CN1245222C - 植入用顺性脱水组织的制备方法 - Google Patents
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- Y10S623/00—Prosthesis, i.e. artificial body members, parts thereof, or aids and accessories therefor
- Y10S623/915—Method or apparatus for preparing biological material
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Abstract
一种耐裂无活细胞的柔韧的软组织样品的制备方法,该方法包括下列步骤:将从供体得到的天然软组织用溶液处理,所述溶液为逐渐地梯度增加脂肪醇或者其它合适的水溶性极性有机溶剂直到最后的醇(或者其它溶剂)溶液具有至少25体积%的有机液体水溶液。其后将组织样品用含甘油或者(分子量低1000D)的低分子量的聚乙二醇、分子量为约6000-15000D的聚乙二醇和肝素的溶液处理。然后将所述组织样品简单地浸入到肝素水溶液中,冷冻并冷冻干燥。所述组织样品在再水合或者不再水合下,适于作为同种移植物或者异种移植物植入。
Description
发明背景
1.发明领域
本发明属于植入材料的领域。更具体地说,本发明涉及顺性脱水植入材料,它们没有活细胞,并且可以不浸入液体中进行储存和运输。本发明也涉及生产所述植入材料的方法。
2.现有技术的简要描述
使用自体移植、同种移植和异种移植加强或者置换人类和动物的受损组织已经公知有很长的时间。从提供适当的移植材料的角度上看,加强或者置换骨等硬组织与加强和或者置换软组织表现出不同的问题。在选择硬组织植入物的替代材料方面,植入物的强度和硬度较重要,而顺性和柔性一般地讲不太主要。
另一方面,选择植入的软组织材料时,植入材料的顺性和柔性一般最重要,因为软组织置换材料通常必须与将被置换的功能健康的组织相匹配。在这个方面应当记住含有胶原的原软组织强度大,能够耐受反复的三维的应力及弯曲和形变。通常原软组织起着必须保持其结构整合性的物理屏障的作用。理想地,用于移植的加强或者置换的软组织应当与其所置换的原软组织有同样的特性,并且应当易于得到、保存及运输。但是,这些却是现有技术的努力难以达到的目标,并且在本发明前均不太成功。
更具体地说,根据现有技术的主要研究,为了保存软组织用于最终移植,将人或者动物源的组织一直用化学改性剂/保存剂处理,例如与胶原和其它的蛋白质交联的戊二醛。戊二醛处理的组织植入人体后表现有适当的耐机械疲劳性及生物降解性。然而,戊二醛交联改变了组织的粘弹特性,而且因此,作为宿主反应的结果,随着时间的推移通常在植入物中发生不利的钙化和周围粒性组织增生。戊二醛是有效的杀菌剂(灭菌剂),但是暴露于空气中就会慢慢地失去其杀菌效力。因此打算用于移植的组织(生物假体)须保存在戊二醛溶液中储存和运输,并且包括戊二醛浸泡的生物假体的包装必须保持高度密封。而且它不能暴露在显著升高的温度下。因为这些要求,使用戊二醛处理的软组织生物假体的成本较高。戊二醛是有毒性的,因此植入前必须仔细地漂洗以从生物假体上去除戊二醛。这是用戊二醛处理的生物假体的又一个缺点。
在现有技术中提供软组织生物假体的另一个主要研究是使用液体消毒剂而不是戊二醛。这些其它的研究中也有避免与戊二醛处理的植入物关联的钙化问题。但是,按照这些方法,为了避免脆性,以及为了或多或少地保持生物假体的物理整合性,所述组织必须在液体媒介中保持、储存和运输直到马上进行移植手术之前。
提供软组织生物假体的又一个其它方法是用低温保存同种移植(同一物种的组织)的新鲜组织。由于近来在低温保存方面的进步,低温保存的新鲜组织近来使同种移植的植入更加成功,并且更加被接受作为戊二醛保存的异种移植的替代。低温保存生物假体的一个严重的缺点是难于保证它们没有感染致病剂。制备和处理低温保存的生物假体的成本也非常地高,因为需要在所有的时间把组织保存在低于通常的或者说一般的冷冻温度下。
