US3755302A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the production of 17-monesters of 17{60 , 21-dihydroxy-steroids and products thereof
Assignee: Warner Lambert Co LLC
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Filing: 1970-06-22
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Granted: 1973-08-28
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Expires: 1990-06-22
Abstract
Abstract This invention relates to an improved process for the preparation of 17-monoesters of 17 Alpha , 21-dihydroxy-20-ketosteroids which consists in carrying out the hydrolysis of corresponding 17,21-cyclic orthoesters in a buffered aqueousorganic medium at a pH from about 4 to about 6. This invention also relates to new 17-esters of 17 Alpha , 21-dihydroxy-steroids having an epoxy group at the 9 Beta , 11 Beta -position, useful as intermediates for the preparation of therapeutically active 17-esters.
Inventors
- 👤 R Vitali
- 👤 A Ercoli
- 👤 R Gardi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 21:11
CPC Classifications
C; C07; C07J; C07J5/00
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
21 words
A process as claimed in claim 1 in which the pH of said buffered aqueous-organic medium is from 4.5 to 5.5.
Claim 2
Dependent Claim
25 words
A process as claimed in claim 1 in which an aqueous solution of 0.1N acetic acid and 0.1M sodium acetate is used as a buffer.
Claim 3
Dependent Claim
25 words
A process as claimed in claim 1 in which an aqueous solution of 0.1N hydrochloric acid and 0.1M sodium citrate is used as a buffer.
Claim 4
Dependent Claim
26 words
A process as claimed in claim 1 in which an aqueous solution of 0.2N hydrochloric acid and 0.2M potassium hydrogen phthalate is used as a buffer.
Claim 5
Dependent Claim
44 words
A process as claimed in claim 3 in which a mixture of 5 volumes of methanol and 2 volumes of an aqueous solution containing 9 parts of 0.1N acetic acid and 1 part of 0.1M sodium acetate is used as a buffered aqueous-organic medium.
Claim 6
Dependent Claim
92 words
A process for the preparation of 17 Alpha -acetoxy- Delta 4-pregnen-21-ol-3,20-dione which comprises hydrolysing the 17 Alpha ,21-(1''-methoxy)-ethylidenedioxy- Delta 4-pregnene-3,20-dione in a buffered aqueous-organic medium having a pH in the range of from 4.5 to 5.5, utilizing a buffer system selected from the group consisting of 0.1N acetic acid and 0.1M sodium acetate; 0.1N hydrochloric acid and 0.1M sodium citrate; 0.2N hydrochloric acid and 0.2M potassium hydrogen phthalate; 0.2M potassium hydrogen phthalate and 0.2N sodium hydroxide; 0.1N hydrochloric acid and 0.1N glycine; and 0.05M potassium hydrogen phthalate and 1/15M potassium dihydrogen phosphate.
Claim 7
Dependent Claim
109 words
A process for the preparation of 17-esters of 17,21-dihydroxy-3,20-diketo- Delta 4-pregnenes and Delta 1,4-pregnadienes bearing a 9(11) double bond or an epoxy group at the 9 Beta ,11 Beta -position which comprises hydrolysing a corresponding 17,21-cyclic orthoester in a buffered aqueous-organic medium having a pH in the range of from 4.5 to 5.5, utilizing a buffer system selected from the group consisting of 0.1N acetic acid and 0.1M sodium acetate; 0.1N hydrochloric acid and 0.1M sodium citrate; 0.2N hydrochloric acid and 0.2M potassium hydrogen phthalate; 0.2M potassium hydrogen phthalate and 0.2N sodium hydroxide; 0.1N hydrochloric acid and 0.1N glycine; and 0.05M potassium hydrogen phthalate and 1/15M potassium dihydrogen phosphate.
Claim 8
Dependent Claim
10 words
A process for the preparation of a compound of formula:
Claim 9
Dependent Claim
21 words
A process as claimed in claim 9 in which the pH of said buffered aqueous-organic medium is from 4.5 to 5.5.
Claim 10
Dependent Claim
46 words
A process as claimed in claim 9 in which the starting 17,21-orthoester is 17 Alpha ,21-(1''-methoxy)-benzylidenedioxy-9 Beta , 11 Beta -oxido-16 Beta -methyl- Delta 4-pregnene-3,20-dione and the product of the hydrolysis is the 17-benzoate of 9 Beta ,11 Beta -oxido-16 Beta -methyl Delta 4-pregnene-17 Alpha ,21-diol-3,20-dione.
Claim 11
Dependent Claim
48 words
A process as claimed in claim 9 in which the starting 17,21-orthoester is 17 Alpha ,21-(1''-methoxy)-benzylidenedioxy-9 Beta , 11 Beta -oxido-16 Beta -methyl- Delta 1,4-pregnadiene-3,20-dione and the product of the hydrolysis is the 17-benzoate of 9 Beta , 11 Beta -oxido-16 Beta -methyl- Delta 1,4-pregnadiene-17 Alpha , 21-diol-3,20-dione.
Claim 12
Dependent Claim
4 words
A compound of formula:
Claim 13
Dependent Claim
12 words
9 Beta ,11 Beta -oxido-16 Beta -methyl- Delta 1,4-pregnadiene-17 Alpha ,21-diol-3,20-dione 17-benzoate.
Claim 14
Dependent Claim
12 words
9 Beta ,11 Beta -oxido-16 Beta -methyl- Delta 1,4-pregnadiene-17 Alpha ,21-diol-3,20-dione 17-valerate.
Claim 15
Dependent Claim
12 words
9 Beta ,11 Beta -oxido-6 Alpha -fluoro- Delta 1,4-pregnadiene-17 Alpha ,21-diol-3,20-dione 17-propionate.
Claim 16
Dependent Claim
12 words
9 Beta ,11 Beta -oxido-6 Alpha -fluoro- Delta 1,4-pregnadiene-17 Alpha ,21-diol-3,20-dione 17-butyrate.
Claim 17
Dependent Claim
12 words
9 Beta ,11 Beta -oxido-6 Alpha -fluoro- Delta 1,4-pregnadiene-17 Alpha ,21-diol-3,20-dione 17-isobutyrate.
Claim 18
Dependent Claim
12 words
9 Beta ,11 Beta -oxido-6 Alpha -fluoro- Delta 1,4-pregnadiene-17 Alpha ,21-diol-3,20-dione 17-valerate.
Claim 19
Dependent Claim
91 words
A process for the preparation of prednisolone 17-benzoate which comprises hydrolysing 17 Alpha ,21-(1''-lower alkyl)-benzylidenedioxy- Delta 1,4-pregnadien 11 Beta -ol-3,20-dione in a buffered aqueous-organic medium having a pH value from about 4 to about 6, utilizing a buffer system selected from the group consisting of 0.1N acetic acid and 0.1M sodium acetate; 0.1N hydrochloric acid and 0.1M sodium citrate; 0.2N hydrochloric acid and 0.2M potassium hydrogen phthalate; 0.2M potassium hydrogen phthalate and 0.2N sodium hydroxide; 0.1N hydrochloric acid and 0.1N glycine; and 0.05M potassium hydrogen phthalate and 1/15M potassium dihydrogen phosphate.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1976-08-27 | 1977-02-26 | 1977-08-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1980-08-27 | 1981-02-26 | 1981-08-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1984-08-27 | 1985-02-26 | 1985-08-28 | $7700.00 | Window Closed / Lapsed |