CN101516412B - 骨水泥及其使用方法 - Google Patents
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Abstract
包含丙烯酸类聚合物混合物的骨水泥,由于丙烯酸类珠的分子量和/或尺寸的分布,所述骨水泥被配制为在较长的窗口具有较高的粘度。
Description
相关申请
根据119(e),本申请要求2006年9月14日提交的60/825,609的优先权,其公开内容通过引用并入本文。
本申请与2006年7月31日提交的名为″Bone Cement and Methods ofUse Thereof″的美国专利申请11/461,072有关,其是2006年2月22日提交的名为″Methods,Materials and Apparatus for Treating Bone and OtherTissue″的美国申请11/360,251的部分继续申请以及是2005年7月31日提交的PCT/IL2005/000812的部分继续申请。这些申请的公开内容通过引用并入本文。
本申请与2006年7月31日提交的名为″Bone Cement and Methods ofUse thereof″的PCT申请PCT/IL2006/052612有关,其公开内容通过引用并入本文。
本申请与2006年3月16日提交的名为″Bone Cement and Methods ofUse thereof″的以色列申请No.174347有关,其公开内容通过引用并入本文。
本申请还与名为″Methods,Materials and Apparatus for TreatingBone and Other Tissue″的一系列美国临时申请有关:2006年2月2日提交的60/765,484;2006年1月26日提交的60/762,789;2005年11月22日提交的60/738,556;2005年10月25日提交的60/729,505;2005年9月28日提交的60/720,725和2005年9月28日提交的60/721,094。这些申请的公开内容也通过引用并入本文。
本申请与以下专利申请相关:2006年2月22日提交的PCT申请PCT/IL2006/000239;2006年1月26日提交的名为″Cannula″的美国临时申请60/763,003;2005年2月22日提交的名为″Materials,devices andmethods for treating bones″的美国临时申请60/654,495;2005年8月1日提交的US 11/194,411;2004年12月28日提交的IL 166017;2004年3月21日提交的IL 160987;2005年1月31日提交的美国临时申请60/654,784;2004年7月30日提交的美国临时申请60/592,149;2004年6月17日提交的PCT申请PCT/IL2004/000527,2004年3月21日提交的以色列申请No.160987,2003年6月17日提交的美国临时申请60/478,841;2003年12月16日提交的美国临时申请60/529,612;2004年1月6日提交的美国临时申请60/534,377和2004年3月18日提交的美国临时申请60/554,558;2001年7月25日提交的美国申请No.09/890,172;2001年7月25日提交的美国申请No.09/890,318和2005年9月14日提交的名为″Hydraulic Device forthe injection of Bone Cement in Percutaneous Vertebroplasty″的美国申请10/549,409。所有这些申请的公开内容都通过引用并入本文。
技术领域
本发明涉及骨水泥(bone cement),其配方和其使用方法。
背景技术
在很多临床情况中,使用水泥(cement)来修补骨头是很普遍的。
例如,老年人中经常发生的椎体(vertebrae)压缩骨折导致疼痛和/或身材变短(或其它变形)。在一种被称为椎体成形术的过程中,水泥被注入骨折的椎体中。椎体成形术能稳定骨折和减少疼痛,尽管它并不能将椎体和人复原至其原有高度。在椎体成形术中,水泥通常被以液相注入,由此注入的阻力不会太大。液态水泥可能会被无意地注射到椎体外面和/或可能通过椎体中的裂缝迁移出去。
在另一种被称为椎体后凸成形术的过程中,通过在椎体内膨胀某种装置如气球(balloon)然后注入固定材料和/或植入物,减轻了骨折。椎体后凸成形术通过允许使用更低的压力来注入水泥而减少了水泥渗漏的问题。
通常,由于聚合物链通过直接与单体的双键反应而生长,聚合物水泥变得更加粘稠(viscous)。聚合通过″加成机理″开始,其中单体通过与引发剂-最常见地为自由基(含单个未成对电子的分子)的不稳定分子(volatile molecule)-反应而变得不稳定。自由基与单体键合,形成可攻击下一个单体的双键的单体自由基以增长聚合物链。由于自由基非常短暂,所以往往以在溶液中稳定的惰性过氧化物的形式添加引发剂。当热或光分裂所述过氧化物分子时,形成自由基。对于其中使用高温并不现实的应用(比如骨水泥在体内的使用),通常通过添加化学活化剂如N,N-二甲基对甲苯胺来分裂过氧化物(Nussbaum DA等:″TheChemistry of Acrylic Bone Cement and Implication for Clinical Use inImage-guided Therapy″,J Vase Interv Radiol(2004);15:121-126;其内容通过引用完全并入本文)。
可商购的粘稠骨水泥的例子包括但不限于CMWNos.1,2和3(DePuy Orthopaedics Inc.;Warsaw,IN,USA)以及SimplexTM-P和-RO(Stryker Orthopaedics;Mahwah,NJ,USA)。这些水泥以在混合之后和达到500帕-秒的粘度之前的液相为特征。在一个典型的应用情形中,这些已有的水泥在处于液相时被倾倒入递送装置中。
也曾尝试通过,例如在面团期(doughing time)和聚合反应开始期间,注入更粘稠的水泥来减少水泥渗漏。但是,粘稠物质,比如硬化PMMA,通常在它们一达到高粘度就非常快地变硬。在矫形过程(orthopedic procedures)中这通常妨碍粘稠物质的注入。
某些骨修补材料(fixing materials),如聚甲基丙烯酸甲酯(PMMA),在凝固时会发热且可能放出有毒物质。
