WO2008141469A3 - Butone derivatives useful as cooling agents - Google Patents

Butone derivatives useful as cooling agents Download PDF

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Publication number
WO2008141469A3
WO2008141469A3 PCT/CH2008/000219 CH2008000219W WO2008141469A3 WO 2008141469 A3 WO2008141469 A3 WO 2008141469A3 CH 2008000219 W CH2008000219 W CH 2008000219W WO 2008141469 A3 WO2008141469 A3 WO 2008141469A3
Authority
WO
WIPO (PCT)
Prior art keywords
butone
group
cooling agents
derivatives useful
methyl
Prior art date
Application number
PCT/CH2008/000219
Other languages
French (fr)
Other versions
WO2008141469A2 (en
Inventor
Stefan Michael Furrer
David Max Dastrup
Thomas Scott Mccluskey
Original Assignee
Givaudan Sa
Stefan Michael Furrer
David Max Dastrup
Thomas Scott Mccluskey
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Givaudan Sa, Stefan Michael Furrer, David Max Dastrup, Thomas Scott Mccluskey filed Critical Givaudan Sa
Priority to JP2010508684A priority Critical patent/JP2010527943A/en
Priority to CN200880016988A priority patent/CN101677930A/en
Priority to EP08733840.6A priority patent/EP2155151B1/en
Priority to US12/599,122 priority patent/US7935848B2/en
Priority to BRPI0811924-4A2A priority patent/BRPI0811924A2/en
Publication of WO2008141469A2 publication Critical patent/WO2008141469A2/en
Publication of WO2008141469A3 publication Critical patent/WO2008141469A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/303—Saturated compounds containing keto groups bound to rings to a six-membered ring
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/225—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/35—Saturated compounds containing keto groups bound to rings containing ether groups, groups, groups, or groups
    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • 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

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Confectionery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cooling compounds of formula (I) wherein R1 is selected from the group consisting of hydrogen, methyl, C1-C3 alkoxy, phenyl, C1-C3 alkylphenyl, C1- C3 alkoxyphenyl, thienyl, pyridyl, furyl, and indoyl; R2 is selected from the group consisting of hydrogen and hydroxyl, or R2 forms together with the carbon atom to which it is attached a carbonyl group; and R3 is selected from the group consisting of 2,4-dimethylpent-3-yl, 2,3,4-trimethylpent-3-yl, adamantly and 2-isopropyl-5-methyl-cycloheϰyl-1-yI; and, product compositions comprising them.
PCT/CH2008/000219 2007-05-23 2008-05-14 Butone derivatives useful as cooling agents WO2008141469A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2010508684A JP2010527943A (en) 2007-05-23 2008-05-14 Buton derivatives useful as coolants
CN200880016988A CN101677930A (en) 2007-05-23 2008-05-14 Organic compounds
EP08733840.6A EP2155151B1 (en) 2007-05-23 2008-05-14 Butanone derivatives and use thereof as cooling agents
US12/599,122 US7935848B2 (en) 2007-05-23 2008-05-14 Butone derivatives useful as cooling agents
BRPI0811924-4A2A BRPI0811924A2 (en) 2007-05-23 2008-05-14 BUTONE DERIVATIVES USEFUL AS COOLING AGENTS

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US93133807P 2007-05-23 2007-05-23
US60/931,338 2007-05-23

Publications (2)

Publication Number Publication Date
WO2008141469A2 WO2008141469A2 (en) 2008-11-27
WO2008141469A3 true WO2008141469A3 (en) 2009-05-07

Family

ID=39823539

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CH2008/000219 WO2008141469A2 (en) 2007-05-23 2008-05-14 Butone derivatives useful as cooling agents

Country Status (6)

