CN1181979A - 防止手术后粘连的生物可消溶的氧化纤维素复合材料 - Google Patents
防止手术后粘连的生物可消溶的氧化纤维素复合材料 Download PDFInfo
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Abstract
本申请公开一种改进的防止粘连的物理隔离层、绷带和药物输送装置,包括由多层的纤维素织物或类似材料和纤维素薄膜组成的氧化纤维素薄膜。本申请还公开一种形成改进的氧化纤维素薄膜和使用所说的改进的氧化纤维素薄膜防止形成手术后粘连和/或包扎伤口和/或输送一种或多种药物的方法。
Description
本发明涉及用于防止手术后粘连的物理隔离层,并且更具体说,涉及用于防止手术后粘连的、由氧化纤维素组成的生物可消溶的氧化纤维素复合材料。
粘连,疤痕连接是由于成纤维细胞向内生长有关的纤维蛋白引起的二个或多个的体表面的不正常的连接。虽然具体的致病原因尚不完全清楚,但是这样的连接可能是由于与外科手术有关的手工操作和化学伤害的结果。这样的粘连是手术后发病和致死的主要原因。的确,高达百分之九十的全部外科手术导致形成这样的粘连和接近百分之十的这样的粘连使病人引起一系列的并发症。参见Ellis,H,The Causes and Prevention of IntestinalAdhesions,Br.J.Surg.69.241~43,1982,Weibel M.A.Majno,G.,Peritoneal Adhesions and their Relation to AbdominalSurgery,AM.J.Surg.126.345~53,1973。这样的并发症具体不一,但是包括不育症、肠梗阻、关节丧失正常运动功能、等等。例如,心脏手术后形成的粘连进一步增加了包括在其后的胸骨切开术中的各种危险。参见DobellA.R.C.and Jain,A.K.,Catastrophic Hemorrhage During RedoSternotomy,Ann.Thorac.Surg.37:273-78,1984。
外科手术对病人的潜在危险性和害处、粘连已成为整百年来的研究目标。先前在防止粘连方面的尝试可被分成如下几类:(1)防止纤维蛋白的沉积;(2)除去纤维蛋白的渗出物;(3)抑止成纤维细胞增殖和(4)表面分离。
尽管这些方法的每一种已取得一点点成功,但是在治愈期间使用物理隔离层来限制组织外积迄今还是取得了也许是最大的正面效果。参见Wiseman.D.M.,Polymers for the Prevention of Surgical Adhesions,inPolymer Site Specific Pharmacotherapy,369~421(A.Domb ed.1994)(John Wiley,Chichester,Publisher)。早期的方法是使用从鱼膀胱膜到银或金箔的物理隔离层的各种材料。然而,很快认识到这些办法不能提供对防止形成粘连来说是必不可少的长期作用。虽然更近代的方法包括使用凝胶和液体,但是迄今最好的办法是使用固体物理隔离层。
一种使用固体物理隔离层的惯用方法包括使用泡沫聚四氟乙烯(“PTFE”)片以达得想望的物理分离,如Hubbel等人的美国专利№5468505和Haney,A.F.,Hesla,J.,Hurt,B.,Kettle,L.M.,Murphy,A.A.,Rock,J.A.,Rowe G.&Schlaff,W.D.,Prevention of Pelvic SidewallAdhesion Reformation Using Surgical Barriers:ExpandedPolytetrafluorethylene(Gore-TexSurgical Membrane)issuperior to Oxidized Regenerated Cellulose(InterceedTC7),Fertil.Steril.(Prog Supp),p.265,s.210(1994)中所述。尽管提供了想望的组织的物理分离,但是PTFE是非吸收性的并因此未被优选。在现有技术还充分知道的是,留在体内的上述材料会引起很大的感染可能性。
