- Novel preparation method of lacosamide
-
The invention relates to a preparation method of high-purity lacosamide, and belongs to the technical field of organic synthesis. The technical problem to be solved by the invention is to provide a preparation method of lacosamide with mild reaction conditions and high optical purity. The preparation method comprises the following steps: carrying out condensation reaction on a carboxylic acid compound with a protecting group and benzylamine to generate an amide compound, carrying out deprotection under the condition of phosphoric acid, and introducing acetyl to prepare the lacosamide. The invention provides a novel industrial synthesis selection mode, the synthesis mode has the characteristics of simple process, mild reaction conditions, environmental friendliness and the like, can be used for preparing an optical high-purity target compound, and is beneficial to industrial production.
- -
-
-
- 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.
- -
-
-
- Direct, Enantioselective, and Nickel(II) Catalyzed Reactions of N-Azidoacetyl Thioimides with Trimethyl Orthoformate: A New Combined Methodology for the Rapid Synthesis of Lacosamide and Derivatives
-
A direct and highly enantioselective reaction of N-azidoacetyl-1,3-thiazolidine-2-thione with trimethyl orthoformate catalyzed by Tol-BINAPNiCl2 in the presence of TESOTf and 2,6-lutidine is reported. The heterocyclic scaffold can be easily removed by addition of a wide array of amines to give the corresponding enantiomerically pure 2-azido-3,3-dimethoxypropanamides in high yields. Appropriate manipulation of the N-benzyl amide derivative provides an efficient access to the antiepileptic agent lacosamide through a new enantioselective C?C bond-forming process. DFT computational studies uncover clues for the understanding of the remarkable stereocontrol of the addition of a nickel(II) enolate to a putative oxocarbenium intermediate from trimethyl orthoformate.
- Teloxa, Saul F.,Kennington, Stuart C. D.,Camats, Marc,Romea, Pedro,Urpí, Fèlix,Aullón, Gabriel,Font-Bardia, Mercè
-
p. 11540 - 11548
(2020/08/10)
-
- Preparation method of lacosamide
-
The invention provides a novel methylation method of a lacosamide synthesis intermediate, which comprises the following steps: methylating a compound I in a reaction solvent at a proper temperature byusing trimethyloxyonium tetrafluoroborate as a methylation reagent under alkaline condition to obtain a methylation product II. The reaction formula is shown in the specification. The method has theadvantages of mild reaction condition, simple post-treatment, green methylation reagent, no high toxicity and high reaction yield, and conforms to the safe and environment-friendly green chemical concept. The method is suitable for laboratory small-scale preparation and large-scale industrial production.
- -
-
Paragraph 0029-0030
(2020/07/02)
-
- Synthetic method of (by machine translation)
-
The synthesis method, takes ethyl acetoacetate as a starting material, as a starting raw material and reacts the compound of the formula II with trimethyl orthoformate to form the compound; of the formula III with the compound of the formula III under the action of a catalyst and a ligand H. 2 Of asymmetric hydrogenation to produce compound; of formula IV wherein the compound of formula IV is reacted with sodium azide in Schmidt rearrangement reaction to produce compound; of formula V in which compound of formula V is reacted with benzyl amine (BnNH under alkaline conditions of sodium methoxide. 2 ) The reaction scheme of the invention has the advantages. (: the economical efficiency of the atom is high, the use, of, the methyl tert-butyl carbonate is avoided, the use, of the methyl tert-butyl peroxyformate is avoided, yield is high, and the, like. (by machine translation)
- -
-
Paragraph 0032; 0035-0036; 0037; 0040-0041; 0042; 0045-0046
(2020/04/17)
-
- Enantioselective three-component Ugi reaction catalyzed by chiral phosphoric acid
-
A catalytic enantioselective three-component Ugi reaction was developed. SPINOL-derived phosphoric acid with bulky 2,4,6-tricyclohexylphenyl groups at the 6,6′ positions was found to be the best catalyst to afford α-amino amide derivatives in good to excellent yields (62% to 99%) and enantiocontrol (81% to >99% enantiomeric excess). This asymmetric reaction was applicable well to an array of aliphatic aldehydes. The gram-scale synthesis, modification of dapsone, and enantioselective synthesis of (R)-Lacosamide underline the general utility of this methodology Influence of dihedral angles and substituents of the chiral phosphoric acids on the enantioselectivity was also discussed in this article.
