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2-alkyl-19-nor-vitamin D compounds

  • US 6,277,837 B1
  • Filed: 12/03/1999
  • Issued: 08/21/2001
  • Est. Priority Date: 03/17/1997
  • Status: Expired due to Term
First Claim
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1. A method of treating psoriasis comprising administering to a patient with said disease an effective amount of a compound having the formula:

  • where Y1 and Y2, which may be the same or different, are each selected from the group consisting of hydrogen and a hydroxy-protecting group, R6 is selected from alkyl, hydroxyalkyl and fluoroalkyl, and where the group R is represented by the structure;

    where the stereochemical center at carbon 20 may have the R or S configuration, and where Z is selected from Y, —

    OY, —

    CH2OY, —

    C≡

    -CY and —

    CH═

    CHY, where the double bond may have the cis or trans geometry, and where Y is selected from hydrogen, methyl, —

    COR5 and a radical of the structure;

    were m and n, independently, represent the integers from 0 to 5, where R1 is selected from hydrogen, hydroxy, protected hydroxy, fluoro, trifluoromethyl, and C1-5-alkyl, which may be straight chain or branched and, optionally, bear a hydroxy or protected-hydroxy substituent, and where each of R2, R3, and R4, independently, is selected from deuterium, deuteroalkyl, hydrogen, fluoro, trifluoromethyl and C1-5 alkyl, which may be straight-chain or branched, and optionally, bear a hydroxy or protected-hydroxy substituent, and where R1 and R2, taken together, represent an oxo group, or an alkylidene group, ═

    CR2R3, or the group —

    (CH2)p

    , where p is an integer from 2 to 5, and where R3 and R4, taken together, represent an oxo group, or the group —

    (CH2)q

    , where q is an integer from 2 to 5, and where R5 represents hydrogen, hydroxy, protected hydroxy, or C1-5 alkyl and wherein any of the CH-groups at positions 20, 22, or 23 in the side chain may be replaced by a nitrogen atom, or where any of the groups —

    CH(CH3)—

    , —

    CH(R3)—

    , or —

    CH(R2)—

    at positions 20, 22, and 23, respectively, may be replaced by an oxygen or sulfur atom.

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