New Vitamin D derivatives with cyclopropyl rings in the side chains, process and intermediate products for their production and their use for the production of pharmaceutical agents

Abstract

The invention relates to new vitamin D derivatives of general formula (I), process for their production, intermediate products of the process as well as the use for production of pharmaceutical agents.

1 . Vitamin D derivatives of general formula I,  
       
         
           
           
               
               
           
         
       
       in which 
 Y 1  means a hydrogen atom, a hydroxyl group, a fluorine, chlorine or bromine atom or a group —OCOR 8 , in which R 8  is an aliphatic or aromatic radical with 1 to 12 C atoms,  
 Y 2  means a hydrogen atom or a group —(CO)R 9 , in which R 9  is an aliphatic or aromatic radical with 1 to 12 C atoms,  
 R 1  and R 2  a hydrogen atom or together an exocyclic methylene group,  
 R 3  and R 4 , independently of one another, mean a hydrogen atom, a chlorine or fluorine atom, an alkyl group with 1 to 4 carbon atoms, together a methylene group or together with quaternary carbon atom 20 a 3- to 7-membered, saturated or unsaturated carbocyclic ring,  
 V and W together mean an E-double bond or V means a hydroxyl group and W means a hydrogen atom,  
 Q means a straight-chain or branched carbon unit with up to 10 carbon atoms, which at any positions can have α- or β-hydroxyl groups, which in turn can be etherified or esterified, keto groups, amino groups or halogen atoms,  
 Z means a straight-chain or branched-chain, saturated or unsaturated hydrocarbon radical with up to 12 carbon atoms, which at any positions can have keto groups, α- or β-hydroxyl groups, which in turn can be etherified or esterified, amino groups, fluorine, chlorine, or bromine atoms.  
 
     
     
         2 . Vitamin D derivatives of general formula I according to  claim 1 , in which Q means an unsubstituted, unbranched alkylene unit with 1 or 2 carbon atoms, and Z means a straight-chain 1-oxoalkyl radical.  
     
     
         3 . Vitamin D derivatives of general formula I according to  claim 1 , in which Q means a —CH(OH)—CH 2 —CH 2  radical, and Z means a straight-chain 1-oxoalkyl radical.  
     
     
         4 . Vitamin D derivatives of general formula I according to  claim 1 , in which Q means a hydroxymethyl group and Z means a straight-chain, saturated or unsaturated alkyl group.  
     
     
         5 . Vitamin D derivatives of general formula I according to  claim 1 , namely 
 (5Z,7E,22E)-(1S,3R)-25-Acetyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxopropyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxobutyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxopentyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxohexyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxoheptyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxooctyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxononyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxodecyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E)-(1S,3R,22S)-25-acetyl-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-acetyl-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxopropyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxopropyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxobutyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxobutyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxopentyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxopentyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxohexyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R) -25-(1-oxohexyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxoheptyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxoheptyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxooctyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxooctyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxononyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxononyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxodecyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxodecyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E,22E)-(1S,3R)-25-acetyl-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxopropyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxobutyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxopentyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxohexyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxoheptyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxooctyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxononyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R)-25-(1-oxodecyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E)-(1S,3R,22S)-25-acetyl-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-acetyl-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxopropyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxopropyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxobutyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxobutyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxopentyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxopentyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxohexyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxohexyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxoheptyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxoheptyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxooctyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxononyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxononyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22S)-25-(1-oxodecyl)-26,27-cyclo-24a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E)-(1S,3R,22R)-25-(1-oxodecyl)-26,27-cyclo-24a-homo--9,10-secocholesta-5,7,10(19)-triene-1,3,22-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-acetyl-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-acetyl-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-(1-oxopropyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-(1-oxopropyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-(1-oxobutyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-(1-oxobutyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-(1-oxopentyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-(1-oxopentyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-(1-oxohexyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-(1-oxohexyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-(1-oxoheptyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-(1-oxoheptyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-(1-oxooctyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-(1-oxooctyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-(1-oxononyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-(1-oxononyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-(1-oxodecyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-(1-oxodecyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-acetyl-24-methoxy-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24S)-25-acetyl-24-methoxy-26,27-cyclo-24a,24b-dihomo-9,10-secbcholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24R)-24-methoxy-25-(1-oxopropyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24S)-24-methoxy-25-(1-oxopropyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24R)-24-methoxy-25-(1-oxobutyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24S)-24-methoxy-25-(1-oxobutyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24R)-24-methoxy-25-(1-oxopentyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24S)-24-methoxy-25-(1-oxopentyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24R)-24-methoxy-25-(1-oxohexyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24S)-24-methoxy-25-(1-oxohexyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24R)-24-methoxy-25-(1-oxoheptyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24S)-24-methoxy-25-(1-oxoheptyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24R)-24-methoxy-25-(1-oxooctyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24S)-24-methoxy-25-(1-oxooctyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24R)-24-methoxy-25-(1-oxononyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24S)-24-methoxy-25-(1-oxononyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24R)-24-methoxy-25-(1-oxodecyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24S)-24-methoxy-25-(1-oxodecyl)-26,27-cyclo-24a,24b-dihomo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3-diol,    (5Z,7E,22E)-(1S,3R,24S)-25-methyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-methyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-ethyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-ethyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-propyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-propyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-butyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-butyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-pentyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-pentyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-hexyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-hexyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-heptyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-heptyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-octyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-nonyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-nonyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-decyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-decyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24S)-25-ethylene-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    (5Z,7E,22E)-(1S,3R,24R)-25-ethylene-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24S)-25-(1-propenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24R)-25-(1-propenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24S)-25-(1-butenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24R)-25-(1-butenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24S)-25-(1-pentenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24R)-25-(1-pentenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24S)-25-(1-hexenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24R)-25-(1-hexenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24S)-25-(1-heptenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24R)-25-(1-heptenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24S)-25-(1-octenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24R)-25-(1-octenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24S)-25-(1-nonenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24R)-25-(1-nonenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24S)-25-(1-decenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(E)]-(1S,3R,24R)-25-(1-decenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24S)-25-(1-propenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24R)-25-(1-propenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24S)-25-(1-butenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24R)-25-(1-butenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24S)-25-(1-pentenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24R)-25-(1-pentenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24S)-25-(1-hexenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24R)-25-(1-hexenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24S)-25-(1-heptenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24R)-25-(1-heptenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24S)-25-(1-octenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24R)-25-(1-octenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24S)-25-(1-nonenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24R)-25-(1-nonenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24S)-25-(1-decenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol,    [5Z,7E,22E,25(Z)]-(1S,3R,24R)-25-(1-decenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol.    
     