数个现有技术的专利的公开涉及制备和/或保存移植用生物组织或者其它用作替换组织,我们对美国专利5,116,552(Morita等)和5,336,616(Livesey等)感兴趣。美国专利5,116,552(Morita等)描述了一种用于制备低压冻干的医用胶原海绵体,如人造皮肤的方法。这个参考文献的方法包括:用亲水的有机溶剂的水溶液浸渍交联的胶原海绵体,冷冻海绵体,然后真空干燥(低压冻干)之。然而,得到的冻干产品是不柔韧的,并且不能防止断裂,因为在冷冻干燥步骤中去掉了水及亲水的溶剂或溶剂。美国专利5,336,616(Livesey等)说明了处理从诸如尸体之类的来源得到的软组织,它用含有抗氧化剂、蛋白酶抑制剂和抗生素(稳定溶液)的溶液处理,用酶和清洁剂去除活性抗原细胞(处理溶液),并且在脱细胞后用低温保存液处理,低温保存液在冷冻组织时防止形成破坏性的冰晶。低温保存液可以包括有机溶剂和水的混合物。在低压冻干以后,将制品在密封的容器中、在惰性气体环境中储存和运输,以此防止大气中的湿气。在移植前,将组织再水合,并且必须用免疫耐受的活性细胞恢复,以产生移植用的永久可接受的植入物。
其它的有关制备和/或保存移植用生物组织,或者相关主题的公开文献可见于美国专利2,106,261;2,610,625;2,645,618;3,939,260;4,277,238;4,280,954;4,300,243;4,383,832;4,578,067;4,703,108;4,704,131;4,760,131;4,801,299;4,911,915;5,028,597;5,131,850;5,674,290和英国专利说明书716,161。
发明概述
本发明的一个目的是提供一种软组织移植物,该移植物适用于植入人或者其它哺乳动物,这种移植物在再水合之后具有与由之得到移植物的天然软组织有基本上相同的机械特性。
本发明的另一个目的是提供一种软组织移植物,它满足以上的目的,它还没有活细胞并且不需要在植入前接种活细胞。
本发明的又一个目的是提供一种软组织移植物,它满足以上的目的,可以以脱水的形式储存和运输。
上述及其它目的和优点是通过一种软组织制备得到的,该软组织在其脱水状态是顺性抗裂的,没有活细胞并且是通过系列处理天然的软组织得到的:
用液体组合物处理,逐渐地增加该液体组合物中的C1-C3醇的浓度或者其它极性的水溶性有机溶剂的浓度,直到最后所述液体组合物含有至少25体积%的醇或者其它的极性有机溶剂或者其混合物,其余部分是水;
其后用第二液体组合物进行处理,该液体组合物含有甘油或者低分子量(<1000D)的聚乙二醇或者其混合物,浓度范围在10于50体积%左右,所述第二液体组合物还含有约3%-20%重量/体积的分子量为6000D到15000D的聚乙二醇,和约每毫升2到75单位的分子量大于约3KD的肝素;
然后,把如此处理软组织中的过多液体排掉;
然后,把软组织浸入到浓度约每毫升20至500单位的肝素水溶液中,然后冷冻此组织并且把此组织低压冷冻干燥。
通过下面对特定实施方式和实施例的详细说明会很好地理解本发明的特征以及本发明的目的和优点。
优选的具体实施方式的描述
以下的说明提出本发明的优选实施方式。本发明揭示的实施方式是发明人构思的实施本发明的最佳方式,但是应当理解可以在本发明的参数范围内作各种修改。
根据本发明欲植入哺乳动物包括人类的软组织首先从来源诸如尸体得到。牛、绵羊、猪组织和从绵羊之类的其它动物得到的软组织,就可作为例子。也可以使用人的软组织。
同种移植物,就是说作为供体的组织移植到同种中;及异种移植,就是说作为供体的组织移植到与供体不同的种属中,都可以按照本发明制备。根据本发明使用的组织类型一般地与现行的主要用于人类的涉及软组织移植手术常用的类型相同。此类手术中常用的组织例子是心包、主动脉和肺动脉根部、腱、韧带、皮肤、腹膜、胸膜、二尖瓣和三尖瓣。
从供体切下的软组织通常进行整理以去除松散的多余或者不需要的组织和脂肪。一般将组织浸泡在盐水中。然后按照本发明,把组织在第一水溶液中处理,该第一水溶液含有较低浓度(约15-35%)的C1-C3醇,然后在较高醇浓度约25-75%范围的第二水溶液中处理。(除特殊说明外,本文所述浓度均为体积比)。用第一和第二溶液处理组织样品的目的是逐渐地用醇置换样品中的水成分。甲醇、乙醇和异丙醇可用于此目的,优选乙醇。其它无毒极性的水溶性有机溶剂乙腈、丙酮、或者甲乙酮也可以用于代替上述醇,醇和有机溶剂的混合物也适用于本发明。优选地,第一溶液含有约25%乙醇,其余为水,第二溶液含有约50%的乙醇,其余为水。
