GB915635A - Steroids and processes for their manufacture - Google Patents
Steroids and processes for their manufactureInfo
- Publication number
- GB915635A GB915635A GB9186/59A GB918659A GB915635A GB 915635 A GB915635 A GB 915635A GB 9186/59 A GB9186/59 A GB 9186/59A GB 918659 A GB918659 A GB 918659A GB 915635 A GB915635 A GB 915635A
- Authority
- GB
- United Kingdom
- Prior art keywords
- steroids
- keto
- hydroxy
- alkyl
- oxo
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- 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 3-keto-D 1,5-steroids of the androstane and pregnane series particularly of the general formula <FORM:0915635/IV (b)/1> wherein X represents a hydrogen, fluorine, chlorine or bromine atom, Y is H2, (H, OH) or O, Z represents hydrogen or an alkyl group containing less than 6 carbon atoms, and T represents O, (H, b -OR), (alkyl having less than 6 carbon atoms, b -OR), (ethinyl, b -OR) or (CH2VCO, a W), W being H or OH, V being H or OR, and R representing hydrogen or the acyl residue of a carboxylic acid having up to 12 carbon atoms, and a process for the preparation of 3-keto-D 5-steroids such as 3-keto-D 1,5-steroids by reacting 3-keto-D -4-steroids such as 3-keto-D 1,4-steroids having at the 6-position a chlorine, bromine or iodine atom or a lower aliphatic acyloxy or an aliphatic or aromatic sulphonyloxy group with a polyvalent reducing metal in a predominantly organic solvent medium, the reaction mixture being substantially neutral. By "polyvalent reducing metal" is meant a metal which has an electrode potential between -0.15 and -2.5 volts, e.g. cadmium, cobalt, nickel, tin, magnesium, aluminium, zinc, chromium and iron. Particularly useful metals are magnesium, zinc and aluminium amalgam. Reaction solvents that may be used are preferably solvents capable of supplying a proton such as alcohols, but other organic solvents, e.g., a moist ether such as tetrahydrofuran or ethylether may be used. In the above process the steroid reactants may be of the androstane, pregnane, saponin, sapogenin or bile acid series. These reactants may contain any of the following substituents:- 2-methyl, 6-methyl, 9a -halogeno, 11-hydroxy, 11-oxo, 16-alkyl, 16-hydroxy, 17-oxo, 17-hydroxy, 20-oxo, 21-halogeno, and 21-hydroxy, esters of the aforementioned hydroxy groups, oxido such as 9b ,11b -oxido, 17-alkyl and 17-alkynyl. Ester groups present in the steroid reactants may subsequently be hydrolysed either chemically using dilute acid or microbiologically using the microorganisms Flavobacterium dehydrogenans. Specifications 796,769, 832,325, 901,021 and 915,636 are referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72552158A | 1958-04-01 | 1958-04-01 | |
| US770315A US3013033A (en) | 1958-10-29 | 1958-10-29 | Novel alkylated pregnadienes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB915635A true GB915635A (en) | 1963-01-16 |
Family
ID=27111165
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3606/61A Expired GB915636A (en) | 1958-04-01 | 1959-03-17 | Novel alkylated pregnadienes |
| GB9186/59A Expired GB915635A (en) | 1958-04-01 | 1959-03-17 | Steroids and processes for their manufacture |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3606/61A Expired GB915636A (en) | 1958-04-01 | 1959-03-17 | Novel alkylated pregnadienes |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH386417A (en) |
| FR (1) | FR311M (en) |
| GB (2) | GB915636A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0737433B2 (en) * | 1987-06-11 | 1995-04-26 | 協和醗酵工業株式会社 | Method for producing 7-amino-6-demethyl-6-deoxytetracycline |
-
1959
- 1959-03-17 GB GB3606/61A patent/GB915636A/en not_active Expired
- 1959-03-17 GB GB9186/59A patent/GB915635A/en not_active Expired
- 1959-03-31 CH CH7138959A patent/CH386417A/en unknown
-
1960
- 1960-08-25 FR FR836727A patent/FR311M/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| GB915636A (en) | 1963-01-16 |
| FR311M (en) | 1961-03-20 |
| CH386417A (en) | 1965-01-15 |
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