286930-02-7 Usage
Description
(R) Fesoterodine, also known as Toviaz, is an orally active pro-drug that is converted in vivo to its active metabolite 5-HMT through hydrolysis by non-specific esterases. It is a potent muscarinic antagonist with equivalent affinity for M1, M2, M3, M4, and M5 receptors. Fesoterodine is used for the treatment of Overactive Bladder (OAB) and is supplied as its fumarate salt in an extended-release tablet form.
Uses
Used in Pharmaceutical Industry:
(R) Fesoterodine is used as a treatment for Overactive Bladder (OAB) due to its potent muscarinic antagonist properties, which help in managing the symptoms of OAB. It is effective in improving the quality of life for patients suffering from this condition.
The recommended starting dose is 4 mg once daily, which may be increased to 8 mg once daily based on individual response and tolerability. Fesoterodine is rapidly and completely bioconverted to 5-HMT, which has a bioavailability of about 52%. Plasma concentrations of 5-HMT are proportional to the dose, and maximum plasma levels are reached after approximately 5 hours. No accumulation occurs after multiple-dose administration.
Originator
Schwarz Pharma (Germany)
Synthesis
The chemical synthesis of fesoterodine starts with the cyclization of 4-(hydroxymethyl)phenol with cinnamaldehyde by means of piperazine in refluxing toluene to produce 2-hydroxy-6-(hydroxymethyl)-4-phenyl-3,4-dihydro-2H-1- benzopyran, which is subjected to reductive amination with To Market, To Market 2008 605 diisopropylamine by means of hydrogen over palladium hydroxide catalyst. The resultant racemic amine intermediate is optically resolved with (R)-(2)-acetoxy-2-phenylacetic acid to yield the corresponding (R)- enantiomer, which is finally acylated with isobutyryl chloride to afford fesoterodine.
Check Digit Verification of cas no
The CAS Registry Mumber 286930-02-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,8,6,9,3 and 0 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 286930-02:
(8*2)+(7*8)+(6*6)+(5*9)+(4*3)+(3*0)+(2*0)+(1*2)=167
167 % 10 = 7
So 286930-02-7 is a valid CAS Registry Number.
286930-02-7Relevant articles and documents
PROCESS FOR THE PREPARATION OF OPTICALLY PURE FESOTERODINE DERIVATIVES
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Paragraph 0245; 0246, (2015/04/15)
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.
PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE 3,3-DIPHENYLPROPYLAMINES
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Page/Page column 35; 36, (2013/08/15)
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.
"Process for the preparation of fesoterodine or a salt thereof"
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Page/Page column 7-8, (2012/06/18)
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.