cas 242478-38-2, Solifenacin succinate | Articles data

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Solifenacin succinate new preparation method
The present invention relates to a solifenacin succinate new preparation method which mainly comprises the following steps: 1) formula III compound (R)-(-)-quinuclidin-3-ol and formula IV compound N,N,-N,N-carbonyldiimidazole are reacted to obtain formula V compound (R)-imidazole-1-carboxylic acid-1-azabicyclo[2,2,2] octyl ester; 2) the formula V compound (R)-imidazole-1-carboxylic acid-1-azabicyclo[2,2,2] octyl ester is reacted with formula VI compound (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline to obtain a formula II solifenacin alkaline body; 3) the formula II solifenacin alkaline body isreacted with succinic acid, refined and purified to obtain formula I solifenacin succinate. The preparation method has the advantages that the yield of the solifenacin succinate is high and the purityis high, and the process is simple and suitable for industrial production.
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Paragraph 0012; 0014

(2018/08/03)

A succinic acid thorley that new preparation method
The invention relates to a preparation method of succinic acid solifenacin, and belongs to the technical field of medicinal raw material preparation. According to the technical scheme, the preparation method of the novel succinic acid solifenacin is characterized in that R-3-quinuclidinol, S-1-phenyl-1, 2, 3, 4-tetrahydro naphthalene are used as raw materials, a reaction product of triphosgene and substituted phosphine oxide is used as a condensing agent, the solifenacin is prepared through a one-pot method, and then the succinic acid solifenacin is obtained through salifying. The preparation method of the succinic acid solifenacin has the beneficial effects that the operation is simple, reaction conditions are mild, and the preparation method is suitable for industrial amplification production.
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Paragraph 0018; 0037-0039

(2017/09/19)

A process for the preparation of new thorley that succinic acid
The invention relates to a method for preparing a solifenacin succinate ((3R)-1-azabicyclo [2.2.2] octane-3-yl (1S)-1-phenyl-3,4-dihydroisoquinoline-2-(1H)-carboxylate succinate). The method comprises the following steps: 1) preparing a compound (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline carboxylic acid ethyl ester of formula III from a compound (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline, serving as a raw material, of formula IV; 2) synthesizing a compound (3R)-1-azabicyclo [2.2.2] octane-3-yl (1S)-1-phenyl-3,4-dihydroisoquinoline-2-(1H)-carboxylate of formula II in an ionic liquid by using the compound (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline carboxylic acid ethyl ester of formula III; and 3) salifying the compound (3R)-1-azabicyclo [2.2.2] octane-3-yl (1S)-1-phenyl-3,4-dihydroisoquinoline-2-(1H)-carboxylate of formula II in an organic solvent to obtain the compound solifenacin succinate ((3R)-1-azabicyclo [2.2.2] octane-3-yl (1S)-1-phenyl-3,4-dihydroisoquinoline-2-(1H)-carboxylate succinate) of formula I. The preparation method has the advantages that the process is simple, the method is suitable for industrialized production, the yield of the product is high and the purity of the product is high.
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Paragraph 0071

(2016/10/07)

After-treatment for solifenacin and method for preparing succinic acid solifenacin
The invention discloses an after-treatment method for solifenacin. The method comprises the steps that strong acid is slowly dripped into total synthesis liquid of solifenacin, after a pH value is adjusted to be 1.0-2.0, temperature is raised, water is added, and an extracting agent is used for extraction; after a water phase is cooled, a saturated sodium carbonate solution is added to alkalinity, dichloromethane is added to carry out graded extraction, extract liquor is washed with water, and a drying agent is added for drying, so that a dry product is obtained; the dry product is steamed at low temperature to be dry to obtain an oily substance solifenacin. By optimizing the after-treatment technology, isopropyl ether and dichloromethane are only used in the after-treatment technology of solifenacin, types of solvent are reduced, operation and recycle are facilitated, and cost is saved greatly. Strong base or strong acid is not used in the alkali efflorescence process of hydrochloric acid solifenacin, a saturated NaCO3 solution is used, the reaction is mild, temperature can be controlled easily, most importantly, generation of isomers is greatly reduced, and the content of the isomers of a non-structure type (1S and 3R) is reduced.
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Paragraph 0062; 0063

