CN1124352C - 寡糖补给组合物 - Google Patents
寡糖补给组合物 Download PDFInfo
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- CN1124352C CN1124352C CN00809477A CN00809477A CN1124352C CN 1124352 C CN1124352 C CN 1124352C CN 00809477 A CN00809477 A CN 00809477A CN 00809477 A CN00809477 A CN 00809477A CN 1124352 C CN1124352 C CN 1124352C
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- oligosaccharides
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- oligosaccharide
- oligomeric
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Abstract
发泡性可咀嚼片剂形式的寡糖补给组合物，其特征在于含有10-80重量%寡糖，0.3-10重量%发泡剂成分和0.9-30重量%中和剂成分。这些组合物实用性很高、制剂均匀、口感优良、具有制剂稳定性并且易于服用。
Description
技术领域
本发明涉及一种寡糖补给组合物，更具体地说，涉及一种具有高含量寡糖的寡糖补给组合物，其具有改进的口感和高度的稳定性，并且是发泡性可咀嚼片剂形式。
背景技术
已知寡糖具有低的可消化性，其通常是以未消化的状态到达大肠并被肠细菌利用。也已知寡糖平衡肠内环境，并对增加双歧乳杆菌水平特别有效。为取得这些效果，尽管根据寡糖的类型其摄入量可以稍微有所不同，但寡糖的最低需要的摄入量通常为每天0.7-10g。
大多数的寡糖为非晶体，并且是多种碳水化合物的混合物。因此，寡糖的吸湿性大约比蔗糖高数倍。因此，也已知高含量寡糖的组合物具有较差的口感和较低的稳定性。
可购得的寡糖一般为粉末或糖浆形式。很少直接食用这些可购得形式的寡糖，通常是将寡糖制成合适的制剂如粉剂、片剂(可咀嚼)等。但是，这些寡糖制剂的缺点是在摄取时粘到牙齿上。另一个缺点是由于寡糖具有高吸湿性，它们会较快地形成固体块状物。考虑到口感和稳定性，大多数含有寡糖的制剂被制成不存在上述问题的饮料。
因此，已知的含有寡糖的制剂通常不适合以足以产生其平衡肠内环境的内在效果的量摄取或给用。其制剂形式、口感、稳定性和摄取和给用的简易性等方面仍然需要改进。
本发明的公开
本发明的一个目的是提供一种改进的、能够取代传统含寡糖制剂的寡糖补给制剂，其实用性很高，在制剂中组分的分布很均匀，具有优良的口感和更高的稳定性，且能够容易地服用。
为达到上述目的，本发明人进行了广泛的研究并发现：发泡性可咀嚼的片剂在摄取或给用过程中容易崩解，且在口中的溶解性很好，因而能够避免在咀嚼制剂过程中粘到牙齿上，因此提供了一种无不良口感的改进的寡糖补给制剂，并可以使人在不需要的情况下通过舔食或咀嚼而享受它的味道。根据这些发现完成了本发明。
本发明提供一种含有10-80重量％寡糖、0.3-10重量％发泡剂成分和0.9-30重量％中和剂成分的寡糖补给组合物，该组合物是发泡的可咀嚼片剂形式。
本发明提供的上述寡糖补给组合物还含有0.1-5重量％碳酸钾作为稳定剂；上述组合物还含有5-20重量％水不溶性膳食纤维；上述组合物其中的寡糖为乳蔗糖；上述组合物其中寡糖的含量为30-75重量％；上述组合物其中的寡糖为选自由下列寡糖组成的组中的至少一种：乳蔗糖、低聚帕拉金糖(palatinose)、低聚异麦芽糖、低聚木糖、低聚果糖、乳果糖、低聚半乳糖、低聚龙胆糖、几丁质寡糖、大豆寡糖、6-α-葡糖基麦芽糖、纤维寡糖、果胶寡糖、低聚菊糖、低聚果聚糖、低聚甘露糖、低聚壳糖和偶合糖；上述组合物其中寡糖为选自由下列寡糖组成的组中的至少一种：乳蔗糖、低聚帕拉金糖、低聚异麦芽糖、低聚木糖、低聚果糖、乳果糖、低聚半乳糖和大豆寡糖；上述组合物其中的寡糖为乳蔗糖；上述组合物其中的发泡剂成分为选自由下列发泡剂组成的组中的至少一种：碳酸氢钠、碳酸钠和碳酸钙；上述组合物其中的中和剂成分为选自由下列中和剂组成的组中的至少一种：柠檬酸、L-酒石酸、L-抗坏血酸和DL-苹果酸；上述组合物其中的中和剂成分为选自由下列中和剂组成的组中的至少一种：L-抗坏血酸和无水柠檬酸；上述组合物其中的水不溶性膳食纤维为选自由下列膳食纤维组成的组中的至少一种：结晶纤维素、麦麸、燕麦麸、球果纤维、大豆纤维和甜菜纤维；上述组合物其中的水不溶性膳食纤维为结晶纤维素。
