JP4786544B2 - N置換p−メンタンカルボキサミド類 - Google Patents
N置換p−メンタンカルボキサミド類 Download PDFInfo
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- JP4786544B2 JP4786544B2 JP2006540126A JP2006540126A JP4786544B2 JP 4786544 B2 JP4786544 B2 JP 4786544B2 JP 2006540126 A JP2006540126 A JP 2006540126A JP 2006540126 A JP2006540126 A JP 2006540126A JP 4786544 B2 JP4786544 B2 JP 4786544B2
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- cooling
- menthane carboxamide
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- -1 N-substituted p-menthane carboxamides Chemical class 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 238000001816 cooling Methods 0.000 claims abstract description 19
- 230000000694 effects Effects 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 3
- FPJRGEOLQICYQZ-UHFFFAOYSA-N n-[4-(cyanomethyl)phenyl]-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide Chemical compound CC(C)C1CCC(C)CC1C(=O)NC1=CC=C(CC#N)C=C1 FPJRGEOLQICYQZ-UHFFFAOYSA-N 0.000 claims description 3
- LXPSLQYJADBSNA-UHFFFAOYSA-N 5-methyl-2-propan-2-yl-n-(4-sulfamoylphenyl)cyclohexane-1-carboxamide Chemical compound CC(C)C1CCC(C)CC1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1 LXPSLQYJADBSNA-UHFFFAOYSA-N 0.000 claims description 2
- IPINMMIMRHRFEG-UHFFFAOYSA-N n-(4-acetylphenyl)-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide Chemical compound CC(C)C1CCC(C)CC1C(=O)NC1=CC=C(C(C)=O)C=C1 IPINMMIMRHRFEG-UHFFFAOYSA-N 0.000 claims description 2
- XGIZWERJPUCCKV-UHFFFAOYSA-N n-(4-cyanophenyl)-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide Chemical compound CC(C)C1CCC(C)CC1C(=O)NC1=CC=C(C#N)C=C1 XGIZWERJPUCCKV-UHFFFAOYSA-N 0.000 claims description 2
- FAPXMWNLKPZDBE-UHFFFAOYSA-N n-[4-(hydroxymethyl)phenyl]-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide Chemical compound CC(C)C1CCC(C)CC1C(=O)NC1=CC=C(CO)C=C1 FAPXMWNLKPZDBE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 5
- 230000035597 cooling sensation Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000606 toothpaste Substances 0.000 description 3
- 229940034610 toothpaste Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229940041616 menthol Drugs 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000008447 perception Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000019505 tobacco product Nutrition 0.000 description 2
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical compound NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 description 1
- LEDWHZJKVDKYHH-UHFFFAOYSA-N C(=O)(O)Cl.C1(CCC(CC1)C(C)C)C Chemical compound C(=O)(O)Cl.C1(CCC(CC1)C(C)C)C LEDWHZJKVDKYHH-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000551 dentifrice Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- CFAIGEXTVUJYJT-UHFFFAOYSA-N n-(3-hydroxy-4-methoxyphenyl)-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide Chemical compound C1=C(O)C(OC)=CC=C1NC(=O)C1C(C(C)C)CCC(C)C1 CFAIGEXTVUJYJT-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/60—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/61—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
