# US 9,518,004 B2 · Reduced coenzyme Q10 derivative and method for production thereof

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- Number: US 9,518,004 B2
- Document ID: US9518004B2
- Status: Granted
- Kind: B2
- Application number: 14/649,369
- Filed: 2013-12-02
- Published: 2015-10-29
- Granted: 2016-12-13
- Earliest claimed: 2012-12-03
- Assignees: Kaneka Corporation
- Applicants: Kaneka Corporation
- Inventors: Teruyoshi Koga; Yoshihisa Okamoto; Takao Yamaguchi
- Web page: https://patentgrep.com/patent/US9518004B2

## CPC

- C07C 69/96: Esters of carbonic or haloformic acids
- C07C 68/00: Preparation of esters of carbonic or haloformic acids
- C07C 68/08: Purification; Separation; Stabilisation
- C07C 2601/08: the ring being saturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A reduced coenzyme Q10 derivative represented by formula (1), wherein R1 and R2 are each independently H or an alkoxycarbonyl group represented by formula (2), and at least one of them is an alkoxycarbonyl group represented by the formula (2); in the formula (2), R3 is an optionally substituted linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, an optionally substituted aryl group having 6 to 20 carbon atoms, or an optionally substituted heteroaryl group having 4 to 20 carbon atoms, and when R3 is a group substituted with polyethylene glycol, the molecular weight of the polyethylene glycol is not more than 300.

## Claims

### Claim 1

A reduced coenzyme Q10 derivative represented by formula (1),
wherein R1 and R2 are each independently H or an alkoxycarbonyl group represented by formula (2),
and at least one of R1 and R2 is an alkoxycarhonyl group represented by formula (2), and
R3 is a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

### Claim 2 (depends on 1)

The reduced coenzyme Q10 derivative according to claim 1, wherein R1 and R2 are the same.

### Claim 3

A crystal of a reduced coenzyme Q10 derivative represented by formula (1),
wherein R1 and R2 are each independently H or an alkoxycarbonyl group represented by formula (2),
and at least one of R1 and R2 is an alkoxycarbonyl group represented by formula (2), and
R3 is a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

### Claim 4 (depends on 3)

The crystal of the reduced coenzyme Q10 derivative according to claim 3, wherein R3 is an ethyl group, an isopropyl group, an isobutyl group, a cyclopentyl group, or a phenyl group.

### Claim 5 (depends on 3)

The crystal of the reduced coenzyme Q10 derivative according to claim 3, wherein R1 and R2 are the same.

### Claim 6 (depends on 1)

A method for producing the reduced coenzyme Q10 derivative according to claim 1, comprising:
reacting reduced coenzyme Q10 represented by formula (3):
with an alkoxycarbonylation agent in the presence of a base.

### Claim 7 (depends on 6)

The method according to claim 6, further comprising:
forming crystals in an organic solvent.

### Claim 8 (depends on 7)

The method according to claim 7, wherein the organic solvent comprises one or more organic solvents selected from the group consisting of a nitrile, an alcohol, an aliphatic hydrocarbon, an aromatic hydrocarbon, a halogenated hydrocarbon, an ether, and an ester.

### Claim 9 (depends on 7)

The method according to claim 7, wherein the organic solvent is at least one of a nitrile and an alcohol.

### Claim 10 (depends on 8)

The method according to claim 8, wherein the organic solvent is a nitrile.

### Claim 11 (depends on 10)

The method according to claim 10, wherein the nitrile is acetonitrile.

### Claim 12 (depends on 8)

The method according to claim 8, wherein the organic solvent is an alcohol.

### Claim 13 (depends on 12)

The method according to claim 12, wherein the alcohol is ethanol.

### Claim 14 (depends on 1)

The reduced coenzyme Q10 derivative according to claim 1, wherein R1 and R2 are each represented by the formula (2).

### Claim 15 (depends on 3)

The crystal of the reduced coenzyme Q10 derivative according to claim 3, wherein R1 and R2 are each represented by the formula (2).

### Claim 16 (depends on 4)

The crystal of the reduced coenzyme Q10 derivative according to claim 4, wherein R1 and R2 are the same.

### Claim 17 (depends on 1)

The reduced coenzyme Q10 derivative according to claim 1, wherein R3 is an ethyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, or a phenyl group.

### Claim 18 (depends on 1)

The reduced coenzyme Q10 derivative according to claim 1, wherein R3 is an isopropyl group, a cyclopentyl group, or a phenyl group.

### Claim 19 (depends on 18)

The reduced coenzyme Q10 derivative according to claim 18, wherein R1 and R2 are the same.

### Claim 20 (depends on 3)

The crystal of the reduced coenzyme Q10 derivative according to claim 3, wherein R3 is a linear, branched, or cyclic alkyl group having 2 to 6 carbon atoms.