CN107375284B - 冷薄荷醇受体trpm8的低分子量调节剂的检测和用途 - Google Patents
冷薄荷醇受体trpm8的低分子量调节剂的检测和用途 Download PDFInfo
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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Abstract
本发明涉及冷薄荷醇受体TRPM8的低分子量调节剂的检测和用途。具体而言,本发明涉及冷薄荷醇受体TRPM8的新调节剂,使用这些调节剂调节TRPM8受体的方法;所述调节剂用于诱导冷感觉的用途;以及使用这些调节剂制备的物品和工具。
Description
本申请为2014年7月15日提交的中国发明专利申请201410336374.0 的分案申请,所述的中国发明专利申请201410336374.0是2009年8月26 日提交的、发明名称为“冷薄荷醇受体TRPM8的低分子量调节剂的检测 和用途”的PCT申请PCT/EP2009/061019的分案申请,所述PCT申请进 入中国国家阶段的日期为2011年2月28日,申请号为200980133390.7。
技术领域
本发明涉及冷薄荷醇受体TRPM8的新型调节剂,使用这些调节剂调 节TRPM8受体的方法;所述调节剂诱导冷感觉的用途;以及使用这些调 节剂制备的物品和组合物。
背景技术
冷薄荷醇受体TRPM8(也称为冷膜受体(CMR)1)属于“瞬时受体电位 离子通道”家族,在一类特定的神经元中表达,在细胞膜中形成空穴(在各 种情况下4个单元结合形成四聚体),其选择性的允许Ca2+离子通过。所述 蛋白具有6个跨膜结构域以及胞质C和N末端。低温(优选10-25℃)能刺 激该受体,产生信号转导,所述信号被神经系统理解为冷感觉。该受体在 2002年在多篇出版物中首次被描述为冷觉受体(Peier AM等,感觉冷刺激 和薄荷醇的TRP通道,2002Mar 8;108(5):705-15;McKemy DD等,冷受 体的鉴定揭示了TRP通道在热感觉中的普遍作用,Nature.2002Mar 7; 416(6876):52-8;Zuker CS.神经生物学:冷离子通道,Nature.2002 Mar 7;416(6876):27-8)。
致冷的化合物,例如薄荷醇,很长时间以来在调味剂和芳香剂工业中 具有重要作用,以产生新鲜和清洁感的结合。对于化合物薄荷醇来说,已 显示其作为受体TRPM8的天然调节剂起作用(McKemy D.D.,Molecular Pain 1,2005,16;McKemy D.D.,Nature 416,2002,52-58;Peier A.M.,Cell 108,2002,705-715;Dhaka A.,Annu.Rev.Neurosci.29,2006,135-161)。通 过应用薄荷醇,激活TRPM8,使得Ca2+流入冷敏神经元中。产生的电信 号最终被感知为冷感觉。薄荷醇浓度升高可导致刺激和麻醉效应。此外, 许多出版物描述了具有类似效应的薄荷醇衍生物(英国专利1971#1315761; Watson H.R.,J.Soc.Cosmet.Chem.29,1978,185-200;Furrer S.M.,Chem. Percept.1,2008,119-126)。还有结构上与薄荷醇不相关的个别化合物也产 生了显著的TRPM8调节效应,例如Icilin(Wei E.T.,J.Pharm.Pharmacol. 35,1983,110-112;WO 2004/026840)、WS-23或专利申请WO 2007/019719 中所列的化合物。
调节TRPM8受体和/或其昆虫中的类似物的物质的另一种效应是对昆 虫的驱除作用(WO 2002/015692;WO 2004/000023、US 2004/0028714),其 在抗肿瘤治疗(例如影响前列腺肿瘤)、炎性疼痛/痛觉过敏的治疗中也具有 活性,并且可用作TRPM8拮抗剂来有效治疗膀胱综合征或膀胱活动过度 (Beck B.Cell Calcium,41,2007,285-294;LevineJ.D.Biochim.Biophys. Acta,Mol.Basis Dis.1772,2007,989-1003;Mukerji G.,BMCUrology 6, 2006,6;US 2003/0207904;US 2005/6893626,Dissertation Behrendt H.J.2004,Bochum;Lashinger E.S.R.Am.J.Physiol.Renal Physiol. Am JPhysiol Renal Physiol.2008Jun 18.[在出版之前的电子版];PMID: 18562636)。
然而,迄今为止许多TRPM8调节剂在效应强度、效应持续时间、皮 肤/粘膜刺激、气味、味觉、溶解性和/或挥发性方面仍具有缺陷。
发明内容
因此,本发明的一个目的是鉴定调节TRPM8受体的新物质,其可用 作迄今已知的调节剂的备选物。这些化合物还应当尤其适用于化妆品(例如 护发、护肤、口腔护理)、营养品(饲料/食物)、纺织品、OTC产品(例如烧 伤软膏)、药物(例如肿瘤治疗、膀胱虚弱)、包装领域或作为杀虫剂或驱虫 剂。
发明详述:
1.通用术语定义:
在文献中,"TRPM8"有多个同义词:TRPP8、LTRPC6、CMR1、 MGC2849、瞬时受体电位阳离子通道亚家族M成员8。在本发明的背景 中,涵盖所有的名称。该受体的所有功能性修饰也包括在内,例如尤其是 剪接变体,亚型,例如TRPM8CRA_a、TRPM8CRA_b,和来自各种生物体例如人、小鼠、大鼠中的所有类似受体。不同受体的核苷酸和氨基酸 序列是本身已知的,在序列数据库中列出。因此,例如hTRPM8的序列信 息可以登录号NM_024080表示。
在本发明的内容中,“调节剂”是指能在体内和/或体外作为TRPM8 受体激动剂和/或拮抗剂起作用的化合物。