- Zhang, Jian,Wang, Yi-Yan,Sun, He,Li, Shao-Yu,Xiang, Shao-Hua,Tan, Bin
-
-
- Improved Synthesis and Impurity Identification of (R)-Lacosamide
-
An improved synthesis of Lacosamide 1 with high purity has been developed. Critical parameters of each step were identified as well as the impurities generated. Moreover, a creative method to improve chiral purity and stability of the key intermediate (R)-2-amino-N-benzyl-3-methoxypropionamide 10 by forming salt with an achiral acid (phosphoric acid) was discovered to ensure the chiral purity of (R)-Lacosamide. Phosphoric acid was further developed for the deprotection of the Boc group.
- Yang, Anjiang,Hu, Feifei,Li, Zhong,Chen, Mengdi,Cai, Jianguang,Wang, Linghui,Zhang, Tao,Zhao, Chuanmeng,Zhang, Fuli
-
p. 818 - 824
(2019/04/01)
-
- Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts
-
Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.
- Sabatini, Marco T.,Karaluka, Valerija,Lanigan, Rachel M.,Boulton, Lee T.,Badland, Matthew,Sheppard, Tom D.
-
supporting information
p. 7033 - 7043
(2018/05/04)
-
- AN IMPROVED PROCESS FOR THE PREPARATION OF LACOSAMIDE
-
The present invention relates to an improved process for the synthesis of (R)- Lacosamide in which free base of O-methyl-N-benzyl-D-Serinamide is not isolated before acylation. The process avoids the use of column chromatography and chiral resolution for the preparation of different stages of Lacosamide.
- -
-
-
- Industrial preparation method of lacosamide
-
The invention relates to an industrial preparation method of lacosamide. Esterification is performed on D-serine for generating D-serine methyl ester hydrochloride; the D-serine methyl ester hydrochloride reacts with acetyl chloride for generating N-acetyl-D-serine methyl ester; the N-acetyl-D-serine methyl ester reacts with benzylamine for obtaining (R)-2-acetamido-N-benzyl-3-hydroxypropionamide;the (R)-2-acetamido-N-benzyl-3-hydroxypropionamide reacts with methyl p-toluenesulfonate under an alkaline condition for obtaining (R)-2-acetamido-N-benzyl-3-methoxypropionamide. The preparation method provide by the invention has relatively mild reaction conditions in each steps; the raw materials are easy to obtain; no high-toxicity reagent is used; a safe and environment-friendly green chemistry idea is met; and the method is suitable for industrial amplification.
- -
-
Paragraph 0018; 0025; 0026; 0028
(2018/03/26)
-
- High-efficiency racemic lacosamide preparation method
-
The invention discloses a high-efficiency racemic lacosamide preparation method. The preparation method is characterized in that N-acetyl serine shown in a formula (II) is utilized as a raw material and completely reacts with methyl bromide under the action of sodium hydride to obtain 2-acetamido-3-methoxy methyl propionate shown in a formula (III), and then the 2-acetamido-3-methoxy methyl propionate generates ester exchange reaction with benzylamine under the catalyst of trifluoromethanesulfonate to obtain a product namely racemic lacosamide. The suspended lacosamide preparation method disclosed by the invention has an industrial process route which has the advantages of short reaction line, high yield, high atom utilization rate, simpleness in aftertreatment and low cost.
- -
-
Paragraph 0039; 0040; 0041; 0042; 0043; 0044; 0045-0058
(2018/08/04)
-
- A synthesis scheme for preparing method
-
The invention provides a preparation method of lacosamide, which comprises following steps: (A) performing a reaction between D-serine and acetic anhydride to generate an intermediate product N,O-diacetyl-D-serine; (B) performing methylation to the N,O-diacetyl-D-serine to obtain N-acetyl-D-serine methyl ether; (C) carrying out a reaction to the N-acetyl-D-serine methyl ether with benzylamine to obtain (R)-2-acetamido-N-benzyl-3-methoxyl propionamide. The preparation method is short in reaction route, can avoid racemization, and is high in yield and purity of a reaction product.
