GB978725A - Novel steroid compounds and processes for their perparation - Google Patents
Novel steroid compounds and processes for their perparationInfo
- Publication number
- GB978725A GB978725A GB2011062A GB2011062A GB978725A GB 978725 A GB978725 A GB 978725A GB 2011062 A GB2011062 A GB 2011062A GB 2011062 A GB2011062 A GB 2011062A GB 978725 A GB978725 A GB 978725A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trione
- pregna
- hydroxy
- pregn
- ene
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises 17a -hydroxy-pregn-4-ene-3, 11, 20-trione derivatives having the formula: <FORM:0978725/C1/1> in which "R" represents a hydrogen atom or an acyl group derived from an organic carboxylic acid having from 1-18 carbon atoms and processes for the preparation thereof in which a compound of the formula: <FORM:0978725/C1/2> where R1 and R11, which may be the same or different, each represents an hydrogen atom or an alkyl group having from 1-6 carbon atoms and n is 0 or 1 is subjected to catalytic hydrogenation to eliminate the double bond at the 16-17 position thus forming the corresponding 3-cyclic ketal of 18-nor-pregna-3, 11, 20-trione which is then hydroperoxygenated at the 17-position by the action of oxygen in the presence of an alkali metal alcoholate, thus forming the corresponding 3-cyclic ketal of 17a -hydroperoxy -18- nor-pregna-3, 11, 20-trione, which is reduced to form the 3-cyclic ketal of 17a -hydrohydroxy-18-nor-pregna-3, 11, 20-trione, the protected 3-keto group of which is then liberated by acid hydrolysis to form 17a -hydroxy-18-norpregna-3, 11, 20-trione, which is brominated to form 4#x-bromo-17a -hydroxy-18-nor-pregna-3, 11, 20-trione and the latter is dehydrobrominated thus forming 17a -hydroxy-18-nor-pregn-4-ene -3, 11, 20-trione, which is finally subjected to either treatment with a microbiological hydroxylating agent or to halogenation followed by acyloxylation and saponification, to yield 17a -, 21-dihydroxy -18- nor-pregn-4-ene-3, 11, 20-trione which may be esterified if desired to form the corresponding 21-ester. The hydroperoxy compound may be formed in the presence of potassium t-butylate, whilst 21-hydroxylation may be effected using a culture of Colletotrichum lindemuthianum or by iodinating to form a 21-diiodo derivative followed by acyloxylation using an alkali metal acylate and saponification. Specification 978,725 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR862706A FR1369316A (en) | 1961-05-24 | 1961-05-24 | Cortisone derivatives and method of preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
GB978725A true GB978725A (en) | 1964-12-23 |
Family
ID=8755755
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2082664A Expired GB978726A (en) | 1961-05-24 | 1961-05-24 | Novel steroid compounds and processes for the preparation thereof |
GB2011062A Expired GB978725A (en) | 1961-05-24 | 1962-05-24 | Novel steroid compounds and processes for their perparation |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2082664A Expired GB978726A (en) | 1961-05-24 | 1961-05-24 | Novel steroid compounds and processes for the preparation thereof |
Country Status (3)
Country | Link |
---|---|
CH (1) | CH414613A (en) |
FR (1) | FR1369316A (en) |
GB (2) | GB978726A (en) |
-
1961
- 1961-05-24 GB GB2082664A patent/GB978726A/en not_active Expired
- 1961-05-24 FR FR862706A patent/FR1369316A/en not_active Expired
-
1962
- 1962-05-17 CH CH598862A patent/CH414613A/en unknown
- 1962-05-24 GB GB2011062A patent/GB978725A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
GB978726A (en) | 1964-12-23 |
FR1369316A (en) | 1964-08-14 |
CH414613A (en) | 1966-06-15 |
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