美国专利和公布4,969,888、5,108,404、6,383,188、2003/0109883、2002/0068974、6,348,055、6,383,190、4,494,535、4,653,489和4,653,487记述了处理骨头的各种工具和方法,其公开内容通过引用并入本文。
美国专利公开2004/0260303教导了一种向椎体中递送骨水泥的设备,其公开内容通过引用并入本文。
Pascual,B.等人在″New Aspects of the Effect of Size and SizeDistribution on the Setting Parameters and Mechanical Properties ofAcrylic Bone Cements,″Biomaterials,17(5):509-516(1996)中考虑了PMMA珠的尺寸对水泥凝固参数的影响。此文章通过引用完全并入本文。
Hernandez等人在(2005)″Influence of Powder Particle SizeDistribution on Complex Viscosity and Other Properties of Acrylic BoneCement for Vertebroplasty and Kyphoplasty″Wiley International ScienceD01:10:1002/jbm.b.30409(98-103页)中考虑了PMMA珠的尺寸分布对水泥凝固参数的影响。Hernandez提出有利地是使用液相来配置水泥以有利于注入。此文章通过引用完全并入本文。
Arroyo的US 5,276,070公开了在骨水泥的配制中使用分子量在0.5-1.5百万道尔顿范围内的丙烯酸类聚合物。此专利的公开内容通过引用完全并入本文。
Cooke的US 5,336,699公开了在骨水泥的配制中使用分子量为约10万道尔顿的丙烯酸类聚合物(acrylic polymers)。此专利的公开内容通过引用完全并入本文。
发明内容
本发明的一个主要方面涉及一种骨水泥,所述骨水泥的特征在于当液态单体和粉末状聚合物组分被混合在一起时以基本上无中间液相的方式从分离的液体单体和粉末状聚合物组分向以高粘度为特征的单相的快速转变。任选地,高粘度是指500帕-秒(Pascal-second)或更高。当95-100%的聚合物珠被单体润湿时,混合被认为完成。在本发明的一个示例实施方案中,混合在60秒之内、任选地45秒之内、任选地30秒之内完成。
在本发明的一个示例实施方案中,所述水泥的特征在于在所述水泥硬化之前的数分钟的工作窗口,在所述工作窗口期间粘度保持很高。任选地,在所述工作窗口期间粘度的变化不会达到显著影响注入参数的程度。在本发明的一个示例实施方案中,在所述工作窗口期间,在至少2分钟的子窗口期间粘度升高小于10%。任选地,在所述工作窗口中粘度不超过500、任选地1000、任选地1500、任选地2000帕-秒,或更小或更大或中间的值。在本发明的一个示例实施方案中,所述工作窗口持续6、任选地8、任选地10、任选地15分钟,或更短或更长或中间的时间。任选地,环境温度影响所述工作窗口的持续时间。在本发明的一个示例实施方案中,所述水泥可被冷却或加热以影响所述工作窗口的长度。
本发明的一些实施方案的一个方面涉及骨水泥的配方(formulations),其基于两种、任选地三种或更多种与液体单体混合的聚合物珠的子群(sub-populations)。
根据本发明的示例实施方案,子群的特征可以为平均分子量(MW)和/或物理尺寸(physical size)和/或几何形状,和/或密度。在本发明的一个示例实施方案中,独立地限定了基于尺寸和基于MW的子群。在本发明的一个示例实施方案中,选择所述子群以产生期望的粘度特性和/或聚合反应动力学(polymerization kinetics)。任选地,所述聚合物珠包括聚甲基丙烯酸甲酯(PMMA)和/或PMMA苯乙烯共聚物。任选地,与甲基丙烯酸甲酯(MMA)单体一起使用PMMA。
任选地,高分子量的子群有助于基本上没有液相地快速转变到高粘度。任选地,低分子量的子群有助于更长的工作窗口。
任选地,小尺寸的子群有助于用单体溶液快速润湿聚合物珠。在本发明的一个示例实施方案中,快速润湿有利于基本上没有液相地直接转变到粘稠水泥。
在一些情况下,小百分比的珠可能不属于任何相关子群。所述小百分比可以为例如1%、1.5%、2%、3%、4%、5%,或更少或中间或更大的百分比。
在本发明的一个示例实施方案中,存在特征为分子量的至少两个PMMA聚合物珠的子群。例如,占所有PMMA珠的95-97%(w/w)的第一子群的特征可以是270,000-300,000道尔顿的平均MW;第二子群(2-3%w/w)的特征可以是3,500,000-4,000,000道尔顿的平均MW;而第三子群(0-3%w/w)的特征可以是10,000-15,000道尔顿的平均MW。
在本发明的一个示例实施方案中,聚合物珠的特征在于每单位重量的高表面积。任选地,所述珠的表面积为0.5-1、任选地0.5-0.8、任选地约0.66m2/g,或中间或更小或更大的值。任选地,所述高表面积/重量比,例如通过有助于聚合物单体接触,改善润湿性能和/或缩短聚合时间。
在本发明的一个示例实施方案中,以向高粘度的瞬时转变(immediate transition)为特征的水泥在椎体成形术或椎体后凸成形术过程中在工作窗口期间被注入。任选地,注入是在足够的压力下进行的以移动骨折的骨头,如坍塌椎体的椎板。任选地,在高压下注入粘稠水泥有助于骨折减少和/或椎体高度的恢复。
在本发明的一个示例实施方案中,所述材料(例如,骨水泥)包括经过处理的骨(processed bone)(人或动物来源)和/或人造骨(syntheticbone)。任选地,所述水泥具有骨传导性(osteoconductive)和/或骨诱导性(osteoinductive)行为。可以任选地添加通常用于骨水泥预备的其它添加剂。这些添加剂包括但不限于硫酸钡和过氧化苯甲酰。
根据本发明的某些实施方案,工作窗口长度由瞬时作用(immediateeffect)与延迟作用(late effect)之间的相互作用决定。在本发明的一个示例实施方案中,所述瞬时作用包括MMA溶剂化作用和/或PMMA聚合物珠的包封(encapsulation)。所述瞬时作用有助于源于溶剂化作用和/或珠之间的摩擦的初始混合物的高粘度。所述延迟作用随着珠溶解和聚合反应的进行而提高平均聚合物MW。此增加的平均聚合物MW在整个工作窗口期间都将粘度保持在很高。
在本发明的一个示例实施方案中,使用了一组粘度参数来调节水泥配方以产生以期望粘度下的期望工作窗口为特征的水泥。
