BRPI0416770B1 - P-mentano carbosamidado n-substituído - Google Patents

P-mentano carbosamidado n-substituído Download PDF

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BRPI0416770B1
BRPI0416770B1 BRPI0416770-8A BRPI0416770A BRPI0416770B1 BR PI0416770 B1 BRPI0416770 B1 BR PI0416770B1 BR PI0416770 A BRPI0416770 A BR PI0416770A BR PI0416770 B1 BRPI0416770 B1 BR PI0416770B1
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menthanecarboxamide
cooling
group
compounds
groups
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BRPI0416770-8A
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Galopin Christophe
Tigani Lori
Victor Krawec Pablo
Patrick Slack Jay
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Givaudan Sa
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    • 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)
  • 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)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Ceramic Products (AREA)
  • Catalysts (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

Description

Relatório Descritivo da Patente de invenção para "P-MENTANO CARBOSAMIDADO N-SUBSTITUÍDO". A presente invenção refere-se a compostos de resfriamento.
Compostos de resfriamento, isto é, compostos químicos que conferem uma sensação de resfriamento à pele ou a membranas mucosas do corpo, são bem conhecidos pela técnica e são amplamente usados em diversos produtos tais como gêneros alimentícios, produtos de tabaco, bebi- das, dentifrícios, anti-sépticos bucais e sanitários.
Uma classe de compostos de resfriamento que gozou de subs- tancial sucesso consiste em carboxamidas de p-mentano N-substituído. E- xemplos destes compostos são descritos em, por exemplo, na Patente Britâ- nica GB 1.351.761-2 e Patente dos Estados Unidos n° 4.150.052.
Foi atualmente descoberto que uma seleção particular de tais compostos exibe um efeito de resfriamento que é igualmente surpreenden- temente forte e de longa duração. A invenção, portanto, fornece um compos- to da fórmula I em que m é 0 ou 1, Y e Z são independentemente selecionados do grupo que consiste em H, OH, C1-C4 aíquila linear ou ramificada, ou, um C1-C4 al- cóxi linear ou ramificado, X é (CH2)n'R, onde n é 0 ou 1 e R é um grupo com elétrons não-ligados, com a condição de que: (a) quando Y e Z forem Η, X não seja F, OH, MeO ou N02 na posição 4 e não seja OH na posição 2 ou 6; (b) quando Y ou Z for H, então X, Y e Z sejam tal que (i) os grupos nas posições 3 e 4 não sejam ambos OMe, (ii) os grupos nas posições 4 e 5 não sejam ambos OMe, (iii) os grupos nas posições 3 e 5 não sejam OMe se 0 grupo na posição 4 for OH, e (iv) os grupos nas posições 3 e 5 não sejam OH se o gru- po na posição 4 for metila.
Os compostos preferidos são aqueles em que X está na posição 4. Os compostos mais preferidos são quando X está na posição 4 e Y e Z são H, OH, Me ou OMe.
Os grupos preferidos com elétrons não- ligados são halogênios, OH, OMe, N02, CN, Ac, S02NH2, CHO, C02H e carboxilatos de C1-C4 alqui- la tais como C02Et.
Os compostos podem ser facilmente preparados e isolados por métodos reconhecidos na técnica.
Eles são distingüidos de compostos similares da técnica anterior por seu efeito de resfriamento surpreendentemente elevado (até 10 vezes maior do que aquele de compostos similares conhecidos) e pela longevidade do efeito de resfriamento, que adiciona a seus atrativos em uma larga varie- dade de produtos.
