CN1420843A - 原硅酸的制备方法,获得的原硅酸,和它的用途 - Google Patents
原硅酸的制备方法,获得的原硅酸,和它的用途 Download PDFInfo
- Publication number
- CN1420843A CN1420843A CN00818256A CN00818256A CN1420843A CN 1420843 A CN1420843 A CN 1420843A CN 00818256 A CN00818256 A CN 00818256A CN 00818256 A CN00818256 A CN 00818256A CN 1420843 A CN1420843 A CN 1420843A
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- Prior art keywords
- silicon
- orthosilicic acid
- acid
- carrier
- orthosilicic
- Prior art date
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Abstract
本发明涉及一种原硅酸的制备方法,其中在非毒性溶剂试剂存在下,在原硅酸形成下,在酸溶液中水解可酸水解硅化合物,其中优选将形成的原硅酸与非毒性微粒载体接触,和涉及硅制剂在动物饲料、食品、食品或饲料补充物、和药物或化妆品制剂生产中的用途。
Description
本发明涉及原硅酸的制备方法,涉及可通过此方法获得的原硅酸和涉及它作为硅氧烷制剂在动物饲料、食品、食品或饲料补充物的生产中、和用于药物或化妆品制剂生产中的用途。已经认为硅(Si)是硅藻类,硅蓄积植物和高级动物的必要痕量元素。硅在脊椎动物中的最好的已经证明了的功能是它在骨钙化中的调节作用和它与结缔组织中细胞外基质的几种组分的化学缔合(Carlisle E.(1989),硅,在:Handbook ofNutritionally Essential Mineral Elements ed.B.L.O’Dell andR.A.Sunde,Marcel Dekker Inc.,纽约,603-618页)。此基质主要由嵌入水合多糖凝胶的纤维蛋白如胶原蛋白组成。认为结合到此基质组分上的硅对于结构完整性,结缔组织的发育和调节功能是重要的。硅的胃-肠吸收仅在饮食硅-化合物水解成原硅酸之后才是可能的。硅化合物在饮食中的溶解性较低,因此这些化合物的生物可利用性有限。未在生物系统中发现包括硅-C键的有机化合物,并发现几类合成产物具有不可接受的毒性。天然溶解性硅化合物,也称为单体硅酸的原硅酸在淡水和海水中都存在,但浓度非常低(<1mmoll-1[Sullivan C.(1986)由硅藻类的硅化,在:Silicon Biochemistry,CIBA Foundation Symposiuml21,John Wileyand Sons,纽约,24-39页])。在含水介质中的更高浓度引发聚合反应变成生物不可利用的胶体并最终成为凝胶。稳定化原硅酸制剂的制备方法公开于US5,922,360。
本发明的目的是提供一种从相对便宜和市场可得的起始材料开始,同时基本避免形成的原硅酸聚合的原硅酸制备方法。
此目的可采用根据本发明的原硅酸制备方法获得,其中非毒性溶剂试剂存在下,在原硅酸的形成下,将可酸水解的硅化合物在酸溶液,如酸水溶液中水解。由于使用酸溶液和由于非毒性溶剂试剂的存在基本抑制了上述聚合反应并且形成的原硅酸是足够稳定的。
起始材料,它是可酸水解硅化合物,可选自硅酸盐,如单体硅酸盐,如硅卤化物、原硅酸甲酯、原硅酸钠或镁,或选自水合硅酸盐如结晶硅酸钠。
其中R1,R2,R3和R4独立地选自H、C1-C12烷基、任意地被羟基取代的C1-C12烷氧基,条件是R1,R2,R4和R4不同时为H。优选,R1,R2,R3和R4选自H、C1-C4烷基、任意地被羟基取代的C1-C4烷氧基。注意优选选择R1,R2,R3和R4使得从可水解硅化合物分裂出的化合物可使用传统技术如蒸发和蒸馏除去,最优选的是非毒性的(大鼠中的口服LD50高于1g/kg体重)。最优选的硅化合物是四乙氧基硅烷醇。
R的其它优选例子是C2H5、CH3CO、HCO、C3H7、C4H9和CH3CH(OH)CHCO。溶液可包括1-80%,优选10-70%,更优选40-60%溶剂试剂。
