CA2317921A1 - Preparation of a lipid blend and a phospholipid suspension containing the lipid blend - Google Patents
Preparation of a lipid blend and a phospholipid suspension containing the lipid blend Download PDFInfo
- Publication number
- CA2317921A1 CA2317921A1 CA002317921A CA2317921A CA2317921A1 CA 2317921 A1 CA2317921 A1 CA 2317921A1 CA 002317921 A CA002317921 A CA 002317921A CA 2317921 A CA2317921 A CA 2317921A CA 2317921 A1 CA2317921 A1 CA 2317921A1
- Authority
- CA
- Canada
- Prior art keywords
- process according
- suspension
- lipid
- aqueous solvent
- lipid blend
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- 150000002632 lipids Chemical class 0.000 title claims abstract 36
- 239000000203 mixture Substances 0.000 title claims abstract 29
- 239000000725 suspension Substances 0.000 title claims abstract 28
- 150000003904 phospholipids Chemical class 0.000 title claims abstract 12
- 238000000034 method Methods 0.000 claims abstract 40
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 18
- 239000003125 aqueous solvent Substances 0.000 claims 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 9
- 239000007864 aqueous solution Substances 0.000 claims 9
- 239000000243 solution Substances 0.000 claims 9
- 239000011780 sodium chloride Substances 0.000 claims 8
- 235000011187 glycerol Nutrition 0.000 claims 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 6
- 230000001954 sterilising effect Effects 0.000 claims 5
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000001914 filtration Methods 0.000 claims 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 claims 2
- 230000007704 transition Effects 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 238000004090 dissolution Methods 0.000 claims 1
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 claims 1
- 229960004065 perflutren Drugs 0.000 claims 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000002961 echo contrast media Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/22—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations
- A61K49/222—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations characterised by a special physical form, e.g. emulsions, liposomes
- A61K49/226—Solutes, emulsions, suspensions, dispersions, semi-solid forms, e.g. hydrogels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
- A61K9/1277—Processes for preparing; Proliposomes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B8/00—Diagnosis using ultrasonic, sonic or infrasonic waves
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/22—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations
- A61K49/222—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations characterised by a special physical form, e.g. emulsions, liposomes
- A61K49/227—Liposomes, lipoprotein vesicles, e.g. LDL or HDL lipoproteins, micelles, e.g. phospholipidic or polymeric
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
Abstract
The present invention describes processes for the preparation of a lipid blend and a uniform filterable phospholipid suspension containing the lipid blend, such suspension being useful as an ultrasound contrast agent.
Claims (44)
1. A process for preparing a phospholipid suspension, comprising:
(1) contacting a lipid blend with a non-aqueous solvent, whereby the lipid blend substantially dissolves in the non-aqueous solvent; and, (2) contacting the solution from step (1) with an aqueous solution to form a lipid suspension.
(1) contacting a lipid blend with a non-aqueous solvent, whereby the lipid blend substantially dissolves in the non-aqueous solvent; and, (2) contacting the solution from step (1) with an aqueous solution to form a lipid suspension.
2. A process according to Claim 1, wherein the non-aqueous solvent is selected from propylene glycol, ethylene glycol, and polyethylene glycol 300.
3. A process according to Claim 2, wherein the non-aqueous solvent is propylene glycol.
4. A process according to Claim 2, wherein the lipid blend, comprises:
(a) 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine;
(b) 1,2-dipalmitoyl-sn-glycero-3-phosphotidic, mono sodium salt; and, (c) N-(methoxypolyethylene glycol 5000 carbamoyl)-1,2-dipalmitoyl-sn-glycero-3-phosphatidylethanolamine, mono sodium salt.
(a) 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine;
(b) 1,2-dipalmitoyl-sn-glycero-3-phosphotidic, mono sodium salt; and, (c) N-(methoxypolyethylene glycol 5000 carbamoyl)-1,2-dipalmitoyl-sn-glycero-3-phosphatidylethanolamine, mono sodium salt.
5. A process according to Claim 2, wherein the non-aqueous solvent is heated to a temperature of about 30 to 70°C prior to contacting with the lipid blend.
6. A process according to Claim 5, wherein the non-aqueous solvent is heated to a temperature of about 50 to 55°C prior to contacting with the lipid blend.
