Methanesulfonic acid salt forms of carbamazepine and 10,11-dihydrocarbamazepine.

IF 0.8 4区化学

Acta crystallographica. Section C, Crystal structure communications Pub Date : 2013-11-01 Epub Date: 2013-10-31 DOI:10.1107/S010827011302859X

Alex R Eberlin, Mark D Eddleston, Christopher S Frampton

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引用次数: 6

Abstract

New methanesulfonic acid salt forms of the anticonvulsant and analgesic active pharmaceutical ingredient carbamazepine and its closely related structural analogue 10,11-dihydrocarbamazepine have been prepared and characterized by single-crystal X-ray diffraction at 120 and 100 K, respectively {namely [(5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium methanesulfonate, C15H13N2O(+)·CH3SO3(-), and [(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium methanesulfonate, C15H15N2O(+)·CH3SO3(-)}. In light of the structural information obtained, the crystal structure of the carbamazepine trifluoroacetic acid monosolvate [dibenzo[b,f]azepine-5-carboxamide-trifluoroacetic acid (1/1), C15H12N2O·CF3COOH] was redetermined at 100 and 270 K, and from this data it was concluded that the protonation state for this solvate species is best described as in an `intermediate state' with the acidic proton located almost at the mid-point between the acid and base.

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卡马西平和10,11-二氢卡马西平的甲磺酸盐形式。

制备了抗痉挛镇痛活性药物卡马西平及其密切相关的结构类似物10,11-二氢卡马西平的新型甲磺酸盐形式，并在120和100 K下用单晶x射线衍射对其进行了表征，分别为[(5h -二苯并[b,f]azepin-5-基)(羟基)亚甲基]氮唑甲磺酸盐、C15H13N2O(+)·CH3SO3(-)和[(10,11-二氢并[b,f]azepin-5-基)(羟基)亚甲基]氮唑甲磺酸盐。C15H15N2O·CH3SO3(+)(-)}。根据所获得的结构信息，在100和270 K下重新测定了卡马西平三氟乙酸单溶剂[二苯并[b,f]氮平-5-羧酰胺-三氟乙酸(1/1)，C15H12N2O·CF3COOH]的晶体结构，并从该数据得出结论，该溶剂化物的质子化状态最好描述为“中间状态”，酸性质子几乎位于酸碱之间的中点。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Acta crystallographica. Section C, Crystal structure communications 化学-晶体学

自引率

12.50%

发文量

审稿时长

1 months

期刊介绍： Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.