- -
-
Paragraph 0049; 0055; 0056; 0060; 0061; 0067
(2017/07/19)
-
- A synthesis scheme for synthesizing method (by machine translation)
-
The invention discloses a synthesis scheme for synthesizing method. The synthesis method of epoxy and ethyl methanol as the starting material, passes through methylation, acidic open-loop, with the benzylamine condensation, and azide reduction acylated five step reaction to obtain the raco amide. The method for synthesis of raw materials are simple and easy to obtain, mild reaction conditions, after treatment is simple, the purity of the product is high, the yield is high. (by machine translation)
- -
-
Paragraph 0062-0064
(2017/07/22)
-
- Synthesis of Lacosamide (Vimpat) and Its Derivatives from Aziridine-(2 R)-carboxylate
-
An efficient and scalable synthesis of the antiepileptic drug (R)-lacosamide and its derivatives has been achieved from commercially available aziridine-(2R)-carboxylate in three simple sequential steps, including regioselective aziridine ring opening, debenzylation followed by acetylation in one pot, and amide formation. The advantage of this protocol is that the starting material and reagents are commercially available and a single purification by recrystallization is required after all the chemical transformations, providing the final drug in >99.9% ee.
- Jeong, Hyeonsu,Yadav, Nagendra Nath,Ha, Hyun-Joon
-
p. 1264 - 1272
(2017/03/11)
-
- Process for the preparation of lacosamide or its analogues
-
The present invention provides a stereoselective synthesis method of lacosamide or an analogue thereof used as an anticonvulsant. The synthesis method of the present invention can synthesize lacosamide or an analogue thereof through a short reaction process in a higher yield compared to conventional synthesis methods, by using an aziridine-2-carboxylate derivative. The analogue of lacosamide may be beneficially used to screen for more effective medicinal materials, and further to produce novel pharmacologically active materials.COPYRIGHT KIPO 2017
- -
-
Paragraph 0062-0064
(2018/02/14)
-
- Improved preparation method of modified lacosamide
-
The invention discloses an improved preparation method of modified lacosamide, which is simple to operate, high in chiral purity and low in cost. According to the improved preparation method, in step 1, amidation is carried out on amino by utilizing di-tert butyl dicarbonate (Boc for short), wherein conditions are moderate and the chiral purity is high and at least reaches 90 percent or more; in step 4, high-selectivity dimethyl sulfate is used as a methylation reagent; the cost is low and the conditions are moderate; the methylation yield is high and the improved preparation method is more suitable for large-scale application. The improved preparation method has the most important innovation points that the Boc is used as an N-protection agent and a Boc protecting group can be simply and conveniently removed by adding acid and a hydrogenation removal means does not need to be used. Secondly, the low-price dimethyl sulfate is used for carrying out methylation and the conditions are moderate; the methylation yield is high and the improved preparation method is more suitable for large-scale application.
- -
-
-
- Method for preparing lacosamide by microreactor
-
The invention discloses a method for preparing lacosamide by a microreactor. According to the method, D-serine is used as a starting raw material to take a condensation reaction with aniline for obtaining a compound I; then, methylation reaction is performed with a methylation reagent to obtain a compound II; then, acetylation reaction is performed with an acetylation reagent to obtain the lacosamide; the at least methylation reaction is performed in the microreactor. Compared with a conventional method, the method provided by the invention has the advantages that the protection is not needed on the amidogen of the D-serine; the synthesis route is reduced from the five-step reaction to the three-step reaction; the reaction steps are greatly simplified; meanwhile, the reaction conditions are mild; the safety is high; the environment-friendly effect is good; the byproducts in each step are few; the product yield is high; the method is suitable for industrial production. The formulas are shown as the accompanying drawing.
