PROCESS FOR PRODUCING UNSATURATED AMINO ACID COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAME AS ACTIVE INGREDIENT

• Main Authors: HECKENDORN,ROLAND,CH, ALLGEIER,HANS,DE, BOLD,GUIDO,CH, TOGNI,ANTONIO,CH, ANGST,CHRISTOF,US, DUTHALER,RUDOLF,CH
• Format: Patent
• Language: English
• Published: 28.02.1991
• 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

Unsaturated amino acid compounds of the formula in which R1 denotes hydrogen, alkyl or hydroxyl, R2 denotes hydrogen, alkyl, halo(lower alkyl), hydroxy(lower alkyl), (lower alkoxy)(lower alkyl), aryl(lower alkyl), lower alkenyl, halogen or aryl, R3 denotes hydrogen, alkyl or aryl, R4 denotes hydrogen or alkyl, R5 represents carboxyl which may be esterified or amidated, R6 represents an amino group which is unsubstituted or substituted by lower alkyl or aryl(lower alkyl), A is alpha , omega -alkylene having 1 to 3 carbon atoms which is unsubstituted or substituted by alkyl or represents a direct bond and B denotes methylene or a bond, with the proviso that A represents alpha , omega -alkylene having 1 to 3 carbon atoms which is unsubstituted or substituted by alkyl if B represents a direct bond, and salts thereof are prepared by releasing in a compound of the formula in which Z1 denotes protected or unprotected hydroxyl, Z2 denotes a group R1 or protected hydroxyl, Z5 denotes a group R5 or protected carboxyl, Z6 represents a protected group R6 and R1, R2, R3, R4, R5, R6, A and B have the abovementioned meanings, the protected group Z6 and, if desired, Z1, Z2 and/or Z5 by treatment with a tri(lower alkyl)halo- silane and, if desired, converting the compound obtained into another compound of the formula I, resolving a mixture obtained of optical isomers into the components and separating off the desired isomer and/or converting a free compound obtained into a salt or a salt obtained into the free compound or into another salt. (2R)-E-Ethyl 2-amino-4-methyl-5-phosphono-3-pentenoate and salts thereof are also described.