PROCESS FOR PRODUCING 4-SUBSTITUTED 2-AMINO-3-ALKENECARBOXYLIC ACIDS

• Main Authors: HECKENDORN,ROLAND,CH, ANGST,CHRISTOF,CH, WALLACH,DANIEL,CH, ALLGEIER,HANS,DE
• Format: Patent
• Language: English
• Published: 29.07.1991
• Edition: 5
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMISTRY; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS

Substituted 2-aminoalk-3-enoic acid derivatives of the formula I process for the preparation of unsaturated amino carboxylic acid derivatives of the formula I in which R1 is an aliphatic or via a C atom bonded oxacycloaliphatic or optionally aliphatically N-substituted or N-acylated azacycloaliphatic hydrocarbon radical which is substituted by optionally acylated or aliphatically or araliphatically etherified hydroxyl, by halogen, by optionally acylated and/or aliphatically substituted amino or by an aza-, diaza-, azoxa- or oxacycloaliphatic radical, and R2 is free or esterified carboxyl, and their salts have a pronounced and selective antagonistic action on N-methyl-D-aspartic acid-sensitive (NMDA-sensitive) excitatory amino-acid receptors. They are prepared, for example, by, in a compound of the formula II in which Z1, Z2 are optionally protected hydroxyl, Z3 is an aliphatic or via a C atom bonded oxacycloaliphatic or optionally protected or aliphatically N-substituted or N-acylated azacycloaliphatic hydrocarbon radical which is substituted by optionally protected or acylated or aliphatically or araliphatically etherified hydroxyl, by halogen, by optionally protected or acylated and/or aliphatically substituted amino or by an aza-, diaza-, azoxa- or oxacycloaliphatic radical, and Z4 is protected amino, converting protected amino Z4 and, where present, as component of Z3 into amino and, where present, protected hydroxyl Z1, Z2 and/or as component of Z3 into hydroxyl, and, where present, liberating a protected azacycloaliphatic hydrocarbon radical Z3 and, if required, converting a resulting compound into another compound of the formula I, fractionating a mixture of isomers obtainable according to the process into the components, and separating off the isomer which is preferred in each case, and/or converting a free compound obtainable according to the process into a salt or a salt obtainable according to the process into the corresponding free compound.