GB973146A - 9-halogenated 18:11-lactones of 11ª‰-hydroxy-pregnane-18-acids - Google Patents
9-halogenated 18:11-lactones of 11ª‰-hydroxy-pregnane-18-acidsInfo
- Publication number
- GB973146A GB973146A GB4255460A GB4255460A GB973146A GB 973146 A GB973146 A GB 973146A GB 4255460 A GB4255460 A GB 4255460A GB 4255460 A GB4255460 A GB 4255460A GB 973146 A GB973146 A GB 973146A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- lactones
- acids
- pregnene
- oxo
- 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
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- 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 18, 11-lactones of 11b -hydroxy-9a - X- 20- R1-21-R2-pregnane-18-acids in which X is a fluorine, chlorine or bromine, R1 is a free or ketalized oxo group, or a hydrogen atom and a free or esterified hydroxyl group, and R2 is a hydrogen atom or a free, esterified or etherified hydroxyl group, and particularly steroids of this class having the formula <FORM:0973146/C1/1> and the corresponding D 5-3-ketals, and the 19-nor analogues of all these steroids. They may be prepared by treating the 18, 20b -lactones of D 4-3-oxo-9, 11b - oxido-20b -hydroxy-pregnene 18-acids with a hydrohalic acid and then translactonizing the resulting 18, 20-lactones of 9a -halogen-11b -hydroxy-pregnene-18-acids. The 9a -bromo compounds can also be prepared by direct additive combination of hypobromous acid with the 18, 20-lactone of D 4,9(11)-3-oxo-20b -hydroxy-pregnadiene-18-acid Oxidation of the so-formed 20-hydroxy compounds gives the 20-ketones, while treatment with, for example, ethylene glycol and p-toluenesulphonic acid gives the corresponding D 5-3-ethylenedioxy compounds, which may also be oxidized to the 20-ketones. The D 5-3-ketals may be further processed by oxalic ester condensation, iodination and cleavage with sodium acetate into the 18, 11-lactones of D 5-3-ethylenedioxy-9a -halo-11b -hydroxy -20 - oxo - 21 - acetoxy - pregnene-18-acids which on treatment with aqueous perchloric acid in tetrahydrofuran yield the 18, 11-lactones of D 4-3, 20-dioxo-11b , 21-dihydroxy-9a -halo-pregnene -18-acids. By ketalization, reduction with lithium aluminium hydride and ketal cleavage these may be converted to 9a -halo-aldosterones. Detailed examples of all these processes are given. Specifications 973,143, 973,144 and 973,145 are referred to.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH6947559A CH383953A (en) | 1959-02-12 | 1959-02-12 | Process for the preparation of 18,20-oxido-steroids |
CH7244359 | 1959-04-23 | ||
CH7375459 | 1959-05-29 | ||
CH8178059A CH407111A (en) | 1959-12-11 | 1959-12-11 | Process for the production of new hydroxyaldehydes of the Pregnan range |
CH8223359 | 1959-12-22 | ||
CH185860A CH432510A (en) | 1959-02-12 | 1960-02-18 | Process for the preparation of 18,20-lactones of the pregnan and 19-nor-pregnan series |
Publications (1)
Publication Number | Publication Date |
---|---|
GB973146A true GB973146A (en) | 1964-10-21 |
Family
ID=31721874
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4255460A Expired GB973146A (en) | 1959-02-12 | 1960-12-09 | 9-halogenated 18:11-lactones of 11ª‰-hydroxy-pregnane-18-acids |
Country Status (2)
Country | Link |
---|---|
CH (1) | CH432510A (en) |
GB (1) | GB973146A (en) |
-
1960
- 1960-02-18 CH CH185860A patent/CH432510A/en unknown
- 1960-12-09 GB GB4255460A patent/GB973146A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
CH432510A (en) | 1967-03-31 |
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