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CN1200366A - 新l－苏糖酸衍生物 - Google Patents

新l－苏糖酸衍生物 Download PDF

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CN1200366A
CN1200366A CN97116835A CN97116835A CN1200366A CN 1200366 A CN1200366 A CN 1200366A CN 97116835 A CN97116835 A CN 97116835A CN 97116835 A CN97116835 A CN 97116835A CN 1200366 A CN1200366 A CN 1200366A
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于凯
王志文
寇福平
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Juneng Industry Co ltd
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Priority to JP2000508359A priority patent/JP2001514219A/ja
Priority to US09/486,569 priority patent/US6313170B1/en
Priority to PCT/CN1998/000174 priority patent/WO1999011256A1/zh
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Abstract

本发明涉及结构如右式的L－苏糖酸衍生物(其中:n=1时,X=K、Na、NH4,n=2时,X=Zn、Fe、Mg)的制备和应用,本发明的衍生物可作为体内常(微)量元素的补充剂用于医疗目的和营养保健。

Description

新L-苏糖酸衍生物
本发明涉及新的可作为药物应用的L-苏糖酸衍生物及其制备方法。
L-苏糖酸是维生素C的主要降解产物之一，维生素C的某些功能作用事实上是由其降解产物如L-苏糖酸等来具体实现的，反过来，这些降解产物的存在又对维生素C的生物功能或代谢机理发挥影响。L-苏糖酸钙为目前上市的一种保健药品，除了能够促进动物淋巴细胞对维生素C的吸收，还可以作为一种高效的分子型钙营养强化剂用于预防和治疗各种因缺钙引起的疾病，同时还发现在消炎止痛和降血压等方面有着明显的疗效，实验证明L-苏糖酸钙具有良好的药用价值，但L-苏糖酸的其他金属盐衍生物作为药物应用尚未见报导。
本发明提供了结构如下的L-苏糖酸衍生物：其中：n＝1时，X＝K、Na、NH4
  n＝2时，X＝Zn、Fe、Mg
本发明的L-苏糖酸衍生物的制备方法是：1、通过L-苏糖酸和钾、钠、铵、镁、锌、二价铁的某些无机盐、氧化物或氢氧化物进行中和反应得到；2、由L-苏糖酸钙和钾、钠、铵、镁、锌、二价铁的某些无机盐、氧化物或氢氧化物进行复分解反应得到。其中L-苏糖酸可以以维生素C为原料获得，也可以L-苏糖酸钙为原料直接由弱酸置换出其中的钙得到。
本发明中的L-苏糖酸亚铁具有左旋光学活性结构，易溶于水，在溶液中主要以络合结构形式存在，其中二价铁的稳定性较高。作为铁制剂具有高效吸收特点和缓释功能，是新型一代铁营养强化剂，可以预防和治疗由于缺铁而引起的缺铁性贫血、低血色素等疾病。L-苏糖酸铁既可以作为食品添加剂起到预防和保健的作用，也可以作为药剂起到治疗的效果。
具有一定生物活性和功能的L-苏糖酸做为小分子配体与锌离子的络合形成常数较大，所生成的L-苏糖酸锌在碱性条件下(pH～11)可以稳定存在，因此提高了吸收率和利用率，同时有缓释效果而使血清锌浓度不产生大的波动，并且使其在体内的代谢时间延长，减小其毒性和副作用，可以在食品中作为添加剂或用作补锌药和收敛药，来预防和治疗由于缺锌所引起的各种疾病。
