GB886926A - Halogenated pregnadienes and pregnatrienes and process for preparation thereof - Google Patents
Halogenated pregnadienes and pregnatrienes and process for preparation thereofInfo
- Publication number
- GB886926A GB886926A GB21980/59A GB2198059A GB886926A GB 886926 A GB886926 A GB 886926A GB 21980/59 A GB21980/59 A GB 21980/59A GB 2198059 A GB2198059 A GB 2198059A GB 886926 A GB886926 A GB 886926A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pregnadiene
- hydroxy
- dione
- steroid
- iodo
- 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
- 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 compounds having the formula <FORM:0886926/IV (b)/1> in which R is a halogen atom or a lower alkanoyloxy radical having 1-6 carbon atoms and Hal is a halogen atom and a process for the preparation thereof which comprises (a) condensing a 11a -hydroxy-4,16-pregnadiene of the general formula <FORM:0886926/IV (b)/2> with a lower alkyl oxalate to form the 2,21-bislower alkoxyoxalyl derivative and then treating with halogen to form the corresponding 2,21-bis-halo steroid (b) and, if desired, converting the product of step (a) with a lower aliphatic acid salt to form the 2-halo-21-lower alkanoyloxy steroid (c) and further, if desired, treating the products of step (a) or step (b) in which the halogen is bromine with an iodide salt to form the corresponding iodo steroid. Condensation in step (a) may be effected with ethyloxalate in the presence of sodium methoxide. Halogenation may be effected with bromine in carbon tetrachloride. In addition, compounds having the formula <FORM:0886926/IV (b)/3> wherein R1 is a lower alkanoyl radical are obtained in a process which comprises removing the elements of R111O2SOH wherein R111 is an alkyl or aryl group from the corresponding 11a -sulphonoxy steroid. Illustrative products of the invention are 2,21-dibromo-11a -hydroxy-4, 16 - pregnadiene - 3,20 - dione, 21 - acetoxy - 2 - bromo - 11a - hydroxy - 4, 16 - pregnadiene - 3,20-dione, 11a - hydroxy - 2,21 - di - iodo -4, 16 - pregnadiene - 3, 20 - dione, and 21 - acetoxy - 11a - hydroxy - 2 - iodo - 4, 16 - pregnadiene - 3,20-dione.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US886926XA | 1958-07-09 | 1958-07-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB886926A true GB886926A (en) | 1962-01-10 |
Family
ID=22212871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21980/59A Expired GB886926A (en) | 1958-07-09 | 1959-06-26 | Halogenated pregnadienes and pregnatrienes and process for preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB886926A (en) |
-
1959
- 1959-06-26 GB GB21980/59A patent/GB886926A/en not_active Expired
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