GB863777A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB863777A GB863777A GB24575/57A GB2457557A GB863777A GB 863777 A GB863777 A GB 863777A GB 24575/57 A GB24575/57 A GB 24575/57A GB 2457557 A GB2457557 A GB 2457557A GB 863777 A GB863777 A GB 863777A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fluoro
- methyl
- acid
- pregnene
- dione
- 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
- 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)
Abstract
The invention comprises a steroid compound having the formula: <FORM:0863777/IV (b)/1> wherein R is a alkyl or aryl radical and R1 is a hydroxy or keto group, a process for the preparation thereof which comprises dehalogenating the corresponding 6-alkyl or 6-aryl-21-iodo-pregnene to obtain 6-methyl-9a -fluoro-11b , 17a - dihydroxy- 4- pregnene- 3, 20- dione and if desired oxidising the 11-hydroxy group if present to an 11-keto group. The dehalogenation may be effected by a reducing agent such as zinc dust and acetic acid, sodium or potassium thiosulphate or sodium bisulphate. In preparing the 21-iodo compound 9a -fluoro-6-methyl hydrocortisone is treated with the acid halide of an organic sulphonic acid such as methanesulphonic acid, ethanesulphonic acid, propanesulphonic acid, benzenesulphonic acid, p-toluenesulphonic acid and a or b -naphthanesulphonic acids, in a solvent to produce a 6- methyl- 9a - fluoro- 11b , 17a , 21-trihydroxy-4-pregnene-3, 20-dione 21-alkyl or arylsulphonate, which is reacted directly with sodium or potassium iodide in acetone solution. In the iodination step a molar excess of sodium iodide is preferred. The 6-methyl-9a -fluoro- 11b , 17a - dihydroxy- 4- pregnene- 3, 20 dione may be oxidised to the corresponding 6-methyl-9a -fluoro- 17a -hydroxy-4-pregnene-3, 11, 20-trione in acetic acid solution with chromic anhydride or with a halo amide or imide of an acid e.g. n-bromoacetamide, N-chlorosuccimide or nbromosuccimide. Examples describe the preparation of 6a -methyl- 9a - fluoro- 11b - 17a - dihydroxy- 4-pregnene-3, 20-dione, 6a -methyl-9a -fluoro-17a -hydroxy-3, 11, 20 trione and other 6-substituted steroids. Specification 863,782 is referred to.ALSO:Steroid compounds having the formula <FORM:0863777/VI/1> wherein R is an alkyl or aryl radical and R1 is a hydroxy or keto group are employed in oral, parenteral and topical compositions. The topical compositions may take the form of ointments, lotions, jellies, creams, suppositories, bougies and aqueous suspensions. A dermatological and ophthalmic ointment incorporating 6a - methyl - 9a - fluoro - 11b ,17a - dihydroxy - 4 - pregnene - 3,20 - dione may also contain antibiotics such as neomycin sulphate, bacitracin, circulin, polymyxin B sulphate, gramicidin, streptomycin sulphate, dihydrostreptomycin sulphate, oxytetracycline, chlorotetracycline, tetracycline and chloramphenicol, and the sulphonamides. Specification 863,782 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US863777XA | 1956-09-10 | 1956-09-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB863777A true GB863777A (en) | 1961-03-29 |
Family
ID=22198167
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB24575/57A Expired GB863777A (en) | 1956-09-10 | 1957-08-02 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB863777A (en) |
-
1957
- 1957-08-02 GB GB24575/57A patent/GB863777A/en not_active Expired
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