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Claims for Patent: 4,242,334

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Claims for Patent: 4,242,334

Title: Corticoid 17-(alkyl carbonates) and processes for their preparation
Abstract:What is disclosed is corticoid 17-(alkyl carbonates) of the formula ##STR1## as defined in the specification, which compounds can be used in veterinary therapy and human therapy, in the form of suspensions, ointments, creams, sprays and the like, for the treatment of inflammatory dermatoses of very diverse cause.
Inventor(s): Stache; Ulrich (Hofheim am Taunus, DE), Fritsch; Werner (Bad Soden am Taunus, DE), Alpermann; Hans G. (Konigstein all of, DE)
Assignee: Hoechst Aktiengesellschaft (Frankfurt am Main, DE)
Application Number:05/930,194
Patent Claims: 1. A compound selected from the group consisting of compounds of the formula ##STR17## wherein A is ##STR18## or C.dbd.O, and compounds of the formula ##STR19## wherein Y is hydrogen, fluorine, or chlorine;

Z is hydrogen, chlorine, fluorine, or methyl;

R.sub.3 is hydrogen, fluorine, .alpha.-methyl, monofluoromethyl, or difluoromethyl;

R.sub.2 is alkyl having 1 to 8 carbon atoms; and

R.sub.1 is acyl of the formula ##STR20## wherein R.sub.4 is hydrogen, alkyl having 1 to 10 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms and n is a number from 0 to 4, or

R.sub.1 is carbonyloxyalkyl of the formula ##STR21## wherein n is 0 or 1 and R.sub.4 is as earlier defined except that R.sub.4 is other than hydrogen when n is 0, or R.sub.1 is ##STR22## wherein R.sub.5 is alkyl having 1 to 4 carbon atoms, phenyl, methylphenyl, ethylphenyl, fluorophenyl, bromophenyl, or chlorophenyl.

2. A compound as in claim 1 wherein R.sub.1 is ##STR23## and R.sub.4 is hydrogen.

3. A compound as in claim 1 wherein R.sub.1 is ##STR24## and R.sub.4 is alkyl having 1 to 10 carbon atoms.

4. A compound as in claim 1 of the formula ##STR25##

5. A compound as in claim 1 of the formula ##STR26##

6. A compound as in claim 1 of the formula ##STR27##

7. A compound as in claim 1 which is prednisolon-17-ethyl-carbonate-21-propionate.

8. A compound as in claim 1 which is prednisolon-17-ethyl-carbonate-21-acetate.

9. A compound as in claim 1 which is prednisolon-17-n-propyl-carbonate-21-propionate.

10. A compound as in claim 1 which is prednisolon-17-n-propyl-carbonate-21-acetate.

11. A compound as in claim 1 which is cortisol-17-ethyl-carbonate-21-propionate.

12. A compound as in claim 2 which is cortisol-17-n-propyl-carbonate-21-propionate.

13. A pharmaceutical composition for the treatment of inflammatory dermatosis which comprises an effective amount of a compound as in claim 1 and a pharmaceutically-acceptable carrier therefor.

14. The method of treating inflammatory dermatosis in a human or animal suffering therefrom which method comprises locally or topically administering an effective amount of a compound as in claim 1.

15. A method for making a compound selected from the group consisting of compounds of the formula ##STR28## and compounds of the formula ##STR29## or C.dbd.O; Y is hydrogen, fluorine, or methyl;

Z is hydrogen, chlorine, fluorine, or methyl

R.sub.3 is hydrogen, fluorine, .alpha.-methyl, monofluoromethyl, or difluoromethyl;

R.sub.2 is alkyl having 1 to 8 carbon atoms; and

R.sub.1 is acyl of the formula ##STR30## wherein R.sub.4 is hydrogen, alkyl having 1 to 10 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms and n is a number from 0 to 4, which method comprises hydrolyzing with weak acid a corticosteroid 17, 21-(dialkyl-orthocarbonate) of the formula ##STR31## respectively, to form the corresponding 17-(monoalkyl carbonate)-21-hydroxy compound, and then esterifying the 21-hydroxy group by reaction thereof with a halide or anhydride of a carboxylic acid of the formula ##STR32##

16. A method as in claim 15 wherein A is ##STR33## and the hydroxy group thereof is then oxidized to a keto group.

17. A method for making a compound selected from the group consisting of the compounds of the formula ##STR34## and compounds of the formula ##STR35## or C.dbd.O; Y is hydrogen, fluorine, or methyl;

Z is hydrogen, chlorine, fluorine, or methyl

R.sub.3 is hydrogen, fluorine, .alpha.-methyl, monofluoromethyl, or difluoromethyl;

R.sub.2 is alkyl having 1 to 8 carbon atoms; and

R.sub.1 is carbonyloxyalkyl of the formula ##STR36## wherein n is 0 or 1 and R.sub.4 is hydrogen, alkyl having 1 to 10 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms except that R.sub.4 is other than hydrogen if n is 0, which method comprises hydrolyzing with weak acid a corticosteroid 17, 21-(dialkylorthocarbonate) of the formula ##STR37## respectively, to form the corresponding 17-(monoalkyl carbonate)-21-hydroxy compound, and then esterifying the 21-hydroxy group by reaction thereof with a halogenoformate of the formula ##STR38##

18. A method as in claim 17 wherein A is ##STR39## and the hydroxy group thereof is then oxidized to a keto group.

19. A method for making a compound selected from the group consisting of compounds of the formula ##STR40## and compounds of the formula ##STR41## or C.dbd.O; Y is hydrogen, fluorine, or methyl;

Z is hydrogen, chlorine, fluorine, or methyl

R.sub.3 is hydrogen, fluorine, .alpha.-methyl, monofluoromethyl; or difluoromethyl;

R.sub.2 is alkyl having 1 to 8 carbon atoms; and R.sub.1 is ##STR42## wherein R.sub.5 is alkyl having 1 to 4 carbon atoms, phenyl, methylphenyl, ethylphenyl, fluorophenyl, bromophenyl, or chlorophenyl, which method comprises hydrolyzing with weak acid a corticosteroid 17,21-(dialkyl-orthocarbonate) of the formula ##STR43## respectively, to form the corresponding 17-(monoalkyl carbonate)-21-hydroxy compound, and then esterifying the 21-hydroxy group by reaction thereof with a sulfonic acid halide of the formula ##STR44##

20. A method as in claim 19 wherein A is ##STR45## and the hydroxy group thereof is then oxidized to a keto group.

21. A compound as in claim 1 wherein R.sub.1 is carbonyloxyalkyl of the formula ##STR46##

22. A compound as in claim 1 wherein R.sub.1 is ##STR47##
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