US3689512A
Expired / Lapsed
US
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Novel 3-etherified-1,3,5(10)-triene-steroids and process thereof
Assignee: Wyeth LLC
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Filing: 1970-10-06
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Granted: 1972-09-05
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Expires: 1990-10-06
Abstract
Abstract Disclosed are new and novel 3-cyclobutyloxy, 3cyclopropylmethoxy and 3-cyclobutylmethoxy-1,3,5(10)-triensteroids and a method for the production thereof by reacting the corresponding 3-hydroxy steroids with a (lower)alkoxide in a (lower)alkanol followed by an appropriate tosylate or halade of cyclopropylmethyl, cyclobutyl and cyclobutylmethyl. The new and novel compounds are useful for depressing lipid levels in animals.
Inventors
- 👤 Harshavadan C Shah
- 👤 George C Buzby Jr
- 👤 Herchel Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 05:10
CPC Classifications
C; C07; C07J; C07J21/00; C07J1/00; C07J5/00; C07J75/00
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
10 words
A compound as described in claim 1, which is: d-3-(cyclobutylmethyloxy)estra-1,3,5(10)-trien-17-one.
Claim 2
Dependent Claim
12 words
A compound as described in claim 1, which is: d-3-(cyclobutylmethyloxy)-19-nor-17 Alpha -pregna-1,3,5(10)-trien-20-yn-17-ol.
Claim 3
Dependent Claim
10 words
A compound as described in claim 1, which is: dl-13-ethyl-3-(cyclobutylmethoxy)gona-1,3,5(10)-trien-17-one.
Claim 4
Dependent Claim
12 words
A compound as described in claim 1, which is: dl-13-ethyl-3-(cyclobutylmethoxy)-18,19-dinor-17 Alpha -pregna-1,3,5(10)-trien-20-yn-17-ol.
Claim 5
Dependent Claim
10 words
A compound as described in claim 1, which is: d-3-(cyclopropylmethoxy)estra-1,3,5(10)-trien-17-one.
Claim 6
Dependent Claim
12 words
A compound as described in claim 1, which is: d-3-(cyclopropylmethoxy)-19-nor-17 Alpha -pregna-1,3,5(10)-trien-20-yn-17-ol.
Claim 7
Dependent Claim
12 words
A compound as described in claim 1, which is: dl-13-ethyl-3-(cyclobutylmethoxy)gona-1,3,5(10)-trien-17 Beta -ol.
Claim 8
Dependent Claim
12 words
A compound as described in claim 1, which is: d-3-(cyclobutylmethoxy)estra-1,3,5(10)-trien-17 Beta -ol.
Claim 9
Dependent Claim
12 words
A process for the preparation of a 3-substituted-13-(lower)alkylgona-(and 8-isogona)-1,3,5(10)-trien-17-one of the formula:
Claim 10
Dependent Claim
24 words
A process as defined in claim 10 wherein, in Step (a), said alkali metal (lower)alkoxide is sodium methoxide and said (lower)alkanol medium is methanol.
Claim 11
Dependent Claim
18 words
A process as defined in claim 10 wherein, in Step (b), said inert organic solvent medium is dimethyLsulfoxide.
Claim 12
Dependent Claim
36 words
A process as defined in claim 10 wherein Step (c) is carried out at a temperature of from about 20*C. to about 100* C. for a period of from about 2 hours to about 48 hours.
Claim 13
Dependent Claim
15 words
A process as defined in claim 10 wherein, in Step (c), said halide is bromide.
Claim 14
Dependent Claim
56 words
A process as defined in claim 10 wherein d-3-(cyclobutyloxy)estra-1,3,5(10)-trien-17-one is prepared by the steps of: a. reacting d-estrone with sodium methoxide in methanol; b. removing the methanol by vacuum distillation and adding dimethylsulfoxide; c. reacting the mixture of Step (b) with cyclobutylbromide; and d. recovering the product by removing the solvent by distillation in a vacuum.
Claim 15
Dependent Claim
64 words
A process as defined in claim 10 wherein d-3-(cyclobutylmethyleneoxy)estra-1,3,5(10)-trien-17-one is prepared by the steps of: a. reacting d-estrone with sodium methoxide in methanol; b. removing the methanol by vacuum distillation and adding dimethylsulfoxide; c. reacting the mixture of Step (b) with cyclobutylmethyl tosylate; and d. recovering the product by extracting the mixture of Step (c) with ether and water and distillation in a vacuum.
Claim 16
Dependent Claim
67 words
A process as defined in claim 10 wherein dl-13-ethyl-3-(cyclobutylmethyloxy)gona-1,3,5(10)-trien-17-one is prepared by the steps of: a. reacting dl-13-ethyl-3-(hydroxy)-gona-1,3,5(10)-trien-17-one with sodium methoxide in methanol; b. removing the methanol by vacuum distillation and adding dimethylsulfoxide; c. reacting the mixture of Step (b) with cyclobutylmethyl tosylate; and d. recovering the product by adding water to the mixture of Step (c), extracting with ether and distilling the extract in a vacuum.
Claim 17
Dependent Claim
67 words
A process as defined in claim 10 wherein d-3-(cyclopropylmethoxy)estra-1,3,5(10)-trien-17-one is prepared by the steps of: a. reacting d-estrone with sodium methoxide in methanol; b. removing the methanol by vacuum distillation and adding dimethyl-sulfoxide; c. reacting the mixture of Step (b) with cyclopropylmethyl tosylate; and d. recovering the product by adding water to the mixture of Step (c), extracting with ether and distilling the extract in a vacuum.
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) | 1975-09-05 | 1976-03-06 | 1976-09-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-09-05 | 1980-03-06 | 1980-09-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-09-05 | 1984-03-06 | 1984-09-05 | $7700.00 | Window Closed / Lapsed |