在本文中适当的调节剂可仅作为拮抗剂或激动剂起作用,或同时作为 拮抗剂和激动剂起作用,此时,产生激动效应或拮抗效应取决于选择的具 体调节剂的浓度。
在本文中,“激动剂”是指介导TRPM8受体活化,由此诱导Ca2+进 入冷敏神经元,从而介导冷感觉的化合物。相反,“拮抗剂”是指阻碍TRPM8 受体活化的化合物。
本发明的介导物可通过可逆或不可逆、特异性或非特异性结合TRPM8 受体分子发挥其作用。通常,与受体分子的结合通过离子和/或非离子的例 如疏水作用而非共价性的发生。在本文中,“特异性的”包括与一种或多 种不同的TRPM8受体分子(例如不同来源或不同亚型的TRPM8分子)排他 性的相互作用。相反,“非特异性的”是指所述调节剂与多种不同功能和/ 或序列的受体分子相互作用,但是可产生对TRPM8所希望的受体激动和/ 或拮抗调节(如上文所述)。
2.优选的实施方案
本发明首先涉及体外或体内调节冷薄荷醇受体TRMP8的方法,尤其 是人TRPM8受体,其中所述受体与至少一种选自多环有机化合物的化合 物接触,所述化合物在使用重组表达人TRPM8受体的细胞进行的细胞活 性测试中、特别是在标准条件下调节了这些细胞对Ca2+离子的通透性。
在该部分中,“标准条件”理解为表示使用经人TRPM8转化的HEK293 细胞进行的实验,该细胞加载了钙敏感染料(例如Fluo-4AM,即氟-4-乙酰 氧基甲基酯)后加入测试化合物,并检测颜色变化,实验过程在37℃进行, 如下文实施例3所述,或参见Behrendt等(2004),见上文)。
特别的,所述调节化合物包含至少2个4-至7-元环,其各自独立地为 碳环或杂环、单环或多环,其中在这些环中至少2个可任选稠合或螺连接。 合适的环连接的其他非限制性实例包括环碳原子和/或环杂原子间的化学 单键,通过2-6元碳桥连基团连接,其中各个碳原子可被诸如N、O或S 的杂原子替换。此外,所述环和桥连基可任选携带取代基,所述取代基选 自酮基、-OH、-SH、-CN、-NO2、-C1-6-烷基或C2-4-链烯基,其中在烷基 或链烯基中,一个或多个H原子可被诸如F、Cl、Br或I的卤素替换。
在本文中碳环包含4、5、6或7个碳原子;除环碳原子外,杂环包括 1-3个相同或不同的环杂原子,例如O、N和S原子。在本文中的环可以 各自独立地是饱和的、单或多不饱和的,例如芳环。
本发明使用的调节剂对于细胞Ca2+通透性具有激动或拮抗效应。具体 而言,所述调节剂是至少一种选自下表1中的式1-19的化合物。
表1:根据本发明的调节剂
其中化合物可以化学纯或富集形式存在,为单个立体异构体或立体异 构体混合物形式。此外,所述化合物可以是不带电的或其盐形式,例如酸 加成盐。官能团可任选被等价的化学基团替换;氟原子可被其他卤素原子, 例如Cl、Br或I替换;氧原子(例如醚基)可被相应的硫基团替换,反之亦 然;酮基团可被相应的亚硫酰基替换。上面具体描述的化合物是本身已知 的化学物质,可商购或通过常规有机合成方法获得。
因此,例如下列化合物是已知的:
化合物1,CAS号:99602-94-5(3R-顺式)
化合物2,CAS号:165753-08-2
化合物3,CAS号:338771-57-6
化合物4,CAS号:878942-21-3
化合物5,CAS号:748783-13-3
如果修饰形式或衍生物也表现出需要的生物学活性(受体TRPM8的调 节),那么它们也是功能类似物或功能等价化合物。
此外,本发明还包括使具体公开的物质与固相载体偶联的衍生物;本 领域技术人员已知可选择多种相应的接头/间隔基团。所述衍生化可在偶联 至固相前进行,或仅仅由偶联产生。
本发明还涉及TRPM8受体调节剂、尤其是激动剂在诱导人和/或动物 的冷感觉,尤其是局部的,即皮肤或口腔的冷感觉中的用途,其中所述调 节剂如上文所定义。当化合物在上述细胞活性测试中表现出对于hTRPM8 的激动效应时,称为“诱导冷感觉”。
本发明还涉及TRPM8受体调节剂作为药物组合物的活性成分的用 途,其中所述调节剂如上文所定义。
本发明还涉及TRPM8受体调节剂在前列腺癌治疗、膀胱虚弱治疗或 疼痛治疗中的用途,其中所述调节剂如上文所定义。
本发明还涉及TRPM8受体调节剂作为昆虫驱虫剂或杀虫剂的用途, 其中所述调节剂如上文所定义。
本发明还涉及TRPM8受体调节剂在诱导对以多种加工形式(例如纤 维、织物、模塑)的包装(例如由纸或塑料制成)的冷感觉中的用途,其中特 别是在接触包装材料时,冷感觉变得显著,其中所述调节剂如上文所定义。 在该部分内容中,所述物质可通过多种途径与包装材料相结合:例如通过 旋转涂层、凹印、微囊化形式、直接引入到包装材料中(例如挤压)、调节 剂的适当衍生物的共价偶联(通过适当的间隔物/接头基团来帮助分子与包装材料可逆或不可逆地结合)。本领域技术人员已知合适的方法。
本发明还涉及TRPM8受体调节剂在诱导纺织品的冷感觉中的用途, 其中所述调节剂如上文所定义。在该部分内容中,所述物质可通过多种途 径与纺织品相结合:例如通过旋转涂层、凹印、微囊化形式、直接引入到 纺织品材料中(例如挤压)、调节剂的适当衍生物的共价偶联(通过适当的间 隔物/接头基团来帮助分子与纺织品材料可逆或不可逆地结合)。本领域技 术人员已知合适的方法。
本发明还涉及根据上述定义的物质本身作为TRPM8受体调节剂的用 途,尤其是作为激动剂和/或拮抗剂。
本发明还涉及包含至少一种上述定义的化合物的组合物。特别的,所 述组合物选自:
a)药物组合物,例如抗肿瘤组合物,治疗膀胱疾病的组合物,止痛 剂;
b)食物,例如冰激凌、奶油冻、乳油、饮料、糕饼。
c)口腔护理组合物,例如牙膏、漱口水、口香糖、口气清新剂。
d)护肤或护发组合物,例如防晒霜、晒斑膏、洗剂、洗发水、硬膏、 漱口剂、洗液、剃毛霜、调节剂、洗面奶、肥皂、沐浴乳和沐浴泡沫、止 汗剂、除臭剂。
e)驱虫剂、杀虫剂。
除了各种具体组合物的常规成分外,所述组合物包含有效量的至少一 种本发明的调节剂。在该部分内容中,“有效”表示所述调节剂的浓度足 以带来需要的效应,例如药理学效果或感觉效应,例如在应用所述组合物 (例如应用至皮肤)后冷的嗅觉效应。
任选地,根据本发明的化合物可与其他已知的活性成分组合,尤其是 那些具有相同效应的。例如,可与已知的制冷化合物组合,例如薄荷醇、 薄荷酮、N-乙基-p-薄荷烷甲酰胺(WS-3)、N-2,3-三甲基-2-异丙基丁酰胺 (WS-23)、乳酸薄荷酯(ML)、薄荷酮甘油缩醛( MGA)、琥珀酸单薄荷酯戊二酸单薄荷酯、O-薄荷基甘油、 N,N-二甲基琥珀酸酰胺薄荷酯。
本发明还涉及纺织品,例如衬衫、长裤、袜子、毛巾,其采用至少一 种上述定义的化合物整理(finish)(尤其在表面上)。
本发明还涉及与至少一种上述定义的化合物结合的包装材料。
现参照下述非限制性的工作实施例来描述本发明。
附图说明
图1显示了来自根据序列数据库登录号NM_024080的hTRPM8受体 的(a)mRNA序列和(b)氨基酸序列。
图2显示了编码hTRPM8的质粒pInd_M8的载体图谱,其已用于转 染HEK293细胞。
具体实施方式
实验部分:
实施例1–人TRPM8的克隆
人TRPM8受体克隆的起点是LnCaP cDNA文库。其例如可从商业获 得(例如BioChain,Hayward,USA)或使用标准试剂盒从雄激素敏感的人前 列腺癌细胞系LnCaP(例如ATCC,CRL1740或ECACC,89110211)制备。
可使用标准方法PCR扩增和克隆编码TRPM8的序列(参见图1a;和 http://www.ncbi.nlm.nih.gov/entrez/viewer.fcgi?db=nuccore&id=10968969 4)。通过这种方法分离的人TRPM8基因被用于制备质粒pInd_M8,其构 建通过图2的质粒图谱进行说明。
或者,TRPM8基因也可通过合成制备。
实施例2-HEK293测试细胞的传代
制备稳定转染人TRPM8DNA(参见上述质粒pInd-M8)的HEK293细 胞系作为测试细胞系统。在本文中优选通过引入的质粒提供用四环素诱导 TRPM8表达的HEK293。
本领域技术人员已知生产适当的测试细胞系统的方法。例如,本发明 使用的细胞的制备详情参见Behrendt H.J.等,Br.J.Pharmacol.141,2004, 737-745或Behrendt的论文“Vergleichende funktionale Untersuchungen des Hitze-Capsaicin-Rezeptors(TRPV1)und des-Menthol-Rezeptors (TRPM8)in rekombinanten und nativenZellsystemen”.[热辣椒碱受体 (TRPV1)和冷薄荷醇受体(TRPM8)在重组和天然细胞系统中的功能比较研 究],参见:
http://www-brs.ub.ruhr-uni-bochum.de/netahtml/HSS/Diss/BehrendtHansJoerg/diss.pdf。
特别引用这些文献公开的内容。
实施例3-TRPM8调节剂的测定
采用与已描述在文献中的试验相当的试验,参见Behrendt H.J.等人,Br.J.Pharmacol.141,2004,737-745。受体的激动或拮抗通过Ca2+敏感性 染料(例如FURA,Fluo-4等)来量化。根据其自身特点,激动剂使Ca2+信号 增加,拮抗剂例如在薄荷醇存在下使Ca2+信号减少(各自通过染料Fluo-4 检测,其具有由Ca2+导致的不同的荧光性质)。
a)试验方法:
首先,在细胞培养瓶中以本身已知的方法制备转化的HEK细胞的新 鲜培养液。使用胰蛋白酶从细胞培养瓶上分离测试细胞HEK293-TRPM8, 按每100μl培养基40 000细胞/孔接种在96孔板中(Greiner#655948聚 -D-赖氨酸-涂覆)。为诱导受体TRPM8,向生长培养基中加入四环素 (DMEM/HG,10%无四环素FCS,4mM L-谷氨酰胺,15μg/ml灭菌素,100 μg/ml潮霉素B,1μg/ml四环素)。第二天,细胞加载Fluo-4AM染料,进 行试验。使用下列步骤:
-在每100μl培养基(DMEM/HG,10%无四环素FCS,4mM L-谷氨酰 胺,15μg/ml灭菌素,100μg/ml潮霉素B,1μg/ml四环素)中各自加入100 μl/孔的染料溶液Ca-4kit(RB 141,Molecular Devices)。
-在培养箱中孵育30分钟/37℃/5%CO2,30分钟/RT。
-制备供试物质(在200μl HBSS缓冲液中,不同浓度)和阳性对照(不 同浓度的薄荷醇、icilin和离子霉素,在200μl HBSS缓冲液中)和阴性对 照(仅200μl HBSS缓冲液)。
-以50μl/孔的量加入试验物质,在485nm激发、520nm发射测定荧 光的变化(例如测定仪器FLIPR,Molecular Devices或NovoStar,BMG), 评价不同物质/浓度的效果,确定EC50值。
试验物质以浓度0.1-200μM一式三份进行测定。通常将化合物保存 在DMSO溶液中,稀释至最大DMSO浓度2%进行测定。
b)试验结果
本发明调节剂测定的EC50值总结于下表2。
表2:试验物质对于人受体TRPM8的活性
该评价令人惊讶的发现,首次能够制备结构显著不同于已知的TRPM8 受体激动剂,例如(-)薄荷醇、icilin和其他Behrendt H.J.等在Br.J. Pharmacol.141,2004,737-745(参见表1)中描述的激动剂的TRPM8受体激 动剂,并且,在某些情况中其具有比(-)薄荷醇更好的活性,或与icilin效 果相当。
实施例4–漱口剂的制备
制备下列组成的漱口剂:
为制备漱口剂,以所述量混合上述成分。
本文特别参考所引用的文献资源的公开内容。
序列表
<110> 巴斯夫欧洲公司
<120> 冷薄荷醇受体TRPM8的低分子量调节剂的检测和用途
<130> M/49197-PCT
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<170> PatentIn 版本3.3
