US4404200A
Expired / Lapsed
US
⏱️ 0.0 years remaining
4-Pregnene-derivatives, a process for their preparation, composition and method for the treatment of inflammatory conditions
Assignee: Draco AB
•
Filing: 1981-11-17
•
Granted: 1983-09-13
•
Expires: 2001-11-17
Abstract
Abstract The invention refers to compounds having anti-inflammatory activity, characterized by the formula ##STR1## in the form of a stereoisomeric mixture or an epimer of the R or S type regarding the orientation of the substituents at the carbon atom in position 22, in which formula A is n-propyl or n-butyl and Z is hydroxyl or hydroxyl esterified with a fatty acid with a straight or branched hydrocarbon chain having 1-5 carbon atoms. The invention also refers to a process for the preparation of these compounds, a pharmaceutical preparation containing one of the compounds and a method for the treatment and control of inflammatory conditions.
Inventors
- 👤 Bror A. Thalen
- 👤 Ralph L. Brattsand
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 19:13
CPC Classifications
C; C07; C07J; C07J5/00; C07J71/00; C07J71/0005; C07J71/0026; C07J71/0031; A; A61; A61P; A61P29/00
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
65 words
A compound of the formula ##STR10## in the form of a stereoisomeric mixture or an epimer of the R or S type regarding the orientation of the substituents in the carbon atom at position 22, in which formula A is n-propyl or n-butyl and Z is hydroxyl or hydroxyl esterified with a fatty acid with a straight or branched hydrocarbon chain having 1-5 carbon atoms.
Claim 2
Dependent Claim
65 words
A compound of the formula ##STR10## in the form of a stereoisomeric mixture or an epimer of the R or S type regarding the orientation of the substituents in the carbon atom at position 22, in which formula A is n-propyl or n-butyl and Z is hydroxyl or hydroxyl esterified with a fatty acid with a straight or branched hydrocarbon chain having 1-5 carbon atoms.
Claim 3
Dependent Claim
16 words
A steroid according to claim 1 wherein Z is hydroxyl and A is n-propyl or n-butyl.
Claim 4
Dependent Claim
10 words
A steroid according to claim 2 wherein A is n-propyl.
Claim 5
Dependent Claim
12 words
A steroid according to claim 3 in the form of the R-epimer.
Claim 6
Dependent Claim
10 words
A steroid according to claim 2 wherein A is n-butyl.
Claim 7
Dependent Claim
12 words
A steroid according to claim 5 in the form of the R-epimer.
Claim 8
Dependent Claim
28 words
A steroid according to claim 1 wherein Z is hydroxyl esterified with a straight or branched hydrocarbon chain having 1-5 carbon atoms and A is n-propyl or n-butyl.
Claim 9
Dependent Claim
10 words
A steroid according to claim 7 wherein A is n-propyl.
Claim 10
Dependent Claim
14 words
A steroid according to claim 8 wherein Z is hydroxyl esterified with acetic acid.
Claim 11
Dependent Claim
12 words
A steroid according to claim 9 in the form of the R-epimer.
Claim 12
Dependent Claim
14 words
A steroid according to claim 8 wherein Z is hydroxyl esterified with butyric acid.
Claim 13
Dependent Claim
14 words
A steroid according to claim 8 wherein Z is hydroxyl esterified with trimethylacetic acid.
Claim 14
Dependent Claim
10 words
A steroid according to claim 7 wherein A is n-butyl.
Claim 15
Dependent Claim
14 words
A steroid according to claim 13 wherein Z is hydroxyl esterified with acetic acid.
Claim 16
Dependent Claim
12 words
A steroid according to claim 14 in the form of the R-epimer.
Claim 17
Dependent Claim
176 words
A process for the preparation of a compound of the formula ##STR11## in the form of a stereoisomeric mixture or an epimer of the R or S type regarding the orientation of the substituents at the carbon atom in position 22, in which formula A is n-propyl or n-butyl and Z is hydroxyl, or hydroxyl esterified with a fatty acid with a straight or branched hydrocarbon chain having 1-5 carbon atoms, characterized by reacting 16α-hydroxycortisol of the formula ##STR12## with an aldehyde of the formula A-CHO or its acetals ##STR13## wherein A is defined as above and B 1 -B 6 are the same or different and each representing hydrogen or an alkyl group with straight or branched hydrocarbon chains having 1-10 carbon atoms, whereafter if an 21-ester is desired Z is esterified with a fatty acid with a straight or branched hydrocarbon chain having 1-5 carbon atoms, and if an R epimer is desired submitting the obtained compound, before or after esterification to chromatography on a cross-linked dextran gel with an organic solvent as eluant.
Claim 18
Dependent Claim
176 words
A process for the preparation of a compound of the formula ##STR11## in the form of a stereoisomeric mixture or an epimer of the R or S type regarding the orientation of the substituents at the carbon atom in position 22, in which formula A is n-propyl or n-butyl and Z is hydroxyl, or hydroxyl esterified with a fatty acid with a straight or branched hydrocarbon chain having 1-5 carbon atoms, characterized by reacting 16α-hydroxycortisol of the formula ##STR12## with an aldehyde of the formula A-CHO or its acetals ##STR13## wherein A is defined as above and B 1 -B 6 are the same or different and each representing hydrogen or an alkyl group with straight or branched hydrocarbon chains having 1-10 carbon atoms, whereafter if an 21-ester is desired Z is esterified with a fatty acid with a straight or branched hydrocarbon chain having 1-5 carbon atoms, and if an R epimer is desired submitting the obtained compound, before or after esterification to chromatography on a cross-linked dextran gel with an organic solvent as eluant.
Claim 19
Dependent Claim
19 words
A process according to claim 16 characterized in that a compound according to any of claims 2-15 is prepared.
Claim 20
Dependent Claim
72 words
A process according to claim 16 wherein the resolution of the stereoisomeric mixture into epimers of the R and S type regarding the orientation of the substituents at the carbon atom in position 22 is characterized by carrying out the chromatography on a bead-formed hydroxypropylated dextran gel wherein the dextran chains are cross-linked to give a three-dimensional polysaccharide network and using as eluting agent a mixture of n-heptane-chloroform-ethanol in the proportions 0-50:50-100:10-1.
Claim 21
Dependent Claim
15 words
A pharmaceutical preparation comprising as active ingredient a compound according to any of claims 1-15.
Claim 22
Dependent Claim
11 words
A pharmaceutical preparation according to claim 19 in dosage unit form.
Claim 23
Dependent Claim
18 words
A pharmaceutical preparation according to claims 19-20 comprising the active ingredient in association with a pharmaceutically acceptable carrier.
Claim 24
Independent Claim
39 words
A method for the treatment and control of inflammatory conditions in mammals, including man, characterized by the administration to a host in need of such treatment of an effective amount of a compound according to any of claims 1-15.
References Cited (Backward Citations)
GB909126A
Cited
US2990401A
Cited
US3048581A
Cited
US3549498A
Cited
DE2016353A1
Cited
SE378110B
Cited
US3928326A
Cited
US3996359A
Cited
ES487089A0
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-09-12 | 1987-03-14 | 1987-09-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-09-12 | 1991-03-14 | 1991-09-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-09-12 | 1995-03-14 | 1995-09-13 | $7700.00 | Window Closed / Lapsed |