CN1111508A - 脂肪酸衍生物 - Google Patents

脂肪酸衍生物 Download PDF

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CN1111508A
CN1111508A CN95102756A CN95102756A CN1111508A CN 1111508 A CN1111508 A CN 1111508A CN 95102756 A CN95102756 A CN 95102756A CN 95102756 A CN95102756 A CN 95102756A CN 1111508 A CN1111508 A CN 1111508A
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ascorbyl
dgla
gla
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D·F·霍罗宾
P·诺里斯
M·S·曼库
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Abstract

在用于治疗哮喘和其它疾病的药物中的 Ascorbyl-GLA或Ascorbyl-DGLA。

Description

本发明涉及脂肪酸的抗坏血酸（维生素C）衍生物。
脂肪酸的抗坏血酸衍生物（1）是已知的。在下式中R是脂肪酸链，R1＝H或R，
Figure 951027565_IMG1
Kaneko等人在Arch.Biochm.Biophys.304        No.1，176-180（1993）中报道了抗坏血酸的6-O-棕榈酰基、6-O-硬脂酰基和2，6-O-二棕榈酰基酯和2-O-十八烷基醚衍生物所显示的在人体细胞培养物中抗亚油酸氢过氧化物的细胞毒性的保护作用。同样，也已描述了二十二碳六烯酸抗坏血酸酯的制备。
此外，已通过与磷酸化的一或二脂肪酰甘油酯一起使用抗坏血酸来保护不饱和脂肪酸不被空气氧化，所述的抗坏血酸可任意地是棕榈酸酯或硬脂酸酯形式（Cloughley，EPA93304827.4，基于UK        9213322.2）。
同样，在本发明人的许多先前的申请如EPA        0019423和EPA        0085579中已公开了将γ-亚麻酸（GLA）或二加碳-γ-亚麻酸（dihomo-γ-linolenic        acid，DGLA）与抗坏血酸共同服用的想法。
然而，通常人们很少注意脂肪酸的抗坏血酸酯，虽然Kanebo在JP-A-62081307中公开了在美容用组合物中的抗坏血酸的GLA酯。
当然，作为水溶性的、对健康来说必需的维生素，抗坏血酸是熟知的。但人们很少注意到这样一个事实，即，抗坏血酸能刺激DGLA转化成前列腺素E1（PGE1）。PGE1是一种具有特别广泛的理想作用的短寿命物质。它扩张血管、支气管和细支气管，抑制血小板凝集，发挥抗炎作用，降低胆固醇水平，降低血压，并且被认为具有一系列其它理想的作用，包括抗癌和抗转移作用。
鉴于PGE1的理想作用，在体内应该存在供其形成的最佳条件。一种企图确保这一点的方法是增加DGLA或其直接前体GLA的摄取。另一种方法是提供适当的抗坏血酸水平以促进PGE1形成。
现在，申请人发现，作为GLA和DGLA的6-抗坏血酸酯给出GLA和DGLA是特别有利的，下文中把GLA和DGLA的6-抗坏血酸酯称为Ascorbyl        GLA和Ascorbyl        DGLA。这些化合物可以通过如本文所述的在无机酸催化剂如氯化氢存在下在合适的溶剂如二甲基乙酰胺/二氯甲烷中在-10℃和30℃之间的温度下使所述脂肪酸的酰氯或酸酐反应来合成。它们在许多疾病中具有药物用途，本发明也提供它们在这样的疾病中的应用和在制备用于该目的的药物中的应用。所述的疾病包括：
（a）哮喘及有关病症，其中PGE1是有效并且安全的支气管扩张剂和抗炎剂，并且在扩张气管方面和长期抑制气管炎症方面都可能具有特别理想的作用，其中所说的气管炎症现在被认为是哮喘的主要因素，
（b）与动脉粥样硬化、和/或胆固醇升高、和/或高血压、和/或过度血小板凝集有关的心血管疾病，
（c）类风湿性关节炎、骨关节炎、皮炎和其它炎性疾病，
（d）癌症。
用途也包括美容用或皮肤护理用制剂，和任何类型的食品，并且特别是营养添加剂。
Ascorbyl DGLA的特别价值是同时并在完全相同的地方供给供PGE1生物合成用的直接底物DGLA和可促进底物DGLA转化成PGE1的刺激剂抗坏血酸酯。就申请人所知，化合物Ascorbyl-DGLA以前从未被描述过。
所述的酯可按0.1mg-50g/天，优选10mg-10g/天，更优选是100mg-5g/天的剂量以胶囊、片剂、香囊、溶液、乳液、粉剂、脂质体或其它形式通过口服、肠内或非经胃肠道途径给药。也可以将所述酯以乳油、软膏、洗剂、乳液、阴道栓、栓剂、粘贴剂（Sticks）或其它适当的形式局部使用，其中所述化合物的浓度按重量计为0.001%-50%，优选0.1%-20%，更优选为1%-10%。也可使用类似的浓度排放气溶胶、脂质体或其它适当的可确保药物直接排放到气管的排放体系。
一种特别适当的配制是将所述酯溶于或分散于游离脂肪酸或甘油三酯中，其中GLA、DGLA和/或其它抗炎脂肪酸EPA中的一种或多种是一个重要的组分，优选含5%重量或更多。特别合适的甘油三酯是含有1、2或3个选自GLA、DGLA和EPA的部分的甘油三酯。
合成实施例
6-（Z，Z，Z-十八碳-6，9，12-三烯酸）抗坏血酸酯的制备（可以按同样方法制备Ascorbyl        GLA和Ascorbyl        DGLA）
将氯化氢气体（2.0g）在0℃下鼓泡进入N，N-二甲基乙酰胺（26.5ml）。向所得淤浆中加入抗坏血酸（9.69g）在二氯甲烷（13.25ml）中的淤浆，在0℃搅拌混合物直至变成溶液。在0℃和氮气气氛下用4小时时间将Z，Z，Z-十八碳-6，9，12-三烯酰氯（14.8g）加到该溶液中，将所得混合物在上述温度下放置18小时，然后在室温下放置1小时。冷却至0℃后，加入乙酸乙酯（200ml）和水（100ml），将混合物搅拌1小时。有机层用盐水（5×100ml）洗涤，干燥（Na2SO4），并在50℃/10mmHg下蒸发，然后在50℃/0.1mm/4hr条件下蒸发，得到了浅黄色蜡状的6-[（Z，Z，Z）-十八碳-6，9，12-三烯酸]抗坏血酸酯（18.25g，88%）。
应用实施例
1.含50、100、250、500或750mg        Ascorbyl        GLA或Ascorbyl        DGLA的片剂，其中可以是Ascorbyl        GLA或Ascorbyl        DGLA本身，也可以含有适当的赋形剂。
2.含有50、100、250或500mg        Ascorbyl        GLA或Ascorbyl        DGLA的软明胶胶囊或硬明胶胶囊，所述的Ascorbyl        GLA或Ascorbyl        DGLA溶解在富含有GLA、DGLA或EPA的游离脂肪酸中或溶解在其中1、2或3个部分选自GLA、DGLA和EPA中的甘油三酯中。
3.浓度如本文所述的供将Ascorbyl        GLA或Ascorbyl        DGLA口服、肠内或非经胃肠道给药的乳液、粉剂、液体剂、浆状物或溶液。
4.浓度如本文所述的供将Ascorbyl        GLA或Ascorbyl        DGLA局部使用的软膏、乳油、洗剂、洗发剂或其它合适的制剂。
5.用磷脂或糖脂制成的、供Ascorbyl-DGLA口服、局部、非经胃肠道或直接气管排放用的脂质体。
6.含Ascorbyl-DGLA的喷雾剂（sprays）、混悬液、吸入剂或其它呼吸排放体系。