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aagaaaatcc tgcttgacaa aaaccgtcac ttaggaaaag atgtcctttc gggcagccag 60
gctcagcatg aggaacagaa ggaatgacac tctggacagc acccggaccc tgtactccag 120
cgcgtctcgg agcacagact tgtcttacag tgaaagcgac ttggtgaatt ttattcaagc 180
aaattttaag aaacgagaat gtgtcttctt taccaaagat tccaaggcca cggagaatgt 240
gtgcaagtgt ggctatgccc agagccagca catggaaggc acccagatca accaaagtga 300
gaaatggaac tacaagaaac acaccaagga atttcctacc gacgcctttg gggatattca 360
gtttgagaca ctggggaaga aagggaagta tatacgtctg tcctgcgaca cggacgcgga 420
aatcctttac gagctgctga cccagcactg gcacctgaaa acacccaacc tggtcatttc 480
tgtgaccggg ggcgccaaga acttcgccct gaagccgcgc atgcgcaaga tcttcagccg 540
gctcatctac atcgcgcagt ccaaaggtgc ttggattctc acgggaggca cccattatgg 600
cctgatgaag tacatcgggg aggtggtgag agataacacc atcagcagga gttcagagga 660
gaatattgtg gccattggca tagcagcttg gggcatggtc tccaaccggg acaccctcat 720
caggaattgc gatgctgagg gctatttttt agcccagtac cttatggatg acttcacaag 780
agatccactg tatatcctgg acaacaacca cacacatttg ctgctcgtgg acaatggctg 840
tcatggacat cccactgtcg aagcaaagct ccggaatcag ctagagaagt atatctctga 900
gcgcactatt caagattcca actatggtgg caagatcccc attgtgtgtt ttgcccaagg 960
aggtggaaaa gagactttga aagccatcaa tacctccatc aaaaataaaa ttccttgtgt 1020
ggtggtggaa ggctcgggcc agatcgctga tgtgatcgct agcctggtgg aggtggagga 1080
tgccctgaca tcttctgccg tcaaggagaa gctggtgcgc tttttacccc gcacggtgtc 1140
ccggctgcct gaggaggaga ctgagagttg gatcaaatgg ctcaaagaaa ttctcgaatg 1200
ttctcaccta ttaacagtta ttaaaatgga agaagctggg gatgaaattg tgagcaatgc 1260
catctcctac gctctataca aagccttcag caccagtgag caagacaagg ataactggaa 1320
tgggcagctg aagcttctgc tggagtggaa ccagctggac ttagccaatg atgagatttt 1380
caccaatgac cgccgatggg agtctgctga ccttcaagaa gtcatgttta cggctctcat 1440
aaaggacaga cccaagtttg tccgcctctt tctggagaat ggcttgaacc tacggaagtt 1500
tctcacccat gatgtcctca ctgaactctt ctccaaccac ttcagcacgc ttgtgtaccg 1560
gaatctgcag atcgccaaga attcctataa tgatgccctc ctcacgtttg tctggaaact 1620
ggttgcgaac ttccgaagag gcttccggaa ggaagacaga aatggccggg acgagatgga 1680
catagaactc cacgacgtgt ctcctattac tcggcacccc ctgcaagctc tcttcatctg 1740
ggccattctt cagaataaga aggaactctc caaagtcatt tgggagcaga ccaggggctg 1800
cactctggca gccctgggag ccagcaagct tctgaagact ctggccaaag tgaagaacga 1860
catcaatgct gctggggagt ccgaggagct ggctaatgag tacgagaccc gggctgttga 1920
gctgttcact gagtgttaca gcagcgatga agacttggca gaacagctgc tggtctattc 1980
ctgtgaagct tggggtggaa gcaactgtct ggagctggcg gtggaggcca cagaccagca 2040
tttcatcgcc cagcctgggg tccagaattt tctttctaag caatggtatg gagagatttc 2100