L-苏糖酸镁的物化性质与L-苏糖酸钙相类似，但L-苏糖酸镁的用途主要是作为泻药和利胆药，也可以是针剂作为抗惊厥药用。
L-苏糖酸钠、L-苏糖酸钾用于补充体内电解质，维持电解质平衡
L-苏糖酸铵可以用作祛痰药和辅助利尿药。
本发明的L-苏糖酸衍生物可以制成任何一种药物剂型，如：片剂，胶囊剂，溶液剂，悬浮剂，乳剂，凝胶剂，软膏剂，冻干粉剂，滴丸剂，膜剂，脂质体。
本发明的L-苏糖酸衍生物组合物中可以包括任何一种药物可接受的载体、药用辅料。组合物中L-苏糖酸衍生物的含量可依据给药、使用方法以及病症的不同而异，口服剂量在1mg～100g之间的范围内，优选的是10mg～10g，成人每天1到6次。
以下为本发明的实施例，用于说明本发明，但不作为对本发明的限制：实施例一、L-苏糖酸锌的制备
Figure A9711683500051
将0.1mol维生素C溶解于500ml水中，维持搅拌下慢慢向其中加入0.13mol碱式碳酸锌(ZnCO3·2Zn(OH)2·HO2)粉末，控制溶液温度＜10℃。待反应完全后，开始向反应混合液中滴加30％的过氧化氢水溶液40ml(0.35mol)，充分搅拌并维持反应温度在30～40℃至滴加完毕。当反应进行2h后，向体系中加入活性碳并将体系温度升高至80℃以上除去过量的过氧化氢。趁热过滤后将滤液减压浓缩至100ml，静置析出晶体，在蒸馏水中重结晶后于室温下干燥，得到产物含两个结晶水的L-苏糖酸锌，C8H14O10Zn·2H2O，元素分析结果(％)：计算值，C25.83，H4.88，Zn17.59；  实验值C25.35，H4.75，Zn17.21。当在50℃时进行真空干燥(10mmHg)后得到含一个结晶水的L-苏糖酸锌C8H14O10Zn·H2O，元素分析结果(％)：计算值，C27.15，H4.56，Zn18.48；  实验值C26.98，H4.77，Zn17.96。当在100℃时进行真空干燥(5mmHg)后得到不含结晶水的L-苏糖酸锌C8H14O10Zn，元素分析结果(％)：计算值，C28.61，H4.21，Zn19.48；实验值C28.24，H3.95，Zn19.89。实施例二、L-苏糖酸亚铁的制备其合成路线和方法如下：
Figure A9711683500061
将0.1mol维生素C溶解于500ml二次蒸馏水中，以0.1mol/L的NaOH调节溶液酸度为弱碱性(pH＝7～9)，向溶液中滴加30％的过氧化氢水溶液40ml(0.35mol)，充分搅拌并在10℃的温度下维持反应20h。向体系中加入活性碳并将体系温度升高至80℃以彻底除去过量的过氧化氢，将溶液过滤，当滤液冷却至室温后，在氮气气氛下缓慢加入0.15mol硫酸亚铁(FeSO4·2HO2)。待全部硫酸亚铁加完并溶解后，将反应溶液进行减压浓缩，浓缩液在静置中便析出淡绿色晶体。将它在二次蒸馏水中进行两次重结晶，于室温下真空干燥器中干燥，得到产物含两个结晶水的L-苏糖酸亚铁，C8H14O10Fe·2H2O，元素分析结果(％)：计算值，C26.52，H5.01，Fe15.42；实验值C26.66，H4.91，Fe15.23。当在60℃温度下真空干燥后(10mmHg)得到含一个结晶水的L-苏糖酸亚铁C8H14O10Fe·H2O，元素分析结果(％)：计算值，C27.91，H4.69，Fe16.23；实验值C27.66，H4.94，Fe16.53。当在120℃温度下真空干燥后(5mmHg)得到无结晶水的L-苏糖酸亚铁C8H14O10Fe，元素分析结果(％)：计算值，C29.45，H4.33，Fe17.13；实验值C29.11，H4.39，Fe17.60。实施例三、L-苏糖酸镁的制备其合成路线如下：