Por exemplo, um pequeno grupo de analistas foi solicitado para provar várias soluções de compostos de resfriamento e indicar que as solu- ções tinham uma intensidade de resfriamento similar ou ligeiramente maior do que aquela de uma solução de mentol a 2 ppm. Em um segundo experi- mento, ao mesmo analista foi solicitado provar as soluções nas concentra- ções escolhidas e registrar a intensidade de resfriamento em intervalos de tempo regulares até que nenhum resfriamento pudesse ser sentido na boca.
Os resultatos são mostrados na tabela 1.
Tabela 1 experimento sobre a longevidade e intensidade de resfriamento.
Da Tabela 1, pode-se observar que os compostos de Fórmula I são até 10 vezes mais fortes e permanecem até 3 vezes mais tempo do que 0 mentol, 0 composto de resfriamento de referência. Os compostos de Fór- mula I são também muito mais fortes e permanecem mais tempo do que o WS-3, o melhor composto de resfriamento da técnica anterior.
Os compostos da invenção podem ser usados em produtos que são aplicados à boca ou à pele para fornecer uma sensação de resfriamento.
Por "aplicando" entende-se qualquer forma de trazer em contato, por exemplo, ingestão oral ou, no caso de produtos de tabaco, inalação. No caso de apli- cação à pele, pode ser, por exemplo, incluindo o composto em um creme ou pomada, ou em uma composição vaporizável. A invenção, portanto, também fornece um método de fornecer um efeito de resfriamento à boca ou pele aplicando-se a ela um produto compreendendo um composto como acima descrito. A invenção é agora também descrita por meio dos seguintes exemplos não-limitantes, que descrevem as modalidades preferidas.
Exemplo 1 Preparação de p-mentanocarboxamida de N-(4-cianometil- fenila). A um frasco, foram adicionados 6,6 g (50 mmoles) de cianeto de 4-aminobenzila, 4,04 mL de piridina e 100 mL de MtBE. A esta mistura, 10 g de cloreto de p-mentanocarboxila foram adicionados por em gotas durante 5 minutos. A mistura de reação foi agitada por 24 horas. À mistura de reação, 50 mL de água foram adicionados. A mistura foi separada. A camada orgâ- nica foi lavada com 50 mL de água e 50 mL de salmoura. A camada orgâni- ca foi seca em MgSO* O solvente foi evaporado em vácuo para fornecer o produto bruto, que foi recristalizado de hexanos para fornecer 10,1 g do pro- duto desejado com as seguintes propriedades espectroscópicas: MS: 299 ([M+1]), 298 ([M+]), 132, 83 1H RMN (300 MHz; CDCI3) δ: 7,58 (d, 2H), 7,49 (s, 1 H), 7,27 (d, 2 H), 3,73 (s, 2 H), 2,2 (t, 1 H), 1,96 - 1,57 (m, 5 H), 1,48 - 1,21 (m, 2H), 1.172 - 0,99 (m, 2H), 0,94 (d, 3 H), 0,93 (d, 3 H), 0,85 (d, 3 H). 13C RMN (75 MHz; CDCI3) δ: 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.
Exemplo 2 Preparação de p-mentanocarboxamida de N-(4-sulfamoil- fenila): Uma preparação similar àquela descrita no exemplo 1 fornece o produto desejado com as seguintes propriedades espectroscópicas: MS: 339 ([M+1]), 338 ([M+]), 172,83 1H RMN (300 MHz; DMSO) δ: 10,21 (s, 1 H), 7,76 (d, 1 H) 7,73 (d, 2 H), 7,23 (s, 2 H), 2,26-2,42 (m, 1 H), 1,45 - 1,85 (m, 5 H), 1,29 -1,44 (m, 2 H), 0,89 (d, 3H), 0,86 (d, 3 H), 0,78 (d, 3 H). 13C RMN (75 MHz; DMSO) δ: 174,6, 142,3, 138,3,126,7, 118,8, 48,9, 43,7, 34,3, 31,9, 28,6,23,7, 22,35, 21,3,16,25 .
