Functional vitamin D derivatives and a method for determining 25-hydroxy-vitamin D and 1α, dihydroxy-vitamin D
AssigneesImmundiagnostik AG, Biomedica GmbH
InventorsFranz Paul Armbruster, Wolfgang Voelter, Jens Tampe, Christian Birkmayer
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Abstract
Vitamin D compounds of formula (I) with a label attached to a spacer group in the 3 position are disclosed. In the above formula (I), X is an optionally substituted hydrocarbon group with a length of 0.8-4.2 nm, optionally containing the heteroatoms S, O, N or P; Y is H or OH; A is a label capable of binding with high affinity to a protein; R is an optionally substituted hydrocarbon side chain of a D vitamin or a D vitamin metabolite. Also disclosed is the preparation of formula (I).
Claims9
A method of obtaining a vitamin D compound of the formula:
- wherein:
- R represents a 25-hydroxy side-group of vitamin D2 or of vitamin D3;
- Y represents hydrogen or hydroxy;
- A represents a functional group, coupled via a spacer group, which can be bound by a protein with high affinity;
- comprising;
- a) cyanoethylating the 3-hydroxy group of a vitamin D starting compound in the presence of potassium hydride and tertiary butanol;
- b) adding lithium hydride and converting the 25-hydroxy group into the lithium alcoholate and subsequently reducing the nitrile group with lithium aluminum hydride;
- and
- c) linking a spacer group together with a functional group A on the amino propylether side chain.
A method of producing a 3-amino propylether-25-hydroxy or 3-amino propylether-1α,25-dihydroxy vitamin D intermediate compound, comprising;
- a) cyanoethylating the 3-hydroxy group of a vitamin D starting compound in the presence of potassium hydride and tertiary butanol;
- b) adding lithium hydride and converting the 25-hydroxy group into the lithium alcoholate and subsequently reducing the nitrile group with lithium aluminum hydride.
A vitamin D compound of the formula:
- wherein;
- R represents a 25-OH side group of vitamin D, or
- Y represents hydrogen or hydroxyl and
- X represents a substituted or non-substituted hydrocarbon group of 0.8 to 4.2 nm length, which optionally contains the heteroatoms S, O, N, and P.
Dependencies are inferred from the claim text.