(2016/12/01)

PROCESS OF PREPARING SOLIFENACIN OR SALT THEREOF, AND NOVEL INTERMEDIATE USED IN THE PROCESS
Disclosed herein is a method of preparing solifenacin or a salt thereof, including the steps of: (a) reacting (R)-quinuclidinol with bis(pentafluorophenyl)carbonate in an organic solvent to prepare a solifenacin intermediate, (3R)-1-azabicyclo[2,2,2]oct-3-yl pentafluorophenylcarbonate, and (b) reacting the solifenacin intermediate with (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline in an organic solvent to prepare solifenacin. The method is advantageous in that high-purity solifenacin or a salt thereof can be simply and efficiently prepared with high yield using a novel intermediate.
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Paragraph 0084 - 0108

(2015/04/28)

Process for the Preparation of Solifenacin and Salts Thereof
The invention provides a new process for the preparation of solifenacin or a pharmaceutically acceptable acid addition salt thereof, comprising reacting (R)-quinuclidin-3-yl phenethylcarbamate with benzaldehyde in the presence of an acid to obtain a diast
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(2014/08/19)

An improved process for the preparation of highly pure solifenacin succinate via resolution through diastereomeric crystallisation
An improved process for the preparation of solifenacin succinate (1) involving resolution through diastereomeric crystallization is described. (1S)-IQL derivative (5) is esterified to form (1S)-ethoxycarbonyl IQL derivative (6) which is condensed with (RS)-3-quinuclidinol (7) to form a solifenacin diastereomeric mixture (8); this is subjected to resolution through diastereomeric crystallization to produce solifenacin succinate (1), which is used for the treatment of an overactive bladder.
Trinadhachari, Ganala Naga,Kamat, Anand Gopalkrishna,Venkata Balaji, Boddu,Prabahar, Koilpillai Joseph,Naidu, Kolukuluru Mohan,Babu, Korupolu Raghu,Sanasi, Paul Douglas
p. 934 - 940
(2014/10/15)

A PROCESS FOR THE PREPARATION OF SOLIFENACIN OR A SALT THEREOF
The present invention relates to an improved process for the preparation of Solifenacin or its salt of formula I, more particularly the present invention relates to an economically viable and industrially advantageous process for the preparation of highly pure Solifenacin or its salt of formula I.
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Page/Page column 8

(2014/01/18)

PROCESS OF PREPARING SOLIFENACIN OR SALT THEREOF, AND NOVEL INTERMEDIATE USED IN THE PROCESS
Disclosed herein is a method of preparing solifenacin or a salt thereof, including the steps of: (a) reacting (R)-quinuclidinol with bis(pentafluorophenyl)carbonate in an organic solvent to prepare a solifenacin intermediate,(3R)-1-azabicyclo[2,2,2]oct-3-yl pentafluorophenylcarbonate, and (b) reacting the solifenacin intermediate with (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline in an organic solvent to prepare solifenacin. The method is advantageous in that high-purity solifenacin or a salt thereof can be simply and efficiently prepared with high yield using a novel intermediate.
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Paragraph 147-154

(2013/10/21)

NOVEL PROCESS FOR THE PREPARATION OF SOLIFENACIN SUCCINATE
The present invention relates to a process for the preparation of Solifenacin succinate by condensing a compound of formula (IVb) with (RS)-3-quinuclidinol, wherein, R represents methyl, ethyl, isopropyl; to produce a diastereomeric mixture of (1S)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylic acid (3RS)-1-azabicyclo[2.2.2]oct-3-yl ester, which is treated with succinic acid in a solvent or mixture of solvents to produce optically pure Solifenacin succinate, Formula (X).
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Paragraph 0038; 0039; 0040; 0041

(2013/05/22)

