IP Library Granted Patent US 8,414,922
Granted Patent B2
US 8,414,922 · App. 13/445,656 · Granted Apr 9, 2013

Sublingual films

Inventors: Nathan John Bryson (Toronto, CA); Anthony John Giovinazzo (Oakville, CA); Scott David Barnhart (York, PA); Michael Clinton Koons (York, PA)
Assignees: Cynapsus Therapeutics, Inc.; ARx, LLC
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,414,922
App. No.
13/445,656
Granted
Apr 9, 2013
Kind
B2
Abstract

The invention features sublingual film formulations of dopamine agonists and methods of treating Parkinson's disease, tremors, restless leg syndrome, sexual dysfunction, and depressive disorders therewith.

Claims (33)

1. A pharmaceutical composition in unit dosage form formulated for sublingual administration, wherein said unit dosage form is a film comprising:

(A) a first layer comprising:

(i) from 10 to 75% (w/w) apomorphine hydrochloride;

(ii) from 0.5 to 10% (w/w) a low molecular weight polymer having a weight average molecular weight of from 5 KDa to 50 KDa selected from hydroxypropyl cellulose, hydroxypropyl methyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, and methyl cellulose; and

(iii) from 4 to 35% (w/w) a high molecular weight polymer having a weight average molecular weight of greater than 60 KDa selected from hydroxypropyl cellulose, hydroxypropyl methyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, and methyl cellulose, and

(B) a second layer comprising:

(iv) from 6 to 65% (w/w) a pH neutralizing agent that is an organic base having a pKa of 5±2, and

(v) from 15 to 50% (w/w) of a high molecular weight polymer having a weight average molecular weight of greater than 60 KDa selected from hydroxypropyl cellulose, hydroxypropyl methyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, and methyl cellulose,

wherein said first layer comprises from 2 to 60 mg of apomorphine hydrochloride,

wherein, following sublingual administration to subjects, said unit dosage form produces an average circulating concentration of 3 to 6 ng/mL within a period of from 7 to 20 minutes, and

wherein said unit dosage form when placed in 1 mL of unbuffered water at pH 7 results in a solution having a pH of between 4.5 and 6.5.

2. The pharmaceutical composition of claim 1 , wherein said film further comprises from 3 to 12% (w/w) plasticizing agent.

3. The pharmaceutical composition of claim 2 , wherein said plasticizing agent is a polyol, oleic acid, or triacetin.

4. The pharmaceutical composition of claim 3 , wherein said plasticizing agent is a polyol selected from sorbitol, mannitol, maltitol, xylitol, glycerol, propylene glycol, and polyethylene glycol.

5. The pharmaceutical composition of claim 1 , wherein said film comprises from 1 to 50% (w/w) hydrolyzed starch.

6. The pharmaceutical composition of claim 5 , wherein said hydrolyzed starch is a dextrin or a maltodextrin.

7. The pharmaceutical composition of claim 1 , wherein said film further comprises an antioxidant.

8. The pharmaceutical composition of claim 7 , wherein said film further comprises from 0.05 to 2.5% (w/w) metabisulfite.

9. The pharmaceutical composition of claim 1 , wherein said film further comprises from 0.2 to 5% (w/w) of a permeation enhancer.

10. The pharmaceutical composition of claim 9 , wherein said permeation enhancer is glycerol monostearate.

11. The pharmaceutical composition of claim 1 , wherein said low molecular weight polymer is hydroxypropyl methyl cellulose, hydroxypropyl cellulose, or hydroxyethyl cellulose.

12. The pharmaceutical composition of claim 11 , wherein said hydroxypropyl methylcellulose has about 20% to about 35% methoxyl substitution and about 5% to about 15% hydroxypropyl substitution.

13. The pharmaceutical composition of claim 1 , wherein said high molecular weight polymer is hydroxypropyl methyl cellulose or hydroxyethyl cellulose.

14. The pharmaceutical composition of claim 13 , wherein said high molecular weight polymer is hydroxypropyl methyl cellulose having about 20% to about 35% methoxyl substitution and about 5% to about 15% hydroxypropyl substitution.

15. The pharmaceutical composition of claim 13 , wherein said high molecular weight polymer is hydroxyethyl cellulose having a weight average molecular weight of from 60 KDa to 1,000 KDa.

16. The pharmaceutical composition of claim 1 , wherein said organic base selected from pyridoxine, citrate, acetate, and histidine.

17. The pharmaceutical composition of claim 1 , wherein following sublingual administration to a subject said unit dosage form produces an average circulating concentration of at least 3 ng/mL within a period of from 5 to 15 minutes.

18. A method of treating Parkinson's disease in a subject, said method comprising sublingual administration of a pharmaceutical composition of claim 1 in an amount effective to treat said subject.

19. The pharmaceutical composition of claim 16 , wherein said organic base is pyridoxine.

20. The pharmaceutical composition of claim 1 , wherein said unit dosage form comprises 12±3 mg of apomorphine hydrochloride.

21. The pharmaceutical composition of claim 1 , wherein said unit dosage form comprises 22±4 mg of apomorphine hydrochloride.

22. The pharmaceutical composition of claim 1 , wherein said unit dosage form comprises 30±5 mg of apomorphine hydrochloride.

23. The pharmaceutical composition of claim 1 , wherein said unit dosage form comprises 35±5 mg of apomorphine hydrochloride.

Assignments (7)
CORRECTIVE ASSIGNMENT TO CORRECT THE EFFECTIVE DATE OF ASSIGNMENT PREVIOUSLY RECORDED AT REEL: 040277 FRAME: 0773. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Dec 15, 2016
From: SUNOVION CNS DEVELOPMENT CANADA ULC
To: SUNOVION PHARMACEUTICALS INC.
Reel/Frame 040940/0603 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 10, 2016
From: CYNAPSUS THERAPEUTICS INC.
To: PROJECT PEGASUS SUB ACQUISITION ULC
Reel/Frame 040587/0262 →
MERGER Recorded Nov 10, 2016
From: PROJECT PEGASUS SUB ACQUISITION ULC
To: SUNOVION CNS DEVELOPMENT CANADA ULC
Reel/Frame 040588/0155 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 10, 2016
From: SUNOVION CNS DEVELOPMENT CANADA ULC
To: SUNOVION PHARMACEUTICALS INC.
Reel/Frame 040277/0773 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2015
From: ARX, LLC
To: CYNAPSUS THERAPEUTICS, INC.
Reel/Frame 035230/0355 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 12, 2013
From: GIOVINAZZO, ANTHONY JOHN; BRYSON, NATHAN JOHN
To: CYNAPSUS THERAPEUTICS, INC.
Reel/Frame 029975/0299 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 12, 2013
From: BARNHART, SCOTT DAVID; KOONS, MICHAEL CLINTON
To: ARX, LLC
Reel/Frame 029975/0394 →
Continuity (4)
Continuation PCTUS2011065665 · Dec 16, 2011
Provisional Application 61483864 · May 9, 2011
Provisional Application 61423858 · Dec 16, 2010
Related Publication 20120195955A1 · Aug 2, 2012