用于酸溶液以稳定形成的原硅酸的非毒性溶剂试剂可选自二醇、甘油、(聚)亚烷基二醇、DMSO和聚山梨酸酯80。(聚)亚烷基二醇可以是聚丙二醇或聚乙二醇。亚烷基二醇可以是乙二醇或丙二醇。对于所有非毒性溶剂试剂的通常类性能是在水中的高溶解性(大于30%),高于130℃的沸点,在-10℃到40℃下为液态和在一般0-4的酸pH下稳定。
由非毒性溶剂试剂稳定的形成的原硅酸,可以通过将原硅酸与非毒性微粒载体接触而进一步稳定。
令人惊奇地,体验到吸附原硅酸的此非毒性微粒载体具有生物可利用性,它可以与稳定化制剂相比甚至有改进,如在US5,922,360中公开的那样。生物可利用性是关键的因素,这是由于近来显示在比较人体补充物研究中,固体硅补充物如胶体二氧化硅和植物性硅酸盐不是生物可利用的,而稳定的原硅酸在HCl-胆碱基质中的溶液具有高的生物可利用性[Calomme M.,Cos P.,Vingerhoets R.,Van Hoorebeke C.,VandenBerghe D.(1998)硅补充物在健康对象中的比较生物可利用性研究,Journal of Parenteral and Enteral Nutrition,22,S12,(文摘#47)Van Dyck K.,Van Cauwenbergh R.,Robberecht H.,DeelstraH.(1999),来自食品和食品补充物的硅的生物可利用性,FreseniusJournal of Analytical Chemistry,363,541-544]。因此,本发明也提供硅制剂,包括吸附在微粒载体上的原硅酸,通过包括如下步骤的方法获得:
i)提供溶液,包括采用该酸溶剂试剂稳定化的原硅酸;和
ii)将包括原硅酸的溶液与微粒载体接触。
为避免达到原硅酸聚合的另外程度,优选原位形成原硅酸。当在与原硅酸接触之后将载体挤出时,硅制剂的剂型的处理和形成得到进一步改进。
熟练技术人员会认识到依赖于硅制剂的所需用途,根据本发明的硅制剂可包含在宽硅含量范围的原硅酸。一般情况下,硅制剂的硅含量在0.01-50wt%,优选0.01-10wt%,更优选0.1-10wt%,最优选0.1-5wt%的范围内。因此,硅制剂可用于适于最希望的食品、饲料、药物和化妆品用途的剂量方案。在此方面,注意到药物和化妆品制剂可对指甲、头发、皮肤、牙齿、胶原蛋白、结缔组织、骨头、促进细胞增生、刺激免疫系统抗感染和毒物和抑制变性(老化)过程有积极的效果。此外,注意到溶剂试剂和载体应当是非毒性的,它意味着在人体、动物和植物中不引发毒副反应效果。
使用根据本发明的硅制剂的试验已经显示,硅制剂具有所需的高生物可利用性,表达为由有机体如人体的总的硅吸收。与前述胶体和植物性二氧化硅制剂相比,在0-8小时内的相对生物可利用性得到更大改进。换言之,在8小时内的总硅吸收量大于250(μg)硅h/l,优选大于500(μg)硅h/l,更优选大于600(μg)硅h/l,如250-700(μg)硅h/l,优选300-700(μg)硅h/l。
吸附在载体上的根据本发明的硅制剂可以以这样的形式使用或与任何可接受的载体材料、赋形剂或稀释剂结合使用。
根据本发明的硅制剂可以口服给予或以任何其它合适的方式给予。口服给药是优选的并且硅制剂的形式可为片剂、含水分散体、可分散粉末或颗粒、乳液、硬或软胶囊、糖浆、酏剂或凝胶。剂型可以使用在制造这些药物或化妆品组合物领域已知的任何方法制备,并可包括添加剂如甜料、调味剂、着色剂、防腐剂等。载体材料和赋形剂可包括碳酸钙、碳酸钠、乳糖、磷酸钙或磷酸钠、成颗粒剂和崩解剂、粘合剂等。硅制剂可包括在与任何惰性固体稀释剂或载体材料混合的明胶胶囊中,或具有软明胶胶囊的形式,其中将该成分与水或油介质混合。含水分散体可包括与悬浮剂、分散剂或润湿剂结合的硅制剂。油分散体可包括悬浮剂如植物油。可以按照在US5,922,360中的教导制备凝胶制剂。
目前可以制备载体结合的原硅酸与如下其它组分的干燥混合物:如痕量元素、维生素、氨基酸、糖、植物提取物、和用于生产食品和食品补充物的其它成分。作为解释,考虑到在载体结合的原硅酸中原硅酸保持它的单体形式,因此不同于原硅酸的生物不可利用的聚合形式物如在胶体或固体硅酸和硅酸盐中。
例如在酸溶剂试剂存在下并且在原位,通过如下方式制备原硅酸:(a)单体硅化合物如硅卤化物或原硅酸甲酯的水解[Iler R.(1979)单硅酸,在:硅化学,John Wiley and Sons,纽约,178-180页],(b)将单体硅酸盐如原硅酸钠或镁或水合结晶硅酸钠与稀酸反应[Iler 1979],(c)水解有机烷基硅烷醇化合物。注意到在形成的原硅酸之后,其它水解反应化合物应当是非毒性的并且如需要应当从反应混合物中除去。优选,烷基硅烷醇化合物是乙氧基硅烷醇化合物,并且形成的乙醇可以不费力地分离。新鲜制备的原硅酸结合到载体上或是载体的结合物上。第二种方法是首先将有机硅化合物结合到载体上,其后例如在低于4,如0.2-2.5,更优选0.8-1.0的pH下,将有机硅化合物水解成原硅酸。
