IL26917A - Process for the production of 6alpha-fluoro-16-methylene-17alpha-hydroxy steroids of the pregnane series - Google Patents
Process for the production of 6alpha-fluoro-16-methylene-17alpha-hydroxy steroids of the pregnane seriesInfo
- Publication number
- IL26917A IL26917A IL2691766A IL2691766A IL26917A IL 26917 A IL26917 A IL 26917A IL 2691766 A IL2691766 A IL 2691766A IL 2691766 A IL2691766 A IL 2691766A IL 26917 A IL26917 A IL 26917A
- Authority
- IL
- Israel
- Prior art keywords
- methylene
- steroids
- 6alpha
- 17alpha
- fluoro
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
C O H E N Z E D E K S P I S B A C H R PATE N T A TT OR N EYS LEVONTIN ST 1169 T E L A V V P A T E N T S D E S I G N S O R D I N A N C E SPECIFICATION PROCESS FOR THE OF STEROIDS OF THE PREGNANE SERIES a German of 61 HEREBY DECLARE the nature of this invention and in what manner fhe same is to be performed to be particularly described and ascertained in and by the following present invention is concerned with a process for the production of steroids of the pregnane It is that steroids can be prepared by dehydrating and but when this reaction is applied to steroids substituted in particularly steroids of the pregnane it has been found that the yields obtained are very Considerable practical difficulties been encountered in preparation of steroids of the pregnane have now found that the yields in this reaction stage in the preparation of steroids of the pregnane series can be Improved by ing out the reaction on a and then the product if to obtain the ponding According to the present a process for the preparation of ids of the formula wherein is OH or any and is or an acetyl by dehydrating and a in the steroid corresponding to the desired product is used as the starting material and the group in the product obtained is if The reaction itself is effected under the usual and isomerization ditions for the steroids to form suitable reaction conditions are described in detail for German Specificat ons and and British Specification Chlorinated preferably or glacial acetic in be used as reaction The normal cedure is to introduce dry hydrogen chloride in gaseous form into the reaction mixture in an amount up to that which gives saturated The reaction temperature is suitably between about and room The reaction normally takes about 6 to 48 If the reaction product obtained after dehydration may be saponified to form the Standard procedures can also be used for this for example saponification with raethanolic sodium hydroxide solution or with alkali metal carbonate or alkali metal for practical the group will always be converted into a other acyl for example propionyl or acyl radicals may also be acyloxy acylox in and may be any desired usual steroid try for are preferably but acyloxy and substituted groups containing up to 18 carbon atoms and the sulphates or phosphates may be have carried out comparative tests and have for that the conversion of to gives yields of only about 10 to Under the same reaction on the other yields of at least are obtained when the corresponding is used as the starting material the reaction in this reaction subsequent hydrolysis to effect saponification of the group is included in the calculation of the It must be in that the isolation of the desired product from a reaction mixture only 10 to 1 of the desired product is much more expensive and time consuming than working up a mixture containing or more of the desired It could not be foreseen from the published literature that the intermediate protection of the hydroxy group would give rise to such an improvement in the steroids of Formula are valuable intermediate products for the preparation of a wide pregnadiene pregnadiene 11β nisone and In order that the invention be more fully the following examples are given by way of tration E ample 1 Dry hydrogen chloride was introduced at into a solution of 10 g of in 600 ml of chloroform to form a saturated The mixture was allowed to stand overnight and the chloroform solution was then first with then with aqueous sodium hydrogen carbonate and again with dried over sodium sulphate and evaporated until A total of g of of was crystallized from A sample reerystallized from ether melted at A solution of g of in 125 ml of methanol was heated at reflux temperature for 10 minutes with ml of aqueous sodium hydroxide solution under a nitrogen After the solution had it was neutralized with ml of sulphuric acid being then diluted with 250 ml of g of of were A sample recrystallized from acetone melted at λ cm Example 2 20 g of dry hydrogen chloride were introduced with stirring at into a suspension of g of in ml of glacial acetic The reaction mixture was stirred at room temperature for 18 then poured into 2 of water and suction The crude of was dissolved hot in 1 of the solution was treated with 2 g of filtered and g of of the were A 201 tallized from melted at g of progesterone were reacted as in Example in 220 ml of methanol with 36 ml of sodium hydroxide solution to form g of of A sample recrystallized from acetone had an of Example Dry hydrogen chloride was introduced to saturation 400 ml of absolute After the mixture had been allowed to stand for 18 it was washed in succession with aqueous sodium hydrogen carbonate solution and dried over sodium sulphate and concentrated until dry at a reduced The residue was treated as in Example in 120 ml of methanol with 40 of I sodium hydroxide solution and then worked Recrystallization from acetone yielded g of of Reichstein Substance A pure sample of the substance melted at insufficientOCRQuality
Claims (1)
1. Claim 1 whenever used in the tion of and DATED THIS 20th day of 1966 O Box Tel Aviv Attorneys for Applicants insufficientOCRQuality
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEM0067768 | 1965-12-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
IL26917A true IL26917A (en) | 1970-07-19 |
Family
ID=7312330
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL2691766A IL26917A (en) | 1965-12-23 | 1966-11-23 | Process for the production of 6alpha-fluoro-16-methylene-17alpha-hydroxy steroids of the pregnane series |
Country Status (9)
Country | Link |
---|---|
BE (1) | BE691655A (en) |
CH (1) | CH476704A (en) |
DE (1) | DE1543256A1 (en) |
ES (1) | ES334816A1 (en) |
FR (1) | FR1505675A (en) |
GB (1) | GB1127167A (en) |
IL (1) | IL26917A (en) |
NL (1) | NL6615761A (en) |
SE (1) | SE304003B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4599463A (en) * | 1984-12-24 | 1986-07-08 | General Electric Company | Process for the preparation of bisphenols |
-
1965
- 1965-12-23 DE DE19651543256 patent/DE1543256A1/en active Pending
-
1966
- 1966-10-10 CH CH1458566A patent/CH476704A/en not_active IP Right Cessation
- 1966-11-08 NL NL6615761A patent/NL6615761A/xx unknown
- 1966-11-18 GB GB5173866A patent/GB1127167A/en not_active Expired
- 1966-11-23 IL IL2691766A patent/IL26917A/en unknown
- 1966-12-08 FR FR86634A patent/FR1505675A/en not_active Expired
- 1966-12-21 SE SE1749866A patent/SE304003B/xx unknown
- 1966-12-22 ES ES334816A patent/ES334816A1/en not_active Expired
- 1966-12-22 BE BE691655D patent/BE691655A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
BE691655A (en) | 1967-06-22 |
DE1543256A1 (en) | 1969-09-11 |
NL6615761A (en) | 1967-06-26 |
FR1505675A (en) | 1967-12-15 |
SE304003B (en) | 1968-09-16 |
GB1127167A (en) | 1968-09-11 |
ES334816A1 (en) | 1968-03-01 |
CH476704A (en) | 1969-08-15 |
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