CN1173692C - 化妆品组合物和降低皮肤老化过程的方法 - Google Patents
化妆品组合物和降低皮肤老化过程的方法 Download PDFInfo
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Abstract
本发明涉及适用于降低皮肤老化过程和/或处理皮肤病理损坏的化妆品组合物，所述的组合物含有式(I)的羟肟酸衍生物。
Description
本发明涉及一种化妆品组合物和降低皮肤老化过程和/或处理皮肤病理损坏的方法。
更具体地说，本发明涉及含有式(I)羟肟酸衍生物或其生理可接受的酸加成盐作为活性成分的化妆品组合物：
其中，
R1表示氢原子或C1-5烷基，
R2表示氢原子、C1-5烷基、C5-7环烷基或任选用羟基或苯基取代的苯基，或者
R1和R2与它们连接的氮原子一起形成5-8元环，其任选地含有一个或多个其它的氮或氧原子，并且所述的环可以与苯环稠合，
R3表示氢原子、苯基、萘基或吡啶基，其中所述的基团可以用一个或多个卤原子或C1-4烷氧基取代，
Y是羟基，
X表示氨基，
R与B形成化学键，
A是下式的基团
其中
R4表示氢原子，
R5表示氢原子，
m是0、1或2，
n是0、1或2。
人体皮肤是光辐射的天然目标，该光辐射具有几种已知使人舒适和不舒适(例如晒伤和致癌)的作用。由于紫外线辐射，在皮肤中形成自由基(例如羟基自由基或初生态氧)。这样的自由基可以损伤DNA并促使皮肤老化。
已知的皮肤老化过程的理论是以自由基的损坏作用为基础的。除了紫外线辐射作用外，在生物化学过程中也可以形成自由基。因此，由于例如发炎、缺氧或反应性充血，可以形成氧源的自由基例如超氧化物阴离子、过羟基或羟基自由基、过氧化氢等。
具有很强氧化作用的自由基一方面可以通过将膜的不饱和脂肪酸组份氧化(脂类的过氧化)损伤膜，另一方面，在氧化期间形成反应性醛。在损伤膜的过程中，增加钙吸收导致细胞死亡，由于存在反应性醛，所以开始了病理过程：
-损伤DNA、在细胞核和线粒体中发生变异；
-由于形成交联改变了空隙蛋白质(例如弹性蛋白)的性质。
已知的是：胶原蛋白和弹性蛋白的弹性结构含有大量的水。空隙蛋白的特征是：它们富有细胞赖氨酸。反应性醛例如丙二醛与含氨基的侧链发生缩聚反应形成交联体。因此，原先是弹性的结构变成刚性和疏水。在上述过程中，首先形成脂暗褐菌素蜡样质，然后形成色素。
抵抗紫外线辐射的自然保护机理包括：由于形成黑素而晒黑、DNA修复机理等。保护机理的缺陷(例如DNA修复的损害和校正由紫外线引起的DNA损伤的必然损失)导致皮肤的过早老化或者也许导致称之为着色性干皮病的疾病，该疾病可以伴随有恶性肿瘤的发展。医治在早期童年时由晒黑引起的晒伤斑点留下增大的疤痕。除了棘细胞癌外，还可以发展成各种恶性肿瘤(例如，黑素瘤、角质棘皮病、基底细胞癌(basalioma)、肉瘤)。
因此，倘若可以影响皮肤的老化过程和治疗病理损伤则是非常重要的。
式I的羟肟酸衍生物是已知的。HU-P 177578和其同族US 4308399描述了适用于治疗糖尿病血管病的式I化合物中的羟肟酸衍生物。
HU-P 207988和其同族EP 417210也描述了具有选择性β-阻滞作用，因此适用于治疗糖尿病血管病的羟肟酸卤化物。
HU-P专利中请2385/92，其公开号为T/66350进一步描述了羟肟酸衍生物。这些已知的化合物可以用于治疗血管变形，重要用于治疗糖尿病(diabetes mellitus)。
本发明的目的是提供一种适用于降低皮肤老化过程和/或处理皮肤病理损坏的组合物。
已经发现上述目的是这样的组合物实现的，该组合物含有式(I)的羟肟酸衍生物或其生理可接受的酸加成的盐作为活性组份。
本发明适用的皮肤病理损伤，尤其指的是下面这些：
-干皮肤；
-光化性角化病、光化性痒疹(Lopez-Gonzalez氏病)；
-多形光疹；
-毒性光病；
-光过敏反应；
-老年紫癜病；
-皮肤的日光(照射)萎缩；
-青春条纹(条纹migrans)；
-弹性组织瘤扩散(老皮)；
-X-射线皮炎；
-痛风性多软骨炎；
-褥疮(褥疮)。
在说明书和权利要求书中，术语“组合物”首先指的是适用于局部处理和以常规方法涂覆于皮肤表面的化妆品组合物。
本发明的组合物在与一种或多种化妆品组合物常规载体的混合物中含有式(I)的羟肟酸衍生物或其生理可接受的酸加成的盐作为活性组份。
在说明书和权利要求书中，C1-5烷基是：例如，甲基、乙基、正丙基、异丙基、正丁基或正戊基，优选甲基或乙基。
C5-7环烷基是环戊基、环己基或环庚基，优选环戊基或环己基。
含一个或多个杂原子的5-8元环可以是：例如，吡咯、吡唑、咪唑、唑、吡啶、哒嗪、嘧啶、哌嗪、吗啉、吲哚、喹啉等等环。
