Amino derivatives of androstanes and androstenes as medicaments for cardiovascular disorders
A technology of androstane and alkyl groups, applied in the field of new amino derivatives, can solve problems such as side effects
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Embodiment 1
[0362] (E, Z) 3-(2-Aminoethoxyimino)-17-oxoandrostane-6α-yl fumarate nitrate Ester (I-aa)
[0363] To a stirred THF solution (30 mL) of 3,17-dioxoandrostane-6α-ylnitrate (II-aa, Preparation 1, 1.14 g) was rapidly added dropwise 2-aminoethoxyamino di Hydrochloride (223mg), Na 2 HPO 4 12H 2 O (2.30 g) in water (11.6 mL). After 1.5 hours, NaCl (1.8 g) was added and the mixture was stirred for 10 minutes. The phases were separated and the aqueous phase was extracted with THF (2x). The combined organic extracts were washed with Na 2 SO 4 Dry, filter and evaporate to dryness. By flash chromatography (SiO 2 , CHCl 3 / MeOH / 26% NH4OH 90 / 10 / 1) to purify the crude product. To this concentrated fraction was added a stoichiometric amount of fumaric acid in MeOH. Add EtOAc / Et 2 After a 1 / 1 mixture of O, the precipitate was filtered to give the title compound I-aa (0.57 g, 33%) as a white solid. 1 H-NMR (300MHz, DMSO-d 6 , ppm from TMS): δ 8.76 (bb, 4H), 6.41 (s, 1H), 4.98 ...
Embodiment 2
[0365] (E, Z) 3-(2-Aminoethoxyimino)-17-oxoandrostane-6β-ylfumarate nitrate Ester (I-ab)
[0366] Starting from 3,17-dioxoandrostane-6β-ylnitrate (II-ab, preparation 2) and 2-aminoethoxyamino dihydrochloride as described in Example 1, at 60% prepared in high yields. 1 H-NMR (300MHz, DMSO-d 6 , ppm from TMS): δ 8.41 (bb, 4H), 6.40 (s, 2H), 5.23 (m, 0.5H), 5.19 (m, 0.5H), 4.03 (m, 2H), 3.05 (m, 1H ), 2.96 (m, 2H), 2.45-0.70 (m, 19H), 1.00 (s, 1.5H), 0.99 (s, 1.5H), 0.80 (s, 3H).
Embodiment 3
[0368] (E, Z) 3-(2-Aminoethoxyimino)-6α-cyanoandrostan-17-one fumarate (I-ac)
[0369] Starting from 6α-cyanoandrostane-3,17-dione (II-ac, preparation 3) and 2-aminoethoxyamino dihydrochloride as described in Example 1, in 65% yield prepared. 1 H-NMR (300MHz, DMSO-d 6 , ppm from TMS): δ 9.07 (bb, 4H), 6.40 (s, 2H), 4.07 (m, 2H), 3.24 (m, 0.5H), 3.06 (m, 0.5H), 2.99 (m, 2H ), 2.77 (m, 1H), 2.45-0.70 (m, 19H), 0.88 (s, 1.5H), 0.87 (s, 1.5H), 0.77 (s, 3H).
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