# US 9,233,903 B2 · Pharmaceutical substances on the basis of mitochondria-addressed antioxidants

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- Number: US 9,233,903 B2
- Document ID: US9233903B2
- Status: Granted
- Kind: B2
- Application number: 13/470,823
- Filed: 2012-05-14
- Published: 2012-10-11
- Granted: 2016-01-12
- Earliest claimed: 2009-11-13
- Assignees: Mitotech SA
- Applicants: Maxim V. Skulachev; Vladimir P. Skulachev; Andrei A. Zamyatin; Evgeny S. Efremov; Vadim N. Tashlitsky; Lev S. Yaguzhinsky; Galina A. Korshunova; Natalya V. Sumbatyan; Yury N. Antonenko; Inna I. Severina; Boris V. Chernyak
- Inventors: Maxim V. Skulachev; Vladimir P. Skulachev; Andrei A. Zamyatin; Evgeny S. Efremov; Vadim N. Tashlitsky; Lev S. Yaguzhinsky; Galina A. Korshunova; Natalya V. Sumbatyan; Yury N. Antonenko; Inna I. Severina; Boris V. Chernyak
- Web page: https://patentgrep.com/patent/US9233903B2

## CPC

- C07C 50/04: Benzoquinones, i.e. C6H4O2
- A61K 47/54: the modifying agent being an organic compound
- A61P 39/06: Free radical scavengers or antioxidants
- C07C 46/06: of at least one hydroxy group on a six-membered aromatic ring
- C07D 487/22: in which the condensed system contains four or more hetero rings
- C09B 47/00: Porphines; Azaporphines {(non-dyeing compounds C07D487/22)}
- 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}
- G01N 33/5079: {Mitochondria}
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- 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)

## Abstract

The present disclosure provides purified pharmaceutical preparations comprising oxidized SkQ1, wherein no individual impurity exceeds 1.5%, the total impurity content of the preparation does not exceed 4.0%, and the content of reduced SkQ1 is not greater than 10%, the structure of oxidized SkQ1 being:

## Claims

### Claim 1

A purified pharmaceutical preparation comprising oxidized SkQ1, said oxidized SkQ1 having the structure:
with the provisos that:
no individual impurity exceeds 1.5% of the preparation;
the total impurity content of the preparation does not exceed 4.0%; and
the content of reduced SkQ1 is not greater than 10%,
said reduced SkQ1 having the structure:

### Claim 2 (depends on 1)

The preparation of claim 1, which is stable at room temperature for at least 1 year.

### Claim 3 (depends on 1)

The preparation of claim 1, which is stable at room temperature for at least 2 years.

### Claim 4 (depends on 1)

The preparation of claim 1, which is stable at 2° C. to 8° C. for at least 2 years.

### Claim 5 (depends on 1)

The preparation of claim 1, which is stable at or below 0° C. for at least 2 years.

### Claim 6

A method of synthesizing a preparation comprising reduced and oxidized SkQ1, reduced SkQ1 being present at not greater than 10%, and oxidized SkQ1 being present at not less than 90%, comprising:
oxidizing 2,3-dimethylphenol to 2,3-dimethyl-1,4-benzoquinone;
linking 11-bromo-undecanoic acid to triphenylphosphine to form 10-carboxy-decyltriphenylphosphine; and
reacting 10-carboxy-decyltriphenylphosphine with 2,3-dimethyl-1,4-benzoquinone in the presence of silver nitrate and ammonium persulfate to form reduced and oxidized SkQ1; and
purifying the oxidized and reduced SkQ1,
the structure of reduced SkQ1 being:
and the oxidized form of SkQ1 being present at not less than 90%, the structure of oxidized SkQ1 being: