CN1649513A - 具有提高生物利用度/生物功效活性的枯茗植物及其提取物和提取物的精馏产物 - Google Patents
具有提高生物利用度/生物功效活性的枯茗植物及其提取物和提取物的精馏产物 Download PDFInfo
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- CN1649513A CN1649513A CNA038096617A CN03809661A CN1649513A CN 1649513 A CN1649513 A CN 1649513A CN A038096617 A CNA038096617 A CN A038096617A CN 03809661 A CN03809661 A CN 03809661A CN 1649513 A CN1649513 A CN 1649513A
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- cumin
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Abstract
本发明涉及一种生物提高剂/生物有效度促进剂的组合物,其包括:有效量的来自枯茗(Cuminum cyminum)的提取物和/或至少一种生物活性精馏产物;一种或多种添加剂,其选自药物、营养物、维生素、营养药物、草药/草药产品、微量营养物、抗氧化剂和药理学可接受的添加剂/赋形剂、和任选地,有效量的胡椒碱或有效量的胡椒或筚拔的提取物/精馏产物;本发明还涉及一种从枯茗植物制备这类水提取物、醇提取物和生物活性精馏产物的方法。
Description
发明领域
本发明涉及一种含有以枯茗(Cuminum cyminum)植物的提取物和/或枯茗(Cuminum cyminum)植物的生物活性精馏产物作为生物利用度提高剂的组合物。本发明还涉及一种以含有枯茗(Cuminum cyminum)的提取物和/或枯茗(Cuminum cyminum)的生物活性精馏产物及作为生物利用度提高剂的胡椒碱的组合物。本发明进一步涉及生物利用度和/或生物功效提高剂的应用及它们的制备方法,这种提高剂又被称为生物提高剂或BE,它们的制备是指从它们的天然原料中分离出来并最终得到它们的化学特性产品或指纹图谱形式产品。
发明背景
过去的研究已经采取了一些措施以最大的提高口服药物的生物利用度,比如(a)减少粒径(微粉化,纳米化,等),(b)多形态的或晶体尺寸和形态的选择,(c)通过化学修饰、配位和使用助溶剂/表面活性剂实现对微溶药物的增溶,(d)在作用位点定向给药,(e)通过薄膜包衣达到可控制给药或利用高分子聚合物实现药物的持续释放,(f)前药物方法,和(g)利用脂质体实现微胶囊化。
但是,基于对印度草药学的研究,为我们提供了一种新的提高药物生物利用度的方法,这种方法涉及的药物原本被位于查谟的申请机构Regional Research Laboratory(RRL)认为是缺乏生物有效性的药物。在印度草药处方中有一组被称为“Trikatu”的草药其被记录的频率非常高,几乎有大约70%的处方都将其作为重要组份使用,它包含三种辛辣物,即等比例的长胡椒、黑胡椒和干姜。来自胡椒的单一生物碱成分(胡椒碱)被发现具有提高生物利用度的作用。姜的作用是调节肠道功能以利于吸收。在抗结核药物开发中对胡椒碱的作用进行了深入的研究。一般认为,通过与胡椒碱的结合,利福平在保证抗结核药物疗效的情况下可以将其标准剂量(450mg)减少大约50%。基于这些发现,进而评价了其它几种植物的提高生物利用度/生物功效的活性。利用几种植物如干姜(Zingiber officinale)和葛蒌子(Carum carvi)的局部得到的极性提取物和非极性提取物可以显著地提高(25~300%)[见共同提交的专利申请]许多种类药物的生物利用度,这些药物为例如抗生素,抗真菌药,抗病毒药,抗癌药,心血管药,中枢神经系统疾病的药物,消炎药/治风湿药,抗结核药/抗麻风药,抗组胺剂/呼吸道疾病药物,皮质甾类,免疫抑制剂,治溃疡药,但是不仅限于以上药物。这些提取物无论是否含有胡椒碱都在其提高生物利用度/生物功效的作用中表现出明显的选择性。
枯茗(Cuminum cyminum)(属)(伞形植物)是一种矮小、纤细的一年生草药,主要分布于欧洲东南部,北非地中海沿岸,印度和中国。在印度几乎所有的邦都有它的种植。其中主要区域包括乌塔邦,旁遮普邦,拉贾斯坦邦,古吉拉特邦和马哈拉斯特拉邦。这种植物喜欢温和气候,从海平面到海拔10,000尺都可以生长。
它的种子通常被用作一种重要的调味品。在印度草药学中它被记载为katu,ushna和平复躁狂等作用。它是一种有效的胃刺激物,有助于治疗腹腔内的肿块,胃涨气,腹泻,口炎性腹泻并且是一种强力驱虫剂。它具有相应疗效并已经将其用作抗腹泻药,催奶剂,利尿剂同时还发现其有助于治疗声音嘶哑。它还被用作收敛剂,驱风剂。用它种子做成的糊外敷可以减轻由于肠胃内的寄生虫产生的疼痛和刺激。它的油可用于治疗湿疹。
已知这些植物除了被我们食用的部位以外的其他部位同样具有药效,根据我们过去将胡椒碱作为生物有效度提高剂得到的经验,我们如果要研究这种植物以测定它对生物有效度的提高效果,那么应该基于这种植物的那些与不同胡椒碱来源植物所共同具有的若干相似特性进行研究。
枯茗(Cuminum cyminum)的化学成分
对枯茗(Cuminum cyminum)的种子进行了分析并列出了分析结果,分析得到的种子成分是(百分比):水分11.9;蛋白18.7;醚提取物15.0;碳水化合物36.6;纤维12.0;矿物质5.8;钙1.08;磷0.49%;铁31.0mg/100g;以维生素A统计的胡罗卜素870I.U./100gm;维生素C3.0mg/100g(Hlth Bull.,No.23,1941,36)。
