718635-93-9

Usage

Uses

Used in Neurological Disorders:
Tetrabenazine is used as a dopamine-depleting medication for the treatment of chorea in Huntington's disease. It helps to alleviate the involuntary movements and motor symptoms associated with the condition by reducing the levels of dopamine in the brain.
Used in Other Hyperdopaminergic Conditions:
Although primarily used for Huntington's disease, Tetrabenazine has also shown potential in the treatment of other hyperdopaminergic conditions, such as tardive dyskinesia, Tourette syndrome, and some cases of dystonia. Its ability to deplete dopamine makes it a candidate for managing symptoms related to excessive dopamine activity in these disorders.

Upstream product

• 67-56-1 methanol 
• 89929-27-1 2-Oxo-3-isobutyl-9,10-dihydroxy-1,2,3,4,6,7-hexahydro-11bH-benzochinolizin 
• 20232-39-7 3,4-dihydro-6,7-dimethoxyisoquinoline hydrochloride 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 14301-36-1 N-[2-(3,4-dimethoxyphenyl)ethyl]formamide 
• 110-12-3 5-Methyl-2-hexanone 
• 91342-74-4 3-[(dimethylamino)methyl]-5-methylhexan-2-one 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 1069-62-1 trimethyl[2-(2-methylpropyl)-3-oxobutyl]azanium iodide 

Downstream Products

• 100322-43-8 3-isobutyl-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-benzo[a]quinolizine-2-one 
• 3466-75-9 Dihydrotetrabenazine 
• 924854-62-6 (2R,3S,11bS)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol 
• 924854-60-4 (+)-β-DHTBZ 
• 3466-75-9 2β-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine 
• 1026016-84-1 (3S,11bS)-tetrabenazine 
• 1223399-57-2 (3R,11bR)-tetrabenazine D-camphorsulfonate 
• 1026016-83-0 ((3R,11bR)-3-isobutyl-9.10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one) 
• 1223399-61-8 C₁₀H₁₆O₄S*C₁₉H₂₇NO₃ 
• 1639208-54-0 (2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-yl (S)-2-amino-3-methylbutanoate di(4-methylbenzenesulfonate) 
• 862377-31-9 (2R,3S,11bR)-1,3,4,6,7,11b-hexahydro-9,10-methoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol 
• 862377-27-3 (2S,3S,11bR)-1,3,4,6,7,11b-hexahydro-9,10-methoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol 

Relevant academic research and scientific papers

PROCESSES FOR THE SYNTHESIS OF VALBENAZINE

The present application relates to processes for making (2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-yl (S)-2-amino-3-methylbutanoate di(4-methylbenzenesulfonate), which is an inhibitor of vesicular monoamine transporter 2 (VMAT2) useful in the treatment of hyperkinetic movement disorders such as tardive dyskinesia (TD).

Method for preparing tetrabenazine (by machine translation)

The invention relates to a preparation method, and belongs to the field of pharmacy technology. The preparation method provided by the invention comprises: a novel ester compound is subjected to hydrolysis reaction under basic conditions, so as to prepare the tetrabenazine. The method provided by the invention can obtain a high-purity product, and is simple, efficient, economical, controllable in intermediate quality, and suitable for industrial production. (by machine translation)

Synthetic method for tetrabenazine and intermediate of tetrabenazine

The invention discloses a simple and effective method for synthesizing tetrabenazine (cis-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a]quinolizin-2-one) and an intermediate of the tetrabenazine. The method comprises the following steps: firstly, paraformaldehyde, dimethylamine hydrochloride and 5-methyl-2-hexanone are taken as raw materials to synthesize a key intermediate 3-dimethylaminomethyl-5-methyl-2-hexanone; secondly, a crude product is effectively optimized by using simple chemical purification operation to obtain a key intermediate with higher purity; and finally, water is taken as a solvent, under the action of a catalyst, the purified key intermediate and 6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride are subjected to condensation to obtain a tetrabenazine crude product, and recrystallization is performed to obtain the tetrabenazine product, wherein the HPLC purity is greater than 99.5%. According to the method provided by the invention, the key intermediate with higher purity can be obtained by the simple chemical raw materials through synthesis and purification, and therefore the tetrabenazine product with good purity is further obtained; and the raw materials used in the method are easy to obtain, the operation is simple, special equipment is not needed, the yield is higher, and the obtained tetrabenazine has higher purity.

