GB876902A - New cyclopentanophenanthrene derivatives and process for the production thereof - Google Patents
New cyclopentanophenanthrene derivatives and process for the production thereofInfo
- Publication number
- GB876902A GB876902A GB7283/58A GB728358A GB876902A GB 876902 A GB876902 A GB 876902A GB 7283/58 A GB7283/58 A GB 7283/58A GB 728358 A GB728358 A GB 728358A GB 876902 A GB876902 A GB 876902A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxyprogesterone
- acid
- anhydride
- carboxylic acids
- toluene sulphonic
- 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
Abstract
The invention comprises esters of 19-nor-17a -hydroxyprogesterone with hydrocarbon carboxylic acids of from 2 to 12 carbon atoms and a process for their preparation by reacting 19-nor-17a -hydroxyprogesterone with the appropriate acid halide or anhydride in the presence of an acid esterification catalyst, e.g. p-toluene sulphonic acid or perchloric acid, and selectively hydrolysing the resulting enol diacylate to regenerate the D 4-3-keto system. The hydrocarbon carboxylic acids may be saturated or unsaturated, cyclic or aliphatic, and may be substituted, e.g. by halo or methoxy groups. In Examples:-(1) 19-nor-17a -hydroxyprogesterone, acetic anhydride and p-toluene sulphonic acid are heated together, excess anhydride destroyed with water and the precipitated D 3,5-pregnadiene-3b , 17a -diol-20-one diacetate saponified with aqueous methanolic KOH to the acetate of 19-nor-17a -hydroxyprogesterone; (2) as in (1) but using propionic anhydride in the presence of perchloric acid, yielding the propionate of 19-nor-17a -hydroxyprogesterone; other esters similarly prepared are the butyrate, hemi-succinate, caproate, benzoate, cyclopentylpropionate, trimethylacetate, phenoxypropionate and b -chloropropionate. Specification 762,308 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MX876902X | 1957-03-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB876902A true GB876902A (en) | 1961-09-06 |
Family
ID=19743121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7283/58A Expired GB876902A (en) | 1957-03-09 | 1958-03-06 | New cyclopentanophenanthrene derivatives and process for the production thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB876902A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3372175A (en) * | 1965-11-01 | 1968-03-05 | Syntex Corp | 19-nor-14beta, 17alpha-pregnane derivatives and process |
| US3541209A (en) * | 1965-03-24 | 1970-11-17 | Schering Ag | Method of alleviating hypertrophic conditions |
-
1958
- 1958-03-06 GB GB7283/58A patent/GB876902A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3541209A (en) * | 1965-03-24 | 1970-11-17 | Schering Ag | Method of alleviating hypertrophic conditions |
| US3372175A (en) * | 1965-11-01 | 1968-03-05 | Syntex Corp | 19-nor-14beta, 17alpha-pregnane derivatives and process |
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