7. A process according to Claim 2, wherein the ratio of lipid blend to non-aqueous solvent is from about 5 mg of lipid blend per mL of non-aqueous solvent to about 15 mg/mL.
8. A process according to Claim 7, wherein the ratio of lipid blend to non-aqueous solvent is about 10 mg/mL.
9. A process according to Claim 2, wherein in step (2), the aqueous solution is selected from water, saline, a saline/glycerin mixture, and a saline/glycerin/non-aqueous solvent mixture.
10. A process according to Claim 9, wherein the aqueous solution is a saline and glycerin mixture.
11. A process according to Claim 9, wherein the aqueous solution is a saline, glycerin, and propylene glycol mixture.
12. A process according to Claim 11, wherein 6.8 mg/mL
of sodium chloride are present, 0.1 mL/mL of glycerin are present, 0.1 mL/mL of propylene glycol are present, and about 0.75 to 1.0 mg/mL of the lipid blend are present.
of sodium chloride are present, 0.1 mL/mL of glycerin are present, 0.1 mL/mL of propylene glycol are present, and about 0.75 to 1.0 mg/mL of the lipid blend are present.
13. A process according to Claim 12, wherein 0.75 mg/mL of lipid blend are present.
14. A process according to Claim 12, wherein 1.0 mg/mL, of lipid blend are present.
15. A process according to Claim 2, wherein in step (2), the aqueous solution is heated to a temperature of about 45 to 60°C prior to contacting with the solution from step (1).
16. A process according to Claim 15, wherein the aqueous solution is heated to a temperature of about 50 to 55°C prior to contacting with the solution from step (1).
17. A process according to Claim 1, wherein the process further comprises:
(3) heating the lipid suspension from step (2) to a temperature about equal to or above the highest gel to liquid crystalline phase transition temperature of the lipids present in the suspension.
(3) heating the lipid suspension from step (2) to a temperature about equal to or above the highest gel to liquid crystalline phase transition temperature of the lipids present in the suspension.
18. A process according to Claim 17, wherein in step (3), the lipid suspension is heated to a temperature of at least about 67°C.
19. A process according to Claim 17, wherein the process further comprises:
(4) filtering the lipid suspension through a sterilizing filter.
(4) filtering the lipid suspension through a sterilizing filter.
20. A process according to Claim 19, wherein in step (4), the filtration is performed using two sterilizing filter cartridges.
21. A process according to Claim 20, wherein in step (4), the sterilizing filter cartridges are at a temperature of from about 70 to 80°C.
22. A process according to Claim 21, wherein in step (4), 0.2um hydrophilic filters are used.
23. A process according to Claim 19, wherein the process further comprises:
(5) dispensing the filtered solution from step (4) into a vial.
(5) dispensing the filtered solution from step (4) into a vial.
24. A process according to Claim 23, wherein the process further comprises:
(6) exchanging the headspace gas of the vial from step (5) with a perfluorocarbon gas.
(6) exchanging the headspace gas of the vial from step (5) with a perfluorocarbon gas.
25. A process according to Claim 24, wherein the perfluorocarbon gas is perfluoropropane.
26. A process according to Claim 25, wherein exchange of headspace gas is performed using a lyophilizing chamber.
27. A process according to Claim 24, wherein the process further comprises:
(7) sterilizing the vial from step (6).
(7) sterilizing the vial from step (6).
28. A process according to Claim 27, wherein in step (7), the vial is sterilized at about 126-130°C for 1 to 10 minutes.
29. A process for preparing a lipid blend, comprising:
(a) contacting at least two lipids with a first non-aqueous solvent;
(b) concentrating the solution to a thick gel;
(c) contacting the thick gel with a second non-aqueous solvent; and, (d) collecting the resulting solids.
(a) contacting at least two lipids with a first non-aqueous solvent;
(b) concentrating the solution to a thick gel;
(c) contacting the thick gel with a second non-aqueous solvent; and, (d) collecting the resulting solids.
30. A process according to Claim 29, wherein in step (a), the lipids are:
(i) 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine;
(ii)1,2-dipalmitoyl-sn-glycero-3-phosphotidic, mono sodium salt; and, (iii) N-(methoxypolyethylene glycol 5000 carbamoyl)-1,2-dipalmitoyl-sn-glycero-3-prosphatidylethanolamine, mono sodium salt.