NOVEL PROCESS FOR PREPARATION OF TETRABENAZINE AND DEUTETRABENAZINE

The present invention provides process for preparation of dihydroxy benzoquinoline compound (III) comprising reacting dihydroxy isoquinoline compound (IV) or a salt thereof with (2-acetyl-4-methyl-pentyl)-trimethyl-ammonium iodide (V) and further 5 converting it to tetrabenazine (I) and deutetrabenazine (II).

SYNTHETIC METHODS FOR PREPARATION OF (S)-(2R,3R,11bR)-3-ISOBUTYL-9,10-DIMETHOXY-2,3,4,6,7,11b-HEXAHYDRO-1H-PYRIDO[2,1-a]ISOQUINOLIN-2-YL 2-AMINO-3-METHYLBUTANOATE DI(4-METHYLBENZENESULFONATE)

Provided herein are processes for the preparation of (S)-(2R,3R,11bR-3-isobuty-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-yl 2-amino-3-methylbutanoate di(4-methylbenzenesulfonate), or a solvate, hydrate, or polymorph thereof.

Synthesis of (±)-Tetrabenazine by Visible Light Photoredox Catalysis

(±)-Tetrabenazine was synthesized in six steps from commercially available compounds. The key cyclization substrate was assembled rapidly via Baylis-Hillman and aza-Michael reactions. Annulation of the final ring was achieved through visible light photocatalysis, wherein carbon-carbon bond formation was driven by the oxidation of a tertiary amine. Solvent played a critical role in the photoredox cyclization outcome, whereas methanol led to a mixed ketal, acetonitrile/water (10:1) gave direct cyclization to (±)-tetrabenazine and occurred more rapidly.

METHOD OF PREPARING TETRABENAZINE AND DIHYDROTETRABENAZINE

The present invention relates to a method for preparing tetrabenazine (TBZ) and dihydrotetrabenazine (DTBZ), and more specifically to a method for preparing tetrabenazine (TBZ) and dihydrotetrabenazine (DTBZ) by using simple and short reaction processes o

PROCESS FOR PREPARING TETRABENAZINE

A substantially pure crystalline form A of tetrabenazine compound of structural formula I and processes for the preparation thereof is provided.

Synthesis of 3H-labeled Tetrabenazine (TBZ)

Tetrabenazine (TBZ) (1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2- methylpropyl)-2H-benzo[a]quinolin-2-one), a vesicular monamine transporter 2 inhibitor, was prepared as a tritium-labeled compound with high specific activity and radiochemical purity. Catalytic hydrogenation of a precursor with the terminal double bond was used to introduce the tritium. This method provides tritium-labeled TBZ with high specific activity and radiochemical purity, which allow the further investigation of a TBZ in the neurological field.

Preparation and characterization of tetrabenazine enantiomers against vesicular monoamine transporter 2

As a clinical medication for the treatment of hyperkinetic movement disorders, in conditions such as Huntington's disease, tetrabenazine (TBZ) has always been used in its racemic form. To establish whether or not its beneficial therapeutic actions are enantiospecific, a practical total synthetic route was developed to yield each enantiomeric form to allow their chemical and pharmacological characterization. We briefly summarize the total synthesis of TBZ and report a detailed procedure for resolution of TBZ into its enantiomers, (+)-TBZ and (-)-TBZ. This allowed determination of the optical rotation and absolute configurations of each TBZ enantiomer, based on X-ray crystallographic analysis, together with characterization of their inhibitory action at the vesicular monoamine transporter 2, where (+)-TBZ proved 3-fold more active than (-)-TBZ.