# US 11,304,964 B2 · Bolaamphiphilic compounds, compositions and uses thereof

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- Number: US 11,304,964 B2
- Document ID: US11304964B2
- Status: Granted
- Kind: B2
- Application number: 14/328,280
- Filed: 2014-07-10
- Published: 2015-04-16
- Granted: 2022-04-19
- Earliest claimed: 2012-09-04
- Assignees: Lauren Sciences LLC
- Applicants: Lauren Sciences LLC
- Inventors: Charles Linder; Sarina Grinberg; Eliahu Heldman
- Web page: https://patentgrep.com/patent/US11304964B2

## CPC

- A61K 31/675: having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
- 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)}
- A61K 9/1075: {Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers (A61K9/0026 takes precedence)}
- A61K 47/18: Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- A61K 47/28: Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
- 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)

## Abstract

Bolaamphiphilic compounds are provided according to formula I: HG2-L1-HG1 I where HG1, HG2 and L1 are as defined herein. Provided bolaamphiphilic compounds and the pharmaceutical compositions thereof are useful for delivering HIV active drugs into animal or human brain.

## Claims

### Claim 1

A formulation containing vesicles comprising one or more bolaamphiphilic compounds, cholesteryl hemisuccinate, cholesterol, stearyl amine, and an active agent which is tenofovir or fosamprenavir ({[(2R,3S)-1-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-3-({[(3S)-oxolan-3-yloxy]carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid), wherein the pH has been adjusted to a pH of 7.5 or 8 using a buffer to maximize tenofovir encapsulation
wherein for 1 mL of formulation the components are: 10 mg GLH 19 and GLH 20 in a ratio of 2/1, 1 mg GLH-55b, 2.4 mg cholesteryl hemisuccinate, 1.6 mg cholesterol, 2.5 mg stearyl amine, and 5 mg tenofovir or fosamprenavir ({[(2R,3S)-1-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-3-({[(3S)-oxolan-3-yloxy]carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid);
and the buffer is a HEPES, wherein
GLH 19 is
wherein
HG is
each p1 and p2 is an integer from 1-400, and R7a is H or an acyl group.

### Claim 2 (depends on 1)

A formulation of claim 1 suitable for IV, IP, oral, or transdermal administration for delivery of the active agent above its therapeutic threshold of 100 ng/mL.

### Claim 3 (depends on 1)

A formulation of claim 1 suitable for IV, IP, oral, or transdermal administration for delivery of the active agent above its therapeutic threshold of 100 ng/100 mL.

### Claim 4 (depends on 1)

A formulation of claim 1 wherein for 1 mL of formulation the components are: 10 mg GLH 19 and GLH 20 in a ratio of 2/1, 1 mg GLH-55b, 2.4 mg cholesteryl hemisuccinate, 1.6 mg cholesterol, 2.5 mg stearyl amine, and 5 mg tenofovir; and the buffer is a HEPES buffer.

### Claim 5 (depends on 1)

A formulation of claim 1, wherein the pH has been adjusted to a pH of 7.5.