(i) 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine;
(ii)1,2-dipalmitoyl-sn-glycero-3-phosphotidic, mono sodium salt; and, (iii) N-(methoxypolyethylene glycol 5000 carbamoyl)-1,2-dipalmitoyl-sn-glycero-3-prosphatidylethanolamine, mono sodium salt.
31. A process according to Claim 30, wherein in step (a), the first non-aqueous solvent is a mixture of methanol and toluene.
32. A process according to Claim 30, wherein in step (c), the second non-aqueous solvent is a methyl t-butyl ether.
33. A process according to Claim 30, wherein in step (a), the solution is warmed to a temperature sufficient to complete dissolution of the lipids into the solvent.
34. A process according to Claim 33, wherein in step (a), the solution is warmed to about 25 to 75°C.
35. A process according to Claim 30, wherein in step (d), the solids collected are washed with methyl t-butyl ether and dried in vacuo.
36. A phospholipid suspension, comprising:
(a) a lipid blend in an amount of about 0.75 - 1.0 mg/mL of suspension;
(b) sodium chloride in an amount of about 6.8 mg/mL of suspension;
(c) glycerin in an amount of about 0.1 mL/mL of suspension;
(d) propylene glycol in an amount of about 0.1 mL/mL of suspension; and (e) water;
wherein the suspension is prepared by the process, comprising:
(1) contacting a lipid blend with a non-aqueous solvent, whereby the lipid blend substantially dissolves in the non-aqueous solvent;
(2) contacting the solution from step (1) with an aqueous solution to form a lipid suspension;
(3) heating the lipid suspension from step (2) to a temperature about equal to or above the highest gel to liquid crystalline phase transition temperature of the lipids present in the suspension; and, (4) filtering the lipid suspension through a sterilizing filter.
(a) a lipid blend in an amount of about 0.75 - 1.0 mg/mL of suspension;
(b) sodium chloride in an amount of about 6.8 mg/mL of suspension;
(c) glycerin in an amount of about 0.1 mL/mL of suspension;
(d) propylene glycol in an amount of about 0.1 mL/mL of suspension; and (e) water;
wherein the suspension is prepared by the process, comprising:
(1) contacting a lipid blend with a non-aqueous solvent, whereby the lipid blend substantially dissolves in the non-aqueous solvent;
(2) contacting the solution from step (1) with an aqueous solution to form a lipid suspension;
(3) heating the lipid suspension from step (2) to a temperature about equal to or above the highest gel to liquid crystalline phase transition temperature of the lipids present in the suspension; and, (4) filtering the lipid suspension through a sterilizing filter.
37. A phospholipid suspension according to Claim 36, wherein the lipid blend, comprises:
(a) 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine;
(b) 1,2-dipalmitoyl-sn-glycero-3-phosphotidic, mono sodium salt; and, (c) N-(methoxypolyethylene glycol 5000 carbamoyl)-1,2-dipalmitoyl-sn-glycero-3-phosphatidylethanolamine, mono sodium salt.
(a) 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine;
(b) 1,2-dipalmitoyl-sn-glycero-3-phosphotidic, mono sodium salt; and, (c) N-(methoxypolyethylene glycol 5000 carbamoyl)-1,2-dipalmitoyl-sn-glycero-3-phosphatidylethanolamine, mono sodium salt.
38. A phospholipid suspension according to Claim 37, wherein the non-aqueous solvent is heated to a temperature of about 50 to 55°C prior to contacting with the lipid blend.
39. A phospholipid suspension according to Claim 37, wherein the ratio of lipid blend to non-aqueous solvent is about 10 mg/mL.
40. A phospholipid suspension according to Claim 37, wherein the aqueous solution is a saline, glycerin, and propylene glycol mixture.
41. A phospholipid suspension according to Claim 40, wherein 0.75 mg/mL of lipid blend are present.
42. A phospholipid suspension according to Claim 37, wherein the aqueous solution is heated to a temperature of about 50 to 55°C prior to contacting with the solution from step (1).
43. A phospholipid suspension according to Claim 37, wherein in step (3), the lipid suspension is heated to a temperature of at least about 67°C.
