GB862235A - Dihalogen derivatives of steroids and methods for their production - Google Patents
Dihalogen derivatives of steroids and methods for their productionInfo
- Publication number
- GB862235A GB862235A GB1906758A GB1906758A GB862235A GB 862235 A GB862235 A GB 862235A GB 1906758 A GB1906758 A GB 1906758A GB 1906758 A GB1906758 A GB 1906758A GB 862235 A GB862235 A GB 862235A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetate
- dibromomethylene
- dibromo
- methylene
- testosterone
- 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
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- 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
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- 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 6-dichloromethylene and 6-dibromomethylene derivatives of D 4-3-keto-steroid compounds of the androstane, 19-nor-androstane, pregnane and 19-nor-pregnane series having a saturated B ring, and the preparation thereof by reacting a 3-enol ether or a ketal of a D 4-3-keto-steroid of the androstane, 19-nor-androstane, pregnane or 19-nor-pregnane series having a saturated B ring with a tetrahalogenomethane in which the halogen is either bromine or both chlorine and bromine. An intermediate 6-trihalogenomethyl derivative is first formed which is unstable and slowly transforms into the desired 6-dihalogenomethylene derivative. The transformation may be speeded up by the action of an acid-binding substance such as pyridine or collidine, an organic peroxide or magnesium, or by irradiation with light of a wavelength between 2000 and 8000 . In some cases it is possible to isolate the intermediate 6-trichloromethyl or 6-tribromomethyl steroid of the above series. In the examples the following compounds are prepared: 6-tribromo (and trichloro)-methyl-testosterone, 6-dibromo (and chloro)-methylene-testosterone, 6-dibromomethylene - testosterone acetate, 6 - dibromomethylene - 17a - methyl - testosterone, 6 - dibromomethylene - 19 - nor - testosterone acetate, 6 - dibromo (and chloro) - methylene - progesterone, 6 - dibromemethylene - 17a - hydroxyprogesterone and the corresponding 17-acetate, 6 - dibromo - methylene - 11 - desoxyacetate, 6 - dibromo - methylene - 11 - desoxycorticosterone acetate, 6-dibromo-methylene-17a - hydroxy - 11 - desoxycorticosterone 12 - acetate, and the 20 - ethyleneketal of 6-dibromomethylene-cortisone acetate. The first Provisional Specification refers to progesterone derivatives prepared by the above process having various substituents such as a hydroxyl group in the 17- or 21-position or in both positions, which may be esterified, a keto or hydroxyl group in the 11-position, and a fluorine or chlorine atom in the 9-position. The hydroxyl groups in the 11- and 17-position may be an a - or b -hydroxyl group. The Provisional Specifications also state that the products of the above process have at the A and B ring the formula <FORM:0862235/IV (b)/1> wherein X represents chlorine or bromine.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1906758A GB862235A (en) | 1958-06-13 | 1958-06-13 | Dihalogen derivatives of steroids and methods for their production |
| BE579663A BE579663A (en) | 1958-06-13 | 1959-06-13 | New steroid derivatives of the androstane and pregnane series and process for the preparation of these derivatives. |
| CH7441259A CH376909A (en) | 1958-06-13 | 1959-06-13 | Process for the preparation of 6a, 6a-dichloro-6,7-methylene and 6a, 6a-dibromo-6,7-methylene compounds of 4-3-keto steroids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1906758A GB862235A (en) | 1958-06-13 | 1958-06-13 | Dihalogen derivatives of steroids and methods for their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB862235A true GB862235A (en) | 1961-03-08 |
Family
ID=10123222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1906758A Expired GB862235A (en) | 1958-06-13 | 1958-06-13 | Dihalogen derivatives of steroids and methods for their production |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB862235A (en) |
-
1958
- 1958-06-13 GB GB1906758A patent/GB862235A/en not_active Expired
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