ES252828A1 - Improvements in or relating to steroids - Google Patents
Improvements in or relating to steroidsInfo
- Publication number
- ES252828A1 ES252828A1 ES0252828A ES252828A ES252828A1 ES 252828 A1 ES252828 A1 ES 252828A1 ES 0252828 A ES0252828 A ES 0252828A ES 252828 A ES252828 A ES 252828A ES 252828 A1 ES252828 A1 ES 252828A1
- Authority
- ES
- Spain
- Prior art keywords
- ethyl
- hydroxy
- dione
- compound
- androsta
- 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
- 150000003431 steroids Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- HNDUFCYJJVPVMF-AEIBSFOJSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-7,8,9,12,14,15,16,17-octahydro-6h-cyclopenta[a]phenanthrene-3,11-dione Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2=O HNDUFCYJJVPVMF-AEIBSFOJSA-N 0.000 abstract 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- IQUXBKUKXDWZLA-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 IQUXBKUKXDWZLA-VMXHOPILSA-N 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- FNXLCIKXHOPCKH-UHFFFAOYSA-N bromamine Chemical compound BrN FNXLCIKXHOPCKH-UHFFFAOYSA-N 0.000 abstract 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 229940107700 pyruvic acid Drugs 0.000 abstract 1
- 230000001172 regenerating effect Effects 0.000 abstract 1
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 steroids of the general formula <FORM:0923736/IV(a)/1> wherein R represents a keto or b -hydroxy radical, and the corresponding 3-semicarbazones and 3-oximes, and the preparation of 17a -ethyl-17b -hydroxy-D 1,4-androstadiene-3,11-dione by treating 3a -acetoxy-5b -androsta-11, 17-dione with an alkali metal acetylide to form 17a - ethynyl - 3a ,17b -dihydroxy-5b -androstan-11-one, catalytically hydrogenating this compound to form the corresponding 17a -ethyl compound, bromoxidising the 17a -ethyl compound with an N-bromoamide to form 4b -bromo - 17a - ethyl-17b -hydroxy-5b -androsta-3,11-dione, brominating this compound to form 2b ,4b - dibromo - 17a -ethyl-17b -hydroxy-5b -androsta-3,11-dione and dehydrobrominating this compound, the preparation of 17a -ethyl - 11b ,17a - dihydroxy - D 1,4 - androstadien-3-one by converting 17a -ethyl-17b -hydroxy-D 1,4-androstadiene-3,11-dione into the corresponding 3-semicarbazone or oxime, reducing the 11-keto group to an 11b -hydroxy group with an alkali metal borohydride, and regenerating the 3-keto group by reaction with pyruvic acid. Specifications 816,909, 923,737 and 923,738 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR777439A FR1261174A (en) | 1958-10-24 | 1958-10-24 | Process for the preparation of novel derivatives of delta 1-dehydro adrenosterone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES252828A1 true ES252828A1 (en) | 1959-12-16 |
Family
ID=8707820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0252828A Expired ES252828A1 (en) | 1958-10-24 | 1959-10-23 | Improvements in or relating to steroids |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE583959A (en) |
| CH (1) | CH394179A (en) |
| ES (1) | ES252828A1 (en) |
| FR (1) | FR1261174A (en) |
| GB (3) | GB923737A (en) |
-
1958
- 1958-10-24 FR FR777439A patent/FR1261174A/en not_active Expired
-
1959
- 1959-10-12 CH CH7929959A patent/CH394179A/en unknown
- 1959-10-14 GB GB3925162A patent/GB923737A/en not_active Expired
- 1959-10-14 GB GB3825262A patent/GB923738A/en not_active Expired
- 1959-10-14 GB GB3482559A patent/GB923736A/en not_active Expired
- 1959-10-23 BE BE583959A patent/BE583959A/en unknown
- 1959-10-23 ES ES0252828A patent/ES252828A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB923738A (en) | 1963-04-18 |
| FR1261174A (en) | 1961-05-19 |
| CH394179A (en) | 1965-06-30 |
| GB923737A (en) | 1963-04-18 |
| GB923736A (en) | 1963-04-18 |
| BE583959A (en) | 1960-04-25 |
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