104632-28-2

Basic information

• Product Name: (R)-Pramipexole
• Synonyms: (R)-4,5,6,7-Tetrahydro-N6-propyl-2,6-benzothiazolediamine;(R)-Pramipexole;R-(+)-Pramipexole;(R)-4,5,6,7-Tetrahydro-N6-propyl-2,6-benzothiazolediamine Dihydrochloride;(R)-Pramipexole Dihydrochloride;R-(+)-Pramipexole Dihydrochloride;Pramipexole Related Compound D (25 mg) ((R)-2-Amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole);DexpraMipexole
• CAS NO: 104632-28-2
• Molecular Formula: C₁₀H₁₇N₃S
• Molecular Weight: 211.33
• Product Categories: All Inhibitors;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Chiral Reagents
• Mol File: 104632-28-2.mol

Chemical Properties

• Melting Point: 270-272°C
• Boiling Point: 378.0±42.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Sparingly, Sonicated), Water (Slightly)
• PKA: 9.47±0.20(Predicted)
• CAS DataBase Reference: (R)-Pramipexole(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Pramipexole(104632-28-2)
• EPA Substance Registry System: (R)-Pramipexole(104632-28-2)

Safety Data

• Hazardous Substances Data: 104632-28-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-Pramipexole is used as an antiparkinsonian agent for the treatment of Parkinson's disease. It functions as a dopamine-D2-receptor agonist, helping to alleviate symptoms associated with the disorder by compensating for the reduced levels of dopamine in the brain.
Additionally, due to its distinct pharmacokinetics and pharmacodynamics compared to the racemic mixture or the (S)-enantiomer, (R)-Pramipexole may offer advantages in terms of efficacy, safety, and reduced side effects, making it a valuable compound for further research and development in the pharmaceutical industry.

Upstream product

• 106006-85-3 (+)-2-amino-6-propionamidotetrahydrobenzothiazole 
• 106006-83-1 2,6-diamino-4,5,6,7-tetrahydro-benzthiazole 
• 106092-11-9 (R)-4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-2,6-diamine 
• 104617-86-9 2-amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole 
• 1332723-78-0 (R)-(+)-2-amino-4,5,6,7-tetrahydro-6-(n-propylamino)benzothiazole p-toluenesulfonic acid 
• 147-71-7 D-tartaric acid 

Downstream Products

• 104632-27-1 (R)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine dihydrochloride 
• 1026084-24-1 (+)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-(2-methoxyphenyl)piperazin-1-yl)ethanone 
• 1026084-21-8 (+)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-phenylpiperazin-1-yl)ethanone 
• 1026084-25-2 (+)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethanone 

Relevant articles and documents

IMPROVED SYNTHESIS OF AMINE SUBSTITUTED 4,5,6,7-TETRAHYDROBENZOTHIAZOLE COMPOUNDS

The present invention is related to an improved process for the preparation of amino- substituted 4,5,6,7-tetrahydrobenzothiazole compounds of formula I, such as the compound 2- amino-4,5,6,7-tetrahydro-6-(n-propylamino)benzothiazole. The invention furthe

COMPOSITIONS AND METHODS OF USING (R)-PRAMIPEXOLE

Pharmaceutical compositions of (R)-pramipexole and one or more secondary therapeutic agents such as, for example, dopamine agonists, dopaminergic agonists, COMT inhibitors, MOA inhibitors, excitatory amino acid antagonists, growth factors, neurotrophic factors, antioxidants, anti-inflammatory agents, immunomodulators, anti-glutamatergics, ion channel blockers, α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists, heat shock protein inducers/ protein disaggregators and downregulators, monoamine oxidase type B (MOAB) inhibitors, multi-target agents, kinase inhibitors, Bcl inducers, histone deacetylase (HDAC) mediators, glial modulators, mitochondrial energy promoting agents, myostatin inhibitors, caspase inhibitors and combinations thereof or those related to mitochondrial dysfunction or increased oxidative stress are disclosed.

METHOD FOR THE RESOLUTION OF 2-AMINO-6-PROPYLAMINO-4,5,6,7-TETRAHYDROBENZOTHIAZOL AND INTERMEDIATE COMPOUNDS

The invention relates to a novel method for the resolution of the racemic mixture of compound (R,S)-2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole, or the enrichment of same with in one of its enantiomers, and to intermediate compounds which can be used to perform said method.

NOVEL PROCESS

A novel process for the preparation of S(-)-2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole (pramipexole).

PROCESS FOR PREPARING CHIRALLY PURE 2-AMINO-6-(ALKYL)AMINO-4,5,6,7-TETRAHYDROBENZOTHIAZOLES BY LIQUID CHROMATOGRAPHIC RESOLUTION

Processes for obtaining single enantiomers of 2-amino-6-(alkyl)amino-4,5,6,7-tetrahydrobenzothiazoles by liquid chromatography are disclosed.

Dopamine autoreceptor agonists: Resolution and pharmacological activity of 2,6-diaminotetrahydrobenzothiazole and an aminothiazole analogue of apomorphine

The enantiomers of the aminothiazole analogues of the known dopaminergic agonists apomorphine (1) and 2-aminohydroxytetralin (2) have been prepared. The absolute configurations of the enantiomers of 2,6-diaminotetrahydrobenzothiazole have been established by X-ray crystallographic analysis. Dopamine (DA) autoreceptor agonist activities of the compounds were evaluated. Testing revealed (-)-5, the S enantiomer, to be the most active compound tested (inhibition of GBL accelerated dopamine synthesis and inhibition of α-methyltyrosine-induced decline of DA). In addition (-)-5 does not exhibit stereotyped behavior, suggesting a pronounced selectivity for DA autoreceptors.