WO2007019719A1 - Cooling compounds - Google Patents
Cooling compounds Download PDFInfo
- Publication number
- WO2007019719A1 WO2007019719A1 PCT/CH2006/000427 CH2006000427W WO2007019719A1 WO 2007019719 A1 WO2007019719 A1 WO 2007019719A1 CH 2006000427 W CH2006000427 W CH 2006000427W WO 2007019719 A1 WO2007019719 A1 WO 2007019719A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- isopropyl
- compounds
- carbons
- branched alkyl
- Prior art date
Links
- 0 C*(C)CNC(C(*)(*)*)=O Chemical compound C*(C)CNC(C(*)(*)*)=O 0.000 description 1
- RDOAUPPSCNSYPM-UHFFFAOYSA-N C1C=CN=CC1 Chemical compound C1C=CN=CC1 RDOAUPPSCNSYPM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/24—Thermal properties
- A61K2800/244—Endothermic; Cooling; Cooling sensation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/92—Oral administration
Definitions
- This invention relates to cooling compounds.
- Cooling compounds that is, chemical compounds that impart a cooling sensation to the skin or the mucous membranes of the body, are well known to the art and are widely used in a variety of products such as foodstuffs, tobacco products, beverages, dentifrices, mouthwashes and toiletries.
- 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
- R 1 is selected from the group consisting of H, Me, Et, isopropyl and
- R and R are independently selected from the group consisting of Me. Et, isopropyl and C 4 -branched alkyl; or
- BESTATIGUNGSKOPIE 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.
- Me is defined as methyl
- Et is defined as ethyl
- Examples of cyclic radicals as described under (b) above include 3-para-menthyl, bornyl and adamantyl.
- the compounds of formula (I) may comprise one or more chiral centres and as such may exist as a mixture of stereoisomers, or they may be resolved as isomerically pure forms. Resolving stereoisomers adds to the complexity of manufacture and purification of these compounds and so it is preferred to use the compounds as mixtures of their stereoisomers simply for economic reasons. However, if it is desired to prepare individual stereoisomers, this may be achieved according to methods known in the art, e.g. preparative HPLC and GC or by stereoselective syntheses.
- the compounds are those in which X, Y, Z are H, OH, Me or OMe. In certain embodiments, the compounds are those in which m is 2; X, Y and Z are H or Me and R 1 , R 2 and R 3 are taken from Table 1.
- Table 1 Exemplary R , R and R groups.
- a particularly effective compound is that in which R 1 is H and R 2 and R 3 together form a 3-p-menthyl ring.
- Examples of effective compounds are (lR,2S,5R)-2-isopropyl-5-methyl-N- (pyridinalkyl)cyclohexanecarboxamide and (2S,5R)-2-isopropyl-5-methyl-N- (pyridinalkyl)cyclohexanecarboxamide.
- a compound is also provided according to formula I as hereinabove described, in which X, Y, Z, R 1 are H and R 2 , R 3 have the meanings given hereinabove.
- R 1 is hydrogen and R 2 and R 3 are independently selected from the group consisting of Me, Et and C 3 -C 4 branched alkyl; or R 1 , R 2 and R 3 together form a monocyclic, bicyclic or tricyclic radical having up to 10 carbons.
- the compounds may be easily prepared and isolated by art-recognized methods
- the compounds may be used in products that are applied to the mouth or the skin to give a cooling sensation.
- applying is meant any form of bringing into contact, for example, oral ingestion or, in the case of tobacco products, inhalation, hi the case of application to the skin, it may be, for example, by including the compound in a cream or salve, or in a sprayable composition.
- the range of products in which the compounds may be used is very wide, and it includes by way of example only, dentifrices such as toothpaste and toothgel, mouthwashes, foodstuffs, beverages, confectionery, tobacco products, skin creams and ointments, both cosmetic and medicinal.
- the compounds may be used alone or in combination with other cooling compounds known in the art, e.g., menthol, menthone, isopulegol, N-ethyl p- menthanecarboxamide (WS-3), N,2,3-trimethyl-2-isopropylbutanamide (WS-23), menthyl lactate (FrescolatTM ML), menthone glycerine acetal (FrescolatTM MGA), mono-menthyl succinate (PhyscoolTM), mono-menthyl glutarate, O-menthyl glycerine (Cool ActTM 10), menthyl-N,N-dimethylsuccinamate and 2-sec-butylcyclohexanone (FreskomentheTM).
