Production of pure stereoisomers of tricyclo[5.2.1.02.6]-dec-9-yl-xanthogenate and medicaments therefrom
AssigneeLumavita AG
InventorEberhard Amtmann
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Abstract
The invention relates to pharmaceutical formulations containing exo/exo-tricyclo[5.2.1.02.6]-dec-9-yl-xanthogenate, drugs containing exo/exo-tricyclo[5.2.1.02.6]-dec-9-yl-xanthogenate as active ingredient for the treatment of genital herpes, labial herpes, AIDS, tumors or autoimmune diseases, and methods for the production of pure stereoisomers of tricyclo[5.2.1.02.6]-decan-9-ol and tricyclo[5.2.1.02.6]-dec-9-yl-xanthogenate.
Claims19
A pharmaceutical formulation comprising a xanthogenate corresponding to formula I
- wherein
- R1 corresponds to tricyclo[5.2.1.02.6]-dec-9-yl,
- R2 corresponds to a metal atom, ammonium, or substituted or unsubstituted alkyl;
- and at least 95% of said xanthogenate in said formulation is exo/exo-tricyclo[5.2.1.02.6]-dec-9-yl xanthogenate and no more than 5% of said xanthogenate in said formulation is any other possible isomer of said xanthogenate.
A method for the production of an isomer of tricyclo[5.2.1.02.6]decan-9-ol, comprising subjecting a mixture of tricyclo[5.2.1.02.6]decan-9-ol stereoisomers to fractional distillation under reduced pressure and collecting a distillate, wherein said collected distillate contains at least 95% of a single isomer of tricyclo[5.2.1.02.6]decan-9-ol and no more than 5% of any other isomer of tricyclo[5.2.1.02.6]decan-9-ol.
A method for the production of an isomer of tricyclo[5.2.1.02.6]dec-9-yl-xanthogenate, comprising the steps of:
- reacting a composition containing at least 95% of a single isomer of tricyclo[5.2.1.02.6]decan-9-ol and no more than 5% of any other isomer of tricyclo[5.2.1.02.6]decan-9-ol with an alkali metal or metal hydride to generate an alcoholate,
- dissolving the alcoholate in an inert solvent, and
- adding CS2 to the alcoholate to form an isomer of tricyclo[5.2.1.02.6]dec-9-yl-xanthogenate having at least 95% of a single isomer of tricyclo[5.2.1.02.6]dec-9-yl-xanthogenate and no more than 5% of any other isomer of tricyclo[5.2.1.02.6]dec-9-yl-xanthogenate.
A composition comprising a compound according to formula I
- wherein
- R1 corresponds to tricyclo[5.2.1.02.6]-dec-9-yl,
- R2 corresponds to a metal atom, ammonium, or substituted or unsubstituted alkyl;
- and at least 95% of said compound according to formula I in said composition is exo/exo-tricyclo[5.2.1.02.6]-dec-9-yl xanthogenate and no more than 5% of said compound in said composition is any other possible isomer of said xanthogenate.
Dependencies are inferred from the claim text.