Use of cyclohexanol derivatives as antimicrobial active compounds

Patent metadata

Field	Value
Publication number	US-10071037-B2
Application number	US-201615215962-A
Country	US
Kind code	B2
Filing date	Jul 21, 2016
Priority date	Dec 21, 2011
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

The present invention relates to the use of at least one cyclohexanol derivative of the formula (I) and/or (II) as antimicrobial active compound or as anti-acne, antidandruff, antiperspirant or deodorant active compound, to preparations comprising these compounds, and to specific cyclohexanol derivatives and to a process for the preparation thereof.

First claim

The invention claimed is:

1. A composition comprising:
one or more compounds of formulae Ia, Ib, IIa or IIb

in which R6 and R7 stand, independently of one another, for a radical selected from
H
(CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20,
straight-chain or branched alkyl group having 1 to 20 C atoms, and
straight-chain or branched alkenyl or alkynyl group having 2 to 20 C atoms and one or more double or triple bonds,

where the alkyl, alkenyl or alkynyl group may also contain one or more saturated or unsaturated C 3 - to C 12 -cycloalkyl groups,
where compounds of formula Ia in which R6 stands for H (compound I-11), methyl (compound I-1), ethyl (compound I-2), isopropyl (compound I-4), tert-butyl (compound I-5), n-hexyl (compound I-8), CH 2 CH(CH 2 CH 3 ) 2 , CH 2 CH 2 CH(CH 3 ) 2 , C(═CH 2 )CH 3 or cyclopentyl are excluded,
where compounds of formula Ib in which R6 stands for H (compound I-25), methyl (compound I-15), ethyl (compound I-16), propyl (compound I-17), isopropyl (compound I-18) or tert-butyl (compound I-19) are excluded,
where compounds of formula IIa in which R6 stands for H and R7 stands for H, methyl, phenyl, p-tolyl, phenylmethyl or 2-phenylethyl or in which R6 and R7 simultaneously stand for ethyl are excluded, and
where compounds of formula IIb in which R6 and R7 simultaneously stand for H are excluded; and

in addition to said one or more compounds of formulae Ia, Ib, IIa or IIb, said composition contains at least one compound selected from preservatives, antimicrobial active compounds, antibiotics, humectants, surface-active agents, structure formers, gel formers, abrasives, fluoride sources, desensitizers, flavors, dyes, sweeteners, antiplaque agents, anti-tartar agents, UV filters, colored pigments, antioxidants, anti-ageing agents, anti-wrinkle agents, antidandruff agents, anti-acne agents, anti-cellulite active compounds, deodorants, skin-lightening active compounds, self-tanning substances, and vitamins; and
said composition further contains at least one suitable vehicle.

2. The composition according to claim 1 , wherein said at least one compound of formulae Ia, Ib, IIa or IIb is present in an amount of 0.01 to 20% by weight, based on the total amount of the composition.

3. The composition according to claim 1 , wherein said composition contains, in addition to said one or more compounds of formulae Ia, Ib, IIa or IIb, a deodorant, antiperspirant, antidandruff, anti-acne or antibacterial compound.

4. The composition according to claim 1 , wherein the radicals R6 and R7 each stand for a radical selected from
H,
CH 2 —CH 2 —OH, and
straight-chain or branched alkyl group having 1 to 10 C atoms, which may also contain a saturated or unsaturated C 6 -cycloalkyl group.