L-苏糖酸镁的合成方法同合成L-苏糖酸锌的方法相同，得到的产物在室温下干燥得到C8H14O10Mg·2H2O，元素分析结果(％)：计算值，C29.05，H5.49，Mg7.35：实验值C28.44，H5.98，Mg7.55。该产物进一步在室温25℃进行真空脱水得到了C8H14O10Mg·H2O，元素分析结果(％)：计算值，C30.72，H5.16，Mg7.78；实验值C30.14，H5.33，Mg8.09。将含有一个结晶水的L-苏糖酸镁继续在约60℃下脱水得到了C8H14O10Mg，元素分析结果(％)：计算值，C32.60，H4.79，Mg8.25；实验值C32.14，H4.98，Mg8.57。实施例四、L-苏糖酸钠的制备
取13.4g L-苏糖酸(0.1mol)溶解于100ml的水中，在搅拌下加入等摩尔的碳酸氢钠(NaHCO3)的水溶液，加热除去体系中的二氧化碳，待反应结束后将反应混合液进行浓缩近干，析出无色晶体即为粗产物，再经蒸馏水中重结晶得到无色细小晶体，过滤收集并置于干燥器中干燥。进行元素分析的结果为(％)：C4H7O5Na(计算值，C30.37，H4.46；实验值，C30.14，H4.78)。实施例五、L-苏糖酸钾的制备
Figure A9711683500091
将新制备的L-苏糖酸钙(0.1mol)溶解于水中，向其中加入等摩尔的草酸钾K2C2O4水溶液，搅拌使反应维持0.5h后过滤，浓缩滤液至原来体积的五分之一，静置后析出产物，在蒸馏水中二次重结晶得到产物L-苏糖酸钾，元素分析结果为(％)：C4H7O5K(计算值，C27.56，H4.05，K22.44；实验值，C27.79，H4.48，K22.52)。实施例六、L-苏糖酸铵的制备
Figure A9711683500092
于0.1mol的L-苏糖酸钙水溶液中加入0.2mol的磷酸氢铵((NH4)2HPO4)和0.2mol的氨水溶液(NH3·H2O)，搅拌使反应维持0.5h后过滤，浓缩滤液至原来体积的五分之一，静置后析出产物并在蒸馏水中进行二次重结晶提纯，于空气中自然干燥即可，元素分析的结果为(％)；C4H7O5NH4(计算值，C31.35，H4.61；实验值，C31.14，H4.22)。实施例七、L-苏糖酸的制备
在0.2mol/L维生素C的溶液(100ml)中(以冰水浴控制温度为4℃)加入4g碳酸钙，当其全部溶解后再向其中滴加30％的H2O2水溶液10ml，搅拌条件下在温度为30～40℃范围内维持反应1h。然后向体系中加入1.5g活性碳并升高体系温度至80℃以破坏过量的H2O2，溶液趁热过滤，滤液在40℃下减压浓缩至原来体积的三分之一，加入适量的甲醇，静置数小时后析出L-苏糖酸钙的微晶，过滤，晶体用80％的甲醇水溶液洗涤两次后转移至一烧瓶中，向其中慢慢滴加稀的草酸(硫酸或磷酸)溶液，当溶液pH值等于5～7时停止滴加。将溶液过滤，放置后析出L-苏糖酸晶体。实施例八、L-苏糖酸锌胶囊剂的制备处方：L-苏糖酸锌         45g维生素C            100g  淀粉                 10g羧甲基淀粉钠         20g低取代羟丙基纤维素   10g十二烷基磺酸钠       8g0号胃溶胶囊          1000g
将上述原辅料混合均匀，添充胶囊制成1000粒L-苏糖酸锌胶囊实施例九、L-苏糖酸亚铁片剂的制备处方：L-苏糖酸亚铁             48.5g维生素C                  30g甘露醇                   180g淀粉                     80g香精                     适量硬脂酸镁                 适量
经制粒、干燥、压片制成1000片L-苏糖酸亚铁片剂实施例十、L-苏糖酶钠注射剂的制备处方：L-苏糖酸钠            4g氯化钠                6.00g氯化钾                0.30g氯化钙(CaCl2·2H2O)0.20g注射用水  适量
溶解后，调pH值，加注射用水至1000mL，制成1000mL L-苏糖酸钠注射液。

