ES2342466T7 - P-mentanocarboxamidas n-substituidas. - Google Patents
P-mentanocarboxamidas n-substituidas. Download PDFInfo
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- 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
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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)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Dermatology (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
DESCRIPCiÓN
P-mentancarboxamida N-sustituida y utilización de las P-mentancarboxamidas N-sustituidas
La presente invención se refiere a la utilización de ciertos compuestos para producir un efecto refrescante, según la reivindicación 1.
Los compuestos refrescantes, es decir, los compuestos químicos que proporcionan una sensación refrescante a la piel o las membranas mucosas del cuerpo, son bien conocidos en la técnica y son ampliamente utilizados en una variedad de productos, tales como alimentos, productos del tabaco, bebidas, dentífricos, enjuagues bucales y artículos de perfumería.
Una clase de compuestos refrescantes que han gozado de un éxito sustancial consiste en p-mentancarboxamidas N-substituidas. Se describen ejemplos de dichos compuestos, por ejemplo, en la patente británica GB 1.351.761-2 Y la patente de Estados Unidos US 4.150.052.
Ahora se ha descubierto que una selección particular de dichos compuestos presenta un efecto refrescante que es a la vez sorprendentemente intenso y duradero. En consecuencia, la presente invención da a conocer la utilización de un compuesto seleccionado entre el grupo que consiste en N-(4-cianometilfenil)-p-mentancarboxamida y N-(4cianofenil)-p-mentancarboxamida para la fabricación de un producto para proporcionar un efecto refrescante a la boca o a la piel, por la aplicación del producto a las mismas.
La invención da a conocer también el compuesto N-(4-cianometilfenil)-p-mentancarboxamida.
Dichos compuestos se pueden preparar y aislar fácilmente mediante métodos conocidos en la técnica.
Los mismos se distinguen de compuestos similares según la técnica anterior por su efecto refrescante sorprendentemente elevado (hasta 10 veces mayor que el de compuestos conocidos similares) y por la longevidad del efecto refrescante, hecho que hace aumentar su atractivo para una amplia variedad de productos.
Por ejemplo, se pidió a un pequeño grupo de evaluadores que probara diversas soluciones de compuestos refrescantes e indicara cuáles de ellas presentaban una intensidad de efecto refrescante similar o ligeramente superior a la de una solución de mentol a 2 ppm. En un segundo experimento, se pidió al mismo grupo de evaluadores que probara las soluciones en las concentraciones escogidas y registrara la intensidad de efecto refrescante en intervalos de tiempo regulares, hasta que no se pudiera notar ningún efecto refrescante en la boca. Los resultados se muestran en la tabla 1.
Tabla 1: experimento sobre la intensidad v lonaevidad del efecto refrescante
- Sustancia
- Concentración Longevidad
- 1-mentol
- 2,0 ppm 35 minutos
- N-etil-p-mentancarboxamida (WS-3)
- 1,5 ppm 57 minutos
- N-(4-ci anofeni I)-p-m entancarboxam ida
- 0,5 ppm 90 minutos
- N-( 4-cianometilfenil )-p-mentancarboxami da
- 0,2 ppm 93 minutos
A partir de la tabla 1, se puede observar que los compuestos son hasta 10 veces más intensos y duran hasta 3 veces más que el mentol, el compuesto refrescante de referencia. Los compuestos también son mucho más intensos y duran más que el WS-3, el mejor compuesto refrescante según la técnica anterior.
Los compuestos se pueden utilizar en productos que se aplican a la boca o la piel a efectos de producir una sensación refrescante. El término "aplicar" se refiere a cualquier forma de poner en contacto, por ejemplo, ingestión oral o, en el caso de los productos del tabaco, inhalación. En el caso de la aplicación a la piel, la misma se puede producir, por ejemplo, incluyendo el compuesto en una crema o ungüento, o en una composición pulverizable. En consecuencia, la presente invención también da a conocer la utilización de un compuesto, tal como se ha descrito anteriormente, para la preparación de un producto que proporciona un efecto refrescante en la boca o la piel al aplicar dicho producto a las mismas.
A continuación, la presente invención se describe haciendo referencia a los siguientes ejemplos no limitantes, que describen realizaciones preferentes de la misma.
