CN1733789A - 阿奇霉素酒石酸盐的制备方法 - Google Patents
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Abstract
本发明公开了一种阿奇霉素酒石酸盐的制备方法：以低级(C1－C4)醇为溶剂、阿奇霉素单水合物或阿奇霉素二水合物与酒石酸在上述溶剂中进行反应，反应温度为0～70℃；反应结束后加入低级(C2－C6)酯进行沉淀，然后依次经过过滤、干燥。本发明还公开了另一种阿奇霉素酒石酸盐的制备方法：将低级(C1－C4)醇和低级(C2－C6)酯混合成复合溶媒，阿奇霉素单水合物或阿奇霉素二水合物与酒石酸在上述复合溶媒中进行反应，反应温度为0～70℃；反应结束后再依次经过过滤、干燥。本发明的制备方法，生产工艺简单、收率高、环境友好。
Description
技术领域
本发明涉及阿奇霉素(Azithromycin)酒石酸盐的制备方法。
背景技术
阿奇霉素是一种半合成的氮杂十五元环大环内酯类抗生素，其结构式如下：
与母体原料红霉素A相比，阿奇霉素具有对酸比较稳定、在机体组织中浓度高、作用持续时间长、抗菌谱广、副作用低等优点。然而和红霉素一样，它在水中的溶解度很小，无法直接制成注射剂及口服型可溶性粉。
1984年US4474468首次发明了阿奇霉素的水溶性盐—二盐酸盐。阿奇霉素和吡啶盐酸盐在二氯甲烷中进行反应，蒸发溶剂后，冷冻干燥，从水溶液中分离阿奇霉素二盐酸盐，但是此种方法收率很低、仅为54.4％。
1995年，CN95104228公开了阿奇霉素二盐酸盐的新制备方法。溶解在低级醇或低级酮中的阿奇霉素与溶解在干燥低级醇中的氯化氢气体反应，通过向反应混合物中加入非溶剂，从中沉淀产品。收率达98％。但该方法中涉及使用的原料——二异丙基醚不但危险性大且价格较高；另一种原料——氯化氢气体具有强酸性，在生产中较难控制，对整体设备要求较高；因此不适于大规模使用。
1995年，沈家祥发现，阿奇霉素与有机酸如谷氨酸、天冬氨酸、乳酸、酒石酸、枸椽酸、醋酸等成盐后，可增加其水溶液的溶解度。如专利CN1123279A所述，制备方法为由阿奇霉素与成盐化合物反应后，经精制、冻干或减压干燥或喷雾干燥后制得。反应溶媒通常为水；减压干燥时间长，容易产生降解；冻干或喷雾干燥需冻干机或喷雾干燥机。因此此种方法也不适于大规模使用。
发明内容
针对现有技术中存在的不足之处，本发明提供一种生产工艺简单、收率高、环境友好的阿奇霉素酒石酸盐的制备方法。
本发明为达到以上目的，是通过这样的技术方案来实现的：提供一种阿奇霉素酒石酸盐的制备方法，以低级(C1-C4)醇为溶剂、阿奇霉素单水合物或阿奇霉素二水合物与酒石酸在上述溶剂中进行反应，反应温度为0～70℃；阿奇霉素单水合物或阿奇霉素二水合物与酒石酸的摩尔比为1∶0.8～1.2；反应结束后加入低级(C2-C6)酯进行沉淀，然后依次经过过滤分离、干燥；低级(C1-C4)醇与低级(C2-C6)酯的体积比为1∶0.5～4。
作为本发明的阿奇霉素酒石酸盐制备方法的一种改进：阿奇霉素单水合物或阿奇霉素二水合物与酒石酸反应结束后，先加入活性炭吸附，过滤，得滤液，然后再向此滤液中加入低级(C2-C6)酯进行沉淀。
作为本发明的阿奇霉素酒石酸盐制备方法的进一步改进：低级醇是甲醇、乙醇、正丙醇、异丙醇、正丁醇、叔丁醇、异丁醇、或仲丁醇等；所述低沸点酯为甲酸甲酯、甲酸乙酯、乙酸甲酯、或乙酸乙酯。
本发明还提供了同一发明构思下的另一种阿奇霉素酒石酸盐的制备方法，将低级(C1-C4)醇和低级(C2-C6)酯混合成复合溶媒，低级(C1-C4)醇与低级(C2-C6)酯的体积比为1∶0.5～4；阿奇霉素单水合物或阿奇霉素二水合物与酒石酸在上述复合溶媒中进行反应，反应温度为0～70℃；阿奇霉素单水合物或阿奇霉素二水合物与酒石酸的摩尔比为1∶0.8～1.2；反应结束后再依次经过过滤分离、干燥。