在本发明的一个示例实施方案中,提供了一种包含丙烯酸类聚合物混合物的骨水泥,该水泥的特征在于在单体组分与聚合物组分的混合开始之后在180秒之内其达到至少500帕-秒的粘度,且特征在于足以容许体内使用(in-vivo use)的生物相容性。
任选地,在所述初始阶段(initial period)之后对于至少5分钟的工作窗口,混合物的粘度保持在500-2000帕-秒之间。
任选地,所述工作窗口为至少8分钟长。
任选地,所述混合物包括PMMA。
任选地,所述混合物包括硫酸钡。
任选地,所述PMMA以PMMA/苯乙烯共聚物的形式提供。
任选地,所述PMMA以分成至少两个子群的珠群(a population ofbeads)的形式提供,各个子群的特征在于平均分子量。
任选地,PMMA珠的最大的子群的特征在于150,000道尔顿-300,000道尔顿的MW。
任选地,PMMA珠的最大的子群占所述珠的90-98%(w/w)。
任选地,PMMA珠的高分子量的子群的特征在于至少3,000,000道尔顿的平均MW。
任选地,PMMA珠的高分子量的子群占所述珠的2-3%(w/w)。
任选地,PMMA珠的低分子量的子群的特征在于小于15,000道尔顿的平均MW。
任选地,PMMA珠的低分子量的子群占所述珠的0.75-1.5%(w/w)。
任选地,PMMA以分成至少两个子群的珠群的形式提供,各个子群的特征在于平均珠直径。
任选地,特征在于平均直径的至少一个珠子群被进一步分成至少两个亚-子群(sub-sub-population),各个亚-子群的特征在于平均分子量。
任选地,PMMA以分成至少三个子群的珠群的形式提供,各个子群的特征在于平均珠直径。
任选地,所述水泥进一步包括经过处理的骨和/或人造骨。
任选地,所述水泥的特征在于当100%的聚合物组分被单体组分润湿时,该水泥达到至少500帕-秒的粘度。
任选地,粘度为至少800帕-秒。
任选地,粘度为至少1500帕-秒。
任选地,在2分钟之内达到所述粘度。
任选地,在1分钟之内达到所述粘度。
任选地,在45秒之内达到所述粘度。
在本发明的一个示例实施方案中,提供了一种骨水泥,其包括:
聚合物组分;和
单体组分,
其中使所述聚合物组分与所述单体组分接触产生混合物,该混合物从混合开始在1分钟之内达到大于200帕-秒的粘度并且从混合开始至少6分钟都保持低于2000帕-秒。
任选地,所述聚合物组分包括丙烯酸类聚合物。
在本发明的一个示例实施方案中,提供一种为制备骨水泥而配制的微粒混合物,所述混合物包括:
(a)60-80%的聚合物珠,其包含特征在于150,000道尔顿-300,000道尔顿的MW的主子群和特征在于3,000,000道尔顿-4,000,000道尔顿的MW的高分子量子群;和
(b)20-40%的对于X射线不透明的材料。
任选地,所述聚合物珠包括特征在于10,000道尔顿-15,000道尔顿的MW的第三子群。
在本发明的一个示例实施方案中,提供了一种制造聚合物骨水泥的方法,所述方法包括:
(a)定义粘度变化图(viscosity profile),其包括向以高粘度为特征的工作窗口的快速转变;
(b)选择聚合物组分和单体组分以制造符合所述粘度变化图的水泥;和
(c)混合所述聚合物组分和单体组分以产生符合所述粘度变化图的水泥。
在本发明的一个示例实施方案中,提供了一种水泥试剂盒(cementkit),包括:
(a)包括单体的液体组分;和
(b)包括聚合物珠的粉末组分,
特征在于所述粉末组分以所述聚合物珠的分子量和粉末颗粒的尺寸中至少之一为基本上非正态分布的形式提供,从而由所述试剂盒混合而来的水泥与具有基本上正态分布的水泥相比既具有增大的瞬时粘度又具有增大的工作窗口。
任选地,所述基本上非正态分布为偏斜分布(skewed distribution)。
任选地,所述基本上非正态分布包括包含更高分子量的珠的较小的组分。任选地,所述组分的平均分子量为所述聚合物珠的平均分子量的至少2倍。任选地,所述倍数为至少3或为至少5。
任选地,所述基本上非正态分布包括包含更小尺寸颗粒的较小的组分。
附图说明
将参照实施方案的以下描述并结合附图对本发明的示例性非限制实施方案进行说明。在一个以上附图中出现的相同结构、要素或部件通常在其出现的所有附图中都以相同或相似的数字标记,其中:
图1是说明本发明示例性水泥的制备和行为的示例性方法100的流程图;
图2是粘度变化图,其描述了本发明示例性水泥和现有技术示例性水泥的粘度(帕-秒)随时间(分钟)的变化;
图3和4是对于本发明的示例性水泥,在限定的条件下,作为每单位位移(mm)的施加力牛顿显示粘度的图,并显示既早且长的注入时间窗口;和
图5是对于根据本发明的一个示例实施方案的珠配方,显示珠尺寸分布分析结果的图。
示例性实施方案之详细说明
示例性骨水泥制备之概述
图1是显示根据本发明某些实施方案的示例性水泥的制备和行为的流程图。
在本发明的一个示例实施方案中,骨水泥的液体单体和粉末状聚合物组分被合并110。任选地,液体单体被倾倒在粉末状聚合物上。
根据本发明的不同实施方案,平均聚合物分子量和/或聚合物分子量分布和/或聚合物珠尺寸被精确控制以影响聚合反应动力学和/或水泥粘度。做为选择或另外,聚合物和/或单体组分可以包含不直接涉及所述聚合反应的成分。
在本发明的一个示例实施方案中,聚合物(例如丙烯酸类聚合物,如PMMA)珠被分成两个或更多子群。任选地,所述子群以分子量(MW)来限定。在本发明的一个示例实施方案中,在所有珠中丙烯酸类聚合物的平均分子量在约300,000-400,000道尔顿的范围内,任选地约373,000道尔顿。对于制造具有期望的聚合剖面图(polymerization profile)的水泥的一批珠,所有珠的该平均MW通过实验确定。
任选地,所述聚合物珠作为丙烯酸类聚合物混合物,例如包含硫酸钡的混合物,的一部分提供。
在112,将所述组分混合直至所述聚合物被所述单体润湿。任选地,当润湿为95-100%完成时,混合物已经达到期望的高粘度,例如500帕-秒或更高。任选地,混合112在1、5、10、15、30、60、90、120或180秒之内完成。在现代医疗机构中,缩短所述混合时间是有利的,以减少对物理设施和/或医务人员的要求。相对于现有可选选择,节约甚至1-2分钟也是很有意义的。在本发明的一个示例实施方案中,混合112是在共同未决申请US 11/428,908中描述的类型的混合设备中进行的,该申请的公开内容通过引用完全并入本文。