将种子进行蒸馏可以得到一种气味不好的,辛辣的并有一点苦的可挥发性油(2.0-4.0%)。这种油新制得的时候是无色或黄色的,保存一段时间后颜色变暗。印度油类分析参数为:d15°,0.8945;nD 15°1.490;[α]D 15°,+3.60;醛类16%;在20℃的温度下,这种油可以溶解在11倍体积的80%乙醇中。由Parry报道的参数范围是:sp.gr.0.900-0.930;n=1.494-1.507;[α]+3.0至+8.0°);醛类25-35%(Rao et al,J.Indian Inst.Sci.,1925,8A,182,Parry,E.J.“The Chemistry of Essential Oils and ArtificialPrfumes”[1921](Scott,Greenwood&Son Ltd.,London)Vol.1,P.311)。
这种可挥发性油的主要成分是枯茗醛(C10H12O,对异丙基苯甲醛,b.p.235°,),它占了油成分的20-40%。除了该醛,油中还含有对繖花烃,蒎烯,二戊烯,异丙基苯,枯茗醇,β-水芹烯和α-松油醇。提取完可挥发性油后剩下的剩余物含有17.2%的蛋白和30.0%的脂肪。剩余物可以用作牛饲料(Finnemore,H.“The Essential Oils”[1926](Ernest Benn.Ltd.,London)P.641)。种子中除了含有可挥发性油外还含有10%的混合油,其颜色为棕绿色并且具有很浓的芳香气味。
其他报道的化学成分为芹菜苷配基-7-葡萄糖苷,芹菜苷-7-二葡萄糖苷,芹菜苷-7,4’-二葡萄糖苷,芹菜苷-7-二半乳糖醛酸酐,芹菜苷-7-半乳糖苷葡萄糖苷,芹菜苷-7-半乳糖醛酸酐-4’-葡萄糖苷,芹菜苷-6,8-二-C-葡萄糖苷,藤黄菌素葡萄糖苷,藤黄菌素-7-二葡萄糖苷,藤黄菌素-7,3’-二葡萄糖苷,藤黄菌素-7,4’-二葡萄糖苷和藤黄菌素-7-半乳糖醛酸酐-4’-葡萄糖苷和柯伊利素糖苷(E1-Negoumy,S.I.et al.Grasas Aceites(Seville)1989,40(2)87-9)。
对于提高众多药物的生物有效度存在极大兴趣和医学需要,这些药物是指(a)生物可用性低,(b)服用期长,(c)有毒性和(d)价格昂贵的药物。因为该药物生物利用度的程度直接影响药物在血浆中的浓度从而关系到治疗的效果和口服给药后引起的毒性作用相关的剂量,所以最大化口服生物利用度在治疗方面是非常重要的。生物利用度低的药物都用作辅助治疗,因为剂量的主要部分无法达到血浆或发挥其药理作用,除非且直至给予将导致严重副作用的极大剂量。任何药物生物利用度的明显改善将导致降低该特定药物的剂量或使用频率。除此以外,物间可变性又反过来与生物利用度的程度有关。因此,口服药的低生物利用度导致了高的可变性和血浆中药物浓度和治疗效果的难控制性。物间可变性特别涉及那些安全范围比较窄的药物。
不完全的口服生物利用度是由不同原因造成的。这些原因包括溶解性差或者水中的溶解度低,对肠壁的透过性差,在胃液中或肠道液中降解和前于全身的肠道内或肝脏的代谢。为了解决这些问题以前公开的一些试验采取了加大用量的措施,导致了患者难以承受的毒副作用。
许多治疗措施在治疗过程中缺少必要的营养药物。本发明通过提高不同营养药物的生物利用度/生物功效而改善了营养状态,这些营养药物还包括矿物质和维生素。本发明的生物提高剂由于众多的原因使其能够在不影响其在血浆浓度的情况下提高药物的生物功效,部分原因在本发明中接下来的“生物利用度/生物提高活性”部分中进行了阐述,但并不仅限于这些原因。
生物利用度/生物功效的提高活性
在本发明中,术语生物利用度或生物提高(BE)活性是指“一种产品当其以比较低的用量与药物或营养素一起使用时,能够提高该药物的功效以降低该药物或营养素的消费量从而使这种药物功效提高。”
在本发明中,将植物各部位的水,水-醇,酮,醚,卤化溶剂提取物与不同治疗类型的药物和营养药物(必需的氨基酸,矿物质,抗氧化剂,维生素)和中草药单独或混合使用以评价其作用。提取物的用量从2.0mg到100mg其生物有效度提高(BE)活性是一致的,这与制剂中药物的用量无关。提取物的进一步精馏产物也与同类的药物一起使用以评价其效果。精馏产物的生物有效度提高活性随其在原提取物中所占的比例加大而提高。精馏产物的有效生物利用度提高活性的使用剂量为0.5到25.0mg。两种精馏产物被发现在上述范围内其活性是相同的。无论是将原提取物和其精馏产物混合使用还是单独使用,在它们与不同种类药物一起使用时都具有活性。精馏产物的用量从0.5mg到25.0mg其生物提高活性是一致的,这与制剂中药物的用量无关。精馏产物与原提取物相比具有更高的生物利用度提高活性。
研究发现将提取物或其精馏产物单独与胡椒碱(1-胡椒基哌啶)(1-piperoyl哌啶)一起使用,提取物或其精馏产物可以提高50%的活性。而当将原提取物和其精馏产物以不同比例混合再与胡椒碱混合使用时其活性提高60%。这些制剂中的胡椒碱用量为3-20mg。
提取物或其精馏产物无论是单独使用时还是与胡椒碱一起使用时都发现其生物利用度提高活性具有高度的选择性。这可以从这些提取物/精馏产物对生物利用度的提高程度很明显的看出。这种提高的程度从零到接近显著的程度(25%)进而到非常显著的程度(435%)。
这种选择性的原因可能是由于以下一种或多种原因造成的:
(a)提高胃肠传输试验(GIT)中的药物吸收,
(b)抑制或降低在肝脏中或肠中药物的生物转化率,
(c)以某种方式修饰免疫系统以尽量减少药物的总需要量,
(d)提高其穿透或进入病原体的能力,尽管这些病原体例如结核杆菌或其他微生物已经在巨噬细胞中变成了持久态。从而最终保证活性药物在另外不能够到达的范围内提高对微生物的杀死能力,
(e)抑制病原体或异常组织的抗药性,举例来说这种抗药性由于抗疟疾药,抗癌药和抗菌药的外排到自然界而经常出现,
(f)修饰宿主和病原菌的信号处理过程以确保提高药物对病原体的可及度提高,
