139264-82-7

Basic information

• Product Name: 4-[3-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLMETHYL]-OXAZOLIDIN-2-ONE
• Synonyms: 4-[3-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLMETHYL]-OXAZOLIDIN-2-ONE
• CAS NO: 139264-82-7
• Molecular Formula: C16H21N3O2
• Molecular Weight: 287.36
• Mol File: 139264-82-7.mol

Chemical Properties

• Boiling Point: 563.3±38.0 °C(Predicted)
• Appearance: /
• Density: 1.217±0.06 g/cm3(Predicted)
• PKA: 12.57±0.40(Predicted)
• CAS DataBase Reference: 4-[3-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLMETHYL]-OXAZOLIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[3-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLMETHYL]-OXAZOLIDIN-2-ONE(139264-82-7)
• EPA Substance Registry System: 4-[3-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLMETHYL]-OXAZOLIDIN-2-ONE(139264-82-7)

Safety Data

• Hazardous Substances Data: 139264-82-7(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 139264-15-6 (S)-2-<5-<(2-oxo-1,3-oxazolidin-4-yl)methyl>-1H-indol-3-yl>ethylamine 
• 1116-77-4 4,4-diethoxy-N,N-dimethyl-1-butanamine 
• 139264-57-6 (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one hydrochloride 
• 1456594-06-1 ethyl 3-(2-dimethylaminoethyl)-5-[(4R)-2-oxooxazolidin-4-ylmethyl]-1H-indole-2-carboxylate 
• 152305-23-2 (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 19718-92-4 4-(N,N-dimethylamino)butyraldehyde dimethyl acetal 
• 187975-62-8 (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one 
• 139264-19-0 Zolmitriptan hydrochloride 
• 868622-23-5 ethyl (S)-3-(2-(dimethylamino)ethyl)-5-((2-oxazolidin-4-yl)methyl)-1H-indolecarboxylate hydrochloride 
• 191864-24-1 ethyl 3-(2-dimethylaminoethyl)-5-[(4S)-2-oxooxazolidin-4-ylmethyl]-1H-indole-2-carboxylate 
• 659738-69-9 (S)-3-(2-dimethylaminoethyl)-5-[2-oxo-1,3-oxazolidin-4-ylmethyl]-1H-indol-2-carboxylic acid 

Relevant articles and documents

PROCESS FOR PREPARATION OF ZOLMITRIPTAN

The present invention provides a convenient and industrially viable process for preparation of Zolmitriptan (I) having desired purity. The invention specifically relates to a method for isolating (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one hydrochloride (IIIa) of desired purity by separating the undesired inorganic side products such as stannous hydroxide by manipulation of pH at different stages and finally treating with N,N-dimethylamino butyraldehyde diethyl acetal in an acidic medium to provide Zolmitriptan (I) conforming to regulatory specifications.

Convenient and industrially viable process for preparation of zolmitriptan

The present invention provides a convenient and industrially viable process for preparation of zolmitriptan. The invention specifically relates to a method for obtaining (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one hydrochloride of desired purity by separation and isolation in a particular pH range to give higher yield and purity.

Synthesis of zolmitriptan and related substances

Efficient and cost-effective synthesis of Zolmitriptan 1 employing Japp-Klingemann reaction and a new robust purification strategy is described.

PROCESS FOR THE PREPARATION OF ZOLMITRIPTAN, SALTS AND SOLVATES THEREOF

The present invention relates to an improved process for the preparation of the active pharmaceutical ingredient zolmitriptan. In particular, it relates to an efficient process for the preparation of zolmitriptan and its pharmaceutically acceptable salts and solvates.

ORALLY DISINTEGRATING TABLETS OF ZOLMITRIPTAN AND PROCESS FOR PREPARING THE SAME

Silicon dioxide free orally disintegrating tablet formulations of zolmitriptan or a pharmaceutically acceptable salt thereof having magnesium carbonate heavy and sodium stearyl fumarate with one or more pharmaceutically acceptable excipients and a process for preparing such a formulation and its use in the treatment of migraines.

ENANTIOSELECTIVE PROCESS FOR THE PREPARATION OF ZOLMITRIPTAN

An enantioselective process for preparing zolmitriptan, (S)-4-{[3-[2-(dimethylamine)ethyl]-1H-indol-5-yl]methyl}-2-oxazolidinone), by asymmetric hydrogenation of (Z)-2-(acetylamino)-3-{[3-N,N-(dimethylamine)ethyl)-1H-indol-5-yl]-2-propenoic acid methyl ester in the presence of hydrogen and an enantioselective chiral phosphine transition metal catalyst.

POLYMORPHS OF ZOLMITRIPTAN

The present invention provides a novel isopropyl acetate solvate form of zolmitriptan, and a process for its preparation thereof. The present invention also provides a process for preparation of zolmitriptan polymorph A. Thus, for example, zolmitriptan isopropanol solvate was dissolved in isopropyl acetate at 25 deg C, the contents were heated to reflux for 30 minutes and the separated solid was filtered, washed with isopropyl acetate to give zolmitriptan isopropyl acetate solvate.

PROCESS FOR THE PREPARATION OF ZOLMITRIPTAN, SALTS AND SOLVATES THEREOF

The present invention relates to an improved process for the preparation of the activepharmaceutical ingredient zolmitriptan. In particular, it relates to an efficient process for the preparation of zolmitriptan and its pharmaceutically acceptable salts and solvates.

A METHOD FOR THE PREPARATION OF ZOLMITRIPTAN

A method for the preparation of zolmitriptan or its pharmaceutically acceptable salts, comprising isolation of a crystalline salt of zolmitriptan, its optional re-purification and conversion to the substance of formula (III). Zolmitriptan hydrochloride in the crystalline state.

A METHOD FOR THE PREPARATION OF ZOLMITRIPTAN

In the preparation of zolmitriptan of formula III the reduction of the diazonium salt to (5)-4-(4- hydrazinobenzyl)-l,3-oxazolidin-2-one of formula IV is performed in a more concentrated mixture and by the effect on an alkali metal disulphite, preferably sodium disulphite. A zolmitriptan toluene solvate, characterized by a toluene content of 9 to 14 % by weight according to the gas chromatography determination and by a maximum of the corresponding mass loss at temperatures of about 111°C in the gravimetric analysis record. A zolmitriptan toluene solvate, showing strong Raman bands at the wave numbers of 1443 and 1354 cm-1, characteristic for the crystal lattice of zolmitriptan with built-in toluene, and further marked bands at 1004 and 786 cm-1, characteristic for toluene.