METHOD OF SYNTHESIS OF [2-((8,9)-DIOXO-2,6-DIAZOBI-CYCLO-[5,2,0]NON-1(7)-EN-2-YL)ETHYL]PHOSPHONIC ACID, METHOD OF SYNTHESIS OF N-[3-(TERTIARY BUTYLOXY- CARBONYLAMINO)PROPYL]-2-AMINOETHYLPHOSPHONIC ACID DI-C-C-ALKYL ESTER, COMPOUNDS Russian patent published in 2003 - IPC

Abstract RU 2205834 C2

FIELD: organic chemistry, chemical technology, medicine. SUBSTANCE: invention relates to method of synthesis of [2-((8,9)-dioxo-2,6-diazobicyclo-[5.2.0] non-1(7)-en-2-yl)ethyl] phosphonic acid. According to method of invention 3-aminopropylcarbamic acid 1,1-dimethylethyl ester interacts with dialkylvinyl phosphonate to form N-[3-tert.-butyloxycarbonyl- amino)propyl]-2-aminoethylphosphonic acid dialkyl ester (d) with the yield 80%. Reaction of (d) with 3,4-dialkoxycyclobut-3-en-1,2-dione results to [3-[[2-(dialkyloxyphosphoryl)ethyl] -(2-alkoxy-3,4-dioxo-1,2-cyclobutene-1-yl)amino] propyl] carbamic acid 1,1-dimethyl ester (e) with the yield 96%. Removal of protection and cyclization of (e) in trifluoroacetic acid results to [2-((8,9)-dioxo-2,6-diazabicyclo[5.2.0] - non-1(7)-en-2-yl)ethyl]phosphonic acid dialkyl ester (c) with the yield 58%. Phosphonic acid diethyl ester (c) is treated with trimethylbromo- silane to form the compound (I). Compound of the formula (I) is an antagonist of NMDA-receptors and used as an anticonvulsant and neuroprotective agent in excessive secretion of excitative amino acids. EFFECT: improved method of synthesis, valuable medicinal properties of compound. 14 cl

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RU 2 205 834 C2

Authors

Asselin Andre Al'Fred

Kinni Uill'Jam Ehlvin

Shmid Dzhin

Dates

2003-06-10Published

1998-07-31Filed