(g)提高药物与病原体内例如受体,蛋白,DNA,RNA等目标位点的结合,从而加强和延长药效以提高抗生素的抗病原体活性,
(h)除了以上所述的可能的作用形式,生物提高剂还可能用于提高营养物的运输和药物通过血脑屏障的能力,这些作用对控制象大脑感染,癫痫症和其他中枢神经系统疾病(CNS)具有非常大的帮助。
本发明的主要作用是提高药物载体介导的进入组织和在组织中利用被动扩散和主动运输途径加强其运送的能力,从而将例如营养物等生理学物质运送到它们的目标位点,但也不排除其它作用。对于任何适用的作用机理,本发明产品的作用是一种协同和/或附加的作用,以致许多药物或营养药物当本发明所涉及的这种产品存在时由于以上所提到的一种或多种机理其生物实用性和生物有效性得到了提高。药物和营养药物的生物有效度和/或生物功效除了对人类十分重要外对动物的健康也有作用。因此本发明同样涉及在兽类医药领域的应用。
发明目的
本发明的主要目的是提供一种来自于枯茗(Cuminum cyminum)的活性提取物和生物活性精馏产物。
本发明的另一个目的是评估枯茗(Cuminum cyminum)的提取物或生物活性精馏产物与药物,营养物,营养药物,微量营养物和草药/产品一起使用时的生物增强作用和生物有效度。
本发明的另一个目的是提供一种生物提高剂组合物,其包含来自于枯茗(Cuminum cyminum)的活性成分与药物,营养物,营养药物,微量营养物和草药/产品一起使用。
本发明的另一个目的是提供一种生物提高剂组合物,其包含来自于枯茗(Cuminum cyminum)的提取物和/或生物活性精馏产物,胡椒碱和一种或多种以下这组物质:药物,营养物,营养药物,微量营养物和草药/产品。
另外,本发明的另一个目的是提供一种从枯茗(Cuminum cyminum)中分离生物活性精馏产物的方法,该精馏产物可以用作生物提高剂。
另外,本发明的另一个目的是一种用含水和/或醇性溶剂从枯茗(Cuminum cyminum)中分离生物活性精馏产物的方法。
发明概述
因此,本发明涉及来自枯茗(Cuminum cyminum)植物的包括其化学特性和指纹图谱特征的活性提取物/精馏产物的制备和将这种产品用于提高药物、天然产品和必需营养药物生物利用度和/或生物功效的方法。本发明涉及生物提高剂组和物的制备,该组合物包含枯茗(Cuminumcyminum)各部位的极性或非极性提取物和/或胡椒碱(EX:胡椒和荜拔),该组合可以显著(25%-435%)提高许多种类药物的生物利用度,比如抗生素,抗真菌药,抗病毒药,抗癌药,心血管药,中枢神经系统疾病的药物(CNS),消炎药/治风湿药,抗结核(TB)药/抗麻风药,抗组胺剂/呼吸道疾病药物,皮质甾类,免疫抑制剂,治溃疡药,但不限于这些药物。这些来自枯茗(Cuminum cyminum)的提取物/精馏产物无论是否与胡椒碱(Ex:胡椒和荜拔)一起使用都在其提高生物利用度/生物功效的作用中表现出高度的选择性。
附图简要说明
图1枯茗(Cuminum cyminum)的水提取物的HPLC色谱图
图2枯茗(Cuminum cyminum)的50%水和醇混合溶剂提取物的HPLC色谱图
图3枯茗(Cuminum cyminum)的精馏产物1的HPLC色谱图
图4枯茗(Cuminum cyminum)的精馏产物2的HPLC色谱图
图5枯茗(Cuminum cyminum)的精馏产物3的HPLC色谱图
图6枯茗(Cuminum cyminum)的精馏产物4的HPLC色谱图
图7枯茗(Cuminum cyminum)的精馏产物5的HPLC色谱图
发明的详细说明
因此,本发明提供一种生物提高剂/生物有效度促进剂的组合物,该组合物包含:
i.有效剂量的来自枯茗(Cuminum cyminum)的提取物和/或至少一种生物活性精馏产物;
ii.一种或多种添加剂,其选自药物,营养物,维生素,营养药物,草药/产品,微量营养物,抗氧化剂和药理学可接受的添加剂/赋形剂,和
iii.任选地,有效剂量的胡椒碱或胡椒或筚拔的提取物/精馏产物。
本发明的一个实施方式中枯茗(Cuminum cyminum)提取物的用量在约1.0到250mg的范围,优选2.0到100mg的范围。
本发明的另一个实施方式中在不考虑药物,营养物,维生素,营养药物,草药/产品,微量营养物和抗氧化剂等添加剂用量的情况下,枯茗(Cuminum cyminum)的精馏产物的用量在约0.5到75.0mg的范围,优选1.0到30mg范围。所用枯茗(Cuminum cyminum)的精馏产物选自被标记为1-5的精馏产物。
胡椒碱的用量在约3mg到50mg的范围,更确切地在3mg到20mg之间,其中胡椒碱分离自胡椒,筚拔或其树脂油。
本发明的另一个实施方式提供了一种组合物,其中药物成分选自以下这组药物:抗生素,抗真菌药,抗病毒药,抗癌药,心血管药,中枢神经系统疾病的药物(CNS),消炎药/治风湿药,抗结核(TB)药/抗麻风药,抗组胺剂/呼吸道疾病药物,皮质甾类,免疫抑制剂,治溃疡药和草药。
本发明的另一个实施方式中所用抗生素选自喹诺酮,大环内酯物,头孢菌素,青霉素和氨基糖苷这组物质;其中喹诺酮选自环丙沙星,培氟沙星,氧氟沙星和诺氟沙星这组物质;其中大环内酯物选自红霉素,罗红霉素和阿奇霉素这组物质;其中头孢霉素选自头孢氨苄,头孢曲松(cefatrioxone),头孢克肟,头孢匹罗,头孢地尼和头孢羟氨苄这组物质;其中青霉素选自阿莫西林和氯唑西林这组物质;和其中氨基糖苷选自阿米卡星和卡那霉素这组物质。
本发明的另一个实施方式中抗真菌药选自氟康唑,两性霉素B,灰黄霉素和酮康唑这组物质;抗病毒药选自阿昔洛韦和叠氮胸苷这组物质。
本发明的另一个实施方式中抗癌药物选自甲氨蝶呤,5-氟尿嘧啶,阿霉素,紫杉醇和顺铂这组物质。
本发明的另一个实施方式中心血管药物选自氨氯地平,赖诺普利,普萘洛尔和阿替洛尔这组物质;中枢神经系统药物选自阿谱唑仑和氟哌啶醇这组物质。