ccgagacacc aagaactgga agattatcct gtgtctgttt attataccct tggtgggctg 2160
tggctttgta tcatttagga agaaacctgt cgacaagcac aagaagctgc tttggtacta 2220
tgtggcgttc ttcacctccc ccttcgtggt cttctcctgg aatgtggtct tctacatcgc 2280
cttcctcctg ctgtttgcct acgtgctgct catggatttc cattcggtgc cacacccccc 2340
cgagctggtc ctgtactcgc tggtctttgt cctcttctgt gatgaagtga gacagtggta 2400
cgtaaatggg gtgaattatt ttactgacct gtggaatgtg atggacacgc tggggctttt 2460
ttacttcata gcaggaattg tatttcggct ccactcttct aataaaagct ctttgtattc 2520
tggacgagtc attttctgtc tggactacat tattttcact ctaagattga tccacatttt 2580
tactgtaagc agaaacttag gacccaagat tataatgctg cagaggatgc tgatcgatgt 2640
gttcttcttc ctgttcctct ttgcggtgtg gatggtggcc tttggcgtgg ccaggcaagg 2700
gatccttagg cagaatgagc agcgctggag gtggatattc cgttcggtca tctacgagcc 2760
ctacctggcc atgttcggcc aggtgcccag tgacgtggat ggtaccacgt atgactttgc 2820
ccactgcacc ttcactggga atgagtccaa gccactgtgt gtggagctgg atgagcacaa 2880
cctgccccgg ttccccgagt ggatcaccat ccccctggtg tgcatctaca tgttatccac 2940
caacatcctg ctggtcaacc tgctggtcgc catgtttggc tacacggtgg gcaccgtcca 3000
ggagaacaat gaccaggtct ggaagttcca gaggtacttc ctggtgcagg agtactgcag 3060
ccgcctcaat atccccttcc ccttcatcgt cttcgcttac ttctacatgg tggtgaagaa 3120
gtgcttcaag tgttgctgca aggagaaaaa catggagtct tctgtctgct gtttcaaaaa 3180
tgaagacaat gagactctgg catgggaggg tgtcatgaag gaaaactacc ttgtcaagat 3240
caacacaaaa gccaacgaca cctcagagga aatgaggcat cgatttagac aactggatac 3300
aaagcttaat gatctcaagg gtcttctgaa agagattgct aataaaatca aataaaactg 3360
tatgaactct aatggagaaa aatctaatta tagcaagatc atattaagga atgctgatga 3420
acaattttgc tatcgactac taaatgagag attttcagac ccctgggtac atggtggatg 3480
attttaaatc accctagtgt gctgagacct tgagaataaa gtgtgtgatt ggtttcatac 3540
ttgaagacgg atataaagga agaatatttc ctttatgtgt ttctccagaa tggtgcctgt 3600
ttctctctgt gtctcaatgc ctgggactgg aggttgatag tttaagtgtg ttcttaccgc 3660
ctcctttttc ctttaatctt atttttgatg aacacatata taggagaaca tctatcctat 3720
gaataagaac ctggtcatgc tttactcctg tattgttatt ttgttcattt ccaattgatt 3780
ctctactttt cccttttttg tattatgtga ctaattagtt ggcatattgt taaaagtctc 3840
tcaaattagg ccagattcta aaacatgctg cagcaagagg accccgctct cttcaggaaa 3900
agtgttttca tttctcagga tgcttcttac ctgtcagagg aggtgacaag gcagtctctt 3960
gctctcttgg actcaccagg ctcctattga aggaaccacc cccattccta aatatgtgaa 4020
aagtcgccca aaatgcaacc ttgaaaggca ctactgactt tgttcttatt ggatactcct 4080
cttattattt ttccattaaa aataatagct ggctattata gaaaatttag accatacaga 4140
gatgtagaaa gaacataaat tgtccccatt accttaaggt aatcactgct aacaatttct 4200
ggatggtttt tcaagtctat tttttttcta tgtatgtctc aattctcttt caaaatttta 4260