- other cooling compounds known in the art, e.g., menthol, menthone, isopulegol, N-ethyl p- menthanecarboxamide (WS-3), N,2,3-tri
- Peppermint oil Terpeneless 0.300 g
- PluronicTM F127 nonionic surfactant 5.000 g Sodium Saccharin 0.600 g
- the chemicals are mixed in the toothgel, a piece of toothgel is put on a toothbrush and a panelist's teeth are brushed.
- the mouth is rinsed with water and the water is spit out. An intense cooling sensation is felt by the panelist in all areas of the mouth.
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200680029790XA CN101257949B (en) | 2005-08-15 | 2006-08-14 | Cooling compounds |
EP06761278.8A EP1917074B1 (en) | 2005-08-15 | 2006-08-14 | Cooling compounds |
BRPI0616821-3A BRPI0616821B1 (en) | 2005-08-15 | 2006-08-14 | Method for providing a cooling effect in a product and product having a cooling effect |
US11/990,103 US9452982B2 (en) | 2005-08-15 | 2006-08-14 | Pyridinyl cyclohexanecarboxamide cooling compounds |
ES06761278.8T ES2668361T3 (en) | 2005-08-15 | 2006-08-14 | Refrigerant compounds |
JP2008526348A JP5383191B2 (en) | 2005-08-15 | 2006-08-14 | Refreshing compound |
US15/276,248 US10221136B2 (en) | 2005-08-15 | 2016-09-26 | Pyridinyl cyclohexanecarboxamide cooling compounds |
US16/290,300 US11059783B2 (en) | 2005-08-15 | 2019-03-01 | Pyridinyl cyclohexanecarboxamide cooling compounds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US70815305P | 2005-08-15 | 2005-08-15 | |
US60/708,153 | 2005-08-15 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/990,103 A-371-Of-International US9452982B2 (en) | 2005-08-15 | 2006-08-14 | Pyridinyl cyclohexanecarboxamide cooling compounds |
US15/276,248 Continuation US10221136B2 (en) | 2005-08-15 | 2016-09-26 | Pyridinyl cyclohexanecarboxamide cooling compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2007019719A1 true WO2007019719A1 (en) | 2007-02-22 |
Family
ID=37215970
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CH2006/000427 WO2007019719A1 (en) | 2005-08-15 | 2006-08-14 | Cooling compounds |
Country Status (7)
Country | Link |
---|---|
US (3) | US9452982B2 (en) |
EP (1) | EP1917074B1 (en) |
JP (1) | JP5383191B2 (en) |
CN (1) | CN101257949B (en) |
BR (1) | BRPI0616821B1 (en) |
ES (1) | ES2668361T3 (en) |
WO (1) | WO2007019719A1 (en) |
Cited By (30)
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WO2008107137A2 (en) * | 2007-03-02 | 2008-09-12 | Givaudan Nederland Services B.V. | Compositions comprising a physiological coolant |
WO2008141469A2 (en) * | 2007-05-23 | 2008-11-27 | Givaudan Sa | Butone derivatives useful as cooling agents |
WO2008148234A1 (en) | 2007-06-06 | 2008-12-11 | Givaudan Sa | Salt enhancement |
WO2008151460A2 (en) | 2007-06-13 | 2008-12-18 | Givaudan Sa | Cooling compounds |
WO2009012609A1 (en) | 2007-07-23 | 2009-01-29 | Givaudan Sa | Amide addition reaction |
WO2009115165A2 (en) * | 2008-03-20 | 2009-09-24 | Beiersdorf Ag | Cooling preparations for contact with human skin and/or mucous membranes, containing (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridin-2-yl)ethyl-cyclohexane carboxamide and/or (1r,2s,5r)-n-(4-(cyanomethyl)-phenyl)-2-isopropyl-5-methylcyclohexane carboxamide |
WO2009115164A2 (en) * | 2008-03-20 | 2009-09-24 | Beiersdorf Ag | Cooling cosmetic or dermatological preparations having a content of (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridyne-2-yl)ethyl-cyclohexane carboxamide and/or (1r,2s,5r)-n-(4-(cyanomethyl)phenyl)-2-isopropyl-5- methylcyclohexane carboxamide comprising menthoxypropane diol |
WO2009115163A2 (en) * | 2008-03-20 | 2009-09-24 | Beiersdorf Ag | Cooling cosmetic or dermatological preparations having a content of (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridyne-2-yl)ethyl-cyclohexane carboxamide and/or (1r,2s,5r)-n-(4-(cyanomethyl)phenyl)-2-ispropyl-5-methylcyclohexane carboxamide for the reduction of erythema |
