55375-92-3

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one is used as an intermediate in the synthesis of (R)-Praziquantel-d11 (P702102), an important compound with demonstrated antiparasitic activity. (R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one is particularly effective against juvenile Schistosoma mansoni infestations in mice, exhibiting both in vitro and in vivo inhibition of the parasite. The development of (R)-Praziquantel-d11 as a pharmaceutical agent could lead to new treatments for parasitic infections, offering a valuable contribution to global health.
Used in Chemical Synthesis:
Due to its unique structure, (R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one may also find use in the chemical synthesis industry. It could serve as a key building block or precursor for the development of novel compounds with various applications, such as pharmaceuticals, agrochemicals, or materials science. (R)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one's structural diversity and potential for functionalization make it an attractive candidate for further research and development in these fields.

Upstream product

• 99700-58-0 C₂₂H₂₁F₃N₂O₃ 
• 61196-37-0 2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 
• 1558003-68-1 (R)-(-)-2-((S)-2-(6-methoxynaphthalen-2-yl)propanoyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 55268-74-1 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one 
• 1622136-46-2 (R)-praziquanamine dibenzoyl-L-tartaric acid salt 
• 1622136-46-2 (R)-praziquanamine-hemi-dibenzoyl-L-tataric acid salt 
• 210223-97-5 2-[(2,2-dimethoxyethyl)amino]-N-(2-phenylethyl)acetamide hydrochloride 
• 64-04-0 phenethylamine 
• 13156-95-1 2-chloro-N-phenethylacetamide 
• 99746-73-3 (S)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 55375-96-7 C₁₇H₁₈N₂O 
• 106181-28-6 ethyl (+/-)-1,2,3,4-tetrahydroisoquinoline-1-carboxylate 

Downstream Products

• 57452-32-1 (-)-2-(4-oxocyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 99780-88-8 (-)-1,3,4,6,7,11b-Hexahydro-2H-pyrazino<2,1-a>isochinolin 
• 99780-87-7 (+)-1,3,4,6,7,11b-Hexahydro-2H-pyrazino<2,1-a>isochinolin 
• 135526-78-2 (-)-Praziquantel 
• 1558003-78-3 (R)-(-)-2-(cis-4-(benzyloxy)cyclohexanecarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 134924-69-9 (-)-2-(4-cis-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 1558003-79-4 (R)-(-)-2-(trans-4-(benzyloxy)cyclohexanecarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 1609986-44-8 C₁₉H₁₉N₃O₂ 
• 1609979-49-8 C₂₈H₂₂F₃N₅O₃ 
• 1609979-50-1 C₃₁H₂₄F₃N₅O₃ 
• 1609986-43-7 C₁₉H₁₇N₃O₄ 
• 1609979-51-2 C₂₃H₂₃N₃O₂ 
• 1609979-52-3 C₃₄H₄₀N₆O₄ 
• 1399880-38-6 (R)-2-(cyclohexane-d11-carbonyl)-2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 

Relevant academic research and scientific papers

Combining Incompatible Processes for Deracemization of a Praziquantel Derivative under Flow Conditions

An efficient deracemization method for conversion of the racemate to the desirable (R)-enantiomer of Praziquantel has been developed by coupling incompatible racemization and crystallization processes. By a library approach, a derivative that crystallizes as a conglomerate has been identified. Racemization occurs via reversible hydrogenation over a palladium on carbon (Pd/C) packed column at 130 °C, whereas deracemization is achieved by alternating crystal growth/dissolution steps with temperature cycling between 5–15 °C. These incompatible processes are combined by means of a flow system resulting in complete deracemization of the solid phase to the desired (R)-enantiomer (98 % ee). Such an unprecedented deracemization by a decoupled crystallization/racemization approach can readily be turned into a practical process and opens new opportunities for the development of essential enantiomerically pure building blocks that require harsh methods for racemization.