cagaatgtta tcatactaca tatatacttt ttatgtaagc tttttcactt agtattttat 4320
caaatatgtt tttattatat tcatagcctt cttaaacatt atatcaataa ttgcataata 4380
ggcaacctct agcgattacc ataattttgc tcattgaagg ctatctccag ttgatcattg 4440
ggatgagcat ctttgtgcat gaatcctatt gctgtatttg ggaaaatttt ccaaggttag 4500
attccaataa atatctattt attattaaat attaaaatat ctatttatta ttaaaaccat 4560
ttataaggct ttttcataaa tgtatagcaa ataggaatta ttaacttgag cataagatat 4620
gagatacatg aacctgaact attaaaataa aatattatat ttaaccctta gtttaagaag 4680
aagtcaatat gcttatttaa atattatgga tggtgggcag atcacttgag gtcaggagtt 4740
cgagaccagc ctggccaaca tggcaaaacc acatctctac taaaaataaa aaaattagct 4800
gggtgtggtg gtgcactcct gtaatcccag ctactcagaa ggctgaggta caagaattgc 4860
tggaacctgg gaggcggagg ttgcagtgaa ccaagattgc accactgcac tccagccggg 4920
gtgacagagt gagactccga ctgaaaataa ataaataaat aaataaataa ataaataaat 4980
attatggatg gtgaagggaa tggtatagaa ttggagagat tatcttactg aacacctgta 5040
gtcccagctt tctctggaag tggtcgtatt tgagcaggat gtgcacaagg caattgaaat 5100
gcccataatt agtttctcag ctttgaatac actataaact cactggctga aggaggaaat 5160
tttagaagga agctactaaa agatctaatt tgaaaaacta caaaagcatt aactaaaaaa 5220
gtttattttc cttttgtctg ggcagtagtg aaaataacta ctcacaacat tcactatgtt 5280
tgcaaggaat taacacaaat aaaagatgcc tttttactta aacaccaaga cagaaaactt 5340
gcccaatact gagaagcaac ttgcattaga gagggaactg ttaaatgttt tcaacccagt 5400
tcatctggtg gatgtttttg caggttactc tgagaatttt gcttatgaaa aatcattatt 5460
tttagtgtag ttcacaataa tgtattgaac atacttctaa tcaaaggtgc tatgtccttg 5520
tgtatggtac taaatgtgtc ctgtgtactt ttgcacaact gagaatcctg cagcttggtt 5580
taatgagtgt gttcatgaaa taaataatgg aggaattgtc a 5621
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Met Ser Phe Arg Ala Ala Arg Leu Ser Met Arg Asn Arg Arg Asn Asp
1 5 10 15
Thr Leu Asp Ser Thr Arg Thr Leu Tyr Ser Ser Ala Ser Arg Ser Thr
20 25 30
Asp Leu Ser Tyr Ser Glu Ser Asp Leu Val Asn Phe Ile Gln Ala Asn
35 40 45
Phe Lys Lys Arg Glu Cys Val Phe Phe Thr Lys Asp Ser Lys Ala Thr
50 55 60
Glu Asn Val Cys Lys Cys Gly Tyr Ala Gln Ser Gln His Met Glu Gly
65 70 75 80
Thr Gln Ile Asn Gln Ser Glu Lys Trp Asn Tyr Lys Lys His Thr Lys
85 90 95
Glu Phe Pro Thr Asp Ala Phe Gly Asp Ile Gln Phe Glu Thr Leu Gly
100 105 110
Lys Lys Gly Lys Tyr Ile Arg Leu Ser Cys Asp Thr Asp Ala Glu Ile
115 120 125
Leu Tyr Glu Leu Leu Thr Gln His Trp His Leu Lys Thr Pro Asn Leu
130 135 140
Val Ile Ser Val Thr Gly Gly Ala Lys Asn Phe Ala Leu Lys Pro Arg
145 150 155 160
Met Arg Lys Ile Phe Ser Arg Leu Ile Tyr Ile Ala Gln Ser Lys Gly
165 170 175
Ala Trp Ile Leu Thr Gly Gly Thr His Tyr Gly Leu Met Lys Tyr Ile
180 185 190