卤原子是：例如，氟、氯、溴或碘原子，优选氯或溴原子。
式I化合物的生理可接受的酸加成的盐是与生理可接受的无机酸例如盐酸、硫酸等或者与生理可接受的有机酸例如乙酸、富马酸、乳酸等形成的酸加成的盐。
式I化合物的优选亚组由下式的羟肟酸衍生物组成：
其中R1、R2、R3、R4、R5、m和n与式I中所述相同，X表示氨基，Y表示羟基。
式II的特别优选化合物是这样的化合物，其中R1和R2与它们连接的氮原子一起形成哌啶基，R3表示吡啶基，m和n是0，X与上面的定义相同。这些化合物中，优选的是下面这些：O-(3-哌啶基-2-羟基-1-丙基)吡啶-3-基羟肟酸氯化物(化合物“A”)和O-(3-哌啶基-2-羟基-1-丙基)烟酰胺肟(化合物“B”)。
通过从HU-P 177578已知的方法可以制备式I的化合物。
通常，本发明的组合物一般含有0.1-30％(重量)，合适为2-10％(重量)，优选为4-5％(重量)的式I羟肟酸衍生物或其生理可接受的酸加成盐作为活性组份和化妆品组合物的常规载体。
本发明的组合物可以是适合于局部处理皮肤表面的常规化妆品制剂。优选的制剂是乳剂、人体用乳液、日光乳液、皮肤处理泡沫、喷雾、皮肤再生针剂等。
除了活性组份外，本发明的组合物可以含有化妆品组合物的常规载体，其量通常为70-99.9％(重量)。合适的载体是：例如，具有饱和或不饱和碳链的一价或二价醇例如十六烷醇、硬脂醇、十六烷基硬脂醇、油醇、月桂醇、乙二醇、丙二醇、甘油；天然油脂例如橄榄油、鳄梨油、麦胚芽油、玉米胚芽油、羊毛脂、可可油；高级烃例如凡士林油、凡士林；蜂蜡；纤维素衍生物；乳化剂例如月桂基硫酸钠、脱水山梨醇的脂肪酸或油酸酯、聚(乙二醇)的脂肪酸或油酸酯、脂肪醇或油醇的脱水山梨醇醚、脂肪醇或油醇的聚(乙二醇)醚、脂肪酸的甘油酯；维生素；草药提取物例如春黄菊提取物；防腐剂例如对羟基苯甲酸甲酯、氯代hexidine葡萄糖酸酯；光保护因子等。
通过以已知的方法将其组份混合制备本发明的组合物。在基于水/油或油/水乳液的情况下，通常分开地将脂肪相的组份和水相的组份混合，然后，如果需要的话，使用升高温度的脂肪相将两相混合。优选以水溶液形式将式I的活性组份加入到脂肪相或其它组份的混合物中。
在荷兰猪上检查式I化合物的抑制皮肤老化作用。将8只荷兰猪的皮肤表面拔掉毛，然后，在该动物1cm2面积的2个面上用100mJ/cm2强度的UV-B光照射。照射后，该动物的1个面涂上含有4％(重量)化合物“A”作为活性组份的实施例1的乳剂。每个动物的另1个面涂上不含有活性组份的化妆品载体混合物(即使用相应于实施例1的乳剂，但是所述的乳剂含有水代替活性组份)。因此，实际上，在试验中使用内对照物。
就4个动物来说，在照射后立即用乳剂进行处理，然后每天重复该处理1个星期(组I)。就其它4个动物来说，仅在照射后分别用本发明的乳剂和对照乳剂处理照射的皮肤表面24小时(组II)。
在组I动物的情况下，可以在照射和照射后用本发明组合物处理24和48小时的皮肤表面上观察到最小的红斑。在作为对照使用的皮肤表面上，可以注意到没有上皮的区域，这一状态在观察的7天期间都存在。从第4天，可以在照射和用本发明组合物处理的皮肤表面和周围皮肤之间检测出没有差别。
在组II的动物的情况下，在处理的区域以及在对照区域上可以观观察到皮肤损伤(囊泡，大庖)，于是发展成没有上皮的区域。在照射后第7天时，用本发明组合物处理的区域形成上皮。
根据上面的试验，可以证实：本发明的组合物和式I的化合物分别保护皮肤表面免受损伤影响。如果在照射后立即用本发明的组合物处理皮肤表面，那么最多仅受到弱的上皮损伤。
由UV-B辐射形成的皮肤损伤由于用本发明的组合物处理，所以治愈时间比没有处理的短。式I的化合物发挥了形成上皮的作用。
因此，本发明的其它实施方案包括降低皮肤老化过程和/或处理皮肤病理损坏的方法，所述的方法包括用有效无毒量的式I羟肟酸衍生物或其生理可接受的酸加成的盐处理损伤的皮肤表面。
用含有0.1-30％(重量)的式I羟肟酸衍生物或其生理可接受的酸加成的盐的化妆品组合物处理皮肤表面是合适的。
优选地，O-(3-哌啶基-2-羟基-1-丙基)烟酰胺肟或其生理可接受的酸加成的盐处理皮肤表面。
用下面实施例进一步说明本发明。
实施例1
乳剂(油/水)
该乳剂由下面组份组成：
化合物“A” 4.0％(重量)
十六烷基硬脂醇 7.5％(重量)
硬脂酸 9.0％(重量)
单硬脂酸甘油酯 2.0％(重量)
月桂基硫酸钠 0.5％(重量)
对羟基苯甲酸甲酯 0.1％(重量)
蒸馏水 76.9％(重量)
100.0％(重量)
