103887-32-7

Usage

Chemical Properties

White Foam

Uses

An impurity arising in the synthesis of Darifenacin (D193500).

Upstream product

• 133099-11-3 (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetonitrile 
• 1189753-52-3 (S)-2,2-diphenyl-2-[1-(tert-butyloxycarbonyl)-3-pyrrolidinyl]acetonitrile 
• 133099-09-9 (S)-diphenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-acetonitrile 
• 86-29-3 Diphenylacetonitrile 
• 40499-83-0 (3R)-pyrrolidinol 
• 134002-26-9 (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate 

Downstream Products

• 808757-06-4 2-[(S)-1-(8-N-benzyl-N-methylaminooctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide 
• 586346-94-3 darifenacin hydrochloride 
• 133099-04-4 darifenacin 
• 133099-05-5 2-{(3R)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamide 

Relevant academic research and scientific papers

A new solvent system (Cyclopentyl methyl ether-water) in process development of darifenacin HBr

Darifenacin is a potent and competitive M3 selective receptor antagonist (M3SRA), and its hydrobromide salt (1) is the active ingredient of pharmaceutical formulations for oral treatment of urinary incontinence. The present work demonstrates an efficient, commercial manufacturing process for darifenacin hydrobromide (1).

PROCESS FOR PREPARATION OF DARIFENACIN AND INTERMEDIATES USED IN THE PROCESS

Disclosed herein is a process for the preparation of darifenacin and physiologically acceptable salts thereof. Also disclosed is a compound of formula X: wherein R is linear or branched C 1-10 alkyl, phenyl, tolyl, ortho-, meta- or para- xylyl

PROCESS FOR PREPARING 3-SUBSTITUTED PYRROLIDINE COMPOUNDS

Disclosed is a process for preparing 3 -substituted pyrrolidine compounds of formula (VII) or salts thereof, wherein R1 is described herein, which are intermediate compounds useful for the synthesis of darifenacin which is indicated for the treatment of overactive bladder with symptoms of urge, urinary incontinence, and the like, and pharmaceutically acceptable salts thereof. Also disclosed is a process for preparing darifenacin and pharmaceutically acceptable salts thereof.

SUBSTITUTED PYRROLIDINES

Disclosed herein are substituted pyrrolidine-based muscarinic receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

IMPROVED PROCESS FOR PRODUCING DARIFENACIN

The present invention discloses an improved process for producing darifenacin, the process comprising decarboxylating (2S,4R)-4-hydroxy-2-pyrrolidine carboxylic acid followed by in situ tosylation to give l-tosyl-3-(R)-(-)-hydroxypyrrolidine, tosylating the l-tosyl-3-(R)-(-)-hydroxypyrrolidine with methyl-p-toluenesuolphonate to give l-tosyl-3- (S)-(-)-tosyloxy pyrrolidine, reacting l-tosyl-3-(S)-(-)-tosyloxy pyrrolidine with diphenyl acetonitrile in presence of a base to give 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl)-l- tosylpyrrolidine, de-protecting 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl)-l- tosylpyrrolidine in the presence of phenol in acidic medium to give 3-(S)-(+)-(l-cyano- 1,1-diphenylmethyl) pyrrolidine, hydrolyzing 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl) pyrrolidine followed by salt formation to obtain 3-(S)-(+)-(l-carbamoyl-l,l- diphenylmethyl)pyrrolidine.L-(+)-tartrate, condensing 3-(S)-(+)-( 1 -carbamoyl- 1,1- diphenylmethyl)pyrrolidine-L(+)-tartrate with 5-(2-bromoethyl)-2,3-dihydrobenzofuran employing a base in a solvent to give darifenacin.

NOVEL AND IMPROVED PROCESSES FOR THE PREPARATION OF INTERMEDIATES OF DARIFENACIN, DARIFENACIN AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention relates to novel and improved processes for the preparation of intermediates of darifenacin, darifenacin and its pharmaceutically acceptable salts. Darifenacin is chemically known as 3 -(S)-(-)-(l -carbamoyl- 1,1 -diphenylmethyl)-l- [2- (2,3-dihydro benzofuran-5-yl)ethyl]pyrrolidine and represented by formula-2. The invention also relates to the novel polymorphs of the pharmaceutically acceptable salts of darifenacin and the methods for their re aration.

Quaternary ammonium diphenylmethyl compounds useful as muscarinic receptor antagonists

The invention provides compounds of formula I: in salt or zwitterionic form or a pharmaceutically acceptable salt thereof, wherein R1-6, a-e and Q are as defined in the specification. These compounds are muscarinic receptor antagonists. The inv

PREPARATION OF DARIFENACIN AND ITS SALTS

Provided are various processes and compounds related to darifenacin and/or its salts. For example, there is provided a process for preparing a free base of darifenacin: Formula, or the salt thereof, the process including reacting 3-(S)-(cyanodiphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl) ethyl] pyrrolidine of the Formula (IV), or a salt thereof: Formula (IV) with a base effective to convert the nitrile group of the compound of the Formula (IV) to the amide group of the darifenacin in an organic solvent, the reaction being carried out in the organic solvent, with a proviso that the solvent is not 2-methyl-butan-2-ol, and with further proviso that the reaction produces less than about 0.5 % of the compound of the Formula (Ic): Formula (Ic) in the reaction mass, as measured by HPLC. Various embodiments and variants are provided.

PROCESSES FOR PREPARING DARIFENACIN HYDROBROMIDE

The invention encompasses processes for the preparation of darifenacin hydrobromide.

SUBSTITUTED 4-AMINO-1-BENZYLPIPERIDINE COMPOUNDS

This invention provides 4-amino-1-benzylpiperidine and related compounds and pharmaceutically acceptable salts thereof which are useful as muscarinic receptor antagonists. This invention also provides pharmaceutical compositions containing such compounds; processes and intermediates useful for preparing such compounds; and methods for treating disease conditions mediated by muscarinic receptors, such as overactive bladder, irritable bowel syndrome, asthma and chronic obstructive pulmonary disease, using such compounds.