Gly Glu Val Val Arg Asp Asn Thr Ile Ser Arg Ser Ser Glu Glu Asn
195 200 205
Ile Val Ala Ile Gly Ile Ala Ala Trp Gly Met Val Ser Asn Arg Asp
210 215 220
Thr Leu Ile Arg Asn Cys Asp Ala Glu Gly Tyr Phe Leu Ala Gln Tyr
225 230 235 240
Leu Met Asp Asp Phe Thr Arg Asp Pro Leu Tyr Ile Leu Asp Asn Asn
245 250 255
His Thr His Leu Leu Leu Val Asp Asn Gly Cys His Gly His Pro Thr
260 265 270
Val Glu Ala Lys Leu Arg Asn Gln Leu Glu Lys Tyr Ile Ser Glu Arg
275 280 285
Thr Ile Gln Asp Ser Asn Tyr Gly Gly Lys Ile Pro Ile Val Cys Phe
290 295 300
Ala Gln Gly Gly Gly Lys Glu Thr Leu Lys Ala Ile Asn Thr Ser Ile
305 310 315 320
Lys Asn Lys Ile Pro Cys Val Val Val Glu Gly Ser Gly Gln Ile Ala
325 330 335
Asp Val Ile Ala Ser Leu Val Glu Val Glu Asp Ala Leu Thr Ser Ser
340 345 350
Ala Val Lys Glu Lys Leu Val Arg Phe Leu Pro Arg Thr Val Ser Arg
355 360 365
Leu Pro Glu Glu Glu Thr Glu Ser Trp Ile Lys Trp Leu Lys Glu Ile
370 375 380
Leu Glu Cys Ser His Leu Leu Thr Val Ile Lys Met Glu Glu Ala Gly
385 390 395 400
Asp Glu Ile Val Ser Asn Ala Ile Ser Tyr Ala Leu Tyr Lys Ala Phe
405 410 415
Ser Thr Ser Glu Gln Asp Lys Asp Asn Trp Asn Gly Gln Leu Lys Leu
420 425 430
Leu Leu Glu Trp Asn Gln Leu Asp Leu Ala Asn Asp Glu Ile Phe Thr
435 440 445
Asn Asp Arg Arg Trp Glu Ser Ala Asp Leu Gln Glu Val Met Phe Thr
450 455 460
Ala Leu Ile Lys Asp Arg Pro Lys Phe Val Arg Leu Phe Leu Glu Asn
465 470 475 480
Gly Leu Asn Leu Arg Lys Phe Leu Thr His Asp Val Leu Thr Glu Leu
485 490 495
Phe Ser Asn His Phe Ser Thr Leu Val Tyr Arg Asn Leu Gln Ile Ala
500 505 510
Lys Asn Ser Tyr Asn Asp Ala Leu Leu Thr Phe Val Trp Lys Leu Val
515 520 525
Ala Asn Phe Arg Arg Gly Phe Arg Lys Glu Asp Arg Asn Gly Arg Asp
530 535 540
Glu Met Asp Ile Glu Leu His Asp Val Ser Pro Ile Thr Arg His Pro
545 550 555 560
Leu Gln Ala Leu Phe Ile Trp Ala Ile Leu Gln Asn Lys Lys Glu Leu
565 570 575
Ser Lys Val Ile Trp Glu Gln Thr Arg Gly Cys Thr Leu Ala Ala Leu
580 585 590
Gly Ala Ser Lys Leu Leu Lys Thr Leu Ala Lys Val Lys Asn Asp Ile
595 600 605
Asn Ala Ala Gly Glu Ser Glu Glu Leu Ala Asn Glu Tyr Glu Thr Arg
610 615 620
Ala Val Glu Leu Phe Thr Glu Cys Tyr Ser Ser Asp Glu Asp Leu Ala
625 630 635 640
Glu Gln Leu Leu Val Tyr Ser Cys Glu Ala Trp Gly Gly Ser Asn Cys
645 650 655
Leu Glu Leu Ala Val Glu Ala Thr Asp Gln His Phe Ile Ala Gln Pro
660 665 670
Gly Val Gln Asn Phe Leu Ser Lys Gln Trp Tyr Gly Glu Ile Ser Arg
675 680 685
Asp Thr Lys Asn Trp Lys Ile Ile Leu Cys Leu Phe Ile Ile Pro Leu
690 695 700
Val Gly Cys Gly Phe Val Ser Phe Arg Lys Lys Pro Val Asp Lys His
705 710 715 720