5. The composition according to claim 1 , wherein said at least one compound is selected from the following compounds:

6. The composition according to claim 5 , wherein said at least one compound is selected from the compounds of formulae I-20 to I-24 and I-26 to I-28:

7. The composition according to claim 6 , wherein said at least one compound is a compound of formula I-20.

8. The composition according to claim 1 , wherein said at least one compound is selected from the following compounds:

9. The composition according to claim 1 , wherein in which R6 and R7 stand, independently of one another, for a radical selected from
H,
(CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20,
methyl, ethyl, isopropyl, propyl, butyl, sec-butyl or tert-butyl, pentyl, isopentyl, 1-, 2- or 3-methylbutyl, 1,1-, 1,2- or 2,2-dimethylpropyl, 1-ethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1,1,2- or 1,2,2-trimethylpropyl, 1,1-, 1,2-, 1,3-, 2,2-, 2,3- or 3,3-dimethylbutyl, 1- or 2-ethylbutyl, 1-, 2-, 3- or 4-methylpentyl, hexyl, heptyl, 1-ethylpentyl, octyl, 1-ethylhexyl, nonyl or decyl,
allyl, vinyl, propenyl, 2- or 3-butenyl, isobutenyl, sec-butenyl, 2-methyl-1- or 2-butenyl, 3-methyl-1-butenyl, 1,3-butadienyl, 2-methyl-1,3-butadienyl, 2,3-dimethyl-1,3-butadienyl, 1-, 2-, 3- or 4-pentenyl, iso-pentenyl, hexenyl, heptenyl or octenyl, and
ethynyl, 1- or 2-propynyl, 2- or 3-butynyl, furthermore 4-pentynyl, 3-pentynyl, hexynyl, heptynyl, octynyl.

10. The composition according to claim 1 , wherein said vehicle is glyceryl stearate, aluminum chlorohydrate, propylene glycol, carbomer, glycerol, dicapryl ether, ethanol, glyceryl cocoate, cylomethicone, dimethicone, dipropylene glycol, stearyl alcohol, mineral oil, phenyltrimethicone or sodium stearate.

11. The composition according to claim 1 , wherein said at least one compound of formulae Ia, Ib, IIa or IIb is present in an amount of 0.05 to 10% by weight, based on the total amount of the composition.

12. The composition according to claim 1 , wherein said at least one compound of formulae Ia, Ib, IIa or IIb is present in an amount of 0.1 to 5% by weight, based on the total amount of the composition.

13. The composition according to claim 1 , wherein said at least one compound of formula I is a compound of formula Ia or Ib.

14. The composition according to claim 1 , wherein said composition contains at least one compound selected from preservatives and antimicrobial active compounds.

15. The composition according to claim 1 , wherein said composition contains at least one compound selected from antibiotics.

16. The composition according to claim 1 , wherein said composition contains at least one compound selected from humectants, surface-active agents, structure formers, gel formers, abrasives, fluoride sources, desensitizers, flavors, dyes, sweeteners, antiplaque agents, and anti-tartar agents.

17. The composition according to claim 1 , wherein said composition contains at least one compound selected from UV filters.

18. The composition according to claim 1 , wherein said composition contains at least one compound selected from colored pigments.

19. The composition according to claim 1 , wherein said composition contains at least one compound selected from antioxidants, anti-ageing agents, anti-wrinkle agents, antidandruff agents, anti-acne agents, anti-cellulite active compounds, deodorants, skin-lightening active compounds, self-tanning substances, and vitamins.

20. The composition according to claim 1 , wherein said composition contains at least one antimicrobial active compound that is an antibacterial compound.

21. A process for the preparation of a composition according to claim 1 , wherein said at least one compound of formulae Ia, Ib,IIa or IIb is mixed with said at least one suitable vehicle and said at least one compound selected from preservatives, antimicrobial active compounds, antibiotics, humectants, surface-active agents, structure formers, gel formers, abrasives, fluoride sources, desensitizers, flavors, dyes, sweeten

Assignees

• Merck Patent Gmbh

Inventors

• Rudolph Thomas
• Mueller Tatjana

Classifications

• A61P31/00

  Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics · CPC title

• A61P31/04

  Antibacterial agents · CPC title

• A61P1/02

  Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis · CPC title

• A61K31/215

  of carboxylic acids · CPC title

• A61Q19/10

  Washing or bathing preparations · CPC title