本领域内的技术人员容易了解,上述操作代表用按步骤地梯度增加醇(或者其它适宜的无毒的水溶性的溶剂)的浓度处理组织样品,直到达到至少约25%,优选约50%,最优选约75%的醇(或者其它适宜的溶剂)浓度。替代上述两步浓度梯度处理组织样品,所述样品也可以用三步或更多步的浓度梯度处理或甚至用连续增加浓度梯度直至达到醇(或其它合适的溶剂)浓度。用增加醇的浓度梯度(或者其它适宜的溶剂)的处理是在环境温度下进行的,并且最优选的是把组织样品浸泡在溶液中进行的。把组织样品放在这些溶液中的时间并不是关键的,并且或多或少地取决于组织的厚度。但是应当给予足够的时间让溶液渗透进样品。典型地,30分钟足够,而在本发明的方法的优选实施方式中,组织样品在第一和第二每个醇溶液中各保持约30分钟。
在上述的醇溶液中浸泡(处理)后,将所述组织样品浸入(处理)到一种第三溶液中,该第三溶液含有约10至50%甘油、约3至20%重量/体积(w/v)的分子量在6000D到15000D范围的聚乙二醇和约每毫升2到75单位分子量大于约3KD的肝素。优选地,第三溶液含有约20%甘油、约5%(w/v)的分子量约为8000D聚乙二醇和约每毫升50单位的肝素。在第三溶液中可以用低分子量(<1000D)的聚乙二醇代替甘油。在第三溶液中浸泡的时间也不是关键,对于很薄的组织约30分钟,例如绵羊、猪、牛或者人的心包就足够了,但是对于较厚的组织适宜且较好放在溶液中的时间较长,例如6个小时,或者优选地12个小时。
用第三溶液处理完毕之后,取出组织样品并且使多余的液体从组织样品中排出。然后暂短地(快速地浸几秒)浸入或另外用浓度约每毫升20至500单位,优选地浓度约每毫升250单位,的肝素水溶液处理,然后使之排掉肝素溶液。然后,以本领域内常用的冷冻方式在低压冻干样品前冷冻样品。本领域内的技术人员理解这种冷冻一般地是在超低温冰箱中进行的,温度约在-60℃至-80℃。冷冻后以本领域内公知的方式把组织样品低压冻干(真空冷冻干燥)。
按照本发明处理的组织样品是半透明的,呈淡黄的色彩。与用100%的水或者生理盐水低压冷冻干燥的组织不同,本发明的组织是柔韧的,顺性的,并且不会由于物理性操作裂开或者破损。
为了在外科手术中用作移植物,并且对于根据本发明进行的旨在与用新鲜组织处理的组织作比较的大多数试验,首先将低压冷冻的组织用生理缓冲盐水再水合。这优选地通过将本发明的低压冷冻的组织在生理缓冲盐水浸泡约5分钟至1个小时进行。本发明的再水合后的组织外观实际上与新鲜组织的外观没有差别。再水合一般在环境温度进行。这可以在患者自己的血液中、组织培养介质中和在低浓度(<10%)的乙醇溶液进行而不在盐水中进行。根据本发明的组织样品再水合的优选的方法是在pH值为7.4的缓冲盐水中进行。
如上所述,除非对本发明的组织样品进行试验,再水合只是在用组织样品移植前进行。其它情况下样品在防止环境湿气的密封容器品在环境温度下储存和运输。低压冷冻干燥的组织可以方便地用气相消毒的方法消毒,也可以不进行再水合就移植。
本发明的组织样品不含有活细胞,但是下文说明的试验表明在再水合后,组织样品没有细胞毒性并且对于要附着在其上增殖的宿主内皮细胞是相容性的。宿主内皮细胞的附着和增殖以及没有细胞毒性对于多数移植长期存活是重要的。本发明的组织是血液相容的并且抗血小板侵入和血栓形成。下述的试验表明在本发明的方法步骤中原有组织的胶原纤维基本上保持完好无损。
特殊举例和试验说明
(a)制备冷冻干燥的牛或者绵羊的心包
把新鲜的牛和绵羊心包切成条和块。切碎的目的是去除松散的组织和脂肪。把此组织立即放入25%的乙醇水溶液中30分钟。然后用50%的乙醇水溶液代替25%的乙醇水溶液再浸泡另30分钟。第二个(50%乙醇)溶液由第三溶液代替约16小时,第三溶液含有20%甘油、约5%(w/v)聚乙二醇(MW8000)和每毫升50单位(分子量大于3KD)的肝素。仔细地从第三溶液中取出组织,让多余的液体从组织排出,然后把组织浸入浓度为每毫升250单位的肝素溶液中几秒钟,再把组织在-70℃冷冻,把完全冷冻了的组织进行低压冷冻干燥。
