N-chloro-N-sodium carbamates are more nucleophilic than neutral amides and hence it was proposed that they can facilitate the ring opening of aziridine derivativesThe synthesis of the title compounds was carried out by a reaction of N-(nosyl)aziridines with N-chlorocarbamate 1,1-dimethylethyl ester sodium salt, whereby the nosyl group may be easily removed for further transformation.This method was applied to the transformation of D-aspartic acid into (2R)-2-amino-3-carboxy-N,N,N-trimethyl-1-propanaminium inner salt (emeriamine).The synthesis of the target compound was achieved by a ring opening of an aziridine derivative (I) with tert-Bu chlorocarbamate sodium salt and the product thus formed was a chiral diamine derivative (II).II was transformed into the target compound emeriamine [i.e., (2R)-2-amino-3-carboxy-N,N,N-trimethyl-1-propanaminium inner salt] (III).

03 May 2010·ChemMedChemQ3 · MEDICINE

Aminocarnitine Ureidic Derivatives as Inhibitors of Carnitine Palmitoyltransferase I

Q3 · MEDICINE

Article

Author: Emanuela Tassoni ; Roberto Conti ; Walter Cabri ; Silvia Vincenti ; Lucilla Mastrofrancesco ; Grazia Gallo ; Paolo Carminati ; Rita Ricciolini ; Natalina Dell'Uomo ; Fabio Giannessi

Studies are presented on CPT-1 inhibitors with a series of new aminocarnitine ureidic derivatives, exploring the effects of aromatic functionalities in the straight-chain alkyl group of Teglicar.Compound 3 (I) was selected as a promising candidate for further investigations as an antidiabetic and/or antiketotic agent.

01 Dec 2003·European Journal of Organic Chemistry

A Practical and Stereoconservative Synthesis of (R)‐3‐Amino‐4‐(trimethylammonio)butanoate [(R)‐Aminocarnitine], and Its Trimethylphosphonium and Simple Ammonium Analogues Starting from D‐Aspartic Acid

Author: Calvisi, Giuseppina ; Tinti, Maria Ornella ; De Angelis, Francesco ; Dell'Uomo, Natalina ; Giannessi, Fabio ; Dejas, Roberto

AbstractWe have developed a new stereospecific synthesis of (R)‐aminocarnitine using D‐aspartic acid as the starting material. This strategy, which is simple and amenable to an industrial scale‐up, gives the target compound in six steps and in fairly good overall yields (41%). Other aminocarnitine related molecules such as optically pure (R)‐3‐amino‐4‐(trimethylphosphonio)butanoic acid and (R)‐3,4‐diaminobutanoic acid dihydrochloride have also been prepared according to the same synthetic strategy. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Indication	Highest Phase	Country/Location	Organization	Date
Diabetes Mellitus	Preclinical	Japan	Takeda Pharmaceutical Co., Ltd.	-

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