固体载体或固体载体的结合物可选自:
i)天然和半合成纤维,
ii)植物代谢物如polyfenol、木脂素、黄酮类化合物,
iii)脂肪酸及其酯如硬脂酸酯、棕榈酸酯、亚油酸酯、油酸酯、己二酸酯、辛酸酯、癸酸酯、椰子酯(cocoates),
iv)磷脂及其衍生物,
v)多醇如肌醇、海藻糖,
vi)氢化和硫酸化化合物,
vii)盐如氯化物、硫酸盐、硝酸盐等,
viii)果胶和藻酸盐,
ix)糖或糖醇及其衍生物如乳糖、蔗糖、甘露糖醇、山梨糖醇、山梨醇酯,
x)多糖或低聚糖硅acharides及其衍生物如葡聚糖、果聚糖、菊粉、低聚果糖,
xi)明胶或其衍生物如明胶水解产物,
xii)纤维素或其衍生物如微晶纤维素、羟丙基纤维素、羟丙基甲基纤维素、羧甲基纤维素、纤维素树胶,
xiii)肽和多肽如如胶原蛋白、大豆蛋白、玉米面球蛋白及其衍生物,
xiv)葡聚糖及其衍生物如蛋白聚糖、葡糖胺聚糖、玻璃糖醛酸、硫酸软骨素、肝素、硫酸乙酰肝素、硫酸角质素、硫酸皮肤素。
xv)淀粉及其衍生物,
xvi)卵磷脂及其衍生物,如
xvii)食品生产的副产物,如来自乳酪、啤酒和玉米的发酵副产物,和乳酪乳清,
xviii)食品副产物如干燥动物食品、用于植物的基质如用于植物生产的天然泥炭、干燥植物提取物是干燥植物匀浆和化妆品粉末如滑石。
实例例A
按如下方式制备原硅酸。将两升冷硅酸钠的新鲜溶液(14%NaOH中的27%SiO2)与2-4升甘油(前分析,100%)混合,直到获得均匀的溶液。为降低pH,加入一升冷,浓盐酸和将混合物在0-10℃的温度下剧烈搅拌。在连续混合期间,加入碳酸钙的固体或悬浮液直到获得1-3的pH。在混合期间,会形成CO2气体。
将半升新制备的浓原硅酸结合物与如下物质混合:0.5kg明胶,或0.5kg乳酪乳清,或200g纤维素,或1kg半乳糖,或1kg蔗糖。混合所得的糊剂直到获得均匀的糊剂。将糊剂在真空中干燥。最终产物包含最小0.1%元素硅和优选1-5%元素硅。
在2个月期间0.5g的每日摄入量导致在四个不同的人中指甲和头发质量的改进。此改进等同于使用US5,922,360中制剂观察到的情况。
实施例B
将载体(65%)微晶纤维素与35%浓原硅酸和甘油(参见实施例A)的结合物混合。在连续混合期间加入软化水以获得合适量的颗粒化材料。采用篮式挤出机(Caleva型10,Sturminster Newton,Great Britain)在750rpm下挤出塑性本体。将挤出条团成球状(Caleve型120成球机)。将获得的粒料干燥到最终水含量小于5%。典型的粒料尺寸为800-1200μm。在尺寸00的硬明胶胶囊中封囊粒料。每个胶囊包含0.54g粒料,等于5mg以载体结合原硅酸形式的元素硅。微晶纤维素的负载能力可以增加到45%原硅酸。
实施例C
将载体,大豆蛋白质和玉米面球蛋白质的混合物(1∶1)(70%)与30%原硅酸与甘油的结合物(参见实施例A)混合。在连续混合期间加入软化水以获得均匀的塑性本体。将混合物通过冻干法干燥。在成颗粒之后,将蛋白质结合的原硅酸直接封囊或用作动物饲料、食品、食品补充物、化妆品或药物制剂的原材料。
实施例D
将载体(65%),微晶纤维素和果聚糖的混合物(3∶1)与35%浓原硅酸与甘油的结合物(参见实施例A)混合。在连续混合期间加入软化水以获得合适量的颗粒化材料。采用篮式挤出机(Caleva型10,SturminsterNewton,Great Britain)在750rpm下挤出塑性本体。将挤出条团成球状(Caleve型120成球机)。将获得的粒料干燥到最终水含量小于5%。典型的粒料尺寸为800-1400μm。将粒料压成片剂或用作动物饲料、食品、食品补充物、化妆品或药物制剂的原材料。
实施例E
将100ml冰冷四乙氧基硅烷醇缓慢滴加到1升50%冰冷甘油水溶液中,pH1.0。在0℃下8h之后,硅烷醇化合物完全水解。通过在真空下的快速蒸发除去乙醇。
将剩余的OSA溶液与作为糊剂的2-3kg乳糖混合和进一步在真空下干燥。最终产物包含最小0.1%硅和优选0.3-2%硅。