作为本发明的阿奇霉素酒石酸盐制备方法的一种改进：低级醇是甲醇、乙醇、正丙醇、异丙醇、正丁醇、叔丁醇、异丁醇、或仲丁醇等；所述低沸点酯为甲酸甲酯、甲酸乙酯、乙酸甲酯、或乙酸乙酯。
本发明的上述两种阿奇霉素酒石酸盐制备方法，生产工艺简单、易于操作；由于没有使用强酸性气体作为原料，因此对生产设备没有特殊要求；生产环境友好，收率高，最高可达99.4％；易于大规模使用。
具体实施方式：
实施例1、阿奇霉素酒石酸盐的制备方法：向60ml无水乙醇中投入阿奇霉素二水合物31.2g，酒石酸6g(阿奇霉素二水合物与酒石酸的摩尔比为1∶1)，25℃搅拌反应一小时。反应结束后，投入活性炭1g，搅拌10分钟进行吸附；过滤，得滤液，向上述滤液中滴加入甲酸乙酯120ml，滴毕搅拌半小时，过滤，将滤得物在60℃减压干燥2小时，得到37.0g的阿奇霉素酒石酸盐，收率为99.4％，m.p.132-138℃。
实施例2、阿奇霉素酒石酸盐的制备方法：向60ml无水甲醇中投入阿奇霉素单水合物31.2g，酒石酸4.8(阿奇霉素二水合物与酒石酸的摩尔比为1∶0.8)，10℃搅拌反应一小时。反应结束后，投入活性炭1g，搅拌10分钟进行吸附，过滤，得滤液，向上述滤液中滴加入甲酸乙酯240ml，滴毕搅拌半小时，过滤，将滤得物在60℃减压干燥2小时，得到27.2g的阿奇霉素酒石酸盐，收率为73.0％，m.p.132-138℃。
实施例3、阿奇霉素酒石酸盐的制备方法：向60ml正丙醇中投入阿奇霉素二水合物31.2g，酒石酸7.2g(阿奇霉素二水合物与酒石酸的摩尔比为1∶1.2)，40℃搅拌反应一小时。反应结束后，投入活性炭1g，搅拌10分钟进行吸附，过滤，得滤液，向上述滤液中滴加入乙酸甲酯30ml，滴毕搅拌半小时，过滤，将滤得物在60℃减压干燥2小时，得到36.9g的阿奇霉素酒石酸盐，收率为99.2％，m.p.132-138℃。
实施例4、阿奇霉素酒石酸盐的制备方法：向60ml无水乙醇和240ml甲酸乙酯投入烧瓶，混合成复合溶媒；再向上述复合溶媒中投入阿奇霉素二水合物31.2g，酒石酸7.2g，15℃搅拌反应一小时。反应结束后，过滤，将滤得物在60℃减压干燥2小时，得到36.7g的阿奇霉素酒石酸盐，收率为98.7％，m.p.132-138℃。
实施例5：阿奇霉素酒石酸盐的制备方法：将60ml异丙醇和30ml乙酸乙酯投入烧瓶，混合成复合溶媒；再向上述复合溶媒中投入阿奇霉素单水合物31.2g，酒石酸6g，40℃搅拌反应一小时。反应结束后，过滤，滤得物在60℃减压干燥2小时。得到33.4g阿奇霉素酒石酸盐，收率为89.8％，m.p.132-138℃。
实施例6：阿奇霉素酒石酸盐的制备方法：将50ml无水乙醇和60ml乙酸甲酯投入烧瓶，混合成复合溶媒；再向上述复合溶媒中投入阿奇霉素二水合物31.2g，酒石酸4.8g，25℃搅拌反应一小时。反应结束后，过滤，滤得物在60℃减压干燥2小时。得到28.5g阿奇霉素酒石酸盐，收率为76.6％，m.p.132-138℃。
最后，还需要注意的是，以上列举的仅是本发明的若干个具体实施例。显然，本发明不限于以上实施例，还可以有许多变形。本领域的普通技术人员能从本发明公开的内容直接导出或联想到的所有变形，均应认为是本发明的保护范围。
Claims (5)
1、一种阿奇霉素酒石酸盐的制备方法，其特征是：以低级(C1-C4)醇为溶剂、阿奇霉素单水合物或阿奇霉素二水合物与酒石酸在所述溶剂中进行反应，反应温度为0～70℃；所述阿奇霉素单水合物或阿奇霉素二水合物与酒石酸的摩尔比为1∶0.8～1.2；反应结束后加入低级(C2-C6)酯进行沉淀，然后依次经过过滤、干燥；所述低级(C1-C4)醇与低级(C2-C6)酯的体积比为1∶0.5～4。