Exemplo 3 Preparação de p-mentanocarboxamida de N-(4-cianofenila): Uma preparação similar àquela descrita no exemplo 1 fornece o produto desejado com as seguintes propriedades espectroscópicas: MS: 285 ([M+1]), 284 ([M+]), 139,83. 1H RMN (300 MHz; CDCI3) δ: 7,69 (d, 2 H), 7,6 (d, 2 H), 7,5 (s, 1 H), 1,85 -1,97 (m, 1 H), 1,69 - 1,84 (m, 3 H), 1,55 - 1,69 (m, 2 H), 1,21 -1,47 (m, 2 H), 0,979 -1,16 (m, 2 H), 0,95 (d, 3 H), 0,93 (d, 3 H), 0,82 (d, 3 H). 13C RMN (300 MHz; CDCI3) δ: 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 .
Exemplo 4 Preparação de p-mentanocarboxamida de N-(4-acetilfenila): Uma preparação similar àquela descrita no exemplo 1 fornece o produto desejado com as seguintes propriedades espectroscópicas: MS: 302 ([M+1]), 301 ([M+]), 135,83 1H RMN (300 MHz; CDCI3) δ: 7,93 (d, 2 H), 7,66 (d, 2 H), 7,63 (s, 1 H), 2,57 (s, 3 H), 2,09 - 2,31 (m, 1 H), 1,84 -1,98 (m, 1H), 1,68 -1,85 (m, 5 H), 1,56 -1,68 (m, 1 H), 1,17 -1,48 (m, 2 H), 0,93 (d, 3 H), 0,91 (d, 3 H), 0,83 (d, 3 H). 13C RMN (75 MHz; CDCI3) δ: 197,1, 174,9, 142,7, 129,9,119,2, 51,2, 44,9,39,8, 34,8, 32,6,29,2, 26,6, 24,3,22,4,21,5,16,6 .
Exemplo 5 Preparação de p-mentanocarboxamida de N-(4-hidroxime- tilfenila): Uma preparação similar àquela descrita no exemplo 1 fornece o produto desejado com as seguintes propriedades espectroscópicas: MS: 290 (M+1), 289 (M+), 123,83 1HRMN (300 MHz, DMSO) δ: 9,9 (s, 1 H), 7,54 (d, 2 H), 7,21 (d, 2 H), 4,2 (s, 2H), 2,36 - 2,1 (m, 1 H), 1,8 -1,59 (m, 6 H), 1,57 - 1,44 (m, 1 H), 1,21 - 0,9 (m, 4H), 0,87 (dd, 3 H), 0,85 (dd, 3 H), 0,79 (d, 2H). 13C RMN (75 MHz; DMSO) 8: 173,7, 137,7,137,1, 126,7, 118,9, 62,6, 48,6, 43,6, 34,2,31,7,28,3, 23,6,22,2, 21,1, 16,1.
Exemplo 6 Preparação de p-mentanocarboxamida de N-(3-hidróxi-4- metoxifenila): Uma preparação similar àquela descrita no exemplo 1 fornece o produto desejado com as seguintes propriedades espectroscópicas: MS: 306 ([M+1]), 305 ([M+]), 139,83 1H RMN (300 MHz; CDCI3) δ: 7,14 (s, 1H), 7,08 (d, 1H), 6,78 (d, 1H), 5,7 (s, 1H), 3,8 (s, 3H), 2,02 - 2,21 (m, 2 H), 1,53 - 1,94 (m, 5 H), 1,17 - 1,48 (m, 2H), 0,97 -1,17 (m, 2 H), 0,92 (dd, 3 H), 0,91 (dd, 3 H), 0,82 (d, 3H). 13C RMN (75 MHz; CDCI3) δ: 173,9,145,6,143,3,131,7,111,65, 110,8,107,4, 56,1, 50,5, 44,4, 39,2, 32,15, 34,4, 28,6, 23,8, 22,1,21,2,16,1.
Exemplo 7 Aplicação em anti-séptico bucal Álcool 95% 177 mL
Sorbitol 70% 250 g Composto de exemplo 1, como uma solução a 1 % em álcool 50 mL Óleo de hortelã-pimenta, sem terpeno 0,300 g Salicilato de metila 0,640 g Eucaliptol 0,922 g Timol 0,639 g Ácido benzóico 1,500 g Pluronic® F127 5,000 g Sacarina sódica 0,600 g Citrato de sódio 0,300 g Ácido cítrico 0,100 g Água q.s. 1 litro Os ingredientes são misturados. 30 mL de solução obtida são colocados na boca, sacudidos ao redor, gargarejados e cuspidos. Um inten- so resfriamento é sentido em toda a área da boca assim como dos lábios. A percepção de resfriamento permanece por várias horas.
Exemplo 8 Aplicação em pasta de dente Gel dental opaco 97,000 g Composto de exemplo 2, como uma solução a 2% em PG 2,500g Óleo de hortelã-pimenta, sem terpeno 0,500g Os materiais são misturados no gel dental, e os dentes do ana- lista são escovados usando esse gel dental. A boca é enxaguada com água e a água cuspida. Uma intensa sensação de resfriamento é sentida pelo analista em todas as áreas da boca. A percepção de resfriamento permane- ce por várias horas.