实施例A-E制剂的溶解测定显示原硅酸在30分钟之内释入到溶解介质中。这可通过在固定时间点,采用Zeeman校正的电热原子吸收光谱(Perkin Elmer)仪,测量溶解介质的硅含量而说明。原硅酸在溶解期间释放的事实清楚地说明了原硅酸对载体的结合并不导致原硅酸的聚合,而保留为可分离的形式。在生产日期3,6和12个月之后,重复溶解测定,没有差异的结果显示载体结合的原硅酸在较长时间内是化学稳定的。
实施例F
在被告知,写下同意书之后,征集三个健康对象(2个女性,1个男性,年龄22-34岁)。在开始研究之前3个月之内没有人摄入硅补充物。每个禁食对象接受如下的交叉方案口服硅:在每次补充物或安慰剂之间1周清除时间内接受形式为稳定化原硅酸的10mg硅(原硅酸,0.5ml包含20g硅/l的BioSil,如在US5,922,360中那样),形式为载体结合的原硅酸的10mg硅(实施例D的胶囊制剂),形式为胶体二氧化硅的20mg硅(聚合的原硅酸),形式为植物性二氧化硅的20mg硅(硅-蓄积植物田野木贼属的标准化干燥提取物)或安慰剂(10ml矿泉水)。在补充之前和在补充后1,2,4,6和8小时,采集血样置于无硅的聚丙烯管中。在实验期间在补充2和6小时之后,消耗相同的膳食。在一个批次中采用AAS测量每个对象的血清和尿中的硅浓度。装配有HGA-600石墨炉的Zeeman/3030原子吸收光谱仪与AS-60自动采样器(Perkin-Elmer Corp.Norwalk CT)结合使用。使用线性梯形原则作为总硅吸收的目标参数,计算在时间浓度曲线(A.U.C.)下的面积。在补充液体原硅酸和载体结合原硅酸之后(图1原硅酸=OSA),血清硅浓度都从基线值显著增加,但在补充聚合原硅酸形式物如胶体二氧化硅或植物性二氧化硅之后,并不增加。相比于液体原硅酸,载体结合原硅酸的动力学吸收图指示较缓慢的释放作用。对于载体结合的原硅酸和液体原硅酸来说,总体生物可利用性相似,但原硅酸聚合形式物并不是生物可利用的,这是由于与安慰剂相比,这些产品看不出显著的差异(图2原硅酸=OSA)。在载体结合的原硅酸生产日期一年之后,重复生物可利用性试验,结果没有显著的差异,说明载体结合的原硅酸在较长时间内是化学稳定的,没有显著的生物可利用性损失。图3说明采用如下形式10mg硅补充的志愿者(n=3)血清中的动力学分布:(a)OSA液体,(b)新鲜制备的载体结合OSA,和(c)1年期的载体结合OSA。计算为时间曲线(A.U.C.)下的面积的相对生物利用性在不同硅形式物之间没有显著差异(平均值±SD):分别是:安慰剂为132±28μg/L,OSA液体为795±231μg/L,新鲜制备的载体结合OSA为869±448μg/L,和对于1年期载体结合OSA为622±251μg/L。
实施例G
将用于母猪的饲料粒料(‘载体’)与浓原硅酸和甘油的结合物(参见实施例A)混合,直到获得形式为载体结合OSA的浓度为15mg硅/kg饲料。在受胎之前1周直到断奶,每天喂给母猪4kg此‘载体结合OSA’饲料。对照组母猪接受正常的饲料,除了没有载体结合OSA以外其余组成相同。从4周龄的小猪(断奶)抽取血液,并采用石墨炉原子吸收光谱测量血清中硅浓度。喂养‘载体结合OSA’饮食的小猪的平均血清硅浓度比对照组高150%(表1),它清楚地说明(a)载体结合的OSA具有高的生物可利用性,(b)从载体结合OSA吸收的硅在泌乳母猪和后代之间通过胎盘或奶或两者的结合传递。
表1:喂给母猪OSA结合的饮食对后代血清硅浓度的影响
母猪的饮食组 | 后代(小猪)血清中硅浓度平均值±SE(ppb) |
规则对照饮食 | 109±8 |
OSA结合的饮食 | 277±20 |
图1在分别补充以下物质之后健康对象中血清中硅浓度从基线值的增加:形式为载体结合OSA的10mg硅,形式为液体OSA的10mg硅,形式为胶体二氧化硅的20mg硅,形式为植物性二氧化硅的20mg硅。
图1
图2在分别补充以下物质之后0-8小时健康对象中测量的血清中硅的总吸收量:形式为载体结合OSA的10mg硅,形式为液体OSA的10mg硅,形式为胶体二氧化硅的20mg硅,形式为植物性二氧化硅的20mg硅。
图2
图3储藏一年期限载体结合OSA对健康对象中血清硅浓度增加的效果。
图3
Claims (15)
1.一种原硅酸的制备方法,其中在非毒性溶剂试剂存在下,在原硅酸的形成下,将可酸水解的硅化合物在酸溶液中水解。
2.权利要求1的方法,其中可酸水解硅化合物是硅酸盐,如单体硅酸盐或水合硅酸盐。
3.权利要求1的方法,其中可酸水解硅化合物具有如下通式:
其中R1,R2,R3和R4独立地选自H、C1-C12烷基、任意地被羟基取代的C1-C12烷氧基,条件是R1,R2,R3和R4不同时为H。