利用由可吸收的材料例如聚交酯、聚乙交酯及其共聚物制成的物理隔离层的尝试已取得有限度的成功,这部分是该材料的多孔性和纤维性加重了身体对上述材料的天生的排异性之故。参见Wiseman,D.M.Polymers for thePrevention of Surgical Adhesions in Polymer Site SpecificPharmacotherapy,369~421(A.Domb ed.1994)(John Wiley,Chichester,Publisher)。隔离层诸如由Johnson&Johnson以商品名INTERCEED(TC7)销售的可吸收的粘合隔离层效果更好,因为它们是由氧化的再生纤维素(“ORC”)组成的,而氧化的再生纤维素对组织具有较低的反应性。然而,部分由于以下的事实:(1)该材料含有在水合作用时不能足够快地闭合以防止纤维蛋白从隔离层的一侧到另一侧的贯通的微孔。这种从一组织到另一组织的纤维蛋白桥促使粘连形成。本发明的复合材料的发明人已发现就某些应用而言,例如防止心包粘连,或在由于发炎而引起的长时间的纤维蛋白沉积情况中,为了防止粘连需要更大量的较小的微孔;和(2)隔离层可能太快地丧失其完整性或某些解剖学上的位置(例如,在心脏的周围)引起器官移动而促使解体或错位。即使是由如Linsky等人的美国专利№4840626中所说的ORC组成的隔离层也仅得到有限的使用。
已经知道,由氧化纤维素组成的材料引起最小的组织反应。这首先是在1936年由W.Kenyon在Eastman Kodak实验室发现的。在Mr.Kenyon的关于氧化纤维素的基础研究中,发现了通过使用二氧化氮的氧化纤维素制成的一类新产品。此种新材料溶于碱并且与通过其他的氧化纤维素方法生产的通常的脆性材料相反,这种新材料保持其初始形态和其大部分的初始拉伸强度。已经证实,此种新产品是葡糖酐和失水葡糖苷酸的共聚物。这种新的氧化纤维素材料后来被Parke Davis和Johnson&Johnson开发成为生物可消溶的织物止血剂。有关该方法的详细讨论可见以下各参考文献:Kenyon,R.,Oxidationof Cellulose,INDUS.&Engin.Chem.,Vol.41(1)2-8,1949;美国专利№2232990、2298387、3364200和5180398及其相应的外国同属专利EP0492990和日本专利申请№361083/91。
于是,仍需要一种防止手术后粘连的生物可消溶的物理隔离层,这种防止手术后粘连的生物可消溶的物理隔离层是(1)比惯用的织造或针织织物材料具有较少的微孔,(2)能方便和可靠地固定在想望的位置,和(3)不包含允许纤维蛋白沉积和纤维向内生长的微孔。
根据本发明的一个方面,将氧化纤维素的连续的复合薄膜用作物理隔离层以限制组织外积、缩少或一起防止形成手术后的粘连。使用这种连续的复合薄膜克服使用现在正被应用的微孔织物的内在缺陷。该氧化纤维素复合材料是通过形成纤维素薄膜和内部防破裂材料,诸如人造丝、纤维素针织织物或非织造织物或纤维素纸的多层夹芯结构而构成的。薄膜和织物或纸是用纤维素粘合剂例如淀粉、甲基纤维素或微晶纤维素浆粘合在一起的而在氧化时成为生物可消溶的。参见一起待审的美国专利申请№_____。该复合材料用赋予其以生物可消溶性的二氧化氮氧化。随后可用伽马辐照对其进行杀菌。此氧化步骤将纤维素聚合物中的伯羟基转变成羧基并使聚合物易受水和酶的水解作用。然后将得到的材料用于制备手术植入的、生物可消溶的医疗产品。所得到的氧化纤维素多层复合材料具有氧化纤维素组成的生物可消溶的织物所有想望的特性(例如,生物可消溶性、可缝合性、低的组织反应性等等)以及与组织接触的光滑、连续、无微孔表面的另外好处。因为该复合薄膜包含防破裂材料,所以它能被缝合在应有位置例如作为心脏修补片。
此外,由于较少的吸附表面之故,与织物表面相比光滑表面上的细胞与组织的粘连将减少。此特性大大地提高了物理隔离层的成功率。细胞对底基的粘连强力影响其许多功能并因此在包括培育、吞噬、止血和组织对植入材料的排斥的各种生物过程中起重要的作用。在1986年9月举行的由美国化学会发起的有关生物材料的表面特性的学术讨论会中,Buddy Ratner和另外一些人指出,生物材料植入物的光滑表面与粗糙表面相比引起较少的细胞反应和较轻的组织发炎。
