CN101065351A - 羧酰胺及其用途 - Google Patents

羧酰胺及其用途 Download PDF

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CN101065351A
CN101065351A CNA2005800401839A CN200580040183A CN101065351A CN 101065351 A CN101065351 A CN 101065351A CN A2005800401839 A CNA2005800401839 A CN A2005800401839A CN 200580040183 A CN200580040183 A CN 200580040183A CN 101065351 A CN101065351 A CN 101065351A
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isopropyl
valeramide
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C·伽罗宾
S·M·弗尔
J·P·斯拉克
P·V·克拉维克
L·科尔
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    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms 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 with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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    • C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms 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 with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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Abstract

本发明涉及通式(I)的清凉化合物，其中R1、R2、R3、X、Y、Z和m具有与说明书中给出的相同含义。本发明此外涉及其生产方法和包含它们的产品组合物。

Description

羧酰胺及其用途
本发明涉及清凉化合物，即，在皮肤上和在口腔粘膜上提供生理清凉效果的化合物。本发明还涉及其生产方法和包含其的产品组合物。
在风味和芳香工业中，继续需要具有独特的清凉性能的化合物，所述化合物可给使用者提供令人愉悦的清凉效果且适合于在各种产品、尤其是在可摄食和局部产品中使用。
英国专利GB1421744报道发现了具有生理清凉效果的简单的N-取代的酰胺。这些化学品是各种各样的，这是因为它们可完全用合成的方法制备。与在美国专利US4150052中所述的N-取代的对薄荷烷羧酰胺相反，它们的起始材料不依赖于天然来源。
现已发现，一类羧酰胺显示出强烈的清凉效果。因此，本发明一方面涉及通式I的化合物作为清凉剂的用途：
Figure A20058004018300041
其中X是(CH2)n-R，其中R是含至少一个自由电子对的基团，n为0或1；
Y和Z独立地选自H、OH、C1-C4烷基、C1-C4烷氧基；或者
Z是H、OH、C1-C4烷基、或C1-C4烷氧基；和
X与Y一起形成选自-O-CH2-O-、-N＝CH-O-、-N＝CH-NH-和-N＝CH-S-中的二价基团，所述基团和与它们相连的碳原子一起分别形成5元环(即1，3-二氧戊环(dioxalane))、1，3-唑环、1，3-二唑环或1，3-噻唑环；
m为0或1；
R1是H、C1-C4烷基，优选H或甲基；
R2和R3独立地代表C1-C4烷基，优选支化C3或C4烷基；和
R1+R2+R3的碳原子总数为至少6。
含至少一个自由电子对的基团优选选自卤素(例如Cl、F和Br)、氰基、羟基、甲氧基、NO2、乙酰基、SO2NH2、CHO、COOH、C1-C4烷基羧酸酯(例如COOCH3和COOC2H5)、C1-C4烷基羧酰胺(例如CONHCH3)、和含两个或更多个选自N、S和O的杂原子的5元杂环(例如二唑、三唑、四唑、唑和噻唑)。
尤其优选的是其中R1是氢以及R2和R3是异丙基的通式I的化合物或者R1是甲基以及R2和R3是异丙基的通式I的化合物。
通式I的优选化合物还包括其中X在2、4或6位(即在邻或对位)的那些。最优选的化合物是X在2、4或6位且Y和Z独立地代表氢、羟基、甲氧基或甲基的那些。
令人惊奇的是，本发明人发现，本发明的一些化合物显示出甚至比WS 23(N，2，3-三甲基-2-异丙基丁酰胺)更强烈的清凉效果，其中WS 23可被视为与本发明化合物化学不相关的化合物。根据我们的理解，WS23是在GB1421744中公开的唯一化合物，它已经商业化，因此选择它作为对比化合物。因此，最优选的是其中m为0、n为0和X选自氰基、甲氧基和甲基羧酸酯(COOCH3)的通式I的化合物。同样优选的是其中m和n为0且X和Y一起为O-CH2-O(即X和Y和与它们相连的碳原子一起形成二氧环戊烯(dioxol)环)的通式I的化合物。
在文献中从来没有描述过本发明的化合物，因此，本发明另一方面涉及通式I的化合物：
Figure A20058004018300051
其中R1、R2、R3、m、X、Y和Z具有与以上给出相同的含义。