- -
-
-
- Application of Methyl Bisphosphine-Ligated Palladium Complexes for Low Pressure N-11C-Acetylation of Peptides
-
A mild and effective method is described for 11C-labeling of peptides selectively at the N-terminal nitrogen or at internal lysine positions. The presented method relies on the use of specific biphosphine palladium–methyl complexes and their high reactivity towards amino-carbonylation of amine groups in the presence [11C]carbon monoxide. The protocol facilitates the production of native N-11C-acetylated peptides, without any structural modifications and has been applied to a selection of bioactive peptides.
- Andersen, Thomas L.,Nordeman, Patrik,Christoffersen, Heidi F.,Audrain, Hélène,Antoni, Gunnar,Skrydstrup, Troels
-
supporting information
p. 4549 - 4553
(2017/04/13)
-
- Synthesis of enantiomerically pure 2-(N-aryl, N-alkyl-aminomethyl)aziridines: a new class of ligands for highly enantioselective asymmetric synthesis
-
A simple and effective synthesis of enantiomerically pure 2-(N-aryl-, N-alkyl-aminomethyl)aziridines from (2S)-N-tritylaziridine-2-carboxylic acid methyl ester has been developed. Treating of this key ester with several primary and secondary amines in the presence of AlMe3 provided the corresponding chiral N-trityl-2-carboxamides, and their reduction performed with different reagents resulted in the formation of the expected 2-(aminomethyl)aziridines. The choice of reaction conditions allows to either keep or leave the trityl substituent in the product. Such 2-(aminoalkyl)aziridines have shown very high catalytic efficiency in the asymmetric arylation of aldehydes and in other testing asymmetric reactions. On the other hand, homochiral N-trityl-2-carboxamides are interesting building blocks for the synthesis of various biologically active compounds.
- Jarzyński, Szymon,Le?niak, Stanis?aw,Rachwalski, Micha?
-
p. 1808 - 1816
(2017/11/17)
-
- Direct amidation of unprotected amino acids using B(OCH2CF3)3
-
A commercially available borate ester, B(OCH2CF3)3, can be used to achieve protecting-group free direct amidation of α-amino acids with a range of amines in cyclopentyl methyl ether. The method can be applied to the synthesis of medicinally relevant compounds, and can be scaled up to obtain gram quantities of products.
- Lanigan, Rachel M.,Karaluka, Valerija,Sabatini, Marco T.,Starkov, Pavel,Badland, Matthew,Boulton, Lee,Sheppard, Tom D.
-
supporting information
p. 8846 - 8849
(2016/07/22)
-
- Process for the preparation of(R)-Lacosamide
-
The present invention is directed towards an improved, five step method for the preparation of the anti-epileptic drug (R)-Lacosamide, as illustrated in FIG. 2. The active form of the drug is (R)-enantiomer and the present method gives high yields of (R)-enantiomer of lacosamide. The method does not involve use of any unnatural amino acids as starting material or use of protection/deprotection strategies, strong acids or hydrogenation. Instead, the method uses a cheap and easily available racemic butadiene monoepoxide as the starting material.
- -
-
-
- IMPROVED PROCESS FOR THE PREPARATION OF (R)-LACOSAMIDE
-
The present invention is directed towards an improved, five step method for the preparation of the anti-epileptic drug (R)-Lacosamide, as illustrated in Fig. 2. The active form of the drug is (R)-enantiomer and the present method gives high yields of (R)-enantiomer of lacosamide. The method does not involve use of any unnatural amino acids as starting material or use of protection/deprotection strategies, strong acids or hydrogenation. Instead, the method uses a cheap and easily available racemic butadiene monoepoxide as the starting material.
- -
-
Page/Page column 12; 13
(2016/09/22)
-
- A rakow amide preparation method
-
A preparing process of lacosamide is disclosed. D-serine is adopted as an initial raw material. The method includes: performing amino protection, performing methylation, condensing with benzylamine under a condition of existence of a carboxyl activator, removing an amino protection group, and performing amidation to obtain the lacosamide. The total yield is higher than 66%. The method is high in yield, simple and convenient to operate, high in product purity and especially suitable for industrial production.
