# US 9,643,912 B2 · Fatty alcohol esters of hydroxycarboxylic acids

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- Number: US 9,643,912 B2
- Document ID: US9643912B2
- Status: Granted
- Kind: B2
- Application number: 14/939,422
- Filed: 2015-11-12
- Published: 2016-03-03
- Granted: 2017-05-09
- Earliest claimed: 2010-09-17
- Assignees: Chemsmart, LLC
- Applicants: Chemsmart, LLC
- Inventors: Joseph P. St. Laurent; Scott A. Goodrich; Gerald S. Jones, Jr.
- Web page: https://patentgrep.com/patent/US9643912B2

## CPC

- C07C 69/68: Lactic acid esters
- C08G 65/3322: {acyclic}
- C12P 7/62: Carboxylic acid esters
- C12Y 301/01003: Triacylglycerol lipase (3.1.1.3)
- C07B 2200/07: Optical isomers
- Y02P 20/52: using catalysts, e.g. selective catalysts
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- C12Y: ENZYMES
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Described herein are compositions (e.g., a pharmaceutical composition) and compounds of formula I, methods of making compounds of formula (I) and their use in the treatment and/or prevention of diseases and disorders.

## Claims

### Claim 1

A composition configured for topical administration, comprising a compound of formula (I):
wherein
R1 is a C12 alkyl;
n is an integer from 4 to 10; and
R2 is hydrogen, alkyl, aryl, heteroaryl, or heterocyclyl;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The composition of claim 1, wherein R2 is alkyl.

### Claim 3 (depends on 2)

The composition of claim 2, wherein R2 is C1-4 alkyl.

### Claim 4 (depends on 1)

The composition of claim 1, wherein R2 is aryl.

### Claim 5 (depends on 1)

The composition of claim 1, wherein when R2 is not hydrogen, the compound of formula (I) is a racemic mixture of a compound of formula (I).

### Claim 6 (depends on 1)

The composition of claim 1, wherein when R2 is not hydrogen, the compound of formula (I) is at least 90% enantiomeric excess of the R stereoisomer.

### Claim 7 (depends on 1)

The composition of claim 1, wherein when R2 is not hydrogen, the compound of formula (I) is at least 90% enantiomeric excess of the S stereoisomer.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the compound of formula (I) is represented by the following formula:
wherein n is 4.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the compound of formula (I) is represented by the following formula:
wherein n is 4.

### Claim 10 (depends on 1)

The composition of claim 1, wherein the compound of formula (I) is represented by the following formula:
wherein n is 4.

### Claim 11 (depends on 1)

The composition of claim 1, wherein the composition is a gel.

### Claim 12

A composition configured for topical administration, comprising a compound of formula (I):
wherein
R1 is a C8-35 alkyl;
n is an integer from 4 to 10; and
R2 is hydrogen, alkyl, aryl, heteroaryl, or heterocyclyl;
or a pharmaceutically acceptable salt thereof.

### Claim 13 (depends on 12)

The composition of claim 12, wherein R1 is a C8-25 alkyl group.

### Claim 14 (depends on 13)

The composition of claim 13, wherein R1 is a C10-20 alkyl group.

### Claim 15 (depends on 14)

The composition of claim 14, wherein R1 is a C10-15 alkyl group.

### Claim 16 (depends on 12)

The composition of claim 12, wherein R2 is alkyl.

### Claim 17 (depends on 16)

The composition of claim 16, wherein R2 is C1-4 alkyl.

### Claim 18 (depends on 12)

The composition of claim 12, wherein R2 is aryl.

### Claim 19 (depends on 16)

The composition of claim 16, wherein R2 is aralkyl.

### Claim 20 (depends on 12)

The composition of claim 12, wherein when R2 is not hydrogen, the compound of formula (I) is a racemic mixture of a compound of formula (I).

### Claim 21 (depends on 12)

The composition of claim 12, wherein when R2 is not hydrogen, the compound of formula (I) is at least 90% enantiomeric excess of the R stereoisomer.

### Claim 22 (depends on 12)

The composition of claim 12, wherein when R2 is not hydrogen, the compound of formula (I) is at least 90% enantiomeric excess of the S stereoisomer.

### Claim 23 (depends on 12)

The composition of claim 12, wherein the composition is a gel.