- C07C255/44—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms at least one of the singly-bound nitrogen atoms being acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/46—Y being a hydrogen or a carbon atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Ceramic Products (AREA)
Description
冷却化合物、即ち、冷却感覚を身体の皮膚または粘膜に付与する化合物は、当該分野において十分知られており、種々の製品、例えば食料品、タバコ製品、飲料、歯磨剤、洗口剤および化粧品において広範囲に用いられている。
顕著な成功を享受している冷却化合物の1つの群は、N置換p−メンタンカルボキサミド類からなる。これらの化合物の例は、例えば、英国特許GB 1,351,761-2および米国特許第4,150,052号中に記載されている。
(b)YまたはZがHである場合、X、YおよびZは、
(i)3および4位における基は、共にOMeではなく、
(ii)4および5位における基は、共にOMeではなく、
(iii)4位における基がOHである場合には、3および5位における基はOMeではなく、
(iv)4位における基がメチルである場合には、3および5位における基はOHではない
ようになっている、
で表される化合物を提供する。
非結合電子を有する好ましい基は、ハロゲン、OH、OMe、NO2、CN、Ac、SO2NH2、CHO、CO2HおよびC1〜C4アルキルカルボキシレート、例えばCO2Etである。
これらは、従来技術の同様の化合物から、これらの驚異的に高い冷却効果(同様の既知の化合物の冷却効果よりも10倍まで高い)により、および冷却効果の寿命により区別され、これは、多様な製品におけるこれらの魅力に付け加えられる。
ここで、本発明を、好ましい態様を記載する以下の限定的でない例により、さらに記載する。
N−(4−シアノメチルフェニル)p−メンタンカルボキサミドの製造
フラスコに、6.6g(50mmol)のシアン化4−アミノベンジル、4.04mLのピリジンおよび100mLのMtBEを加えた。この混合物に、10gの塩化p−メンタンカルボキシルを、5分にわたり滴加した。反応混合物を、24時間攪拌した。反応混合物に、50mLの水を加えた。混合物を分離した。有機層を、50mLの水および50mLのブラインで洗浄した。有機層を、MgSO4上で乾燥した。溶媒を、真空において蒸発させて、粗製の生成物を得、これを、ヘキサンから再結晶して、以下の分光学的特性を有する10.1gの所望の生成物が、得られた:
Claims (3)
- N−(4−シアノメチルフェニル)p−メンタンカルボキサミド。
- N−(4−シアノメチルフェニル)p−メンタンカルボキサミド、N−(4−シアノフェニル)p−メンタンカルボキサミド、N−(4−スルファモイルフェニル)p−メンタンカルボキサミド、N−(4−アセチルフェニル)p−メンタンカルボキサミド、N−(4−ヒドロキシルメチルフェニル)p−メンタンカルボキサミドおよびN−(3−ヒドロキシル−4−メトキシフェニル)p−メンタンカルボキサミドからなる群から選択される1種または2種以上の冷却化合物を含む、組成物。
- 請求項1に記載の化合物または請求項2に記載の組成物を含む製品を適用することによって、口または皮膚に冷却効果を提供する方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US52397703P | 2003-11-21 | 2003-11-21 | |
US60/523,977 | 2003-11-21 | ||
PCT/CH2004/000646 WO2005049553A1 (en) | 2003-11-21 | 2004-10-28 | N-substituted p-menthane carbosamided |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2007511546A JP2007511546A (ja) | 2007-05-10 |
JP2007511546A5 JP2007511546A5 (ja) | 2007-11-29 |
JP4786544B2 true JP4786544B2 (ja) | 2011-10-05 |
Family
ID=34619622
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006540126A Active JP4786544B2 (ja) | 2003-11-21 | 2004-10-28 | N置換p−メンタンカルボキサミド類 |
Country Status (10)
Country | Link |
---|---|
US (2) | US7414152B2 (ja) |
EP (1) | EP1685093B3 (ja) |
JP (1) | JP4786544B2 (ja) |
CN (1) | CN100582089C (ja) |
AT (1) | ATE464283T1 (ja) |
BR (1) | BRPI0416770B1 (ja) |
DE (1) | DE602004026619D1 (ja) |
ES (1) | ES2342466T7 (ja) |
PL (1) | PL1685093T6 (ja) |
WO (1) | WO2005049553A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20170131432A (ko) * | 2015-03-25 | 2017-11-29 | 다카사고 고료 고교 가부시키가이샤 | 메틸멘톨 유도체 및 그것을 함유하는 냉감제 조성물 |
Families Citing this family (178)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20070107083A (ko) * | 2005-03-01 | 2007-11-06 | 지보당 에스아 | 냉각 특성을 갖는 멘탄 카복스아마이드 유도체 |
GB0504194D0 (en) | 2005-03-02 | 2005-04-06 | Givaudan Sa | Organic compounds |