- -
-
-
- Method for preparing Lacosamide by one-pot method
-
The invention discloses a method for preparing Lacosamide by a one-pot method. The method comprises the steps: subjecting D-serine and an acetylation reagent to a reaction in a manner of taking dichloromethane as a solvent, and adjusting the pH of a reacted substance to 12-13 by an organic base after the reaction ends; then, controlling the temperature to -5 to 0 DEG C, and adding methyl trifluoromethanesulfonate into the reacted substance for a reaction; and cooling a reacted substance to the temperature of -30 to -25 DEG C, adding a dehydrating agent and benzylamine into the reacted substance for a reaction, carrying out depressurized-concentration drying on material liquid after the reaction ends so as to obtain crude Lacosamide, and then, carrying out recrystallization, thereby obtaining pure Lacosamide. The preparation method is simple and easy in operation, and the prepared Lacosamide has the purity of 99.90% or more and the chiral purity of 99.90%.
- -
-
Paragraph 0038; 0041; 0042
(2016/12/16)
-
- METHOD FOR PREPARING LACOSAMIDE
-
The present invention provides a novel method for preparing lacosamide with high chiral purity from D-serine. The method of the present invention can obtain lacosamide with high chiral purity in a high yield through a simple and environmentally-friendly process and thus can be easily applied to mass production.
- -
-
Paragraph 0034; 0035
(2016/12/01)
-
- A method of synthesizing rakow amide
-
The invention relates to a lacosamide ((R)-2-acetamido-N-benzyl-3-methoxypropionamide) synthesis method. The method adopts D-cystine alkyl ester as a raw material, and the use of a severely toxic chemical raw material dimethyl sulfate and other methylation reagents with potential genotoxicity is avoided in the process, so the method has the advantages of simple operation, environmental protection, and suitableness for industrial large production.
- -
-
-
- IMPROVED PROCESS FOR THE PREPARATION OF LACOSAMIDE AND ITS NOVEL INTERMEDIATE
-
An improved, cost effective process for the preparation of Lacosamide is disclosed. A novel intermediate of formula (IV) and a process for preparation of the novel intermediate is also disclosed. wherein, X is halogen.
- -
-
-
- Process for the preparation of lacosamide
-
A novel process for the preparation of (R)-2-acetamido-N-benzyl-3-methoxypropionamide (Lacosamide) is described. It comprises reacting N-acetyl-D-serine methyl ester with benzylamine catalyzed by a non-nucleophilic base to obtain (R)-2-acetamido-2-N-benzyl-3-hydroxy propionamide followed by its methylation.
- -
-
Page/Page column 14
(2016/10/17)
-
- 3-Azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate), a new reagent for the synthesis of the N-protected amino acid-ASUD ester
-
A new reagent, 3-azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate) is described for the synthesis of N-protected amino acid-ASUD esters which are active esters useful in the synthesis of peptides. This compound was synthesized by reacting N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) with diphenyl chlorophosphate in the presence of a base at room temperature and was obtained in high yields. The ASUD-diphenyl phosphate reagent reacts with N-protected amino acids under mild conditions to give the corresponding ASUD active esters, while preserving the enantiomeric purity of the amino acid. The new reagent is a stable crystalline compound and eliminates the need for DCC, a potent skin allergen, used previously for the synthesis of N-protected amino acid-ASUD ester.
- Rao, B. Leelamaheswara,Nowshuddin, Shaik,Jha, Anjali,Divi, Murali K.,Rao
-
p. 487 - 491
(2016/06/06)
-
- Chiral pool approach for the synthesis of functionalized amino acids: Synthesis of antiepileptic drug (R)-lacosamide
-
An efficient total synthesis of (R)-lacosamide 1 has been achieved from N-Boc-N,O-isopropylidene-l-serinol 2 which could easily be obtained from natural l-serine. Our synthesis of 1 starting from 2 using chiral pool strategy resulted in 54% overall yield.
- Aratikatla, Eswar K.,Bhattacharya, Asish K.
