ES2342466T7 - P-mentanocarboxamidas n-substituidas. - Google Patents
P-mentanocarboxamidas n-substituidas. Download PDFInfo
- Publication number
- ES2342466T7 ES2342466T7 ES04761978T ES04761978T ES2342466T7 ES 2342466 T7 ES2342466 T7 ES 2342466T7 ES 04761978 T ES04761978 T ES 04761978T ES 04761978 T ES04761978 T ES 04761978T ES 2342466 T7 ES2342466 T7 ES 2342466T7
- Authority
- ES
- Spain
- Prior art keywords
- compounds
- group
- cooling effect
- groups
- positions
- Prior art date
- Legal status (The legal status 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 status listed.)
- Active
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- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 238000001816 cooling Methods 0.000 claims abstract description 15
- 230000000694 effects Effects 0.000 claims description 12
- -1 4-cyanomethylphenyl Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 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 4
- 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 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 3
- VUNOFAIHSALQQH-UHFFFAOYSA-N Ethyl menthane carboxamide Chemical compound CCNC(=O)C1CC(C)CCC1C(C)C VUNOFAIHSALQQH-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229940041616 menthol Drugs 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000035807 sensation Effects 0.000 description 2
- 235000019505 tobacco product Nutrition 0.000 description 2
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical compound NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 229960005233 cineole Drugs 0.000 description 1
- 230000035597 cooling sensation Effects 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
- 235000013305 food Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 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)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Ceramic Products (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52397703P | 2003-11-21 | 2003-11-21 | |
| US523977P | 2003-11-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2342466T3 ES2342466T3 (es) | 2010-07-07 |
| ES2342466T7 true ES2342466T7 (es) | 2012-11-19 |
Family
ID=34619622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04761978T Active ES2342466T7 (es) | 2003-11-21 | 2004-10-28 | P-mentanocarboxamidas n-substituidas. |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7414152B2 (https=) |
| EP (1) | EP1685093B3 (https=) |
| JP (1) | JP4786544B2 (https=) |
| CN (1) | CN100582089C (https=) |
| AT (1) | ATE464283T1 (https=) |
| BR (1) | BRPI0416770B1 (https=) |
| DE (1) | DE602004026619D1 (https=) |
| ES (1) | ES2342466T7 (https=) |
| PL (1) | PL1685093T6 (https=) |
| WO (1) | WO2005049553A1 (https=) |
Families Citing this family (185)
| 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 |
| MX2007014456A (es) * | 2005-05-27 | 2008-02-07 | Givaudan Sa | Compuestos refrescantes. |
| WO2007019719A1 (en) | 2005-08-15 | 2007-02-22 | Givaudan Sa | Cooling compounds |
| US8263046B2 (en) | 2005-10-25 | 2012-09-11 | Givaudan S.A. | N-phenyl-N-pyridinyl-benzamides and benzenesulfonomides having cooling properties |
| BRPI0709393A2 (pt) * | 2006-03-15 | 2011-07-05 | Givaudan Sa | compostos 2-alcoxifenóis para -substituìdos, uso dos mesmos, método de fornecer um efeito refrescante à boca ou pele e produto contendo ditos compostos |
| EP2040666B1 (en) * | 2006-07-14 | 2010-01-20 | Givaudan SA | Benzimidazoles as cooling compounds |
| BRPI0721140A2 (pt) * | 2006-12-20 | 2014-04-01 | Givaudan Nederland Services Bv | P-mentano-3-carboxamida n-substituída e usos da mesma. |
| GB0704163D0 (en) | 2007-03-02 | 2007-04-11 | Quest Int Serv Bv | Compositions comprising a physiological coolant |
| EP2155151B1 (en) | 2007-05-23 | 2013-07-31 | Givaudan SA | Butanone derivatives and use thereof as cooling agents |
| WO2008148234A1 (en) * | 2007-06-06 | 2008-12-11 | Givaudan Sa | Salt enhancement |
| 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 |
| KR20100093040A (ko) * | 2007-10-11 | 2010-08-24 | 맥네일-피피씨, 인코포레이티드 | 개선된 국소 통증 완화 제품 |
| WO2009062332A2 (en) * | 2007-11-16 | 2009-05-22 | Givaudan Sa | Cooling compounds |
| US8377422B2 (en) | 2007-12-07 | 2013-02-19 | Givaudan S.A. | Carboxamide derivatives 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 |
