GB839908A - 4,17ª‡-dihydroxy progesterone and its esters and the preparation thereof - Google Patents
4,17ª‡-dihydroxy progesterone and its esters and the preparation thereofInfo
- Publication number
- GB839908A GB839908A GB4014157A GB4014157A GB839908A GB 839908 A GB839908 A GB 839908A GB 4014157 A GB4014157 A GB 4014157A GB 4014157 A GB4014157 A GB 4014157A GB 839908 A GB839908 A GB 839908A
- Authority
- GB
- United Kingdom
- Prior art keywords
- progesterone
- acyloxy
- dihydroxy
- esters
- derived
- 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
- 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 4,17a -dihydroxy-progesterones and p esters thereof having the general formula <FORM:0839908/IV (b)/1> wherein R and R1 are the same or different and represent hydrogen or an acyl group derived from an aliphatic carboxylic acid containing less than 9 carbon atoms, and the preparation thereof by reacting a 17a -acyloxy progesterone derived from an aliphatic carboxylic acid containing less than 9 carbon atoms with hydrogen peroxide and an alkali to form the corresponding 4,5 - epoxy - 17a - acyloxy - progesterone in the form of a mixture of the 4,5b - and 4,5a -isomers, reacting the 4,5-epoxy compounds with a mixture of glacial acetic acid and concentrated sulphuric acid to form 4-hydroxy-17a -acyloxy-progesterone (which may exist in the ketonic form, i.e. 3,4,20-triketo-17a -acyloxy-pregnane), and hydrolysing this compound to form 4,17a -dihydroxy-progesterone. The esters may be prepared by esterifying the 4,17a -dihydroxy-progesterone or 4 - hydroxy - 17a - acyloxy-progesterone, thus 4,17a - dihydroxy - progesterone may be selectively acylated in the 4-position with the required anhydride in the presence of pyridine. The ester groups may be derived from formic, acetic, propionic, butyric, valerionic, caproic, enanthic, caprylic, b -cyclopentanepropionic and cyclohexaneacetic acids. In the examples 4,17a -dihydroxyprogesterone and the 4-acetate, 4,17-diacetate and 17-caproate thereof are prepared.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4014157A GB839908A (en) | 1957-12-24 | 1957-12-24 | 4,17ª‡-dihydroxy progesterone and its esters and the preparation thereof |
| CH6761558A CH374996A (en) | 1957-12-24 | 1958-12-23 | Process for the preparation of 4-oxy-17a-acyloxyprogesterones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4014157A GB839908A (en) | 1957-12-24 | 1957-12-24 | 4,17ª‡-dihydroxy progesterone and its esters and the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB839908A true GB839908A (en) | 1960-06-29 |
Family
ID=10413388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4014157A Expired GB839908A (en) | 1957-12-24 | 1957-12-24 | 4,17ª‡-dihydroxy progesterone and its esters and the preparation thereof |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH374996A (en) |
| GB (1) | GB839908A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001042275A1 (en) * | 1999-12-08 | 2001-06-14 | Jenapharm Gmbh & Co. Kg | Unsaturated 14,15-cyclopropane-androstanes, a method for their production and pharmaceutical compositions containing these compounds |
-
1957
- 1957-12-24 GB GB4014157A patent/GB839908A/en not_active Expired
-
1958
- 1958-12-23 CH CH6761558A patent/CH374996A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001042275A1 (en) * | 1999-12-08 | 2001-06-14 | Jenapharm Gmbh & Co. Kg | Unsaturated 14,15-cyclopropane-androstanes, a method for their production and pharmaceutical compositions containing these compounds |
| US6710039B1 (en) | 1999-12-08 | 2004-03-23 | Schering Ag | Unsaturated 14,15-cyclopropane-androstanes, a method for their production and pharamceutical compositions containing these compounds |
| USRE39862E1 (en) * | 1999-12-08 | 2007-09-25 | Schering Ag | Unsaturated 14, 15-cyclopropanoandrostanes, a method for their production and pharmaceutical compositions containing these compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| CH374996A (en) | 1964-02-15 |
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