# US 2014/0194536 A1 · Low-viscosity liquid crystal compound

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- Number: US 2014/0194536 A1
- Document ID: US20140194536A1
- Status: Published application
- Kind: A1
- Application number: 14/193,184
- Filed: 2014-02-28
- Published: 2014-07-10
- Earliest claimed: 2009-12-25
- Assignees: Chemgenesis Incorporated
- Applicants: Chemgenesis Incorporated
- Inventors: Yutaka Ikeda; Jun Yamashita; Ichiro Hijikuro; Satoshi Imuta; Yasuhiro Hiroki; Takashi Takahashi
- Web page: https://patentgrep.com/patent/US20140194536A1

## CPC

- A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- 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 9/0024: {Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue (compositions for intravenous administration, normal injectable solutions or dispersions for, e.g. subcutaneous administration A61K9/0019; brain implants A61K9/0085; (coated) prostheses, catheters or stents A61L)}
- A61K 47/08: containing oxygen, {e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides}
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/22: Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- A61K 47/26: Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
- C07H 15/10: containing unsaturated carbon-to-carbon bonds
- C09K 19/06: Non-steroidal liquid crystal compounds
- 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)
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present invention relates to a liquid crystal compound that can be used as a base for injection formulations. The present invention provides an amphipathic compound having the following general formula (I): wherein X and Y each denotes a hydrogen atom or together denote an oxygen atom, n denotes an integer from 0 to 2, m denotes the integer 1 or 2, and R denotes a hydrophilic group generated by removal of one hydroxyl group from any one selected from the group consisting of glycerol, erythritol, pentaerythritol, diglycerol, triglycerol, xylose, sorbitol, ascorbic acid, glucose, galactose, mannose, dipentaerythritol, maltose, mannitol, and xylitol; as well as a base for injection formulations and depot formulation comprising the same.

## Claims

### Claim 1

An amphipathic compound having the following general formula (I):
wherein X and Y each denotes a hydrogen atom or together denote an oxygen atom, n denotes the integer 0, m denotes the integer 1 or 2, and R denotes a hydrophilic group generated by removal of one hydroxyl group from any one selected from the group consisting of glycerol, erythritol, pentaerythritol, diglycerol, triglycerol, xylose, sorbitol, ascorbic acid, glucose, galactose, mannose, dipentaerythritol, maltose, mannitol, and xylitol.

### Claim 2 (depends on 1)

The compound according to claim 1, which has viscosity of 11.0 Pa·s or less as determined at 25° C.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein X and Y together denote an oxygen atom, and R denotes a hydrophilic group generated by removal of one hydroxyl group from glycerol or diglycerol.

### Claim 4 (depends on 3)

The compound according to claim 3, wherein the compound is selected from the group consisting of:
mono-O-(3,7,11,15-tetramethylhexadec-2-enoyl)glycerol,
mono-O-(3,7,11,15-tetramethylhexadec-2-enoyl)diglycerol,
mono-O-(3,7,11-trimethyldodec-2-enoyl)glycerol, and
mono-O-(3,7,11-trimethyldodec-2-enoyl)diglycerol.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein R denotes a hydrophilic group generated by removal of one hydroxyl group from any one selected from the group consisting of erythritol, pentaerythritol, triglycerol, xylose, sorbitol, ascorbic acid, glucose, galactose, mannose, dipentaerythritol, maltose, mannitol, and xylitol.

### Claim 6 (depends on 5)

The compound according to claim 5, wherein the compound is selected from the group consisting of:
mono-O-(3,7,11,15-tetramethylhexadec-2-enoyl)erythritol,
mono-O-(3,7,11,15-tetramethylhexadec-2-enoyl)pentaerythritol,
1-O-(3,7,11,15-tetramethylhexadec-2-enyl)-D-xylopyranoside,
mono-O-(3,7,11,15-tetramethylhexadec-2-enyl)erythritol,
mono-O-(3,7,11,15-tetramethylhexadec-2-enyl)pentaerythritol,
mono-O-(3,7,11-trimethyldodec-2-enoyl)erythritol,
mono-O-(3,7,11-trimethyldodec-2-enoyl)pentaerythritol,
1-O-(3,7,11-trimethyldodec-2-enyl)-D-xylopyranoside,
mono-O-(3,7,11-trimethyldodec-2-enyl)erythritol, and
mono-O-(3,7,11-trimethyldodec-2-enyl)pentaerythritol.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein the compound is:
mono-O-(3,7,11-trimethyldodec-2-enyl)glycerol, or
mono-O-(3,7,11-trimethyldodec-2-enyl)diglycerol.

### Claim 8 (depends on 1)

A base for injection formulations, which comprises at least one type of the compound according to claim 1.

### Claim 9 (depends on 8)

A depot formulation, which comprises the base according to claim 8.

### Claim 10 (depends on 1)

A composition comprising the compound according to claim 1 and an active ingredient.

### Claim 11 (depends on 10)

The composition according to claim 10, wherein the composition further comprises an aqueous medium, and said amphipathic compound forms a non-lamellar liquid crystal in the composition.

### Claim 12 (depends on 10)

A method for administering an active ingredient to a subject, comprising administering the composition according to claim 10, wherein said amphipathic compound forms a non-lamellar liquid crystal in a living body of the subject.

### Claim 13 (depends on 11)

A method for administering an active ingredient to a subject, comprising administering the composition according to claim 11, wherein said amphipathic compound forms a non-lamellar liquid crystal in a living body of the subject.