Tricyclic 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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[0114] Among the aspects of the invention set forth above in the Summary of the Invention, certain embodiments of these aspects are preferred.
[0115] One aspect of the present invention is the compound of general formula (I) as set forth in the Summary of the Invention above, its stereoisomers, enantiomers, tautomers or mixtures thereof; or its pharmaceutically acceptable salts, Solvates or Prodrugs.
[0116] One embodiment of this aspect are compounds of general formula (I) as set forth above in the Summary of the Invention, wherein:
[0117] n and m are each independently 0, 1 or 2;
[0118] R 1 with R 2 Each independently is a chemical bond, -C(R 9 ) 2 -, -S-, -O-, -C(O)-, -N(R 9 )-or-CH 2 -R 10 -CH 2 -;
[0119] R 3 with R 4 same, and selected from -R 11 -S-C(=NR 12 )N(R 12 )R 13 ,-R 11 -O-C(=NR 12 )N(R 12 )R 13 ,-R 11 -C(=NR 12 )N(R 12 )R 13 or -R 11 -N(R 9 )-C(=NR 12 )N(R 12 )R 13 ;
[0120] R 5 with R 6 Same, and selected from hydrogen,...
Embodiment 1
[0836] Synthesis of dibenzo[b,d]thiophene-4,6-diylbis(methylene)diisothiourea dihydrobromide
[0837]
[0838]To a solution of 4,6-bis(bromomethyl)dibenzo[b,d]thiophene (0.19 g, 0.50 mmol) in ethanol (10 mL) was added thiourea (0.076 g, 1.0 mmol) . The mixture was maintained at 80°C for 14 hours and cooled to ambient temperature. Ethanol was removed to one-third of the original volume, and hexane was added. The precipitated solid was collected by filtration, washed with ether and ethyl acetate, and dried in air to give dibenzo[b,d]thiophene-4,6-diylbis(methylene)diisothiourea Dihydrobromide, yield 84% (0.22 g): 1 H NMR (300MHz, DMSO-d 6 )δ9.34 (brs, 4H), 9.13 (brs, 4H), 8.40 (d, J=7.7Hz, 2H), 7.64 (d, J=7.7Hz, 2H), 7.57 (dd, J=7.7, 7.7Hz, 2H), 4.81(s, 4H); 13 C NMR (75MHz, DMSO-d 6 ) δ 169.3, 138.3, 136.6, 129.1, 128.9, 126.3, 123.0, 34.5; MS (ES+) m / z 361.1 (M+1).
Embodiment 11
[0840] Synthesis of (3,7-dibromodibenzo[b,d]thiophene-4,6-diyl)bis(methylene)diisothiourea dihydrobromide
[0841]
[0842] Following the procedure as described in Example 1, with non-critical changes, 3,7-dibromo-4,6-bis(bromomethyl)dibenzo[b,d]thiophene was used instead of 4,6- Bis(bromomethyl)dibenzo[b,d]thiophene to obtain (3,7-dibromodibenzo[b,d]thiophene-4,6-diyl)bis(methylene)diisosulfur Urea dihydrobromide, a colorless solid, yield 85%: melting point > 220°C; 1 H NMR (300MHz, DMSO-d 6 )δ9.62-9.16 (br s, 8H), 8.37 (d, J = 8.4Hz, 2H), 7.89 (d, J = 8.4Hz, 2H), 4.90 (s, 4H); 13 C NMR (75MHz, DMSO-d 6 ) δ 169.4, 140.8, 135.5, 131.0, 127.0, 125.0, 124.2, 36.0; MS (ES+) m / z 517.1 (M+1), 519.1 (M+1), 521.1 (M+1).
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