WO2006125334A1 (en) * | 2005-05-27 | 2006-11-30 | Givaudan Sa | Cooling compounds |
US9452982B2 (en) * | 2005-08-15 | 2016-09-27 | Givaudan, S.A. | Pyridinyl cyclohexanecarboxamide cooling compounds |
EP1940791B1 (en) | 2005-10-25 | 2009-09-16 | Givaudan SA | Organic compounds |
EP1996535A2 (en) * | 2006-03-15 | 2008-12-03 | Givaudan SA | Para-substituted 2-alkoxyphenol compounds |
DE602007004492D1 (de) * | 2006-07-14 | 2010-03-11 | Givaudan Sa | Benzimidazole als kühlende verbindungen |
CN101583287A (zh) * | 2006-12-20 | 2009-11-18 | 奇华顿荷兰服务有限责任公司 | N-取代-对薄荷烷-3-甲酰胺及其用途 |
GB0704163D0 (en) * | 2007-03-02 | 2007-04-11 | Quest Int Serv Bv | Compositions comprising a physiological coolant |
BRPI0811924A2 (pt) | 2007-05-23 | 2014-11-25 | Givaudan Sa | Derivados de butona úteis como agentes refrigerantes |
CN101677611A (zh) * | 2007-06-06 | 2010-03-24 | 吉万奥丹股份有限公司 | 盐增强 |
US8655677B2 (en) * | 2007-06-12 | 2014-02-18 | Bruce Reiner | Productivity workflow index |
ATE540667T1 (de) | 2007-06-13 | 2012-01-15 | Givaudan Sa | Verbindungen mit kühlender wirkung |
US7880011B2 (en) | 2007-07-23 | 2011-02-01 | Givandan, S.A. | Amide addition reaction |
EP2033688B1 (de) | 2007-08-20 | 2012-10-17 | Symrise AG | Oxalsäurederivate und deren Verwendung als physiologische Kühlwirkstoffe |
BRPI0817883A2 (pt) * | 2007-10-11 | 2014-10-07 | Mcneil Ppc Inc | Produto aprimorado de uso tópico para alivio de dores |
WO2009062332A2 (en) * | 2007-11-16 | 2009-05-22 | Givaudan Sa | Cooling compounds |
WO2009070910A2 (en) | 2007-12-07 | 2009-06-11 | Givaudan Sa | Carboxamide derivatieves having cooling properties |
WO2009076792A1 (en) | 2007-12-19 | 2009-06-25 | Givaudan Sa | Cooling compounds |
US20100297038A1 (en) * | 2008-01-17 | 2010-11-25 | Givaudan S.A. | Benzimidazole Derivatives And Their Use As Cooling Agents |
JP2011513236A (ja) * | 2008-02-22 | 2011-04-28 | ザ プロクター アンド ギャンブル カンパニー | 冷却剤を含むローション組成物を含む吸収性物品 |
DE102008015425A1 (de) * | 2008-03-20 | 2010-01-21 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen zur Verringerung von Juckreiz und anderen dermatologischen Missempfindungen, die insbesondere bei Altershaut auftreten können, mit einem Gehalt an (1R,2S,5R)-2-Isopropyl-5-methyl-N-(2-(pyridin-2-yl)ethyl-cyclohexancarboxamid und/oder (1R,2S,5R)-N-(4-(Cyanomethyl)-phenyl)-2-isopropyl-5-methylcyclohexancarboxamid |
DE102008015428A1 (de) * | 2008-03-20 | 2009-09-24 | Beiersdorf Ag | Kühlende Zubereitungen für den humanen Haut- und/oder Schleimhautkontakt mit einem Gehalt an (1R,2S,5R)-2-Isopropyl-5-methyl-N-(2-(pyridin-2-yl)ethyl-cyclohexancarboxamid und/oder (1R,2S,5R)-N-(4-(Cyanomethyl)-phenyl)-2-isopropyl-5-methylcyclohexancarboxamid |
DE102008015424A1 (de) * | 2008-03-20 | 2009-09-24 | Beiersdorf Ag | Kühlende kosmetische oder dermatologische Zubereitungen mit einem Gehalt an (1R,2S,5R)-2-Isopropyl-5-methyl-N-(2-(pyridyn-2-yl)ethyl-cyclohexancarboxamid und/oder (1R,2S,5R)-N-(4-(Cyanomethyl)-phenyl)-2-isopropyl-5- methylcyclohexancarboxamid mit Menthoxypropandiol |
