GB988806A - New steroid compounds and processes for their preparation and conversion into pharmacologically-useful compounds - Google Patents
New steroid compounds and processes for their preparation and conversion into pharmacologically-useful compoundsInfo
- Publication number
- GB988806A GB988806A GB1626664A GB1626664A GB988806A GB 988806 A GB988806 A GB 988806A GB 1626664 A GB1626664 A GB 1626664A GB 1626664 A GB1626664 A GB 1626664A GB 988806 A GB988806 A GB 988806A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- pregnan
- hydroxymethylene
- hydroxy
- acyl radical
- 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)
- Steroid Compounds (AREA)
Abstract
The invention comprises 5b -pregnanes, having the formula <FORM:0988806/C2/1> wherein R1 is a hydrogen atom or an acyl radical, and either R2 is a b -hydroxyl group H(OH) in which case R3 and R4 are each a hydrogen atom or an acyl radical and R5 is a hydrogen atom, an acyl radical or a benzyl group, or R2 is the oxygen atom of a keto group, and R3, R4, and R5 together are a methylene group CH, the acyl radical in each case being derived from an aliphatic carboxylic acid having from 2-7 carbon atoms and processes for the preparation thereof by treating a 3a -hydroxy - 20 - carboalkoxy - 20 - benzyloxymethylene - 5b - pregnan - 11 - on - 21 - oic acid alkyl ester with a mixed metal hydride to form 3a ,11b ,21 - trihydroxy - 20 - hydroxymethylene - 20 - benzyloxy - methylene - 5b - pregnane, subjecting the latter to catalytic hydrogenolysis to give 3a ,11b ,21-trihydroxy-20,20-bis - hydroxymethylene - 5b - pregnane, reacting the latter with an acylating agent derived from a lower aliphatic carboxylic acid having 2-7 carbon atoms to obtain 3a ,21-diacyloxy-11b - hydroxy - 20,20 - bis - acyloxymethylene-5b - pregnane, oxidizing the latter by treatment with a mixture of chromic acid and concentrated sulphuric acid to obtain 3a ,21-diacyloxy - 20,20 - bis - acyloxymethylene - 5b -pregnan - 11 - one, saponifying the latter by treatment with alkali to obtain 3a ,21 - dihydroxy - 20,20 - bis - hydroxymethylene - 5b -pregnan - 11 - one, reacting the latter with a lower alkyl ortho-lower aliphatic acylate e.g. lower alkyl orthoformate to obtain 11-(3a -hydroxy - 5b - androstan - 11 - on - 17b - yl)-31,51,81\h - trioxabicyclo - [2,2,2] - octane, treating the latter with an acylating agent to obtain the corresponding 3-acyloxy compound and subjecting the latter to hydrolysis to obtain 3a -acyloxy - 20,20 - bis - hydroxymethylene - 21 - hydroxy - 5b - pregnan - 11 - one. As mixed metal hydride, LiAlH4 may be used. Catalytic hydrogenolysis is preferably effected in ethanol with palladium black. Specification 967,078 also is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR850597A FR1287418A (en) | 1961-01-24 | 1961-01-24 | New process for the preparation of tetroxygenated derivatives of bis-hydroxymethylpregnane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB988806A true GB988806A (en) | 1965-04-14 |
Family
ID=8747350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1626664A Expired GB988806A (en) | 1961-01-24 | 1962-01-24 | New steroid compounds and processes for their preparation and conversion into pharmacologically-useful compounds |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH407995A (en) |
| FR (1) | FR1287418A (en) |
| GB (1) | GB988806A (en) |
-
1961
- 1961-01-24 FR FR850597A patent/FR1287418A/en not_active Expired
-
1962
- 1962-01-23 CH CH79262A patent/CH407995A/en unknown
- 1962-01-24 GB GB1626664A patent/GB988806A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1287418A (en) | 1962-03-16 |
| CH407995A (en) | 1966-02-28 |
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