本发明组合物的发泡性可咀嚼片剂在口中以中等速度崩解并溶解，这样就避免了由于寡糖固有的吸湿性而引起的粘结，即在口中粘到牙齿上，因此使人在不需要水的情况下通过舔食或咀嚼片剂而享受它的味道，并同时通过摄取实现寡糖充分的补给及在体内的吸收。
还包含指定量碳酸钾作为稳定剂的本发明组合物能够避免在摄取该组合物之前中和剂与发泡剂之间不必要的反应(由于水的存在而引起)，并能够确保在摄取过程中足够的发泡反应。也就是说，碳酸钾充当干燥剂。
还包含指定量水不溶性膳食纤维的本发明组合物的优点是即使显著增加寡糖的含量也不会对组合物的口感和稳定性产生明显的不利影响。
还包含蔗糖脂肪酸酯、糖粉、果汁粉末和香料的本发明组合物其片剂的形状保持性得到进一步改进，且具有更好的味道。
在本发明中使用寡糖是必要的。优选使用的寡糖为增加双歧乳杆菌水平的寡糖。但是，对可用的寡糖并没有限制，所有的具有吸湿性，并且含有该寡糖的制剂存在粘到牙齿上的问题的寡糖都可以使用。此处使用的术语“增加双歧乳杆菌水平的寡糖”定义为双歧乳杆菌的肠内生长必需和重要作用的营养物(糖源)，并由2-10个实质上不被人体消化酶消化并不被人体吸收或除双歧乳杆菌外不被肠细菌利用(即被双歧乳杆菌选择性利用)的单糖组成的寡糖。有一些已知的寡糖可以用于本发明。具体例子包括乳蔗糖、低聚帕拉金糖、低聚异麦芽糖、低聚木糖、低聚果糖、乳果糖、低聚半乳糖、低聚龙胆糖、几丁质寡糖、大豆寡糖、6-α-葡糖基麦芽糖、纤维寡糖、果胶寡糖、低聚菊糖、低聚果聚糖、低聚甘露糖、低聚壳糖、偶合糖等等。其中优选的为乳蔗糖、低聚帕拉金糖、低聚异麦芽糖、低聚木糖、低聚果糖、乳果糖、低聚半乳糖和大豆寡糖。特别优选的为乳蔗糖。这些寡糖可以两种或多种的混合物使用。
一般来讲，可购得的寡糖主要为天然副产物、用酶水解多糖所得的水解产物、由糖类与酶的转移和缩合反应的聚合产物、糖类的异构化和还原产物等等。可购得的寡糖可能含有未反应的产物或反应的副产物。在本发明中，以这样的混合物形式方便地利用寡糖，即可购得的寡糖形式。
以下描述寡糖混合物的制备方法和组合物的例子。
例如，含乳蔗糖的混合物可以通过乳糖和蔗糖的酶反应获得。该混合物含有55重量％或以上的乳蔗糖作为主要成分，并且还含有乳糖等。
含有低聚帕拉金糖的混合物可以通过将通过蔗糖的酶反应获得的帕拉金糖的部分缩合获得。该混合物含有45重量％或以上的低聚帕拉金糖作为主要成分，并且还含有帕拉金糖等等。
含有低聚异麦芽糖的混合物可以通过淀粉的酶处理获得。该混合物含有85重量％或以上的低聚异麦芽糖，并且还含有葡萄糖、麦芽糖等等。
含有低聚木糖的混合物可以通过植物纤维(木聚糖)如棉籽壳的酶处理获得。该混合物含有95重量％或以上的低聚木糖作为主要成分。
含有低聚果糖的混合物可以通过蔗糖的酶处理获得。该混合物含有95重量％或以上的低聚果糖作为主要成分，并且还含有蔗糖等等。
含有乳果糖的混合物可以通过乳糖的异构化获得。该混合物含有97重量％或以上的乳果糖作为主要成分，并且还含有半乳糖等等。
含有低聚半乳糖的混合物可以通过乳糖的酶处理获得。该混合物含有55-70重量％或以上的低聚半乳糖作为主要成分，并且还含有乳糖等等。
含有大豆寡糖的混合物可以通过从大豆中分离出含蔗糖的成分并精制获得。该混合物含有10重量％以上的水苏糖和棉子糖。
优选在本发明组合物中寡糖的比例为10-80重量％，更优选30-75重量％。如果该比例低于10重量％，则每片可咀嚼的片剂中寡糖的含量太低，导致难以取得其双歧杆菌的增殖效果从而失去商业价值，因此是不利的。另一方面，如果该比例高于80重量％，则寡糖以外的成分的比例就要下降。例如，发泡剂成分和中和剂成分的量下降将不会产生所期望的发泡性能，并且不能提供口感改进的可咀嚼的片剂，因此也是不利的。
