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Last Updated: March 28, 2024

Claims for Patent: 5,587,497


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Summary for Patent: 5,587,497
Title: 19-nor-vitamin D compounds
Abstract:This invention provides a novel class of vitamin D-related compounds, namely the 1.alpha.-hydroxy-19-nor-vitamin D analogs, as well as a general method for their chemical synthesis. The compounds exhibit pronounced activity in arresting the proliferation of undifferentiated cells, including malignant cells, and in inducing their differentiation, and thus represent novel therapeutic agents for the treatment of malignant and other diseases characterized by the proliferative growth of undifferentiated cells. Formulations for therapeutic use and treatment methods are also provided. The 19-nor vitamin D compounds have the formula: ##STR1## where X.sup.1 and X.sup.2 are each hydrogen or a hydroxy protecting group and R is a side chain.
Inventor(s): DeLuca; Hector F. (Deerfield, WI), Schnoes; Heinrich K. (Madison, WI), Perlman; Kato L. (Madison, WI), Sicinski; Rafal R. (Warsaw, PL), Prahl; Jean M. (Madison, WI)
Assignee: Wisconsin Alumni Research Foundation (Madison, WI)
Application Number:08/442,492
Patent Claims: 1. A compound having the formula ##STR10## where X.sup.1 and X.sup.2 are each selected from hydrogen, acyl, alkylsilyl and alkoxyalkyl, and where R is selected from alkyl, hydrogen, hydroxyalkyl, said hydroxyalkyl having from 4 to 5 carbon atoms, fluoroalkyl and a side chain of the formula ##STR11## wherein R.sup.1 represents hydrogen, hydroxy or O-acyl, R.sup.2 and R.sup.3 are each selected from alkyl, hydroxyalkyl and fluoroalkyl, or, when taken together represent the group --(CH.sub.2).sub.m --where m is an integer having a value of from 2 to 5, R.sup.4 is selected from hydrogen, hydroxy, fluorine, O-acyl, alkyl, hydroxyalkyl and fluoroalkyl, R.sup.5 is selected from hydrogen, fluorine, alkyl, hydroxyalkyl and fluoroalkyl, or R.sup.4 and R.sup.5 taken together represent double-bonded oxygen, R.sup.6 and R.sup.7 are each selected from hydrogen, hydroxy, O-acyl, fluorine and alkyl, or, R.sup.6 and R.sup.7 taken together form a carbon-carbon double bond, and wherein n is an integer having a value of from 1 to 5 and wherein any of the groups -CH(CH.sub.3)-, -CH(R.sup.7)-, or -CH(R.sup.6)- at positions 20, 22 and 23, respectively, may be replaced by an oxygen atom, with the proviso that when n is 2 to 5 each R.sup.4 is independently selected from hydrogen, hydroxy, fluorine, O-acyl, alkyl, hydroxyalkyl and fluoroalkyl, and each R.sup.5 is independently selected from hydrogen, fluorine, alkyl, hydroxyalkyl and fluoroalkyl.

2. A compound according to claim 1 where X.sup.1 and X.sup.2 represent hydrogen, and where R.sup.1 is hydroxy, both of R.sup.2 and R.sup.3 are selected from the group consisting of methyl, trifluoromethyl, ethyl and propyl, both of R.sup.6 and R.sup.7 are hydrogen, or together form a carbon-carbon double bond, R.sup.4 and R.sup.5 are hydrogen and n is an integer having the values 1, 2 or 3.

3. The compound of claim 1 where R is a side chain of the formula ##STR12##

4. The compound of claim 1 where R is a side chain of the formula ##STR13##

5. The compound of claim 1 where R is a side chain of the formula ##STR14##

6. The compound of claim 1 where R is a side chain of the formula ##STR15##

7. 1.alpha.,25-dihydroxy-19-nor-vitamin D.sub.3.

8. 1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

9. 1.alpha.,25-dihydroxy-19-nor-vitamin D.sub.2 .

10. 1.alpha.-hydroxy-19-nor-vitamin D.sub.2.

11. 1.alpha.-hydroxy-19-nor-24 epi-vitamin D.sub.2.

12. 1.alpha.,25-dihydroxy-19-nor-24 epi-vitamin D.sub.2.

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