IP Library Granted Patent US 11,529,431
Granted Patent B2
US 11,529,431 · App. 17/688,532 · Granted Dec 20, 2022

Methods for making ultrasound contrast agents

Inventors: Simon P. Robinson (Stow, MA); Robert W. Siegler (Bedford, MA); Nhung Tuyet Nguyen (Westford, MA); David C. Onthank (Groton, MA); Tarakeshwar Vishwanath Anklekar (Billerica, MA); Charles Chester Van Kirk (Beverly, MA)
Assignee: Lantheus Medical Imaging, Inc.
A61K49/223A61B8/481A61K49/226A61K49/227C07F9/09C07F9/106
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Quick Facts
Patent No.
US 11,529,431
App. No.
17/688,532
Granted
Dec 20, 2022
Kind
B2
Abstract

Provided herein are improved methods for preparing phospholipid formulations including phospholipid UCA formulations.

Claims (39)

1. A method of ultrasound contrast imaging a subject comprising

(a) combining one or more phospholipids and a non-aqueous solvent, in a methanol and toluene free and methyl t-butyl ether free condition, to form a phospholipid solution having calcium and/or magnesium divalent metal cation present at a total divalent metal cation concentration of less than 0.7 ppm,

(b) combining the phospholipid solution with an aqueous solution to form a phospholipid suspension,

(c) activating the phospholipid suspension with a perfluorocarbon gas to form lipid-encapsulated gas microspheres,

(d) administering the lipid-encapsulated gas microspheres to a subject, and

(e) obtaining an ultrasound image of the subject.

2. The method of claim 1 , wherein the one or more phospholipids comprise (a) DPPC and MPEG-5000-DPPE or (b) DPPA, DPPC and MPEG-5000-DPPE.

3. The method of claim 1 , wherein the one or more phospholipids comprise DPPA, DPPC and MPEG-5000-DPPE.

4. The method of claim 2 , wherein DPPC has a combined calcium and magnesium concentration of less than 90 ppm, and MPEG5000-DPPE has a combined calcium and magnesium concentration of less than 115 ppm.

5. The method of claim 1 , wherein the non-aqueous solvent comprises propylene glycol.

6. The method of claim 1 , wherein the non-aqueous solvent has a combined calcium and magnesium concentration of less than 0.7 ppm.

7. The method of claim 1 , wherein the non-aqueous solvent comprises propylene glycol and glycerol.

8. The method of claim 1 , wherein the phospholipid solution has no detectable phospholipid precipitate.

9. The method of claim 1 , wherein the one or more phospholipids comprise DPPA, DPPC and MPEG-5000-DPPE in molar percentages of 5-15%, 77-90% and 5-15%, respectively.

10. The method of claim 1 , wherein the one or more phospholipids comprise DPPA, DPPC and MPEG-5000-DPPE in a mole % ratio of 10 to 82 to 8 (10:82:8).

11. The method of claim 1 , wherein the perfluorocarbon gas is perfluoropropane gas.

12. The method of claim 1 , wherein the one or more phospholipids comprise DPPC and MPEG-5000-DPPE, the phospholipid solution comprises DPPC, MPEG5000-DPPE and propylene glycol, the aqueous solution comprises water, propylene glycol and glycerol, and the phospholipid suspension comprises DPPC, MPEG5000-DPPE, propylene glycol, water and glycerol.

13. The method of claim 1 , wherein the aqueous solution further comprises one or more salts.

14. The method of claim 1 , wherein the aqueous solution further comprises one or more buffers.

15. A method of ultrasound contrast imaging a subject comprising

(a) selecting an MPEG5000-DPPE having calcium and/or magnesium divalent metal cation present at a total divalent metal cation concentration of less than 115 parts per million (ppm),

(b) combining the MPEG-5000-DPPE with one or more phospholipids and a non-aqueous solvent, in a methanol and toluene free and methyl t-butyl ether free condition, to form a phospholipid solution having calcium and/or magnesium divalent metal cation present at a total divalent metal cation concentration of less than 0.7 ppm,

(c) combining the phospholipid solution with an aqueous solution to form a phospholipid suspension,

(d) activating the phospholipid suspension with a perfluorocarbon gas to form lipid-encapsulated gas microspheres,

(e) administering the lipid-encapsulated gas microspheres to a subject, and

(f) obtaining an ultrasound image of the subject.

16. The method of claim 15 , wherein the MPEG-5000-DPPE with the one or more phospholipids comprise (a) DPPC and MPEG-5000-DPPE or (b) DPPA, DPPC and MPEG-5000-DPPE.

17. The method of claim 15 , wherein the MPEG-5000-DPPE with the one or more phospholipids comprise DPPA, DPPC and MPEG-5000-DPPE.

18. The method of claim 16 , wherein DPPC has a combined calcium and magnesium concentration of less than 90 ppm, and MPEG5000-DPPE has a combined calcium and magnesium concentration of less than 115 ppm.

19. The method of claim 15 , wherein the non-aqueous solvent comprises propylene glycol.

20. The method of claim 15 , wherein the non-aqueous solvent has a combined calcium and magnesium concentration of less than 0.7 ppm.

21. The method of claim 15 , wherein the non-aqueous solvent comprises propylene glycol and glycerol.

22. The method of claim 15 , wherein the phospholipid solution has no detectable phospholipid precipitate.

23. The method of claim 15 , wherein the MPEG-5000-DPPE with the one or more phospholipids comprise DPPA, DPPC and MPEG-5000-DPPE in molar percentages of 5-15%, 77-90% and 5-15%, respectively.

24. The method of claim 15 , wherein the MPEG-5000-DPPE with the one or more phospholipids comprise DPPA, DPPC and MPEG-5000-DPPE in a mole % ratio of 10 to 82 to 8 (10:82:8).

25. The method of claim 15 , wherein the perfluorocarbon gas is perfluoropropane gas.

26. The method of claim 15 , wherein the MPEG-5000-DPPE with the one or more phospholipids comprise DPPC and MPEG-5000-DPPE, the phospholipid solution comprises DPPC, MPEG5000-DPPE and propylene glycol, the aqueous solution comprises water, propylene glycol and glycerol, and the phospholipid suspension comprises DPPC, MPEG5000-DPPE, propylene glycol, water and glycerol.

27. The method of claim 15 , wherein the aqueous solution further comprises one or more salts.

28. The method of claim 15 , wherein the aqueous solution further comprises one or more buffers.

Assignments (3)
SECURITY INTEREST Recorded Jun 1, 2023
From: LANTHEUS MEDICAL IMAGING, INC.; PROGENICS PHARMACEUTICALS, INC.
To: CITIZENS BANK, N.A.
Reel/Frame 063827/0207 →
SECURITY INTEREST Recorded Dec 2, 2022
From: LANTHEUS MEDICAL IMAGING, INC.; MOLECULAR INSIGHT PHARMACEUTICALS, INC.; PSMA DEVELOPMENT COMPANY, LLC; PROGENICS PHARMACEUTICALS, INC.
To: CITIZENS BANK, N.A.
Reel/Frame 062047/0960 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2022
From: ROBINSON, SIMON P.; SIEGLER, ROBERT W.; NGUYEN, NHUNG TUYET; ONTHANK, DAVID C.; ANKLEKAR, TARAKESHWAR VISHWANATH; VAN KIRK, CHARLES CHESTER
To: LANTHEUS MEDICAL IMAGING, INC.
Reel/Frame 060745/0793 →