US4285937A
Expired / Lapsed
US
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Novel androstadiene-17-carboxylic acid esters
Assignee: Novartis Corp
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Filing: 1979-10-30
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Granted: 1981-08-25
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Expires: 1999-10-30
Abstract
Abstract The invention provides novel esters of androstadiene 17-carboxyclic acids of the formula ##STR1## wherein R' represents a hydroxyl group which is esterified with a carboxyclic acid having not more than 7 carbon atoms, R" represents a methyl group in the α- or β-position or the methylene group, wherein R is H or Cl, each of X and Y represents a hydrogen, chlorine or fluorine atom, with the proviso that at least one of these substituents is one of these halogens, when R is Cl, and that Y is only Cl or F and X only Cl, when R is H and that the androstadiene-17-carboxylic acid ester group does not contain more than 11 carbon atoms. The new esters have pronounced antiinflammatory action coupled with remarkably low systemic side effects on thymus, adrenals and body weight. They are especially suitable to be used in dermatology.
Inventors
- 👤 Jaroslav Kalvoda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 11:47
CPC Classifications
C; C07; C07J; C07J3/00; C07J3/005; A; A61; A61P; A61P29/00
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
96 words
Esters of androstadiene-17-carboxylic acids of the formula ##STR5## wherein R' represents a hydroxyl group which is esterified with a lower aliphatic carboxylic acid having not more than 7 carbon atoms, R" represents a methyl group in the alpha- or beta-position or the methylene group, R is H or Cl, and Y represents a hydrogen, chlorine or fluorine atom, with the proviso that Y is only Cl or F, when R is H and that the androstadiene-17-carboxylic acid ester group is derived from an aliphatic alcohol, so that said group contains not more than 6 carbon atoms.
Claim 2
Dependent Claim
96 words
Esters of androstadiene-17-carboxylic acids of the formula ##STR5## wherein R' represents a hydroxyl group which is esterified with a lower aliphatic carboxylic acid having not more than 7 carbon atoms, R" represents a methyl group in the alpha- or beta-position or the methylene group, R is H or Cl, and Y represents a hydrogen, chlorine or fluorine atom, with the proviso that Y is only Cl or F, when R is H and that the androstadiene-17-carboxylic acid ester group is derived from an aliphatic alcohol, so that said group contains not more than 6 carbon atoms.
Claim 3
Dependent Claim
29 words
Compounds according to claim 1, wherein the esters of the steroid-17-carboxylic acids are derived from said aliphatic alcohols which are unsubstituted or substituted by hydroxyl, lower alkoxy or acyloxy.
Claim 4
Dependent Claim
24 words
Compounds according to claim 1, wherein the esters of the steroid-17-carboxylic acids are derived from lower aliphatic alcohols having 1 to 5 carbon atoms.
Claim 5
Dependent Claim
19 words
Compounds according to claim 1, wherein the esters of the steroid-17-carboxylic acids are derived from dihydric or trihydric alcohols.
Claim 6
Dependent Claim
23 words
Compounds according to claim 1, wherein an esterified hydroxyl group R' is the formyloxy, acetoxy, propionyloxy, butyryloxy, valeryloxy, diethylacetoxy or the caproyloxy group.
Claim 7
Dependent Claim
11 words
A compound according to claim 1, which is the methyl 2,9α-dichloro-6α-fluoro-11β-hydroxy-16α-methyl-3,20-dioxo-17α-propionyloxy-androsta-1,4-diene-17-carboxylate.
Claim 8
Dependent Claim
3 words
The methyl 9alpha-chloro-6alpha-fluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-propionyloxy-androsta-1,4-diene-17-carboxylate.
Claim 9
Dependent Claim
3 words
The methyl 9alpha-chloro-6alpha-fluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-propionyloxy-androsta-1,4-diene-17-carboxylate.
Claim 10
Dependent Claim
3 words
The methyl 2-chloro-9alpha-fluoro-11beta-hydroxy-17alpha-propionyloxy-16beta-methyl-3-oxo-androsta-1,4-diene-17-carboxylate.
Claim 11
Dependent Claim
3 words
The methyl 2-chloro-9alpha-fluoro-11beta-hydroxy-17alpha-propionyloxy-16beta-methyl-3-oxo-androsta-1,4-diene-17-carboxylate.
Claim 12
Dependent Claim
11 words
A compound according to claim 1, which is the chloromethyl 2,9α-dichloro-6α-fluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxy-17-androsta-1,4-diene-17β-carboxylate.
Claim 13
Dependent Claim
22 words
An antiinflammatory pharmaceutical preparation which contains an antiinflammatory effective amount of a compound according to claim 1, together with a pharmaceutical carrier.
Claim 14
Dependent Claim
75 words
Androstadiene-17-carboxylic acids of the formula ##STR6## wherein R' represents a free hydroxyl group or a hydroxyl group which is esterified with a lower aliphatic carboxylic acid having not more than 7 carbon atoms, R" represents a methyl group in the alpha- or beta-position or the methylene group, R is H or Cl, and Y represents a hydrogen, chlorine or fluorine atom, with the proviso that Y is only Cl or F, when R is H.
Claim 15
Dependent Claim
75 words
Androstadiene-17-carboxylic acids of the formula ##STR6## wherein R' represents a free hydroxyl group or a hydroxyl group which is esterified with a lower aliphatic carboxylic acid having not more than 7 carbon atoms, R" represents a methyl group in the alpha- or beta-position or the methylene group, R is H or Cl, and Y represents a hydrogen, chlorine or fluorine atom, with the proviso that Y is only Cl or F, when R is H.
Claim 16
Dependent Claim
9 words
Compounds according to claim 1, wherein Y represents fluorine.
Claim 17
Dependent Claim
9 words
Compounds according to claim 1, wherein R represents hydrogen.
Claim 18
Dependent Claim
17 words
Compounds according to claim 11, wherein R is hydrogen, Y is fluorine and R' is lower alkanoyloxy.
Claim 19
Dependent Claim
69 words
Esters of androstadiene-17-carboxylic acids of the formula ##STR7## wherein R is hydrogen or chlorine, R 1 is the acyl radical of a lower aliphatic carboxylic acid having not more than 7 carbon atoms and R 2 is the moiety of an aliphatic alcohol with not more than 10 carbon atoms, which is unsubstituted or substituted by halogen, hydroxy, lower alkoxy or acyloxy containing said acyl radical R 1 .
Claim 20
Dependent Claim
69 words
Esters of androstadiene-17-carboxylic acids of the formula ##STR7## wherein R is hydrogen or chlorine, R 1 is the acyl radical of a lower aliphatic carboxylic acid having not more than 7 carbon atoms and R 2 is the moiety of an aliphatic alcohol with not more than 10 carbon atoms, which is unsubstituted or substituted by halogen, hydroxy, lower alkoxy or acyloxy containing said acyl radical R 1 .
Claim 21
Dependent Claim
20 words
Compounds according to claim 15, wherein R is hydrogen, R 1 is lower alkanoyl and R 2 is lower alkyl.
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) | 1984-08-24 | 1985-02-23 | 1985-08-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-24 | 1989-02-23 | 1989-08-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-24 | 1993-02-23 | 1993-08-25 | $7700.00 | Window Closed / Lapsed |