4.权利要求3的方法,其中R1,R2,R3和R4选自H、C1-C4烷基、任意地被羟基取代的C1-C4烷氧基。
5.权利要求1-4的方法,其中溶剂试剂选自:二醇、甘油、(聚)亚烷基二醇、DMSO和聚山梨酸酯80。
6.权利要求1-5的方法,其中溶液包括1-80%,优选10-70%,更优选40-60%溶剂试剂。
7.权利要求1-6的方法,其中溶液是水溶液。
8.权利要求1-7的方法,其中酸溶液的pH为0-4,优选0.2-2.5,更优选0.8-1.0。
9.权利要求1-8的方法,其中将形成的原硅酸与非毒性微粒载体接触。
10.权利要求9的方法,其中在微粒载体存在下原位形成原硅酸。
11.权利要求9或10的方法,其中将载体,在与原硅酸接触之后挤出。
12.权利要求9-11的方法,其中硅制剂的硅含量为0.01-50wt%,优选0.01-10wt%,更优选0.1-10wt%,最优选0.1-5wt%。
13.权利要求9-12的方法,其中硅制剂在8小时内的总硅吸收量大于250(μg)硅h/l,优选大于500(μg)硅h/l,更优选大于600(μg)硅h/l,如250-700(μg)硅h/l,优选300-700(μg)硅h/l。
14.在权利要求1-8中形成的或在权利要求9-13中生产的硅制剂在动物饲料、食品、食品或饲料补充物、和药物或化妆品制剂生产中的用途。
15.可通过权利要求1-8的方法获得的原硅酸。
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DE102015214144A1 (de) * | 2015-07-27 | 2017-02-02 | Beiersdorf Ag | Schweiß verringernde kosmetische Zubereitung |
NL2017436B1 (nl) * | 2015-09-09 | 2017-09-20 | Bio Science B V | Emulsies bevattende siliciumzuur |
WO2019150382A1 (en) * | 2018-01-30 | 2019-08-08 | Privi Life Science Private Limited | A method for preparation of othro silicic acid for agriculture |
PL238905B1 (pl) * | 2018-02-16 | 2021-10-18 | Centrum Badawczo Rozwojowe Glokor Spolka Z Ograniczona Odpowiedzialnoscia | Sposób wytwarzania koncentratu do produkcji napoju prozdrowotnego zawierającego związki krzemu, stosowanego jako enterotransporter lub enterosorbent oraz modułowa instalacja do wytwarzania koncentratu |
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-
1999
- 1999-12-24 EP EP99204496A patent/EP1110909A1/en not_active Withdrawn
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2000
- 2000-12-18 US US10/168,599 patent/US20030099676A1/en not_active Abandoned
- 2000-12-18 ES ES00990794T patent/ES2237492T3/es not_active Expired - Lifetime
- 2000-12-18 AT AT00990794T patent/ATE294137T1/de active
- 2000-12-18 CA CA002394987A patent/CA2394987C/en not_active Expired - Lifetime
- 2000-12-18 CN CNB008182566A patent/CN100368292C/zh not_active Expired - Lifetime
