Nitric oxide releasing amino acid ester compound, composition and method of use
A technology of nitric oxide and compounds, applied in the fields of treating cardiovascular diseases, therapeutic reagents, and novel group preparations, can solve problems such as limited effect and side effects
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[0163] Disclosed in the embodiment are (a) treating cardiovascular disease; (b) treating renal vascular disease; (c) treating diabetes; (d) treating diseases caused by oxidative stress; (e) treating endothelial dysfunction; (g) treatment of liver cirrhosis; (h) treatment of preeclampsia; (j) treatment of osteoporosis; (k) treatment of renal disease; (l) reperfusion of injured ischemia; And / or (m) a method of preserving tissue, organ, organ part and / or limb comprising administering to a patient a therapeutically effective amount of an amino acid ester compound, optionally replaced with at least one nitric oxide releasing group. The amino acid ester compound is preferably connected with one or more nitric oxide releasing groups, and it is provided in the form of a pharmaceutical composition further comprising a pharmaceutically acceptable carrier or diluent. The novel compound and novel composition of the present invention are described in detail as follows:
[0164] In the emb...
Embodiment 1
[0295] step 1
[0296]
[0297] Mononitration of existing alcohols can often be achieved by concentrated nitric acid. Thus 2-hydroxyethyl nitrate (nitroxyethanol), a known compound, can be prepared by the reaction of concentrated nitric acid and 1,2-ethylene glycol. The reaction was carefully monitored and the product was purified, washed, dried and used directly in the following reactions.
[0298] step 2
[0299]
[0300] Esters can be formed via different reactants such as DCC and EDC which are often used. Different conditions can be used, one specific example of which is listed below.
[0301] After the addition of dichloromethane (25 liters), 8 kg of 2-hydroxyethyl nitrate were then added to the reactor. Next, tert-butoxycarbonyl L-valine (12.5 kg) was slowly added with stirring, and the reaction mixture was cooled to -10°C. Next, DMAP (50 g) was added as a catalyst, and DCC (12.5 kg dissolved in 5 L of dichloromethane) was slowly added dropwise at -10°C. The ...
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