Synthetic phospholipid compounds

• US 4,534,899 A
• Filed: 03/07/1983
• Issued: 08/13/1985
• Est. Priority Date: 07/20/1981
• Status: Expired due to Term

• Current Assignee: Surfactant Technologies, Inc.
• Original Assignee: Lipid Specialties, Inc.
• Inventors: Sears, Barry D.
• Primary Examiner(s): Waltz, Thomas A.
• Application Number:
  US06/472,481
• Time in Patent Office: 890 Days
• Field of Search: 260/403, 260/944
• US Class Current: 554/80
• CPC Class Codes: A61K 47/24 containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
• CPC Class Codes: A61K 9/0019 Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner non-active ingredients are additionally classified in A61K47/00
• CPC Class Codes: A61K 9/127 Liposomes
• CPC Class Codes: A61K 9/1271 Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers liposome as conjugate A61K47/6911
• CPC Class Codes: C07F 9/10 Phosphatides, e.g. lecithin
• CPC Class Codes: C08G 65/3356 having nitrogen in addition to phosphorus

Abstract

Synthetic phospholipid compounds and their method of preparation, which compounds are phosphatidylethanolamine polycarboxyl polyalkylene glycols and are prepared by the reaction of a phosphatidylethanolamine, a polycarboxylic acid, such as succinic or glutaryl anhydride, and a polyalkylene glycol, such as polyethylene glycol.

Claims

1. A synthetic phospholipid compound having the structural formula:

##STR3## wherein R₁ and R₂ represent hydrogen or organic acyl radicals;

R₃ represents a C₂ to C₄ alkylene radical;

X represents hydrogen or an alkyl radical;

R₄ represents a C₂ to C₁₀ alkylene radical;

R₅ represents an organic linking radical;

R₆ represents hydrogen or a lower alkyl radical; and

n represents a number of from 0 to 200.

2. The phospholipid compound of claim 1 wherein R₁ and R₂ represent C₂ to C₂₀ fatty-acid radicals.

3. The phospholipid compound of claim 1 wherein R₅ represents a polymethylene radical.

4. The phospholipid compound of claim 3 wherein R₅ represents a C₁ to C₄ methylene radical.

5. The phospholipid compound of claim 1 wherein n represents a number of from 2 to 100.

6. The phospholipid compound of claim 1 wherein R₁ and R₂ are organic radicals derived from soybeans.

7. The phospholipid compound of claim 1 wherein R₄ represents an ethylene radical.

8. The phospholipid compound of claim 1 wherein R₃ represents an ethylene radical.

9. The phospholipid compound of claim 1 wherein R₆ represents a methyl radical.

10. The phospholipid compound of claim 1 wherein the molecular weight is from about 150 to 3000.

11. The synthetic phospholipid compound having the structural formula:

##STR4## wherein R₁ and R₂ represent C₂ to C₂₀ hydrocarbon organic acyl radicals;

X represents hydrogen or a methyl radical;

m represents a number of from 1 to 4; and

n represents a number of from 0 to 200.

12. The synthetic phospholipid compound which is a phosphatidylethanolamine succinyl polyethylene glycol compound.

13. The synthetic phospholipid compound which is a phosphatidylethanolamine glutaryl polyethylene glycol compound.

14. The synthetic phospholipid compound which is a phosphatidylethanolamine di or tri carboxyl polyethylene or polypropylene glycol compound.

15. The synthetic phospholipid compound of claim 14 wherein the compound is a polyethylene or polypropylene monomethyl ether compound.

16. The synthetic phospholipid compound of claim 14 wherein the carboxyl is a C₃ -C₆ carboxyl.

17. The synthetic phospholipid compound soy phosphatidylethanolamine succinyl polyethylene glycol monomethyl ether.

18. The synthetic phospholipid compound soy phosphatidylethanolamine glutaryl polyethylene glycol monomethyl ether.