262845-82-9

Usage

Uses

Used in Pharmaceutical Industry:
2-AMino-3-Methoxy-n-(phenylMethyl)propanaMide is used as an impurity in the production of Lacosamide for its anticonvulsant properties. The compound plays a role in the development and manufacturing process of Lacosamide, which is an essential medication for managing epilepsy and seizure disorders. Its presence as an impurity is closely monitored and controlled to ensure the safety and efficacy of the final drug product.
In the context of Lacosamide's production, the compound 2-AMino-3-Methoxy-n-(phenylMethyl)propanaMide is used as a reference point for quality control and purity assessment. The compound's presence in the final product is minimized through various purification and synthesis techniques to maintain the therapeutic benefits of Lacosamide while reducing potential side effects or adverse reactions.

Upstream product

• 705283-58-5 N-benzyl-2-bromo-3-methoxypropionamide 
• 1224928-22-6 N-benzyl-2-chloro-3-methoxy-propionamide 
• 474534-78-6 (S)-N-benzyl-2-amino-3-methoxypropionamide 
• 175481-26-2 2-acetamido-N-benzyl-3-methoxypropionamide 
• 100-46-9 benzylamine 
• 118790-79-7 N-benzyl-2,3-dibromopropionamide 
• 1379592-20-7 (R,S)-N-benzyl-2-benzylamino-3-methoxypropionamide 
• 1379592-18-3 N-benzyl-2-azido-3-methoxy propionamide 
• 13304-62-6 N-benzylacrylamide 
• 100-51-6 benzyl alcohol 
• 160769-20-0 (R,S)-N-benzyl 2-N-(benzyloxycarbonyl)amino-3-hydroxypropionamide 
• 388619-59-8 (R)-N-BENZYL 2-(CARBOBENZYLOXYAMINO)-3-METHOXYPROPIONAMIDE 

Downstream Products

• 175481-26-2 2-acetamido-N-benzyl-3-methoxypropionamide 
• 1379592-19-4 2-amino-N-benzyl-3-methoxypropionamide monooxalate 
• 175481-36-4 lacosamide 
• 175481-36-4 (2S)-2-(acetylamino)-N-benzyl-3-methoxypropanamide 
• 1318767-66-6 C₈H₇ClO₃*C₁₁H₁₆N₂O₂ 
• 1609160-80-6 (R)-N-benzyl-2-amino-3-methoxypropanamide N-formyl-L-leucine salt 
• 196601-69-1 (R)-2-amino-N-benzyl-3-methoxypropanamide 
• 388619-62-3 3-benzyl-5-methoxymethyl-2-thioxo-imidazolidin-4-one 

Relevant academic research and scientific papers

Synthetic route of lacosamide

The invention discloses a new synthesis route of lacosamide. The new synthesis route comprises the following steps: taking glycine ethyl ester hydrochloride as an initial raw material to react with methylbenzene, benzophenone and p-toluenesulfonic acid to obtain a compound of formula M1; reacting the compound of formula M1 with Xmethyl methyl ether to generate a compound of formula M2; reacting the compound of formula M2 with benzylamine under the catalytic action of sodium ethoxide to generate a compound of formula M3; reacting the compound of formula M3 under the action of acid to generate acompound of formula M4; reacting the compound of formula M4 with Ltartaric acid to generate a compound of formula M5; and enabling the compound of formula M5 to react with acetic anhydride to generate the lacosamide compound. The synthesis route has the advantages that the atom economy is high, the use of isopropyl chloroformate highly toxic products for preparing amide is avoided, the use of methylation reagents methyl iodide or dimethyl sulfate is avoided, the yield is high, and the like.

NEW PROCESS

There is provided a process for the preparation of Lacosamide in a particular polymorphic form, which process involves the isolation of a salt of formula I : according to the methods defined in the application.

PROCESS FOR THE PREPARATION OF LACOSAMIDE

A novel process for the synthesis of Lacosamide using D,L-serine as starting material is described, where the methylation reaction of hydroxyl is carried out using an inexpensive base such as NaOH and an inexpensive alkylating agent, non-toxic and non-car

PROCESS FOR THE PREPARATION OF LACOSAMIDE

There is provided a process for the preparation of Lacosamide (which is a useful medicament) of formula I, which comprises an enantioselective enzymatic acylation.