本发明的另一个实施方式中消炎药/治风湿药选自双氯芬酸钠,吡罗昔康,尼美舒利和罗非克西这组物质;抗结核(TB)药/抗麻风药选自利福平,乙硫异烟胺,异烟肼,环丝氨酸,吡嗪酰胺,乙胺丁醇和氨苯砜这组物质。
抗组胺剂/呼吸道疾病药物选自沙丁胺醇,茶碱,溴己新和氯雷替定这组物质;皮质甾类选自强的松龙,地塞米松和倍他米松这组物质;免疫抑制剂选自环孢霉素A,他克莫司和霉酚酸酯这组物质;治溃疡化合物选自雷尼替丁,西咪替丁和奥美拉唑这组物质。
本发明的另一个实施方式中草药产品和草药选自海胆(Echinacea),雪兰莪草(Tinospora cordifolia),胡雪莲(Picrorrhiza kurroa),木橘(Aegles marmelos),穿心莲(Andrographis paniculata),白花酸藤果(Emblica ribes),总序天冬(Asparagus racemosus),绒毛诃子(Terminalia chebula),催眠睡茄(Withania somnifera),积雪草(Centellaasiatica)和/或其混合物。
本发明的另一个实施方式涉及的组合物中营养物选自糖,碳水化合物,脂肪和蛋白这组物质;维生素选自维生素A,维生素E,维生素B1,维生素B6,维生素B12,维生素C和叶酸;抗氧化剂选自β-胡萝卜素,水飞蓟素,硒,番茄红素和Ellagiogallotannins。
本发明的另一个实施方式天然草药产品选自姜黄素,乳香酸和芸香苷这组物质;必需微量营养物选自蛋氨酸,赖氨酸,亮氨酸,缬氨酸,异亮氨酸,锌,钙,葡萄糖,钾,铜和铁。
本发明的另一个实施方式涉及的枯茗(Cuminum cyminum)植物提取物或枯茗(Cuminum cyminum)植物提取物的生物活性精馏产物提取自枯茗(Cuminum cyminum)植物的任意部位。
本发明的另一个实施方式中以上所提到的组合物是通过口服,肠道外,鼻腔,吸入包括雾化,直肠,阴道,透皮作用和其他任意适合途径给药的。
本发明的另一个实施方式中当将来自于枯茗(Cuminum cyminum)的植物提取物或生物活性精馏产物单独使用或与胡椒碱一起用于提高药物,营养药物,和草药/制剂的生物利用度/生物功效的时,发现其生物提高作用具有选择性。
本发明的另一个实施方式提供了包含枯茗(Cuminum cyminum)植物的提取物或精馏产物的组合物,他们提供生物利用度/生物提高活性为25-335%。
本发明的另一个实施方式中将一种来自枯茗(Cuminum cyminum)成分和胡椒碱的组合物显示生物提高/生物利用度活性从接近显著的即约25%到非常显著的即约435%。
本发明的另一个实施方式中所述含枯茗(Cuminum cyminum)和胡椒碱提供对生物利用度/生物提高活性比单独使用来自枯茗(Cuminumcyminum)生物提高活性可以提高10%到85%。
本发明的一个实施方式中涉及含枯茗(Cuminum cyminum)的提取物的组合物用量为10-30mg/kg/体重,含枯茗(Cuminum cyminum)的生物活性精馏产物的组合物为2-20mg/kg/体重。
本发明的另一个实施方式涉及将含枯茗(Cuminum cyminum)的提取物或生物活性精馏产物和胡椒碱组合物,其中胡椒碱的用量为0-12mg/kg/体重。
本发明的另一个实施方式涉及一种从枯茗(Cuminum cyminum)植物制备其水提取物,含水醇提取物和生物活性精馏产物的方法,所述方法包括如下步骤:
a)粉碎植物,将其用水或50%的醇水溶液在95-100℃进行萃取,分别得到水提取物或醇水提取物,
b)将步骤(a)得到的一部分水提取物用正丁醇(n-BuOH)进行萃取,并分离正丁醇层和水层,
c)将步骤(b)得到的正丁醇层进行蒸发和冷冻干燥处理得到精馏产物1,
d)将步骤(b)得到的水层进行蒸发和冷冻干燥处理得到精馏产物2,
e)将步骤(a)得到的另一部分水层用醇进行回流,汇聚醇提取物并分离剩余的物质备用,
f)将步骤(e)汇聚得到的醇提取物进行蒸发,得到精馏产物3,
g)将步骤(e)的剩余物用50%的醇水溶剂进行提取,得到50%的醇水可溶部分,剩余物作为精馏产物5,
h)将步骤(g)得到的醇水可溶部分进行蒸发,得到精馏产物4。
本发明的另一个实施方式提供了得到的来自植物枯茗(Cuminumcyminum)的提取物和生物活性精馏产物的HPLC色谱。
本发明的另一个实施方式中HPLC色谱是利用RP18柱,体积比为83∶17的水∶乙腈溶液,溶液中含有2%的醋酸;流速为1ml/min,使用紫外(UV)检测器得到的。
本发明的另一个实施方式中从植物枯茗(Cuminum cyminum)得到的水提取物具有的HPLC色谱主吸收峰的保留时间为:2.16,2.44,4.40,6.56,8.27,14.34和15.24。
本发明的另一个实施方式中从植物枯茗(Cuminum cyminum)得到的50%醇水提取物具有的HPLC色谱主吸收峰的保留时间为:4.38,6.53,8.25,10.43,14.29和15.17。
本发明的另一个实施方式中从植物枯茗(Cuminum cyminum)得到的精馏产物1具有的HPLC色谱主吸收峰的保留时间为:2.52,3.59,6.25,11.01和14.46。
本发明的另一个实施方式中从植物枯茗(Cuminum cyminum)得到的精馏产物2具有的HPLC色谱主吸收峰的保留时间为:2.43,4.38和6.52。
本发明的另一个实施方式中从植物枯茗(Cuminum cyminum)得到的精馏产物3具有的HPLC色谱主吸收峰的保留时间为:3.11,7.75,10.37,13.80和17.95。本发明的另一个实施方式中从植物枯茗(Cuminumcyminum)得到的精馏产物4具有的HPLC色谱主吸收峰的保留时间为:2.31,3.14,5.25,7.71,9.63,13.82和17.92。
