Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1998-07-31
1999-11-23
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
560129, C07D22332, C07C 6900
Patent
active
059903074
ABSTRACT:
This invention relates to a process for the preparation of the formula I compound [2-((8,9)-dioxo-2,6-diazabicyclo[5.2.0]-non-1(7)-en-2-yl)ethyl]phosphonic acid, a NMDA antagonist useful as an anticonvulsant and neuroprotectant in situations involving excess release of excitatory amino acids. ##STR1## In the process of the present invention, 3-aminopropyl carbamic acid 1,1-dimethylethyl ester is reacted with a dialkyl vinylphosphonate to obtain N-[3-(t-butyloxycarbonyl-amino)propyl]-2-aminoethylphosphonic acid dialkyl ester (d) in 80% yield. Reaction of (d) with a 3,4-dialkoxycyclobut-3-en-1,2-dione gives [3-[[2-(dialkoxyphosphoryl)ethyl]-(2-alkoxy-3,4-dioxo-1,2-cyclobuten-1-yl) amino]propyl] carbamic acid 1,1-dimethylethyl ester (e) in 96% yield. Deprotection and cyclization of (e) in trifluoroacetic acid gives [2-((8,9)-dioxo-2,6-diazabicyclo[5.2.0]-non-1(7)-en-2-yl)ethyl]phosphonic acid dialkyl ester (c) in 58% yield. The phosphonic acid diethyl ester (c) was treated with bromotrimethylsilane to give compound I.
REFERENCES:
patent: 5168103 (1992-12-01), Kinney et al.
Asselin Andre A.
Kinney William A.
Schmid Jean
American Home Products Corporation
Eck Steven R.
Kifle Bruck
Seifert Arthur G.
Shah Mukund J.
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