除寡糖之外，本发明的组合物还必须含有指定量的发泡剂成分和中和剂成分。所使用的发泡剂成分可以选自碳酸氢钾、碳酸氢钠、碳酸钠、碳酸镁和碳酸钙，更优选选自碳酸氢钠、碳酸钠和碳酸钙。这些发泡剂可以单独使用或二种或多种结合使用。
所使用的中和剂成分为能够中和发泡剂成分而产生二氧化碳气体的酸性化合物。该酸性化合物的具体例子包括有机酸，如柠檬酸、L-酒石酸、富马酸、L-抗坏血酸、葡萄糖酸、乙酸、乳酸、DL-苹果酸等等。优选柠檬酸(无水柠檬酸)、L-酒石酸、L-抗坏血酸和DL-苹果酸。特别优选L-抗坏血酸和无水柠檬酸。
本发明组合物中发泡成分的比例优选为0.3-10重量％，中和剂成分的比例优选为0.9-30重量％。如果组合物含有低于0.3重量％的发泡剂，则所得到的可咀嚼的片剂将不会很好地崩解，因此无法取得所期望的粘着抑制效果。另一方面，如果发泡剂的比例高于10重量％，则所得到的可咀嚼的片剂倾向于产生过多的泡沫，食用时味道不好。如果该组合物含有低于0.9重量％的中和剂，则发泡剂成分将不能被充分中和，导致发泡性不好，不能取得所期望的粘着抑制效果，并且酸味不充分。另一方面，如果中和剂的比例高于30重量％，则导致所得到的可咀嚼的片剂过酸，味道不好。特别优选的发泡剂比例为大约0.6-大约3重量％，中和剂为大约2-大约10重量％。
本发明组合物更有利的方面在于其含有0.1-5重量％碳酸钾作为稳定剂。此比例范围的碳酸钾不会对组合物的味道产生不利影响，并能有效保持本发明组合物的发泡性能。
优选本发明组合物进一步含有5-20重量％水不溶性膳食纤维。在此，“水不溶性膳食纤维”在此指难以消化并不能被人体消化酶水解的水不溶性食用物质。其具体例子包括结晶纤维素、麦麸、燕麦麸、圆锥纤维(cone fiber)、大豆纤维和甜菜纤维。这些水不溶性的膳食纤维可以单独使用或两种或多种结合使用。结合使用是有利的，因为用低价物质部分取代高价物质，可以降低成本。这些水不溶性膳食纤维能够增强在摄取过程中所期望的本组合物在牙齿上的粘着抑制效果。但是，水不溶性膳食纤维在口中不能完全溶解。因此，如果该水不溶性膳食纤维的比例超过20重量％过多，将导致粉末口感。因此，大量的水不溶性膳食纤维是不理想的。
除必须成分外，本发明组合物可以选择性地含有选自各种已知添加剂的添加成分。这样的添加剂包括，例如糖类(不包括寡糖)、糖醇、甜味剂和类似的赋形剂、粘合剂、崩解剂、润滑剂、增稠剂、表面活性剂、电解质、香料、着色剂、pH调节剂、流动性改进剂等等。这些添加剂的具体例子包括小麦淀粉、土豆淀粉、玉米淀粉、糊精等淀粉类；蔗糖、葡萄糖、果糖、麦芽糖、木糖、乳糖等糖类(不包括寡糖)；山梨醇、甘露醇、麦芽糖醇、木糖醇等糖醇类；磷酸钙、硫酸钙等赋形剂；淀粉、糖、明胶、阿拉伯树胶、糊精、甲基纤维素、聚乙烯吡啶烷酮、聚乙烯醇、羟丙基纤维素、黄原胶、果胶、黄芪胶、酪蛋白、褐藻酸等粘合剂和增稠剂；亮氨酸、异亮氨酸、L-缬氨酸、糖酯、硬化油、硬脂酸、硬脂酸镁、滑石粉、聚乙二醇等润滑剂；CMC、CMC-Na、CMC-Ca等崩解剂；聚山梨醇酯、卵磷脂等表面活性剂；天冬甜素、天胺糖精等二肽；二氧化硅等流动性改进剂；和甜菊苷、糖精等甜味剂。根据这些添加剂与制剂必要成分的关系和制剂的性能、制造方法等适当地选择其用量。
本发明制剂可以进一步含有适量的维生素。此类的维生素包括上述用作中和剂的L-抗坏血酸(维生素C)。
本发明组合物可以按照常规的制剂制造方法制造。例如，本发明制剂的发泡性片剂可以通过称量并混合指定量的成分，并把该混合物通过直接粉末压缩法、干式或湿式颗粒压缩法等进行制造。
所得到的本发明的发泡性可咀嚼片剂是口服的。优选摄取量为若干片本发明的可咀嚼片剂，每片重约0.5-6g。
与已知的可咀嚼片剂一样，本发明的组合物形成适于在口中咀嚼或适于用水送服的形状。
本发明提供一种发泡性可咀嚼片剂形式的新型寡糖补给组合物。该发泡性可咀嚼片剂具有优良的储存稳定性、在口中容易崩解、并可容易地摄取或给用，因此是有利的。本发明组合物的另一个有利的特点是通过摄取，实现寡糖充分、安全的补给和在体内的吸收，这样该寡糖能够调节肠的功能。本发明组合物还有一个特性是味道很好，并具有清凉和柔和的味道。
实施本发明的最佳方式
以下给出的实施例更详细地说明本发明。在实施例中，如无特别指定，份数和百分比均为重量份和重量百分比。
