Intermediates and process for producing fluorine-containing...

Details Intermediates and process for producing fluorine-containing... Intermediates and process for producing fluorine-containing...

C - Chemistry, Metallurgy

07

C

C07C 62/38 (2006.01) A61P 25/16 (2006.01) A61P 25/18 (2006.01) A61P 25/22 (2006.01) A61P 25/24 (2006.01) A61P 25/28 (2006.01) C07C 51/363 (2006.01) C07C 227/18 (2006.01) C07C 229/50 (2006.01) A61K 31/196 (2006.01) C07D 235/02 (2006.01) C07D 303/38 (2006.01)

Patent

CA 2354619

The present inventions relate to a (1S,5R,6S)- or (1SR,5RS,6SR)-3-fluoro-2-oxobicyclo[3.1.0]hex-3-ene-6--carboxylic acid derivative represented by Formula (1): (see formula 1) [in the formula, R represents OR1 or NR1R2, wherein R1 and R2 are identical or different, and each represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a(C3-C6 cycloalkyl) (C1-C6 alkyl) group, an aryl group, an aryl (C1-C6 alkyl) group, a (C1-C6 alkoxy) (C1-C6 alkyl) group, a C1-C6 hydroxyalkyl group, a (C1-C6 alkylthio) (C1-C6 alkyl) group, or a C1-C6 mercaptoalkyl group], and a process for producing the same, and a process for efficiently producing a fluorine-containing amino acid compound acting on group 2 metabotropic glutamate receptors, which has treatment effects or prevention effects on psychiatric diseases or neurological diseases, characterized by hydrogenating the derivative, and subsequently, subjecting it to hydantoination or aminocyanidation, followed by hydrolysis.

Cette invention a trait à des dérivés d'acide (1S, 5R, 6S)- ou (1SR, 5RS, 6SR)-3-fluoro-2-oxobicyclo[3.1.0]-hex-3-ène-6-carboxylique représentés par la formule générale (1). Elle concerne également un procédé de production de ces dérivés ainsi qu'un procédé de production à rendement élevé d'un composé aminoacide contenant du fluor, agissant sur le récepteur de glutamate métabotropique du groupe 2, qui a une action thérapeutique et prophylactique sur des maladies psychiatriques ou neurologiques. Ce procédé se caractérise par l'hydrogénation du composé susmentionné (1) ainsi que par la conversion de ce composé en hydantoïne ou en amino-cyanure suivie d'une hydrolyse. Dans cette formule (1), R représente OR<1> ou NR<1>R<2> (R<1> et R<2> étant identiques ou différents et représentant, chacun, un hydrogène, un alkyle portant de 1 à 6 atomes de carbone, un cycloalkyle portant de 3 à 6 atomes de carbone, un (C3-6 cycloalkyle)(C1-6 alkyle), un aryle, un aryle (C1-6 alkyle), un (C1-6 alcoxy)(C1-6 alkyle), un hydroxyalkyle portant de 1 à 6 atomes de carbone, un (C1-6 alkylthio)(C1-6 alkyle), ou un mercaptoalkyle portant de 1 à 6 atomes de carbone).

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