Lys Lys Leu Leu Trp Tyr Tyr Val Ala Phe Phe Thr Ser Pro Phe Val
725 730 735
Val Phe Ser Trp Asn Val Val Phe Tyr Ile Ala Phe Leu Leu Leu Phe
740 745 750
Ala Tyr Val Leu Leu Met Asp Phe His Ser Val Pro His Pro Pro Glu
755 760 765
Leu Val Leu Tyr Ser Leu Val Phe Val Leu Phe Cys Asp Glu Val Arg
770 775 780
Gln Trp Tyr Val Asn Gly Val Asn Tyr Phe Thr Asp Leu Trp Asn Val
785 790 795 800
Met Asp Thr Leu Gly Leu Phe Tyr Phe Ile Ala Gly Ile Val Phe Arg
805 810 815
Leu His Ser Ser Asn Lys Ser Ser Leu Tyr Ser Gly Arg Val Ile Phe
820 825 830
Cys Leu Asp Tyr Ile Ile Phe Thr Leu Arg Leu Ile His Ile Phe Thr
835 840 845
Val Ser Arg Asn Leu Gly Pro Lys Ile Ile Met Leu Gln Arg Met Leu
850 855 860
Ile Asp Val Phe Phe Phe Leu Phe Leu Phe Ala Val Trp Met Val Ala
865 870 875 880
Phe Gly Val Ala Arg Gln Gly Ile Leu Arg Gln Asn Glu Gln Arg Trp
885 890 895
Arg Trp Ile Phe Arg Ser Val Ile Tyr Glu Pro Tyr Leu Ala Met Phe
900 905 910
Gly Gln Val Pro Ser Asp Val Asp Gly Thr Thr Tyr Asp Phe Ala His
915 920 925
Cys Thr Phe Thr Gly Asn Glu Ser Lys Pro Leu Cys Val Glu Leu Asp
930 935 940
Glu His Asn Leu Pro Arg Phe Pro Glu Trp Ile Thr Ile Pro Leu Val
945 950 955 960
Cys Ile Tyr Met Leu Ser Thr Asn Ile Leu Leu Val Asn Leu Leu Val
965 970 975
Ala Met Phe Gly Tyr Thr Val Gly Thr Val Gln Glu Asn Asn Asp Gln
980 985 990
Val Trp Lys Phe Gln Arg Tyr Phe Leu Val Gln Glu Tyr Cys Ser Arg
995 1000 1005
Leu Asn Ile Pro Phe Pro Phe Ile Val Phe Ala Tyr Phe Tyr Met
1010 1015 1020
Val Val Lys Lys Cys Phe Lys Cys Cys Cys Lys Glu Lys Asn Met
1025 1030 1035
Glu Ser Ser Val Cys Cys Phe Lys Asn Glu Asp Asn Glu Thr Leu
1040 1045 1050
Ala Trp Glu Gly Val Met Lys Glu Asn Tyr Leu Val Lys Ile Asn
1055 1060 1065
Thr Lys Ala Asn Asp Thr Ser Glu Glu Met Arg His Arg Phe Arg
1070 1075 1080
Gln Leu Asp Thr Lys Leu Asn Asp Leu Lys Gly Leu Leu Lys Glu
1085 1090 1095
Ile Ala Asn Lys Ile Lys
1100
Claims (16)
2.如权利要求1所述的方法,其中所述化合物对于细胞Ca2+离子通透性具有激动或拮抗效应。
3.TRPM8受体调节剂在制备诱导人和/或动物的冷感觉的组合物中的用途,其中所述调节剂为权利要求1中所述的化合物。
4.TRPM8受体调节剂在制备用于前列腺癌治疗、膀胱虚弱治疗或疼痛治疗的组合物中的用途,其中所述调节剂为权利要求1中所述的化合物。
5.TRPM8受体调节剂在制备作为昆虫驱虫剂或杀虫剂的组合物中的用途,其中所述调节剂为权利要求1中所述的化合物。
6.TRPM8受体调节剂在诱导包装的冷感觉中的用途,其中所述调节剂为权利要求1中所述的化合物。
7.TRPM8受体调节剂在诱导纺织品的冷感觉中的用途,其中所述调节剂为权利要求1中所述的化合物。
8.组合物,其包含至少一种如权利要求1中所述的化合物。
9.如权利要求8所述的组合物,选自:
a)药物组合物;
b)食物;
c)口腔护理组合物;
d)护肤或护发组合物;或
e)昆虫驱虫剂、杀虫剂。
10.如权利要求9所述的组合物,其为抗肿瘤组合物、膀胱疾病治疗组合物或止痛组合物。
11.如权利要求9所述的组合物,其为冰激凌、奶油冻、乳油、饮料或糕饼。
12.如权利要求9所述的组合物,其为牙膏、漱口水或口香糖。
13.如权利要求9所述的组合物,其为防晒霜、晒斑膏、洗剂、洗发水或硬膏。
14.纺织品,其采用至少一种如权利要求1中所述的化合物整理。
15.如权利要求14所述的纺织品,其为衬衫、长裤、袜子或毛巾。
16.与至少一种如权利要求1中所述的化合物结合的包装材料。
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