# US 10,479,752 B2 · Deuterated tetramethyl dioic acids, compositions comprising them and uses thereof

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- Number: US 10,479,752 B2
- Document ID: US10479752B2
- Status: Granted
- Kind: B2
- Application number: 14/363,912
- Filed: 2012-12-06
- Published: 2014-12-18
- Granted: 2019-11-19
- Earliest claimed: 2011-12-08
- Assignees: Syndromex Ltd.
- Applicants: Syndromex Ltd.
- Inventors: Jacob Bar-Tana
- Web page: https://patentgrep.com/patent/US10479752B2

## CPC

- C07C 55/02: Dicarboxylic acids
- A61K 9/10: Dispersions; Emulsions
- A61K 47/38: Cellulose; Derivatives thereof
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/06: Antihyperlipidemics
- A61P 3/08: for glucose homeostasis (pancreatic hormones A61P5/48)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- C07B 59/001: {Acyclic or carbocyclic compounds}
- C07C 51/02: from salts of carboxylic acids
- C07C 51/09: from carboxylic acid esters or lactones
- C07C 51/41: Preparation of salts of carboxylic acids ({C07C51/093 - C07C51/34 take precedence} preparation of soap C11D)
- C07C 67/32: Decarboxylation
- C07C 67/347: by addition to unsaturated carbon-to-carbon bonds
- C07C 69/34: Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C07C: ACYCLIC OR CARBOCYCLIC 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

This invention relates to deuterated tetramethyl dioic acids, compositions comprising them and uses thereof in the treatment of Metabolic Syndrome and any diseases, disorders or symptoms associated therewith.

## Claims

### Claim 1

A deuterium enriched composition of a compound of general formula (I), including any salts, esters or anhydrides thereof:
wherein
L is a straight or branched C8-C16 alkylene; optionally interrupted by at least one moiety selected from O, S, NH, C5-C10cycloalkylene, C5-C10cycloheteroalkylene, C6-C18 arylene, C6-C18 heteroarylene;
each of R1-R8 is independently selected from H, D, CH3 and CD3; wherein at least one of R1-R8 is D or CD3; and
the abundance of deuterium at any D- or CD3-occupied position in the compound of the composition is substantially greater than the 0.015% natural abundance of deuterium.

### Claim 2 (depends on 1)

A deuterium enriched composition according to claim 1, wherein said compound of general formula (I), including any salts, esters or anhydrides thereof is:
wherein
L is a straight or branched C8-C16 alkylene; optionally interrupted by at least one moiety selected from O, S, NH, C5-C10cycloalkylene, C5-C10cycloheteroalkylene, C6-C18 arylene, C6-C18 heteroarylene;
each of R1-R4 is independently H or D;
each of R5-R8 is independently CH3 or CD3;
wherein when R1-R4 are H, at least one of R5-R8 is CD3; or when R5-R8 are CH3, at least one of R1-R4 is D.

### Claim 3 (depends on 1)

A deuterium enriched composition according to claim 1, wherein said compound of general formula (I), including any salts, esters or anhydrides thereof is:
wherein
L is a straight or branched C8-C16 alkylene; optionally interrupted by at least one moiety selected from O, S, NH, C5-C10 cycloalkylene, C5-C10 cycloheteroalkylene, C6-C18 arylene, C6-C18 heteroarylene;
each of R1-R4 is independently CH3 or CD3, and at least one of R1-R4 is CD3; and
each of R5-R8 is independently H.

### Claim 4 (depends on 1)

A deuterium enriched composition according to claim 1, wherein, in said compound, at least one of R1-R4 is D.

### Claim 5 (depends on 1)

A deuterium enriched composition according to claim 1, wherein, in said compound, at least one of R5-R8 is CD3.

### Claim 6 (depends on 1)

A deuterium enriched composition according to claim 1, wherein, in said compound, at least one of R1-R4 is CD3.

### Claim 7 (depends on 1)

A deuterium enriched composition according to claim 1, wherein, in said compound, at least one of R5-R8 is D.

### Claim 8 (depends on 1)

A deuterium enriched composition according to claim 1, wherein, in said compound, L is any one of —(CH2)10— and —(CH2)12—.