Primary amino acid derivatives: Compounds with anticonvulsant and neuropathic pain protection activities

Pharmacological management remains the primary method to treat epilepsy and neuropathic pain. We have advanced a novel class of anticonvulsants termed functionalized amino acids (FAAs). In this study, we examine FAA derivatives from which the terminal acetyl moiety was removed and termed these compounds primary amino acid derivatives (PAADs). Twenty-seven PAADs were prepared; the central C(2) R-substituent was varied, including C(2) stereochemistry, and the compounds were tested in rodent models of seizures and neuropathic pain. C(2)-Hydrocarbon N-benzylamide PAADs were potent anticonvulsants and excellent anticonvulsant activity (mice, ip; rat, po) was observed for C(2) R-substituted PAADs in which the R group was ethyl, isopropyl, or tert-butyl, and the C(2) stereochemistry conformed to the d-amino acid configuration ((R)-stereoisomer). These values surpassed the activities of several clinical antiepileptic drugs. The C(2) (R)-ethyl and C(2) (R)-isopropyl PAADs also displayed excellent activities in the mouse (ip) formalin neuropathic pain model. Significantly, unlike the FAA structure-activity relationship, PAAD anticonvulsant activity increased upon substitution of a methylene unit for a heteroatom in the R-substituent that was one atom removed from the C(2) site, suggesting that these PAADs function by a different pathway than FAAs.

NOVEL PROCESS FOR THE PREPARATION OF AMINO ACID DERIVATIVES

The present patent application relates to an alternative process for the preparation of amino derivatives. In particular, the present application relates to an improved process for the manufacture of Lacosamide (LCM), (R)-2-acetamido-N-benzyl-3-methoxypropion-amide, which is useful as an anticonvulsive drug. In a particular aspect, the present invention relates to a process of manufacture of optically enriched (R)-2-acetamido-N-benzyl-3-methoxypropion-amide (I) comprising resolution of 2-acetamido-N-benzyl-3-methoxypropion-amide (II).

Design and evaluation of affinity labels of functionalized amino acid anticonvulsants

Studies have shown that functionalized amino acids (FAA) exhibit outstanding activity in the maximal electroshock-induced seizure (MES) test in rodents. Affinity labels patterned in part after the potent antiepileptic (R)-N-benzyl-2-acetamido-3-methoxypropionamide ((R)-2) have been prepared as mechanistic probes to learn the pharmacological basis for FAA function. The chemical reactivity of the affinity labels with nucleophiles was assessed, and the labels were evaluated in in vitro radioligand assays and in the MES tests in rodents. The affinity labels did not bind to receptors known to effect seizure spread. Three affinity labels, (R,S)-N-benzyl-2-acetamido-6-isothiocyanatohexanamide ((R,S)-5), (R)-N-(4-isothiocyanatobenzyl)-2-acetamido-3-methoxypropionamide ((R)-6), and (R)-N-(3-isothiocyanatobenzyl)-2-acetamido-3-methoxy-propionamide ((R)-7), possessed excellent in vivo anticonvulsant activity and exhibited maximal activity at later time periods than typically observed for FAA. The anticonvulsant activity of 6 and 7 resided primarily in the (R)-enantiomer and the activity of (R)-6 and (R)-7 in rats (po) exceeded that of phenytoin. The chemical properties, pharmacological profile, and marked stereospecificity associated with 6 and 7 anticonvulsant activity make these compounds useful pharmacological tools for the study of the mode of action of FAA.

Functionalized amino acid anticonvulsants: Synthesis and pharmacological evaluation of conformationally restricted analogues

Proven conformationally restricted analogues of anticonvulsant functionalized amino acids (FAAs) were prepared using short-range cyclizations and evaluated in pharmacological assays providing new information concerning the structural requirements for FAA function.

Anticonvulsant enantiomeric amino acid derivatives

The present invention is directed to a compound in the R configuration about the asymmetric carbon in the following formula: STR1 pharmaceutical compositions containing same and the use thereof in treating CNS disorders in animals.