PROCESS FOR THE PREPARATION OF SOLIFENACIN AND SALTS THEREOF
The invention provides a new process for the preparation of solifenacin or a pharmaceutically acceptable acid addition salt thereof, comprising reacting (R)- quinuclidin-3-yl phenethylcarbamate with benzaldehyde in the presence of an acid to obtain a diasteroisomeric mixture (S,R)-((R)-quinuclidin-3-yl) 1 -phenyl-3,4- dihydroisoquinoline-2(1 H)-carboxylate of formula (IV) which can be resolved and the solifenacin or a pharmaceutically acceptable acid addition salt thereof recovered. The invention also provides the new key intermediate (R)-quinuclidin-3-yl phenethylcarbamate involved in the process. Further the invention provides a method for the transformation of (R)-((R)-quinuclidin-3-yl) 1 -phenyl-3,4- dihydroisoquinoline-2(1 H)-carboxylate into a diasteroisomeric mixture (S,R)-((R)- quinuclidin-3-yl) 1 -phenyl-3,4-dihydroisoquinoline-2(1 H)-carboxylate.
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(2013/02/28)

SOLIFENACIN SALTS
The invention concerns fumarate salts of solifenacin, as well as pharmaceutical compositions comprising fumarate salts of solifenacin. The invention furthermore concerns a process for preparing solifenacin and salts thereof. The fumarate salt provides improved properties over the known solifenacin salts, especially in terms of its stability. The novel process for its preparation is furthermore improved over known processes for preparing solifenacin in that it provides a higher yield and recovers a greater amount of starting material.
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(2012/02/01)

NOVEL PROCESS FOR THE PREPARATION OF SOLIFENACIN SUCCINATE
The present invention relates to a process for the preparation of Solifenacin succinate by condensing a compound of formula (IVb) with (RS)-3-quinuclidinol, wherein, R represents methyl, ethyl, isopropyl; to produce a diastereomeric mixture of ( 1S)-3,4-dihydro- 1 -phenyl-2( 1 H)-isoquinolinecarboxylic acid (3RS)- 1 - azabicyclo[2.2.2]oct-3-yl ester, which is treated with succinic acid in a solvent or mixture of solvents to produce optically pure Solifenacin succinate, Formula (X).
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(2012/01/14)

A PROCESS FOR THE PREPARATION AND PURIFICATION OF SOLIFENACIN SALTS
The invention relates to a preparation and purification processes of solifenacin salts, particularly to a crystallization process of solifenacin succinate, leading to high purity of the obtained product as well as to the desired average particle size and
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Page/Page column 22

(2011/02/24)

PROCESS FOR THE PREPARATION OF SOLIFENACIN AND SOLIFENACIN SUCCINATE
A process for the preparation of solifenacin wherein all the reaction steps, starting from (i) release of (S) -I -phenyl- 1, 2,3, 4 - tetrahydroisoquinoline from its diastereoisomeric salt with D- (-) - tartaric acid, (ii) conversion of (S) - 1 -phenyl - 1, 2, 3, 4 - tetrahydroisoquinoline into 1 - (5) -phenyl - 1, 2, 3, 4 - tetrahydroisoquinolinecarbonyl chloride in the reaction with triphosgene in the presence of pyridine to (iii) the reaction between 1- (5) -phenyl - 1, 2, 3, 4 - tetrahydroisoquinolinecarbonyl chloride and 3- (S) - quinuclidinol in the presence of sodium hydride are carried out without the isolation of intermediates in solid form and the solvents used for the reactions are aprotic solvent. Resulting solifenacin in the free base form is converted into the corresponding succinic acid salt using methods known in the art.
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Page/Page column 13

(2011/08/04)

