GB988802A - New steroid compounds, processes for their preparation, and compositions incorporating them - Google Patents
New steroid compounds, processes for their preparation, and compositions incorporating themInfo
- Publication number
- GB988802A GB988802A GB1245162A GB1245162A GB988802A GB 988802 A GB988802 A GB 988802A GB 1245162 A GB1245162 A GB 1245162A GB 1245162 A GB1245162 A GB 1245162A GB 988802 A GB988802 A GB 988802A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- pregnan
- phosphato
- bis
- acid
- 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
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises 21-hydroxy-20,20-bis - hydroxymethylene - 3#c - phosphato - 5b -pregnan-11-one and derivatives thereof having the general formula <FORM:0988802/C2/1> where R3 represents an hydrogen atom or acyl radical derived from either an inorganic mineral acid or from an organic carboxylic acid having from 1 to 18 carbon atoms, their non toxic water soluble salts, pharmaceutical compositions thereof, and processes for the preparation thereof, in which 3#c,21-dihydroxy-20,20-bis-hydroxy-methylene - 5b - pregnan - 11 - one is condensed with a lower alkyl ortho lower aliphatic acylate to protect the side chain hydroxyl groups thereof by forming 11-(3#c-hydroxy-5b -androstan - 11 - on - 17b - yl) - 31,51,81 - trioxa-bicyclo - [2,2,2] - octane or a derivative thereof having the formula <FORM:0988802/C2/2> (where R is hydrogen or a lower alkyl group), this is then reacted with a functional derivative of phosphoric acid to form the corresponding 11-(3#c - diaralkylphosphato - 5b - androstan - 11 - on - 31,51,81 - trioxa - bicyclo - [2,2,2]-octane or derivative thereof, and acid hydrolysis is effected to liberate the protected hydroxyl groups yielding, after hydrogenolysis 3a - phosphato - 21 - hydroxy - 20,20 - bis-hydroxymethylene - 5b - pregnan - 11 - one. As alkyl ortho aliphatic acylate there may be use ethyl ortho formate, as functional derivative of phosphoric acid there may be used dibenzyl chlorophosphonate. Hydrogenolysis may be performed with palladium black in the presence of a solvent which consists wholly or predominantly of methanol. Subsequently the 3a - phosphato 21 - hydroxy compound may be esterified at 21-position for example with fuming nitric acid to form 21-nitrato-20,20-bis-nitratomethylene - 3a - phosphato - 5b - pregnan - 11 - one or converted into a non-toxic water-soluble salt. Said pharmaceutical compositions, having vasodilative action, may be employed as injectable solutions and suspensions, tablets, drinkable drops or suppositories. Specifications 988,078 and 988,801 are referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR857376A FR1368718A (en) | 1961-03-30 | 1961-03-30 | Bis-hydroxymethyl pregnane derivatives |
| FR866469A FR1418M (en) | 1961-03-30 | 1961-06-29 | New drug for the treatment of coronary artery spasms. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB988802A true GB988802A (en) | 1965-04-14 |
Family
ID=26189922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1245162A Expired GB988802A (en) | 1961-03-30 | 1962-03-30 | New steroid compounds, processes for their preparation, and compositions incorporating them |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE615766A (en) |
| CH (1) | CH416614A (en) |
| ES (1) | ES275942A1 (en) |
| GB (1) | GB988802A (en) |
-
1962
- 1962-03-27 CH CH363462A patent/CH416614A/en unknown
- 1962-03-29 BE BE615766A patent/BE615766A/en unknown
- 1962-03-29 ES ES275942A patent/ES275942A1/en not_active Expired
- 1962-03-30 GB GB1245162A patent/GB988802A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES275942A1 (en) | 1962-06-16 |
| CH416614A (en) | 1966-07-15 |
| BE615766A (en) | 1962-10-01 |
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