本发明的另一个实施方式中从植物枯茗(Cuminum cyminum)得到的精馏产物5具有的HPLC色谱主吸收峰的保留时间为:2.25,3.01,5.21和7.69。
实施例
接下来的实施例是为了对本发明的部分优选实施方式进行说明,但是这些说明并不对本发明的保护范围进行任何限定。本领域普通技术人员可以对发明进行进一步的开发,这些内容也包含在本发明保护范围之内。
实施例1
利用IP 1726890中所描述的新方法制备无色的,没有辛辣气味的胡椒碱,并利用以下方法对其进行进一步的修饰:将可以进行商购的胡椒或筚拔或它们的树脂油作为原料;将20kg长胡椒树脂油用例如CHCl3,CH2Cl2,C2H4Cl2等卤代溶剂(25升)提取6小时或将20kg黑胡椒粉用甲苯进行索氏萃取8小时;将提取物进行减压浓缩干燥并在78℃溶解于乙醇中;将乙醇溶液用装在玻璃柱中的天然Al2O3进行吸收;利用CHCl3∶EtOH(9∶1)的混合溶剂进行洗脱,将洗脱液进行浓缩干燥并溶解于最小量的乙醇中;将溶液用活性炭进行处理,并通过硅藻土床进行过滤;将过滤产物进行浓缩到饱和点,冷却,得到无色的晶体沉淀物;将沉淀物利用吸气过滤和干燥进行分离。
实施例2
有关优选材料的说明如下:
胡椒碱
颜色:无色的,单斜(晶系)的棱状结晶体;
熔点:129℃-130℃
分析:最少99.1%(液相色谱/质谱(LC/MS))
得自枯茗(Cuminum cyminum)的生物提高剂:
该申请说明书附图提供了产品的制备和全指纹图谱(HPLC)。
实施例3
下面列出了典型实验的剂量,模式/实验设计和评价方法:
一个典型的实验设计方案和不同生物提高剂的用量:
1.将来自枯茗(Cuminum cyminum)的水提取物,50%的醇提取物或精馏产物1-5作为生物提高剂(BEs)。
2.将具有本发明实施例2中所述特性的胡椒碱分子作为生物提高剂(BE),该成分取自胡椒种类的植物。
3.在不抵抗枯茗(Cuminum cyminum)的提取物或其精馏产物剂量不同的情况下,由于所使用的精馏产物与其在提取物中的浓度是成比例的,所以与它们联合的药物生物利用度所致的提高作用是几乎相同的。
4.甚至当将生物提高剂(BEs)相互联合使用时,其使用剂量可以保持不变或减少50%的剂量。
实施例4:剂量:
(i)得自枯茗(Cuminum cyminum)的生物提高剂(BE)
提取物: 16mg/kg体重(大鼠)
精馏产物1:02-5mg/kg体重(大鼠)
精馏产物2:13-mg/kg体重(大鼠)
精馏产物3:8mg/kg体重(大鼠)
精馏产物4:5mg/kg体重(大鼠)
精馏产物5:2.5-5mg/kg体重(大鼠)
(ii)胡椒碱:8mg/kg体重(大鼠)
大鼠(被禁食)实验中的一个实施例:
药物:利福平,40mg/kg
生物提高剂(枯茗(Cuminum cyminum)):采用该实施例中上面所述的精馏产物5的剂量
生物提高剂(枯茗(Cuminum cyminum))+胡椒碱:采用该实施例中上面所述的精馏产物5的剂量
试验步骤:按照下面的设计方案对大鼠进行单独给药或与BE联合给药:
第1组:对照
第2组:单独使用利福平
第3组:单独使用生物提高剂
第4组:利福平+生物提高剂(枯茗(Cuminum cyminum))
第5组:利福平+生物提高剂(枯茗(Cuminum cyminum)+胡椒碱)
按照预定的时间间隔(0-24小时)从对照/实验动物身上取血(总共14次)。利用二氯甲烷作为提取剂从血(血浆)中提取利福平。样品中的利福平浓度利用HPLC(型号:Shimadizu1080 BP)进行检测;PDA检测器;流动相:磷酸盐缓冲液∶丙酮(40∶60);流速:1.0ml/min;RP18柱。
进行对照组和单独使用生物提高剂组的实验从而研究血浆成分和所用的生物提高剂成分的干扰情况。
实施例5
上述方法也可以用于评价其它药物,微量营养物,营养药物,营养物和其它草药产品的提高活性,其提高效果见下列各表。下面列举的标题分别为药物,营养药物,草药制剂的表格仅仅是本发明发明目的的一部分实施例:
A.药物
种类 | 药物 | |
I | 抗生素 | 氟代喹诺酮类环丙沙星,诺氟沙星,培氟沙星,和氧氟沙星大环内酯类红霉素,罗红霉素,和阿奇霉素头孢菌素类头孢氨苄,头孢羟氨苄,头孢曲松(cefatrioxone),头孢克肟,头孢匹罗,和头孢地尼青霉素类阿莫西林,氯唑西林氨基糖苷类阿米卡星,卡那霉素 |
II | 抗真菌药 | 氟康唑,两性霉素B,灰黄霉素,酮康唑 |
III | 抗病毒药 | 阿昔洛韦,叠氮胸苷 |
IV | 抗癌药 | 甲氨蝶呤,5-氟尿嘧啶,阿霉素,顺铂 |
V | 心血管药 | 氨氯地平,赖诺普利和阿替洛尔 |
VI | 中枢神经系统疾病的药物 | 阿谱唑仑和氟哌啶醇 |
VII | 消炎药/治风湿药(NSAID) | 双氯芬酸钠,吡罗昔康,尼美舒利和罗非克西 |
VIII | 抗结核(TB)药/抗麻风药 | 利福平,乙硫异烟胺,异烟肼,环丝氨酸,吡嗪酰胺,乙胺丁醇,氨苯砜 |
IX | 抗组胺剂/呼吸道疾病药物 | 沙丁胺醇,茶碱,溴己新,氯雷替定 |
X | 皮质甾类 | 强的松龙,地塞米松,倍他米松 |
XI | 免疫抑制剂 | 环孢霉素A,他克莫司,霉酚酸酯 |
XII | 治溃疡药 | 雷尼替丁,西咪替丁,奥美拉唑 |
A.药物种类:
I.抗生素:
(a)氟代喹诺酮
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
环丙沙星 | 52 | 40 | 47 |
培氟沙星 | 47 | 51 | 57 |
氧氟沙星 | 61 | 40 | 73 |
诺氟沙星 | 可以忽略的 | 可以忽略的 | 可以忽略的 |
(b)大环内酯类
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
红霉素 | 75 | 105 | 95 |
罗红霉素 | 67 | 95 | 103 |
