CN1245166C - 改进的含有单糖类作为防腐增强剂的眼科和隐形眼镜用溶液 - Google Patents

改进的含有单糖类作为防腐增强剂的眼科和隐形眼镜用溶液 Download PDF

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CN1245166C
CN1245166C CNB018218172A CN01821817A CN1245166C CN 1245166 C CN1245166 C CN 1245166C CN B018218172 A CNB018218172 A CN B018218172A CN 01821817 A CN01821817 A CN 01821817A CN 1245166 C CN1245166 C CN 1245166C
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弗朗西斯·泽维尔·史密斯
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Abstract

一种隐形眼镜用溶液，含有0.1～5%重量比或从下面一组物质中选取的防腐增强剂：肌醇、甘露糖醇、蔗糖、葡萄糖、甘油和丙二醇；溶液中含有0.0001%重量比的阳离子型聚合物防腐剂，并且在所述溶液中氯化物浓度重量比低于0.2%。

Description

改进的含有单糖类作为防腐增强剂的眼科和隐形眼镜用溶液
本申请要求于2000年11月8日提交的美国临时专利申请No.60/246,870的权益。
技术领域
本发明涉及到眼科用溶液及其用途，尤其是涉及到隐形眼镜清洁溶液、隐形眼镜漂洗溶液和保藏溶液、将活性药物释放到眼睛的溶液、眼科器具及类似物品的消毒溶液。
背景技术
本发明涉及到眼科用溶液，尤其是有关长期使用后防腐效果和舒适性方面的内容。这些眼科用溶液已经使用了许多时间，并且可从许多产品中得到。这些溶液，用来直接与角膜组织接触，如将活性药物成分释入眼睛；或间接地与角膜组织接触，比如清洁、调节或保藏将与角膜组织接触的器具如隐形眼镜。很有必要确保这些溶液不引入细菌或其它微生物感染源。因而，在这些溶液中加入防腐剂以降低其中微生物的活性，从而减少使用者使溶液污染的机会，因为许多溶液被购买、打开、使用、密封、然后再使用。
现有技术的防腐剂，包括聚亚己基双胍(PHMB)、polyquadtm、洗必泰和洁尔灭及类似物质，所有这些物质在一定浓度下会刺激角膜组织，引起使用者不舒服的感觉。因而，在含有一定量防腐剂的溶液中加入一种非防腐剂成分，从而提高溶液防腐性能是很需要的。
发明内容
本发明涉及到改进的眼科用溶液，通过添加肌醇来提高溶液防腐性能，并且降低阳离子型防腐剂在隐形眼镜表面的沉积程度。眼科用溶液在这里理解为包括隐形眼镜护理溶液，如清洁液、浸泡液、调节溶液和镜片保藏溶液，以及调节眼睛用的润湿液和滴眼液。
本溶液在这里尤指含有0.001-1％肌醇，同时与其它在眼科用溶液中有用的有效组分复合，这些组分包括缓冲试剂、防腐剂、表面活性剂、抗微生物试剂和低浓度氯化物，它们的含量低于重量比0.2％。研究发现，肌醇以及其它糖类，包括甘露醇、山梨糖醇、蔗糖、葡萄糖、甘油和丙二醇等在低盐(低氯)条件下可以显著增强防腐剂的抗菌效果。
特别有用的防腐剂是阳离子型聚合物防腐剂，如聚亚己基双胍(PHMB)，polyquadtm、洗必泰和洁尔灭以及其它在本发明中也证明有用的阳离子型防腐剂。阳离子型防腐剂的加入量应保障其有防腐作用，如PHMB的用量按重量比为0.0001％到较高的约0.01％。具体地讲，阳离子型聚合物防腐剂包括聚双胍类物质，如聚亚己基双胍(PHMB)及其复合物。这些阳离子型聚双胍类物质以及由此形成的水溶性盐，具有如下分子式：
Figure C0182181700041
式中Z是一个有机二价桥式基团，在整个聚合物中可以相同，也可不同；n的平均数至少为3，最好是5-20；X1和X2是
-NH2和
Figure C0182181700042
一组好的水溶性聚双胍类物质的平均分子量至少在1,000以上，最好是平均分子量1,000-50,000。这些游离碱所形成的合适的水溶性盐类物质包括但不限于盐酸盐、硼酸盐、醋酸盐、葡糖酸盐、硫酸盐、酒石酸盐和柠檬酸盐等。
如上所示的双胍类物质及制备方法在文献中有描述。例如，美国专利US 3,428,576记述了由一个二胺及其盐和一个双氰亚胺的二胺盐制备出聚双胍的方法。
大多数情况下，优先使用商品化的亚己基双胍聚合物，例如Zeneca(Wilmington.Del.)公司的商标为Cosmocil TM CQ的盐酸盐。这些聚合物及水溶性盐是指聚亚己基双胍(PHMB)或聚氨基丙基二胍(PAPB)。
