GB988801A - 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
- GB988801A GB988801A GB274062A GB274062A GB988801A GB 988801 A GB988801 A GB 988801A GB 274062 A GB274062 A GB 274062A GB 274062 A GB274062 A GB 274062A GB 988801 A GB988801 A GB 988801A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pregnan
- oic acid
- hydroxy
- alkyl ester
- compound
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0048—Molten electrolytes used at high temperature
- H01M2300/0051—Carbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises lower alkyl esters of 20 - carboalkoxy - 5b - pregnan - 11 - on - 21 - oic acids, having the general formula <FORM:0988801/C2/1> wherein R1 represents a hydrogen atom or an oxacyclic group, R1 and R3 are the same and each represents an alkyl group having 1-6 carbon atoms, and R4 is a hydrogen atom or a benzyl group and processes for the preparation thereof (a) wherein R4 is a hydrogen atom by reacting a 20-carboalkoxy-5b -pregnan-11-on-21-oic acid ester with formaldehyde to form the corresponding 20 - carboalkoxy - 20 - hydroxy-methylene - 5b - pregnan - 11 - one - 21 - oic acid - 5b - pregnan - 11 -one - 21 - oic acid ester; (b) wherein R4 is a benzyl group, by reacting a 3#c-acyloxy-20-carboalkoxy-5b -pregnan-11-on-21-oic acid alkyl ester with an alkali metal to give the corresponding alkali metal derivative at the 20-position, and condensing the latter with benzyloxychloromethane to form the corresponding 3#c - oxacyclo - 20 - carbo-alkoxy - 20 - benzyloxy - methylene -5b - pregnan - 11 -on - 21 - oic acid alkyl ester. The 3#c - oxacyclo - 20 - carbalkoxy - 5b - pregnan11-on-21-oic acid alkyl ester is obtained by reacting a 3#c-acyloxy-5b -androstane-11,17-dione with a cyanoacetic acid lower alkyl ester (1-6 carbon atoms) to obtain 3#c-acyloxy-20-cyano - 5b - pregn - 17(20) - en : 11 - on - 21-oic acid alkyl ester, catalytically hydrogenating the latter to obtain the corresponding 3#c-acyloxy - 20 - cyano - 5b - pregnan - 11 - on - 21 - oic acid lower alkyl ester, treating the latter with an alkali metal base to obtain 3#c-hydroxy-5b -pregnan - 11 - one - 20 - carboxy - 21 - oic acid, esterifying the latter with a lower aliphatic alcohol in the presence of a dehydrating agent to obtain 3#c-hydroxy-20-carboalkoxy-5b -pregnan - 11 - on - 21 - oic acid alkyl ester and treating the latter with an oxacyclic compound having a double bond in #c-position relative to the oxygen atom e.g. 2,3-dihydropyran, to obtain the desired compound. 3#c,21-Dihydroxy - 20,20 - bis - hydroxymethylene - 5b -pregnan - 11 - one is obtained by subjecting 3 - oxacyclo - 20 - carbalkoxy - 20 - benzyloxy-methylene - 5b - pregnan - 11 - on - 21 - oic acid alkyl ester to acid hydrolysis to obtain the corresponding 3#c-hydroxy-compound, treating this compound with a mixed metal hydride to obtain 3#c,11b ,21 - trihydroxy - 20 - hydroxy-methylene - 20 - benzyloxymethylene - 5b -pregnane, subjecting this compound to catalytic hydrogenolysis to form 3#c,11b ,21-tri-hydroxy - 20,20 - bis - hydroxy - methylene-5b -pregnane, acylating this compound to obtain 3#c,21 - diacyloxy - 11b - hydroxy - 20,20 - bis-acyloxymethylene - 5b - pregnane, oxidizing this compound to obtain 3#c,21-diacyloxy-20,20-bis - acyloxymethylene - 5b - pregnane - 11-one, which is saponified. Specifications 967,078, 988,805 and 988,806 are referred to.
Applications Claiming Priority (2)
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 |
FR850596A FR1331326A (en) | 1961-01-24 | 1961-01-24 | New process for the preparation of bis-hydroxymethyl pregnane derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB988801A true GB988801A (en) | 1965-04-14 |
Family
ID=26189046
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB274062A Expired GB988801A (en) | 1961-01-24 | 1962-01-24 | New steroid compounds and processes for their preparation and conversion into pharmacologically-useful compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB988801A (en) |
-
1962
- 1962-01-24 GB GB274062A patent/GB988801A/en not_active Expired
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