GB788895A - New derivatives of androstadiene and their production - Google Patents
New derivatives of androstadiene and their productionInfo
- Publication number
- GB788895A GB788895A GB13014/56A GB1301456A GB788895A GB 788895 A GB788895 A GB 788895A GB 13014/56 A GB13014/56 A GB 13014/56A GB 1301456 A GB1301456 A GB 1301456A GB 788895 A GB788895 A GB 788895A
- Authority
- GB
- United Kingdom
- Prior art keywords
- androstadiene
- semicarbazone
- alcoholate
- ethynyl
- amide
- 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
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises androstadienes of the general formula <FORM:0788895/IV (b)/1> wherein R represents <FORM:0788895/IV (b)/2> and the 3-semicarbazone derivatives thereof, and the preparation of these compounds by reacting D 1,4 - androstadiene - 3,11,17 - trione with acetylene in the presence of an alkali metal or alkaline earth metal alcoholate or amide, the reaction being effected in an inert organic solvent or in liquid ammonia to form 17b -hydroxy - 17a - ethynyl - D 1,4 - androstadiene - 3,11-dione, this product is then converted into the 3-semicarbazone derivative thereof which is then reduced with an alkali or alkaline earth metal borohydride to form the 3-semicarbazone of 11b ,17b -dihydroxy-17a -ethynyl-D 1,4-androstadiene-3-one, and further reaction with pyruvic acid forms 11b ,17b -dihydroxy-17a -ethynyl- D 1,4-androstadiene-3-one. Potassium tertiary amylate is the preferred alcoholate for use in the above process. The 3-semicarbazone derivative may be formed using semi-carbazide acetate as the reagent and alcohol as the reaction solvent. The mixed hydride for the reduction step may be a potassium, sodium, lithium, or calcium borohydride, and the alkali or alkaline earth metal alcoholate or amide may be potassium, lithium or calcium alcoholate or amide. The examples illustrate the preparation of all the androstadienes of the above general formula. Specification 757,950 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR788895X | 1956-01-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB788895A true GB788895A (en) | 1958-01-08 |
Family
ID=9219801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13014/56A Expired GB788895A (en) | 1956-01-13 | 1956-04-27 | New derivatives of androstadiene and their production |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB788895A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3127314A (en) * | 1964-03-31 | Method of reducing hyperlipemia by |
-
1956
- 1956-04-27 GB GB13014/56A patent/GB788895A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3127314A (en) * | 1964-03-31 | Method of reducing hyperlipemia by |
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