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The evaluation of tolterodine tartrate synthesis based on patent EP 0 325 574 B1.

Paulina Bujak ,  Wojciech Łuniewski ,  Marcin Cybulski 

Pharmaceutical Research Institute (IF), Rydygiera 8, Warszawa 01-793, Poland


Tolterodine is used to relieve urinary difficulties, including frequent urination and inability to control urination. Tolterodine belongs to a class of medications called antimuscarinics. It acts by preventing bladder contraction. It is sold under the trade names Detrol and Detrusitol. DETROL Tablets are indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and frequency.

The chemical name of tolterodine is (R)-N,N-diizopropyl-3-
(2-hydroxy-5-methylphenyl)- -3-phenylpropamine. It is delivered in pharmaceutical form as a tartrate. The empiric formula is C26H37NO7 and the structural formula is represented below:

Synthesis of tolterodine tartrate was firstly revealed in patent EP 0325571 B1 published in 1989. It describes synthesis consisted of seven steps, which starts from p-cresol and trans-cinnamic acid. There is also a modification of first method. This alternative route contains eight synthetic steps. We found that patent description lacks a lot of very important information e.g. purity of intermediates or methods of their purification. It was not mentioned if products were obtained in crystalline, amorphous or oil form.

We decided to investigate both of synthetic routes to gain missing information and to evaluate their usefulness for application in industrial scale.


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Related papers

Presentation: Poster at VI Multidyscyplinarna Konferencja Nauki o Leku, by Paulina Bujak
See On-line Journal of VI Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2008-04-24 11:09
Revised:   2009-06-07 00:48