以上得到的牛或者绵羊的低压冷冻干燥心包组织是半透明的,呈淡黄的色彩。它们是柔韧的,不会由于物理性操作裂开或者破损。它们可以通过室温浸入生理缓冲盐水中约5分钟而再水合。再水合后,这些组织与原来的新鲜组织外观上没有区别。
在再水合的心包上培养人的成纤维和脐带静脉内皮细胞,以研究其生物适应性。切出组织圆盘以配合24孔培养板的孔底。在组织上放置塑料圈以压下组织并且确保对组织的边缘进行良好的密封。把细胞接种在普通的培养介质中的组织上培养一周。培养期末揭开组织并且切成不同的部分进行组织学研究。组织截面的组织学检查表明薄层的内皮细胞附着在组织表面上。所述组织上的细胞也由胰蛋白酶释放并被计数。这些结果表明再水合的组织没有细胞毒性并且对于附着和增殖的宿主细胞是生物相容的。公知地,内皮细胞和其它的结缔组织在心植入物上的附着和增殖对于植入物的长期存活是基本的。
处理的组织中胶原纤维的整合性通过熔融温度进行检查。为此将组织在磷酸盐缓冲盐水中从37℃加热到它开始皱缩。新鲜的原组织的皱缩温度和根据本发明的低压冷冻干燥再水合的组织的皱缩温度大致相同,约为63+1℃,表明经低压冷冻干燥和再水合过程的胶原纤维保持完好无损。
(b)制备低压冷冻干燥的绵羊主动脉和肺动脉根
供体绵羊的主动脉和肺动脉根也用25%的乙醇水溶液、50%的乙醇水溶液、20%的甘油5%聚乙二醇水溶液、接着用肝素溶液处理,再进行低压冷冻干燥,如以上对牛和绵羊的心包处理所述。
把处理过的动脉根再水合后作为同种移植物植入宿主绵羊的降主动脉中。我们的结果表明,在植入100天以后,动脉瓣功能能够胜任,并且动脉根与非移植的原有组织末显不同。百天的移植未发生纤维蛋白的沉积和宿主组织反应。辩膜片显得完好无损,不论肉眼观察还是组织学检查与非移植的瓣膜均无法区别。
Claims (32)
1.一种制备柔韧的软组织样品的方法,包含步骤:
(1)将从供体得到的天然软组织,用
(a)第一多种液体组合物处理,逐渐地增加所述第一多种液体组合物中的一种或者多种极性有机溶剂的浓度,直到最后所述第一多种液体组合物含有至少25体积%的一种或者多种所述溶剂,其余部分是水,所述溶剂选自具有一至三个碳原子的脂肪醇和其它水溶性极性有机溶剂;
(b)其后用第二液体组合物处理,这种液体组合物含有浓度范围在10至50体积%的甘油或者分子量低于1000D的低分子量的聚乙二醇,所述第二液体组合物还含有3%-20%重量/体积的分子量为6000D到15000D的聚乙二醇,和每毫升2到75单位分子量大于3KD的肝素;
(2)然后,短暂地将软组织浸入到肝素的水溶液中;
(3)然后,冷冻所述软组织并且将其低压冷冻干燥。
2.根据权利要求1的方法,其中所述极性有机溶剂选自由甲醇、乙醇、异丙醇、乙腈、丙酮和甲乙酮组成的组中。
3.根据权利要求2的方法,其中所述极性有机溶剂是乙醇。
4.根据权利要求1的方法,其中将从供体得到的天然软组织用第一多种液体组合物处理,逐渐地增加所述第一多种液体组合物中的一种或者多种极性有机溶剂的浓度,直到最后所述第一多种液体组合物含有至少50体积%的一种或者多种所述溶剂。
5.根据权利要求4的方法,其中所述极性有机溶剂是乙醇。
6.根据权利要求1的方法,其中所述第二液体组合物含有20体积%的甘油。
7.根据权利要求1的方法,其中将天然软组织相继地用两种包含一种和多种极性有机溶剂的第一多种液体组合物处理,所述的第一多种液体组合物的第一种含有15至35体积%的所述一种或多种溶剂,所述的第一多种液体组合物的第二种含有25至75体积%的所述一种或多种溶剂。
8.根据权利要求7的方法,其中所述极性有机溶剂是乙醇。
9.根据权利要求1的方法,该方法还包括将低压冷冻干燥的组织样品再水合的步骤。
10.一种制备柔韧的哺乳动物软组织样品,用于最终植入哺乳动物中以置换或者强化原组织,的方法,包含步骤:
(1)将从供体得到的哺乳动物软组织,用(a)第一多种液体组合物处理,逐渐地增加所述第一多种液体组合物中的具有一到三个碳原子的脂肪醇或者脂肪醇混合物的浓度,直到最后所述第一多种液体组合物含有至少25体积%的所述醇或者醇的混合物,其余部分是水;
(b)其后用第二液体组合物处理,所述第二液体组合物含有浓度在10~50体积%范围内的甘油,还含有浓度范围在3%-20%重量/体积的分子量为6000D到15000D的聚乙二醇,和每毫升2到75单位分子量大于3KD的肝素;
