# US 5,705,655 A · Amphiphilic nitrogen containing imidazolinium derivative compounds and uses

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- Number: US 5,705,655 A
- Document ID: US5705655A
- Status: Granted
- Kind: A
- Application number: 08/247,963
- Filed: 1994-05-24
- Granted: 1998-01-06
- Earliest claimed: 1992-12-17
- Assignees: Megabios Corporation
- Inventors: Timothy D. Heath; Igor Solodin
- Web page: https://patentgrep.com/patent/US5705655A

## CPC

- C07D 233/56: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- A61K 9/1272: comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers (lipids as modifying agents {A61K47/543})
- A61K 47/6801: {Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent}
- C07C 279/08: being further substituted by singly-bound oxygen atoms
- C07F 9/10: Phosphatides, e.g. lecithin
- C12N 15/88: using microencapsulation, e.g. using {amphiphile} liposome vesicle
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)

## Abstract

Amphiphiles containing an imidazdinium ring system are provided that are non-toxic to the host mammal. The amphiphiles are used to produce liposomes useful as carriers for delivering macromolecules intracellularly.

## Claims

### Claim 1

A nitrogen-containing amphiphile of the formula: ##STR6## wherein each R and R.sub.1 independently is a straight-chain, aliphatic hydrocarbyl group of 11 to 29 carbon atoms inclusive.

### Claim 2 (depends on 1)

The amphiphile of claim 1 wherein R independently has from 13 to 23 carbon atoms inclusive.

### Claim 3 (depends on 1)

The amphiphile of claim 1 wherein R is heptadecyl or R.sub.1 is octadecyl.

### Claim 4 (depends on 1)

The amphiphile of claim 1 wherein R is tridecyl or R.sub.1 is tetradecyl.

### Claim 5 (depends on 1)

The amphiphile of claim 1 wherein R is pentadecyl or R.sub.1 is hexadecyl.

### Claim 6 (depends on 1)

The amphiphile of claim 1 wherein R is heptadecenyl or R.sub.1 is octadecyl.

### Claim 7 (depends on 1)

The amphiphile of claim 1 wherein said amphiphile is 1-›9-(Z)-octadecenoyloxyethyl!-2-›8-(Z)-heptadecenyl!-3-hydroxyethylimidaz olinium.

### Claim 8

A method for synthesizing an imidazolinium ion, which comprises:
heating a precursor compound of formula ##STR7## in an organic solvent at a temperature above the boiling point of water, wherein each of R and R.sub.1 independently represents an organic group such that said precursor compound is soluble in said solvent and said R and R.sub.1 are stable against reaction in said solvent at said temperature.

### Claim 9 (depends on 8)

The method of claim 8, wherein said solvent is a protic solvent.

### Claim 10 (depends on 8)

The method of claim 8, wherein said heating occurs in the presence of an acid.

### Claim 11 (depends on 10)

The method of claim 10, wherein said acid is HCl.