在混合112完成之后,出现工作窗口114,在该工作窗口期间水泥保持粘稠但尚未完全硬化。根据本发明的不同示例实施方案,工作窗口114可以为约2、5、8、10、15或20分钟,或中间的或更长的时间。所述工作窗口的持续时间可以随具体的水泥配方和/或环境条件(例如温度和/或湿度)而变化。配方考虑的事项包括但不限于聚合物MW(平均和/或分布)、聚合物珠尺寸、非聚合成分的浓度和聚合物:单体比。
工作窗口114使得开业医生(medical practitioner)拥有足够的时间来装载高压注入装置和将水泥注入120到所需位置中。任选地,在混合112之前或与混合112同时将注入针管或插管(cannula)插入体内,由此窗口114只需长到足够进行装载和注入120。示例注入系统公开于2006年2月22日提交的名为″Methods,materials,and apparatus for treating bone andother tissue″的共同未决申请US 11/360,251中,其公开内容通过引用完全并入本文。
在本发明的一个示例实施方案中,到达硬化状态的硬化116在工作窗口114之后出现。所述水泥即使没有被注入也会发生硬化116。
就相关医疗过程而论的优点
在本发明的一个示例实施方案中,具有如上所述粘度变化图的水泥可用于椎体修复(vertebral repair),例如用在椎体成形术和/或椎体后凸成形术过程中。
任选地,在注入时粘稠的水泥的使用降低材料渗漏和/或渗透到脊柱内的松质骨中(交错连接(interdigitaion))的危险和/或减少骨折[参见GBaroud等人,Injection biomechanics of bone cements used invertebroplasty,Bio-Medical Materials and Engineering 00(2004)1-18]。减少的渗漏任选地有助于增加的积极临床结果可能性。
在本发明的一个示例实施方案中,在注入开始时,任选地在混合112开始之后3、2或1分钟或更少的或中间的时间,骨水泥的粘度为500、任选地1000、任选地1500、任选地2000帕-秒,或更小或更大或中间的值。任选地,所述粘度在工作窗口114期间不超过2000帕-秒。在本发明的一个示例实施方案中,一旦95-100%的所述聚合物珠被单体润湿就基本上达到此粘度。
如上所述以高粘度为特征的水泥任选地可以手工操作。
在本发明的一个示例实施方案中,水泥足够粘稠以在其被注入时移动周围的组织。任选地,周围组织的移动有助于骨折减少和/或椎骨高度的恢复。
水泥的注入体积可根据所执行的矫形过程的类型和/或数量而变化。对于典型的椎体修复来说注入体积可以为,例如,2-5cc,对于其它类型骨头的修复注入体积可以高达8-12cc或更高。根据例如空间的容积和期望的注入效果,其它体积也可能是合适的。在有些情况下,大体积的粘稠水泥被装入递送装置中且在单个医疗过程中数个椎体被修复。任选地,使用一个或更多个插管或针管来实施多个过程。
根据本发明的示例实施方案的粘稠水泥可以通过施加足够的压力在期望流速下通过标准的矫形插管被输送。示例性的平均注入速度可以在0.01-0.5ml/sec的范围内,任选地约0.05、约0.075或0.1ml/sec,或更小或中间或更大的平均流速。任选地,在注入期间流速变化很大(例如,脉冲注入)。任选地,手动或使用电子或机械线路来控制所述流速。在本发明的一个示例实施方案中,在注入所述水泥时医务人员对其进行观察(例如通过透视法(fluoroscopy))并基于观察结果调节流速和/或递送体积。任选地,调节和/或控制所述流速以允许开业医生基于在所述过程期间获得的医学图像(例如透视法)来评估所述过程的进展。在本发明的一个示例实施方案中,所述水泥足够粘稠,当施加高于阈值的压力时其前进进入体内并当压力被降低到低于阈值时停止前进。任选地,所述阈值随水泥粘度、插管直径和插管长度中的一个或多个的变化而变化。
本发明一些实施方案的示例性配方与已有配方的比较
尽管PMMA已被广泛用于骨水泥的制备,但已有的PMMA基水泥通常都以组分混合之后持久的液态(persistent liquid state)为特征。
呈鲜明对比的是,本发明的某些示例实施方案的水泥以基本上没有液态为特征。任选地,从分离的聚合物和单体组分向高度粘稠状态的直接转变来源于聚合物珠的两个或更多个子群的存在。
作为基于珠子群的配方的结果,根据本发明的一个示例实施方案的水泥的粘度变化图明显不同于具有相似平均分子量的现有聚合物基水泥(例如PMMA)的粘度变化图。
由于现有PMMA水泥的粘度变化图通常以从高粘度到完全硬化的快速转变为特征,所以这些水泥通常以液相被注入骨中从而它们不会在注入过程中硬化。
呈鲜明对比的是,根据本发明的示例性水泥在其硬化之前在长工作窗口114期间保持高度粘稠。该长工作窗口使得可以进行持续数分钟的医疗过程和给所述过程带来高粘度材料的优点。
应当注意,尽管描述了具体的实例,但经常存在改变配方以达到特定的期望机械性能的情形。例如,不同的诊断可能建议不同的材料粘度,这接着可能导致MW(平均和/或分布)、珠尺寸和珠表面积中的一个或多个的调整。
在本发明的一个示例实施方案中,所述水泥被混合112并在体外达到高粘度。任选地,所述材料在真空或通风条件下混合。以这种方式,某些具有可能危险的副产物的材料可被安全地混合然后用于体内。
在本发明的一个示例实施方案中,配制水泥从而其机械性能与其将注入/植入其中的骨头相匹配。在本发明的一个示例实施方案中,配制水泥以与健康的或骨质疏松的骨小梁(osteoporotic trabecularbone)(松质骨)机械地相匹配。任选地,在进入过程中(during access)测量所述骨的机械性能,例如,基于前进的阻力或使用通过插管提供的传感器或通过取样,或基于x射线密度测定法测量。在本发明的一个示例实施方案中,水泥的强度随以下中的一个或多个的变化而变化:高MW子群的尺寸和/或珠尺寸与珠MW之间的关系。
通常,PMMA比骨小梁强度更大并具有更高的杨氏模量。例如,健康的骨小梁强度可在1.5-8.0兆帕之间,杨氏模量为60-500兆帕。例如,皮质骨(cortical bone)的强度值为65-160兆帕,杨氏模量为12-40千兆帕(giga Pascal)。PMMA典型地具有约皮质骨一半的值(70-120兆帕强度)。
图2是对于本发明的一种示例性骨水泥,粘度随时间变化的图。该图并非按比例描绘,只是提供用于说明本发明示例实施方案的原理。混合过程的结束标为时间0。当95-100%的丙烯酸类聚合物珠已经用单体润湿时,混合被认为结束。该图显示了一种一旦混合就进入高粘度塑化相从而基本上没有液相的示例性骨水泥。
