# US 9,744,180 B2 · Pharmaceutical formulations containing mitochondrially targeted antioxidants

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- Number: US 9,744,180 B2
- Document ID: US9744180B2
- Status: Granted
- Kind: B2
- Application number: 14/803,789
- Filed: 2014-01-21
- Published: 2016-08-25
- Granted: 2017-08-29
- Earliest claimed: 2013-01-22
- Assignees: Mitotech SA
- Applicants: Mitotech SA
- Inventors: Maxim V Skulachev; Vladimir P. Skulachev; Egor Y Plotnikov; Dmitry B Zorov; Roman A Zinovkin; Alexander N Lukashev; Maxim V Egorov; Maxim L Lovat; Anton Petrov
- Web page: https://patentgrep.com/patent/US9744180B2

## CPC

- A61K 31/662: Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
- A61K 31/352: condensed with carbocyclic rings, e.g. methantheline {(cannabinoids A61K31/658)}
- A61K 31/4375: the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
- A61K 31/4745: condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines (yohimbine derivatives, vinblastine A61K31/475; ergoline derivatives A61K31/48)
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 1/18: for pancreatic disorders, e.g. pancreatic enzymes
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 13/12: of the kidneys
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/04: Antibacterial agents
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 39/06: Free radical scavengers or antioxidants
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C09B 11/24: Phthaleins containing amino groups {; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes}
- C09B 57/00: Other synthetic dyes of known constitution
- C09B 69/001: {Dyes containing an onium group attached to the dye skeleton via a bridge}
- 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
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)

## Abstract

The present disclosure provides methods of preventing activation of neutrophils with mitochondrially targeted antioxidants. Also disclosed are methods of preventing or treating different inflammatory diseases and inflammation-related conditions with MTAs.

## Claims

### Claim 1

A method of treatment of an inflammatory disorder selected from the group consisting of acute pyelonephritis, hepatitis, and pancreatitis, the method comprising treating a subject having the inflammatory disorder with one or more mitochondrially targeted antioxidant having the structure:
wherein:
A is an effector moiety having a following structure:
and reduced forms thereof, wherein:
m is an integer from 1 to 3;
each Y is independently selected from the group consisting of:
lower alkyl;
lower alkoxy; or
two adjacent Y groups, together with carbon atoms to which they are attached, form a following structure:
and reduced forms thereof; wherein:
R1 and R2 may be the same or different and are each independently lower alkyl or lower alkoxy;
L is a linker group, comprising:
a) a straight or branched hydrocarbon chain which can be optionally substituted by one or more substituents and optionally contains one or more double or triple bonds; or
b) a natural isoprene chain;
n is integer from 1 to 40, or from 2 to 15, or from 5 to 11;
B is a targeting group comprising Sk+Z−, wherein:
Sk is a lipophilic cation; and
Z is a pharmacologically-acceptable anion;
and solvates, salts, and stereoisomers thereof.

### Claim 2 (depends on 1)

The method of claim 1, wherein the antioxidant is one or more of SkQ1:
and its reduced (quinole) form SkQ1H2.

### Claim 3 (depends on 1)

The method of claim 1, wherein the antioxidant is one or more of SkQR1:
and its reduced (quinole) form SkQR1H2.

### Claim 4 (depends on 1)

The method of claim 1, wherein the antioxidant is one or more of SkQ3:
and its reduced (quinole) form SkQ3H2.

### Claim 5 (depends on 1)

The method of claim 1, wherein the antioxidant is one or more of SkQRB:
and its reduced (quinole) form SkQRBH2.

### Claim 6 (depends on 1)

The method of claim 1, wherein the antioxidant is one or more of SkQB1:
and its reduced (quinole) form, SkQB1H2.

### Claim 7 (depends on 1)

The method of claim 1, wherein the antioxidant is one or more of SkQBP1:
and its reduced (quinole) form SkQBP1H2.

### Claim 8 (depends on 1)

The method of claim 1, wherein the antioxidant is one or more of SkQ1, SkQ1H2, SkQR1, SkQR1H2, SkQ3, SkQ3H2, SkQRB, SkQRBH2, SkQB1, SkQBH2, SkQBP1, and SkQBP1H2.