在水浴上将亲油组份(十六烷基硬脂醇、硬脂酸和硬脂酸单甘油酯)熔融。在60-65℃将月桂基硫酸钠和对羟基苯甲酸甲酯溶于38ml蒸馏水中，通过加入稀氢氧化钠水溶液将该溶液的pH到9-10，然后将该水溶液与混合进亲油组份的混合物，搅拌得到的乳液直到冷却。将活性组份溶解在剩余的水中并将该溶液混合进冷却的溶剂中。
实施例2
乳剂(水/油)
该乳剂由下面组份组成：
化合物“A” 5.0％(重量)
十六烷基硬脂醇 10.0％(重量)
白蜡 10.0％(重量)
中性油 35.0％(重量)
ImwitorR780K(植物脂肪酸的偏 5.0％(重量)
甘油酯)
对羟基苯甲酸甲酯 0.1％(重量)
蒸馏水 34.9％(重量)
100.0％(重量)
使用实施例1中所述的方法将这些组份混合。
实施例3
乳剂(水/油)
该乳剂由下面组份组成：
化合物“A” 5.0％(重量)
十六烷基硬脂醇 1.5％(重量)
白蜡 1.5％(重量)
lanalcol 2.5％(重量)
胆甾醇 1.0％(重量)
白凡士林 43.5％(重量)
四硼酸钠 2.0％(重量)
对羟基苯甲酸甲酯 0.1％(重量)
蒸馏水 42.9％(重量)
100.0％(重量)
使用实施例1中所述的方法将这些组份混合。
实施例4
晚上用的保湿乳剂
使用在实施例1中所述的方法制备由下面组份组成乳剂：
化合物“B” 5.0％(重量)
十六烷醇 5.0％(重量)
羊毛脂(无水) 5.0％(重量)
椰子油 5.0％(重量)
凡士林 5.0％(重量)
凡士林油 5.0％(重量)
肉豆蔻酸异丙基酯 1.0％(重量)
棕榈酸异丙基酯 1.0％(重量)
麦胚芽油 10.0％(重量)
晚樱草油 5.0％(重量)
维生素A 0.03％(重量)
维生素E 0.05％(重量)
甘油 5.0％(重量)
丙二醇 5.0％(重量)
对羟基苯甲酸甲基酯 0.2％(重量)
香料 0.1％(重量)
去离子水 42.62％(重量)
100.0％(重量)
实施例5
白天用的保湿乳剂
使用在实施例1中所述的方法制备由下面组份组成乳剂：
化合物“B” 5.0％(重量)
十六烷醇 5.0％(重量)
羊毛脂(无水) 5.0％(重量)
凡士林 5.0％(重量)
凡士林油 5.0％(重量)
肉豆蔻酸异丙基酯 1.0％(重量)
棕榈酸异丙基酯 1.0％(重量)
麦胚芽油 4.0％(重量)
花生油 11.0％(重量)
维生素A 0.03％(重量)
维生素E 0.05％(重量)
甘油 5.0％(重量)
丙二醇 5.0％(重量)
对羟基苯甲酸甲酯 0.2％(重量)
香料 0.1％(重量)
去离子水 47.62％(重量)
100.00％(重量)
实施例6
人体奶液
用实施例1中所述的方法制备由下面组份组成的人体奶液。
化合物“B” 4.0％(重量)
硬脂酸单甘油酯 2.0％(重量)
十六烷基硬脂醇 2.0％(重量)
花生油 5.0％(重量)
凡士林油 3.0％(重量)
聚氧乙烯十六烷基硬脂醇(聚合度：20) 2.0％(重量)
甘油 4.0％(重量)
对羟基苯甲酸甲酯 0.2％(重量)
对羟基苯甲酸丙酯 0.1％(重量)
丁基羟基甲苯 0.01％(重量)
去离子水 77.69％(重量)
100.00％(重量)
Claims (8)
1.含有式(I)羟肟酸衍生物或其酸加成盐与一种或多种常规化妆品载体掺混的组合物在制备用于降低皮肤老化过程的化妆品中的用途：
其中，
R1表示氢原子或C1-5烷基，
R2表示氢原子、C1-5烷基、C5-7环烷基或用羟基或苯基任选取代的苯基，或者
R1和R2与它们连接的氮原子一起形成5-8元环，其任选地含有一个或多个其它的氮或氧原子，所述的环可以与苯环稠合，
R3表示氢原子、苯基、萘基或吡啶基，其中所述的基团可以用一个或多个卤原子或C1-4烷氧基取代，
Y是羟基，
X表示氨基，
R与B形成化学键，
A是下式的基团
其中
R4表示氢原子，
R5表示氢原子，
m是0、1或2，
n是0、1或2。
2.根据权利要求1的用途，其中所述组合物含有如下定义的式I化合物或其酸加成盐，其中R1和R2与它们所连的氮原子一起形成哌啶基，R3，A，X，B，R和Y按权利要求1定义。
3.根据权利要求1的用途，其中所述组合物含有O-(3-哌啶基-2-羟基-1-丙基)烟酰胺肟或其酸加成盐。
4.根据权利要求1-3中任一项的用途，其中所述组合物含有0.1-30％(重量)的活性组份。
5.含有式(I)羟肟酸衍生物或其酸加成盐与一种或多种常规化妆品载体掺混的组合物在制备用于治疗皮肤病理损伤的药物中的用途：
其中，
R1表示氢原子或C1-5烷基，
R2表示氢原子、C1-5烷基、C5-7环烷基或用羟基或苯基任意取代的苯基，或者
R1和R2与它们连接的氮原子一起形成5-8元环，其任选地含有一个或多个其它的氮或氧原子，所述的环可以与苯环稠合，