图2表明一旦达到高粘度,该粘度就保持相对稳定2、任选地5、任选地8分钟或更长。在本发明的一个示例实施方案中,这段粘度稳定的时间间隔提供了用于进行医疗过程的工作窗口114(在此表示为Δt1)。在本发明的一个示例实施方案中,稳定的粘度是指在混合完成之后在至少2分钟、任选地至少4分钟的窗口期间水泥的粘度变化小于200帕-秒。任选地,所述窗口在混合开始1、2、3、4或5分钟或更短的或中间的时间之后开始。在本发明的一个示例实施方案中,从混合开始至少4、任选地至少6、任选地至少8、任选地至少10分钟或中间的或更长的时间,水泥的粘度保持低于1500、任选地2000帕-秒。
为了比较,该图显示示例性的现有技术水泥在混合之后大约10.5分钟的时间达到可与本发明示例性水泥在时间0所达到的粘度相比的粘度,并且到约15.5分钟(Δt2)就完全凝固。
对于根据本发明的某些实施方案的示例性水泥来说,期间粘度在400-2000帕-秒之间的工作窗口114(Δt1)与示例性现在技术水泥的相当的窗口(Δt2)相比既长又早。任选地,(Δt1)基本从混合一完成就开始。
示例水泥配方
根据本发明的不同示例实施方案,粉末状聚合物组分与液体单体组分之间比例的变化会影响工作窗口114的持续时间和/或在所述窗口期间水泥的粘度。任选地,调节这些比例以实现期望的结果。
在本发明的一个示例实施方案中,所述粉末状聚合物组分含有PMMA(69.3%w/w);硫酸钡(30.07%w/w)和过氧化苯甲酰(0.54%w/w)。
在本发明的一个示例实施方案中,所述液体单体组分含有MMA(98.5%v/v);N,N-二甲基对甲苯胺(DMPT)(1.5%v/v)和氢醌(20ppm)。
在本发明的第一示例实施方案中,20±0.3克聚合物粉末和9±0.3克的液体单体被合并(重量比为约2.2∶1)。
在本发明的第二示例实施方案中,20±0.3克聚合物粉末和8±0.3克液体被合并(重量比为2.5∶1)。
在与第二示例实施方案相同的重量比(2.5∶1)下,第三示例实施方案可以包括合并22.5±0.3克聚合物粉末和9±0.3克液体。
通常,提高聚合物对单体的重量比将产生在更少时间内达到更高粘度的水泥。但是,存在一个极限,超过该极限之后将没有足够的单体来润湿所有聚合物珠。
任选地,所述粉末状聚合物组分的组成可以变化,并且包含PMMA(67-77%、任选地67.5-71.5%w/w);硫酸钡(25-35%、任选地28-32%w/w)和过氧化苯甲酰(0.4-0.6%w/w)并仍然与上述粉末组分配方的表现基本相同。
任选地所述液体单体组分的组成可以变化,并且包含氢醌(1-30ppm、任选地20-25ppm)并仍与上述液体组分配方的表现基本相同。
示例性水泥随时间的粘度测量
为了评价根据本发明的某些实施方案的不同示例性水泥批次的粘度变化图,将一块(a bulk of)预混合的骨水泥放置在不锈钢注射器体之内。Krause等人描述了一种根据施加的力计算粘度的方法。(″Theviscosity of acrylic bone cements″,Journal of Biomedical MaterialsResearch,(1982):16:219-243)。此文章通过引用完全并入本文。
在该实验设备中,所述注射器体的内径为约18mm。远端圆筒形出口的内径为约3mm且长度超过4mm。此构造模拟针对标准骨水泥递送套管/骨进入针管(bone access needle)的连接器(connection)。活塞施加力(F),由此使骨水泥流过所述出口。活塞设置为以约3mm/min的恒定速度移动。因此,活塞偏移(deflection)可表示经过的时间。
所述实验过程充当一种毛细管挤出流变仪。所述流变仪测量毛细管端到端的压差。所述装置由18mm的圆柱形贮器和活塞组成。所述贮器的远端由4mm长直径为3mm的洞构成。该过程采用小直径针管和高压。假设稳定流动、等温条件和被测试材料的不可压缩性,阻碍毛细管中流体运动的粘滞力等于作用在活塞上的施加力,其通过测力传感器(load cell)和摩擦来测量。结果以力对位移(displacement)的形式给出。由于位移速率是恒定的并被设为3mm/min,所以剪切速率也是恒定的。为了测量从测试开始后过去的时间,所述位移速率被除以3(慢进速度(jog speed))。
图3示出以力(牛顿)对位移(mm)表示的本发明第一示例水泥批次的粘度变化图。用于此实验的水泥如上面在″示例水泥配方″中所述包括液体组分和粉末组分。
在该测试(平均温度:22.3℃;相对湿度:约48%)中,水泥被混合30-60秒,然后手动操作和放置在注射器之内。在混合结束之后约150秒,通过活塞施加力,测量力和活塞偏移。
在混合之后2.5分钟时(0mm偏移),所施加的力大于30N。
在混合之后6.5分钟时(12mm偏移),所施加的力为约150N。
在混合之后7.5分钟时(15mm偏移),所施加的力大于200N。
在混合之后8.5分钟时(18mm偏移),所施加的力大于500N。
在混合之后9.17分钟时(20mm偏移),所施加的力大于1300N。
图4示出以力(牛顿)对位移(mm)表示的本发明另外的示例水泥批次的粘度变化图。此测试中的水泥是按照与图3的实验所述相同的配方制备的。在此测试(平均温度:21.1℃;相对湿度:约43%)中,水泥被混合约45秒,然后手动操作和放置在注射器之内。在混合结束之后约150秒,通过活塞施加力,测量力和活塞偏移。
在混合之后2.25分钟时(0mm偏移),所施加的力大于30N。
在混合之后8.25分钟时(18mm偏移),所施加的力为约90N。
在混合之后10.3分钟时(25mm偏移),所施加的力大于150N。
在混合之后11.4分钟时(28.5mm偏移),所施加的力大于500N。
在混合之后12.25分钟时(30mm偏移),所施加的力大于800N。
图3和4中显示的以及在上文中概括的结果说明,根据本发明的一些实施方案的示例骨水泥在混合完成之后的2.25分钟或更少的时间之内达到高粘度。做为选择或另外,这些水泥以短混合时间为特征(即在30-60秒内转变到高度粘稠的塑化相)。所述示例水泥提供了4.5-6.3分钟、任选地如果施加更大的压力和/或环境温度更低则更长的用于注入的″工作窗口″。这些时间各自相应于14.9和20.8ml的递送体积(单个椎体的椎体成形术一般需要约5ml的水泥)。这些体积对大多数椎体修复过程来说都是足够的。这些结果与图2中描述的期望特征相符合。两个实验之间的差异可以反映温度和湿度对反应动力学的影响。
分子量分布
在本发明的一个示例实施方案中,平均分子量(MW)通过一个或多个分子量明显不同于聚合物珠主子群的珠的小子群的存在而被偏斜(skewed)。所述一个或多个珠的小子群的MW可显著大于和/或显著小于平均MW。