Preparation method of (R)-praziquantel amine salt, and preparation method of levopraziquantel

The invention relates to a preparation method of (R)-praziquantel amine salt, and a preparation method of levopraziquantel. The (R)-praziquantel amine salt is prepared through a reaction of racemic praziquantel amine and a chiral resolution reagent in a solvent, and the chiral resolution reagent is one or more of (R)-ibuprofen, (R)-naproxen and (R)-phenethylsulfonic acid. The preparation methods have the advantages of easily available raw materials, simple process, short preparation cycle, low cost, and stability, low price and easiness in recovery of the chiral resolution reagent,.

One-pot palladium-catalyzed racemization of (S)-praziquanamine: A key intermediate for the anthelmintic agent (R)-praziquantel

An one-pot palladium-catalyzed procedure for racemization of (S)-praziquanamine, which is the undesired enantiomer and produced during the resolution step for preparing the anthelmintic drug (R)-praziquantel, has been developed through dehydrogenation of

METHOD FOR THE PRODUCTION OF PRAZIQUANTEL AND PRECURSORS THEREOF

The present invention relates to methods for the production of enantiopure or enantioenriched Praziquantel precursors and to methods for the production of enantiopure or enantioenriched Praziquantel comprising the methods for the production of the Praziquantel precursors. The present invention further relates to compounds or intermediates useful in such methods.

Optically active [...][...] and the corresponding method for the preparation of the

The invention provides a preparation method of pyrazino amine salt with optical activity. The preparation method is characterized in that pyrazino amine salt is prepared through the reaction of racemic pyrazino amine and dibenzoyltartaric acid with optical activity in the presence of a solvent, wherein the solvent comprises more than 50% of 2-butanone in volume fraction; and dibenzoyltartaric acid with optical activity is diphenyl diketone-L-tartaric acid with optical impurity not less than 95%, or diphenyl diketone-D-tartaric acid with optical impurity not less than 95%. The invention also provides a preparation method of corresponding pyrazino amine with optical activity. The method performed for separating racemic pyrazino amine is very suitable for industrial application.

Methods of use comprising deuterated pyrazino[2,1-a]isoquinolines

This invention in one embodiment is directed to a compound of Formula Ia; where the designation (R) indicates that the designated carbon has the (R) stereochemistry; and wherein Z1 is hydrogen or fluorine; Z2 is hydrogen, deuterium,

Method for preparing (R)-praziquantel

The invention relates to a new method for preparing (R)-praziquantel. In the invention, by taking advantage of the high stereo selectivity, site selectivity and region selectivity of an enzyme, an intermediate of a pure optical and chiral (R)-praziquantel

A straightforward and efficient synthesis of praziquantel enantiomers and their 4′-hydroxy derivatives

A new method for the synthesis of praziquantel enantiomers via resolution of praziquanamine with (S)-(+)-naproxen was developed. The four 4′-hydroxy derivatives were obtained through each single praziquanamine enantiomer, coupling with cis- and trans-4-(benzyloxy)cyclohexanecarboxylic acids and subsequent hydrogenolysis for the deprotection of the 4′-OH cyclohexane residue. Additionally, the in vitro cysticidal activity of the compounds was tested, finding that (R)-(-)-praziquantel is the eutomer.

Development of chiral praziquantel analogues as potential drug candidates with activity to juvenile Schistosoma japonicum

A series of chiral praziquantel analogues were synthesized and evaluated against Schistosoma japonicum both in vitro and in vivo. All compounds exhibited low to considerable good activity in vivo. Remarkably, worm reduction rate of R-3 was 60.0% at a sing

Development and validation of process for resolution of praziquantel amine for preparation of chiral praziquantel

Investigation of the viability of scale up preparation for chiral praziquantel was included in WHO/TDR business plan. Resolution is the major strategy for preparation of single enantiomer. In this study, a stable and effective resolution approach toward the important intermediate praziquantel amine for preparation of chiral praziquantel was developed and the process was optimized to afford high ee value and good yield. The suitable HPLC method was validated for the determination of ee value of chiral praziquantel amine.