这里使用的术语聚亚己基双胍，意味着包含有一个或多个双胍基团，如下面分子式所示：
式中，Z、X1和X2如上所定义，n为1-500。
取决于双胍类物质的制备方式，在上述分子结构式中形成的主要化合物，X1和X2可以相同，也可以不同，其它结构化合物数量较少。这些化合物是已知的，在美国专利US 4,758,595和英国专利No.1,432,345中有记述，这些专利一并结合在此。最好，水溶性盐是其中n的平均数为2-15，最好是3-12的化合物。
已发现，当肌醇与阳离子防腐剂合用时，会有出人意料的防腐效果。溶液中其它组分的加入量在常知水平，用以改善镜片的耐磨性，并且当直接用于眼睛时，用以增加抗感染性。在一定的组方中，肌醇能增强眼科用溶液的防腐功效，在一定的组方中，增加眼角膜组织的抗感染性，并且在一定组方中能改善滴眼液的质量。
这些组方中也可以有缓冲试剂如磷酸盐、碳酸氢盐、柠檬酸盐、硼酸盐，N-(2-乙酰氨基)-2-氨基乙磺酸(ACES)、N，N-双(2-羟乙基)-2-氨基乙磺酸(BES)、N，N-双(2-羟乙基)氨基乙酸(BICINE)、2，2-双(羟甲基)-2，2，2-次氨基三乙醇胺(BIS-Tris)、1，3-双(三(羟甲基)甲氨基)丙烷(BIS-TrisPropane)、2-(4-(2-羟乙基)-1-哌嗪基)乙磺酸(HEPES)、N-(2-羟乙基)-哌嗪-N’-3-丙磺酸(HEPPS)、咪唑、2-(N-吗啉)乙磺酸(MES)、3-(N-吗啉)丙磺酸(MOPS)、哌嗪-1，4-双(2-乙磺酸)(PIPES)、N-三(羟乙基)甲基-3-氨基丙磺酸(TAPS)、N-三(羟乙基)甲基-2-氨基乙磺酸(TES)和三羟甲基甲基甘氨酸(Tricine)。
组方中也可加入表面活性剂如聚山梨醇酯表面活性剂、聚氧乙烯表面活性剂、膦酸酯、皂角苷和聚乙氧基蓖麻油，但最好是聚乙氧基蓖麻油。这些表面活性剂都是工业用品。聚乙氧基蓖麻油是BASF公司出售的商标为Cremaphor的产品。
在本发明中使用的肌醇、甘露糖醇、山梨糖醇、蔗糖和葡萄糖、甘油、丙二醇等也都是商业用品。对本领域的技术人员来说，它们都可以轻易地加入到本发明的组方中去。
本发明的溶液中可以包含其它添加剂，它包括但不限于缓冲试剂、张力剂、润湿剂、缓和剂、防腐剂、螯合剂、表面活性剂和酶等。
同时，溶液中可以添加其它方面的试剂，包括0.001-1％重量比的螯合剂(最好是EDTA二钠)和/或抗微生物剂，(最好是0.00001-0.1％或0.00001-0.01％重量比的)聚亚己基双胍、N-烷基-2-吡咯烷酮、洗必泰、聚季铵盐-1、六氢嘧啶(取代)(hexetidine)、2-溴-2-硝基-1，3-丙二醇、1，1’-亚己基-二(5-[2-乙基己基]双胍)、低浓度的过氧化氢和其它对眼睛无伤害的盐类。
本发明中使用的眼科允许的螯合剂包括氨基羧酸类化合物或其水溶盐，它们有乙二胺四醋酸、次氮基三醋酸、二乙基三乙胺五醋酸、羟乙基乙二胺三醋酸、1，2-二氨基环己基四醋酸、乙二醇双乙胺醚-N，N’-四乙酸(EDTA)、氨基二醋酸和羟乙基氨基二醋酸。这些酸可以以水溶性盐，尤其是碱金属盐的形式使用。特别指出的是，乙二胺四醋酸(EDTA)的二钠、三钠和四钠盐作为螯合剂效果较好，最好是EDTA二钠。
其它螯合剂如柠檬酸盐、多聚磷酸盐也可以在本发明中使用。本发明中使用的柠檬酸盐包括柠檬酸及其单、双和三碱金属盐。使用的多聚磷酸盐包括焦磷酸盐、三聚磷酸盐、四聚磷酸盐、三聚偏磷酸盐、四聚偏磷酸盐以及更高聚合度的磷酸盐。这些磷酸盐都以中性或酸性碱金属盐形式加入，比如钠盐、钾盐和铵盐。
溶液的pH应当调节到与眼睛和隐形眼镜相适应的范围，比如6.0和8.0之间，最好是6.8到7.8或7.0到7.6。偏离中性(pH 7.3)较大的溶液会引起隐形眼镜的物理参数(如直径)的改变；较低的pH(＜5.5)会导致眼睛灼伤和刺痛；而很低或很高的pH(＜3.0或＞10)能引起视觉损伤。
本发明中采用的附加防腐剂是已知的，例如有聚亚己基双胍、N-烷基-2-吡咯烷酮、洗必泰、1，1’-亚己基-二(5-[2-乙基己基]双胍)、聚季铵盐-1、六氢嘧啶(取代)(hexetidine)、2-溴-2-硝基-1，3-丙二醇、低浓度的过氧化氢(例如30-200ppm)的双氧水。
本发明溶液在贮藏、清洗、浸湿、浸泡、漂洗和消毒时与渗透性刚性气体和亲水性隐形眼镜是相适应的。
本发明的一个典型的水溶液中可以添加某些组分，它们不影响上面所提到的活性成分的基本特征和新颖特点，例如张力剂、表面活性剂和增稠剂。它们有助于清洗隐形眼镜，或能润滑眼睛。合适的张力剂包括氯化钠、氯化钾、甘油或其混合物。溶液的张力剂可以按每公斤溶液大约240-310毫渗透分子(mOsm/kg)的量进行调节，用以保障溶液与视觉组织和亲水性隐形眼镜相适应。在一个具体例子中，溶液中含有0.01-0.2％重量比的氯化钠。重要的因素是保证这些添加剂的浓度达到一定程度，即不会提供高于约0.2％摩尔的氯化钠浓度的程度。
