Process for producing n-acyl-2,3-dehydro-amino carboxylic...

C - Chemistry – Metallurgy – 07 – C

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C07C 233/00 (2006.01) C07D 213/81 (2006.01) C07D 307/68 (2006.01) C07D 333/24 (2006.01) C07D 333/28 (2006.01) C07D 333/38 (2006.01)

Patent

CA 1277988

ABSTRACT OF THE DISCLOSURE N-acyl-2,3-dehydro-amino carboxylic esters having the general formula (I), Image wherein R1 represents a straight-chain or branched (C1-C4) alkyl radical, a phenyl radical or a benzyl radical, R2 re- presents hydrogen or a methyl radical, R3 represents hydro- gen, a straight-chain or branched (C1-C16)alkyl radical, a (C3-C8)cycloalkyl radical, a (C1-C6)alkyl mercapto radical, a phenyl mercapto radical or a methoxy-carbonyl-methyl mercapto radical and R4 represents a straight-chain or branched (C1- C16)alkyl radical or (C2-C16)alkenyl radical, either unsub- stituted or mono- or poly-substituted by halogen, a methoxy group or by an acetylthio group, an unsubstituted (C3-C8) cycloalkyl radical which may be mono- or poly-substituted by halogen or a methyl group, an unsubstituted phenyl radical which may be mono- or poly-substituted by halogen, a nitro group, a (C1-C4)alkyl or alkoxy group or by a trifluoromethyl group, an unsubstituted cinnamyl radical, which may be mono- or poly- substituted heteroaryl radical which may be mono or poly- substituted by halogen, a (C1-C4)alkyl or alkoxy group or by a trifluoromethyl group, an aryl or heteroaryl methyl radical, an unsubstituted phenoxy methyl radical or phenyl-ethyl radical which may be mono- or poly-substituted by halogen, a nitro group, a (C1-C4)alkyl group or by a trifluoromethyl group, or a 2-(2,2,2-dichloro-ethenyl)-3,3-dimethyl cyclopropyl radical are produced by reacting a 2-azido-carboxylic ester having the general formula Image (II) at a temperature of between 0 and 150°C in the presence of a perrhenate with a carboxylic acid halide having the general formula Image (III) The compounds having the general formula (I) are inhibitors for the dipeptidase [E.C.3.4.13.11].

503677

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