Ejemplo 1
Preparación de N-(4-cianometilfenil)-p-mentancarboxamida
Se introdujeron en un matraz 6,6 g (50 mmol) de cianuro de 4-aminobencilo, 4,04 mi de piridina y 100 mi de MtBE. A
esta mezcla, se añadieron gota a gota 10 g de cloruro de p-mentanocarboxilo durante 5 minutos. La mezcla de
reacción se agitó durante 24 h. A la mezcla de reacción se añadieron 50 mi de agua. La mezcla se separó. La capa
orgánica se lavó con 50 mi de agua y 50 mi de solución saturada de cloruro sódico. La capa orgánica se secó sobre
MgS04. El disolvente se evaporó en vacío a efectos de obtener el producto crudo, que se recristalizó en hexanos,
obteniéndose 10,1 g del producto deseado con las siguientes propiedades espectroscópicas:
EM: 299 ([M+1]), 298 ([M+]), 132,83
1H RMN (300 MHz; CDCI3) ó: 7,58 (d, 2H), 7,49 (s, 1 H), 7,27 (d, 2H), 3,73 (s, 2H), 2,2 (t, 1 H), 1,96-1,57 (m, 5H),
1,48-1,21 (m, 2H), 1,172-0,99 (m, 2H), 0,94 (d, 3H), 0,93 (d, 3H), 0,85 (d, 3H)
13C RMN (75 MHz; CDCI3) ó: 174,4, 137,8, 128,3, 125,1, 120,3, 118,2,50,5,44,3,39,25,34,3,32,1,28,7,23,8,22,9,
22,1,21,2,16,1
Ejemplo 2
Preparación de N-(4-cianofenil)-p-mentancarboxamida;
Una preparación similar a la descrita en el ejemplo 1 da lugar al producto deseado con las siguientes propiedades espectroscópicas:
EM: 285([M+1]), 284 ([M+]), 139,83 1H RMN (300 MHz; CDCI3) ó: 7,69 (d, 2H), 7,6 (d, 2H), 7,5 (s, 1H), 1,85-1,97 (m, 1H), 1,69-1,84 (m, 3H), 1,55-1,69 1m, 2H), 1,21-1,47 (m, 2H), 0,979-1,16 (m, 2H), 0,95 (d, 3H), 0,93 (d, 3H), 0,82 (d, 3H)
3C RMN (300 MHz; CDCI3) ó: 174,6, 133,1, 119,4, 118,7, 100,35, 50,7,44,4,39,25,34,2,32,1,28,8,23,7,22,0, 21,2,16,1,14,0
Ejemplo 3
Aplicación en enjuague bucal
- Alcohol 95%
- 177 mi
- Sorbitol 70%
- 250 g
- Compuesto según el ejemplo 1 como solución al 1%
- en alcohol 50 mi
- Aceite de menta, sin terpenos
- 0,300 g
- Salicilato de metilo
- 0,640 g
- Eucaliptol
- 0,922 g
- Timol
- 0,639 g
- Ácido benzoico
- 1,500 g
- Pluronic™ F127
- 5,000 g
- Sacarina sódica
- 0,600 g
- Citrato sódico
- 0,300 g
- Ácido cítrico
- 0,100 g
- Agua
- c.s. hasta 1 litro
Los ingredientes se mezclan. Se introducen en la boca 30 mi de la solución obtenida, con la misma se enjuaga, se hacen gárgaras y finalmente se escupe. Se experimenta un intenso efecto refrescante en todas las zonas de la boca, así como en los labios. Dicha sensación refrescante dura diversas horas.
Claims (2)
- REIVINDICACIONES1. Utilización de un compuesto seleccionado entre el grupo que consiste en N-(4-cianometilfenil)-pmentancarboxamida y N-(4-cianofenil)-p-mentancarboxamida para la preparación de un producto que proporciona un efecto refrescante en la boca o en la piel al aplicar dicho producto a las mismas.
- 2. N-(4-cianometilfenil)-p-mentancarboxamida.
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 (es) |
EP (1) | EP1685093B3 (es) |
JP (1) | JP4786544B2 (es) |
CN (1) | CN100582089C (es) |
AT (1) | ATE464283T1 (es) |
BR (1) | BRPI0416770B1 (es) |
DE (1) | DE602004026619D1 (es) |
ES (1) | ES2342466T7 (es) |
PL (1) | PL1685093T6 (es) |
WO (1) | WO2005049553A1 (es) |
Families Citing this family (179)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7868004B2 (en) * | 2005-03-01 | 2011-01-11 | Givaudan S.A. | Menthane carboxamide derivatives having cooling properties |
GB0504194D0 (en) | 2005-03-02 | 2005-04-06 | Givaudan Sa | Organic compounds |
WO2006125334A1 (en) * | 2005-05-27 | 2006-11-30 | Givaudan Sa | Cooling compounds |
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2004
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- 2004-10-28 WO PCT/CH2004/000646 patent/WO2005049553A1/en not_active Application Discontinuation
- 2004-10-28 PL PL04761978T patent/PL1685093T6/pl unknown
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JP4786544B2 (ja) | 2011-10-05 |
ATE464283T1 (de) | 2010-04-15 |
US20060276667A1 (en) | 2006-12-07 |
US7414152B2 (en) | 2008-08-19 |
DE602004026619D1 (en) | 2010-05-27 |
EP1685093B1 (en) | 2010-04-14 |
EP1685093A1 (en) | 2006-08-02 |
EP1685093B3 (en) | 2012-04-11 |
PL1685093T3 (pl) | 2010-10-29 |
BRPI0416770A (pt) | 2007-02-27 |
BRPI0416770B1 (pt) | 2014-05-13 |
ES2342466T3 (es) | 2010-07-07 |
WO2005049553A1 (en) | 2005-06-02 |
CN1878746A (zh) | 2006-12-13 |
JP2007511546A (ja) | 2007-05-10 |
CN100582089C (zh) | 2010-01-20 |
PL1685093T6 (pl) | 2012-10-31 |
USRE44339E1 (en) | 2013-07-02 |
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