实施例1-21
将按照下表1-4中指定量的寡糖、其它糖和水不溶性膳食纤维置于搅拌混合机(Mitsui Henshell Mixer FM20C/I，三井矿山有限公司(Mitsui Mining Company，Limited)制造)中并混合。向以上混合物中加入若干百分比的水与乙醇的混合液，并将所获得的混合物以湿法造粒。
使用真空干燥炉(Tabai Espec公司制造)将如此获得的颗粒真空干燥。将颗粒过16号筛。然后加入指定量的中和剂、发泡剂、果汁粉、碳酸钾和香料和用作润滑剂的蔗糖脂肪酸酯并混合。使用旋转式压锭机(RT-S20-25K-A，菊水电子公司(Kikusui Electronics Corp.)制造)将该混合物压锭，得到本发明寡糖补给组合物的发泡性可咀嚼片剂。
表1
| 成分(重量％) | 实 施 例 编 号 | |||||
| 1 | 2 | 3 | 4 | 5 | 6 | |
| 寡糖低聚异麦芽糖低聚半乳糖低聚果糖低聚帕拉金糖 | 6656--- | 7060--- | 63-44-- | 56--39- | 70--67- | 71---32 |
| 中和剂成分L-抗坏血酸无水柠檬酸 | 5- | -3 | 22 | 22 | 4- | 4- |
| 发泡剂成分碳酸氢钠碳酸钠碳酸钙 | 2-- | 1-- | 11- | 1-- | 1-- | 1-2 |
| 蔗糖脂肪酸酯 | 1 | 1 | 2 | 1 | 1 | 1 |
| 糖粉 | 7 | 2 | 5 | 18 | - | - |
| 水不溶性膳食纤维结晶纤维素 | 13 | 18 | 20 | 15 | 20 | 16 |
| 果汁粉 | 3 | 3 | 2 | 3 | 2 | 3 |
| 碳酸钾 | 0.5 | 0.2 | 0.3 | 0.2 | 0.2 | 0.2 |
| 香料 | 适量 | 适量 | 适量 | 适量 | 适量 | 适量 |
| 总重量(g) | 2.7 | 2.8 | 2.8 | 2.7 | 2.9 | 3.1 |
表2
| 成分(重量％) | 实 施 例 编 号 | |||||
| 7 | 8 | 9 | 10 | 11 | 12 | |
| 寡糖乳果糖乳蔗糖低聚木糖大豆寡糖 | 6658--- | 4948--- | 69-38-- | 64-35-- | 38--36- | 77---10 |
| 中和剂成分L-抗坏血酸无水柠檬酸 | 31 | 22 | 22 | 31 | 41 | 21 |
| 发泡剂成分碳酸氢钠碳酸钠碳酸钙 | 1-- | 11- | 2-- | 1-- | 2-- | 1-- |
| 蔗糖脂肪酸酯 | 1 | 1 | 1 | 1 | 1 | 1 |
| 糖粉 | 15 | 18 | 9 | 12 | 30 | 3 |
| 水不溶性膳食纤维结晶纤维素 | 14 | 19 | 10 | 10 | 17 | 7 |
| 果汁粉 | 3 | 5 | 3 | 6 | 5 | 6 |
| 碳酸钾 | 0.2 | 0.2 | 0.3 | 0.2 | 0.3 | 0.2 |
| 香料 | 适量 | 适量 | 适量 | 适量 | 适量 | 适量 |
| 总重量(g) | 3.0 | 3.1 | 2.9 | 2.8 | 2.8 | 2.9 |
表3
| 成分(重量％) | 实 施 例 编 号 | |||||
| 13 | 14 | 15 | 16 | 17 | 18 | |
| 寡糖低聚异麦芽糖低聚半乳糖低聚果糖低聚帕拉金糖乳果糖乳蔗糖 | 4236----- | 35-25---- | 57--54--- | 72---32-- | 30----29- | 70-----39 |
| 中和剂成分L-抗坏血酸无水柠檬酸 | 8- | -5 | 12- | 63 | 76 | 31 |
| 发泡剂成分碳酸氢钠碳酸钠 | 4- | 31 | 7- | 5- | 10- | 2- |
| 蔗糖脂肪酸酯 | - | - | - | 3 | - | 2 |
| 糖粉 | 30 | 42 | 8 | 5 | 26 | 12 |
| 水不溶性膳食纤维结晶纤维素 | 15 | 13 | 15 | 5 | 20 | 9 |
| 碳酸钾 | 0.5 | 0.4 | 0.6 | 0.5 | 0.4 | 0.1 |