Claims (11)

1、结构如下式的L-苏糖酸衍生物：
Figure A9711683500021
其中：n＝1；X＝K、Na、NH4
  n＝2；X＝Zn、Fe、Mg
2、权利要求1的化合物是L-苏糖酸亚铁。
3、权利要求1的化合物是L-苏糖酸锌。
4、权利要求1的化合物是L-苏糖酸钾。
5、权利要求1的化合物是L-苏糖酸钠。
6、权利要求1的化合物是L-苏糖酸镁。
7、权利要求1的化合物是L-苏糖酸铵。
8、权利要求1的化合物的制造方法。
9、权利要求1化合物的药物组合物。
10、权利要求1化合物的具有保健作用的组合物。
11、权利要求1化合物的具有保健作用和药物作用的组合物是片剂、针剂、胶囊剂、注射剂、口服液和颗粒剂。
CN97116835A 1997-08-29 1997-08-29 新l－苏糖酸衍生物 Expired - Fee Related CN1053653C (zh)

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Application Number Priority Date Filing Date Title
CN97116835A CN1053653C (zh) 1997-08-29 1997-08-29 新l－苏糖酸衍生物
DE69832722T DE69832722T2 (de) 1997-08-29 1998-08-28 Eisen-l-threonat-,pharmazeutische zusammensetzungen und deren verwendung zur verbesserung und behandlung von anämie bei menschen
HK01102229A HK1032534A1 (zh) 1997-08-29 1998-08-28 L-蘇糖酸亞鐵，其藥用組合物以及在改善和治療人體貧血中的應用
AU88512/98A AU8851298A (en) 1997-08-29 1998-08-28 L-threonate ferrous, as well as pharmaceutical composition and use for improvingand treating human anemia thereof
KR1020007002104A KR100615537B1 (ko) 1997-08-29 1998-08-28 제 1철 ｌ-트레오네이트, 그 약학 조성물 및 인간의 빈혈을 개선 및 치료하기 위해 이를 사용하는 방법
EP98940049A EP1038524B1 (en) 1997-08-29 1998-08-28 L-threonate ferrous, as well as pharmaceutical composition and use for improving and treating human anemia thereof
JP2000508359A JP2001514219A (ja) 1997-08-29 1998-08-28 Ｌ−トレオン酸第１鉄、その医療組成物及び人間の貧血疾患を改善及び治療するためのその使用
US09/486,569 US6313170B1 (en) 1997-08-29 1998-08-28 L-threonate ferrous, as well as pharmaceutical composition and use for improving and treating human anemia thereof
PCT/CN1998/000174 WO1999011256A1 (en) 1997-08-29 1998-08-28 L-threonate ferrous, as well as pharmaceutical composition and use for improving and treating human anemia thereof

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EP (1) EP1038524B1 (zh)
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AU (1) AU8851298A (zh)
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WO2000010962A1 (fr) * 1998-08-18 2000-03-02 Beijing Juneng Asia Pacific Life Scientific Research Center L-threonate de chrome, son procede de preparation et son application
US8142803B2 (en) 2007-03-22 2012-03-27 Magceutics, Inc. Magnesium compositions and uses thereof for neurological disorders
CN102573496A (zh) * 2009-07-01 2012-07-11 玛格塞蒂克斯公司 缓释镁组合物及其用途
JP2013155197A (ja) * 2007-03-22 2013-08-15 Guosong Liu マグネシウム組成物およびその使用
CN104961636A (zh) * 2015-07-14 2015-10-07 启东东岳药业有限公司 L-苏糖酸镁合成方法
CN105326855A (zh) * 2015-10-27 2016-02-17 南京大学 易吸收复合夹层式螯合镁钙片

