Vitamin D compounds and method of preparing these compounds

Abstract

The invention relates to a new vitamin D compound of the general formula ##STR1## wherein: R 1 is a hydrogen atom or a hydroxy group; R 2 is a (C 1 -C 3 )alkyl group, a hydroxy(C 1 -C 3 )alkyl group, a (C 1 -C 2 )alkoxymethyl group or a (C 2 -C 3 )alkenyl or alkynyl group; R 3 is a branched or non-branched, saturated or unsaturated aliphatic 3- to 5 -membered hydrocarbon or oxahydrocarbon biradical, having at least 3 atoms in the main chain and being optionally substituted with one or more substituents selected from epoxy, fluoro and hydroxy; R 4 is a sec. or tert. (C 3 -C 6 )alkyl group or a (C 3 -C 6 )cycloalkyl group; and A and B are each individually hydrogen atoms or methyl groups, or A and B form together a methylene group. The invention further relates to a method of preparing these compounds and to their use in pharmacotherapy and cosmetics.

We claim: 
     
       1. A method for the treatment and prophylaxis of disease states selected from the group consisting of autoimmune diseases, .[.ache, alopecia,.]. .Iadd.acne, .Iaddend.skin aging, imbalance in the immune system, inflammatory diseases and diseases related to abnormal cell differentiation or proliferation, in a warm-blooded living being, comprising administering to said being or treating said being with a composition comprising at least one member selected from the group consisting of a pharmaceutically acceptable carrier and pharmaceutically acceptable auxiliary substances and mixtures thereof, and, as an active ingredient a compound of formula (1) ##STR25## wherein R 1  is a hydrogen atom or a hydroxy group; R 2  is a (C 1  -C 3 )alkyl group, a hydroxy(C 1  -C 3 )alkyl group, a (C 1  -C 2 )alkoxymethyl group or a (C 2  -C 3 )alkenyl or alkynyl group;   R 3  is a branched or non-branched, saturated or unsaturated aliphatic 3- to 5-membered hydrocarbon or oxahydrocarbon biradical, having at least 3 atoms in the main chain and being optionally substituted with one or more substituents selected from epoxy, fluoro and hydroxyl   R 4  is a sec. or tert. (C 3  -C 6 )alkyl group or a (C 3  -C 6 )cycloalkyl group; and   A and B are each individually hydrogen atoms or .[.ethyl.]. .Iadd.methyl .Iaddend.groups, or   A and B form together a methylene group in a quantity effective for the intended purpose.   
     
     
       2. A method as claimed in claim 1 wherein the disease treated is psoriasis which is a disease of abnormal cell proliferation. 
     
     
       3. A method of claim 2 wherein the active ingredient is of the formula ##STR26## 
     
     
       4. A method for the treatment and prevention of skin disorders in a warm-blooded living being, comprising treating said being with a cosmetical composition comprising at least one member selected from the group consisting of conventionally acceptable, non-toxic carriers and auxiliary substances and mixtures thereof, and, as the active ingredient a compound of formula (I) wherein: R 1  is a hydrogen atom or a hydroxy group;   R 2  is a (C 4  -C 3 )alkyl group, a hydroxy(C 1  -C 3 )alkyl group, a (C 1  -C 2 )alkoxymethyl group or a (C 2  -C 3 )alkenyl or alkynyl group;   R 3  is a branched or non-branched, saturated or unsaturated aliphatic 3- to 5-membered hydrocarbon or oxahydrocarbon biradical, having at least 3 atoms in the main chain and being optionally substituted with one or more substituents selected from epoxy, fluoro and hydroxy;   R 4  is a sec. or tert. (C 3  -C 6 )alkyl group or a (C 3  -C 6 )cycloalkyl group; and   A and B are each individually hydrogen atoms or .[.ethyl.]. .Iadd.methyl .Iaddend.groups, or   A and B form together a methylene group in an effective quantity.   
     
