# US 11,078,222 B2 · Hydroxybenzoic acid derivatives, methods and uses thereof

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- Number: US 11,078,222 B2
- Document ID: US11078222B2
- Status: Granted
- Kind: B2
- Application number: 16/475,277
- Filed: 2017-12-29
- Published: 2019-10-31
- Granted: 2021-08-03
- Earliest claimed: 2016-12-29
- Assignees: Universidade Do Porto; Centro de Neurociencias e Biologia Celular
- Applicants: UNiVERSIDADE DO PORTO; Centro De NeurociêNcias E Biologia Celular
- Inventors: Maria Fernanda Martins Borges; Paulo Jorge Gouveia Simõës Da Silva Oliveira; José Carlos Santos Teixeira; Fernando Cagide Fagin; Ana Catarina Gomes Oliveira
- Web page: https://patentgrep.com/patent/US11078222B2

## CPC

- C07F 9/5442: {Aromatic phosphonium compounds (P-C aromatic linkage)}
- C07F 9/5456: {Arylalkanephosphonium compounds}
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 35/00: Antineoplastic agents
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present disclosure relates to the design and synthesis of new mitochondriotropic antioxidant compounds based on hydroxybenzoic acids and analogues. Furthermore, this disclosure is also related to the methods and uses of the hydroxybenzoic based derivatives and analogues, for example, in the field of human and animal diseases, for instance to treat mitochondrial dysfunction or mitochondrial deficiencies, and cosmetics, for instance to prevent or delay skin aging.

## Claims

### Claim 1

A compound of formula I
or a salt, tautomer, or stereoisomer thereof,
wherein
R′, R2, R3, R4, R5, R6 and R7 are independently selected from each other;
R′, R2, R3, R4 and R5 are selected from H, halogen, hydroxyl, methyl, methoxyl, amino, carboxylic acid, or nitro group;
R6 is a secondary amide or tertiary amide;
R7 is an alkyl chain, an alkenyl chain, an alkynyl chain, a substituted aryl, or a secondary amide;
Z−is an acceptable anion; and
wherein the alkyl chain, the alkenyl chain or the alkynyl chain is a C5-C30 chain.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound has the following formula:

### Claim 3 (depends on 1)

The compound of claim 1, wherein the compound has the following formula:

### Claim 4 (depends on 1)

The compound of claim 1, wherein
R7 is a secondary amide of R8-(C=O)NH-R9 amide,
R8 and R9 are independently selected from each other and
R8 and R9 are an alkyl chain, an alkenyl chain, an alkynyl chain or an substituted aryl.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the substituted aryl is an alkane-aryl substituted, alkene-aryl substituted, or alkyne-aryl substituted.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the alkyl chain, the alkenyl chain or the alkynyl chain is a C6-C14 chain.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R1 and R5 are H.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R2 and R3 are OH.

### Claim 9 (depends on 1)

The compound of claim 1, wherein R4 is H or OH.

### Claim 10 (depends on 1)

The compound of claim 1, wherein R7 is a C6 alkyl chain.

### Claim 11 (depends on 4)

The compound of claim 4 wherein R8 and R9 are independently of each other a C5 alkyl chain or a C6 alkyl chain.

### Claim 12 (depends on 1)

The compound of claim 1, wherein the compound is 6-(3,4-dihydroxybenzamido)hexyltriphenylphosphonium bromide.

### Claim 13 (depends on 1)

The compound of claim 1, wherein the compound is 6-(3,4,5-trihydroxybenzamido)hexyltriphenylphosphonium bromide.

### Claim 14 (depends on 1)

The compound of claim 1, wherein the compound is 5-(6-(3,4,5-trihydroxybenzamido)hexylamino) carbonylpentyl]triphenylphosphonium bromide.

### Claim 15 (depends on 1)

A composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier, adjuvant, excipient, or diluent or mixtures thereof.

### Claim 16 (depends on 15)

The composition of claim 15, wherein the pharmaceutically acceptable carrier is saline, gum acacia, gelatin, starch paste, talc, keratin, colloidal silica, urea or mixtures thereof.

### Claim 17 (depends on 15)

The composition of claim 15, wherein the adjuvant is oil-in-water emulsion adjuvant, aluminium adjuvant, a TLR-4 ligand, a saponin, or mixtures thereof.

### Claim 18 (depends on 15)

The composition of claim 15, wherein the excipient is glucose, lactose, sucrose, glycerol monostearate, sodium chloride, glycerol, propylene, glycol, water, ethanol or mixtures thereof.