IP Library Granted Patent US 10,987,402
Granted Patent B2
US 10,987,402 · App. 16/512,536 · Granted Apr 27, 2021

Pharmaceutical compositions of water soluble peptides with poor solubility in isotonic conditions and methods for their use

Inventor: Michel Afargan (Ra'anana, IL)
Assignee: Strongbridge Dublin Limited
A61K38/08A61K9/0019A61K9/107A61K9/127A61K9/5031A61K9/5089A61K47/12A61K47/36
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 10,987,402
App. No.
16/512,536
Granted
Apr 27, 2021
Kind
B2
Abstract

The present invention provides compositions comprising water soluble peptides with poor solubility in isotonic solutions which exhibit enhanced bioavailability with reduced adverse effects including injection site reactions. Methods are also disclosed for using such compositions for the treatment of diseases including, but not limited to, cancer, type 2 diabetes, acromegaly, metabolic disorders, endocrine disorders, exocrine tumors, and hormone-related tumors. Methods to reduce adverse injection site reactions and improve bioavailability are also disclosed.

Claims (28)

1. A pharmaceutical composition comprising:

veldoreotide acetate;

an excipient, wherein the excipient comprises a monosaccharide, a disaccharide, polysaccharide, cyclic polysaccharide, cyclic oligosaccharide, cyclodextrin or β-cyclodextrin;

and a polymeric microsphere, wherein veldoreotide acetate-is encapsulated in the polymeric microsphere, and wherein the surface area of the polymeric microsphere is from about 7 m 2 /g to about 12 m 2 /g.

2. The pharmaceutical composition of claim 1 , wherein the diameter of the polymeric microsphere is from about 10 microns to about 100 microns.

3. The pharmaceutical composition of claim 1 , wherein the polymeric microsphere comprises poly(lactic-co-glycolic acid) (PLGA).

4. The pharmaceutical composition of claim 1 , wherein the microsphere comprises a plurality of internal voids separated by thin interstitial boundaries.

5. The pharmaceutical composition of claim 1 , wherein the microsphere further comprises an excipient selected from the group consisting of a sugar, an amino acid, and nicotinamide.

6. The pharmaceutical composition of claim 1 , wherein the amount of monosaccharide is from about 0.1 weight % to about 1.0 weight % based on the total weight of the polymeric microsphere.

7. The pharmaceutical composition of claim 1 , wherein the excipient comprises lysine, arginine, or a pharmaceutically acceptable salt thereof.

8. A process for manufacturing polymeric microspheres comprising the steps of:

(i) mixing an excipient comprising a sugar or an amino acid, and veldoreotide or a pharmaceutically acceptable salt thereof in water to form a first aqueous mixture;

(ii) mixing a polymer in organic solvent to form a polymeric solution;

(iii) mixing the first aqueous mixture in the polymeric solution to form a first dispersion mixture comprising a water-in-oil primary emulsion;

(iv) mixing polyvinyl alcohol (PVA) in phosphate buffered saline or in saline to form a second aqueous mixture;

(v) mixing the primary emulsion in the second aqueous mixture of PVA to form a water-in-oil-in-water double emulsion thereby providing a secondary dispersion mixture; and

(vi) allowing the organic solvent in the secondary dispersion mixture to evaporate to form polymeric microspheres comprising veldoreotide or pharmaceutically acceptable salt thereof.

9. The process of claim 8 , wherein the pharmaceutically acceptable salt of veldoreotide is veldoreotide acetate.

10. The process of claim 8 , wherein the polymeric solution comprises poly(lactic-co-glycolic acid) (PLGA).

11. The process of claim 8 , wherein the excipient comprises a monosaccharide, a disaccharide, polysaccharide, cyclic polysaccharide, cyclic oligosaccharide, cyclodextrin or β-cyclodextrin.

12. The process of claim 11 , wherein the excipient comprises a monosaccharide.

13. The process of claim 12 , wherein the mass ratio of monosaccharide to veldoreotide or pharmaceutically acceptable salt thereof is from 1:4 to 1:16.

14. The process of claim 12 , wherein the mass ratio of monosaccharide to veldoreotide or pharmaceutically acceptable salt thereof is from 1:6 to 1:10.

15. The process of claim 12 , wherein the mass ratio of monosaccharide to veldoreotide or pharmaceutically acceptable salt thereof is 1:8.

16. The process of claim 11 , wherein the excipient comprises a cyclodextrin.

17. The process of claim 16 wherein the mass ratio of cyclodextrin to veldoreotide or pharmaceutically acceptable salt thereof is from 1:1 to 1:8.

18. The process of claim 16 , wherein the mass ratio of cyclodextrin to veldoreotide or pharmaceutically acceptable salt thereof is from 1:2 to 1:4.

19. The process of claim 8 , wherein the excipient comprises lysine, arginine, or a pharmaceutically acceptable salt thereof.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 7, 2025
From: STRONGBRIDGE IRELAND LIMITED
To: STRONGBRIDGE DUBLIN LIMITED
Reel/Frame 071056/0913 →
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NO. 16/863,125 TO READ--APPLICATION NO. 62/863,125-- PREVIOUSLY RECORDED AT REEL: 057702 FRAME: 0311. ASSIGNOR(S) HEREBY CONFIRMS THE RELEASE OF SECURITY AGREEMENT. Recorded Jul 25, 2023
From: AVENUE VENTURE OPPORTUNITIES FUND, L.P.
To: STRONGBRIDGE DUBLIN LIMITED
Reel/Frame 064444/0038 →
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NUMBER PREVIOUSLY RECORDED AT REEL: 052705 FRAME: 0039. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY INTEREST. Recorded Jul 21, 2023
From: STRONGBRIDGE DUBLIN LIMITED
To: AVENUE VENTURE OPPORTUNITIES FUND, L.P.
Reel/Frame 064357/0750 →
SECURITY INTEREST Recorded Mar 9, 2022
From: XERIS PHARMACEUTICALS, INC.; STRONGBRIDGE DUBLIN LIMITED
To: HAYFIN SERVICES LLP
Reel/Frame 059552/0066 →
RELEASE OF SECURITY INTEREST Recorded Oct 5, 2021
From: AVENUE VENTURE OPPORTUNITIES FUND, L.P.
To: STRONGBRIDGE DUBLIN LIMITED
Reel/Frame 057702/0311 →
SECURITY INTEREST Recorded May 19, 2020
From: STRONGBRIDGE DUBLIN LIMITED
To: AVENUE VENTURE OPPORTUNITIES FUND, L.P.
Reel/Frame 052705/0039 →
Continuity (5)
Continuation 15984646 · May 21, 2018
Continuation 15487731 · Apr 14, 2017
Continuation PCTIB2017000194 · Feb 16, 2017
Provisional Application 62295545 · Feb 16, 2016
Related Publication 20190336567A1 · Nov 7, 2019