-
supporting information
p. 5802 - 5803
(2015/10/05)
-
- A Method for preparing Lacosamide
-
In the present invention, provided is a novel method of manufacturing lacosamide with high purity of chiral from D-serine, which is allowed to obtain lacosamide with high purity of chiral in high yield through a simple, eco-friendly process and is accordingly used in mass-production.COPYRIGHT KIPO 2015
- -
-
Paragraph 0030; 0042-0044
(2016/12/07)
-
- Development of Scalable Conditions for the Ugi Reaction-Application to the Synthesis of (R)-Lacosamide
-
The Ugi reaction is applied for the preparation of (R)-lacosamide, an important drug for the treatment of epilepsy. To this end, key issues associated with the Ugi reaction, such as a practical preparation of the foul-smelling isocyanide as well as the efficient introduction of chirality via a cheap and easily removable chiral directing group, were solved. Enantiomerically pure (>99.9% ee) drug substance meeting all required purity specifications is prepared in operationally simple four steps in 40% overall yield from the commodity chemical benzylamine.
- Wehlan, Hermut,Oehme, Jan,Sch?fer, Alexander,Rossen, Kai
-
p. 1980 - 1986
(2016/01/09)
-
- An enantioselective approach to functionalized amino acids: Total synthesis of antiepileptic drug (R)-lacosamide
-
A short and highly efficient synthetic approach to enantiopure functionalized amino acids (FAAs) 1 skeleton from racemic butadiene monoepoxide as a starting material and its application to the total synthesis of an antiepileptic drug (R)-lacosamide 2 are described. The synthesis utilizes the palladium catalyzed Trosts Dynamic Kinetic Asymmetric Transformation (DYKAT) as key step.
- Garg, Yuvraj,Pandey, Satyendra Kumar
-
supporting information
p. 4201 - 4203
(2015/05/05)
-
- Total synthesis of lacosamide
-
Total synthesis of anticonvulsant amino acid, lacosamide, is reported. The key step is stereospecific allyl cyanate-to-isocyanate rearrangement, which proceeds with chirality transfer. The enantiopure starting material for the rearrangement step was accessed from ethyl l-lactate.
- Stecko, Sebastian
-
p. 6342 - 6346
(2014/07/21)
-
- NOVEL PROCESS FOR THE PREPARATION OF (R)-N-BENZYL-2-ACETAMIDO-3-METHOXYPROPIONAMIDE
-
The invention is a novel process for the preparation of lacosamide by employing novel intermediates of formula III and IV:
- -
-
Paragraph 0049
(2014/11/11)
-
- 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 SYNTHESIS OF ANTIEPILEPTIC DRUG LACOSAMIDE
-
The present invention relates to the improved and efficient process for the synthesis of antiepileptic drug Lacosamide in high enantiopurity (>98% ee) and better yield. More particularly, the present invention relates to improved and efficient, cost effective process for synthesis of desired (R) isomer of Lacosamide starting from commercially available (S)-benzyl glycidyl ether.
- -
-
-
- PROCESS FOR THE PREPARATION OF LACOSAMIDE USING NOVEL INTERMEDIATES
-
The present invention provides an improved and commercial process for the preparation of Lacosamide having formula (I). Further, the present invention also provides the novel intermediate compounds of formula (VI) and (VII) and their process for the preparation. Present process utilizes compound of formula (VI) and (VI)I as key novel intermediates for the preparation of Lacosamide.
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Page/Page column 16
(2014/10/15)
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- PROCESS FOR THE PREPARATION OF LACOSAMIDE
-
The present invention relates to a novel and improved process for the preparation of lacosamide, wherein the process is a sequential one-pot process.
- -
-
-
- PROCESS FOR THE PREPARATION OF LACOSAMIDE
-
The present invention relates to an improved process for the preparation of Lacosamide of Formula (I), comprising: O-methylating a compound of Formula (V) or a compound of Formula (XX) or a compound of Formula XXII; in the presence of a methylating agent and a base to produce Lacosamide of Formula (I).
