4-substituted 2-aminoalk-3-enoic acids

Details 4-substituted 2-aminoalk-3-enoic acids 4-substituted 2-aminoalk-3-enoic acids

C - Chemistry, Metallurgy

07

F

167/179, 260/291

C07F 9/38 (2006.01) A61K 31/66 (2006.01) C07F 9/59 (2006.01)

Patent

CA 2026038

CA- 4-17759/+ 4-Substituted 2-aminoalk-3-enoic acids Abstract Substituted 2-aminoalk-3-enoic acid derivatives of formula I Image (I), wherein R1 is an aliphatic hydrocarbon radical that is substituted by optionally acylated or aliphatically or araliphatically etherified hydroxy, by halogen, by optionally acylated and/or aliphatically substituted amino or by an aza-, diaza-, azoxa- or oxa-cycloaliphatic radical, or is an oxacycloaliphatic hydrocarbon radical bonded via a carbon atom, or is an optionally aliphatically N-substituted or N-acylated azacycloaliphatic hydrocarbon radical, and R2 is free or esterified carboxy, and their salts have a pronounced and selective antagonistic activity towards N-methyl-D-aspartic acid-sensitive (NMDA-sensitive) excitatory amino acid receptors. They are prepared, for example, as follows: in a compound of formula II Image (II), wherein Z1, Z2 are optionally protected hydroxy, Z3 is an aliphatic hydrocarbon radical that is substituted by optionally protected or acylated or aliphatically or araliphatically etherified hydroxy, by halogen, by optionally protected or acylated and/or aliphatically substituted amino or by an aza-, diaza-, azoxa- or oxa-cycloaliphatic radical, or is an oxacycloaliphatic hydrocarbon radical bonded via a carbon atom, or is an optionally protected or aliphatically N-substituted or N-acylated azacycloaliphatic hydrocarbon radical, and Z4 is protected amino, protected amino Z4 and, if present, protected amino as a constituent of Z3 is converted into amino and, if present, protected hydroxy Z1, Z2 and/or protected hydroxy as a constituent of Z3 is converted into hydroxy and, if present, a protected azacycloaliphatic hydrocarbon radical Z3 is freed and, if desired, a resulting compound is converted into a different compound of formula I, an isomeric mixture obtainable in accordance with the process is separated into its components and the preferred isomer is separated, and/or a free compound obtainable in accordance with the process is converted into a salt or a salt obtainable in accordance with the process is converted into the corresponding free compound.

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