15-deoxyspergualin analogs, their method of preparation and their use in therapeutics
A technology of analogs and compounds, applied in the field of novel compounds, can solve the problem of 15-deoxysperguline not having chemical stability
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Embodiment 1
[0166] Tris(trifluoroacetic acid)N-[4-[[3-(amino)butyl]amino]butyl]-N′-[6-[(aminoiminomethyl)amino]hexyl]malonamide
[0167] 7.8g (10.8 10 -3 mol) The product obtained in preparation 9 was dissolved in 40 ml of dichloromethane, and 40 ml of trifluoroacetic acid was added. The reaction mixture was stirred at room temperature for 5 hours and then concentrated under reduced pressure. Using water / acetonitrile / trifluoroacetic acid mixture (8 / 1 / 1 v / v) as eluent, the remaining oil was purified by medium pressure chromatography on RP18 grafted silica (particle size: 5-20 microns). The resulting pure fractions were combined and lyophilized. The lyophilized product was dissolved in 100 ml of water, the solution was washed twice with 100 ml of ethyl acetate each time, and then the aqueous phase was lyophilized again. This operation was repeated twice to remove trifluoroacetic acid. Obtained 4.5 g (yield=57%) of the desired product as an amorphous solid.
[0168] 1 H NMR(DMSO-d 6 ): 1.15-1.20...
Embodiment 2
[0187] Tris(trifluoroacetic acid) 2-[[[4-[[3-(amino)butyl]amino]butyl]amino]carbonyloxy]-N-[6-[(aminoiminomethyl)amino] Hexyl]acetamide
[0188] 4.2g (5.05·10 -3 mol) The product obtained in the above preparation 13 was dissolved in 275 ml methanol, 0.25 ml concentrated hydrochloric acid was added, and then 0.25 g palladium chloride was added. The mixture was hydrogenated at room temperature and atmospheric pressure for 14 hours. The reaction medium was filtered and concentrated under reduced pressure. The obtained oil was dissolved in 100ml of water and 1ml of trifluoroacetic acid, and then the solution was washed 3 times with 75ml of ethyl acetate each time, and lyophilized to obtain 3.9g (yield=99%) of the desired product as an amorphous solid .
[0189] 1 H NMR(DMSO-d 6 ): 1.2 (d, 3H); 1.25-1.70 (m, 12H); 1.70-1.9 (m, 1H); 1.9-2.05 (m, 1H); 2.85-3.15 (m, 11H); 4.3 (s, 2H) ); 6.8-7.5 (m, 5H); 7.6-7.75 (t, 1H); 7.85-7.95 (t, 1H); 7.95-8.20 (bs, 3H); 8.70-8.90 (bs, 2H).
[0190] ...
Embodiment 3
[0200] Tris(trifluoroacetic acid)N-[4-[[3-(amino)butyl]amino]butyl]-N′-[8-[(aminoiminomethyl)amino]octyl]malonamide
[0201] Using a method similar to Example 1, except that 2.15g (3.01·10 -3 mol) The compound obtained in Preparation 15 was used as the raw material, and the mixture of water / acetonitrile / trifluoroacetic acid (7.5 / 2 / 0.5 v / v) was used as the eluent. After purification on RP18 silica gel, 2.05g was obtained (yield=90% ) The desired product is an amorphous solid.
[0202] 1 H NMR(DMSO-d 6 ): 1.18(d, 3H); 1.2-1.65(m, 16H); 1.65-1.8(m, 1H); 1.8-2(m, 1H); 2.8-3.1(m, 12H); 3.25-3.3(m , 1H); 6.8-7.5 (bs, 3H); 7.55 (t, 1H); 7.85-8.1 (m, 5H); 8.45-8.65 (m, 3H).
[0203] 13 C NMR(D 2 O): 18.01; 23.69; 26.24; 26.51; 26.69; 28.60; 28.92; 28.96; 32.21; 39.49; 40.46; 41.97; 44.31; 44.59; 46.10; 48.14; 157.89; 169.96; 170.34.
[0204] Preparation 16
[0205] 3-[[(1,1-Dimethylethoxy)carbonyl]amino]-23-methyl-20-(phenylmethyl)-13-(phenylmethoxy)-12,14-diox Hydrogen-2,4,11,15,20,24-he...
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