尤其优选的式I化合物是N-(4-氰苯基)-2-异丙基异戊酰胺、N-(4-氰苯基)-2-甲基-2-异丙基异戊酰胺、N-(4-甲氧基苯基)-2-甲基-2-异丙基异戊酰胺、N-(4-氰甲基-苯基)-2-甲基-2-异丙基异戊酰胺、4-(2-异丙基-2，3-二甲基丁酰基氨基)苯甲酸异丙酯、N-(4-甲氧基苯基)-2-异丙基异戊酰胺、N-(2-氰苯基)-2-异丙基异戊酰胺、N-香草基-2-甲基-2-异丙基异戊酰胺和N-苯并[1，3]二氧环戊烯-5-基-2-甲基-2-异丙基异戊酰胺等。
落在本发明范围内的其它化合物的实例是N-香草基-2-异丙基异戊酰胺和N-苯并[1，3]二氧环戊烯-5-基-2-异丙基异戊酰胺。
本发明的化合物可在施加到口腔或者皮肤上以得到清凉感觉的产品中使用。“施加”是指任何接触形式，例如口服摄食，或者在烟草产品的情况下为吸入。在施加到皮肤上的情况下，可以是例如在霜或者药膏内或者在喷雾组合物内包括所述化合物。本发明因此还提供通过施加含有以上所述化合物的产品到口腔内或皮肤上，提供清凉效果的方法。
施加到口腔内的产品可包括摄入到口腔内并吞咽的食品和饮料，和由于其营养价值以外的原因摄食的产品，例如片剂、漱口剂、咽喉喷剂、洁牙剂和口香糖。施加到皮肤上的产品可选自可施加到人体皮肤上的香水、洗漱用品、洗剂、油和药膏，而不管是用于医药还是其它原因。因此，本发明在进一步的方面中涉及一种组合物，其包含一定量的通式I的化合物或其混合物，所述一定量足以刺激组合物与之接触的皮肤或者粘膜区域内的清凉受体，从而促进所需的清凉效果。一旦施加含有小于5000ppm，优选300-3000ppm的通式I的化合物的液体产品到粘膜上，例如口腔粘膜上，可获得清凉效果。
因此，本发明进一步涉及一种终产品，其选自局部用产品、口腔护理产品、鼻子护理产品、洗漱制品、可摄食产品和口香糖，和其包含产品基础成分和有效量的通式I的清凉化合物或其混合物。
本发明的化合物可单独使用或者与本领域已知的其它清凉化合物，例如薄荷醇、薄荷酮、异蒲勒醇、N-乙基对薄荷烷羧酰胺(WS-3)、N，2，3-三甲基-2-异丙基丁酰胺(WS-23)、乳酸薄荷酯、琥珀酸单薄荷酯(PhyscoolTM)、戊二酸单薄荷酯、邻薄荷基甘油(CoolActTM10)和2-仲丁基环己酮(FreskomentheTM)使用。
可在本领域公知的工艺条件下，通过氯化通式R1R2R3C-COOH的酸成相应的酰氯，使该酰氯进一步与通式II的胺反应，来制备通式I的化合物：
Figure A20058004018300071
其中R1、R2和R3、m、X、Y和Z具有与对于通式I化合物给出的相同含义。通式R1R2R3C-COOH的一些酸是可商购的。一般地，可例如通过在Tetrahedron，1980，36(6)，775-7或者Journal of ChemicalResearch，1978，2，46中所述的方法制备它们。
借助下述非限制性实施例进一步描述本发明。
实施例1：N-(4-氰苯基)-2-异丙基异戊酰胺
向烧瓶中添加5.9g(50mmol)4-氨基苄腈、4ml吡啶和100ml MtBE。在5分钟内向这一混合物中逐滴添加8g 2-异丙基异戊酰氯。搅拌反应混合物24小时。向这一反应混合物中添加50ml水。分离混合物。用50ml水和50ml盐水洗涤有机层。在硫酸镁上干燥有机层。真空蒸发溶剂，得到粗产物，从己烷中重结晶所述粗产物，得到10g所需产物。
MS：244([M+])，229，99，57
1H NMR(300MHz；CDCl3)δ：7.68(d，2H)，7.61(d，2H)，7.2(s，1H)，2.11(m，2H)，1.77(t，1H)，1.01(d，6H)，0.99(d，6H).
实施例2
按照与实施例1相同的工序合成表1所列的化合物。
表1
Figure A20058004018300081
Figure A20058004018300091
实施例3：清凉效果
根据以下所述的等强度方法，通过4-8个训练有素的小组成员确定化合物的清凉强度。
制备各种浓度化合物的水溶液，并进行测试。在2ppm下，比较每一溶液的清凉强度与参考化合物(即，N，2，3-三甲基-2-异丙基丁酰胺(WS 23))的水溶液的清凉强度。以下列表中给出了结果。
实施例  化合物名称 相对清凉强度
实施例1  N-(4-氰苯基)-2-异丙基异戊酰胺 1.3
实施例2A  N-(4-氰苯基)-2-甲基-2-异丙基异戊酰胺 1.5
实施例2B  N-(4-甲氧基苯基)-2-甲基-2-异丙基异戊酰胺 1.1
实施例2C  N-(4-氰甲基苯基)-2-甲基-2-异丙基异戊酰胺 0.2
实施例2D  4-(2-异丙基-2，3-二甲基丁酰基氨基)苯甲酸甲酯 1.4
实施例2E  N-(4-甲氧基苯基)-2-异丙基异戊酰胺 1.1
实施例2F  N-(2-氰苯基)-2-异丙基异戊酰胺 1.7
实施例2G  N-(2，4-二甲氧基苯基)-2-甲基-2-异丙基异戊酰胺 0.9
实施例2H  N-苯并[1，3]二氧环戊烯-5-基-2-甲基-2-异丙基异戊酰胺 0.9
实施例2I  N-香草基-2-甲基-2-异丙基异戊酰胺 0.8
实施例4：在漱口剂中的应用
醇95％ 177ml
山梨醇70％ 250g
 N-(4-氰甲基苯基)-2-异丙基异戊酰胺(在醇内1％的溶液) 50ml
无萜薄荷油 0.300g
水杨酸甲酯 0.640g
桉叶油素 0.922g
百里酚 0.639g
苯甲酸 1.500g
 PluronicF127 5.000g
糖精钠 0.600g
柠檬酸钠 0.300g
柠檬酸 0.100g
水 适量至1升
PluronicF127是双官能的嵌段共聚物表面活性剂(BASF的商品名)。
混合所有成分。将30ml所得溶液放入口腔内，搅动，含漱并吐出。在口腔以及嘴唇的每一区域内感到强烈的清凉感觉。
实施例5：在牙膏中的应用
不含香料或芳香剂的基本不透明的牙膏 97.000g
N-(4-氰苯基)-2-甲基-2-异丙基异戊酰胺(2％在PG*内的溶液) 2.500g
无萜薄荷油 0.500g
*PG＝丙二醇
在牙膏内混合所述化学品，并在牙刷上放置1g牙膏，刷洗受试验者的牙齿。用水漂洗口腔，并吐出水。在口腔的所有区域内，受试验者感到强烈的冰凉感觉。

