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Synthesis and structure determination of new pharmaceutical cocrystals

Al-Abachi, Anas Mouayed (2016)
M.Phil. thesis, University of Birmingham.

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Abstract

Pharmaceutical cocrystals have an important and influential role in the pharmaceutical industry through the formation of substitutional crystalline material to obtain the optimum physical properties of an active pharmaceutical ingredient (API) without changing its chemical properties. Pyrazinamide is anti-bacterial drug which is used to treat tuberculosis that infects the lung tissues. In this thesis, the ability of pyrazinamide to form co-crystals with different di-carboxylic acids through the formation of strong hydrogen bonds to form motifs is investigated.

Pyrazinamide cocrystals were synthesised through different methods using a variety of different solvents and different starting stoichiometric ratios. New cocrystals were formed between pyrazinamide and glutaric acid (1:1), pyrazinamide and adipic acid (4:1), pyrazinamide and pimelic acid (1:1), and pyrazinamide and sebacic acid (2:1). In all cases, X-ray powder diffraction and NMR were used to characterise the new material formed with the crystal structures of these materials determined through single crystal X-ray diffraction. The crystal structure of a polymorph of azelaic acid was also determined through single crystal X-ray diffraction analysis following attempted synthesis of a pyrazinamide:azelaic acid cocrystal.

Other new products were characterised through X-ray powder diffraction, although further structural analysis was not carried out. These include adducts based on pyrazinamide:oxalic acid, pyrazinamide:malonic acid, pyrazinamide:maleic acid, pyrazinamide:isonicotinamide, nicotinamide:isonicotinamide and isonicotinamide:fumaric acid. Attempts to prepare adducts between pyrazinamide with histidine and nicotinamide only resulted in a mixture, as did the combination of L-dopamaine with succinic acid.

Type of Work:M.Phil. thesis.
Supervisor(s):Tremayne, Mary-Jane
School/Faculty:Colleges (2008 onwards) > College of Engineering & Physical Sciences
Department:School of Chemistry
Subjects:QD Chemistry
Institution:University of Birmingham
ID Code:6930
This unpublished thesis/dissertation is copyright of the author and/or third parties. The intellectual property rights of the author or third parties in respect of this work are as defined by The Copyright Designs and Patents Act 1988 or as modified by any successor legislation. Any use made of information contained in this thesis/dissertation must be in accordance with that legislation and must be properly acknowledged. Further distribution or reproduction in any format is prohibited without the permission of the copyright holder.
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