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US4185101A
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1,3,5(10),6,8-19-Nor-pregnapentaenes, their use as anti-psoriatic agents, and pharmaceutical formulations useful therefor
Assignee: Merck Sharp & Dohme LLC
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Filing: 1978-07-18
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Granted: 1980-01-22
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Expires: 1998-07-18
Abstract
Abstract 1,3,5(10),6,8-19-Nor-pregnapentaene-20-ones exhibit anti-mitotic activity with minimal or no hormonal activity. They are particularly useful in the treatment and control of psoriasis when applied topically, preferred anti-psoriatic compounds being 1,3,5(10),6,8-19-nor-pregnapentaene-3,17 alpha ,21-triol-20-one 21-acetate and the 16 alpha -methyl and 16 beta -methyl analogs thereof. The 1,3,5(10),6,8-19-nor-pregnapentaene-20-ones are also useful as intermediates in the preparation of the corresponding 14-dehydro compounds which also exhibit anti-mitotic activity as described and claimed in copending application Ser. No. 819,182 filed July 26, 1977 of Richard W. Draper and Charles J. Casmer of common assignee as this application, and now abandoned.
Inventors
- 👤 Richard W. Draper
- 👤 Michael J. Green
- 👤 Charles J. Casmer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 19:19
CPC Classifications
C; C07; C07J; C07J5/00; C07J5/0046; C07J5/0061; C07J5/0069; C07J5/0076; C07J21/00; C07J5/0053; C07J5/0092; C07J71/00; C07J71/0005; C07J71/0026; C07J71/0031
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
214 words
The method of eliciting a mitotic inhibitory response in a warm-blooded animal having a disease characterized by rapid cell proliferation which comprises administering to said animal a non-toxic, mitotic inhibitory effective amount of a 19-nor-pregnapentaene-20-one of the following formula I: ##STR4## wherein A is hydrogen, lower alkyl, fluoro, fluoromethyl, difluoromethyl, or trifluoromethyl; R is hydrogen, lower alkyl, or an acyl radical of a hydrocarboncarboxylic acid having up to 20 carbon atoms; Y is (H,H), (H,OH), or oxygen, W is (H,H); (H, lower alkyl); CHα -hydroxy); (H,α-OR 1 ), wherein R 1 is an acyl radical of a hydrocarboncarboxylic acid having up to 20 carbon atoms; or ═CHT wherein T is hydrogen, lower alkyl, fluorine, or chlorine; Q is OR 2 wherein R 2 is hydrogen or an acyl radical of a hydrocarboncarboxylic acid having up to 20 carbon atoms; hydrogen provided W is (H,H), or (H, lower alkyl); or Q and W together is a ≠α,17α-lower alkylidenedioxy; R 3 is hydrogen or an acyl radical of a hydrocarboncarboxylic acid having up to 20 carbon atoms; or OR 3 together with Q is a member selected from the group consisting of alkylidenedioxy and alkylorthoalkanoate; and when Q is hydroxy and R 3 is hydrogen, the 17α,20;20,21-bismethylenedioxy derivatives thereof; together with a non-toxic pharmaceutically acceptable carrier.
Claim 2
Independent Claim
214 words
The method of eliciting a mitotic inhibitory response in a warm-blooded animal having a disease characterized by rapid cell proliferation which comprises administering to said animal a non-toxic, mitotic inhibitory effective amount of a 19-nor-pregnapentaene-20-one of the following formula I: ##STR4## wherein A is hydrogen, lower alkyl, fluoro, fluoromethyl, difluoromethyl, or trifluoromethyl; R is hydrogen, lower alkyl, or an acyl radical of a hydrocarboncarboxylic acid having up to 20 carbon atoms; Y is (H,H), (H,OH), or oxygen, W is (H,H); (H, lower alkyl); CHα -hydroxy); (H,α-OR 1 ), wherein R 1 is an acyl radical of a hydrocarboncarboxylic acid having up to 20 carbon atoms; or ═CHT wherein T is hydrogen, lower alkyl, fluorine, or chlorine; Q is OR 2 wherein R 2 is hydrogen or an acyl radical of a hydrocarboncarboxylic acid having up to 20 carbon atoms; hydrogen provided W is (H,H), or (H, lower alkyl); or Q and W together is a ≠α,17α-lower alkylidenedioxy; R 3 is hydrogen or an acyl radical of a hydrocarboncarboxylic acid having up to 20 carbon atoms; or OR 3 together with Q is a member selected from the group consisting of alkylidenedioxy and alkylorthoalkanoate; and when Q is hydroxy and R 3 is hydrogen, the 17α,20;20,21-bismethylenedioxy derivatives thereof; together with a non-toxic pharmaceutically acceptable carrier.
Claim 3
Dependent Claim
17 words
The method of claim 1 wherein said disease is a skin disease characterized by rapid cell proliferation.
Claim 4
Dependent Claim
63 words
The method of claim 2 when said 19-nor-pregnapentaene-20-one is administered topically, which is the method of reducing epidermal mitosis in a warm-blooded animal having a skin disease characterized by rapid cell proliferation which comprises applying topically to the affected area in a concentration effective for reducing epidermal mitosis, a 19-nor-pregnapentaene-20-one of formula I in claim 1, together with a non-toxic, pharmaceutically acceptable carrier.
Claim 5
Dependent Claim
52 words
The method of claim 3 wherein said skin disease is psoriasis, which is the method of treating and controlling psoriasis which comprises applying topically to the affected area in a concentration effective for the treatment of psoriasis, a 19-nor-pregnapentaene-20-one of formula I in claim 1, together with a non-toxic, pharmaceutically acceptable carrier.
Claim 6
Dependent Claim
22 words
The method of claim 4, when carried out with a 1,3,5(10),6,8-19-nor-pregnapentaene-20-one of formula I wherein W is (H, lower alkyl) or (H,H).
Claim 7
Dependent Claim
71 words
The method of claim 5 when carried out with a compound of structural formula II: ##STR5## wherein R is hydrogen, lower alkyl, or an acyl radical of a hydrocarboncarboxylic acid having up to 20 carbon atoms; R 2 and R 3 are each hydrogen or an acyl radical of a hydrocarboncarboxylic acid having up to 20 carbon atoms; Y is (H, OH) or oxygen; and W is (H,H) or (H, methyl).
Claim 8
Dependent Claim
21 words
The method of claim 6 when carried out with 1,3,5(10),6,8-19-nor-prognapentaene-3,17α,21-triol-11,20-dione or with the 21-acetate thereof or their 16α-methyl or 16β-methyl homologs.
Claim 9
Dependent Claim
30 words
A topical pharmaceutical composition for the treatment of psoriasis comprising an anti-psoriatically effective amount of a 19-nor-pregnapentaene-20-one of formula I in claim 1, together with a non-toxic, pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
19 words
A topical pharmaceutical composition of claim 8 wherein said 19-nor-pregnapentaene-20-one is a 19-nor-pregnapentaene-20-one of formula II in claim 6.
Claim 11
Dependent Claim
33 words
The topical pharmaceutical composition of claim 9 comprising an anti-psoriatic effective amount of 1,3,5(10),6,8-19-nor-pregnapentaene-3,17α,21-triol-11,20-dione or of the 21-acetate thereof or of their 16β-methyl or 16α-methyl homologs, together with a non-toxic, pharmaceutically acceptable carrier.
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) | 1983-01-21 | 1983-07-23 | 1984-01-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-01-21 | 1987-07-23 | 1988-01-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-01-21 | 1991-07-23 | 1992-01-22 | $7700.00 | Window Closed / Lapsed |