The UJI creates a new method to separately synthesize enantiomers in anti-inflammatory, analgesic or ADHD drugs



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## The UJI creates a new method to separately synthesize enantiomers in anti-inflammatory, analgesic or ADHD drugs

03/05/2018 |
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The research group “Organic and Medicinal Chemistry” of the Universitat Jaume I in Castelló, led by Florenci V. González Adelantado, has developed a new procedure for the efficient production of enantiomers in certain drugs. The technology, of which the lecturer Santiago Rodríguez Pastor and the predoctoral researcher Lledó Bou Iserte are co-authors, is applicable mainly in pharmaceutical companies dedicated to the production of active ingredients and anti-inflammatory drugs, analgesics or medication indicated for the treatment of attention deficit for hyperactivity (ADHD), specifically profens and phenidates.

Enantiomers or chiral molecules are a pair of organic or inorganic compounds present at the same time in the same drug, but with different consequences. *Chiral* is a Greek term meaning "hand", and just as hands are mirror images, identical but opposite, organic compounds can be mirror images at the molecular level: they look similar, but they do not always behave in the same way.

Science has observed different types of situations depending on the effects produced by the enantiomeric forms of a chiral drug in the organism. There are drugs in which each enantiomer produces an opposite effect; in other cases, the effect is similar, but one is more active than the other is; it could also be that one enantiomer is active and the other inactive and, finally, one has a beneficial effect, while the other is toxic. “Normally, they are commercialized as racemic mixtures — explains the researcher Lledó Bou Iserte — that is, we have a mixture of the two enantiomers. When this happens, it is because one is the active one and the other may be active or inactive. However, other drugs are supplied as a single enantiomer, since their opposite is harmful to health”.

One of the best-known examples of the toxic effects of chirality in medicines is thalidomide. The right isomer of this drug is a good medicine for pregnant women because it prevents nausea, but if a pregnant woman is given the left isomer, it could produce physical defects in the foetus.

To solve the drawbacks that, in some cases, involves administering both chiral forms of the same drug, the pharmaceutical industry has been forced to make new syntheses to obtain the desired chiral version, regardless of the inactive, inefficient or toxic form. The usual method applied so far is to prepare a drug as a racemate (mixture of equal proportion of both enantiomers) and then separate the chiral forms, but a large amount of product is lost. The ideal synthesis is one that selects, from the first moment, the enantiomers.

The invention patented by the Universitat Jaume I in Castelló is a method applicable at an industrial level that allows synthesizing only one of the enantiopure forms in the chiral drugs and phenidates. This simpler procedure makes it possible to make better use of the starting raw materials and reduces the generation of waste or by-products. In addition, unlike other methods of enantioselective synthesis of profens, the procedure patented by the UJI does not use sophisticated reagents, which favours its industrial implantation. «This method allows obtaining this compound in a pure form. Normally, when it is marketed, we have a mixture of one part that is active and one that is inactive. In this way, we are only getting the active part and in an effective way”, says Lledó Bou Iserte.

The new method of enantioselective synthesis of drugs has several advantages: it allows obtaining enantiopure forms of the drug without the need to prepare it as a racemate; it simplifies the process because there is no need to synthesize it later; it avoids the loss of a large part of the product; it does not use sophisticated reagents, which facilitates its industrial application, and when using small amounts of phase transfer catalysts (PTC type) it does not generate toxic residues, nor does it obtain a final product with traces of toxic metal contaminants. The procedure has been validated in laboratory. It is available for a license agreement for use, manufacture, marketing or application development.

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