- PROCESS FOR THE PREPARATION OF OPTICALLY PURE FESOTERODINE DERIVATIVES
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3,3-diphenylpropylamines of general formula (I), particularly Fesoterodine, as well as their enantiomers, solvates and salts, can be produced by treating a compound of formula (II) with a chiral alcohol to yield the diastereomeric esters of formula (IV) and (IV′), which can be further transformed into a compound of formula (I), or an enantiomer, solvate or salt thereof, wherein R1 is C1-C8 alkyl; and R2 and R3, independently of one another, represent H or C1-C6 alkyl, or together form a ring of 3 to 7 members with the nitrogen to which they are bound.
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Paragraph 0245; 0246
(2015/04/15)
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- PROCESS FOR THE PREPARATION OF 2-(3-N,N-DIISOPROPYLAMINO-1-PHENYLPROPYL)-4-HYDROXYMETHYL-PHENOL AND ITS DERIVATIVES
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The invention concerns a process for the preparation of 2-(3-N,N- diisopropylamino-l-phenylpropyl)-4-hydroxymethyl-phenol and its derivatives, particularly the corresponding (R) 4-trityloxymethyl derivative, useful as intermediate form in the synthesis of Fesoterodine and its salts, in particular for the preparation of Fesoterodine fumarate salt.
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- PROCESS FOR THE PREPARATION OF FESOTERODINE OR ITS SALTS
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The present invention relates to a process for the preparation of fesoterodine or its salts.
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- PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE 3,3-DIPHENYLPROPYLAMINES
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The invention relates to a process for obtaining 3,3-diphenylpropylamines of general formula (I), particularly Fesoterodine, as well as their enantiomers, solvates and salts, comprising treating a compound of formula (II) with a chiral alcohol to yield the diastereomeric esters of formula (IV) and (IV'), which can be further transformed into a compound of formula (I), or an enantiomer, solvate or salt thereof, wherein R1 is C1-C8 alkyl; and R2 and R3, independently of one another, represent H or C1-C6 alkyl, or together form a ring of 3 to 7 members with the nitrogen to which they are bound.
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Page/Page column 35; 36
(2013/08/15)
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- PROCESS FOR THE PREPARATION OF MUSCARINIC RECEPTOR ANTAGONIST
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The present invention relates to novel and improved processes for the preparation of (r)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenylisobutyrate represented by the following structural formula-1 and its pharmaceutically acceptable salts thereof.
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Page/Page column 71
(2012/08/07)
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- PROCESSES FOR THE PREPARATION OF FESOTERODINE
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The invention relates to improved process for the preparation of fesoterodine and its pharmaceutically acceptable salt, specifically fesoterodine fumarate of formula (1). The invention relates to solid state forms of a novel salt of fesoterodine and process for the preparation thereof. The invention also relates to highly pure fesoterodine fumarate substantially free of impurity X at RRT 1.37. The invention also provides solid particles of pure fesoterodine fumarate wherein 90 volume-percent of the particles (D90) have a size of higher than 200 microns.
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- A PROCESS FOR PREPARING FESOTERODINE
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The present invention relates to an improved process for the preparation of Fesoterodine and pharmaceutically acceptable salts thereof. The present invention particularly relates to a process for the preparation of fesoterodine and pharmaceutically acceptable salts thereof which involves use and preparation of R(+) benzyl tolterodine and fumarate salt of R(+)-[4-benzyloxy-3-(3-diisopropylamino-1-phenylpropyl)-phenyl]-methanol.
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- "Process for the preparation of fesoterodine or a salt thereof"
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A process for the preparation of (R)-2-(3-diisopropylamino-1-phenylpropyl)-4-(hydroxymethyl)-phenol isobutyrate (Fesoterodine) or a pharmaceutically acceptable salt thereof having low content in impurities.
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Page/Page column 7-8
(2012/06/18)
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- PROCESS FOR THE PREPARATION OF FESOTERODINE OR A SALT THEREOF
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A process for the preparation of (R)-2-(3-diisopropylamino-1-phenylpropyl)-4-(hydroxymethyl)-phenol isobutyrate (Fesoterodine) or a pharmaceutically acceptable salt thereof having low content in impurities.
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Page/Page column 4-5
(2012/06/18)
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- PROCESS FOR PREPARATION OF PHENOLIC MONOESTERS OF HYDROXYMETHYL PHENOLS
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Disclosed herein is an improved and efficient process for preparation of fesoterodine and its pharmaceutically acceptable salt. Disclosed also herein is novel intermediate of formula (III). Also disclosed are metal salts of formula (XII) and preparation thereof.
