GB946577A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB946577A GB946577A GB3802762A GB3802762A GB946577A GB 946577 A GB946577 A GB 946577A GB 3802762 A GB3802762 A GB 3802762A GB 3802762 A GB3802762 A GB 3802762A GB 946577 A GB946577 A GB 946577A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- oso2r11
- hydroxy
- opo3h2
- acyl
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises a compound having the formula: <FORM:0946577/C2/1> wherein R represents hydroxyl, -OPO3H2, -OSO2R11 wherein R11 is an alkyl or aryl radical or O Acyl the term Acyl representing the acyl radical of an organic carboxylic acid, R1 represents a b -hydroxy or keto group and Hal represents chlorine, bromine, fluorine or iodine, provided that when R represents -OPO3H2 or -OSO2R11 Hal represents fluorine, and a process for the preparation thereof by dehydrating a 16-halo-1-dehydrocortisone 21-acylate to produce a 16-halo-17a -hydroxy-21-acyloxy-1,4,9(11)-pregnatriene-3, 20-dione, hypohalogenating to form the corresponding 9a -chloro, bromo or iodo derivative and then if desired epoxidizing to produce a 16-halo-9b ,11b -oxido-17a -hydroxy-21-acyloxy-1, 4-pregnadiene-3,20-dione and then reacting this latter compound with aqueous hydrogen fluoride or aqueous hydrogen chloride to form the corresponding 9a -fluoro- or 9a -chloro derivative, and then if desired oxidizing and/or hydrolyzing to produce the corresponding 11-keto 21-ester or free 21-hydroxy compound, subsequently the 21-hydroxy compound may be treated with an alkyl or aryl sulphonyl halide to obtain a 21-OSO2R11 compound, which may be treated with an alkali metal iodide to obtain a 21-iodo compound or silver dihydrogen phosphate to obtain a 21-OPO3H2 compound; treating the 21-OSO2R11 compound or the 21-iodo compound with a metal fluoride produces the 21-fluoro compounds. In the process above the dehydration step may be effected with N-bromoacetamide and anhydrous sulphur dioxide, the hypohalogenation step with perchloric acid and N-bromoacetamide or N-iodosuccinimide, the epoxidation step with anhydrous potassium acetate and the oxidation step with chromic acid. Specifications 850,833, 872,112, 873,219 and 946,578 also are referred to.ALSO:Pharmaceutical compositions, having anti-inflammatory and glucocorticoid activity and containing a compound having the formula: <FORM:0946577/A5-A6/1> wherein R represents hydroxyl -OPO3H2 -OSO2R11 wherein R11 is an alkyl or aryl radical or O Acyl, the term acyl representing the acryl radical or an organic carboxylic acid, R1 represents a b -hydroxy group or keto group and Hal represents chlorine, bromine, fluorine or iodine provided that when R represents -OPO3H2 or -OSO2R11, Hal represents fluorine, and, if desired, a coacting antibiotic or germicide, are administered orally in pills, tablets, capsules, syrups or elixirs, parenterally in liquid injectable products, or topically in ointments, creams and lotions. Specifications 850,833, 872,112, 873,219 and 946,578 also are referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3802762A GB946577A (en) | 1960-12-19 | 1960-12-19 | Improvements in or relating to steroids and the manufacture thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3802762A GB946577A (en) | 1960-12-19 | 1960-12-19 | Improvements in or relating to steroids and the manufacture thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
GB946577A true GB946577A (en) | 1964-01-15 |
Family
ID=10400685
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3802762A Expired GB946577A (en) | 1960-12-19 | 1960-12-19 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB946577A (en) |
-
1960
- 1960-12-19 GB GB3802762A patent/GB946577A/en not_active Expired
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