Biaryl and biheteroaryl compounds useful in treating iron disorders
A technology of compounds and mixtures, applied in the field of divalent metal transporter-1 inhibitors, which can solve problems such as tissue damage and increased risk
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[0106] Within the various aspects of the invention described above in the Summary of the Invention, certain embodiments are preferred.
[0107] Among the compounds of general formula (I) described above in the summary of the invention, one embodiment is a compound of general formula (Ia):
[0108]
[0109] in:
[0110] R 1 is a chemical bond, -O-, -S(O) p -(where p is 0, 1 or 2), -C(R 4 ) 2 -, -C(O)- or -N(R 4 )-;
[0111] R 2a , R 2b , R 2c , R 2d and R 2e each independently selected from hydrogen, alkyl, halogen, haloalkyl, -R 6 -OR 7 ,-R 6 -CN, -R 6 -NO 2 ,-R 6 -N(R 8 ) 2 ,-R 6 -C(O)OR 8 ,-R 6 -C(O)N(R 8 ) 2 , -N(R 8 )S(O) t R 9 ,-S(O) t OR 9 ,-S(O) p R 8 ,-S(O) t N(R 8 ) 2 ,-R 6 -S-C(=NR 4 )N(R 4 )R 5 ,-R 6 -O-C(=NR 4 )N(R 4 )R 5 ,-R 6 -C(O)-N=C[N(R 4 )(R 5 )]N(R 4 )R 5 ,-R 6 -C(=NR 4 )N(R 4 )R 5 and -R 6 -N(R 7 )-C(=NR 4 )N(R 4 )R 5 , wherein each t is independently 1 or 2 and each p is 0, 1 or 2 and wherein R 2a ...
Embodiment 1
[1216] Synthesis of 2-(1-{2-[2-(1-amidinothioethyl)phenoxy]phenyl}ethyl)isothiouronium dihydrobromide
[1217]
[1218] To a stirred suspension of thiourea (0.17 g, 0.22 mmol) in water was added 48% aqueous hydrobromic acid. The mixture was stirred for 10 min, then 1-(1-hydroxyethyl)-2-(6-(1-hydroxyethyl)phenoxy)benzene (0.26 g, 0.10 mmol) was added in one portion. The mixture was stirred at 80 °C for 3 h and cooled to ambient temperature. Diethyl ether (2.0 mL) was added to the mixture. The solid was collected by filtration and dried in air to give 2-(1-{2-[2-(1-amidinothioethyl)phenoxy]phenyl}ethyl)isothiourea dihydrogen bromide acid salt (0.19g), yield 54%: 1 H NMR (300MHz, DMSO-d 6 )δ9.22(s, 4H), 9.03(s, 4H), 7.64(d, J=8.8Hz, 2H), 7.35(t, J=7.0Hz, 2H), 7.22(t, J=7.5Hz, 2H), 6.75(d, J=8.2Hz, 2H), 6.22(s, 2H), 5.44(q, J=6.8Hz, 2H), 1.76(d, J=6.8Hz, 6H); MS(ES+) m / z358.6(M+1).
Embodiment 11
[1220] Synthesis of 2-[2-(2-amidinothiomethylphenylthio)benzyl]isothiouronium dihydrobromide
[1221]
[1222] According to the procedure as described in Example 1, with non-critical changes, 1-(hydroxymethyl)-2-((6-(hydroxymethyl)phenyl)thio)benzene was used instead of 1-(1 -Hydroxyethyl)-2-(6-(1-hydroxyethyl)phenoxy)benzene to give 2-[2-(2-amidinothiomethylphenylthio) as a colorless solid Benzyl]isothiouronium dihydrobromide, the yield is 74%: 1 H NMR (300MHz, DMSO-d 6 )δ9.28(s, 4H), 9.10(s, 4H), 7.63-7.59(m, 2H), 7.41-7.32(m, 4H), 7.15-7.10(m, 2H), 4.65(s, 4H) ; MS (ES+) m / z 363.6 (M+1).
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