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CN100582089C - N-取代的对-薄荷烷甲酰胺 - Google Patents

N-取代的对-薄荷烷甲酰胺 Download PDF

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CN100582089C
CN100582089C CN200480033221A CN200480033221A CN100582089C CN 100582089 C CN100582089 C CN 100582089C CN 200480033221 A CN200480033221 A CN 200480033221A CN 200480033221 A CN200480033221 A CN 200480033221A CN 100582089 C CN100582089 C CN 100582089C
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CN1878746A (zh
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C·加洛潘
P·V·克拉维克
J·P·斯拉克
L·蒂加尼
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    • 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
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
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    • 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
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • 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
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    • 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
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    • 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
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    • 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
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
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    • 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
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Abstract

式(I)化合物给口腔和皮肤提供清凉感觉。在式I中，m是0或1，Y和Z独立地选自H、OH、C1-C4直链或支链烷基，或C1-C4直链或支链烷氧基，X是(CH2)n-R，其中n是0或1并且R是具有非成键电子的基团，前提条件是：(a)当Y和Z是H时，X在第4位不是F、OH、MeO或NO2并且在第2或6位不是OH；(b)当Y或Z是H时，则X、Y和Z是使：(i)第3和4位的基团不同时是OMe，(ii)第4和5位的基团不同时是OMe，(iii)如果第4位的基团是OH，则第3和5位的基团不是OMe，且(iv)如果第4位的基团是甲基，则第3和5位的基团不是OH。该化合物可提供比目前最好的商购物料强最多十倍有效的清凉感觉。

