18-substituted-19-nor-vitamin D compounds

Details 18-substituted-19-nor-vitamin D compounds 18-substituted-19-nor-vitamin D compounds

1997-07-21

1999-08-17

Dees, Jose' G.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

9,10-seco- cyclopentanohydrophenanthrene ring system doai

552653, A01N 4500, C07C40100

Patent

active

059394064

ABSTRACT:
This invention provides a novel class of vitamin D compounds, namely, 13-ethyl and 13-vinyl-18,19-dinor-vitamin D derivatives, as well as a general method for their chemical synthesis. The compounds have the formula: ##STR1## where Y.sub.1 and Y.sub.2, which may be the same or different, are each selected from the group consisting of hydrogen and a hydroxy-protecting group, R.sub.6 is selected from the group consisting of an ethyl or vinyl radical, and where the group R represents any of the typical side chains known for vitamin D type compounds. These 18-substituted compounds are characterized by minimal intestinal calcium transport activity and minimal bone calcium mobilization activity resulting in novel therapeutic agents for the treatment of secondary hyperparathyroidism. These compounds also exhibit pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as anti-cancer agents and for the treatment of diseases such as psoriasis.

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Valles et al, "Functionalization of Vitamin D Metabolites at C-18 and Application to the Synthesis of 1.alpha.,18,25-Trihydroxyvitamin D.sub.3 and 18,25-Dihydroxyvitamin D.sub.3 ", Tetrahedron Letters, vol. 33, No. 11, pp. 1503-1506, 1992.
Maynard et al, "18-Substituted Derivatives of Vitamin D: 18-Acetoxy-1.alpha.,25-Dihydroxyvitamin D.sub.3 and Related Analogues", J. Org. Chem., 57, pp. 3214-3217, 1992.
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