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JP4300753B2 (ja) * 2001-05-31 2009-07-22 味の素株式会社 貧血抑制剤及び食欲抑制剤
CN1197561C (zh) * 2001-07-03 2005-04-20 北京巨能亚太生命科学研究中心 L－苏糖酸钙在制备预防或治疗损及软骨的疾病的药物中的用途
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US6548687B1 (en) 1998-08-18 2003-04-15 Kai Yu Chromium L-threonate, process for preparation of the same and their use
US9616038B2 (en) 2007-03-22 2017-04-11 Neurocentria, Inc. Magnesium compositions and uses thereof for neurological disorders
US8142803B2 (en) 2007-03-22 2012-03-27 Magceutics, Inc. Magnesium compositions and uses thereof for neurological disorders
US8178133B2 (en) 2007-03-22 2012-05-15 Magceutics, Inc. Magnesium compositions and uses thereof
US8178118B2 (en) 2007-03-22 2012-05-15 Magceutics, Inc. Magnesium compositions and uses thereof for cognitive function
US8178132B2 (en) 2007-03-22 2012-05-15 Magceutics, Inc. Magnesium-containing food compositions
CN113143901A (zh) * 2007-03-22 2021-07-23 纽罗森特里亚股份有限公司 镁组合物及其用途
CN107412217A (zh) * 2007-03-22 2017-12-01 纽罗森特里亚股份有限公司 镁组合物及其用途
JP2013155197A (ja) * 2007-03-22 2013-08-15 Guosong Liu マグネシウム組成物およびその使用
US8637061B2 (en) 2007-03-22 2014-01-28 Magceutics, Inc. Magnesium compositions and uses thereof for neurological disorders
US9757414B2 (en) 2007-03-22 2017-09-12 Neurocentria, Inc. Magnesium compositions and uses thereof for neurological disorders
US8163301B2 (en) 2007-03-22 2012-04-24 Magceutics, Inc. Magnesium compositions and uses thereof for metabolic disorders
US9125878B2 (en) 2007-03-22 2015-09-08 Magceutics, Inc. Magnesium compositions and uses thereof for neurological disorders
US9737563B2 (en) 2007-03-22 2017-08-22 Neurocentria, Inc. Magnesium compositions and uses thereof for neurological disorders
CN104161744B (zh) * 2007-03-22 2017-04-12 纽罗森特里亚股份有限公司 镁组合物及其用途
JP2016029073A (ja) * 2007-03-22 2016-03-03 リュー，グオソン マグネシウム組成物およびその使用
CN102573496B (zh) * 2009-07-01 2015-08-26 玛格塞蒂克斯公司 缓释镁组合物及其用途
US8734855B2 (en) 2009-07-01 2014-05-27 Magceutics, Inc. Slow release magnesium composition and uses thereof
US8377473B2 (en) 2009-07-01 2013-02-19 Magceutics, Inc. Slow release magnesium composition and uses thereof
CN102573496A (zh) * 2009-07-01 2012-07-11 玛格塞蒂克斯公司 缓释镁组合物及其用途
CN104961636B (zh) * 2015-07-14 2016-08-31 启东东岳药业有限公司 L-苏糖酸镁合成方法
CN104961636A (zh) * 2015-07-14 2015-10-07 启东东岳药业有限公司 L-苏糖酸镁合成方法
CN105326855A (zh) * 2015-10-27 2016-02-17 南京大学 易吸收复合夹层式螯合镁钙片

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CN1053653C (zh) 2000-06-21
KR100615537B1 (ko) 2006-08-25
HK1032534A1 (zh) 2001-07-27
KR20010023461A (ko) 2001-03-26
WO1999011256A1 (en) 1999-03-11
JP2001514219A (ja) 2001-09-11
EP1038524A4 (en) 2002-08-07
US6313170B1 (en) 2001-11-06
WO1999011256A8 (en) 1999-08-05
DE69832722D1 (de) 2006-01-12
AU8851298A (en) 1999-03-22
DE69832722T2 (de) 2006-09-07
EP1038524B1 (en) 2005-12-07
EP1038524A1 (en) 2000-09-27

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