     
         6 . Process for the production of vitamin D derivatives of general formula I, whereby a compound of general formula II  
       
         
           
           
               
               
           
         
       
       in which 
 Y′ 1  means a hydrogen atom, a halogen atom, or a protected hydroxyl group and Y′ 2  means a hydroxy protective group, is converted into the compound of general formula I by simultaneous or successive cleavage of the hydroxy and keto protective groups and optionally by partial or complete esterification of free hydroxyl groups.  
 
     
     
         7 . Use of the vitamin D derivatives of general formula I for the production of pharmaceutical agents.  
     
     
         8 . Use of the vitamin D derivatives of general formula I according to  claim 7  for the production of pharmaceutical agents for the therapy of hyperproliferative diseases of the skin, pruritus, tumor diseases, precancerous stages, disorders of the immune system, inflammatory diseases, rheumatoid arthritis, asthma, auto-immune diseases, multiple sclerosis, diabetes mellitus, AIDS as well as rejection reactions in the case of autologous, allogeneic or xenogeneic transplants.  
     
     
         9 . Use according to  claim 8 , wherein the pharmaceutical agent also is combined with other substances that have an immunosuppressive action, such as cyclosporin A, FK 506, rapamycin and anti-CD 4 antibodies.  
     
     
         10 . Use of the vitamin D derivatives of general formula I according to  claim 7  for the production of pharmaceutical agents for the therapy of atrophic skin or wound healing, the therapy of secondary hyperparathyroidism, renal osteodystrophia, as well as senile and postmenopausal osteoporosis, diabetes mellitus type II and the therapy of degenerative diseases of the peripheral and central nervous system as well as the regulation of hair growth.  
     
     
         11 . Use of vitamin D derivatives of general formula I according to  claim 7 , which antagonize the action of calcitriol in HL 60 cells, for the therapy of hypercalcemias or granulomatous diseases, of paraneoplastic hypercalcemias, of hypercalcemia in the case of hyperparathyroidism, for male and female birth control or as immunostimulants, as well as in hirsutism, for the therapy and prophylaxis of arteriosclerosis, and for the therapy of inflammatory diseases.  
     
     
         12 . Intermediate products of general formula XII within the production of vitamin D derivatives of general formula I according to  claim 1:   
       
         
           
           
               
               
           
         
       
       in which 
 R 6  means a straight-chain or branched alkyl group with up to 11 carbon atoms or a hydrogen atom, and K means a keto protective group.  
 
     
     
         13 . Intermediate product according to  claim 10 , wherein K stands for 1,3-dioxolan, 1,3-dioxane, 5,5-methyl-1,3-dioxane or a dialkoxyketal.