在本发明的一个示例实施方案中,MW显著高于平均MW的甚至是较小的聚合物珠的子群的存在也会导致水泥在用单体溶液润湿聚合物珠之后在短时间内就达到高粘度。任选地,增大所述高MW子群的尺寸提高了所达到的粘度。做为选择或另外,增大所述高MW子群的平均MW提高了所达到的粘度和/或减少了达到高粘度的时间。
任选地,在配方中提供所述一个或多个小的珠的子群,其中所有珠中PMMA的平均分子量为80,000、任选地100,000、任选地120,000、任选地140,000、任选地160,000、任选地180,000、任选地250,000、任选地325,000、任选地375,000、任选地400,000、任选地500,000道尔顿,或中间的或更小的或更大的值。
在本发明的另一个示例实施方案中,所述珠中的丙烯酸类聚合物的平均分子量在约130,000-170,000道尔顿的范围内,任选地为约160,000道尔顿。
在本发明的一个示例实施方案中,PMMA珠主子群的MW为约150,000道尔顿到约500,000道尔顿,任选地约250,000道尔顿到约300,000道尔顿,任选地约275,000道尔顿到约280,000道尔顿。任选地,约90-98%[w/w]、任选地约93%-98%、任选地约95%-97%的珠属于所述主子群。
在本发明的一个示例实施方案中,PMMA珠的第二高MW子群的MW为约600,000道尔顿到约5,000,000道尔顿,任选地约3,000,000道尔顿到约4,000,000道尔顿,任选地约3,500,000道尔顿到约3,900,000道尔顿。任选地,约0.25%-5%[w/w]、任选地约1%-4%、任选地约2%-3%的珠属于此高MW子群。任选地,此高分子量子群包括苯乙烯共聚物。在本发明的一个示例实施方案中,在该珠的子群中更高的分子量有助于在用单体溶液润湿聚合物珠的2分钟之内、任选地1分钟之内、任选地0.5分钟或更短的时间之内达到高粘度。
在本发明的一个示例实施方案中,PMMA珠的第三低MW子群的MW为约1,000道尔顿到约75,000道尔顿,任选地约10,000道尔顿到约15,000道尔顿,任选地约11,000道尔顿到约13,000道尔顿。任选地,约0.5-2.0%[w/w]、任选地约1%的珠属于该子群。
任选地,所述MW子群彼此不同。这可导致子群之间关于一个或多个参数的缺口。在本发明的一个示例实施方案中,所述子群在色谱分离方法中作为独立的峰呈现。任选地,所述峰通过向基线的回归被分隔。根据检测的灵敏度,可以存在背景噪声水平。任选地,相对于所述噪声水平测量缺口。
任选地,所述子群彼此邻接从而没有明显的缺口。在本发明的一个示例实施方案中,所述子群在色谱分离方法中作为重叠峰呈现。在这种情况下,所述峰之间不存在向基线的回归。
示例水泥批次的实验分析
使用本领域已知的色谱技术识别和量化以平均分子量为特征的子群。此处所述的示例结果是基于GPC分析。GPC分析中的每个峰都被认为是一个子群。使用HPLC可以进行类似的分析。结果汇总在表I中。
表I:根据上文″示例水泥配方″中所述粉末状聚合物组分的骨水泥的基于GPC分析的聚合物珠的MW分布。
级分 | 占总数的% | PDI1 | Mw2 | Mn3 |
1 | 96.5 | 1.957 | 278,986 | 142,547 |
2 | 2.5 | 1.048 | 3,781,414 | 3,608,941 |
3 | 1.0 | 1.009 | 12,357 | 12,245 |
100.0 | 2.955 | 373,046 | 126,248 |
1多分散指数(PDI),是给定聚合物样品中分子量分布的量度,等于Mw/Mn。
2Mw为以道尔顿计的重均分子量
3Mn为以道尔顿计的数均分子量
表I显示了具有丙烯酸类聚合物珠的三个子群的本发明的示例实施方案。
PMMA珠主子群(级分1)的分子量(MW)为278986道尔顿。约96.5%的珠属于此子群。
PMMA珠第二子群(级分2)的MW为3781414道尔顿。约2.5%的珠属于此子群。
PMMA珠第三子群(级分3)的MW为12357道尔顿。约1%的珠属于此子群。
在本发明的一个示例实施方案中,包括这三个子群的水泥的特征在于:短混合时间和/或从混合开始在0.5-3分钟、任选地0.5-1.5分钟内达到500-900帕-秒的粘度和/或在混合之后其保持低于2000帕-秒至少6-10分钟。在手术室可获得性和医务人员稀缺的情况下,在矫形过程中短混合时间继之以长工作窗口被认为是有利的。
尺寸分布
在本发明的一个示例实施方案中,骨水泥的特征在于具有包括至少两个聚合物珠的子群的尺寸分布的珠。
在本发明的一个示例实施方案中,聚合物珠直径在10-250微米的范围内,平均值为约25、30、40、50、60微米,或更低的或更高的或中间的直径。在本发明的一个示例实施方案中,珠的子群通过它们的尺寸限定。
任选地,聚合物(例如PMMA)珠主子群的特征为约20-约150、任选地约25-约35微米的直径,任选地平均为约30微米。此主子群中的珠任选地远小于Hernandez等人(2005;如上面所引用)使用的最小的珠。小珠的存在可有助于在用单体润湿之后粘度的快速增大。
任选地,大聚合物珠的第二子群的特征在于约150微米或更大的直径。大珠的存在可减慢聚合反应和防止硬化,有助于长工作窗口。
任选地,剩余珠的特征在于非常小的平均直径,例如小于20微米、任选地小于15微米、任选地为约10微米或更小。非常小的珠的存在可以在混合期间促进使用单体液体的快速润湿和有助于基本上没有液相地向粘稠状态的快速转变。
显微分析表明所述珠一般是球状或椭球状的。
Hernandez等人(2005;如上面所引用)研究了通过将平均尺寸为118.4μ(Colacry)和69.7μ(Plexigum)的两类珠以不同比例结合在一起来调节平均聚合物珠尺寸的可能性。但是,Hernandez的目的在于″足够液态以被注入″的配方。Hernandez记述的所有配方都以在约2分钟或更短时间内(相应于窗口114)粘度从500帕-秒增大到2000帕-秒为特征。Hernandez没有暗示或建议存在增大此窗口的大小的任何必要或优点。
显微分析还表明硫酸钡颗粒作为长度为约1微米的细长无定形块(masses)存在。在某些情况下观察到大小高达70微米的聚集体(aggregates)。在某些情况下,硫酸钡颗粒和聚合物珠聚集在一起。任选地,硫酸钡与聚合物珠的聚集体可以延迟单体对聚合物珠的润湿。
在本发明的一个示例实施方案中,MMA溶剂化(solvate)和/或包封(encapsulate)所述PMMA聚合物珠,且由于所述溶剂化作用和/或珠之间的摩擦起始混合物的粘度很高。随着珠的溶解,由于增大了平均聚合物MW的聚合反应,所以粘度仍保持很高。