2、根据权利要求1所述的阿奇霉素酒石酸盐的制备方法，其特征是：所述阿奇霉素单水合物或阿奇霉素二水合物与酒石酸反应结束后，先加入活性炭吸附，过滤，得滤液，然后再向所述滤液中加入低级(C2-C6)酯进行沉淀。
3、根据权利要求1或2所述的阿奇霉素酒石酸盐的制备方法，其特征是：所述低级(C1-C4)醇是甲醇、乙醇、正丙醇、异丙醇、正丁醇、叔丁醇、异丁醇、或仲丁醇；所述低级(C2-C6)酯为甲酸甲酯、甲酸乙酯、乙酸甲酯、或乙酸乙酯。
4、一种阿奇霉素酒石酸盐的制备方法，其特征是：将低级(C1-C4)醇和低级(C2-C6)酯混合成复合溶媒，所述低级(C1-C4)醇与低级(C2-C6)酯的体积比为1∶0.2～4；阿奇霉素单水合物或阿奇霉素二水合物与酒石酸在所述复合溶媒中进行反应，反应温度为0～70℃；所述阿奇霉素单水合物或阿奇霉素二水合物与酒石酸的摩尔比为1∶0.8～1.2；反应结束后再依次经过过滤、干燥。
5、根据权利要求5所述的阿奇霉素酒石酸盐的制备方法，其特征是：所述低级(C1-C4)醇是甲醇、乙醇、正丙醇、异丙醇、正丁醇、叔丁醇、异丁醇、或仲丁醇；所述低级(C2-C6)酯为甲酸甲酯、甲酸乙酯、乙酸甲酯、或乙酸乙酯。
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| CN101092440B (zh) * | 2007-07-19 | 2010-05-26 | 浙江尖峰药业有限公司 | 硫酸阿奇霉素的制备方法 |
| CN101412740B (zh) * | 2007-10-18 | 2012-12-19 | 刘力 | 阿奇霉素盐的水合物及其制备和用途 |
| CN103462910A (zh) * | 2013-09-22 | 2013-12-25 | 悦康药业集团有限公司 | 一种注射用阿奇霉素组合物及其制备方法 |
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| HRP940251B1 (en) * | 1994-04-15 | 1998-12-31 | Stjepan Mutak | Process for the preparation of azithromycin dihydrochloride |
| CN1123279A (zh) * | 1995-06-15 | 1996-05-29 | 沈家祥 | 阿奇霉素水溶性盐、其注射剂型以及它们的用途 |
| CN1344541A (zh) * | 2001-08-04 | 2002-04-17 | 安徽省新药研究院 | 阿奇霉素水溶性盐及其滴眼剂 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101092440B (zh) * | 2007-07-19 | 2010-05-26 | 浙江尖峰药业有限公司 | 硫酸阿奇霉素的制备方法 |
| CN101412740B (zh) * | 2007-10-18 | 2012-12-19 | 刘力 | 阿奇霉素盐的水合物及其制备和用途 |
| CN103462910A (zh) * | 2013-09-22 | 2013-12-25 | 悦康药业集团有限公司 | 一种注射用阿奇霉素组合物及其制备方法 |
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