阿奇霉素 | 83 | 91 | 97 |
(c)头孢菌素
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
头孢氨苄 | 60 | 70 | 75 |
头孢羟氨苄 | 90 | 86 | 79 |
头孢曲松(cefatrioxone) | 0 | 0 | 0 |
头孢克肟 | 0 | 0 | 0 |
(d)青霉素
(e)
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
阿莫西林 | 75 | 111 | 98 |
氯唑西林 | 94 | 68 | 95 |
(f)氨基糖苷
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
阿米卡星 | 0 | 可以忽略的 | 0 |
卡那霉素 | 95 | 65 | 110 |
II.抗真菌药:
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
氟康唑 | 170 | 110 | 126 |
两性霉素B | 0 | 可以忽略的 | 可以忽略的 |
灰黄霉素 | 136 | 138 | 156 |
III.抗病毒药:
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
阿昔洛韦 | 110 | 77 | 98 |
叠氮胸苷 | 330 | 270 | 415 |
IV.中枢神经系统疾病的药物:
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
阿谱唑仑 | 60 | 98 | 104 |
氟哌啶醇 | 0 | 0 | 0 |
V.抗癌药:
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
甲氨蝶呤 | 125 | 70 | 30 |
5-氟尿嘧啶 | 335 | 290 | 435 |
阿霉素 | 85 | 42 | 103 |
顺铂 | 70 | 可以忽略的 | 79 |
VI.心血管药:
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
氨氯地平 | 55 | 29 | 103 |
赖诺普利 | 83 | 110 | 98 |
阿替洛尔 | 0 | 可以忽略的 | 可以忽略的 |
普萘洛尔 | 135 | 170 | 210 |
VII.消炎药/治风湿药:
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
双氯芬酸钠 | 65 | 79 | 108 |
吡罗昔康 | 70 | 92 | 107 |
尼美舒利 | 168 | 110 | 150 |
罗非克西 | 可以忽略的 | 可以忽略的 | 可以忽略的 |
VIII.抗结核(TB)药/抗麻风药:
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
利福平 | 250 | 115 | 336 |
异烟肼 | 0 | 22 | 可以忽略的 |
吡嗪酰胺 | 0 | 17 | 0 |
乙胺丁醇 | 0 | 0 | 0 |
氨苯砜 | 60 | 40 | 75 |
乙硫异烟胺 | 78 | 48 | 65 |
环丝氨酸 | 89 | 50 | 90 |
IX.抗组胺剂/呼吸道疾病药物:
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
沙丁胺醇 | 110 | 55 | 85 |
茶碱 | 87 | 70 | 75 |
溴己新 | 50 | 48 | 90 |
氯雷替定 | 0 | 0 | 0 |
X.皮质甾类:
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
强的松龙 | 0 | 0 | 0 |
地塞米松 | 85 | 56 | 105 |
倍他米松 | 95 | 65 | 82 |
XI.免疫抑制剂:
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
环孢霉素A | 156 | 223 | 275 |
他克莫司 | 75 | 105 | 117 |
霉酚酸酯 | 0 | 0 | 0 |
XII.治溃疡药:
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
雷尼替丁 | 117 | 0 | 89 |
西咪替丁 | 123 | 0 | 105 |
奥美拉唑 | 0 | 0 | 0 |
B.营养药物种类
生物利用度提高% | |||||
种类 | 剂量(mg/kg) | 得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
I | 维生素维生素A维生素E维生素B1维生素B6维生素B12维生素C叶酸 | 140100.50.1μg5050μg | 260370000 | 140160000 | 180330000 |
II | 抗氧化剂β-胡萝卜素水飞蓟素硒 | 1552 | 45320 | 34130 | 53410 |
III | 天然草药产品姜黄素乳香酸芸香苷 | 505040 | 3900 | 33026 | 29022 |
IV | 必须营养元素蛋氨酸赖氨酸亮氨酸缬氨酸异亮氨酸锌*钙*葡萄糖钾*铜*铁* | 20405025250.1305025300.5 | 2735312040可以忽略的17160023 | 23312526180可以忽略的29000 | 30293224220可以忽略的110029 |
*剂量相当于基本浓度,利用原子吸收光谱测定得到的
C.中药组合物(原文中缺少标号C.)
