Synthetic phosphatidyl cholines useful in forming liposomes

• US 4,485,045 A
• Filed: 05/26/1982
• Issued: 11/27/1984
• Est. Priority Date: 07/06/1981
• Status: Expired due to Fees

• Current Assignee: Research Corporation
• Original Assignee: Research Corporation
• Inventors: Regen, Steven L.
• Primary Examiner(s): Lovering, Richard D.
• Application Number:
  US06/382,296
• Time in Patent Office: 916 Days
• Field of Search: 260/403, 424/199
• US Class Current: 554/80
• CPC Class Codes: A61K 9/1273 Polymersomes; Liposomes with polymerisable or polymerised bilayer-forming substances polymers grafted or coated on phosphatidyl liposomes A61K9/1271, on non-phosphatidyl liposomes A61K9/1272
• CPC Class Codes: C07F 9/10 Phosphatides, e.g. lecithin
• CPC Class Codes: C08F 30/02 containing phosphorus
• CPC Class Codes: Y10T 428/2984 Microcapsule with fluid core [includes liposome]
• CPC Class Codes: Y10T 428/2987 Addition polymer from unsaturated monomers only
• CPC Class Codes: Y10T 428/31913 Monoolefin polymer

Abstract

Lower-ω-alkenoyloxy-long chain alkanoic anhydrides are synthesized from the ω-hydroxyalkanoic acids and are condensed with glycerophosphatidyl cholines to prepare alkenoyloxyalkanoic esters of glycerophosphatidyl cholines. These are used to make vesicles which are then polymerized in situ. These vesicles show improved stability and the rate of leakage of entrapped active ingredients such as drugs can be controlled. They are also used to form a hydrophyllic monolayer on polyethylene.

Claims

1. A compound of the structure ##STR7## B and C are each --CO--R₁ or --CO--R₂ ;

in which --CO--R₁ is a fatty acid acyl group of at least 6 carbons, and --CO--R₂ is --CO--(CH₂)_n --O--CO--CR₃ ═

CHR₄ in which n is greater than 4, and R₃ and R₄ are each hydrogen or methyl;

R₅ is hydrogen or --CH₂ --D, wherein D is --CO--R₂ and at least one of B, C, and D is present in the compound as --CO--R₂.

2. A compound of claim 1 in which B is --CO--R₁ and C is --CO--R₂.

3. A compound of claim 2 in which --CO--R₁ is --CO--(CH₂)₁₅ --CH₃ and --CO--R₂ is --CO--(CH₂)₁₁ --O--CO--C(CH₃)═

CH₂.

4. A compound of claim 1 in which B and C are both --CO--R₂.

5. A compound of claim 4 in which --CO--R₂ is --CO--(CH₂)₁₁ --O--CO--C(CH₃)═

CH₂.