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Development of a new synthesis approach for S-pregabalin by optimizing the preparation stages

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Abstract

In the present study, we aimed to optimize the synthesis stages of S-pregabalin ((S)-3-(aminomethyl)-5-methylhexanoic acid), a well-known anticonvulsant drug. We used appropriate solvents and compounds to reach a straightforward and applicable method. The advantages of this research were avoiding use of expensive and environment pollutant reagents and solvents, and also using a recoverable reagent. Discarding prevention of the intermediates and reagents besides attaining a higher yield of the obtained product were the additional achievements. All structures were characterized by FT-IR, 1H NMR, and the purity of S-pregabalin was evaluated using the HPLC assay.

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Abbreviations

GABA:

Gamma amino butyric acid

FDA:

Food and Drug Administration

MTBE:

Methyl tert-butyl ether

EE:

Enantiomeric excess

FT-IR:

Fourier-transform infrared spectroscopy

HPLC:

High-performance liquid chromatography

TLC:

Thin layer chromatography

UV:

Ultraviolet visible

MP:

Melting point

1H NMR:

Proton nuclear magnetic resonance

USP:

United States Pharmacopeia

UN:

United National

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Acknowledgements

We acknowledge “Deputy of Research and Technology” Tabriz University of Medical Sciences for financial support. We thank the officials of the pharmaceutical chemistry and pharmaceutical control laboratories of Pharmacy Faculty, Tabriz University of Medical Sciences for their cooperation during the study. We also appreciate Ms. Akram Faridi and Ms. Shirin Ahmadi for their sincere help. This paper is based on the MSc thesis (7.) submitted by A. Mansoori, Pharmacy Faculty, Tabriz University of Medical Sciences.

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Authors and Affiliations

  1. Student Research Committee, Tabriz University of Medical Sciences, Tabriz, Iran

    Arsalan Mansoori & Fahimeh Zahednezhad

  2. Faculty of Pharmacy, Drug Applied Research Center, Tabriz, Iran

    Arsalan Mansoori & Fahimeh Zahednezhad

  3. Biotechnology Research Center, Tabriz University of Medical Sciences, Tabriz, Iran

    Ahad Bavili Tabrizi

  4. Department of Medicinal Chemistry, Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran

    Javid Shahbazi Mojarrad

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  1. Arsalan Mansoori
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  2. Fahimeh Zahednezhad
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  3. Ahad Bavili Tabrizi
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  4. Javid Shahbazi Mojarrad
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Correspondence to Javid Shahbazi Mojarrad.

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Mansoori, A., Zahednezhad, F., Bavili Tabrizi, A. et al. Development of a new synthesis approach for S-pregabalin by optimizing the preparation stages. J IRAN CHEM SOC 17, 89–101 (2020). https://doi.org/10.1007/s13738-019-01759-3

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