US4242334A
Expired / Lapsed
US
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Corticoid 17-(alkyl carbonates) and processes for their preparation
Assignee: Sanofi Aventis Deutschland GmbH
•
Filing: 1978-08-02
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Granted: 1980-12-30
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Expires: 1998-08-02
Abstract
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.
Inventors
- 👤 Ulrich Stache
- 👤 Werner Fritsch
- 👤 Hans G. Alpermann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 19:14
CPC Classifications
C; C07; C07J; C07J5/00; C07J5/0046; C07J5/0061; C07J5/0069; C07J5/0076; A; A61; A61P; A61P17/00; A61P29/00; C07J21/00; C07J31/00; C07J31/006; C07J43/00; C07J43/003; C07J5/0053; C07J71/00; C07J71/0036; C07J71/0042; C07J71/0047
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
153 words
A compound selected from the group consisting of compounds of the formula ##STR17## wherein A is ##STR18## or C═O, and compounds of the formula ##STR19## wherein Y is hydrogen, fluorine, or chlorine; Z is hydrogen, chlorine, fluorine, or methyl; R 3 is hydrogen, fluorine, α-methyl, monofluoromethyl, or difluoromethyl; R 2 is alkyl having 1 to 8 carbon atoms; and R 1 is acyl of the formula ##STR20## wherein R 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 1 is carbonyloxyalkyl of the formula ##STR21## wherein n is 0 or 1 and R 4 is as earlier defined except that R 4 is other than hydrogen when n is 0, or R 1 is ##STR22## wherein R 5 is alkyl having 1 to 4 carbon atoms, phenyl, methylphenyl, ethylphenyl, fluorophenyl, bromophenyl, or chlorophenyl.
Claim 2
Dependent Claim
153 words
A compound selected from the group consisting of compounds of the formula ##STR17## wherein A is ##STR18## or C═O, and compounds of the formula ##STR19## wherein Y is hydrogen, fluorine, or chlorine; Z is hydrogen, chlorine, fluorine, or methyl; R 3 is hydrogen, fluorine, α-methyl, monofluoromethyl, or difluoromethyl; R 2 is alkyl having 1 to 8 carbon atoms; and R 1 is acyl of the formula ##STR20## wherein R 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 1 is carbonyloxyalkyl of the formula ##STR21## wherein n is 0 or 1 and R 4 is as earlier defined except that R 4 is other than hydrogen when n is 0, or R 1 is ##STR22## wherein R 5 is alkyl having 1 to 4 carbon atoms, phenyl, methylphenyl, ethylphenyl, fluorophenyl, bromophenyl, or chlorophenyl.
Claim 3
Dependent Claim
16 words
A compound as in claim 1 wherein R 1 is ##STR23## and R 4 is hydrogen.
Claim 4
Dependent Claim
22 words
A compound as in claim 1 wherein R 1 is ##STR24## and R 4 is alkyl having 1 to 10 carbon atoms.
Claim 5
Dependent Claim
10 words
A compound as in claim 1 of the formula ##STR25##
Claim 6
Dependent Claim
10 words
A compound as in claim 1 of the formula ##STR26##
Claim 7
Dependent Claim
10 words
A compound as in claim 1 of the formula ##STR27##
Claim 8
Dependent Claim
9 words
A compound as in claim 1 which is prednisolon-17-ethyl-carbonate-21-propionate.
Claim 9
Dependent Claim
9 words
A compound as in claim 1 which is prednisolon-17-ethyl-carbonate-21-acetate.
Claim 10
Dependent Claim
9 words
A compound as in claim 1 which is prednisolon-17-n-propyl-carbonate-21-propionate.
Claim 11
Dependent Claim
9 words
A compound as in claim 1 which is prednisolon-17-n-propyl-carbonate-21-acetate.
Claim 12
Dependent Claim
9 words
A compound as in claim 1 which is cortisol-17-ethyl-carbonate-21-propionate.
Claim 13
Dependent Claim
9 words
A compound as in claim 2 which is cortisol-17-n-propyl-carbonate-21-propionate.
Claim 14
Dependent Claim
26 words
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.
Claim 15
Dependent Claim
30 words
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.
Claim 16
Independent Claim
140 words
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═O; Y is hydrogen, fluorine, or methyl; Z is hydrogen, chlorine, fluorine, or methyl R 3 is hydrogen, fluorine, α-methyl, monofluoromethyl, or difluoromethyl; R 2 is alkyl having 1 to 8 carbon atoms; and R 1 is acyl of the formula ##STR30## wherein R 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##
Claim 17
Independent Claim
140 words
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═O; Y is hydrogen, fluorine, or methyl; Z is hydrogen, chlorine, fluorine, or methyl R 3 is hydrogen, fluorine, α-methyl, monofluoromethyl, or difluoromethyl; R 2 is alkyl having 1 to 8 carbon atoms; and R 1 is acyl of the formula ##STR30## wherein R 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##
Claim 18
Dependent Claim
22 words
A method as in claim 15 wherein A is ##STR33## and the hydroxy group thereof is then oxidized to a keto group.
Claim 19
Independent Claim
144 words
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═O; Y is hydrogen, fluorine, or methyl; Z is hydrogen, chlorine, fluorine, or methyl R 3 is hydrogen, fluorine, α-methyl, monofluoromethyl, or difluoromethyl; R 2 is alkyl having 1 to 8 carbon atoms; and R 1 is carbonyloxyalkyl of the formula ##STR36## wherein n is 0 or 1 and R 4 is hydrogen, alkyl having 1 to 10 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms except that R 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##
Claim 20
Independent Claim
144 words
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═O; Y is hydrogen, fluorine, or methyl; Z is hydrogen, chlorine, fluorine, or methyl R 3 is hydrogen, fluorine, α-methyl, monofluoromethyl, or difluoromethyl; R 2 is alkyl having 1 to 8 carbon atoms; and R 1 is carbonyloxyalkyl of the formula ##STR36## wherein n is 0 or 1 and R 4 is hydrogen, alkyl having 1 to 10 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms except that R 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##
Claim 21
Dependent Claim
22 words
A method as in claim 17 wherein A is ##STR39## and the hydroxy group thereof is then oxidized to a keto group.
Claim 22
Independent Claim
120 words
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═O; Y is hydrogen, fluorine, or methyl; Z is hydrogen, chlorine, fluorine, or methyl R 3 is hydrogen, fluorine, α-methyl, monofluoromethyl; or difluoromethyl; R 2 is alkyl having 1 to 8 carbon atoms; and R 1 is ##STR42## wherein R 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##
Claim 23
Independent Claim
120 words
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═O; Y is hydrogen, fluorine, or methyl; Z is hydrogen, chlorine, fluorine, or methyl R 3 is hydrogen, fluorine, α-methyl, monofluoromethyl; or difluoromethyl; R 2 is alkyl having 1 to 8 carbon atoms; and R 1 is ##STR42## wherein R 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##
Claim 24
Dependent Claim
22 words
A method as in claim 19 wherein A is ##STR45## and the hydroxy group thereof is then oxidized to a keto group.
Claim 25
Dependent Claim
15 words
A compound as in claim 1 wherein R 1 is carbonyloxyalkyl of the formula ##STR46##
Claim 26
Dependent Claim
11 words
A compound as in claim 1 wherein R 1 is ##STR47##
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-12-30 | 1984-06-30 | 1984-12-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-30 | 1988-06-30 | 1988-12-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-30 | 1992-06-30 | 1992-12-30 | $7700.00 | Window Closed / Lapsed |