Claims (9)

1.下述通式I的化合物：
Figure A2005800401830002C1
其中：
X是(CH2)n-R，其中R是含至少一个自由电子对的基团，和n为0或1；
Y和Z独立地选自H、OH、C1-C4烷基、C1-C4烷氧基，或者
Z是H、OH、C1-C4烷基或C1-C4烷氧基；和
X与Y一起形成选自-O-CH2-O-、-N＝CH-O-、-N＝CH-NH-和-N＝CH-S-的二价基团，所述基团和与它们相连的碳原子一起形成5元环；
m为0或1；
R1是H、C1-C4烷基；
R2和R3独立地代表C1-C4烷基；和
R1+R2+R3的碳原子之和为至少6。
2.权利要求1的化合物，其中R2和R3独立地代表支化C3或C4烷基。
3.权利要求1的化合物，其中R1是氢或甲基，和R2是异丙基，和R3是异丙基。
4.前述任何一项权利要求的化合物，其中R选自Cl、F、Br、氰基、羟基、甲氧基、NO2、乙酰基、SO2NH2、CHO、COOH、C1-C4烷基羧酸酯、C1-C4烷基羧酰胺，和含两个或更多个选自N、S和O的杂原子的5元杂环。
5.权利要求1的化合物，它选自下述通式I的化合物：N-(4-氰苯基)-2-异丙基异戊酰胺、N-(4-氰苯基)-2-甲基-2-异丙基异戊酰胺、N-(4-甲氧基苯基)-2-甲基-2-异丙基异戊酰胺、N-(4-氰甲基-苯基)-2-甲基-2-异丙基异戊酰胺、4-(2-异丙基-2，3-二甲基丁酰基氨基)苯甲酸异丙酯、N-(4-甲氧基苯基)-2-异丙基异戊酰胺、N-(2-氰苯基)-2-异丙基异戊酰胺、N-香草基-2-甲基-2-异丙基异戊酰胺、N-香草基-2-异丙基异戊酰胺、N-苯并[1，3]二氧环戊烯-5-基-2-甲基-2-异丙基异戊酰胺和N-苯并[1，3]二氧环戊烯-5-基-2-异丙基异戊酰胺。
6.前述任何一项权利要求中定义的通式I化合物作为清凉剂的用途。
7.一种给口腔或者皮肤提供清凉效果的方法，包括施加包含权利要求1-5任何一项中定义的通式I化合物的产品到所述口腔内或皮肤上。
8.一种给口腔或者皮肤提供清凉效果的产品，其包含选自权利要求1-5任何一项中定义的通式I化合物中的至少一种化合物。
9.一种产品，其选自局部用产品、口腔护理产品、鼻子护理产品、洗漱制品、可摄食产品和口香糖，其包括产品基础成分和有效量的权利要求1-5任何一项中定义的通式I化合物或其混合物。
CNA2005800401839A 2004-11-23 2005-11-21 羧酰胺及其用途 Pending CN101065351A (zh)

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