Description

N-取代的对-薄荷烷甲酰胺
本发明涉及清凉化合物。
清凉化合物，即给身体皮肤或粘膜赋予清凉感觉的化学化合物，是本领域所公知的并且广泛用于各种各样的产品如食物、烟草制品、饮料、牙粉、漱口剂和盥洗用品中。
获得巨大成功的一类清凉化合物是由N-取代的对-薄荷烷甲酰胺组成。这些化合物的实例在例如英国专利GB 1,351,761-2和美国专利US 4,150,052中有描述。
现已发现，特定选择的这类化合物可显出既出人意料地强烈又长效持续的清凉效果。因此，本发明提供下式I的化合物：
其中m是0或1，Y和Z独立地选自H、OH、C1-C4直链或支链烷基，或C1-C4直链或支链烷氧基，X是(CH2)n-R，其中n是0或1并且R是具有非成键电子的基团，前提条件是：
(a)当Y和Z是H时，X在第4位不是F、OH、MeO或NO2并且在第2或6位不是OH
(b)当Y或Z是H时，则X、Y和Z是使：
(i)第3和4位的基团不同时是OMe，
(ii)第4和5位的基团不同时是OMe，
(iii)如果第4位的基团是OH，则第3和5位的基团不是OMe，和
(iv)如果第4位的基团是甲基，则第3和5位的基团不是OH。
优选的化合物是其中X在第4位的化合物。最优选的化合物是当X在第4位并且Y和Z是H、OH、Me或OMe的化合物。
优选的具有非成键电子的基团是卤素、OH、OMe、NO2、CN、Ac、SO2NH2、CHO、CO2H和C1-C4烷基羧酸酯如CO2Et。
该化合物可以通过本领域公认的方法方便地制备和分离。它们与现有技术类似化合物的区别在于，它们具有出人意料高的清凉效果(最多10倍高于类似的已知化合物)及清凉效果的长效性，因此可增加它们在大量的各种产品中的吸引力。
例如，一小组专家被请求品尝清凉化合物的各种溶液并且指出哪些溶液具有与2ppm薄荷醇溶液类似或略高的清凉强度。在第二次实验中，请求相同的专家小组品尝选择浓度的溶液并且记录每隔固定时间的清凉强度，直至口中不再有清凉感觉为止。结果示于下表1。
表1关于清凉强度和持续时间的实验
  化学物质   浓度   持续时间
  1-薄荷醇   2.0ppm   35分钟
  N-乙基对-薄荷烷甲酰胺(WS-3)   1.5ppm   57分钟
  式I化合物，m＝0，Y＝Z＝H，X＝4-CN   0.5ppm   90分钟
  式I化合物，m＝0，Y＝Z＝H，X＝4-CH<sub>2</sub>CN   0.2ppm   93分钟
从表1可以看出，式I的化合物比参考清凉化合物薄荷醇强最多10倍和持续时间长最多3倍。式I的化合物还比WS-3强并且持续时间长，其中所述WS-3是现有技术中最好的清凉化合物。
本发明的化合物可以在施用于口腔或皮肤的产品中使用，以便得到清凉感。“施用”是指任何形式的接触，例如口服摄取，或当是烟草时是指吸入。当施用给皮肤时，可以是例如通过在乳霜或软膏中或者在可喷式组合物中包含所述化合物。因此，本发明还提供一种给口腔或皮肤提供清凉效果的方法，包括向其中施用含有如上所述化合物的产品。
下面将借助以下非限定性实施例的方式进一步描述本发明，这些实施例描述了优选的实施方案。
实施例1
制备N-(4-氰基甲基苯基)对-薄荷烷甲酰胺
向烧瓶中添加6.6g(50mmol)4-氨基苄基氰、4.04mL吡啶和100mL MtBE。经5分钟的时间向此混合物中滴加10g对-薄荷烷羧基氯。将反应混合物搅拌24h。向反应混合物中加入50mL水。将混合物分离。将有机层用50mL水和50mL盐水洗涤。将有机层经MgSO4干燥。将溶剂真空蒸发，得到粗产物，将其从己烷中重结晶，获得10.1g所需产品，其具有以下光谱学性能：
MS：299([M+1])，298([M+])，132，83
1H NMR(300MHz；CDCl3)δ：7.58(d，2H)，7.49(s，1H)，7.27(d，2H)，3.73(s，2H)，2.2(t，1H)，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 NMR(75MHz；CDCl3)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
实施例2
制备N-(4-氨磺酰苯基)对-薄荷烷甲酰胺：
按类似于实施例1所描述的方法制备，得到所需产品，其具有以下光谱学性能：
MS：339([M+1])，338([M+])，172，83
1H NMR(300MHz；DMSO)δ：10.21(s，1H)，7.76(d，1H)7.73(d，2H)，7.23(s，2H)，2.26-2.42(m，1H)，1.45-1.85(m，5H)，1.29-1.44(m，2H)，0.89(d，3H)，0.86(d，3H)，0.78(d，3H)
13C NMR(75MHz；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
实施例3
制备N-(4-氧基苯基)对-薄荷烷甲酰胺：
按类似于实施例1所描述的方法制备，得到所需产品，其具有以下光谱学性能：
MS：285([M+1])，284([M+])，139，83
1H NMR(300MHz；CDCl3)δ：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(m，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)
13C NMR(300MHz；CDCl3)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
实施例4
制备N-(4-乙酰基苯基)对-薄荷烷甲酰胺：
按类似于实施例1所描述的方法制备，得到所需产品，其具有以下光谱学性能：
MS：302([M+1])，301([M+])，135，83
1H NMR(300MHz；CDCl3)δ：7.93(d，2H)，7.66(d，2H)，7.63(s，1H)，2.57(s，3H)，2.09-2.31(m，1H)，1.84-1.98(m，1H)，1.68-1.85(m，5H)，1.56-1.68)(m，1H)，1.17-1.48(m，2H)，)，0.93(d，3H)，0.91(d，3H)，0.83(d，3H)
13C NMR(75MHz；CDCl3)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
实施例5
制备N-(4-羟基甲基苯基)对-薄荷烷甲酰胺：
按类似于实施例1所描述的方法制备，得到所需产品，其具有以下光谱学性能：
MS：290(M+1)，289(M+)，123，83
1H NMR(300MHz，DMSO)δ：9.9(s，1H)，7.54(d，2H)，7.21(d，2H)，4.2(s，2H)，2.36-2.1(m，1H)，1.8-1.59(m，6H)，1.57-1.44(m，1H)，1.21-0.9(m，4H)，0.87(dd，3H)，0.85(dd，3H)，0.79(d，2H)
13C NMR(75MHz；DMSO)δ：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
实施例6
制备N-(3-羟基-4-甲氧基苯基)对-薄荷烷甲酰胺：
按类似于实施例1所描述的方法制备，得到所需产品，其具有以下光谱学性能：
MS：306([M+1])，305([M+])，139，83
1H NMR(300MHz；CDCl3)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，2H)，1.53-1.94(m，5H)，1.17-1.48(m，2H)，0.97-1.17(m，2H)，0.92(dd，3H)，0.91(dd，3H)，0.82(d，3H)
13C NMR(75MHz；CDCl3)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
实施例7
在漱口剂中的应用
乙醇95％                                    177mL
山梨糖醇70％                                250g
实施例1化合物，以在乙醇中的1％溶液形式      50mL
薄荷油，无萜烯                              0.300g
水杨酸甲酯                                  0.640g
桉叶油素                                    0.922g
麝香草酚                                    0.639g
苯甲酸                                      1.500g
PluronicTMF127                              5.000g
糖精钠                                      0.600g
柠檬酸钠                                    0.300g
柠檬酸                                      0.100g
水                                          适量至1升
将各成分混合。将30mL所得的溶液放入口中，来回搅动、漱口并且吐出。口腔的每一区域及嘴唇都感到非常清凉。清凉感觉持续数小时。
实施例8
在牙膏中的应用
不透明牙凝胶                               97.000g
实施例2的化合物，以在PG中的2％溶液形式     2.500g
薄荷油，无萜烯                             0.500g
将各物质混合在牙凝胶中，并且让专家使用此牙膏刷牙。用水漱口并且将水吐出。专家们口腔中的每一区域都感觉到强烈的清凉感。清凉感持续数小时。

Claims (2)

1、下式I的化合物：
Figure C2004800332210002C1
其中m是O，Y和Z独立地选自H、OH和CH3，前提条件是：(a)当Y和Z是H时，X选自-CH2OH、-CH2CN、-CN、-SO2NH2和-COCH3；和(b)当Y是OH和Z是H时，X是-OCH3。
2、一种给口腔或皮肤提供清凉效果的方法，包括向其中施用含有权利要求1化合物的产品。
CN200480033221A 2003-11-21 2004-10-28 N-取代的对-薄荷烷甲酰胺 Expired - Lifetime CN100582089C (zh)

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BRPI0416770B1 (pt) 2014-05-13
DE602004026619D1 (en) 2010-05-27
EP1685093A1 (en) 2006-08-02
PL1685093T3 (pl) 2010-10-29
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US20060276667A1 (en) 2006-12-07
ATE464283T1 (de) 2010-04-15
ES2342466T7 (es) 2012-11-19
WO2005049553A1 (en) 2005-06-02
US7414152B2 (en) 2008-08-19
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