合适的增稠剂包括卵膦脂或纤维素衍生物，比如羟甲基纤维素、羟丙基纤维素和甲基纤维素。其加入量与上面提到的表面活性剂用量相似。
具体实施方式
实施例1
本组方中含有肌醇(Spectrum公司)，将其溶于0.2％的磷酸缓冲溶液。溶液用氯化钠制成等渗透压溶液，并且加入0.0001％的聚亚己基双胍防腐。溶液的pH用1N的氢氧化钠或1N的盐酸调节至7.2。(试管)检测溶液抗菌活性的方法是：将白色棒状杆菌(C.albicans)加到10ml各溶液中，在室温下放置4小时。然后，将每种溶液等份地进行系列稀释，接种到琼脂平板上，在较高温度下培养48小时。培养期结束后，检测各平板上生长的菌落数。通过与细菌培养液对照样比较，确定对数下降值。下表是实验研究结果：
  添加剂   4小时的对数下降值
  肌醇(0.5％)   1.1
  缓冲溶液对照样   0.8
与缓冲溶液对照样相比，加入肌醇能够提高溶液的抗菌(C.albicans)的活性。
实施例2
漂洗、贮藏、重组酶片用的防腐溶液配方
制备本组方时，将三羟甲基甲基甘氨酸、尿囊素、肌醇、EDTA二钠和聚烃氧基-40-氢化蓖蔴油加入到80％体积的水中。溶液的pH用1N氢氧化钠调节至7.3。溶液的张力用氯化钠调节，同时加入聚亚己基双胍。然后将溶液用水稀释到既定体积。
  组分   供应商   ％重量/体积   加入量
  纯水   至80％   40ml
  三羟甲基甲基甘氨酸 Spectrum 1.0％ 0.500g
  尿囊素   Spectrum   0.25％   0.125g
  肌醇   Spectrum   0.1％   0.050g
  EDTA二钠   Spectrum   0.055％   0.0275g
  聚烃氧基-40-氢化蓖蔴油   BASF公司CremophorRH40 0.1％ 0.5ml(10％)
1N氢氧化钠   根据pH调节至7.3的需要   根据pH调节至7.3的需要
  纯水   至98％   稀释至49ml
氯化钠 Fisher   根据张力调节的需要285mOsm   根据张力调节的需要285mOsm
聚亚己基双胍盐酸盐   Avecia公司Cosmocil CQ(20％w/w溶液) 0.0001％ 50μl(0.1％)
  纯水   平衡至100％   稀释至50ml
本图表只是本发明的一个具体组方例子，并没有完全显示本发明的限制范围。
实施例3A专利：(氯化物少于0.1％，含糖类和乙二醇类)
本例是一个配方中含盐量低的溶液，缓冲溶液和阳离子型防腐剂如下所示：
  对数下降值 缓冲溶液 防腐剂   防腐增强剂 润湿剂
2.27 无   PHMB0.0001％ 无 无
3.85   Bis-tris propane0.2％   PHMB0.0001％ 无  CremophorRH40
4.40   Bis-tris propane0.2％   PHM0.0001％   丙二醇3％  CremophorRH40
4.40   Bis-tris propane0.2％   PHMB0.0001％   山梨糖醇5％  CremophorRH40
4.40   Bis-tris propane0.2％   PHMB0.0001％ 肌醇5％  CremophorRH40
2.98   Opti-FreeExpress
0.68   Ciba Solo-care
2.99   B&LRenuMultiplusMPS
表中第一栏显示的是将白色棒状杆菌(C.albicans)加入各种含有一种典型抗菌剂的溶液培养4小时后测试的对数下降值。数据显示出本发明溶液比使用单一防腐剂溶液的防腐效果更好；显示出本发明溶液比不加糖类添加剂的缓冲溶液对照样防腐效果更好；显示出本发明溶液比市售产品的防腐效果更好。
实施例3B
           糖类/乙二醇的防腐效能与盐浓度的关系
  对数下降值   缓冲溶液   防腐剂   添加剂
2.53 无   PHMB0.0001％ 无
1.34   Bis-Tris Propane0.2％   PHMB0.0001％ 氯化钠0.5％
3.42   Bis-Tris Propane0.2％   PHMB0.0001％ 甘油0.5％
2.73   Bis-Tris Propane0.2％   PHMB0.0001％ 丙二醇0.5％
1.13   Bis-Tris Propane0.2％   PHMB0.0001％ 氯化钾0.5％