Claims (6)

1. Composto, caracterizado pelo fato de que é selecionado do grupo que consiste em N-(4-cianometilfenil) p-mentanocarboxamida, N-(4- sulfamoilfenil) p-mentanocarboxamida e N-(3-hidroxi-4-metoxifenil) p- mentanocarboxamida.
2. Composto de acordo com a reivindicação 1, caracterizado pelo fato de que é N-(4-cianometilfenil) p-mentanocarboxamida.
3. Método de fornecer um efeito de resfriamento à boca ou pele, caracterizado pelo fato de que se aplica a ela um produto compreendendo um composto selecionado do grupo que consiste em N-(4-cianometilfenil) p- mentanocarboxamida, N-(4-sulfamoilfenil) p-mentanocarboxamida, N-(4- cianofenil) p-mentanocarboxamida, N-(4-acetilfenil) p-mentanocarboxamida, N-(4- hidroximetilfenil) p-mentanocarboxamida e N-(3-hidroxi-4-metoxifenil) p-mentanocarboxamida.
4. Método de acordo com a reivindicação 3, caracterizado pelo fato de que a dita aplicação compreende inalação.
5. Método de acordo com a reivindicação 3, caracterizado pelo fato de que a dita aplicação compreende ingestão oral.
6. Método de acordo com a reivindicação 3, caracterizado pelo fato de que é N-(4-cianometilfenil) p-mentanocarboxamida.
BRPI0416770-8A 2003-11-21 2004-10-28 P-mentano carbosamidado n-substituído BRPI0416770B1 (pt)

Applications Claiming Priority (3)

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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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BRPI0416770B1 true BRPI0416770B1 (pt) 2014-05-13

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EP (1) EP1685093B3 (pt)
JP (1) JP4786544B2 (pt)
CN (1) CN100582089C (pt)
AT (1) ATE464283T1 (pt)
BR (1) BRPI0416770B1 (pt)
DE (1) DE602004026619D1 (pt)
ES (1) ES2342466T7 (pt)
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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
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JP2009529545A (ja) * 2006-03-15 2009-08-20 ジボダン エス エー パラ置換２−アルコキシフェノール化合物
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CN1878746A (zh) 2006-12-13
PL1685093T3 (pl) 2010-10-29
EP1685093B3 (en) 2012-04-11
CN100582089C (zh) 2010-01-20
USRE44339E1 (en) 2013-07-02
EP1685093B1 (en) 2010-04-14
ES2342466T3 (es) 2010-07-07
PL1685093T6 (pl) 2012-10-31
WO2005049553A1 (en) 2005-06-02
ATE464283T1 (de) 2010-04-15
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US7414152B2 (en) 2008-08-19
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