Efficient and single pot process for the preparation of enantiomerically pure solifenacin succinate, an antimuscarinic agent
The development of an efficient and economic one-pot process, in which the configuration of the chiral centers of the starting materials is retained, for the preparation of highly pure solifenacin succinate, an antimuscarinic agent, is presented in this communication. The earlier reported processes suffer from the drawbacks of racemization and low yields due to the use of strong base, higher temperatures, and longer reaction times. The present work circumvents these issues by activating (3R)-quinuclidin-3-ol into a mixed active carbonate derivative by treating it with bis(4-nitrophenyl)carbonate. The subsequent reaction of the active carbonate with an enantiomerically pure amine without using any base at ambient temperature provided enantiomerically pure solifenacin with an overall yield of 90%. Graphical Abstract: [Figure not available: see fulltext.]
Niphade, Navnath C.,Jagtap, Kunal M.,Mali, Anil C.,Solanki, Pavankumar V.,Jachak, Madhukar N.,Mathad, Vijayavitthal T.
experimental part
p. 1181 - 1186
(2012/01/06)

METHOD FOR THE PREPARATION OF SOLIFENACIN
A method of preparing (1S)-(3R)-1-azabicyclo[2.2.2]oct-3-yl 3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate (solifenacin) or its pharmaceutically acceptable salts with high optic purity, wherein the crude solifenacin base is transformed to the hydrogen tartrate, which is then optionally transformed to another pharmaceutically acceptable salt or the base of solifenacin. A crystalline salt of solifenacin hydrogen tartrate.
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Page/Page column 3-4

(2010/06/19)

Process for the Synthesis of Solifenacin
This invention provides improved methods for making solifenacin and pharmaceutically acceptable salts thereof. The instant methods are unexpectedly advantageous in their simplicity and efficiency.
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Page/Page column 5

(2010/03/02)

A NEW METHOD FOR THE PREPARATION OF SOLIFENACIN AND NEW INTERMEDIATE THEREOF
A new method for the preparation of solifenacin by reacting quinuclidin-3-ol and bis (aryl) carbonate to form (3R)-l -azabicyclo[2.2.2]oct-3-yl 4-aryl carbonate of formula (IVa); and treating (3R)-I - azabicyclo[2.2.2]oct-3-yl 4-aryl carbonate of formula (IVa) with (1S)- I -phenyl- 1, 2, 3, 4- tetrahydroisoquinoline in an inert atmosphere to form a Solifenacin base which is converted into its pharmaceutically acceptable salts. The invention also provide new compound, (3R)-1 - azabicyclo[2.2.2]oct-3-yl 4-aryl carbonate, which is used as an intermediate for the preparation of Solifenacin base and a process for the preparation thereof.
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Page/Page column 29

(2010/10/03)

"Process for the preparation of solifenacin"
A process for the preparation of (1S,3'R)-quinielidin-3'-yl-1-phenyl-3,4-dihydro-1H-isoquinolin-2-carboxylate, namely solifenacin, comprising the reaction of a compound of formula (IV) with a compound of formula (V), as herein defined, and the subsequent reaction with 3-quinuclidinol.
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Page/Page column 6

(2009/09/05)

PROCESS FOR PREPARING CHEMICALLY AND CHIRALLY PURE SOLIFENACIN BASE AND ITS SALTS
The present invention provides improved processes for preparing chemically and chirally pure Solifenacin base. The present invention also provides for a composition comprising of a salt of Solifenacin having at least 98 % purity. The present invention also disclose certain new salts of Solifenacin as well as well as new polymorphic forms of Solifenacin hydrochloride and Solifenacin oxalate, in pure form.
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Page/Page column 41

(2009/09/04)

PROCESS FOR PREPARATION OF SOLIFENACIN AND/OR THE PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF OF HIGH PHARMACEUTICAL PURITY
A process for the preparation of solifenacin and/or the pharmaceutically acceptable salts thereof of high pharmaceutical purity is characterized in that 3-(R)-quinuclidinoloxy anion generated in situ from 3-(R)-quinuclidinol in a presence of strong base in polar organic solvent is subject to acylation with (S)-1 -phenyl-1,2,3, 4-tetrahydroisoquinolinecarbonyl chloride of chemical purity at least 98%, while maintaining constant anion excess in a reaction mixture, and after reaction completion solifenacin base is optionally transformed into solifenacin salt according to standard procedures. (S)-1-Phenyl-1,2,3,4-tetrahydroisoquinolinecarbonyl chloride of chemical purity at least 98% is obtained in a reaction of (S)-1-phenyl-1,2,3, 4- tetrahydroisoquinoline and molar excess of phosgene in a presence of tertiary aromatic amine in aromatic hydrocarbon, and isolated in a crystalline form.
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Page/Page column 12