     
       5. A method for the treatment and prophylaxis of disease states selected from the group consisting of autoimmune diseases, .[.ache, alopecia,.]. .Iadd.acne, .Iaddend.skin aging, imbalance in the immune system, inflammatory diseases and diseases related to abnormal cell differentiation or proliferation, in a warm-blooded living being, comprising administering to said being or treating said being with a composition comprising at least one member selected from the group consisting of a pharmaceutically acceptable carrier and pharmaceutically acceptable auxiliary substances and mixtures thereof, and, as an active ingredient a compound of formula (1) ##STR27## wherein: R 1  is a hydroxy group; R 2  is a (C 1  -C 3 )alkyl group, a hydroxy(C 1  -C 3 )alkyl group, a   (C 1  -C 2 )alkoxymethyl group or a (C 2  -C 3 )alkenyl or alkynyl group;   R 3  is a biradical of the formula   --O--CH.sub.2 --(CH.sub.2).sub.n --, --CH.sub.2 --CH.sub.2 --(CH.sub.2).sub.n --, --CH═CH--(CH.sub.2).sub.n -- or --CH.sub.2 --CH.sub.2 --CH(CH.sub.3)--,       wherein n is 1 or 2;   R 4  is an isopropyl group, a cyclopropyl group or a tert.-butyl group; and   A and B are hydrogen atoms or form together a methylene group in a quantity effective for the intended purpose.   
     
     
       6. A method for the treatment and prophylaxis of disease states selected from the group consisting of autoimmune diseases, acne, .[.alopecia,.]. skin aging, imbalance in the immune system, inflammatory diseases and diseases related to abnormal cell differentiation or proliferation, in a warm-blooded living being, comprising administering to said being or treating said being with a composition comprising at least one member selected from the group consisting of a pharmaceutically acceptable carrier and pharmaceutically acceptable auxiliary substances and mixtures thereof, and, as an active ingredient at least one compound of formula (1) ##STR28## wherein: R 1  is a hydrogen atom or a hydroxy group; R 3  is a branched or non-branched, saturated or unsaturated aliphatic 3- to 5-branched hydrocarbon or oxahydrocarbon biradical, having at least 3 atoms in the main chain and being optionally substituted with one or more substituents selected from epoxy, fluoro and hydroxy;   R 4  is an isopropyl group   A and B are each individually hydrogen atoms or .[.ethyl.]. .Iadd.methyl .Iaddend.groups, or   A and B form together a methylene group in a quantity effective for the intended purpose.   
     
     
       7. A method as claimed in claim 5 wherein the disease treated is psoriasis which is a disease of abnormal cell proliferation. 
     
     
       8. A method as claimed in claim 6 wherein the disease treated is psoriasis which is a disease of abnormal cell proliferation. 
     
     
       9. A method for the treatment and prevention of skin disorders in a warm-blooded living being, comprising treating said being with a cosmetical composition comprising at least one member selected from the group consisting of conventionally acceptable, non-toxic carriers and auxiliary substances and mixtures thereof, and, as the active ingredient a compound of formula (I) ##STR29## wherein: R 1  is a hydroxy group; R 2  is a (C 1  -C 3 )alkyl group, a hydroxy(C 1  -C 3 )alkyl group, a (C 1  -C 2 )alkoxymethyl group or a (C 2  -C 3 )alkenyl or alkynyl group;   R 3  is a biradical of the formula   --O--CH.sub.2 --(CH.sub.2).sub.n --, --CH.sub.2 --C.sub.2 --(CH.sub.2).sub.n --, --CH═CH--(CH.sub.2).sub.n -- or --CH.sub.2 --CH.sub.2 --CH(CH.sub.3)--,       wherein n is 1 or 2;   R 4  is an isopropyl group, a cyclopropyl group or a tert.-butyl group; and   A and B are hydrogen atoms or form together a methylene group in a quantity effective for the intended purpose.   
     
     
       10. A method for the treatment and prevention of skin disorders in a warm-blooded living being, comprising treating said being with a cosmetical composition comprising at least one member selected from the group consisting of conventionally acceptable, non-toxic carriers and auxiliary substances and mixtures thereof, and, as the active ingredient a compound of formula (I) ##STR30## wherein: R 1  is a hydrogen atom or a hydroxy group; R 3  is a branched or non-branched, saturated or unsaturated aliphatic 3- to 5-membered hydrocarbon or oxahydrocarbon biradical, having at least 3 atoms in the main chain and being optionally substituted with one or more substituents selected from epoxy, fluoro and hydroxy;   R 4  is an isopropyl group   A and B are each individually hydrogen atoms or ethyl groups, or   A and B form together a methylene group in a quantity effective for the intended purpose.   
     
     
       11. A method of claim 5 wherein the active ingredient is of the formula ##STR31## 
     
     
       12. A method of claim 6 wherein the active ingredient is of the formula