3.92   Bis-Tris Propane0.2％   PHMB0.0001％ 山梨糖醇0.5％
3.23   Bis-Tris Propane0.2％   PHMB0.0001％ 甘露糖醇0.5％
3.06   Bis-Tris Propane0.2％   PHMB0.0001％ 肌醇0.5％
3.72   Bis-Tris Propane0.2％   PHMB0.0001％ 葡萄糖0.5％
这些数据显示：添加糖类或乙二醇后，缓冲溶液的抗菌活性比单独使用防腐剂要高；加入0.5％的氯化钠或氯化钾的溶液抗菌活性下降。这就表现出了糖类防腐增强剂的明显效果，以及显示与氯化物浓度的关系。
实施例3C
特别使用甘油的氯化物含量低于0.1％的溶液
制备出下表所示的含有阳离子型聚合物类防腐剂(PHMB)、氯化钠、甘油和缓冲试剂的溶液，并检测了其防腐效果：
  对数下降值 缓冲溶液 防腐剂 氯化钠 甘油
1.69 无   PHMB0.0001％ 无 无
1.74 无   PHMB0.0001％ 0.1％ 无
1.46 无   PHMB0.0001％ 0.2％ 无
0.86 无   PHMB0.0001％ 0.4％ 无
0.49 无   PHMB0.0001％ 0.5％ 无
2.44   Bis-Tris Propane0.2％   PHMB0.0001％ 无 无
1.89   Bis-Tris Propane0.2％   PHMB0.0001％ 0.1％ 无
1.54   Bis-TrisPropane 0.2％   PHMB0.0001％ 0.2％ 无
0.98   Bis-Tris Propane0.2％   PHMB0.0001％ 0.4％ 无
0.89   Bis-Tris Propane0.2％   PHMB0.0001％ 0.5％ 无
2.46   Bis-Tris Propane0.2％   PHMB0.0001％ 无 0.2％
2.41   Bis-Tris Propane0.2％   PHMB0.0001％ 无 0.5％
以上数据显示了氯化钠对溶液防腐性能的影响和低盐溶液中甘油增加溶液防腐性能的效果。
实施例3D
实验表明防腐剂效果抑制性依赖于缓冲溶液
根据以上描述的方法用磷酸钠盐作为缓冲剂制备出溶液：
  对数下降值   缓冲溶液   防腐剂   张力剂
0.79 磷酸钠盐0.2％   PHMB 0.0001％ 无
0.33 磷酸钠盐0.2％   PHMB 0.0001％ 氯化钠0.7％
这些数据表明氯化钠的问题不依赖于缓冲溶液类型。
实施例3E
组方中糖类对镜片的调节特性
用氯化钠、山梨糖醇和蔗糖配成溶液，将镜片浸入其中，并加入双氯苯双胍己烷葡糖酸脂。将镜片浸泡3小时，检测镜片上洗必泰的沉积量。
方法用高效液相色谱(HPLC)分析双氯苯双胍己烷葡糖酸(洗必泰，CHG)的含量；用3.0ml溶液浸泡镜片的1/2。
基质  1ppm CHG/0.2％Bis-Tris Propane/0.1％Cremophor RH40
镜片  Freshlook ColorBlends    (Wesley Jess)
  添加剂   μg CHG/镜片   减少量
  无   4.0   67.3％
  氯化钠   3.6   59.3％
  山梨糖醇   3.0   50.7％
  蔗糖   1.3   21.4％
水中含1ppm CHG；整个实验中RSD含量为2.9％。
这个实验表明在组方时适当地加入糖类能减少防腐剂，尤其是阳离子型防腐剂对镜片的附着程度，含山梨糖醇或蔗糖的溶液显示出能减少防腐剂的沉积。
实施例3F
下面的实验显示出氯化物浓度对含防腐剂PHMB的溶液抗微生物活性的影响
  对数下降值 缓冲溶液 防腐剂 NACL 添加剂 影响
1.05   Bis-Tris 0.2％   PHMB0.0001％ 无 无 54％
1.47   Bis-Tris0.5％   PHM0.0001％ 无 无 75％
0.77   Bis-Tris0.2％   PHMB0.0001％ 0.70％ 无 39％
  2.39   Bis-Tris   PHMB   无   无   123％
  Propane0.2％   0.0001％
2.32   Bis-TrisPropane0.5％ PHMB0.0001％ 无 无 119％
0.91   Bis-TrisPropane0.2％ PHMB0.0001％ 0.70％ 无 47％
1.27   Tricine0.2％   PHMB0.0001％ 无 无 65％
1.31   Tricine0.5％   PHMB0.0001％ 无 无 67％
0.62   Tricine0.2％   PHMB0.0001％ 0.70％ 无 32％