R3表示氢原子、苯基、萘基或吡啶基，其中所述的基团可以用一个或多个卤原子或C1-4烷氧基取代，
Y是羟基，
X表示氨基，
R与B形成化学键，
A是下式的基团
其中
R4表示氢原子，
R5表示氢原子，
m是0、1或2，
n是0、1或2。
6.根据权利要求5的用途，其中所述组合物含有如下定义的式I化合物或其酸加成盐，其中R1和R2与它们所连的氮原子一起形成哌啶基，R3，A，X，B，R和Y按权利要求5定义。
7.根据权利要求5的用途，其中所述组合物含有O-(3-哌啶基-2-羟基-1-丙基)烟酰胺肟或其酸加成盐。
8.根据权利要求5-7中任一项的用途，其中所述组合物含有0.1-30％(重量)的活性组份。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9503728A HUT78139A (hu) | 1995-12-22 | 1995-12-22 | Készítmény, különösen a bőr öregedési folyamatainak mérséklésére |
| HUP9503728 | 1995-12-22 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96199664A Division CN1207670A (zh) | 1995-12-22 | 1996-12-20 | 化妆品组合物和降低皮肤老化过程的方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1263762A CN1263762A (zh) | 2000-08-23 |
| CN1173692C true CN1173692C (zh) | 2004-11-03 |
Family
ID=10987504
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96199664A Pending CN1207670A (zh) | 1995-12-22 | 1996-12-20 | 化妆品组合物和降低皮肤老化过程的方法 |
| CNB991243994A Expired - Fee Related CN1173692C (zh) | 1995-12-22 | 1999-11-30 | 化妆品组合物和降低皮肤老化过程的方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96199664A Pending CN1207670A (zh) | 1995-12-22 | 1996-12-20 | 化妆品组合物和降低皮肤老化过程的方法 |
Country Status (17)
| Country | Link |
|---|---|
| EP (2) | EP1025838B1 (zh) |
| JP (2) | JP2001509129A (zh) |
| KR (1) | KR19990076669A (zh) |
| CN (2) | CN1207670A (zh) |
| AT (1) | ATE237306T1 (zh) |
| AU (1) | AU1167397A (zh) |
| CA (1) | CA2240505A1 (zh) |
| DE (1) | DE69627547T2 (zh) |
| DK (1) | DK1025838T3 (zh) |
| ES (1) | ES2197565T3 (zh) |
| HK (1) | HK1029943A1 (zh) |
| HU (1) | HUT78139A (zh) |
| IL (2) | IL132854A (zh) |
| PT (1) | PT1025838E (zh) |
| RU (1) | RU2197954C2 (zh) |
| UA (1) | UA46083C2 (zh) |
| WO (1) | WO1997023198A1 (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2813195B1 (fr) * | 2000-08-29 | 2003-04-04 | Serobiologiques Lab Sa | Utilisation d'extraits de la plante cassia alata dans des produits de soin |