药物 | 生物利用度提高% | ||
得自枯茗的生物提高剂 | 将胡椒碱作为生物提高剂 | 胡椒碱+活性分子 | |
海胆 | 72 | 110 | 90 |
雪兰莪草 | 98 | 107 | 152 |
胡雪莲 | 78 | 95 | 115 |
木橘 | 0 | 0 | 0 |
穿心莲 | 72 | 0 | 68 |
白花酸藤果 | 72 | 0 | 60 |
总序天冬 | 35 | 47 | 72 |
绒毛诃子 | 0 | 0 | 0 |
催眠睡茄 | 55 | 52 | 65 |
积雪草 | 0 | 0 | 0 |
枯茗(Cuminum cyminum)植物提取物的制备流程图
枯茗(Cuminum cyminum)植物水提取物的精馏产物流程图
具有生物活性的水提取物的精馏产物是利用正丁醇和水按照典型实施例的方案进行分离得到的(流程图1),并对另一部分用95%的乙醇和50%的醇水溶液提取物进行研制(流程图2)。
流程图1
剩余物 :13.0grams 剩余物 :82.0gm
基于提取物%:13.68 基于提取物%:86.31
基于植物% :2.3 基于植物% :14.6
(精馏产物1) (精馏产物2)
利用50%醇水溶液得到的植物原料的原始提取物也可以利用上述的相同流程进行精馏。
流程图2
利用50%醇水溶液得到的植物原料的原始提取物也可以利用上述相同的流程进行精馏。
Claims (42)
1.一种生物提高剂/生物利用度促进剂的组合物,其组分包括:
i.有效量的来自枯茗的提取物和/或至少一种生物活性精馏产物;
ii.一种或多种添加剂,其选自药物、营养物、维生素、营养药物、草药/产品、微量营养物、抗氧化剂和药学可接受的添加剂/赋形剂,和
iii.任选地,有效量的胡椒碱或胡椒或筚拔的提取物/精馏产物。
2.权利要求1所述的组合物,其中所用的枯茗提取物的用量为约1.0mg到250mg范围。
3.权利要求2所述的组合物,其中所用的枯茗提取物的用量为2.0mg到100mg之间。
4.权利要求1所述的组合物,其中在不考虑药物、营养物、维生素、营养药物、草药/产品、微量营养物和抗氧化剂等添加剂用量的情况下,来自枯茗的精馏产物的用量为约0.5mg到75.0mg范围。
5.权利要求1所述的组合物,其中来自枯茗的精馏产物的用量为约1.0mg到30mg范围。
6.权利要求1所述的组合物,其中来自枯茗的精馏产物选自精馏产物1-5。
7.权利要求1所述的组合物,其中胡椒碱的用量为约2mg到50mg范围,更具体为5mg到20mg之间。
8.权利要求1所述的组合物,其中胡椒碱分离自胡椒、筚拔或他们的树脂油。
9.权利要求1所述的组合物,其中药物选自以下这组药物:抗生素、抗真菌药、抗病毒药、抗癌药、心血管药、中枢神经系统疾病的药物、消炎药/治风湿药、抗结核药/抗麻风药、抗组胺剂/呼吸道疾病药物、皮质甾类、免疫抑制剂、治溃疡药和草药。
10.权利要求9所述的组合物,其中抗生素选自喹诺酮、大环内酯物、头孢菌素、青霉素和氨基糖苷这组物质。
11.权利要求10所述的组合物,其中喹诺酮选自环丙沙星、培氟沙星、氧氟沙星和诺氟沙星这组物质。
12.权利要求10所述的组合物,其中大环内酯物选自红霉素、罗红霉素和阿奇霉素这组物质。
13.权利要求10所述的组合物,其中头孢霉素选自头孢氨苄、头孢曲松、头孢克肟、头孢匹罗、头孢地尼和头孢羟氨苄这组物质。
14.权利要求10所述的组合物,其中青霉素选自阿莫西林和氯唑西林这组物质。
15.权利要求10所述的组合物,其中氨基糖苷选自阿米卡星和卡那霉素这组物质。
16.权利要求9所述的组合物,其中抗真菌药选自氟康唑、两性霉素B、灰黄霉素和酮康唑这组物质。
17.权利要求9所述的组合物,其中抗病毒药选择阿昔洛韦和叠氮胸苷这组物质。
18.权利要求9所述的组合物,其中抗癌药物选自甲氨蝶呤、5-氟尿嘧啶、阿霉素、紫杉醇和顺铂这组物质。
19.权利要求9所述的组合物,其中心血管药物选自氨氯地平、赖诺普利、普萘洛尔和阿替洛尔这组物质。
20.权利要求9所述的组合物,其中中枢神经系统药物选自阿谱唑仑和氟哌啶醇这组物质。
21.权利要求9所述的组合物,其中消炎药/治风湿药选自双氯芬酸钠、吡罗昔康、尼美舒利和罗非克西这组物质。
22.权利要求9所述的组合物,其中抗结核药/抗麻风药选自利福平、乙硫异烟胺、异烟肼、环丝氨酸、吡嗪酰胺、乙胺丁醇和氨苯砜这组物质。
23.权利要求9所述的组合物,其中抗组胺剂/呼吸道疾病药物选自沙丁胺醇、茶碱、溴己新和氯雷替定这组物质。
24.权利要求9所述的组合物,其中皮质甾类选自强的松龙、地塞米松和倍他米松这组物质。
25.权利要求9所述的组合物,其中免疫抑制剂选自环孢霉素A、他克莫司和霉酚酸酯这组物质。
26.权利要求9所述的组合物,其中治溃疡药化合物选自雷尼替丁、西咪替丁和奥美拉唑这组物质。
27.权利要求1所述的组合物,其中草药产品和草药材选自海胆、雪兰莪草、胡雪莲、木橘、穿心莲、白花酸藤果、总序天冬、绒毛诃子、催眠睡茄、积雪草和/或他们的混合物。
28.权利要求1所述的组合物,其中营养物选自糖、碳水化合物、脂肪和蛋白这组物质。
29.权利要求1所述的组合物,其中维生素选自维生素A、维生素E、维生素B1、维生素B6、维生素B12、维生素C和叶酸。
30.权利要求1所述的组合物,其中抗氧化剂选自β-胡萝卜素、水飞蓟素、硒、番茄红素和Ellagiogallotannins。
31.权利要求1所述的组合物,其中天然草药产品选自姜黄素、乳香酸和芸香苷这组物质。
32.权利要求1所述的组合物,其中必需微量营养物选自蛋氨酸、赖氨酸、亮氨酸、缬氨酸、异亮氨酸、锌、钙、葡萄糖、钾、铜和铁。
33.权利要求1所述的组合物,其中枯茗植物提取物或枯茗植物提取物的生物活性精馏产物提取自枯茗植物的任意部位。
34.权利要求1所述的组合物,其中以上所提到的组合物是通过口服、注射、鼻腔、吸入包括雾化、直肠、阴道、透皮作用和其他任意适合途径实现的。
35.权利要求1所述的组合物,其中将来自枯茗的植物提取物或生物活性精馏产物单独使用或与胡椒碱联合使用的生物提高作用在提高药物、营养药物、和草药/制剂的生物利用度/生物功效方面具有选择性。
36.权利要求1所述的组合物,其中单独含枯茗植物提取物或生物活性精馏产物的组合物提供生物利用度/生物提高活性为25-335%。
37.权利要求1所述的组合物,其中含枯茗的成分和胡椒碱的该组合物显示生物提高/生物利用度活性从接近显著的即约25%到非常显著的即约435%。
38.权利要求1所述的组合物,其中所述含胡椒碱和枯茗的组合物对生物利用度/生物提高活性比单独使用枯茗的生物提高活性高10%到85%。
39.权利要求1所述的组合物,其中枯茗的提取物的用量为10-75mg/kg/体重。
40.权利要求1所述的组合物,其中枯茗的生物活性精馏产物的用量为2-30mg/kg/体重。