(2009/12/27)

PROCESSES FOR SOLIFENACIN PREPARATION
Processes for preparing solifenacin comprising distilling ethanol and organic solvent from a reaction mixture and recycling the organic solvent are described. The ethanol is removed using a Dean-Stark apparatus. Also described are processes for reducing solifenacin diastereomeric and enantiomeric impurities.
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Page/Page column 16

(2009/03/07)

Process for the preparation of solifenacin
A process for the preparation of (1S,3′R)-quiniclidin-3′-yl-1-phenyl-3,4-dihydro-1H-isoquinolin-2-carboxylate, namely solifenacin, comprising the reaction of a compound of formula (IV) with a compound of formula (V), as herein defined, and the subsequent reaction with 3-quinuclidinol.
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Page/Page column 3-4

(2009/08/18)

SOLIFENACIN COMPOSITIONS
Compositions and/or formulations comprising solifenacin or a salt thereof and processes for preparing the same. Certain compositions and formulations contain a stable amorphous form of solifenacin succinate.
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(2008/12/08)

PROCESS FOR PREPARING SOLIFENACIN AND ITS SALTS
The present invention relates to solifenacin in solid form and a process for its preparation and to a process for the preparation of (1S)-1-Phenyl-1,2,3,4-tetrahydro-isoquinoline, a key intermediate in the synthesis of solifenacin and its salts.
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Page/Page column 25; 26

(2008/06/13)

A METHOD FOR THE PREPARATION OF SOLIFENACIN
A method of preparing (lS)-(3R)-l-azabicyclo[2.2.2]oct-3-yl 3,4-dihydro-l-phenyl-2(lH)- isoquinoline carboxylate (solifenacin) or its pharmaceutically acceptable salts with high optic purity, wherein the crude solifenacin base is transformed to the hydrogen tartrate, which is then optionally transformed to another pharmaceutically acceptable salt or the base of solifenacin. A crystalline salt of solifenacin hydrogen tartrate.
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Page/Page column 7-8

(2008/12/06)

Process for preparing polymorphic forms of solifenacin succinate
Polymorphic forms of solifenacin have been prepared and characterized. These polymorphic forms are particularly useful in pharmaceutical compositions.
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Page/Page column 11

(2008/12/05)

Process for the synthesis of solifenacin
The present invention provides an improved synthetic strategy for the preparation of solifenacin and pharmaceutically acceptable salts thereof.
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Page/Page column 4

(2008/12/07)

PROCESSES FOR PREPARING SOLIFENACIN
Provided are new intermediates of solifenacin and methods for their preparation, as well as methods of preparing solifenacin and solifenacin succinate.
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Page/Page column 13-14

(2010/11/27)

COMPOSITION CONTAINING SOLIFENACIN SUCCINATE
A solifenacin succinate-containing composition with less impurities which can be used as a bulk for pharmaceutical is provided. The solifenacin succinate-containing compostiion of the present invention has a reduced content of especially its optical isomers in comparison with the known compositions containing an acid addition salt of solifenacin, so that it can be used for production of a therapeutic agent containing solifenacin succinate. In addition, the above-described solifenacin succinate-containing composition can be easily produced in accordance with the production method of the present invention.
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Page/Page column 11

(2008/06/13)

SOLIFENACIN-CONTAINING COMPOSITION
To provide a novel method for producing a composition comprising solifenacin or a salt thereof, and a composition comprising solifenacin or a salt thereof as produced by the method, wherein an optionally substituted lower alkyl is added to the 2-position of the quinuclidine of solifenacin. The composition of the present invention contains a highly pure solifenacin, while the unexpected compounds specific to the method in an extremely low content, so that it has very preferable properties as a bulk for pharmaceutical products.
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Page/Page column 6

(2010/11/24)