GB946576A - Improvements in or relating to steroids - Google Patents
Improvements in or relating to steroidsInfo
- Publication number
- GB946576A GB946576A GB43596/60A GB4359660A GB946576A GB 946576 A GB946576 A GB 946576A GB 43596/60 A GB43596/60 A GB 43596/60A GB 4359660 A GB4359660 A GB 4359660A GB 946576 A GB946576 A GB 946576A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- oso2r11
- opo3h2
- fluorine
- representing
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Abstract
The invention comprises a compound having the formula: <FORM:0946576/C2/1> wherein A 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, X represents <FORM:0946576/C2/2> or <FORM:0946576/C2/3> , R being attached at the 2-position and representing hydrogen or methyl, Z represents hydrogen methyl or fluorine and Hal represents chlorine, fluorine, bromine or iodine provided that 1/. when A represents OPO3H2 or OSO2R11 Hal represents fluorine and 2/. when X represents -CH=CH-, Z represents methyl or fluorine and processes for the preparation thereof by dehydrating a compound having the formula: <FORM:0946576/C2/4> wherein Ac, X, and Z are as above defined, hypohalogenating to form the corresponding 9a -chloro,bromo or iodo derivative and then if desired epoxidising to produce a compound having the general formula: <FORM:0946576/C2/5> wherein Ac, X and Z are as above defined, 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 oxidising or hydrolysing 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-OSO2 R11 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-bromacetamide and anhydrous sulphur dioxide, the hypohalogenation step with perchloric acid and N-bromoacetamide or N-iodo-succinimide, the epoxidation step with anhydrous potassium acetate and the oxidation step with chromic acid. In an alternative process the 21-phosphate is obtained by treating the 21-sulphonate with phosphoric acid in the presence of a tertiary amine and then acidifying the 21-hydrogen phosphate so produced to obtain the free 21-phosphate compound. Specifications 850,833, 872,112, 873,219, 946,578 and 946,579 are referred to.ALSO:Pharmaceutic compositions having anti-inflammatory activity and containing a compound of the formula: <FORM:0946576/A5-A6/1> wherein A represents -OH, -OPO3H2, -OSO2R11 wherein R11 is an alkyl or aryl radical (1-10 carbon atoms) or -OAc, the term Ac representing the acyl radical of an organic carboxylic acid particularly a hydrocarbon carboxylic acid having 1-12 carbon atoms, R1 represents b -OH or Keto, X represents <FORM:0946576/A5-A6/2> or <FORM:0946576/A5-A6/3> , R being attached at the 2-position and representing H or CH3, 2 represents H, CH3, or F and Hal represents halogen provided that: (1) when A represents -OPO3H2 or -OSO2R11 Hal represents fluorine; and (2) when X represents -CH = CH-, Z represents CH3 or F, and a coacting antibiotic, are administered orally as pills, tablets, capsules, syrups or elixirs, in liquid forms for injectable products, or topically as ointments, creams or lotions. Specifications 850,833, 872,112, 873,219, 946,578 and 946,579 are referred to.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US144960A | 1960-01-11 | 1960-01-11 | |
US3676060A | 1960-06-17 | 1960-06-17 | |
US51298A US3239544A (en) | 1960-08-23 | 1960-08-23 | 16-fluoro-11-hydroxy steroids of the pregnane series |
Publications (1)
Publication Number | Publication Date |
---|---|
GB946576A true GB946576A (en) | 1964-01-15 |
Family
ID=27356927
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB43596/60A Expired GB946576A (en) | 1960-01-11 | 1960-12-19 | Improvements in or relating to steroids |
GB38029/62A Expired GB946579A (en) | 1960-01-11 | 1960-12-19 | Improvements in or relating to steroids and the manufacture thereof |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB38029/62A Expired GB946579A (en) | 1960-01-11 | 1960-12-19 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE598999A (en) |
CH (2) | CH407113A (en) |
FR (1) | FR1088M (en) |
GB (2) | GB946576A (en) |
-
1960
- 1960-12-19 GB GB43596/60A patent/GB946576A/en not_active Expired
- 1960-12-19 GB GB38029/62A patent/GB946579A/en not_active Expired
-
1961
- 1961-01-09 CH CH18261A patent/CH407113A/en unknown
- 1961-01-09 CH CH940665A patent/CH422774A/en unknown
- 1961-01-11 BE BE598999A patent/BE598999A/en unknown
- 1961-04-08 FR FR858158A patent/FR1088M/en active Active
Also Published As
Publication number | Publication date |
---|---|
GB946579A (en) | 1964-01-15 |
FR1088M (en) | 1962-01-29 |
CH422774A (en) | 1966-10-31 |
CH407113A (en) | 1966-02-15 |
BE598999A (en) | 1961-07-11 |
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