180468-40-0

Basic information

• Product Name: (1R,3S-)Solifenacin Hydrochloride
• Synonyms: (1R,3S-)Solifenacin Hydrochloride;(1R,3S)-Solifenacin Succinate;YAUBKMSXTZQZEB-HLUKFBSCSA-N
• CAS NO: 180468-40-0
• Molecular Formula: C23H27ClN2O2
• Molecular Weight: 398.92568
• Mol File: 180468-40-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (1R,3S-)Solifenacin Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3S-)Solifenacin Hydrochloride(180468-40-0)
• EPA Substance Registry System: (1R,3S-)Solifenacin Hydrochloride(180468-40-0)

Safety Data

• Hazardous Substances Data: 180468-40-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1R,3S-)Solifenacin Hydrochloride is used as a therapeutic agent for the treatment of urinary incontinence. Its selective action on the muscarinic M3 receptors helps to reduce the symptoms of overactive bladder, providing relief and improving the quality of life for patients suffering from this condition.

Upstream product

• 774517-20-3 (3S)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate 
• 242478-37-1 solifenacin 
• 22990-19-8 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 25333-42-0 (R)-quinuclidin-3-ol 

Relevant articles and documents

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.]

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.

A PROCESS FOR THE PREPARATION OF SOLIFENACIN SALTS AND THEIR INCLUSION INTO PHARMACEUTICAL DOSAGE FORMS

The invention relates to the synthesis of solifenacin, the preparation of its salts and their inclusion into pharmaceutically acceptable dosage forms.

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.

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)