Fluorinated vitamin D.sub.3 compounds
AssigneeHoffmann-La Roche Inc.
InventorsEnrico Baggiolini, Giacomo Pizzolato, Milan Uskokovic, Gary Truitt
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Abstract
Novel hexafluoro-cholecalciferol compounds and processes for preparing such compounds are disclosed. Intermediates utilized in the preparation of such compounds and pharmaceutical preparations containing these compounds are also disclosed.
Claims14
26,26,26,27,27,27-Hexafluoro-1.alpha.,25-dihydroxy-.DELTA..sup.22 -cholecalciferol.
26,26,26,27,27,27-Hexafluoro-1.alpha.,25-dihydroxy-.DELTA..sup.23 cholecalciferol.
A compound of the formula ##STR5## where X is aryl;
- and R.sub.1, R.sub.2 and R.sub.3 each independently are lower alkyl, aryl and aralkyl.
A pharmaceutical composition suitable for oral administration said composition comprising a minor, effective amount of 26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxy-.DELTA..sup.22 -cholecalciferol and a major amount of a conventional pharmaceutical carrier material suitable for oral administration.
A pharmaceutical composition suitable for oral administration said composition comprising a minor, effective amount of 26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxy-.DELTA..sup.23 -cholecalciferol and a major amount of a conventional pharmaceutical carrier material suitable for oral administration.
A pharmaceutical composition suitable for parenteral administration said composition comprising a minor, effective amount of 26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxy-.DELTA..sup.22 -cholecalciferol and a major amount of a conventional pharmaceutical carrier material suitable for parenteral administration.
A pharmaceutical composition suitable for parenteral administration said composition comprising a minor, effective amount of 26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxy-.DELTA..sup.23 -cholecalciferol and a major amount of a conventional pharmaceutical carrier material suitable for parenteral administration.
A process for producing 26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxy-.DELTA..sup.22 -cholecalciferol which process comprises reacting a compound of the formula:
- ##STR6## with the carbanion of [3S-(3.alpha.,5.beta.,Z)]-2-[2-methylene-3,5-bis[(1,1-dimethylethyl)dimeth ylsilyloxy]cyclohexylidene]-ethyldiphenyl phosphine oxide and removing the silyl protecting groups.
A process for producing 26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxy-.DELTA..sup.23 -cholecalciferol which process comprises reacting a compound of the formula:
- ##STR7## with the carbanion of [3S-(3.alpha.,5.beta.,Z)]-2-[2-methylene-3,5-bis[1,1-dimethylethyl)dimethy lsilyloxy]cyclohexylidene]-ethyldiphenyl phosphine oxide and removing the silyl protecting groups.
[1R-[1.beta.(R*),3a.a lpha.,4.beta.,7a.beta.]]-octahydro-1-[6,6,6-trifluoro-5-(trimethylsilyloxy) -5-(trifluoromethyl)-1-methyl-2-hexenyl]-7a-methyl-1H-inden-4-one.
[1R-[1.beta.(R*),3a.alpha.,4.beta.,7a.beta.]]-octahydro-1-[6,6 ,6-trifluoro-5-(trimethylsilyloxy)-5-trifluoromethyl)-1-methyl-3-hexenyl]-7 a-methyl-1H-inden-4-one.
A compound of the formula ##STR8##
A compound of the formula ##STR9##
Dependencies are inferred from the claim text.