Use of cyclohexanol derivatives as antimicrobial active compounds

Patent metadata

Field	Value
Publication number	US-RE46698-E
Application number	US-201215449149-A
Country	US
Kind code	E1
Filing date	Dec 3, 2012
Priority date	Dec 21, 2011
Publication date	Feb 6, 2018
Grant date	Feb 6, 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 method for achieving an antimicrobial effect in a host in need thereof, comprising administering to a host in need thereof an effective amount of at least one compound of the formula I and/or II

in which R1, R2, R3, R4 and R5 stand, independently of one another, for a radical selected from
H, OH, OCOCH 3 , O—(CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20,
straight-chain or branched alkyl or alkoxy group having 1 to 20 C atoms, where at least one of the radicals R1, R2, R3, R4 and R5 stands for OH, OCOCH 3 or O—(CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20,

and 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,
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,

with the proviso the following compound is excluded:

2. The method according to claim 1 comprising administering in the form of cosmetic or pharmaceutical formulations, medicinal products or foods.

3. The method according to claim 2 comprising administering in the form of a dental or oral care product.

4. The method according to claim 1 , wherein the radicals R1, R2, R3, R4 and R5 stand, independently of one another, for H or OH, where 1, 2 or 3 of the radicals R1, R2, R3, R4 and R5 stand for OH.

5. The method according to claim 4 , wherein the compound of the formula I and II is a compound of formula Ia, Ib, IIa and IIb

in which R6 and R7 stand, independently of one another, for
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,
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.

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

7. The method according to claim 6 , wherein the compound of the formula I is a compound selected from formulae I-1 to I-10 and I-12 to I-28

8. A method for achieving an antimicrobial effect in a subject, comprising administering to a subject in need thereof an anti-acne, antidandruff, antiperspirant or deodorant formulation containing an effective amount of at least one compound of the formula I and/or II

in which R1, R2, R3, R4 and R5 stand, independently of one another, for a radical selected from
H, OH, OCOCH 3 , O—(CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20,
straight-chain or branched alkyl or alkoxy group having 1 to 20 C atoms, where at least one of the radicals R1, R2, R3, R4 and R5 stands for OH, OCOCH 3 or O—(CH 2 —CH 2 —O) n —CH 2 —CH 2 —OH, where n=0 to 20,

and 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,
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.

9. The method according to claim 1, wherein an effective amount of at least one compound of the formula I is administered to said host.

10. The method according to claim 9, wherein the radicals R1, R2, R3, R4 and R5 stand, independently of one another, for H or OH, where 1, 2 or 3 of the radicals R1, R2, R3, R4 and R5 stand for OH.

11. The method according to claim 10, wherein said compound of formula I is a compound of formula Ia or Ib:

in which R6 stands for
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,
straight-chain or branched alkenyl or alkynyl group having 2 to 20 C atoms and one or more double or triple bonds,
wherein the alkyl, alkenyl and alkynyl groups each optionally contain one or more saturated or unsaturated C 3 - to C 12 -cycloalkyl groups.

12. The method according to claim 11, wherein the R6 stands for
H, CH 2 —CH 2 —OH, straight-chain or branched alkyl group having 1 to 10 C atoms, which optionally contains a saturated or unsaturated C 6 -cycloalkyl group.

13. The method according to claim 12, wherein the compound of the formula I is a compound selected from formulae I-15 to I-28

14. The method according to claim 13, wherein said compound of formula I is a compound of formula I-20.

15. The method according to claim 8, wherein an effective amount of at least one compound of the formula I is administered to said subject.

16. The method according to claim 15, wherein the radicals R1, R2, R3, R4 and R5 stand, independently of one another, for H or OH, where 1, 2 or 3 of the radicals R1, R2, R3, R4 and R5 stand for OH.

17. The method according to claim 16, wherein said compound of formula I is a compound of formula Ia or Ib:

in which R6 stands for
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,
straight-chain or branched alkenyl or alkynyl group having 2 to 20 C atoms and one or more double or triple bonds,
wherein the alkyl, alkenyl and alkynyl groups each optionally contain one or more saturated or unsaturated C 3 - to C 12 -cycloalkyl groups.

18. The method according to claim 17, wherein the R6 stands for
H, CH 2 —CH 2 —OH, straight-chain or branched alkyl group having 1 to 10 C atoms, which optionally contains a saturated or unsaturated C 6 -cycloalkyl group.

19. The method according to claim 18, wherein the compound of the formula I is a compound selected from formulae I-15 to I-28

Assignees

• Merck Patent Gmbh

Inventors

• Rudolph Thomas
• Best Tatjana

Classifications

• A61P31/04

  Antibacterial agents · CPC title

• A61P31/00

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

• A61P1/02

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

• A61Q11/02

  Preparations for deodorising, bleaching or disinfecting dentures · CPC title

• A01N37/36 Primary

  containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids · CPC title