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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- -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
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- 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)
- Birds (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Ceramic Products (AREA)
- Catalysts (AREA)
Description
本発明は、冷却化合物に関する。
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。
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。
ここで、このような化合物の特定の選択により、驚異的に強力であり、かつ長時間持続する冷却効果が示されることが見出された。従って、本発明は、式Ｉ
式中、ｍは、０または１であり、ＹおよびＺは、独立してＨ、ＯＨ、Ｃ１〜Ｃ４直鎖状もしくは分枝状アルキル、またはＣ１〜Ｃ４直鎖状もしくは分枝状アルコキシからなる群から選択され、Ｘは、（ＣＨ２）ｎ−Ｒであり、ここで、ｎは、０または１であり、Ｒは、非結合電子を有する基であり、ただし：
（ａ）ＹおよびＺがＨである場合、Ｘは、４位においてＦ、ＯＨ、ＭｅＯまたはＮＯ２ではなく、２または６位においてＯＨではなく、
（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。
（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。
好ましい化合物は、Ｘが４位にある化合物である。最も好ましい化合物は、Ｘが４位にあり、ＹおよびＺが、Ｈ、ＯＨ、ＭｅまたはＯＭｅである場合である。
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。
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。
この化合物を、容易に製造し、当該分野で認識されている方法により単離することができる。
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。
例えば、小グループのパネリストに、冷却化合物の種々の溶液を味見し、いずれの溶液が、２ｐｐｍのメントールの溶液と同様であるか、またはこれよりわずかに高い冷却強度を有するかを示すように依頼した。第２の実験において、同一のパネリストに、選択された濃度における溶液を味見し、口中で冷却を感じることができなくなるまで一定の時間間隔で冷却強度を記録するように依頼した。結果を、表１に示す。
表１から、式Ｉで表される化合物は、参照の冷却化合物であるメントールよりも１０倍まで強力であり、３倍まで長く継続することが、明らかである。式Ｉで表される化合物はまた、従来技術の最良の冷却化合物であるＷＳ−３よりもはるかに強力であり、長時間継続する。
本発明の化合物を、口または皮膚に適用されて冷却感覚を付与する製品において、用いることができる。「適用すること」により、接触されるすべての形態、例えば経口摂取または、タバコ製品の場合においては、吸入を意味する。皮膚への適用の場合において、これは、例えば、化合物を、クリームもしくは唾液中に、または噴霧可能な組成物中に導入することによることができる。従って、本発明はまた、口または皮膚に冷却効果を提供する方法であって、これに、上記に記載した化合物を含む製品を適用することによる、前記方法を提供する。
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。
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。
例１
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：
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：
例２
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の製造：
例１に記載したものと同様の製造により、以下の分光学的特性を有する所望の生成物が得られる：
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の製造：
例１に記載したものと同様の製造により、以下の分光学的特性を有する所望の生成物が得られる：
例３
Ｎ−（４−シアノフェニル）ｐ−メンタンカルボキサミドの製造：
例１に記載したものと同様の製造により、以下の分光学的特性を有する所望の生成物が得られる：
Ｎ−（４−シアノフェニル）ｐ−メンタンカルボキサミドの製造：
例１に記載したものと同様の製造により、以下の分光学的特性を有する所望の生成物が得られる：
例４
Ｎ−（４−アセチルフェニル）ｐ−メンタンカルボキサミドの製造：
例１に記載したものと同様の製造により、以下の分光学的特性を有する所望の生成物が得られる：
Ｎ−（４−アセチルフェニル）ｐ−メンタンカルボキサミドの製造：
例１に記載したものと同様の製造により、以下の分光学的特性を有する所望の生成物が得られる：
例５
Ｎ−（４−ヒドロキシメチルフェニル）ｐ−メンタンカルボキサミドの製造：
例１に記載したものと同様の製造により、以下の分光学的特性を有する所望の生成物が得られる：
Ｎ−（４−ヒドロキシメチルフェニル）ｐ−メンタンカルボキサミドの製造：
例１に記載したものと同様の製造により、以下の分光学的特性を有する所望の生成物が得られる：
例６
Ｎ−（３−ヒドロキシ−４−メトキシフェニル）ｐ−メンタンカルボキサミドの製造：
例１に記載したものと同様の製造により、以下の分光学的特性を有する所望の生成物が得られる：
Ｎ−（３−ヒドロキシ−４−メトキシフェニル）ｐ−メンタンカルボキサミドの製造：
例１に記載したものと同様の製造により、以下の分光学的特性を有する所望の生成物が得られる：
例７
洗口剤における適用
洗口剤における適用
成分を混合する。３０ｍＬの得られた溶液を、口中に含み、口内洗浄し、うがいし、吐き出す。強力な冷却が、口および唇のすべての領域において感じられる。冷却知覚は、数時間継続する。
例８
練り歯磨きにおける適用
練り歯磨きにおける適用
材料を、歯磨き用ゲル(toothgel)中で混合し、パネリストの歯を、歯磨き用ゲルを用いて磨く。口を、水で洗浄し、水を吐き出す。強力な冷却感覚が、パネリストにより、口のすべての領域において感じられる。冷却知覚は、数時間継続する。
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 |
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| Publication Number | Publication Date |
|---|---|
| JP2007511546A JP2007511546A (ja) | 2007-05-10 |
| JP2007511546A5 JP2007511546A5 (ja) | 2007-11-29 |
| JP4786544B2 true JP4786544B2 (ja) | 2011-10-05 |
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| Application Number | Title | Priority Date | Filing Date |
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| 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 |
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| 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) |
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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 |
|---|---|
| ES2342466T3 (es) | 2010-07-07 |
| EP1685093A1 (en) | 2006-08-02 |
| USRE44339E1 (en) | 2013-07-02 |
| JP2007511546A (ja) | 2007-05-10 |
| EP1685093B3 (en) | 2012-04-11 |
| US20060276667A1 (en) | 2006-12-07 |
| ATE464283T1 (de) | 2010-04-15 |
| CN1878746A (zh) | 2006-12-13 |
| BRPI0416770B1 (pt) | 2014-05-13 |
| WO2005049553A1 (en) | 2005-06-02 |
| PL1685093T3 (pl) | 2010-10-29 |
| US7414152B2 (en) | 2008-08-19 |
| DE602004026619D1 (en) | 2010-05-27 |
| CN100582089C (zh) | 2010-01-20 |
| EP1685093B1 (en) | 2010-04-14 |
| BRPI0416770A (pt) | 2007-02-27 |
| PL1685093T6 (pl) | 2012-10-31 |
| ES2342466T7 (es) | 2012-11-19 |
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