(2)然后,暂短地将软组织浸入到浓度为每毫升20到500单位肝素的水溶液中;
(3)然后,冷冻所述组织并且将其低压冷冻干燥。
11.根据权利要求10的方法,其中所述脂肪醇是乙醇。
12.根据权利要求11的方法,其中将天然软组织用含有乙醇的第一多种液体组合物处理,直到最后所述第一多种液体组合物含有至少50体积%的乙醇。
13.根据权利要求12的方法,其中第二液体组合物中的甘油浓度为20体积%。
14.根据权利要求13的方法,其中第二液体组合物中的聚乙二醇浓度为5%重量/体积,所述聚乙二醇分子量为8000D。
15.根据权利要求14的方法,其中将天然软组织相继地用两种含有乙醇的第一多种液体组合物处理,所述的第一多种液体组合物的第一种含有15至35体积%的乙醇,所述的第一多种液体组合物的第二种含有25至75体积%的乙醇。
16.根据权利要求16的方法,该方法还包括将低压冷冻干燥的组织样品再水合的步骤。
17.根据权利要求10的方法,其中所述哺乳动物的天然软组织取自心包、胸膜、腹膜、主动脉、肺动脉、二尖瓣或者三尖瓣,或者取自腱或皮肤。
18.一种柔韧的软组织样品,该软组织样品用下列步骤制备:
(1)将从供体得到的天然软组织,用
(a)第一多种液体组合物处理,逐渐地增加所述第一多种液体组合物中的一种或多种极性有机溶剂的浓度,直到最后所述第一多种液体组合物含有至少25体积%的所述溶剂或者溶剂的混合物,其余部分是水,所述溶剂选自具有一至三个碳原子的脂肪醇和其它水溶性极性有机溶剂;
(b)其后用第二液体组合物处理,所述第二液体组合物含有浓度范围在10-50体积%的甘油或者分子量低于1000D的低分子量的聚乙二醇,所述第二液体组合物还含有3%-20%重量/体积的分子量6000D到15000D的聚乙二醇,和每毫升2到75单位分子量大于3KD的肝素;
(2)然后,暂短地将软组织浸入到肝素水溶液中;
(3)然后,冷冻所述组织并且将其低压冷冻干燥。
19.根据权利要求18的柔韧的软组织样品,其中在用于制备这种样品的方法中,所述极性有机溶剂选自由甲醇、乙醇、异丙醇、乙腈、丙酮、和甲乙酮组成的组中。
20.根据权利要求18的柔韧的软组织样品,其中在用于制备这种样品的方法中,将从供体得到的天然软组织,用第一多种液体组合物处理,逐渐地增加所述第一多种液体组合物中的一种或多种极性有机溶剂的浓度,直到最后所述第一多种液体组合物含有至少50体积%的所述溶剂或者溶剂的混合物。
21.根据权利要求20的柔韧的软组织样品,其中在用于制备这种样品的方法中,所述极性有机溶剂是乙醇。
22.根据权利要求18的柔韧的软组织样品,其中在用于制备这种样品的方法中,所述第二液体组合物含有18体积%的甘油。
23.根据权利要求18的柔韧的软组织样品,其中在用于制备这种样品的方法中,将天然软组织相继地用两种含有一种或多种极性有机溶剂的第一多种液体组合物处理,所述的第一多种液体组合物的第一种含有15至35体积%的一种或多种所述溶剂,所述的第一多种液体组合物的第二种含有25至75体积%的一种或多种所述溶剂。
24.根据权利要求18的柔韧的软组织样品,其中用于制备这种样品的方法还包括将低压冷冻干燥的组织再水合的步骤。
25.一种柔韧的软组织样品,用于最终植入哺乳动物中以置换或者强化原组织,用于制备这种样品的方法包含步骤:
(1)将从供体得到的哺乳动物原软组织,用(a)第一多种液体组合物处理,逐渐地增加所述第一多种液体组合物中的具有一到三个碳原子的脂肪醇或者脂肪醇的混合物的浓度,直到最后所述第一多种液体组合物含有至少25体积%的所述醇或者醇的混合物,其余部分是水;
(b)其后用第二液体组合物处理,所述第二液体组合物含有浓度范围为10~50体积%的甘油,所述第二液体组合物还含有3%-20%重量/体积的分子量6000D到15000D的聚乙二醇,和每毫升2到75单位分子量大于3KD的肝素;
(2)然后,暂短地将软组织浸入到浓度为每毫升20到500单位肝素的水溶液中;
(3)然后,冷冻所述组织并且将其低压冷冻干燥。
26.根据权利要求25的柔韧的软组织样品,其中在用于制备这种样品的方法中,所述脂肪醇是乙醇。
27.根据权利要求26的柔韧的软组织样品,其中在用于制备这种样品的方法中,将天然软组织,用含有乙醇的第一多种液体组合物处理,直到最后所述第一多种液体组合物含有至少50体积%的乙醇。