此外,氧化纤维素多层薄膜是柔软的、耐久的、以及最重要的是可缝合的。该材料的柔软性通过用正如以前所使用的盐水或其他生理上可接受的液体的浸润得到改进。因此,此多层薄膜能被方便和可靠地固定(例如,通过缝合)到想望的位置。该氧化纤维素多层薄膜还缺乏粘性并因此不会被粘到手套或手术器械上。
在本发明的另一方面,该氧化纤维素薄膜能在不与防破裂材料结合一起的情况下被使用。由于在被缝合后氧化纤维素薄膜本身会撕裂,因此氧化纤维素薄膜能用生理上可接受的组织粘合剂例如纤维蛋白胶或氰基丙烯酸酯粘合剂固定在应处的位置上。该氧化纤维素薄膜本身会起适用的物理隔离层的作用,薄膜的光滑性减少细胞和分子对其表面的粘连。
在本发明的再一个方面,氧化纤维素复合薄膜材料可药物处理,诸如肝素处理相结合,以增加隔离层的效果。这样的药物可以通过表面吸附或在氧化后与完全干燥前通过将复合材料浸渍在药物溶液中而结合到复合材料上。在有关的应用中,氧化纤维素复合薄膜材料可用作绷带。由于其柔性与吸收药物之故,氧化纤维素复合材料是珍贵的包扎材料。另外,这样的包扎材料能被用来输送一种或多种药物到包扎位置以有助于伤口的痊愈。
在其方法方面,本发明包括一种形成本发明的氧化纤维素复合簿膜材料的方法。此外,本发明的另一种方法方面是通过将本发明的氧化纤维素复合簿膜材料作为隔离层置于手术处与邻近组织之间以限止组织外积。
氧化纤维素复合薄膜多层物理隔离层的使用提供了限止组织外积所不可缺少的物理隔离层、0RC材料的生物可消溶性、以及方便和可靠的连接与减少材料的生物敏感性。
在本发明的再一个方面,氧化纤维素薄膜被用作绷带。而在本发明的另一个不同的方面,被用作绷带的氧化纤维素薄膜还起输送药物装置的作用,在治疗伤口时将一种或多种的药物供应到伤口处。
在本发明的优选的实施方案中,氧化纤维素多层薄膜作为物理隔离层被置于手术处与邻近组织之间,以限止组织外积并由此减少手术后粘连的形成。氧化纤维素多层薄膜是根据本发明的形成这样的氧化纤维素多层薄膜方法的优选实施方案形成的。该薄膜是由被夹置于(2)二片纤维素薄膜之间和用(3)甲基纤维素胶或淀粉浆胶结在一起的(1)一层纤维状纤维素层组成的。然后,将此复合材料氧化以产生氧化纤维素多层薄膜。
甲基纤维素胶的制备如下:将约一克的甲基纤维素(取代度为1.65~1.92)诸如得自Dow Chemical Company商标为METHOCEL A4MTM的甲基纤维素悬浮于约140°F的50ml蒸馏水中。搅拌此悬浮液同时让其冷却到室温。得到清晰、低粘度的甲基纤维素溶液。接着,在蒸馏水中浸湿纤维素薄膜并在玻璃板或其他光滑、平整和通常为非粘性的表面上摊平。合适的纤维素薄膜可从Flexel,Inc.of Covington,Indiana购得。然后,将少量先前制备的甲基纤维素溶液或淀粉浆涂抹在纤维素薄膜表面上。然后将纤维状纤维素材料,例如得自Johnson&Johnson用于制造Surgicelor INTERCEED隔离层TM的针织或织造的人造丝织物前体,铺在纤维素薄膜的新涂胶面上。将第二纤维素薄膜用甲基纤维素胶或淀粉浆牢牢地覆盖在一面并放置到织物的相对面上以制成夹芯结构。然后将非粘性的隔离纸放在复合材料上并压上重物和任其干燥数天。
应当指出,尽管以上所说明的仅是二层纤维素薄膜和一层纤维状纤维素材料,但是,如果需要的话,可以使用由任何数目层的纤维素薄膜或纤维状纤维素材料相结合的纤维状纤维素材料。
在仅供说明而不是为了限止的情况下,在此例中,在复合材料上放置5公斤的重物,使其经过几天的干燥时间。此外,尽管这里所说的是使用重物和空气干燥,但是,如果需要的话,干燥可以使用本技术领域的熟练人员已知的标准方法通过重物、时间、温度和空气压力的任何结合来完成。干燥后,将多层复合材料夹芯物称重并放置到装有氢氧化钠阱放气孔的树脂釜中。此容器用取代空气的氮气冲洗。二氧化氮被骤冷到约10℃并且其量等于被放置在通过侧臂受管与树脂釜相连的小爱伦美氏烧杯中的复合材料重量的三倍。让二氧化氮升温到室温并扩散到装有多层复合材料的树脂釜。通过将其曝露在本身重量一至四倍的温度约在20℃和35℃之间的二氧化氮气体中而将多层薄膜氧化。最好是将多层薄膜材料在周围的大气压力下的二氧化氮气体中曝露4至48小时。在气体中曝露之后,容器用纯氮冲洗并用90%异丙醇溶液洗涤所得的氧化纤维素多层复合薄膜然后进行空气干燥。