41.权利要求1所述的组合物,其中胡椒碱的用量为0-12mg/kg/体重。
42.一种从枯茗植物制备其水提取物、含水醇提取物和生物活性精馏产物的方法,所述方法包括如下步骤:
a)粉碎植物,将其用水或50%的醇水溶液在95-100℃进行萃取,分别得到水提取物或醇水提取物,
b)将步骤(a)得到的一部分水提取物用正丁醇(n-BuOH)进行萃取,并分离正丁醇层和水层,
c)将步骤(b)得到的正丁醇层进行蒸发和冷冻干燥处理得到精馏产物1,
d)将步骤(b)得到的水层进行蒸发和冷冻干燥处理得到精馏产物2,
e)将步骤(a)得到的另一部分水层用醇进行回流,汇聚醇提取物并分离剩余的物质备用,
f)将步骤(e)汇聚得到的醇提取物进行蒸发,得到精馏产物3,
g)将步骤(e)的剩余物用50%的醇水溶剂进行提取,得到50%的醇水可溶部分,剩余物作为精馏产物5,和
h)将步骤(g)得到的醇水可溶部分进行蒸发,得到精馏产物4。
Applications Claiming Priority (2)
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US36346002P | 2002-03-12 | 2002-03-12 | |
US60/363,460 | 2002-03-12 |
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CN1649513A true CN1649513A (zh) | 2005-08-03 |
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US (2) | US7070814B2 (zh) |
EP (1) | EP1489924A2 (zh) |
JP (1) | JP2005519940A (zh) |
KR (1) | KR20040089733A (zh) |
CN (1) | CN1649513A (zh) |
AU (1) | AU2003209674A1 (zh) |
WO (1) | WO2003075685A2 (zh) |
ZA (1) | ZA200407968B (zh) |
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-
2003
- 2003-03-10 AU AU2003209674A patent/AU2003209674A1/en not_active Abandoned
- 2003-03-10 KR KR10-2004-7014398A patent/KR20040089733A/ko not_active Application Discontinuation
- 2003-03-10 JP JP2003573969A patent/JP2005519940A/ja active Pending
- 2003-03-10 EP EP03743977A patent/EP1489924A2/en not_active Withdrawn
- 2003-03-10 CN CNA038096617A patent/CN1649513A/zh active Pending
- 2003-03-10 WO PCT/IN2003/000052 patent/WO2003075685A2/en active Application Filing
- 2003-03-11 US US10/386,395 patent/US7070814B2/en not_active Expired - Lifetime
-
2004
- 2004-10-04 ZA ZA2004/07968A patent/ZA200407968B/en unknown
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- 2006-02-23 US US11/360,653 patent/US7514105B2/en not_active Expired - Lifetime
Cited By (7)
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CN102145172A (zh) * | 2011-01-28 | 2011-08-10 | 瑞普(天津)生物药业有限公司 | 一种提高氨基糖苷类药物吸收度的组合物 |
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CN103768026B (zh) * | 2014-02-18 | 2015-06-17 | 烟台金海药业有限公司 | 一种含有阿莫西林的可溶于水的微粉及其制备方法 |
CN110810467A (zh) * | 2019-11-19 | 2020-02-21 | 多麦(福建)食品有限公司 | 一种面包低温中种发酵烘焙工艺 |
CN115414366A (zh) * | 2022-08-23 | 2022-12-02 | 武汉科前生物股份有限公司 | 11-酮基-beta-乳香酸在制备治疗猫杯状病毒病的药物中的应用 |
CN115414366B (zh) * | 2022-08-23 | 2023-11-03 | 武汉科前生物股份有限公司 | 11-酮基-beta-乳香酸在制备治疗猫杯状病毒病的药物中的应用 |
Also Published As
Publication number | Publication date |
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KR20040089733A (ko) | 2004-10-21 |
US7070814B2 (en) | 2006-07-04 |
EP1489924A2 (en) | 2004-12-29 |
US20060141080A1 (en) | 2006-06-29 |
WO2003075685A3 (en) | 2003-11-06 |
AU2003209674A8 (en) | 2003-09-22 |
ZA200407968B (en) | 2005-09-28 |
US20040052873A1 (en) | 2004-03-18 |
WO2003075685A2 (en) | 2003-09-18 |
US7514105B2 (en) | 2009-04-07 |
AU2003209674A1 (en) | 2003-09-22 |
JP2005519940A (ja) | 2005-07-07 |
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