# US 11,026,910 B2 · α- and γ-truxillic acid derivatives and pharmaceutical compositions thereof

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- Number: US 11,026,910 B2
- Document ID: US11026910B2
- Status: Granted
- Kind: B2
- Application number: 16/276,920
- Filed: 2019-02-15
- Published: 2019-07-04
- Granted: 2021-06-08
- Earliest claimed: 2012-07-20
- Assignees: The Research Foundation for The State University of New York
- Applicants: The Research Foundation for The State University of New York
- Inventors: Iwao Ojima; Dale Deutsch; Martin Kaczocha; William T. Berger; Robert Rizzo; Trent E. Balius
- Web page: https://patentgrep.com/patent/US11026910B2

## CPC

- A61K 31/216: of acids having aromatic rings, e.g. benactizyne, clofibrate
- A61K 31/194: having two or more carboxyl groups, e.g. succinic, maleic or phthalic acid
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- C07C 67/48: Separation; Purification; Stabilisation; Use of additives
- C07C 69/753: of polycyclic acids
- C07C 69/757: having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] in the acid moiety
- C07C 69/76: Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C 211/58: Naphthylamines; N-substituted derivatives thereof
- C07C 233/11: with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
- C07C 233/58: having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C 235/38: having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C 235/40: having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- G01N 33/566: using specific carrier or receptor proteins as ligand binding reagents {where possible specific carrier or receptor proteins are classified with their target compounds}
- G01N 33/68: involving proteins, peptides or amino acids {(involving lipoproteins G01N33/92)}
- C07B 2200/07: Optical isomers
- C07C 2601/04: with a four-membered ring
- G01N 2333/47: Assays involving proteins of known structure or function as defined in the subgroups
- G01N 2500/04: Screening involving studying the effect of compounds C directly on molecule A (e.g. C are potential ligands for a receptor A, or potential substrates for an enzyme A)
- G01N 2500/20: cell-free systems
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present invention provides a compound, and method of inhibiting the activity of a Fatty Acid Binding Protein (FABP) comprising contacting the FABP with a compound, having the structure:

## Claims

### Claim 1

A mixture of compounds having the structure:
wherein the mixture is enantiomerically enriched in a compound having the structure:
wherein
one of R1 or R2 is —C(═O)OR13,
wherein R13 is substituted C1-10 alkyl, C2-10 alkenyl or C2-10 alkynyl; and
the other of R1 or R2 is —C(═O)OH,
wherein the substituted C1-10 alkyl is substituted with halogen, alkoxy, heteroaryloxy, sulfonyl, nitro, mercapto, sulfanyl, cyano, amino, carbamoyl, carboxyl or acyl;
R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 are each independently, H, halogen, —NO2, —CN, —NHR15, —OR15 or CF3;
wherein R15 is H, C1-10 alkyl, C2-10 alkenyl or C2-10 alkynyl;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The mixture of claim 1, wherein the mixture is enriched in a compound having the structure:
wherein
one of R1 or R2 is —C(═O)OR13,
wherein R13 is substituted C1-10 alkyl, C2-10 alkenyl or C2-10 alkynyl; and
the other of R1 or R2 is —C(═O) OH,
wherein the substituted C1-10 alkyl is substituted with halogen, alkoxy, heteroaryloxy, sulfonyl, nitro, mercapto, sulfanyl, cyano, amino, carbamoyl, carboxyl or acyl;
R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 are each independently, H, halogen, —NO2, —CN, —NHR15, —OR15, CF3;
wherein R15 is H, C1-10 alkyl, C2-10 alkenyl or C2-10 alkynyl;
or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

The mixture of claim 1, wherein the mixture is enriched in a compound having the structure:
wherein
one of R1 or R2 is —C(═O)OR13,
wherein R13 is substituted C1-10 alkyl, C2-10 alkenyl or C2-10 alkynyl; and
the other of R1 or R2 is —C(═O) OH,
wherein the substituted C1-10 alkyl is substituted with halogen, alkoxy, heteroaryloxy, sulfonyl, nitro, mercapto, sulfanyl, cyano, amino, carbamoyl, carboxyl or acyl;
R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 are each independently, H, halogen, —NO2, —CN, —NHR15, —OR15, CF3;
wherein R15 is H, C1-10 alkyl, C2-10 alkenyl or C2-10 alkynyl;
or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

The mixture of claim 1, wherein the mixture is enriched in a compound having the structure of:
or a pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 1)

A pharmaceutical composition comprising the mixture of claim 1 and a pharmaceutically acceptable carrier.

### Claim 6 (depends on 1)

A method of inhibiting the activity of a Fatty Acid Binding Protein (FABP) comprising contacting the FABP with the mixture of claim 1.

### Claim 7 (depends on 6)

The method of claim 6, wherein the mixture inhibits binding of an FABP ligand to the FABP; or wherein the FABP ligand is an endocannabinoid ligand; or wherein the FABP ligand is anandamide (AEA) or 2-arachidonoylglycerol (2-AG).