复合薄膜可通过将甘油或聚丙二醇(10%溶液)添加到洗涤介质以赋予柔性而被塑化。氧化后氧化纤维素薄膜被牢牢地连接到氧化人造丝织物上。最后,多层薄膜材料被封合在包装中并通过伽马辐照(1.8MRad)杀菌。发现该氧化纤维素多层复合薄膜能完全溶解于0.5NNaOH而得到水稀释溶液。这表明材料可能是生物可消溶的。氧化纤维素多层复合薄膜的羧基含量通过滴定法测为10%~22%重量。由于羧基最高百分含量可能为25.5%,这表明在纤维素原料中37%~86%的伯醇基已经转化为羧基形式。
虽然上述的优选实施方案使用纤维状纤维素织物例如得自Johnson&Johnsonr用于制造Surgicelor INTERCEED隔离层TM氧化织物的人造丝织物,但是应当指出,如果需要的话,任何其他合适的纤维状纤维素织物或材料均可被使用。另外,虽然以上所述的是甲基纤维素胶,但是,如果需要的话,任何合适的能被氧化而产生生物可消溶材料的胶或粘合剂均可被使用,这些生物可消溶材料例如有淀粉、瓜耳胶、葡聚糖、乙基纤维素(取代度1.65~1.92)、一乙酸纤维素(取代度0.3~1.0)、羧甲基纤维素(取代度0.38~1.45)、羟乙基纤维素(可从Hercules以商品名Natrosol购得)、羟丙基甲基纤维素(取代度1.65~1.92)、羟丁基甲基纤维素(取代度1.65~1.92)、羟丙基纤维素(取代度1.65~1.92)或微晶纤维素。氧化纤维素衍生物的生产在一起待审的美国专利申请No_______中被更详细地讨论。羧甲基纤维素可从Aqualon并以取代度为0.38~1.45的不同级别购得。可从Hercules购得的乙基纤维素聚合物具有DS为2.46,此值太高以致不能使纤维素主链上的伯羟基和仲羟基充分氧化并被赋予生物可消溶性,这可以通过在0.5N氢氧化钠溶液中的溶解得到证实。然而,如果具有取代度为0.3~1.0的乙基纤维素用四氧化二氮氧化的话,它将转变成生物可消溶的氧化纤维素衍生物。
还应当指出,纤维素薄膜并不是能用于本发明的唯一种材料。能氧化而产生生物可消溶材料的其他生物可消溶薄膜,例如一乙酸纤维素薄膜(取代度0.5~1.0)、羧甲基纤维素薄膜(取代度0.38~1.45)、乙基纤维素薄膜(取代度0.3~1.0)和甲基纤维素薄膜(取代度1.65~1.92),当被用于本发明方法中时也能起合适的手术后粘连的隔离层作用。在一起待审的美国专利申请No________中,发明人已公开了使用浸渍到ORC织物中的氧化甲基纤维素。
与常规ORC材料的具有更多的微孔和纤维性相比,氧化纤维素多层薄膜的较光滑性被认为是有助于减少细胞、大分子和其他组织的粘连。所用的试验方法
本发明的各种氧化纤维素多层薄膜的效果可以通过如下的兔子心包粘连和兔子侧壁粘连模式来测定。所有的动物是盲目和无规地指定为某一处理组的,只在当完成磨损后才对外科医生显示。心包粘连模式
此模式按Wiseman D.M.,Kamp,L.,Linsky,C.B.,Jochen,R.F.,Pang,R.H.L.,Scholz,P.Fibrinolytic Drugs Prevent PericardialAdhesions in the Rabbit.J.S urg.Res.53,362~68,1992中所述进行。在麻醉和消毒操作下通过中心胸切开线进入到新西兰白兔的胸膛。通过切开线相似地打开心包并使用一块缠绕外科医生手指的纱布磨擦心脏的前表面。以受控方式用纱布击打心脏的前表面40次。
接着,如果使用本发明方法的生物可消溶的粘连隔离层的话,将一块轴线近似为2″×1″的椭圆形隔离材料片放置在心脏的前表面上并且,如果需要的话,将其缝合到心包。如果动物是对照动物的话,不使用物理粘连隔离层而外科医生跳到下面所述的下一步骤。动物的心包和胸随后以层形式封闭。
在手术后的二十三至三十天,将这些动物杀死并评估手术后粘连情况。估计1cm宽的从前心表面的顶部延伸到前心表面的底部的粘连条的百分率。此条代表与胸骨密切接触的部分心脏表面,此区域是最可能形成粘连和外科医生企图重新打开胸腔的可能的最难处。