| 香料 | 适量 | 适量 | 适量 | 适量 | 适量 | 适量 |
| 总重量(g) | 2.7 | 3.0 | 2.9 | 2.5 | 2.3 | 2.6 |
表4
试验例1口感试验
| 成分(重量％) | 实施例编号 | ||
| 19 | 20 | 21 | |
| 寡糖乳果糖乳蔗糖 | 8078- | 4342- | 80-44 |
| 中和剂成分L-抗坏血酸无水柠檬酸 | -0.9 | 30- | 0.9- |
| 发泡剂成分碳酸氢钠碳酸钠 | 0.3- | 7- | 0.3- |
| 水不溶性膳食纤维结晶纤维素 | 19 | 20 | 19 |
| 总重量(g) | 3.0 | 3.0 | 2.7 |
以与上述实施例类似的方式制备具有下表5中所示的组分的本发明制剂。以类似的方式制备不含有发泡剂成分的片剂作为对比制剂。由10名试验小组成员进行比较试验，以评价这些样品在口腔中的口感。
依据以下标准进行评价，结果示于表5。
1…不粘着到牙齿上
2…轻微粘着到牙齿上
3…粘着到牙齿上
表5
试验例2口感试验
| 本发明组合物 | 比较组合物 | |
| 成分(mg)乳蔗糖L-抗坏血酸碳酸氢钠 | 2000430200 | 2000 |
| 总重量 | 2630 | 2000 |
| 口感评价(人数)1 | 7 | 0 |
| 2 | 3 | 3 |
| 3 | 0 | 7 |
| 综合评价 | 不粘着到牙齿上 | 粘着到牙齿上 |
以与上述实施例类似的方式制备具有下表6中所示的组分的本发明制剂。以类似的方式制备不含有发泡剂成分的片剂作为对比制剂。由10名试验小组成员进行比较试验，以评价这些样品在口腔中的口感。
以与试验例1同样的方式进行评价，结果示于表6。
表6
| 本发明组合物 | 比较组合物 | |
| 成分(mg)低聚异麦芽糖蔗糖脂肪酸酯结晶纤维素L-抗坏血酸碳酸氢钠碳酸钾总重量 | 1500404001203032093 | 15004040060--2000 |
| 口感评价(人数)1 | 8 | 0 |
| 2 | 2 | 4 |
| 3 | 0 | 6 |
| 综合评价 | 不粘着到牙齿上 | 粘着到牙齿上 |
工业实用性
本发明提供一种发泡性可咀嚼片剂形式的寡糖补给制剂，其实用性高、组成均匀、口感优良、稳定性高，并且易于摄取或给用。
Claims (13)
1.一种发泡性可咀嚼片剂形式的寡糖补给组合物，其含有10-80重量％寡糖，0.3-10重量％发泡剂成分和0.9-30重量％中和剂成分。
2.根据权利要求1的组合物，其还含有0.1-5重量％碳酸钾作为稳定剂。
3.根据权利要求1或2的组合物，其还含有5-20重量％水不溶性膳食纤维。
4.根据权利要求1-3任一项的组合物，其中寡糖为乳蔗糖。
5.根据权利要求1的组合物，其寡糖含量为30-75重量％。
6.根据权利要求1的组合物，其中寡糖为选自由下列寡糖组成的组中的至少一种：乳蔗糖、低聚帕拉金糖、低聚异麦芽糖、低聚木糖、低聚果糖、乳果糖、低聚半乳糖、低聚龙胆糖、几丁质寡糖、大豆寡糖、6-α-葡糖基麦芽糖、纤维寡糖、果胶寡糖、低聚菊糖、低聚果聚糖、低聚甘露糖、低聚壳糖和偶合糖。
7.根据权利要求1的组合物，其中寡糖为选自由下列寡糖组成的组中的至少一种：乳蔗糖、低聚帕拉金糖、低聚异麦芽糖、低聚木糖、低聚果糖、乳果糖、低聚半乳糖和大豆寡糖。
8.根据权利要求1的组合物，其中发泡剂成分为选自由下列发泡剂组成的组中的至少一种：碳酸氢钠、碳酸钠和碳酸钙。
9.根据权利要求1的组合物，其中中和剂成分为选自由下列中和剂组成的组中的至少一种：柠檬酸、L-酒石酸、L-抗坏血酸和DL-苹果酸。
10.根据权利要求1的组合物，其中中和剂成分为选自由下列中和剂组成的组中的至少一种：L-抗坏血酸和无水柠檬酸。
11.根据权利要求1的组合物，其中水不溶性膳食纤维为选自由下列膳食纤维组成的组中的至少一种：结晶纤维素、麦麸、燕麦麸、圆锥纤维、大豆纤维和甜菜纤维。
12.根据权利要求1的组合物，其中水不溶性膳食纤维为结晶纤维素。
13.一种改进寡糖补给制剂的口感的方法，该方法避免在摄取过程中寡糖补给制剂粘着到牙齿上，该方法包括将0.3-10重量％发泡剂成分和0.9-30重量％中和剂成分与10-80重量％寡糖混合，并将该组合物制成发泡性可咀嚼片剂。