### Claim 9 (depends on 1)

A deuterium enriched composition according to claim 1, wherein, in said compound, at least one of R1-R4 is D and at least one of R5-R8 is CD3.

### Claim 10 (depends on 1)

A deuterium enriched composition according to claim 1, wherein, in said compound, at least one of R1-R4 is CD3 and at least one of R5-R8 is D.

### Claim 11 (depends on 1)

A deuterium enriched composition according to claim 1, wherein said compound is:
Compound
R1 = R2 = R3 = R4
R5 = R6 = R7 = R8
II
D
CH3
III
H
CD3
IV
D
CD3.

### Claim 12 (depends on 1)

A deuterium enriched composition according to claim 1, wherein said compound is:
Compound
R1 = R2
R3 = R4
R5 = R6
R7 = R8
V
D
H
CH3
CH3
VI
D
H
CD3
CH3
VII
D
H
CH3
CD3
VIII
D
H
CD3
CD3
IX
D
D
CD3
CH3.

### Claim 13 (depends on 1)

A deuterium enriched composition according to claim 1, wherein said compound is:
Compound
R1 = R3
R2 = R4
R5 = R6
R7 = R8
X
D
H
CH3
CH3
XI
D
H
CD3
CH3
XII
D
H
CD3
CD3.

### Claim 14 (depends on 1)

A deuterium enriched composition according to claim 1, wherein said compound is:
Compound
R1 = R3
R2 = R4
R5 = R7
R6 = R8
XIII
D
H
CH3
CH3.

### Claim 15 (depends on 1)

A deuterium enriched composition according to claim 1, wherein said compound is:
Compound
R1 = R2 = R3 = R4
R5 = R6 = R7 = R8
XIV
CD3
H.

### Claim 16 (depends on 1)

A deuterium enriched composition according to claim 1, wherein said compound is:
Compound
R1 = R2
R3 = R4
R5 = R6
R7 = R8
XV
CD3
CH3
H
H.

### Claim 17 (depends on 1)

A deuterium enriched composition according to claim 1, wherein said compound is:
Compound
R1 = R3
R2 = R4
R5 = R6
R7 = R8
XVI
CD3
CH3
H
H.

### Claim 18 (depends on 1)

A composition comprising a deuterium enriched composition of a compound according to claim 1 or any salts, esters or anhydrides thereof.

### Claim 19 (depends on 1)

A method of treating a disease, condition, symptom or disorder associated with Metabolic Syndrome in a subject, said method comprising administering to said subject an effective amount of at least one deuterium enriched composition as defined in claim 1.

### Claim 20 (depends on 19)

A method according to claim 19, wherein said disease, condition or disorder associated with Metabolic Syndrome is selected from dyslipidemia, diabetes, obesity, cancer, hypertension and neurodegeneration.

### Claim 21 (depends on 1)

A deuterium enriched composition of a compound according to claim 1, wherein said compound is 2,2,15,15-tetramethyl(D12)-hexadecanedioic acid or any salt, ester or anhydride thereof.

### Claim 22 (depends on 1)

A deuterium enriched composition of a compound according to claim 1, wherein said compound is 2,2,17,17-tetramethyl(D12)-octadecanedioic acid or any salt, ester or anhydride thereof.

### Claim 23

An isolated deuterium enriched compound of general formula (I):
wherein each of R1-R4 is independently CD3 and each of R5-R8 is independently hydrogen and L is a straight C12 alkyl chain, which is 2,2,15,15-tetramethyl(D12)-hexadecanedioic acid or any salt, ester or anhydride thereof.

### Claim 24

An isolated deuterium enriched compound of general formula (I):
wherein each of R1-R4 is independently CD3 and each of R5-R8 is independently hydrogen and L is a straight C14 alkyl chain, which is 2,2,17,17-tetramethyl(D12)-octadecanedioic acid or any salt, ester or anhydride thereof.

### Claim 25 (depends on 1)

A deuterium-enriched composition according to claim 1 wherein D at a specified position in the compound indicates at least 50.1% incorporation of deuterium at that position in the composition.