在不使用药物溶液情况下从上述的心包试验所得的结果被示于以下的各表中:
对照试验
处 理 动物 № 粘连百分率
未处理 228-50 100
未处理 228-30 70
未处理 228-05 100
未处理 229-04 90
未处理 229-19 100
平 均 92
标准差 13.04
N 5
氧化纤维素多层薄膜
处 理 动 物 № 粘连百分率
薄 膜 225-14 15
薄 膜 227-04 5
薄 膜 228-31 30
薄 膜 228-51 5
薄 膜 228-40 60
薄 膜 228-01 5
薄 膜 229-14 25
薄 膜 229-15 25
平 均 21.25
标准差 18.67
N 8
如以上所示的处理试验结果所说明的那样,用本发明的氧化纤维素多层薄膜粘连隔离层处理的动物在形成手术后粘连方面显示出明显的改进(研究者的T-试验p<0.001)。此外,心脏表面的目测检查显示由氧化纤维素多层薄膜引起的非常轻度的发炎。兔子侧壁粘连模式
此模式按Diamond,M.P.,Linsky,C.B.,Cunningham,T.,ConstatineB.,Dizerega,G.S.,Decherney,A.H,A Model for SidewallAdhesions in the Rabbit:Redction by an Absorbable Barrier,Microsurgery 8;197~200,1987中所述进行。在麻醉和消毒操作下使用母新西兰白兔(2~6kg),通过下腹中切线进入下腹。使用10号曲解剖刀并且从离子宫分叉1cm开始在每一子宫角的二侧的2cm长度上的每一侧擦括20次。通过填塞物止血。此外,形成肌腹膜全厚度(2×2cm)切口并使用6-0缝合法在接近擦伤的子宫角距损伤侧壁和子宫角3~5mm缝合。随后伤口以层状形式闭合。手术后二周,使动物无痛苦地死亡并且通过事前不知道的观察评估其中粘连形成的情况对手术区进行检查。根据标准方法评估粘连的形成情况和性质,其中特别注意粘连的程度、类型和性质。
尽管在以上详细的说明书中已对本发明的优选实施方案作了介绍,当然本发明并不限于这些公开的实施方案,但是在不违背本发明的精神的前提下能够对本发明作出种种的变换和改进。
Claims (30)
1.一种成形用作防止粘连的隔离层的氧化纤维素多层薄膜的方法,包括以下步骤:
在一表面上铺展纤维素薄膜,
将至少为一层的纤维素织物材料与所说的纤维素薄膜相结合以形成多层薄膜,
氧化所说的多层薄膜,和
消毒所说的多层薄膜。
2.权利要求1的方法,其中将至少为一层的纤维素织物材料与所说的纤维素薄膜相结合以形成多层薄膜包括使用粘合剂。
3.权利要求2的方法,其中所说的粘合剂是一种选自淀粉、瓜耳胶、葡聚糖、乙基纤维素、一乙酸纤维素、羧甲基纤维素、羟乙基纤维素、羟丙基甲基纤维素、羟丁基甲基纤维素、羟丙基纤维素或微晶纤维素的,能氧化而形成生物可消溶的材料。
4.权利要求1的方法,其中所说的纤维素薄膜选自纤维素薄膜、一乙酸纤维素薄膜、羧甲基纤维素薄膜、瓜耳胶薄膜、魔芋薄膜、淀粉薄膜、葡聚糖薄膜和微晶纤维素薄膜。
5.权利要求1的方法,其中氧化包括将多层薄膜曝露在二氧化氮中。
6.权利要求5的方法,其中多层薄膜在二氧化氮中被曝露4~48小时。
7.权利要求5的方法,其中多层薄膜被曝露在压力为1与5大气压之间的二氧化氮中。
8.权利要求5的方法,其中多层薄膜被曝露在温度为20℃与35℃之间的二氧化氮中。
9.权利要求1的方法,另外包括在氧化步骤之后和消毒步骤之前的洗涤多层薄膜步骤。
10.权利要求9的方法,其中多层薄膜步骤是用异丙醇溶液洗涤的。
11.权利要求1的方法,其中消毒多层薄膜包括伽马辐照。
12.权利要求1的氧化纤维素多层薄膜。
13.权利要求1的方法,另外包括用至少一种的多羟基醇增塑所说的多层薄膜而赋予它以柔软性的步骤。
14.权利要求13的方法,其中至少一种的多羟基醇选自甘油和丙二醇。
15.权利要求1的方法,其中将至少为一层的纤维素织物材料与所说的纤维素薄膜相结合以形成多层薄膜步骤包括使用防破裂材料。
16.一种成形用作防止粘连的隔离层的氧化纤维素多层薄膜的方法,包括以下步骤:
