Reduced coenzyme Q10 derivative and method for production thereof

Patent metadata

Field	Value
Publication number	US-9518004-B2
Application number	US-201314649369-A
Country	US
Kind code	B2
Filing date	Dec 2, 2013
Priority date	Dec 3, 2012
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

Abstract

A reduced coenzyme Q 10 derivative represented by formula (1),

wherein R 1 and R 2 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), R 3 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 R 3 is a group substituted with polyethylene glycol, the molecular weight of the polyethylene glycol is not more than 300.

First claim

The invention claimed is:

1. A reduced coenzyme Q 10 derivative represented by formula (1),

wherein R 1 and R 2 are each independently H or an alkoxycarbonyl group represented by formula (2),

and at least one of R 1 and R 2 is an alkoxycarhonyl group represented by formula (2), and
R 3 is a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

2. The reduced coenzyme Q 10 derivative according to claim 1 , wherein R 1 and R 2 are the same.

3. A crystal of a reduced coenzyme Q 10 derivative represented by formula (1),

wherein R 1 and R 2 are each independently H or an alkoxycarbonyl group represented by formula (2),

and at least one of R 1 and R 2 is an alkoxycarbonyl group represented by formula (2), and
R 3 is a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

4. The crystal of the reduced coenzyme Q 10 derivative according to claim 3 , wherein R 3 is an ethyl group, an isopropyl group, an isobutyl group, a cyclopentyl group, or a phenyl group.

5. The crystal of the reduced coenzyme Q 10 derivative according to claim 3 , wherein R 1 and R 2 are the same.

6. A method for producing the reduced coenzyme Q 10 derivative according to claim 1 , comprising:
reacting reduced coenzyme Q 10 represented by formula (3):

with an alkoxycarbonylation agent in the presence of a base.

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

8. 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.

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

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

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

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

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

14. The reduced coenzyme Q 10 derivative according to claim 1 , wherein R 1 and R 2 are each represented by the formula (2).

15. The crystal of the reduced coenzyme Q 10 derivative according to claim 3 , wherein R 1 and R 2 are each represented by the formula (2).

16. The crystal of the reduced coenzyme Q 10 derivative according to claim 4 , wherein R 1 and R 2 are the same.

17. The reduced coenzyme Q 10 derivative according to claim 1 , wherein R 3 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.

18. The reduced coenzyme Q 10 derivative according to claim 1 , wherein R 3 is an isopropyl group, a cyclopentyl group, or a phenyl group.

19. The reduced coenzyme Q 10 derivative according to claim 18 , wherein R 1 and R 2 are the same.

20. The crystal of the reduced coenzyme Q 10 derivative according to claim 3 , wherein R 3 is a linear, branched, or cyclic alkyl group having 2 to 6 carbon atoms.

Assignees

• Kaneka Corp

Inventors

• Koga Teruyoshi
• Okamoto Yoshihisa
• Yamaguchi Takao

Classifications

• C07C68/00

  Preparation of esters of carbonic or haloformic acids · CPC title

• C07C69/96 Primary

  Esters of carbonic or haloformic acids · CPC title

• C07C2601/08

  the ring being saturated · CPC title

• C07C68/08

  Purification; Separation; Stabilisation · CPC title

• C07C2101/08

  Chemistry & Metallurgy · mapped topic