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- PROCESS FOR PREPARATION OF PHENOLIC MONOESTERS OF HYDROXYMETHYL PHENOLS
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A process for the preparation of phenolic monoesters of 2-(3-diisopropylamino-1-phenylpropyl)-4-(hydroxymethyl)phenol by converting (±)6-halo-4-phenylchroman-2-one to (±)4-halo-2-(3-hydroxy-1-phenylpropyl)phenol. The two hydroxyl groups are protected and the protected compound is reacted with diisopropylamine to give (±)[3-(2-benzyloxy-5-halophenyl)-3-phenylpropyl]diisopropylamine. The halo substituent on the benzene ring is converted to corresponding benzyl alcohol and then the protection is removed to give racemic 5-HMT. Racemic 5-HMT is converted R enantiomer and then it is esterified.
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- IMPROVED PROCESS FOR DIPHENYLPROPYLAMINE DERIVATIVES
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The present invention relates to an improved process for the preparation of biologically active diphenylpropylamine derivatives. The present invention specifically relates to an improved fesoterodine of formula (I) and its pharmaceutically acceptable salts.
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- SHORT SYNTHESIS OF TOLTERODINE, INTERMEDIATES AND METABOLITES
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A process is described for the preparation of intermediates which can be used for preparation of agents for urinary incontinence therapy, specifically to 2-(3-(diisopropylamino)- 1-phenylpropyl)-4-(hydroxymethyl)phenol and its prodrugs.
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- The lactol route to fesoterodine: An amine-promoted Friedel-Crafts alkylation on commercial scale
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We report the discovery and optimization of an amine-promoted Friedel-Crafts alkylation of cinnamaldehyde with 4-hydroxymethyl phenol. This reaction has been used successfully on commercial scale (200 kg) in the context of the manufacture of fesoterodine, a muscarinic antagonist used for the treatment of overactive bladder. Reductive aminations of diisopropylamine and lactol 4 are also discussed, as well as the resolution of the racemic amine rac-2 into its enantiomerically pure form.
- Dirat, Olivier,Bibb, Andrew J.,Burns, Colin M.,Checksfield, Graham D.,Dillon, Barry R.,Field, Stuart E.,Fussell, Steven J.,Green, Stuart P.,Mason, Clive,Mathew, Jinu,Mathew, Suju,Moses, Ian B.,Nikiforov, Petar I.,Pettman, Alan J.,Susanne, Flavien
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p. 1010 - 1017
(2011/12/16)
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- Process for preparation of 3-(2-hydroxy-5-substituted phenyl)-3-phenylpropylamines, intermediates for making hydroxytolterodine
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A process is described for the preparation of 3-(5-formyl-2-hydroxyphenyl)-3-phenylpropylamine derivatives, intermediates which can be used for preparation of agents for urinary incontinence therapy, specifically to 2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol and its prodrugs.
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- SOLID STATE FORMS OF FESOTERODINE INTERMEDIATES
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Provided herein are novel solid state forms of fesoterodine intermediates, (R)-4-benzyloxy-3-(3-diisopropylamino-1-phenylpropyl)-benzoic acid and (R)-[4-benzyloxy-3-(3-diisopropylamino-1-phenylpropyl)-phenyl]-methanol, and processes for their preparation thereof. The solid state intermediates are useful for preparing fesoterodine or a pharmaceutically acceptable salt thereof in high purity.
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- Process for the preparation of fesoterodine
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A process for the preparation of (R)-2-(3-diisopropylamino-1-phenylpropyl)-4-(hydroxymethyl)-phenol isobutyrate (Fesoterodine), its (S)-enantiomer, and novel intermediates useful in thei synthesis.
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- A process for the preparation of fesoterodine with low impurities content
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Disclosed is a process for the preparation of (R)-2-(3-diisopropylamino-1-phenylpropyl)-4-(hydroxymethyl)-phenol isobutyrate (Fesoterodine) or a pharmaceutically acceptable salt thereof having a low content of impurities such as tolterodine and tolterodine isobutyrate.
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- PROCESS FOR THE PREPARATION OF FESOTERODINE
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A process for the preparation of (R)-2-(3-diisopropylamino-1-phenylpropyl)-4-(hydroxymethyl)-phenol isobutyrate (Fesoterodine), its (S)-enantiomer, and novel intermediates useful in thei synthesis.
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- PREPARATION PROCESS OF FESOTERODINE AND INTERMEDIATES
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The present invention relates to a process of synthesis of 3,3 dipheylpropylamines, which may be used as pharmaceutical intermediates in the preparation of their pharmacologically active derivatives such as fesoterodine, tolterodine, their enantiomers, pharmaceutically acceptable salts and related compounds useful as antimuscarinic agents.