下表II显示了示例颗粒尺寸分布,例如适合于表I所示水泥,基于对0.375-2000微米范围内的颗粒的分析:
表II:示例粉末状组分的颗粒尺寸分布
Vol.% | 10 | 25 | 50 | 75 | 90 |
最大珠直径[微米] | 2.3 | 25.75 | 45.07 | 60.68 | 76.34 |
第二示例水泥批次的实验分析
混合物水泥试剂盒的另一个实例包括液体和粉末,其包括大量丙烯酸类聚合物珠。此水泥试剂盒按如下配制:
(a)液体(9.2gr)
(i)甲基丙烯酸甲酯(MMA)98.5%(vol)
(ii)N,N-二甲基对甲苯胺1.5%(vol)
(iii)氢醌20ppm(vol)
(b)粉末(20gr)
(i)聚甲基丙烯酸甲酯(PMMA)69.39%(重量)
(ii)硫酸钡30.07%(重量)
(iii)过氧化苯甲酰0.54%(重量)
如上所述,在其它配方中所述数量可以变化,例如,以达到特定的机械(或其它)性能,或者它们可以变化并获得相同的机械性能。在另一变体中,可以向所述粉末和/或液体相中加入药物。也可使用其它液体相,如本领域中对于PMMA类水泥已知的那样。例如,如上所述,所述比例可以变化。
表III汇总了此示例水泥的丙烯酸类珠组分的分子量分布。假定的是,用分子量更重的组分提供非正态的分子量分布(例如通过包含分子量较高的珠来偏斜MW分布),提供提高的瞬时粘度。在本发明的一个示例实施方案中,所述更高MW的珠的量较少(例如,小于20%、小于10%、小于5%)并且MW为500,000-2,000,000道尔顿、任选地600,000-1,200,000道尔顿(例如,如下表所示)。
表III:第二示例批次骨水泥的聚合物珠的MW分布
分子量范围[道尔顿] | 占总数的% |
1,000,000-2,000,000 | 0.38% |
500,000-1,000,000 | 3.6% |
250,000-500,000 | 12.4% |
100,000-250,000 | 36.4% |
50,000-100,000 | 26.6% |
25,000-50,000 | 14.2% |
10,000-25,000 | 5.3% |
8,000-10,000 | 0.5% |
5,000-8,000 | 0.4% |
在本发明的一个示例实施方案中,骨水泥以具有包括不同材料的至少两个子群的尺寸分布的珠为特征。任选地,至少两个子群包括聚合物(例如PMMA)珠和硫酸钡颗粒。任选地,硫酸钡的粒径范围为0.01-15微米、任选地0.3-3微米,任选地平均为约0.5微米或更小的或中间的或更大的尺寸。
在本发明的一个示例实施方案中,聚合物珠直径在10-250微米、任选地15-150微米的范围内,平均值为约25、30、40、50、60微米。例如,基于如上所述的凝固考虑事项(setting considerations),更小的或更大的或中间的直径也是可能的。在某些情况下,大颗粒尺寸,例如,直径超过120微米的颗粒(例如当平均直径为大约60微米时)是硫酸钡初级颗粒聚集在PMMA颗粒珠上的结果。
在表IV中描述了表III的示例水泥的珠尺寸示例分布,基于0.04-2000微米范围内的颗粒的分析:
表IV:骨水泥第二示例粉末状组分的颗粒尺寸分布
Vol.% | 10 | 25 | 50 | 75 | 90 |
最大珠直径[微米] | 2 | 9 | 46.5 | 70.7 | 90.5 |
图5是视觉显示表IV的值的图。
尺寸和MW是独立的变量
在本发明的一个示例实施方案中,独立地确定基于尺寸和基于MW的子群。例如,MW可通过色谱法确定和尺寸可通过显微分析确定。因此,归入单个尺寸子群的珠可被归入两个或更多个MW子群,和/或归入单个MW子群的珠可被归入两个或更多个尺寸子群。
机械粘度增加剂(mechanical viscosity increasing agents)
在本发明的一个示例实施方案中,水泥包括不参与聚合反应的以大表面为特征的颗粒。所述大表面积颗粒可以独立于聚合给予水泥混合物附加的粘度。任选地,所述附加的粘度来自水泥中颗粒彼此之间的摩擦。
不参与聚合反应但增加粘度的材料的例子包括但不限于锆、硬化的丙烯酸类聚合物、硫酸钡和骨。
任选地,在影响粘度变化图时,不参与聚合反应但增加粘度的材料可以至少部分地代替高MW聚合物。
期望的聚合反应动力学
在本发明的一个示例实施方案中,聚合物与单体的混合从混合开始在180秒之内、任选地120秒之内、任选地100秒之内、任选地60秒之内、任选地30秒之内、任选地15秒之内,或更长的或中间的时间之内,基本上没有中间液相,产生高粘度混合物。
在本发明的一个示例实施方案中,一旦达到高粘度,该粘度就保持稳定5分钟、任选地8分钟、任选地10分钟,或更短的或中间的或更长的时间。任选地,稳定的粘度是指在2分钟内变化为10%或更小,和/或在8分钟内变化为20%或更小。期间粘度稳定的时间段提供了用于执行医疗过程的工作窗口。
这些期望的反应动力学可以通过调节以下一个或多个来实现:平均聚合物MW、聚合物MW分布、聚合物对单体的比例和聚合物珠尺寸和/或尺寸分布。
一般考虑
在本发明的一个示例实施方案中,粉末状聚合物组分和液体单体组分作为试剂盒提供。任选地,所述试剂盒包括使用说明书。任选地,使用说明书为不同的期望的聚合反应动力学指定不同的粉末与液体比例。
在本发明的一个示例实施方案中,提供了包括至少两个、任选地三个或更多个分别包装的珠的子群和单体液体的骨水泥试剂盒。任选地,所述试剂盒包括表格,所述表格提供基于不同数量的珠的子群和单体的组合的配方以实现期望的性能。
在丙烯酸类聚合物水泥的配方中,在粉末状聚合物组分中包含引发剂(例如过氧化苯甲酰;BPO)和/或在液体单体组分中包含化学活化剂(例如DMPT)是常见的实践。这些组分可任选地被添加到根据本发明的示例实施方案的配方中而不减损水泥的期望性能。
任选地,在所述液体组分中添加易氧化分子(例如氢醌)以防止在储存期间的自发聚合(稳定剂)。在储存期间氢醌可被氧化。
任选地,例如通过向所述粉末和/或液体组分添加不透辐射的(radio-opaque)材料如硫酸钡和/或锆化合物和/或骨(例如碎片或粉末),可使水泥变得不透辐射。
尽管上述说明集中在脊骨上,但也可以处理其它组织,例如压实胫骨板(compacted tibia plate)及其它有压缩骨折的骨头,和用于固定松掉的植入物或在植入过程中固定植入物,例如髋(hip)植入物或其它骨植入物。任选地,为紧固已有的植入物,向骨中存在空隙(void)的地方钻小孔并将材料挤入所述空隙中。
