Method for production of novel galeterone analogs and uses thereof
AssigneeUniversity of Maryland, Baltimore
InventorsVincent C.O. Njar, Puranik Purushottamachar, Francis Murigi
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Abstract
Galeterone and its C-3 analogs are of substantial interest because of their multi-target anticancer activities, including AR and Mnk degrading activities. Provided are novel procedures for gram-scale, high-yield synthesis of C-3 analogs of galeterone, including 3β-(1H-imidazole-1-yl)-17-(1H-benzimidazole-1-yl)-androsta-5,16-diene (galeterone 3β-imidazole) and 3β-(pyridine-4-ylmethoxy)-17-(1H-benzimidazol-1-yl)androsta-5,16-diene (galeterone 3β-pyridine methoxylate).
Claims20
A process for preparing 3-(1H-imidazole-1-yl)-17-(1H-benzimidazole-1-yl)-androsta-5,16-diene (2, 5), the process comprising:
- a first reaction comprising reacting a compound having Formula 1 (1)
- to produce 3-azido-17-(1H-benzimidazole-1-yl)-androsta-5,16-diene (7, 8);
- and
- a second reaction comprising reacting the 3-azido-17-(1H-benzimidazole-1-ypandrosta-5,16-diene (7, 8) to produce 3-(1H-imidazole-1-yl)-17-(1H-benzimidazole-1-yl)-androsta-5,16-diene (2, 5).
A process for preparing galeterone 3β-pyridine methoxylate (3), the process comprising contacting a compound having Formula 1 (1)
- with 4-(bromomethyl)pyridine hydrobromide in the presence of a suitable base, a suitable salt, and at least one suitable solvent to produce the galeterone 3β-pyridine methoxylate (3).
A process for preparing an androgen receptor degrading agent or a MAPK-interacting kinase degrading agent, the process comprising preparing a compound having Formula 2 (7) or a compound having Formula 3 (8):
Dependencies are inferred from the claim text.