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- CRYSTALLINE FORMS OF FESOTERODINE FUMARATE AND FESOTERODINE BASE
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Polymorphically pure crystalline forms of fesoterodine fumarate and fesoterodine base are described and characterized.
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Page/Page column 13-14
(2011/04/14)
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- Fesoterodine Substantially Free of Dehydroxy Impurity
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Provided herein is an impurity of fesoterodine, fesoterodine dehydroxy impurity, 2-[(1R)-3-[bis(1-methylethy)amino]-1-phenylpropyl]-4-methylphenyl isobutyrate, and a process for preparing and isolating thereof. Provided further herein is a highly pure fesoterodine or a pharmaceutically acceptable salt thereof substantially free of fesoterodine dehydroxy impurity, process for the preparation thereof, and pharmaceutical compositions comprising highly pure fesoterodine or a pharmaceutically acceptable salt thereof substantially free of dehydroxy impurity. Provided also herein is a pharmaceutical composition comprising solid particles of pure fesoterodine fumarate substantially free of dehydroxy impurity, wherein 90 volume-percent of the particles (D90) have a size of less than about 200 microns.
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- FESOTERODINE SUBSTANTIALLY FREE OF DEHYDROXY IMPURITY
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Provided herein is an impurity of fesoterodine, fesoterodine dehydroxy impurity, 2-[(lR)-3- [bis(l-methylethyl)amino]-l-phenylpropyl]-4-methylphenyl isobutyrate, and a process for preparing and isolating thereof. Provided further herein is a highly pure fesoterodine or a pharmaceutically acceptable salt thereof substantially free of fesoterodine dehydroxy impurity, process for the preparation thereof, and pharmaceutical compositions comprising highly pure fesoterodine or a pharmaceutically acceptable salt thereof substantially free of dehydroxy impurity. Provided also herein is a pharmaceutical composition comprising solid particles of pure fesoterodine fumarate substantially free of dehydroxy impurity, wherein 90 volume-percent of the particles (D90) have a size of less than about 200 microns.
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Page/Page column 25-26
(2010/04/03)
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- Process for the Preparation of Fesoterodine
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Disclosed herein is an improved, commercially viable and industrially advantageous process for the preparation of Fesoterodine or a pharmaceutically acceptable salt thereof in high yield and purity. Disclosed also herein is an improved and industrially advantageous optical resolution method of racemic (±)-N,N-Diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropylamine and use thereof for the preparation of Fesoterodine.
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Page/Page column 10
(2010/09/05)
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- PROCESS FOR THE PRODUCTION OF BENZOPYRAN-2-OL DERIVATIVES
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The invention provides a process for the production of a compound of formula (I), wherein Y is selected from CH3, CH2OH, CH2CH2OH, CH2Br and Br; comprising the steps of: (i) reacting a compound of formula (II), wherein OX is hydroxy or O- M+, in which M+ is a cation selected from Li+, Na+ and K+, and Y 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 be used in the production of tolterodine and fesoterodine, which are useful in the treatment of overactive bladder.
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Page/Page column 27; 29
(2008/06/13)
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- SYNTHESIS OF PHENOLIC ESTERS OF HYDROXYMETHYL PHENOLS
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The present invention provides a process for the production of a compound of formula (I) or a salt thereof, wherein R is hydrogen, a straight, branched or cyclic C1-C6 alkyl group or an aryl group which may optionally be substituted. This process comprises: (a) reacting a compound of formula (II), with a compound of formula (III), wherein R is as defined above and X is a leaving group, in the presence of N, N-diisopropylethylamine.
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Page/Page column 12-14
(2008/06/13)
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- HIGHLY PURE BASES OF 3,3-DIPHENYL PROPYLAMINE MONOESTERS
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The invention relates to a compound of general formula (I) wherein A represents deuterium or hydrogen, R represents a group selected from C1-6 alkyl, C3-10 cycloalkyl or phenyl, which can be substituted by C1-3 alkoxy, fluorine, chlorine, bromine, iodine, nitro, amino, hydroxyl, oxo, mercapto or deuterium. The C atom marked with a *(star) can be present in an (R) configuration, in an (S)-configuration or a mixture thereof. The invention is characterised in that the above-mentioned compounds are free bases with a degree of purity of more than 97 wt %. The invention also relates to a method for the production of highly pure compounds of general formula (I) and to the use thereof in the production of medicaments.
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Page/Page column 45-46
(2008/06/13)
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