IP Library Granted Patent US 10,028,912
Granted Patent B2
US 10,028,912 · App. 14/352,662 · Granted Jul 24, 2018

Method of lyophilizing liposomes

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Quick Facts
Patent No.
US 10,028,912
App. No.
14/352,662
Granted
Jul 24, 2018
Kind
B2
Abstract

Lyophilized liposomal formulations with two or more encapsulated drugs are disclosed. These formulations display superior drug retention profiles and also maintain size distribution following lyophilization and reconstitution.

Claims (22)

1. A lyophilized gel-phase liposomal composition, wherein said gel-phase liposomes exhibit a melting phase temperature (T c ) of at least 37° C. and the liposome membrane is comprised of distearyl phosphatidyl choline (DSPC):distearyl phosphatidyl glycerol (DSPG):cholesterol at a molar ratio of 7:2:1; and

said liposomes are stably associated with daunorubicin:cytarabine at a molar ratio of 1:5; and

contain less than 50 mM internal cryoprotectant; and

wherein a cryoprotectant that consists of one or more saccharides is present external to said liposomes; and

wherein when said gel-phase liposomal composition is reconstituted, the mean diameter of the liposomes increases by no more than 25% as compared to said value measured prior to lyophilization and at least 90% of each agent is retained.

2. The composition of claim 1 wherein the ratio of daunorubicin:cytarabine changes by no more than 25% as compared to said composition prior to lyophilization.

3. The composition of claim 1 wherein the mean diameter of the liposomes increases by no more than 15% after lyophilization and upon reconstitution of said liposomes as compared to said value measured prior to lyophilization.

4. The composition of claim 3 wherein the mean diameter of the liposomes increases by no more than 10% after lyophilization and upon reconstitution of said liposomes as compared to said value measured prior to lyophilization.

5. The composition of claim 1 wherein the size distribution of the liposomes changes by no more than 25% after lyophilization and upon reconstitution of said liposomes.

6. The composition of claim 5 wherein the size distribution of the liposomes changes by no more than 15% after lyophilization and upon reconstitution of said liposomes.

7. The composition of claim 6 wherein the size distribution of the liposomes changes by no more than 10% after lyophilization and upon reconstitution of said liposomes.

8. A method to prepare the composition of claim 1 which method comprises subjecting to lyophilization an aqueous medium comprising gel-phase liposomes that exhibit a melting phase temperature (T c ) of at least 37° C. and the liposome membrane is comprised of distearyl phosphatidyl choline (DSPC):distearyl phosphatidyl glycerol (DSPG):cholesterol at a molar ratio of 7:2:1 and said liposomes are stably associated with daunorubicin:cytarabine at a molar ratio of 1:5 and contain less than 50 mM internal cryoprotectant, in the presence of external protectant that consists of one or more saccharides.

9. The method of claim 8 wherein said medium comprising gel-phase liposomes is frozen at a temperature which is below the glass transition temperature (T g ) of said medium.

10. A method to prepare a pharmaceutical composition for administering therapeutic and/or diagnostic agents to a subject which method comprises reconstituting the liposomal composition of claim 1 in a pharmaceutical carrier to obtain a reconstituted composition.

11. A method to administer therapeutic and/or diagnostic agents to an animal subject which method comprises administering to said subject the reconstituted composition of claim 10 .

12. The method of claim 11 wherein said administering is parenteral.

13. The method of claim 11 wherein the subject is human.

14. The composition of claim 1 wherein said mean diameter is maintained for at least 6 months upon storage at 5° C. or at 25° C.

15. The composition of claim 1 wherein said retaining is maintained for at least 6 months upon storage at 5° C. or at 25° C.

16. The composition of claim 1 wherein said cryoprotectant external to said liposomes comprises sucrose.

17. The composition of claim 1 wherein the external medium contains 250 mM-400 mM cryoprotectant.

18. The composition of claim 17 wherein the medium contains about 300 mM cryoprotectant.

Assignments (7)
CORRECTIVE ASSIGNMENT TO CORRECT THE REMOVE 2 APPLICATION NUMBERS PREVIOUSLY RECORDED AT REEL: 07234 FRAME: 0137. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Oct 9, 2025
From: CELATOR PHARMACEUTICALS, INC.
To: JAZZ PHARMACEUTICALS THERAPEUTICS, INC.
Reel/Frame 073133/0142 →
CORRECTIVE ASSIGNMENT TO CORRECT THE REMOVAL OF 8 PROPERTY NUMBERS PREVIOUSLY RECORDED AT REEL: 072341 FRAME: 0137. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Oct 8, 2025
From: CELATOR PHARMACEUTICALS, INC.
To: JAZZ PHARMACEUTICALS THERAPEUTICS, INC.
Reel/Frame 073058/0985 →
CHANGE OF NAME Recorded Aug 7, 2025
From: CELATOR PHARMACEUTICALS, INC.
To: JAZZ PHARMACEUTICALS THERAPEUTICS, INC.
Reel/Frame 072341/0137 →
SECURITY AGREEMENT Recorded May 5, 2021
From: CAVION, INC.; CELATOR PHARMACEUTICALS, INC.; JAZZ PHARMACEUTICALS IRELAND LIMITED; JAZZ PHARMACEUTICALS, INC.
To: U.S. BANK NATIONAL ASSOCIATION
Reel/Frame 056151/0010 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2021
From: BANK OF AMERICA, N.A.
To: JAZZ PHARMACEUTICALS, INC.; JAZZ PHARMACEUTICALS IRELAND LIMITED; JAZZ PHARMACEUTICALS INTERNATIONAL LIMITED; JAZZ PHARMACEUTICALS INTERNATIONAL III LIMITED; CELATOR PHARMACEUTICALS, INC.; CAVION, INC.
Reel/Frame 056150/0708 →
SECURITY AGREEMENT Recorded Jul 12, 2016
From: CELATOR PHARMACEUTICALS, INC.
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 039312/0397 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2014
From: CABRAL-LILLY, DONNA; MAYER, LAWRENCE; TARDI, PAUL; WATKINS, DAVID; ZENG, YI
To: CELATOR PHARMACEUTICALS, INC.
Reel/Frame 033011/0685 →
Cited By (16)
US 12,186,296 US 12,186,298 US 12,226,377 US 12,226,388 US 12,226,389 US 12,239,625 US 12,257,223 US 12,263,150 US 12,263,151 US 12,295,926 US 12,303,478 US 12,370,207 US 12,478,604 US 12,551,457 US 12,642,811 US 12,697,247