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Usage

Uses

Used in Pharmaceutical Industry:
(1R,3R)-Solifenacin Succinate 2 is utilized as a therapeutic agent for the management of overactive bladder conditions. It is particularly effective due to its ability to relax the bladder muscles, leading to a significant reduction in the frequency of urination. This application is crucial for improving the quality of life for patients suffering from such conditions, providing them with a more manageable and comfortable daily routine.

Upstream product

• 180468-42-2 (S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 25333-42-0 (R)-quinuclidin-3-ol 
• 180468-41-1 ethyl (R)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 180272-45-1 (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1619-34-7 3-quinuclidinol 
• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 180272-14-4 (S,R)-((R)-quinuclidin-3-yl) 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 552831-23-9 (R)-imidazole-1-carboxylic acid 1-azabicyclo[2.2.2]oct-3-yl ester 
• 6970-83-8 ethyl-N-(2-phenethyl)carbamate 
• 102422-37-7 N-(1H-imidazol-1-ylcarbonyl)-2-phenethylamine 
• 64-04-0 phenethylamine 
• 3278-14-6 N-phenethylbenzamide 
• 52250-50-7 1-phenyl-3,4-dihydroisoquinoline 

Downstream Products

• 865813-82-7 (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (-)-(2S,3S)-tartrate 
• 865813-72-5 (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (-)-L-phenylalaninate 
• 865813-80-5 (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate methanesulfonate 
• 865813-84-9 (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (+)-(2S,3S)-di-O-(4-methylbenzoyl)tartrate 
• 865813-77-0 (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (+)-camphor-10-sulfonate 
• 865813-76-9 (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate sebacate 
• 865813-83-8 (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (+)-(2S,3S)-di-O-benzoyltartrate 
• 1035547-81-9 (3R)-1-azabicyclo[2.2.2]oct-3-yl (1S)-3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate hydrogen L-tartrate 
• 862207-71-4 (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester succinate 
• 862207-70-3 (3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate succinate 
• 1262506-09-1 solifenacin succinate 
• 865813-73-6 (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate benzenesulfonate 
• 865862-30-2 (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate hydrobromide 
• 865813-75-8 (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate naphthalene-2-sulfonate 

Relevant academic research and scientific papers

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.

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.]

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.

PROCESS FOR THE PREPARATION OF SOLIFENACIN

A process for the preparation of (1S)-QR)-I -azabicyclo[2.2.2.]oct-3-yl 3,4-dihydro-1-phenyl- 2(1H)-isoquino-line carboxylate by reacting (1S)-alkyl 1-phenyl-1,2,3,4-tetrahydro-2-isoquinoline carboxylate with 3-(R)-quinuclidol in an inert solvent, where a primary alkyl ester of the carboxylate whose alkyl length is C1-C4 is used and the reaction is catalyzed by a non-nu-cleophilic base.

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.

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.

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.

NOVEL SALTS OF QUINUCLIDINE DERIVATIVE

There is provided an acid addition salt of (?)-(3R)-quinuclidin-3-yl(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate with an acid selected from the group consisting of (?)-(2S,3S)-tartaric acid, (+)-(2S,3S)-di-O-benzoyltartaric acid, (+)-(2S,3S)

Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists

In the course of continuing efforts to develop potent and bladder-selective muscarinic M3 receptor antagonists, quinuclidin-3-yl 1-aryl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives and related compounds were designed as conformationally restricted analogues of quinuclidin-3-yl benzhydrylcarbamate (8). Binding assays with rat muscarinic receptor subtypes revealed that the quinuclidin-3-yl 1-aryl-1,2,3,4- tetrahydroisoquinoline-2-carboxylate derivatives showed high affinities for the M3 receptor, and selectivity for the M3 receptor over the M2 receptor. Of these derivatives, (+)-(1S,3'R)-quinuclidin-3'-yl 1-phenyl-l,2,3,4-tetrahydroisoquinoline-2-carboxylate monohydrochloride (9b) exhibited almost the same inhibitory activity against bladder contraction to that of oxybutynin (1), and more than 10-fold selectivity for bladder contraction versus salivary secretion, demonstrating that 9b may be useful for the treatment of symptoms associated with overactive bladder without having side effects such as dry mouth.