Claims (8)

1、Ascorbyl-GLA或Ascorbyl-DGLA在治疗下述疾病中或在制备用于治疗下述疾病的药物中的应用：
(a)哮喘及有关病症，
(b)与动脉粥样硬化、和/或胆固醇升高、和/或高血压、和/或过度血小板凝集有关的心血管疾病，
(c)类风湿性关节炎、骨关节炎、皮炎和其它炎性疾病，
(d)癌症。
2、根据权利要求1的Ascorbyl-GLA或Ascorbyl-DGLA的应用，其中配制所述酯以供每天使用0.1mg-50g，优选10mg-10g，而非常优选是100mg-5g。
3、根据权利要求1的Ascorbyl-GLA或Ascorbyl-DGLA的应用，其中将所述酯配制成浓度为0.001%-50%重量、优选0.1%-20%重量、而非常优选1%-10%重量的组合物。
4、根据权利要求1、2或3的Ascorbyl-GLA或Ascoebyl-DGLA的应用，其中是用于治疗哮喘和有关病症，将所述酯配制成供将其排放到呼吸道的混悬液、喷雾剂、气溶胶、脂质体或其它形式。
5、根据权利要求1、2或3的Ascorbyl-GLA或Ascorbyl-DGLA的应用，其中将所述酯与一种油混合来进行配制，所述油以游离脂肪酸或甘油三酯的形式含有5%重量或更多的GLA、DGLA或EPA。
6、Ascorbyl-DGLA本身以及用于治疗的或用于美容或皮肤护理制剂中的或用于包括营养添加剂在内的任何类型的食品中的Ascorbyl-DGLA。
7、用于治疗的或用于包括营养添加剂在内的任何类型的食品中的Ascorbyl-GLA。
8、配制成供向呼吸道排放的混悬液、喷雾剂、气溶胶、脂肪体或其它形式的Ascorbyl-GLA或Ascorbyl-DGLA。
CN95102756A 1994-03-01 1995-03-01 脂肪酸衍生物 Pending CN1111508A (zh)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101001607B (zh) * 2004-08-18 2010-09-29 三得利控股株式会社 含有6-o-pufa抗坏血酸酯的皮肤化妆料和饮食品
CN103384521A (zh) * 2010-12-21 2013-11-06 雀巢产品技术援助有限公司 用于预防和治疗骨关节炎的方法和组合物

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CN103384521A (zh) * 2010-12-21 2013-11-06 雀巢产品技术援助有限公司 用于预防和治疗骨关节炎的方法和组合物

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SG50339A1 (en) 1998-07-20
DE69523654T2 (de) 2002-08-01

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