- Preparation method of lacosamide
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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.
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Paragraph 0031-0032
(2020/07/02)
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- Improved Synthesis and Impurity Identification of (R)-Lacosamide
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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
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p. 818 - 824
(2019/04/01)
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- Preparation method for lacosamide
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The invention provides a preparation method for lacosamide. According to the invention, easily available Boc-serine (a compound I) is used as a starting material for preparation of lacosamide, and the quality of prepared lacosamide is identical to the quality of an original drug. The preparation method provided by the invention uses easily available raw materials, does not need expensive iodomethane or severely toxic dimethyl sulfate, and is high in product purity and yield and low in toxicity and pollution, and requirements of reaction conditions on equipment are not high; thus, the method is suitable for industrial production.
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Paragraph 0036; 0037
(2017/07/21)
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- A rakow amide preparation method
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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.
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Paragraph 0140; 0141
(2016/10/17)
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- Chiral pool approach for the synthesis of functionalized amino acids: Synthesis of antiepileptic drug (R)-lacosamide
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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.
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supporting information
p. 5802 - 5803
(2015/10/05)
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- PROCESS FOR THE SYNTHESIS OF ANTIEPILEPTIC DRUG LACOSAMIDE
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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.
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Paragraph 0072; 0073
(2014/02/15)
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- PROCESS FOR THE PREPARATION OF LACOSAMIDE USING NOVEL INTERMEDIATES
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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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- PROCESS FOR THE PREPARATION OF LACOSAMIDE
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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.
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Paragraph 0031
(2013/03/26)
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- NOVEL POLYMORPH OF LACOSAMIDE
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The present invention provides novel crystalline form of lacosamide, process for its preparation and pharmaceutical compositions comprising it. The present invention also provides a process for the preparation of lacosamide amorphous form.
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Page/Page column 8
(2012/04/23)
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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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Page/Page column 36-37
(2012/05/04)
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- First asymmetric synthesis of the antiepileptic drug Lacosamide (Vimpat) based on a hydrolytic kinetic resolution strategy
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An efficient asymmetric synthesis of the new antiepileptic drug, Lacosamide is described in high enantiopurity (>98% ee), using Jacobsen's hydrolytic kinetic resolution strategy as a key step.
- Muthukrishnan,Mujahid,Sasikumar,Mujumdar
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experimental part
p. 1353 - 1357
(2011/11/29)
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- PROCESS FOR PREPARING (R)-2-ACETAMIDO-N-BENZYL-3-METHOXY-PROPIONAMIDE
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Processes for preparing and purifying (R)-2-acetamido-N-benzyl-3-methoxy- propionamide of formula-1 and intermediates thereof are provided.
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- A PROCESS FOR THE PREPARATION OF LACOSAMIDE
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Present invention relates to an improved and commercial process for the preparation of lacosamide ((R)-2-acetamido-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.
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Page/Page column 10-11
(2011/09/14)
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- Preparation and biological evaluation of key fragments and open analogs of scleritodermin A
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The synthesis of key fragments of scleritodermin A, their assembly, and their biological evaluation as cytotoxic and anthelmintic were performed.Highlights of the synthetic route include formation of the a-ketoamide linkage and use of stereocontrolled reactions.Open analogs of this natural product were obtained using a convergent strategy.
- Sellanes, Diver,Campot, Francisco,Nú?ez, Ivana,Lin, Gerardo,Espósito, Pablo,Dematteis, Sylvia,Salda?a, Jenny,Domílnguez, Laura,Manta, Eduardo,Serra, Gloria
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scheme or table
p. 5384 - 5395
(2010/08/19)
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- IMPROVED SYNTHESIS SCHEME FOR LACOSAMIDE
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The present invention is concerned with an improved method of producing (R)-2-acetamido-N-benzyl-3-methoxypropionamide (lacosamide) comprising the 0-methylation of a compound of formula (I) to produce a compound of formula (I I) in a single step reaction.
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Page/Page column 17
(2010/10/20)
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- SUBSTITUTED THIOPHEN-CARBOXYLIC ACID AMIDES, THE PRODUCTION AND THE USE THEREOF IN THE FORM OF A DRUG
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The invention relates to novel substituted thiophen-2-carboxylic acid amides of general formula (I), wherein A and R1 to R8 are defined as specified in the claim 1, the tautomers, enantiomers, diastereomers, mixtures and salts thereof, in particular the salts thereof which are physiologically compatible with inorganic or organic acids or bases and exhibit interesting properties.
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Page/Page column 132-133
(2010/02/14)
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- NOVEL SUBSTITUTED THIOPHENECARBOXAMIDES, THEIR PRODUCTION AND THEIR USE AS MEDICAMENTS
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The invention relates to novel substituted thiophene-2-carboxamides of general formula (I), in which A, and R1 to R8c are defined as cited in claim 1. The invention also relates to the tautomers, enantiomers, diastereomers, mixtures and salts, in particular the physiologically compatible salts of said compounds containing inorganic or organic acids or bases, which exhibit valuable properties.
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Page/Page column 168-169
(2008/06/13)
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- QUINAZOLINE DERIVATIVES
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A quinazoline derivative of the formula (I) wherein: R1, R2, R3, R3a, R4, R5, R5a R6, R7, a, m and p are as defined in the description. Also claimed are pharmaceutical compositions containing the quinazoline derivative, the use of the quinazoline derivatives as medicaments and processes for the preparation of the quinazoline derivative. The quinazoline derivatives of formula (I), are useful in the treatment of hyperproliferative disorders such as a cancer.
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Page/Page column 127
(2008/06/13)
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- Chlorothiophenecarboxamides as P1 surrogates of inhibitors of blood coagulation factor Xa
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Neutral chlorothiophenecarboxamides bearing an amino acid and a substituted aniline were synthesized and investigated for their factor Xa inhibitory activity in vitro. From selected 2-methylphenyl morpholinones the solution properties were determined. The most soluble and active compounds were then investigated in different animal species to compare the pharmacokinetic parameters. This led to a potent, water soluble and orally bioavailable candidate for further development: EMD 495235.
- Mederski, Werner W.K.R.,Cezanne, Bertram,Amsterdam, Christoph Van,Bühring, Karl-Ulrich,Dorsch, Dieter,Gleitz, Johannes,M?rz, Joachim,Tsaklakidis, Christos
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p. 5817 - 5822
(2007/10/03)
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