Pyridinyl cyclohexanecarboxamide cooling compounds

Patent metadata

Field	Value
Publication number	US-11059783-B2
Application number	US-201916290300-A
Country	US
Kind code	B2
Filing date	Mar 1, 2019
Priority date	Aug 15, 2005
Publication date	Jul 13, 2021
Grant date	Jul 13, 2021

Abstract

A method of providing a cooling effect to a product includes the incorporation into the product of at least one compound of the formula I

in which m is a number between 0 and 2, X, Y and Z are selected independently from the group consisting of H, halogen, OH, Me, Et, MeO and EtO, and R 1 , R 2 and R 3 together comprise at least 6 carbons, selected such that
(a) (i) R 1 is selected from the group consisting of H, Me, Et, isopropyl and C 4 -C 5 branched alkyl; and
(ii) R 2 and R 3 are independently selected from the group consisting of Me, Et, isopropyl and C 4 -branched alkyl; or
(b) any two or all of R 1 , R 2 and R 3 together form a monocyclic, bicyclic or tricyclic radical having up to 10 carbons.

The compounds confer substantial cooling effects on compositions applied to the skin or taken orally, such as toothpastes, mouthwashes, foodstuffs, beverages, confectionery, tobacco products, skin creams and ointments.

First claim

The invention claimed is:

1. A method of providing a cooling effect to a product, comprising the incorporation into the product of a resolved stereoisomer compound (1R,2S,5R)-2-isopropyl-5-methyl-N-(2-(pyridin-2-yl)ethyl) cyclohexane carboxamide.

2. The method according to claim 1 wherein the resolved stereoisomer compound is used in combination with at least one other cooling compound comprising menthol, menthone, isopulegol, N-ethyl p-menthanecarboxamide, N,2,3-trimethyl-2-isopropylbutanamide, menthyl lactate, menthone glycerine acetal, mono-menthyl succinate, mono-menthyl glutarate, o-menthyl glycerine, menthyl-N,N-dimethylsuccinamate, or 2-sec-butyl cyclohexanone.

3. A product adapted to be applied to the skin or taken orally to give a cooling sensation, comprising a resolved stereoisomer compound (1R,2S,5R)-2-isopropyl-5-methyl-N-(2-(pyridin-2-yl)ethyl) cyclohexane carboxamide.

4. The product according to claim 3 , wherein the product is used in combination with at least one other cooling compound comprising menthol, menthone, isopulegol, N-ethyl p-menthanecarboxamide, N,2,3-trimethyl-2-isopropylbutanamide, menthyl lactate, menthone glycerine acetal, mono-menthyl succinate, mono-menthyl glutarate, o-menthyl glycerine, menthyl-N,N-dimethylsuccinamate, or 2-sec-butyl cyclohexanone.

Assignees

• Givaudan Sa

Inventors

• Bell Karen Ann
• Galopin Christophe C
• Slack Jay Patrick
• Tigani Lori W

Classifications

• A61K2800/244

  Endothermic; Cooling; Cooling sensation · CPC title

• C07D213/40 Primary

  Acylated substituent nitrogen atom · CPC title

• A61K8/4926

  having six membered rings · CPC title

• A23L2/56

  Flavouring or bittering agents (sweeteners A23L2/60) · CPC title

• A61Q11/00

  Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses · CPC title