- -
-
-
- PROCESS FOR THE PREPARATION OF LACOSAMIDE
-
Present invention relates to an improved and commercial process for the preparation of lacosamide ((R)-2-acetami-do-N-benzyl-3-methoxypropanamide) of formula (I). Present process utilizes high purity crystalline solids of formulae (XXXII) and (XIII) as key intermediates. Lacosamide is indicated for the adjunctive treatment of partial onset seizures in patients aged at least 17 years.
- -
-
Paragraph 0034
(2013/03/26)
-
- PROCESS FOR THE PREPARATION OF AMINO ACID DERIVATIVES
-
The present invention relates to a process of manufacture of compounds of formula (B) wherein R1, R2 and R3 are as defined for compounds of formula (A), which process comprises hydrogenation of compounds of general formula (A). In particular, the present invention relates to an improved process for the manufacture of Lacosamide (LCM), (R)-2-acetamido-N-benzyl-3-methoxypropion-amide (B1), which is useful as an anticonvulsive drug.
- -
-
Paragraph 0164; 0165; 0166
(2013/07/31)
-
- A non-infringing route for enantioselective synthesis of antiepileptic agent lacosamide
-
A non-infringing route for enantioselective synthesis of lacosamide has been developed. The synthesis started from commercially available acrylic acid and was completed in eight steps using Sharpless asymmetric dihydroxylation as a key step with an overal
- Wadavrao, Sachin B.,Narikimalli, Ashritha,Narsaiah, A. Venkat
-
p. 3383 - 3386
(2014/01/06)
-
- PROCESS FOR THE PRODUCTION OF N-SUBSTITUTED 2-(ACETYLAMINO)-N'-BENZYL-3-METHOXYPROPANAMIDES
-
A process for the production of N-substituted 2-(acetylamino)-N'-benzyl-3-methoxypropanamides and subsequent treatment with acids is described. This process can be used for the production of (R)-Lacosamide.
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Page/Page column 32
(2013/06/05)
-
- PROCESSES FOR THE PREPARATION OF (R)-2-ACETAMIDO-N-BENZYL-3-METHOXYPROPIONAMIDE AND INTERMEDIATES THEREOF
-
This invention relates to processes for the preparation of (R)-2- acetamido-/V-benzyl-3-methoxypropionamide (I) and intermediates thereof. Formula (I).
- -
-
-
- LACOSAMIDE INTERMEDIATE COMPOUND, PREPARATION METHOD THEREOF AND USE THEREOF
-
A new compound is provided, which is used for preparing lacosamide. A novel method for preparing lacosamide is also provided. During the reaction, iodomethane and silver oxide that are cost expensive are not used, nor a Pd-c catalyst is used, so the production cost is low, the raw materials and accessory materials are cheap and easily available, and the process is simple, so that industrial production is easy to realize; and moreover, the yield is high, and good economic efficiency can be achieved.
- -
-
-
- 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
- -
-
-
- AN IMPROVED PROCESS FOR THE PREPARATION OF LACOSAMIDE
-
The present invention relates to an improved process for the preparation of Lacosamide having formula (I).
- -
-
-
- PROCESS FOR PREPARING LACOSAMIDE
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The present invention provides a process for the preparation of lacosamide in substantially optically pure form, which in one aspect comprises the following steps: (i) resolution of O-methyl-D,L-serine to provide O-methyl-D-serine in substantially optically pure form; (ii) acetylation of O-methyl-D-serine thereby obtained to provide the N-acetyl 10 derivative thereof in substantially optically pure form; (iii) activating the carboxy group of the compound thereby obtained; and (iv) reacting the compound thereby obtained with benzylamine.
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Page/Page column 26
(2012/06/01)
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- N-OPTIONALLY SUBSTITUTED ARYL-2-OLIGOMER-3-ALKOXYPROPIONAMIDES
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The invention relates to (among other things) N-optionally substituted aryl- 2-oligomer-3-alkoxypropionamides and compositions comprising the same. A compound of the invention, when administered by any of a number of administration routes, exhibits one or more advantages over corresponding compounds lacking the oligomer.
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