19-nor neuroactive steroids and methods of use thereof
a neuroactive steroid and neuroactive technology, applied in the field of neuroactive steroids, can solve the problems that progesterone is not consistently effective in the treatment of the aforementioned syndromes, and achieve the effects of preventing further metabolism, reducing the potential for oxidation of the hydroxy moiety, and reducing the risk of side effects
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example 1
Synthesis of SA and SA Intermediates
[0285]
Synthesis of Compound SA-B
[0286]Compound SA (50 g, 184 mmol) and palladium black (2.5 g) in tetrahydrofuran (300 mL) and concentrated hydrobromic acid (1.0 mL) was hydrogenated with 10 atm hydrogen. After stirring at room temperature for 24 h, the mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to afford the crude compound.
[0287]Recrystallization from acetone gave compound SA-B (42.0 g, yield: 83.4%) as white powder.
[0288]1H NMR: (400 MHz, CDCl3) δ 2.45-2.41 (m, 1H), 2.11-3.44 (m, 2H), 3.24 (s, 3H), 2.18-2.15 (m, 1H), 2.01-1.95 (m, 1H), 1.81-1.57 (m, 7H), 1.53-1.37 (m, 7H), 1.29-1.13 (m, 3H), 1.13-0.90 (m, 2H), 0.89 (s, 3H).
Synthesis of Compound SA-C
[0289]A solution of SA-B (42.0 g, 153.06 mmol) in 600 mL anhydrous toluene was added dropwise to the methyl aluminum bis(2,6-di-tert-butyl-4-methylphenoxide (MAD) (459.19 mmol, 3.0 eq, freshly prepared) solution under N2 at −78° C. After the addition was co...
example 2
Synthesis of SB and SB-J Intermediates
[0294]
Synthesis of Compounds SB-B and SB-C
[0295]Small pieces of lithium (7.63 g, 1.1 mol) were added to 2.7 L of condensed ammonia in a three neck flask at −70° C. As soon as all lithium was dissolved, the blue solution was warmed to −50° C. A solution of 19-norandrost-4-ene-3,17-dione SB-A (1, 30 g, 110 mmol) and tert-BuOH (8.14 g, 110 mmol) in 800 ml of anhydrous tetrahydrofuran was added dropwise and stirred for 90 min until the reaction mixture turned light yellow. Ammonium chloride (70 g) was added and excess ammonia was left to evaporate. The residue was extracted with 0.5N HCl (500 mL) and dichloromethane (500 mL×2). The combined organic layers were washed with saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated to give a mixture of SB-B and SBC (21 g, 70%) which was directly used in the next step without further purification. A solution of SB-B and SB-C (21 g, 76 mmol) in 50 mL of anhydrous dichloromethane was added ...
example 3
Synthesis of Compound SA-1
[0304]
[0305]To a suspension of K2CO3 (25 mg, 0.18 mmol) in THF (5 mL) was added 1-methylpiperazine (25 mg, 0.227 mmol) and SA (36 mg, 0.09 mmol). The mixture was stirred at rt for 15 h. The reaction mixture was poured in to 5 mL H2O and extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified with by reverse-phase prep-HPLC to afford the title compound SA-1 as a white solid (12 mg, 37.8%).
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