- 2000-12-18 EP EP00990794A patent/EP1242307B1/en not_active Expired - Lifetime
- 2000-12-18 JP JP2001549291A patent/JP4454200B2/ja not_active Expired - Lifetime
- 2000-12-18 CN CN2007103059149A patent/CN101199318B/zh not_active Expired - Lifetime
- 2000-12-18 DE DE60019805T patent/DE60019805T2/de not_active Expired - Lifetime
- 2000-12-18 WO PCT/EP2000/012929 patent/WO2001047807A1/en active IP Right Grant
- 2000-12-18 AU AU30143/01A patent/AU783216B2/en not_active Expired
- 2000-12-18 IL IL15037000A patent/IL150370A0/xx active IP Right Grant
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2002
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- 2009-09-17 US US12/561,812 patent/US20100068294A1/en not_active Abandoned
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102665447A (zh) * | 2009-07-23 | 2012-09-12 | 埃维昂矿泉水有限公司 | 用于制备富含天然原硅酸的水的方法 |
CN102665447B (zh) * | 2009-07-23 | 2014-03-19 | 埃维昂矿泉水有限公司 | 用于制备富含天然原硅酸的水的方法 |
CN102892292A (zh) * | 2010-03-31 | 2013-01-23 | 塔明克公司 | 稳定的生物可利用的可溶的硅酸盐溶液 |
CN104161770A (zh) * | 2013-05-17 | 2014-11-26 | 蒋临沂 | 一种硅酸络合物 |
Also Published As
Publication number | Publication date |
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EP1242307A1 (en) | 2002-09-25 |
JP2003519068A (ja) | 2003-06-17 |
JP4454200B2 (ja) | 2010-04-21 |
IL150370A (en) | 2006-06-11 |
DE60019805T2 (de) | 2006-02-02 |
CN101199318A (zh) | 2008-06-18 |
AU783216B2 (en) | 2005-10-06 |
CN100368292C (zh) | 2008-02-13 |
EP1110909A1 (en) | 2001-06-27 |
AU3014301A (en) | 2001-07-09 |
CA2394987A1 (en) | 2001-07-05 |
US20030099676A1 (en) | 2003-05-29 |
WO2001047807A8 (en) | 2001-07-26 |
ATE294137T1 (de) | 2005-05-15 |
ES2237492T3 (es) | 2005-08-01 |
CN101199318B (zh) | 2012-07-18 |
DE60019805D1 (de) | 2005-06-02 |
US20100068294A1 (en) | 2010-03-18 |
WO2001047807A1 (en) | 2001-07-05 |
CA2394987C (en) | 2009-11-03 |
IL150370A0 (en) | 2002-12-01 |
EP1242307B1 (en) | 2005-04-27 |
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