JP2007511546A - 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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- JP2007511546A JP2007511546A JP2006540126A JP2006540126A JP2007511546A JP 2007511546 A JP2007511546 A JP 2007511546A JP 2006540126 A JP2006540126 A JP 2006540126A JP 2006540126 A JP2006540126 A JP 2006540126A JP 2007511546 A JP2007511546 A JP 2007511546A
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- -1 N-substituted p-menthane carboxamides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 238000001816 cooling Methods 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000035597 cooling sensation Effects 0.000 abstract description 5
- 239000000463 material Substances 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
- 239000000203 mixture Substances 0.000 description 4
- 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
- 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 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
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 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
- 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 description 1
- 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 description 1
- 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 description 1
- 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 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)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Dermatology (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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Ceramic Products (AREA)
- Catalysts (AREA)
Abstract
で表される化合物は、口および皮膚に冷却感覚を付与する。式Iにおいて、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)3および5位における基は、4位における基がOHである場合にはOMeではなく、(iv)3および5位における基は、4位における基がメチルである場合にはOHではないようになっている。この化合物は、現在の最良の市販の物質よりも10倍まで強力な冷却感覚を付与する。
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 (5)
- 式I
(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。 - Xが4位にある、請求項1に記載の化合物。
- YおよびZが、H、OH、MeおよびOMeからなる群から選択される、請求項2に記載の化合物。
- Rが、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からなる群から選択される、請求項1に記載の化合物。
- 請求項1に記載の化合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 true JP2007511546A (ja) | 2007-05-10 |
JP2007511546A5 JP2007511546A5 (ja) | 2007-11-29 |
JP4786544B2 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 (11)
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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 |
JP2011520925A (ja) * | 2008-05-22 | 2011-07-21 | ジボダン エス エー | 清涼組成物 |
JP2011530608A (ja) * | 2008-08-15 | 2011-12-22 | ザ プロクター アンド ギャンブル カンパニー | 消費者製品における感覚剤として有用なシクロヘキサン誘導体の合成 |
JP2012508741A (ja) * | 2008-11-20 | 2012-04-12 | ザ プロクター アンド ギャンブル カンパニー | 冷涼感の強化をもたらすパーソナルケア組成物 |
JP2012524764A (ja) * | 2009-04-23 | 2012-10-18 | ヴェ.マン・フィス | 生理学的効果を有する化合物 |
JP2015533815A (ja) * | 2012-09-28 | 2015-11-26 | ザ ジレット カンパニー | 少なくとも1つの熱的弾性感覚剤を含む皮膚係合剃毛補助部材 |
JP2017514641A (ja) * | 2014-03-26 | 2017-06-08 | ザ ジレット カンパニー リミテッド ライアビリティ カンパニーThe Gillette Company Llc | 熱的弾性感覚剤を含む成形剃毛補助組成物を備えるかみそり |
KR20170131432A (ko) | 2015-03-25 | 2017-11-29 | 다카사고 고료 고교 가부시키가이샤 | 메틸멘톨 유도체 및 그것을 함유하는 냉감제 조성물 |
WO2018131575A1 (ja) | 2017-01-10 | 2018-07-19 | 高砂香料工業株式会社 | メチルメントール誘導体及びそれを含有する冷感剤組成物 |
WO2019078185A1 (ja) | 2017-10-16 | 2019-04-25 | 高砂香料工業株式会社 | 2,2,6-トリメチルシクロヘキサンカルボン酸誘導体を含有する冷感剤組成物 |
JP2020070263A (ja) * | 2018-11-01 | 2020-05-07 | ライオン株式会社 | 液体口腔用組成物 |
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BRPI0607407A2 (pt) * | 2005-03-01 | 2009-09-01 | Givaudan Sa | derivados de mentano carboxamida tendo propriedades de refrescáncia |
GB0504194D0 (en) * | 2005-03-02 | 2005-04-06 | Givaudan Sa | Organic compounds |
CN101184470A (zh) * | 2005-05-27 | 2008-05-21 | 吉万奥丹股份有限公司 | 清凉化合物 |
BRPI0616821B1 (pt) * | 2005-08-15 | 2022-06-07 | Givaudan Sa | Método para proporcionar um efeito refrescante em um produto e produto possuindo um efeito refrescante |
EP1940791B1 (en) * | 2005-10-25 | 2009-09-16 | Givaudan SA | Organic compounds |
CN101400636A (zh) * | 2006-03-15 | 2009-04-01 | 吉万奥丹股份有限公司 | 对位-取代的2-烷氧基苯酚化合物 |
US20090312384A1 (en) * | 2006-07-14 | 2009-12-17 | Stefan Michael Furrer | Benzimidazole As Cooling Compounds |
MX2009006695A (es) * | 2006-12-20 | 2009-09-14 | Givaudan Nederland Services B | P-mentan-3-carboxamida sustituida con nitrogeno y sus usos. |
GB0704163D0 (en) | 2007-03-02 | 2007-04-11 | Quest Int Serv Bv | Compositions comprising a physiological coolant |
US7935848B2 (en) | 2007-05-23 | 2011-05-03 | Givaudan S.A. | Butone derivatives useful as cooling agents |
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- 2004-10-28 BR BRPI0416770-8A patent/BRPI0416770B1/pt active IP Right Grant
- 2004-10-28 PL PL04761978T patent/PL1685093T6/pl unknown
- 2004-10-28 EP EP04761978A patent/EP1685093B3/en active Active
- 2004-10-28 DE DE602004026619T patent/DE602004026619D1/de active Active
- 2004-10-28 JP JP2006540126A patent/JP4786544B2/ja active Active
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JP2011520925A (ja) * | 2008-05-22 | 2011-07-21 | ジボダン エス エー | 清涼組成物 |
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Also Published As
Publication number | Publication date |
---|---|
PL1685093T3 (pl) | 2010-10-29 |
DE602004026619D1 (en) | 2010-05-27 |
ATE464283T1 (de) | 2010-04-15 |
EP1685093A1 (en) | 2006-08-02 |
ES2342466T7 (es) | 2012-11-19 |
CN1878746A (zh) | 2006-12-13 |
US20060276667A1 (en) | 2006-12-07 |
EP1685093B1 (en) | 2010-04-14 |
CN100582089C (zh) | 2010-01-20 |
ES2342466T3 (es) | 2010-07-07 |
BRPI0416770A (pt) | 2007-02-27 |
USRE44339E1 (en) | 2013-07-02 |
US7414152B2 (en) | 2008-08-19 |
WO2005049553A1 (en) | 2005-06-02 |
JP4786544B2 (ja) | 2011-10-05 |
EP1685093B3 (en) | 2012-04-11 |
BRPI0416770B1 (pt) | 2014-05-13 |
PL1685093T6 (pl) | 2012-10-31 |
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