DE102008015426A1 (de) | 2008-03-20 | 2009-09-24 | Beiersdorf Ag | Kühlende kosmetische oder dermatologische Zubereitungen mit einem Gehalt an (1R,2S,5R)-2-Isopropyl-5-methyl-N-(2-(pyridyn-2-yl)ethyl-cyclohexancarboxamid und/oder (1R,2S,5R)-N-(4-(Cyanomethyl)-phenyl)-2-isopropyl-5-methylcyclohexancarboxamid zu Reduktion von Hautrötungen |
JP2011520925A (ja) * | 2008-05-22 | 2011-07-21 | ジボダン エス エー | 清涼組成物 |
WO2010019730A1 (en) * | 2008-08-15 | 2010-02-18 | The Procter & Gamble Company | Synthesis of cyclohexane derivatives useful as sensates in consumer products |
WO2010019729A1 (en) | 2008-08-15 | 2010-02-18 | The Procter & Gamble Company | Solution of menthane carboxamides for use in consumer products |
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GB0504194D0 (en) | 2005-03-02 | 2005-04-06 | Givaudan Sa | Organic compounds |
MX2007010576A (es) | 2005-03-24 | 2007-10-04 | Givaudan Sa | Compuestos refrescantes. |
WO2006125334A1 (en) | 2005-05-27 | 2006-11-30 | Givaudan Sa | Cooling compounds |
US9452982B2 (en) | 2005-08-15 | 2016-09-27 | Givaudan, S.A. | Pyridinyl cyclohexanecarboxamide cooling compounds |
CA2692687C (en) | 2007-07-09 | 2021-10-26 | Bayer Bioscience N.V. | Brassica plant comprising mutant fatty acyl-acp thioesterase alleles |
WO2009070910A2 (en) | 2007-12-07 | 2009-06-11 | Givaudan Sa | Carboxamide derivatieves having cooling properties |
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2004
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- 2004-10-28 PL PL04761978T patent/PL1685093T6/pl unknown
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- 2004-10-28 EP EP04761978A patent/EP1685093B3/en active Active
- 2004-10-28 BR BRPI0416770-8A patent/BRPI0416770B1/pt active IP Right Grant
- 2004-10-28 CN CN200480033221A patent/CN100582089C/zh active Active
- 2004-10-28 ES ES04761978T patent/ES2342466T7/es active Active
- 2004-10-28 AT AT04761978T patent/ATE464283T1/de not_active IP Right Cessation
- 2004-10-28 JP JP2006540126A patent/JP4786544B2/ja active Active
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20170131432A (ko) * | 2015-03-25 | 2017-11-29 | 다카사고 고료 고교 가부시키가이샤 | 메틸멘톨 유도체 및 그것을 함유하는 냉감제 조성물 |
KR102404503B1 (ko) | 2015-03-25 | 2022-06-08 | 다카사고 고료 고교 가부시키가이샤 | 메틸멘톨 유도체 및 그것을 함유하는 냉감제 조성물 |
Also Published As
Publication number | Publication date |
---|---|
US20060276667A1 (en) | 2006-12-07 |
CN1878746A (zh) | 2006-12-13 |
JP2007511546A (ja) | 2007-05-10 |
PL1685093T3 (pl) | 2010-10-29 |
CN100582089C (zh) | 2010-01-20 |
ES2342466T7 (es) | 2012-11-19 |
ES2342466T3 (es) | 2010-07-07 |
PL1685093T6 (pl) | 2012-10-31 |
BRPI0416770B1 (pt) | 2014-05-13 |
USRE44339E1 (en) | 2013-07-02 |
US7414152B2 (en) | 2008-08-19 |
EP1685093A1 (en) | 2006-08-02 |
EP1685093B1 (en) | 2010-04-14 |
BRPI0416770A (pt) | 2007-02-27 |
DE602004026619D1 (en) | 2010-05-27 |
EP1685093B3 (en) | 2012-04-11 |
WO2005049553A1 (en) | 2005-06-02 |
ATE464283T1 (de) | 2010-04-15 |
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