Back to results
US 2006/0189827 A1Published application
Process for the preparation of tolterodine
AssigneeDipharma S.p.A.
InventorsGabriele Razzetti, Simone Mantegazza, Roberto Rossi, Pietro Allegrini
Life of this patent
Estimating the term…
Abstract
A novel process for the preparation of tolterodine, i.e. (R)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine, in the racemic form, as well as intermediates useful for its preparation.
Claims10
A process for the preparation of tolterodine or a pharmaceutically acceptable salt thereof, comprising:
- A) reacting a compound of formula (II)
- in which when X is —CH2— then R is —(isopropyl)2;
- or when X is ═CO then R is —N (isopropyl)2 or —OR1, wherein R1 is an aryl or a straight or branched
- C1-C6 alkyl group, optionally substituted with phenyl;
- with an acidic agent;
- or
- B) reacting a compound of formula (III)
- wherein Y is a group able to provide a benzylic carbocation and Z is hydrogen or Y and Z, taken together, complete a double bond;
- and X and R are as defined above, with p-cresol and an acidic agent;
- to obtain, respectively, when in a compound of formula (II) or (III)
- a) X is —CH2— and R is —N(isopropyl)2, a compound of formula (I)
- i.e. tolterodine free base;
- or when
- b) X is ═CO and R is —N(isopropyl)2, a compound of formula (III)
- which by reduction yields tolterodine free base;
- or when
- c) X is ═CO and R is a —OR1 group wherein R1 is as defined above, a compound of formula (IV)
- wherein R1 is as defined above, which is converted to tolterodine free base;
- and, if desired, the conversion of tolterodine free base to a pharmaceutically acceptable salt thereof.
16 more elements
A compound of formula (II)
- in which when X is —CH2— then R is —N(isopropyl)2;
- or when X is ═CO then R is —N(isopropyl)2 or —OR1, wherein R1 is an aryl or a straight or branched
- C1-C6 alkyl group, optionally substituted with phenyl.
Dependencies are inferred from the claim text.