| DE10240989A1 (de) * | 2002-09-05 | 2004-03-11 | Uwe Klewinghaus | Zusammensetzung und deren Verwendung als pharmazeutische oder kosmetische Formulierung zur äußerlichen Anwendung |
| HUP0401177A2 (en) * | 2004-06-14 | 2007-09-28 | N Gene Res Lab Inc | Pharmaceutical composition for increasing the mitochondrial genesis |
| HUP0500145A2 (en) * | 2005-01-28 | 2006-11-28 | Gene Res Lab N | Use of o-(3-piperidino-2-hydroxy-1-propyl)-nicotinic amidoxime for preparation of medicaments against oral diseases |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1404481A (fr) * | 1963-04-16 | 1965-07-02 | Hoffmann La Roche | Procédé pour la préparation de nouveaux 3-éthers de la nu-(alpha, gamma-dihydroxy-beta, beta-diméthyl-butyryl)-propylamine |
| HU177578B (en) * | 1976-08-27 | 1981-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing new 0-/3-amino-2-hydroxy-propyl/-amidoxime derivatives |
| HU184626B (en) * | 1979-06-01 | 1984-09-28 | Ferrokemia Ipari | Congesting cosmetics first of all hair-restorers |
| HU207988B (en) * | 1988-10-20 | 1993-07-28 | Biorex Kutato Fejlesztoe Kft | Process for producing halogenides of o-/3-amino-2-hydroxy-propyl/hydroximic acid and pharmaceutical compositions containing them as active components |
| TW233264B (zh) * | 1992-02-03 | 1994-11-01 | Otsuka Pharma Co Ltd | |
| HU222994B1 (hu) * | 1995-11-02 | 2004-01-28 | BIOREX Kutató és Fejlesztő Rt. | Hidroxilaminszármazékok és azok alkalmazása sejtek molekuláris chaperon-termelésének fokozására alkalmas gyógyszerkészítmények előállítására |
-
1995
- 1995-12-22 HU HU9503728A patent/HUT78139A/hu unknown
-
1996
- 1996-12-20 ES ES99123365T patent/ES2197565T3/es not_active Expired - Lifetime
- 1996-12-20 JP JP52344497A patent/JP2001509129A/ja active Pending
- 1996-12-20 PT PT99123365T patent/PT1025838E/pt unknown
- 1996-12-20 AT AT99123365T patent/ATE237306T1/de not_active IP Right Cessation
- 1996-12-20 EP EP99123365A patent/EP1025838B1/en not_active Expired - Lifetime
- 1996-12-20 KR KR1019980704781A patent/KR19990076669A/ko not_active Application Discontinuation