应当注意,尽管记述了使用所公开的材料作为骨水泥,但也可任选地处理非骨组织。例如,需要紧固的软骨或软组织可被注以高粘度的聚合物混合物。任选地,被递送的材料包括包封的药品并被用作基质来随着时间缓慢释放所述药品。任选地,这被用作向关节提供抗关节炎药物的手段,通过靠近关节形成空隙和植入洗脱材料(elutingmaterial)。
应当注意,虽然描述了使用PMMA,但还有各种各样的材料可适用于配制具有如上所述粘度特性的水泥。任选地,通过如以上所述考虑聚合物分子量(平均和/或分布)和/或珠尺寸,可以采用其它聚合物。任选地,至少一些珠包括苯乙烯。在本发明的一个示例实施方案中,苯乙烯被以5-25%的体积比添加到MMA珠。任选地,苯乙烯的添加提高了抗蠕变性。
根据本发明的不同实施方案,本发明的骨水泥被作为预防疗法和/或作为对骨折、畸形(deformity)、缺陷(deficiency)或其它异常(abnormality)的治疗被注入骨空隙中。任选地,所述骨为椎体和/或长骨。在本发明的一个示例实施方案中,水泥被插入长骨的髓管中。任选地,水泥在放置到骨中之前或期间被模制成棒。在本发明的一个示例实施方案中,所述棒充当髓内钉。
示例性表征工具
可例如通过凝胶渗透色谱(GPC)系统(例如Waters 1515等强度(isocratic)HPLC泵,具有Waters 2410折射率检测器和具有20-μl回路的Rheodyne(Coatati,CA)喷射阀(Waters Ma))来分析分子量和多分散性。采用CHCl3通过线性Ultrastyragel柱(Waters;500-孔径)以1ml/min的流速洗脱样品提供了令人满意的结果。
应当理解,例如在可利用的注射力、粘度、阻力程度(degree ofresistance)和能经受的力(例如骨头或注入工具能经受的力)之间的各种折衷(tradeoffs)可能是理想的。此外,已经描述了方法和水泥配方的许多不同特征。应当理解,不同的特征可以以不同方式结合。特别是,在上面特定实施方案中示出的所有特征在本发明的每个类似实施方案中并不是都是必需的。此外,上述特征的组合也被认为是处在本发明的一些示例实施方案的范围之内。此外,根据本发明的其它示例实施方案,本文描述的本发明的某些特征可被调整以用于现在技术装置。
提供节标题只是用于帮助阅读本申请,不应被理解为是将某节中描述的内容必然限定于该节。提供的措施(measurements)仅用作针对特定情形的示例措施,所应用的具体措施将根据应用而变化。在用于以下权利要求中时,术语″包括″、″包含″、″含有″、″含″等是指″包括但不限于″。
本领域技术人员应当理解,本发明并不限于到目前为止已描述的内容。相反,本发明的范围仅由以下权利要求限定。
Claims (5)
1.一种水泥试剂盒,包括:
(a)包括单体的液体组分;和
(b)包括聚合物珠的粉末组分,
其中所述粉末组分的聚合物珠的分子量分布为非正态分布,从而当加入更高分子量珠时出现偏斜分布,所述粉末组分的分子量的非正态分布使得(1)与具有正态分布的水泥相比,所述液体和粉末组分的混合物的瞬时粘度增大,和(2)工作窗口增长,其中所述水泥的粘度相对于具有正态分布的水泥不超过500帕·秒。
2.权利要求1的水泥试剂盒,其中所述更高分子量珠的平均分子量是所述聚合物珠的平均分子量的至少2倍。
3.权利要求2的水泥试剂盒,其中所述更高分子量珠的平均分子量是所述聚合物珠的平均分子量的至少3倍。
4.权利要求3的水泥试剂盒,其中所述更高分子量珠的平均分子量是所述聚合物珠的平均分子量的至少5倍。
5.权利要求1的水泥试剂盒,其中还包括包含更小尺寸聚合物珠的较小组分。
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CN200780034128.8A Active CN101516412B (zh) | 2006-09-14 | 2007-09-11 | 骨水泥及其使用方法 |
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US (2) | US9642932B2 (zh) |
EP (1) | EP2068898A4 (zh) |
CN (1) | CN101516412B (zh) |
AU (1) | AU2007297097A1 (zh) |
CA (1) | CA2663447A1 (zh) |
WO (1) | WO2008032322A2 (zh) |
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- 2007-09-11 EP EP07805589A patent/EP2068898A4/en not_active Withdrawn
- 2007-09-11 WO PCT/IL2007/001130 patent/WO2008032322A2/en active Application Filing
- 2007-09-11 US US12/377,894 patent/US9642932B2/en active Active
- 2007-09-11 AU AU2007297097A patent/AU2007297097A1/en not_active Abandoned
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2017
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CA2663447A1 (en) | 2008-03-20 |
US10272174B2 (en) | 2019-04-30 |
US20100168271A1 (en) | 2010-07-01 |
EP2068898A2 (en) | 2009-06-17 |
WO2008032322A2 (en) | 2008-03-20 |
WO2008032322A3 (en) | 2009-05-07 |
US9642932B2 (en) | 2017-05-09 |
EP2068898A4 (en) | 2011-07-20 |
CN101516412A (zh) | 2009-08-26 |
AU2007297097A1 (en) | 2008-03-20 |
US20170216483A1 (en) | 2017-08-03 |
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