28.根据权利要求27的柔韧的软组织样品,其中在用于制备这种样品的方法中,第二液体组合物中的甘油浓度为20体积%。
29.根据权利要求28的柔韧的软组织样品,其中在用于制备这种样品的方法中,第二液体组合物中的聚乙二醇浓度为5%重量/体积,所述聚乙二醇分子量为8000D。
30.根据权利要求29的柔韧的软组织样品,其中在用于制备这种样品的方法中,将所述天然软组织相继地用两种含有乙醇的第一多种液体组合物处理,所述的第一多种液体组合物的第一种含有15至35体积%的乙醇,所述的第一多种液体组合物的第二种含有25至75体积%的乙醇。
31.根据权利要求25的柔韧的软组织样品,其中用于制备这种样品的方法中还包括将低压冷冻干燥的组织样品再水合的步骤。
32.根据权利要求25的柔韧的软组织样品,其中所述天然哺乳动物软组织取自心包、胸膜、腹膜、主动脉、肺动脉、二尖瓣或者三尖瓣,或者取自腱或皮肤。
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US09/103,874 US6630001B2 (en) | 1998-06-24 | 1998-06-24 | Compliant dehyrated tissue for implantation and process of making the same |
US09/103,874 | 1998-06-24 |
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- 1998-06-24 US US09/103,874 patent/US6630001B2/en not_active Expired - Lifetime
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1999
- 1999-06-23 BR BRPI9912180-8A patent/BR9912180B1/pt not_active IP Right Cessation
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- 1999-06-23 CN CNB998077364A patent/CN1245222C/zh not_active Expired - Fee Related
- 1999-06-23 ES ES99931880T patent/ES2178449T3/es not_active Expired - Lifetime
- 1999-06-23 DK DK99931880T patent/DK1089776T3/da active
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- 1999-06-23 WO PCT/US1999/014247 patent/WO1999066967A1/en active IP Right Grant
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EP1089776B1 (en) | 2002-05-29 |
ATE218067T1 (de) | 2002-06-15 |
CN1306445A (zh) | 2001-08-01 |
DK1089776T3 (da) | 2002-09-23 |
BR9912180B1 (pt) | 2011-05-31 |
AU4829899A (en) | 2000-01-10 |
BR9912180A (pt) | 2001-04-10 |
CA2335604C (en) | 2008-09-23 |
CA2335604A1 (en) | 1999-12-29 |
AU751506B2 (en) | 2002-08-15 |
HK1039284B (zh) | 2006-06-30 |
US6630001B2 (en) | 2003-10-07 |
DE69901612T2 (de) | 2003-02-13 |
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