GB924005A - New d-homo steroids and a process for their preparation - Google Patents
New d-homo steroids and a process for their preparationInfo
- Publication number
- GB924005A GB924005A GB25205/59A GB2520559A GB924005A GB 924005 A GB924005 A GB 924005A GB 25205/59 A GB25205/59 A GB 25205/59A GB 2520559 A GB2520559 A GB 2520559A GB 924005 A GB924005 A GB 924005A
- Authority
- GB
- United Kingdom
- Prior art keywords
- homo
- androstane
- keto
- esterifying
- represent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises 18-nor-D-homo-13a -androstane compounds of the formula: <FORM:0924005/IV(a)/1> (in which R1 may represent a keto group, in which R2 and R3 which may be the same or different, will each represent a keto group or a free or esterified secondary alcoholic function in the b -orientation, or alternatively R1, R2 and R3 will each represent free secondary alcoholic functions in the b -orientation) together with processes for their preparation involving the steps of esterifying 3b -hydroxy-18-nor-D-homo-D 13(17a)-androsten - 17 - one to form a difficultly saponifiable ester at C3, enol acylating this ester at C17, brominating the product in the presence of a tertiary base followed by dehydrobromination with lithium carbonate/lithium bromide, re-esterifying the D 11,13(17a)-androstadiene at C17, subjecting the compound thus formed to the action of an alkaline borohydride, re-esterifying at C17, catalytically hydrogenating the product, effecting bromooxidation with an N-bromo-amide, oxidizing at C11 to form a keto group, and debrominating with zinc and acetic acid to yield the corresponding 3b -acyloxy-17b -acetoxy-11-keto-18-nor-D-homo-13a -androstane. Specified products of the invention are 3b -benzoyloxy-17b -hydroxy - 11-keto-18-nor-D-homo-13a -androstane, its acetate, the corresponding free 3b ,17b -diol, 3,11,17-triketo-18-nor-D-homo-13a -androstane, 3b -benzoyloxy-11,17-diketo-18-nor-D-homo-13a -androstane and 3b ,11b ,17b -trihydroxy-18-nor-D-homo-13a -androstane. Specifications 832,244, 924,006 and 924,007 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR772124 | 1958-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB924005A true GB924005A (en) | 1963-04-18 |
Family
ID=8707212
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB44098/62A Expired GB924006A (en) | 1958-08-08 | 1959-07-22 | Novel d-homo steroid compounds and processes for the preparation thereof |
| GB25205/59A Expired GB924005A (en) | 1958-08-08 | 1959-07-22 | New d-homo steroids and a process for their preparation |
| GB44099/62A Expired GB924007A (en) | 1958-08-08 | 1959-07-22 | Novel d-homo steroids and their preparations |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB44098/62A Expired GB924006A (en) | 1958-08-08 | 1959-07-22 | Novel d-homo steroid compounds and processes for the preparation thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB44099/62A Expired GB924007A (en) | 1958-08-08 | 1959-07-22 | Novel d-homo steroids and their preparations |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE581484A (en) |
| CH (1) | CH400141A (en) |
| ES (1) | ES251342A1 (en) |
| GB (3) | GB924006A (en) |
| SE (1) | SE220498C1 (en) |
-
1959
- 1959-07-13 SE SE661159A patent/SE220498C1/xx unknown
- 1959-07-22 GB GB44098/62A patent/GB924006A/en not_active Expired
- 1959-07-22 GB GB25205/59A patent/GB924005A/en not_active Expired
- 1959-07-22 CH CH7607059A patent/CH400141A/en unknown
- 1959-07-22 GB GB44099/62A patent/GB924007A/en not_active Expired
- 1959-08-07 BE BE581484A patent/BE581484A/en unknown
- 1959-08-07 ES ES0251342A patent/ES251342A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH400141A (en) | 1965-10-15 |
| GB924007A (en) | 1963-04-18 |
| SE220498C1 (en) | 1968-05-14 |
| ES251342A1 (en) | 1959-11-01 |
| BE581484A (en) | 1960-02-08 |
| GB924006A (en) | 1963-04-18 |
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