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| CA3111795A1 (en) | 2018-09-05 | 2020-03-12 | Solarea Bio, Inc. | Methods and compositions for treating musculoskeletal diseases |
| US11980647B2 (en) | 2018-09-05 | 2024-05-14 | Solarea Bio, Inc. | Methods and compositions for treating musculoskeletal diseases, treating inflammation, and managing symptoms of menopause |
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Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU634746B2 (en) * | 1989-02-07 | 1993-03-04 | Dimminaco Ag/Sa/Ltd. | Effervescent composition for oral rehydration |
| HU217125B (hu) * | 1993-03-10 | 1999-11-29 | Béres Rt. | Cukor- és nátriummentes pezsgőtabletta és -granulátum és eljárás azok előállítására |
| FR2726469B1 (fr) * | 1994-11-08 | 1996-12-13 | Adir | Composition pharmaceutique pour l'administration orale de flavonoides |
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1999
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2000
- 2000-06-20 CN CN00809477A patent/CN1124352C/zh not_active Expired - Fee Related
- 2000-06-20 US US10/019,197 patent/US6750331B1/en not_active Expired - Fee Related
- 2000-06-20 KR KR1020017016684A patent/KR100615507B1/ko not_active IP Right Cessation
- 2000-06-20 WO PCT/JP2000/003998 patent/WO2001000883A1/ja active IP Right Grant
- 2000-06-27 TW TW089112591A patent/TW548080B/zh not_active IP Right Cessation
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| US6750331B1 (en) | 2004-06-15 |
| WO2001000883A1 (fr) | 2001-01-04 |
| KR20020015706A (ko) | 2002-02-28 |
| JP2001008666A (ja) | 2001-01-16 |
| KR100615507B1 (ko) | 2006-08-25 |
| CN1358233A (zh) | 2002-07-10 |
| JP4273277B2 (ja) | 2009-06-03 |
| TW548080B (en) | 2003-08-21 |
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