- 1996-12-20 AU AU11673/97A patent/AU1167397A/en not_active Abandoned
- 1996-12-20 DE DE69627547T patent/DE69627547T2/de not_active Expired - Fee Related
- 1996-12-20 IL IL132854A patent/IL132854A/en not_active IP Right Cessation
- 1996-12-20 UA UA98073917A patent/UA46083C2/uk unknown
- 1996-12-20 WO PCT/HU1996/000081 patent/WO1997023198A1/en not_active Application Discontinuation
- 1996-12-20 CA CA002240505A patent/CA2240505A1/en not_active Abandoned
- 1996-12-20 CN CN96199664A patent/CN1207670A/zh active Pending
- 1996-12-20 DK DK99123365T patent/DK1025838T3/da active
- 1996-12-20 IL IL12498496A patent/IL124984A0/xx unknown
- 1996-12-20 RU RU99125652/14A patent/RU2197954C2/ru not_active IP Right Cessation
- 1996-12-20 EP EP96942539A patent/EP0869771A1/en not_active Withdrawn
-
1999
- 1999-11-24 JP JP33302699A patent/JP3806277B2/ja not_active Expired - Fee Related
- 1999-11-30 CN CNB991243994A patent/CN1173692C/zh not_active Expired - Fee Related
-
2001
- 2001-02-09 HK HK01100921A patent/HK1029943A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PT1025838E (pt) | 2003-09-30 |
| AU1167397A (en) | 1997-07-17 |
| EP0869771A1 (en) | 1998-10-14 |
| EP1025838A1 (en) | 2000-08-09 |
| HUT78139A (hu) | 2000-11-28 |
| IL132854A (en) | 2006-06-11 |
| JP2001509129A (ja) | 2001-07-10 |
| EP1025838B1 (en) | 2003-04-16 |
| CA2240505A1 (en) | 1997-07-03 |
| DE69627547D1 (de) | 2003-05-22 |
| HK1029943A1 (en) | 2001-04-20 |
| UA46083C2 (uk) | 2002-05-15 |
| ATE237306T1 (de) | 2003-05-15 |
| CN1207670A (zh) | 1999-02-10 |
| DE69627547T2 (de) | 2003-12-24 |
| JP3806277B2 (ja) | 2006-08-09 |
| KR19990076669A (ko) | 1999-10-15 |
| WO1997023198A1 (en) | 1997-07-03 |
| DK1025838T3 (da) | 2003-08-11 |
| CN1263762A (zh) | 2000-08-23 |
| JP2000302657A (ja) | 2000-10-31 |
| HU9503728D0 (en) | 1996-02-28 |
| ES2197565T3 (es) | 2004-01-01 |
| IL124984A0 (en) | 1999-01-26 |
| RU2197954C2 (ru) | 2003-02-10 |
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