GB973145A - New 18,20-lactones of 20-hydroxy-pregnane-18-acids - Google Patents
New 18,20-lactones of 20-hydroxy-pregnane-18-acidsInfo
- Publication number
- GB973145A GB973145A GB4255360A GB4255360A GB973145A GB 973145 A GB973145 A GB 973145A GB 4255360 A GB4255360 A GB 4255360A GB 4255360 A GB4255360 A GB 4255360A GB 973145 A GB973145 A GB 973145A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pregnane
- free
- ketones
- groups
- hydroxyl
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises the 18,20-lactones of 20b -hydroxy-pregnane-18-acids which are unsubstituted in the 11-position or which contain a free or esterified 11a -hydroxyl group, an 11-oxo group, a 9, 11-double bond or a 9, 11b -oxido group, and which are substituted in the 3-position by a free or esterified hydroxyl group or a free or ketalized oxo group. They may be of the 5a - or 5b -series and may be 19- nor compounds, and they may contain double bonds and further substituents in one or more of positions 1, 2, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17 and 21. Substituents referred to are oxido groups, free or functionally converted hydroxyl or oxo groups, alkyl groups and halogen atoms. The lactones may be prepared by the process described in Specifications 973,143 and 973,144. In the products, esterified 11a -hydroxyl groups may be hydrolyzed and the free 11a -ols oxidized to 11-ketones; D 5-3-ketals may be hydrolyzed to D 4-3-ketones or these ketalized; 3-acylates may be hydrolyzed and oxidized to 3-ketones; D 4-double bonds (and possibly D 1-double bonds) may be introduced by bromination and dehydrobromination; D 5-3-acylates may be converted to D 4-3-ketones; oxygen functions may be introduced into the 11-position by microbiological oxidation, especially with fungi of the order Mucorales, Rhizopus or with Aspergillus ochraceus and 11a -hydroxyl groups may be eliminated by conversion to sulphonic acid esters and subsequent treatment with an anhydrous base, to form a 9, 11-double bond. Examples are given, and the conversion of products of the invention to aldosterone and its derivatives is described. A by-product in one example is 3b -acetoxy-20b -hydroxy-18, 20-oxido-5a -pregnane which on hydrolysis gives the 3b -ol. In another example, -reduction of the lactone of 3b , 20b -dihydroxy 5a -pregnane-18-acid gives 3b , 18,20b -trihydroxy-5a -pregnane. Specification 973,146 also is referred to. Reference has been directed by the Comptroller to Specification 946,659.
Applications Claiming Priority (8)
| 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 |
| CH337560A CH441300A (en) | 1960-03-25 | 1960-03-25 | Process for the preparation of 18,11-lactones from 11B-hydroxy-20-oxo-steroid-18-acids of the pregnane and 19-nor-pregnane series |
| CH835460 | 1960-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB973145A true GB973145A (en) | 1964-10-21 |
Family
ID=31721975
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4255260A Expired GB973144A (en) | 1959-02-12 | 1960-12-09 | Process for the manufacture of 18:20-lactones of the pregnane series |
| GB4255360A Expired GB973145A (en) | 1959-02-12 | 1960-12-09 | New 18,20-lactones of 20-hydroxy-pregnane-18-acids |
| GB4255160A Expired GB973143A (en) | 1959-02-12 | 1960-12-09 | New hydroxy-aldehydes of the pregnane series and functional derivatives thereof and a process for their manufacture |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4255260A Expired GB973144A (en) | 1959-02-12 | 1960-12-09 | Process for the manufacture of 18:20-lactones of the pregnane series |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4255160A Expired GB973143A (en) | 1959-02-12 | 1960-12-09 | New hydroxy-aldehydes of the pregnane series and functional derivatives thereof and a process for their manufacture |
Country Status (1)
| Country | Link |
|---|---|
| GB (3) | GB973144A (en) |
-
1960
- 1960-12-09 GB GB4255260A patent/GB973144A/en not_active Expired
- 1960-12-09 GB GB4255360A patent/GB973145A/en not_active Expired
- 1960-12-09 GB GB4255160A patent/GB973143A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB973143A (en) | 1964-10-21 |
| GB973144A (en) | 1964-10-21 |
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