WO2009127282A1 (en) * | 2008-03-20 | 2009-10-22 | Beiersdorf Ag | Preparations for reducing itching and other paraesthesias which with (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridin-2yl)ethylcyclohexyl carboxamide and/or (1r,2s,5r)-n84-(cyanomethyl)-phenyl)-2-isopropyl-5-methylcyclohexyl carboxamide |
WO2009140783A1 (en) * | 2008-05-22 | 2009-11-26 | Givaudan Sa | Cooling composition |
WO2010076123A2 (en) | 2008-12-30 | 2010-07-08 | Unilever Nv | A non-freezing dentifrice composition |
WO2010128026A2 (en) * | 2009-05-05 | 2010-11-11 | Givaudan Sa | Organic compounds |
WO2010149798A2 (en) | 2010-06-14 | 2010-12-29 | Symrise Ag | Use of polyols for enhancing the cooling effect of a cooling substance and cooling mixtures having an enhanced cooling effect |
WO2011012671A1 (en) | 2009-07-29 | 2011-02-03 | Givaudan Sa | Improvements in or relating to organic compounds |
WO2011012421A1 (en) | 2009-07-29 | 2011-02-03 | Unilever Nv | A dentifrice composition comprising polyethyleneglycol and a cooling agent |
WO2011061330A2 (en) | 2009-11-20 | 2011-05-26 | Symrise Ag | Use of physiological cooling active ingredients, and agents containing such active ingredients |
WO2012113873A2 (en) | 2011-02-23 | 2012-08-30 | Givaudan Sa | Organic compounds |
US8309598B2 (en) | 2007-12-19 | 2012-11-13 | Givaudan S.A. | Cooling compounds |
US8357318B2 (en) | 2007-05-08 | 2013-01-22 | Givaudan S.A. | Wax encapsulation |
WO2013014235A2 (en) | 2011-07-26 | 2013-01-31 | Givaudan Sa | Rinse-off compositions |
US8377422B2 (en) | 2007-12-07 | 2013-02-19 | Givaudan S.A. | Carboxamide derivatives having cooling properties |
WO2013041621A1 (en) | 2011-09-20 | 2013-03-28 | Basf Se | Low molecular weight modulators of the cold-menthol receptor trpm8 and use thereof |
USRE44339E1 (en) | 2003-11-21 | 2013-07-02 | Givaudan S.A. | N-substituted P-menthane carboxamides |
US8710096B2 (en) | 2008-08-26 | 2014-04-29 | Basf Se | Detection and use of low molecular-weight modulators of the cold-menthol receptor TRPM8 |
US9029415B2 (en) | 2010-06-14 | 2015-05-12 | Symrise Ag | Cooling mixtures with an enhanced cooling effect of 5-methyl-2-(propane-2-yl)cyclohexyl-N-ethyloxamate |
WO2019043164A1 (en) | 2017-08-31 | 2019-03-07 | Basf Se | Use of physiological cooling active ingredients, and compositions comprising such active ingredients |
EP3689324A1 (en) | 2019-02-04 | 2020-08-05 | Symrise AG | New cooling agents and preparations comprising them |
WO2022105986A1 (en) | 2020-11-17 | 2022-05-27 | Symrise Ag | Novel cooling agents and preparations containing same |
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2006
- 2006-08-14 US US11/990,103 patent/US9452982B2/en active Active
- 2006-08-14 BR BRPI0616821-3A patent/BRPI0616821B1/en active IP Right Grant
- 2006-08-14 ES ES06761278.8T patent/ES2668361T3/en active Active
- 2006-08-14 JP JP2008526348A patent/JP5383191B2/en active Active
- 2006-08-14 EP EP06761278.8A patent/EP1917074B1/en active Active
- 2006-08-14 WO PCT/CH2006/000427 patent/WO2007019719A1/en active Application Filing
- 2006-08-14 CN CN200680029790XA patent/CN101257949B/en active Active
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2016
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2019
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CN101257949A (en) | 2008-09-03 |
US20190194134A1 (en) | 2019-06-27 |
CN101257949B (en) | 2011-01-19 |
US9452982B2 (en) | 2016-09-27 |
US20170008845A1 (en) | 2017-01-12 |
EP1917074A1 (en) | 2008-05-07 |
US10221136B2 (en) | 2019-03-05 |
JP2009507778A (en) | 2009-02-26 |
ES2668361T3 (en) | 2018-05-17 |
US20100035938A1 (en) | 2010-02-11 |
JP5383191B2 (en) | 2014-01-08 |
US11059783B2 (en) | 2021-07-13 |
BRPI0616821B1 (en) | 2022-06-07 |
EP1917074B1 (en) | 2018-02-28 |
BRPI0616821A2 (en) | 2012-04-24 |
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