Process for the production of benzopyran-2-ol derivatives

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...

Reexamination Certificate

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C549S399000, C560S140000, C564S316000

Reexamination Certificate

active

08067594

ABSTRACT:
The invention provides a process for producing a compound of formula (I),wherein Y is selected from the group consisting of CH3, CH2OH, CH2CH2OH, CH2Br and Br; comprising the steps of:(i) reacting a compound of formula (II),wherein OX represents hydroxy or O−M+, in which M+is a cation selected from Li+, Na+and K+, andY is as defined above;with trans-cinnamaldehyde (III),in the presence of a secondary amine compound; then(ii) treating the product of the preceding step with acid to afford the compound of formula (I).The above process may also be used in the production of tolterodine and fesoterodine, which are useful in the treatment of overactive bladder.

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patent: 6858650 (2005-02-01), Meese
patent: 2004/0209916 (2004-10-01), Richards
patent: 1254890 (2002-11-01), None
patent: WO 9829402 (1998-07-01), None
patent: 9958478 (1999-11-01), None
patent: 0149649 (2001-07-01), None
Jurd, L. “Synthesis of 4-phenyl-2H-1-benzopyrans”, Journal of Heterocyclic Chemistry, vol. 28, No. 4, 1991, pp. 983-986.
Botteghi, C. et al., “A new efficient route to tolterodine”, Organic Process Research & Development, vol. 6, No. 4, Jul. 2002, pp. 379-383.
Saimoto, et al., “Synthesis of 3,4-Dihydro-2H-Benzopyrans from Phenols and α,β-Unsaturated Carbonyl Compounds”, Heterocycles, vol. 55, 2001, pp. 2051-2054.

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