- Synthesis/Isolation of darifenacin hydrobromide by-products
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During the process development in the laboratory, the purity of darifenacin hydrobromide has been tested by HPLC. Three byproduct peaks along with darifenacin 1 peak have been observed whose area percentage ranged from 0.06-0.20% by HPLC. As per the strin
- Vasantha,Lakshmanarao,Srinivasa Rao,Sivalakshmi Devi,Venkata Suryanarayana
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p. 824 - 828
(2013/07/26)
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- A new solvent system (Cyclopentyl methyl ether-water) in process development of darifenacin HBr
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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).
- Pramanik, Chinmoy,Bapat, Kiran,Chaudhari, Ashok,Tripathy, Narendra K.,Gurjar, Mukund K.
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p. 1591 - 1597
(2013/02/23)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF DARIFENACIN HYDROBROMIDE
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The present invention relates to an improved process for the preparation of Darifenacin hydrobromide of Formula (I). (i) condensing 3-(S)-(-)-1l-carbamoyl-1,1-diphenylmethyl)pyrrolidine (III), or its salt, with a compound of Formula XIII in the presence of a. base in a solvent, wherein X represents Cl, Br, C1-3 alkyl sulfonate or C6-10 arγl sulfonate; to produce (S)-2-[1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-3- pyrrolidinyl]-2,2-diphenylacetamide (Darifenacin) (Ia), (ix) treating (S)-2-[1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-3-pyrrolidinyl]- 2,2-diphenylacetamide (Darifenacin) (Ia) with an acid in a solvent and water mixture, (x) isolating pure (S)-2-[1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-3- pyrrolidinyl]-2,2-diphenylacetamide (Darifenacin) (Ia), (xi) treating pure Darifenacin (Ia) with HBr to produce Darifenacin hydrobromide (I).
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- Novel Polymorphs of Darifenacin Free Base and its Hydrobromide Salt
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The present invention provides a novel and stable amorphous form of darifenacin free base, process for preparation, pharmaceutical compositions, and method of treating thereof. The present invention further provides a novel and stable polymorphic form of darifenacin hydrobromide, process for preparation, pharmaceutical compositions, and method of treating thereof.
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Page/Page column 7
(2010/08/18)
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- Method for obtaining 1,3-difunctionalized pyrrolidine derivatives
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The present invention relates to a method for obtaining 1,3-difunctionalized pyrrolidine derivatives, such as 3-(S)-(-)-(1-carbamoyl-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine, commonly known as Darifenacin, as well as to the i
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Page/Page column 17
(2010/10/19)
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- NOVEL PROCESS FOR THE PREPARATION OF (3SM-[2-(2 J-DIHYDRO-5- BENZOFURANYL?ETHYL]-α.α -DIPHENYL-3-PYRROLIDINEACETAMIDE HYDROBROMIDE
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The present invention is directed to a novel, industrially viable and cost effective process for manufacturing (3 S)- 1 -[2-(2,3-Dihydro-5-benzofuranyl)ethyl]-a,a-diphenyl-3-pyrrolidineacetamide hydrobromide also known as Darifenacin hydrobromide.
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- IMPROVED PROCESS FOR PRODUCING DARIFENACIN
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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.
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- A METHOD FOR THE PREPARATION OF DARIFENACIN HYDROGEN BROMIDE
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A method of preparing (3S)-l-[2-(2,3-dihydro-5-benzofuranyl)ethyl}-α,α-diphenyl-3- pyrrolidine acetamide hydrogen bromide, wherein 3-(S)-(I -carbamoyl- 1,1- diphenylmethyl)pyrrolidine or its salt with an organic acid is alkylated in the presence of an ino
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Page/Page column 9-10
(2009/09/05)
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- NOVEL AND IMPROVED PROCESSES FOR THE PREPARATION OF INTERMEDIATES OF DARIFENACIN, DARIFENACIN AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS
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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.
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- Method For Determining Enantiomeric Purity Of Darifenacin And Intermediates
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The present invention relates to a method for differentiating and quantifying the enantiomers, thereby determining the enantiomeric purity, of darifenacin and its intermediate compounds and salts thereof. In addition, the invention relates to a method for
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Page/Page column 6-8
(2009/01/24)
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- PREPARATION OF DARIFENACIN AND ITS SALTS
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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.
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Page/Page column 41
(2008/12/08)
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- IMPROVED METHOD FOR PREPARING 1,3-DISUBSTITUTED PYRROLIDINE COMPOUNDS
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A process for preparing substituted pyrrolidine compounds, including (5)-2-{l-[2- (2,3-dihydrobenzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide hydrobromide, commonly known in the art as darifenacin, comprising reacting a pyrrolidine compound w
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Page/Page column 12-13
(2008/06/13)
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- PROCESSES FOR PREPARING DARIFENACIN HYDROBROMIDE
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The invention encompasses processes for the preparation of darifenacin hydrobromide.
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Page/Page column 49
(2008/06/13)
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- Stable hydrate of a muscarinic receptor antagonist
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A stable solid hydrate of a muscarinic receptor antagonist is useful in the treatment of irritable bowel syndrome, diverticular disease, oesophageal achalasia, chronic obstructive airways disease, over active bladder (including symptoms of incontinence, u
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