Country Link
US (1) US7935848B2 (en)
EP (1) EP2155151B1 (en)
JP (1) JP2010527943A (en)
CN (1) CN101677930A (en)
BR (1) BRPI0811924A2 (en)
WO (1) WO2008141469A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2250154A1 (en) * 2008-01-17 2010-11-17 Givaudan SA Benzimidazole derivatives and their use as cooling agents
US10173966B2 (en) * 2015-06-04 2019-01-08 Symrise, Inc. Physiological cooling compounds
BR112018006471B1 (en) 2015-10-01 2024-02-27 Senomyx, Inc COMPOUND, COMPOSITION, METHOD OF MODULATING THE MELASTIN MEMBER OF TRANSIENT RECEPTOR POTENTIAL CHANNEL 8 (TRPM8), METHOD OF MODULATING THE FEELING OF REFRESHMENT OF A COMPOSITION, AND METHOD OF INDUCING A FEELING OF REFRESHMENT IN A HUMAN OR ANIMAL
JP7222921B2 (en) 2017-05-15 2023-02-15 フイルメニツヒ ソシエテ アノニム Compositions containing essential oils
EP3699250A4 (en) 2017-10-16 2021-08-25 Takasago International Corporation Cool-sensation imparter composition containing 2,2,6-trimethylcyclohexanecarboxylic acid derivative
US11389383B2 (en) 2017-12-20 2022-07-19 Firmenich Sa Oral care compositions
CN113194742A (en) 2018-08-10 2021-07-30 弗门尼舍公司 Antagonists of T2R54 and their compositions and uses

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3870759A (en) * 1969-07-19 1975-03-11 Yoshiaki Inamoto 1-Adamantyl alkyl ketones and their preparation
GB1457671A (en) * 1974-01-31 1976-12-08 Wilkinson Sword Ltd Flavour
EP0885869A1 (en) * 1996-02-19 1998-12-23 Japan Tobacco Inc. Therapeutic agent for diabetes
WO2007019719A1 (en) * 2005-08-15 2007-02-22 Givaudan Sa Cooling compounds

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4136163A (en) * 1971-02-04 1979-01-23 Wilkinson Sword Limited P-menthane carboxamides having a physiological cooling effect
US4150052A (en) * 1971-02-04 1979-04-17 Wilkinson Sword Limited N-substituted paramenthane carboxamides
GB0313173D0 (en) * 2003-06-07 2003-07-16 Givaudan Sa Improvements in or related to organic compounds
CN100582089C (en) 2003-11-21 2010-01-20 吉万奥丹股份有限公司 N-substituted p-menthane carbosamided
KR20080020609A (en) 2005-05-27 2008-03-05 지보당 에스아 Cooling compounds
EP2167024B1 (en) * 2007-06-13 2012-01-11 Givaudan SA Cooling compounds

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3870759A (en) * 1969-07-19 1975-03-11 Yoshiaki Inamoto 1-Adamantyl alkyl ketones and their preparation
GB1457671A (en) * 1974-01-31 1976-12-08 Wilkinson Sword Ltd Flavour
EP0885869A1 (en) * 1996-02-19 1998-12-23 Japan Tobacco Inc. Therapeutic agent for diabetes
WO2007019719A1 (en) * 2005-08-15 2007-02-22 Givaudan Sa Cooling compounds

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DUBOIS, BOSSU, TETRAHDERON, vol. 29, 1973, pages 3943 - 3957, XP002500535 *
EIICHI NAKAMURA ET AL, JOURNAL OF ORGANIC CHEMISTRY, vol. 42, no. 25, 1977, pages 4166 - 4167, XP002500534 *
MATSUMOTO, MINATO, TETRAHDRON LETTERS, vol. 17, no. 42, 1976, pages 3827 - 3830, XP002500536 *
WATSON H R ET AL: "NEW COMPOUNDS WITH THE MENTHOL COOLING EFFECT", JOURNAL OF THE SOCIETY COSMETIC CHEMISTS, SOCIETY OF COSMETIC CHEMISTS, US, vol. 29, no. 4, 1 January 1978 (1978-01-01), pages 185 - 200, XP009045124, ISSN: 0037-9832 *
YUDONG CAI ET AL, ORGANIC BIOMOLECULAR CHEMISTRY, vol. 2, 2004, pages 2517 - 2529, XP002500533 *

Also Published As

Publication number Publication date
WO2008141469A2 (en) 2008-11-27
BRPI0811924A2 (en) 2014-11-25
EP2155151B1 (en) 2013-07-31
CN101677930A (en) 2010-03-24
US20100197713A1 (en) 2010-08-05
EP2155151A2 (en) 2010-02-24
US7935848B2 (en) 2011-05-03
JP2010527943A (en) 2010-08-19

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