Claims (4)

1、一种隐形眼镜用溶液，其特征在于，含有0.1～5％重量比的防腐增强剂，所述防腐增强剂选自肌醇、甘露糖醇、蔗糖、葡萄糖、甘油和丙二醇；溶液中含有0.0001％重量比的阳离子型聚合物防腐剂，并且在所述溶液中氯化物的浓度低于0.2％重量比。
2、如权利要求1所述的隐形眼镜用溶液，其特征在于，进一步包含有缓冲试剂，这种缓冲试剂选自：磷酸盐、碳酸氢盐、柠檬酸盐、硼酸盐、N-(2-乙酰氨基)-2-氨基乙磺酸、N，N-双(2-羟乙基)-2-氨基乙磺酸、N，N-双(2-羟乙基)氨基乙酸、2，2-双(羟甲基)-2，2，2-次氨基三乙醇胺、1，3-双(三(羟甲基)甲氨基)丙烷、2-(4-(2-羟乙基)-1-哌嗪基)乙磺酸、N-(2-羟乙基)-哌嗪-N’-3-丙磺酸、咪唑、2-(N-吗啉)乙磺酸、3-(N-吗啉)丙磺酸、哌嗪-1，4-双(2-乙磺酸)、N-三(羟乙基)甲基-3-氨基丙磺酸、N-三(羟乙基)甲基-2-氨基乙磺酸和三羟甲基甲基甘氨酸。
3、如权利要求1所述的隐形眼镜用溶液，其特征在于，进一步包含有0.2～0.5％重量比的甘油。
4、如权利要求1所述的隐形眼镜用溶液，其特征在于，进一步包含有螯合剂，这种螯合剂为乙二胺四醋酸。
CNB018218172A 2000-11-08 2001-11-08 改进的含有单糖类作为防腐增强剂的眼科和隐形眼镜用溶液 Expired - Fee Related CN1245166C (zh)

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AU2006207883A1 (en) 2006-09-28
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US20060142169A1 (en) 2006-06-29
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AU2720602A (en) 2002-05-21
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AU2006207883B2 (en) 2009-08-06
PT1339418E (pt) 2009-10-30
ES2330617T3 (es) 2009-12-14
AU2002227206B2 (en) 2006-09-21
EP1339418A1 (en) 2003-09-03
ATE443749T1 (de) 2009-10-15
CN1486188A (zh) 2004-03-31
CY1111043T1 (el) 2015-06-11
US9492581B2 (en) 2016-11-15

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