GB902373A - Steroids and preparation thereof - Google Patents
Steroids and preparation thereofInfo
- Publication number
- GB902373A GB902373A GB10624/60A GB1062460A GB902373A GB 902373 A GB902373 A GB 902373A GB 10624/60 A GB10624/60 A GB 10624/60A GB 1062460 A GB1062460 A GB 1062460A GB 902373 A GB902373 A GB 902373A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- methyl
- steroids
- hydroxyl
- give
- 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises (1) a process for preparing steroids of the formula <FORM:0902373/IV (b)/1> (wherein R1 is hydrogen or methyl, R2 is hydrogen, fluorine, chlorine or methyl, R3 is hydrogen or hydroxyl, R4 is hydrogen, a -fluorine, a - or b -methyl, methylene, a -hydroxyl or acylated a -hydroxyl, at least three of R1, R2, R3 and R4 being hydrogen in a specific compound, and R5 is hydrogen, X is hydrogen, halogen, methoxy or ethoxy, and Y is keto or b -hydroxyl) which comprises reducing the corresponding 17-pyruvoyl compounds with a yeast of the genus Saccharomyces or an alkali metal hydride, and, if desired, converting the product to an acylate or 16, 17-acetonide thereof; and (2) 21-acylates of all the steroids of the above formula and 21-hydroxy steroids of the above formula when R2 is chlorine. The acyl group or groups contain only carbon, hydrogen and oxygen and are derived from mono- or di-carboxylic acids containing at most 10 carbon atoms, and those containing a free carboxyl group may be converted to alkali or alkaline earth metal salts. The reduction is preferably conducted with S. cerevisiae or with a borohydride or alkoxy borohydride, desirably used in about an equimolecular proportion to the steroid, although if methanol is used as solvent up to 2.8 molar equivalents may be used. Reduction products may be mono- or di-acylated or converted into 16,17-acetonides by standard procedures, or separated into 21-epimeric forms. Examples are given and a list of suitable esterifying acids and aldehydes and ketones for the preparation of acetonides is provided. 21-Methyl - D 4 - pregnadiene-11b ,17a ,21-triol-3,20-dione is prepared by reacting cortisol with cupric acetate to give the 21-aldehyde, treating this with diazomethane to give the 21,22-epoxide, treating this with hydrogen chloride to give 21-chloromethyl-cortisol and warming this with bismuth trioxide. The above 21-hydroxy-21-methyl steroids and their 21-acylates, which are stated to have adrenocortical activity, may be formulated as pharmaceutical compositions in admixture with suitable carriers. Specification 870,390 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US399660A | 1960-01-22 | 1960-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB902373A true GB902373A (en) | 1962-08-01 |
Family
ID=21708610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10624/60A Expired GB902373A (en) | 1960-01-22 | 1960-03-25 | Steroids and preparation thereof |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE589604A (en) |
| FR (1) | FR370M (en) |
| GB (1) | GB902373A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007823A2 (en) * | 1978-07-13 | 1980-02-06 | Roussel-Uclaf | 3,20-Dioxo-4,9-diene-21-hydroxy-steroid compounds, process for their preparation, their use in medicines and pharmaceutical compositions containing them |
-
1960
- 1960-03-25 GB GB10624/60A patent/GB902373A/en not_active Expired
- 1960-04-11 BE BE589604A patent/BE589604A/en unknown
- 1960-08-29 FR FR837045A patent/FR370M/en active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007823A2 (en) * | 1978-07-13 | 1980-02-06 | Roussel-Uclaf | 3,20-Dioxo-4,9-diene-21-hydroxy-steroid compounds, process for their preparation, their use in medicines and pharmaceutical compositions containing them |
| FR2430953A1 (en) * | 1978-07-13 | 1980-02-08 | Roussel Uclaf | NOVEL 3,20-DIOXO 4,9-DIENE 21-HYDROXYL DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICAMENTS |
| EP0007823A3 (en) * | 1978-07-13 | 1980-05-14 | Roussel-Uclaf | 3,20-dioxo-4,9-diene-21-hydroxy-steroid compounds, process for their preparation, their use in medicines and pharmaceutical compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| BE589604A (en) | 1960-08-01 |
| FR370M (en) | 1961-04-04 |
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