Dr Werner Seebacher, University of Graz
University of Graz
Piperidin-4-ones are useful intermediates for the syntheses of 4-aminopiperidine therapeutic compounds such as fentanyl, alfentanil, sufentanil, remifentanil, bamipine, thenaldine, astemizol, indoramin, diphenylpyraline, pimozide, domperidone, loperamide etc. also the 4-aryl, 4-hydroxypiperidine drug haloperidol is obtainable from the piperidin-4-one intermediate. Due to the pharmacological potential of piperidin-4-ones and products thereof, it is of high interest to have a large variety of potential substitution patterns. Especially, piperidin-4-ones with substitution at the carbon atom adjacent to the nitrogen are rarely available. Thus, 2-substituted derivatives of most of the drugs or active substances, which can be made from piperidin-4-ones, have not been investigated until now. To cover a complete structure-activity relationship of a substance class it is essential to investigate all relevant sites of substitution.
The present invention relates to a process for preparing a piperidin-4-one and novel piperidin-4-ones as well as a method of derivatizing a piperidin-4-one. The present invention provides alternative processes for preparing piperidin-4-ones or derivatives thereof, and especially processes, wherein piperidin-4-ones with various substitution patterns can be obtained, preferably 2-substituted piperidin-4-ones.
New derivatives of 4-aminopiperidine therapeutic compounds could include therapeutic compounds, superior over the currently available representatives. According to GlobalData, the markets for analgesics, antipsychotics and antihistaminics, which are probably the most relevant to the newly accessible compounds, are growth markets.
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The present invention provides alternative processes for preparing piperidin-4-ones or derivatives thereof, and especially processes, wherein piperidin-4-ones with various substitution patterns can be obtained, preferably 2-substituted piperidin-4-ones.
Preclinical pharmacological testing has not been performed yet.
European patent (PROCESS FOR PREPARING A PIPERIDIN-4-ONE, EP18211702.8) was filed on December 11, 2018.
Mohsin N U, Seebacher W, Faist J, Hochegger P, Kaiser M, Mäser P, Belaj F, Saf R, Kretschmer N, Alajlani M, Turek I, Brantner A, Bauer R, Bucar F, Weis R. Synthesis of new 1-benzyl tetrahydropyridinylidene ammonium salts and their antimicrobial and anticellular activities. Eur J Med Chem (2018) 143:97-106. DOI 10.1016/j.ejmech.2017.11.025
Seebacher W, Faist J, Belaj F, Saf R, Kaiser M, Brun R, Weis R. Synthesis of new tetrahydropyridinylidene ammonium salts and their antiprotozoal potency. Monatsh Chem (2015) 146:1299–1308 DOI. 10.1007/s00706-015-1503-y
Mohsin N U, Seebacher W, Faist J, Kretschmer N, Bauer R, Saf R, Kaiser M, MäserP, Weis R. Modifications on tetrahydropyridin-4-ylidene ammonium salts and their antiprotozoal activities. Monatsh Chem (2018) 149:801–812. DOI 10.1007/s00706-017-2111-9