44. A phospholipid suspension according to Claim 43, wherein in step (4), two 0.2µm hydrophilic filters are used.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7133298P | 1998-01-14 | 1998-01-14 | |
US60/071,332 | 1998-01-14 | ||
PCT/US1999/000747 WO1999036104A2 (en) | 1998-01-14 | 1999-01-14 | Preparation of a lipid blend and a phospholipid suspension containing the lipid blend, and contrast agents based on these |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2317921A1 true CA2317921A1 (en) | 1999-07-22 |
CA2317921C CA2317921C (en) | 2011-03-22 |
Family
ID=22100659
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2317921A Expired - Lifetime CA2317921C (en) | 1998-01-14 | 1999-01-14 | Preparation of a lipid blend and a phospholipid suspension containing the lipid blend |
Country Status (31)
Country | Link |
---|---|
US (8) | US20010003580A1 (en) |
EP (2) | EP1027035A2 (en) |
JP (2) | JP5160702B2 (en) |
KR (1) | KR100711663B1 (en) |
CN (1) | CN1191822C (en) |
AR (1) | AR016444A1 (en) |
AT (1) | ATE447976T1 (en) |
AU (1) | AU746067C (en) |
BR (1) | BR9907066A (en) |
CA (1) | CA2317921C (en) |
DE (1) | DE69941634D1 (en) |
DK (1) | DK1419789T3 (en) |
EA (1) | EA002978B1 (en) |
EE (1) | EE04900B1 (en) |
ES (1) | ES2336669T3 (en) |
HK (1) | HK1064301A1 (en) |
HR (1) | HRP990012A2 (en) |
HU (1) | HUP0100206A3 (en) |
IL (2) | IL137018A0 (en) |
MY (1) | MY137255A (en) |
NO (1) | NO321866B1 (en) |
NZ (1) | NZ505082A (en) |
PH (1) | PH12012000094A1 (en) |
PL (1) | PL193672B1 (en) |
PT (1) | PT1419789E (en) |
SI (1) | SI1419789T1 (en) |
SK (1) | SK285333B6 (en) |
TW (1) | TWI242448B (en) |
UA (1) | UA75023C2 (en) |
WO (1) | WO1999036104A2 (en) |
ZA (1) | ZA99247B (en) |
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AU2006200015B8 (en) * | 1998-01-14 | 2008-02-21 | Dupont Pharmaceuticals Company | Preparation of a lipid blend and a phospholipid suspension containing a lipid blend, and contrast agents based on these |
US20010003580A1 (en) * | 1998-01-14 | 2001-06-14 | Poh K. Hui | Preparation of a lipid blend and a phospholipid suspension containing the lipid blend |
US6975924B2 (en) * | 1999-12-03 | 2005-12-13 | Baxter International Inc. | Method and apparatus for controlling the strategy of compounding pharmaceutical admixtures |
MXPA03008975A (en) * | 2001-04-03 | 2004-02-17 | Bristol Myers Squibb Pharma Co | Stabilization and terminal sterilization of phospholipid formulations. |
WO2003070285A1 (en) | 2002-02-19 | 2003-08-28 | Resolution Chemicals Limited | Solvent-based sterilisation of pharmaceuticals |
EP1590006B1 (en) * | 2003-02-04 | 2010-09-08 | Bracco Suisse SA | Ultrasound contrast agents and process for the preparation thereof |
CA2547024C (en) | 2003-12-22 | 2013-12-17 | Bracco Research Sa | Gas-filled microvesicle assembly for contrast imaging |
CN1321697C (en) * | 2003-12-23 | 2007-06-20 | 中国人民解放军军事医学科学院毒物药物研究所 | Ultrasound contrast medium composition with phospholipid as membrane material and its preparation method |
US7618651B2 (en) | 2004-06-24 | 2009-11-17 | Idexx Laboratories | Pharmaceutical compositions for drug delivery and methods of treating or preventing conditions using same |
US7854943B2 (en) | 2004-06-24 | 2010-12-21 | Idexx Laboratories | Phospholipid gel compositions for drug delivery and methods of treating conditions using same |
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JP4837663B2 (en) | 2004-08-18 | 2011-12-14 | ブラッコ・シュイス・ソシエテ・アノニム | Gas-filled microvesicle composition for contrast imaging |
US8017159B2 (en) * | 2005-11-16 | 2011-09-13 | Idexx Laboratories, Inc. | Phospholipid gel compositions for delivery of aptamers and methods of treating conditions using same |
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