| MX2010009139A (es) * | 2008-02-22 | 2010-09-14 | Procter & Gamble | Articulo absorbente que comprende una composicion de locion con un agente de enfriamiento. |
| 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 |
| 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 |
| 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 |
| 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 |
| EP2296759B1 (en) * | 2008-05-22 | 2019-10-02 | Givaudan SA | Cooling composition |
| BRPI0917997A2 (pt) | 2008-08-15 | 2015-11-17 | Procter & Gamble | solução de mentanocarboxamidas para uso em produtos destinados ao consumidor |
| MX2011001724A (es) * | 2008-08-15 | 2011-03-21 | Procter & Gamble | Sintesis de derivados de ciclohexano utiles como agentes de sensacion en productos de consumo. |
| EP2346475B2 (en) * | 2008-11-20 | 2023-04-19 | The Procter & Gamble Company | Personal care compositions providing enhanced cooling sensation |
| FR2944790B1 (fr) * | 2009-04-23 | 2012-06-01 | Mane Fils V | Nouveaux composes a effet physiologique |
| US7923577B2 (en) | 2009-04-27 | 2011-04-12 | International Flavors & Fragrances Inc. | Menthylcarboxamides and their use as cooling agents |
| WO2010128026A2 (en) | 2009-05-05 | 2010-11-11 | Givaudan Sa | Organic compounds |
| SG178050A1 (en) | 2009-07-29 | 2012-03-29 | 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 |
| EP2295031B1 (de) | 2009-08-05 | 2018-01-10 | Symrise AG | Verwendung von Pterocarpanen als Anti-Cellulite-Wirkstoffe |
| CN102802732B (zh) | 2009-09-11 | 2016-04-27 | 宝洁公司 | 用于口腔表面疏水改性的方法和组合物 |
| US20110195042A1 (en) * | 2010-02-10 | 2011-08-11 | Thomas Edward Huetter | Compositions, Methods and Kits Useful for Treating a Respiratory Symptom |
| MX343550B (es) | 2010-04-01 | 2016-11-08 | The Procter & Gamble Company * | Control del mal olor en toda la boca con una combinacion de agentes antibacterianos y desodorizantes. |
| JP5714694B2 (ja) | 2010-04-08 | 2015-05-07 | シムライズ アーゲー | ジヒドロデヒドロジイソオイゲノールの使用およびジヒドロデヒドロジイソオイゲノールを含む製剤 |
| EP2389922A1 (en) | 2010-05-25 | 2011-11-30 | Symrise AG | Cyclohexyl carbamate compounds as anti-ageing actives |
| US20120014883A1 (en) | 2010-07-19 | 2012-01-19 | Douglas Craig Scott | Compositions Comprising Derivatives Of Essential Oil Compounds And Use In Personal Care Products |
| WO2012034012A1 (en) | 2010-09-09 | 2012-03-15 | Kraft Foods Global Brands Llc | Chewing gum compositions providing flavor release profiles |
| US9937115B2 (en) | 2010-10-01 | 2018-04-10 | The Procter & Gamble Company | Oral care compositions with improved flavor |
| US20120116113A1 (en) | 2010-11-05 | 2012-05-10 | Erman Mark B | PROCESS FOR MAKING NEO-ENRICHED p-MENTHANE COMPOUNDS |
| EP2286908A3 (de) | 2010-11-19 | 2011-06-01 | Symrise AG | Lösungsvermittler für kosmetische Zubereitungen |
| EP2356977B1 (de) | 2011-02-02 | 2017-12-27 | Symrise AG | Zubereitungen mit Holzextrakten von Gleditschien |
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- 2004-10-28 JP JP2006540126A patent/JP4786544B2/ja not_active Expired - Lifetime
- 2004-10-28 AT AT04761978T patent/ATE464283T1/de not_active IP Right Cessation
- 2004-10-28 ES ES04761978T patent/ES2342466T7/es active Active
- 2004-10-28 BR BRPI0416770-8A patent/BRPI0416770B1/pt not_active IP Right Cessation
- 2004-10-28 DE DE602004026619T patent/DE602004026619D1/de not_active Expired - Lifetime
- 2004-10-28 PL PL04761978T patent/PL1685093T6/pl unknown
- 2004-10-28 EP EP04761978A patent/EP1685093B3/en not_active Expired - Lifetime
-
2006
- 2006-05-19 US US11/437,294 patent/US7414152B2/en not_active Ceased
-
2011
- 2011-08-31 US US13/222,947 patent/USRE44339E1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2342466T3 (es) | 2010-07-07 |
| ATE464283T1 (de) | 2010-04-15 |
| EP1685093B3 (en) | 2012-04-11 |
| US20060276667A1 (en) | 2006-12-07 |
| PL1685093T6 (pl) | 2012-10-31 |
| CN1878746A (zh) | 2006-12-13 |
| BRPI0416770B1 (pt) | 2014-05-13 |
| BRPI0416770A (pt) | 2007-02-27 |
| US7414152B2 (en) | 2008-08-19 |
| CN100582089C (zh) | 2010-01-20 |
| USRE44339E1 (en) | 2013-07-02 |
| EP1685093A1 (en) | 2006-08-02 |
| JP2007511546A (ja) | 2007-05-10 |
| EP1685093B1 (en) | 2010-04-14 |
| PL1685093T3 (pl) | 2010-10-29 |
| WO2005049553A1 (en) | 2005-06-02 |
| DE602004026619D1 (en) | 2010-05-27 |
| JP4786544B2 (ja) | 2011-10-05 |
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