PAH) in a patient, comprising administering by inhalation to the patient a therapeutically effective amount of a composition of claim 1 .

7. The method of claim 6 , wherein the PAH is associated pulmonary arterial hypertension (APAH).

8. A pharmaceutical composition suitable for administration to a patient by injection or infusion comprising (S)-8-(2-amino-6-((R)-1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

9. The composition of claim 8 , wherein the injection is subcutaneous, intravenous, or intramuscular.

10. The composition of claim 8 , wherein the composition is suitable for administration to a patient by infusion.

11. The composition of claim 8 , wherein the composition comprises one or more pharmaceutically acceptable sterile isotonic aqueous or non-aqueous solutions, dispersions, suspensions, or emulsions.

12. A method of lowering peripheral serotonin in a patient comprising administering by injection or infusion to the patient a composition of claim 8 .

13. A method of treating pulmonary arterial hypertension (PAH) in a patient, comprising administering by injection or infusion to the patient a therapeutically effective amount of a composition of claim 8 .

14. The method of claim 13 , wherein the PAH is associated pulmonary arterial hypertension (APAH).

15. A pharmaceutical composition suitable for topical administration to a patient comprising (S)-8-(2-amino-6-((R)-1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

16. The composition of claim 15 , wherein the composition is administered in the form of a powder, spray, ointment, paste, cream, lotion, gel, solution, or patch.

17. A method of lowering peripheral serotonin in a patient comprising topically administering to the patient a composition of claim 15 .

18. A method of treating pulmonary arterial hypertension (PAH) in a patient, comprising topically administering to the patient a therapeutically effective amount of a composition of claim 15 .

19. The method of claim 18 , wherein the PAH is associated pulmonary arterial hypertension (APAH).

20. A pharmaceutical composition suitable for oral administration to a patient comprising (S)-8-(2-amino-6-((R)-1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

21. The composition of claim 20 , wherein the composition is prepared in the form of a capsule, a tablet, a pill, a dragee, a powder, or granules.

22. A method of lowering peripheral serotonin in a patient comprising orally administering to the patient a composition of claim 20 .

23. A method of treating pulmonary arterial hypertension (PAH) in a patient, comprising orally administering to the patient a therapeutically effective amount of a composition of claim 20 .

24. The method of claim 23 , wherein the PAH is associated pulmonary arterial hypertension (APAH).

25. A method of treating pulmonary arterial hypertension (PAH) in a patient, comprising administering to the patient a therapeutically effective amount of (S)-8-(2-amino-6-((R)-1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid, or a pharmaceutically acceptable salt thereof.

26. The method of claim 25 , wherein the PAH is associated pulmonary arterial hypertension (APAH).

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2021
From: ROIVANT SCIENCES GMBH
To: ALTAVANT SCIENCES GMBH
Reel/Frame 055536/0102 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2017
From: KAROS PHARMACEUTICALS, INC.
To: ROIVANT SCIENCES GMBH
Reel/Frame 044069/0338 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2017
From: KAROS PHARMACEUTICALS, INC.
To: ROIVANT SCIENCES GMBH
Reel/Frame 043716/0336 →
CONFIRMATORY ASSIGNMENT Recorded Jul 11, 2017
From: SCYNEXIS, INC.
To: KAROS PHARMACEUTICALS, INC.
Reel/Frame 043150/0890 →
CHANGE OF NAME Recorded Jul 11, 2017
From: SCYNEXIS CHEMISTRY & AUTOMATION, INC.
To: SCYNEXIS, INC.
Reel/Frame 043150/0866 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 11, 2017
From: DE LOMBAERT, STÉPHANE; GOLDBERG, DANIEL R.; BRAMELD, KENNETH; SJOGREN, ERIC BRIAN; SCRIBNER, ANDREW
To: KAROS PHARMACEUTICALS, INC.
Reel/Frame 042968/0493 →
CONFIRMATORY ASSIGNMENT Recorded Jul 11, 2017
From: SCRIBNER, ANDREW
To: SCYNEXIS CHEMISTRY & AUTOMATION, INC.
Reel/Frame 043150/0814 →
Continuity (7)
Continuation 15278130 · Sep 28, 2016
Continuation 14841868 · Sep 1, 2015
Continuation 14477948 · Sep 5, 2014
Provisional Application 61874545 · Sep 6, 2013
Provisional Application 61899943 · Nov 5, 2013
Provisional Application 62004385 · May 29, 2014
Related Publication 20180092918A1 · Apr 5, 2018