在一表面上铺展纤维素薄膜,
使用一种可氧化的碳水化合物粘合剂将至少为一层的纤维素织物材料与所说的纤维素薄膜相结合以形成多层薄膜,
在20℃~35℃之间的温度和1~5大气压力下在二氧化氮存在的情况下氧化所说的多层薄膜4~48小时,和
消毒所说的多层薄膜。
17.权利要求16的方法,其中所说的纤维素薄膜选自纤维素薄膜、一乙酸纤维素薄膜、淀粉薄膜、瓜耳胶薄膜、魔芋薄膜、葡聚糖薄膜、羧甲基纤维素薄膜和甲基纤维素薄膜。
18.权利要求16的方法,其中所说的粘合剂是一种选自淀粉、瓜耳胶、葡聚糖、魔芋、羧甲基纤维素、羟乙基纤维素、甲基纤维素、羟丙基纤维素和微晶纤维素的,能氧化而形成生物可消溶的材料。
19.权利要求16的方法,另外包括在氧化步骤之后和消毒步骤之前的洗涤多层薄膜步骤。
20.权利要求16的方法,其中消毒多层薄膜包括伽马辐照。
21.权利要求16的氧化纤维素多层薄膜。
22.权利要求16的方法,另外包括用至少一种的多羟基醇增塑所说的多层薄膜而赋予它以柔软性的步骤。
23.权利要求22的方法,其中至少一种的多羟基醇选自甘油和丙二醇。
24.权利要求16的方法,其中将至少为一层的纤维素织物材料与所说的纤维素薄膜相结合以形成多层薄膜步骤包括使用防破裂材料。
25.一种防止手术粘连的方法,包括将作为物理隔离层的氧化纤维素多层薄膜放置在手术位置与邻近的组织位置之间以防止手术后的粘连的步骤。
26.权利要求25的方法,其中与所说的氧化多层薄膜一起使用药物溶液以防止手术后的粘连。
27.权利要求26的方法,其中所说的药物溶液被结合到氧化纤维素多层薄膜中以防止手术后的粘连。
28.权利要求25的方法,其中所说的氧化多层薄膜是通过权利要求1的方法形成的。
29.一种处理伤口的方法,包括放置作为绷带的氧化纤维素多层薄膜。
30.权利要求29的方法,其中作为绷带的所说的氧化多层薄膜将至少一种的药物输送到伤口以有助于治愈伤口。
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US11957798B2 (en) | 2017-12-19 | 2024-04-16 | Omrix Biopharmaceuticals Ltd. | Wound dressing and a method for producing the same |
CN112569400A (zh) * | 2020-11-13 | 2021-03-30 | 东华大学 | 一种Janus止血敷料及其制备方法 |
Also Published As
Publication number | Publication date |
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EP0815881A3 (en) | 1999-12-22 |
AU2754197A (en) | 1998-01-22 |
CA2208754C (en) | 2007-05-29 |
IN192450B (zh) | 2004-04-24 |
EP0815881A2 (en) | 1998-01-07 |
AU716142B2 (en) | 2000-02-17 |
DE69721388T2 (de) | 2004-04-01 |
DE69721388D1 (de) | 2003-06-05 |
CN1118301C (zh) | 2003-08-20 |
ES2197309T3 (es) | 2004-01-01 |
EP0815881B1 (en) | 2003-05-02 |
CA2208754A1 (en) | 1997-12-28 |
BR9703774A (pt) | 1998-11-10 |
JPH1099422A (ja) | 1998-04-21 |
US6500777B1 (en) | 2002-12-31 |
JP4275204B2 (ja) | 2009-06-10 |
MX9704970A (es) | 1998-05-31 |
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