GB810859A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB810859A GB810859A GB34036/56A GB3403656A GB810859A GB 810859 A GB810859 A GB 810859A GB 34036/56 A GB34036/56 A GB 34036/56A GB 3403656 A GB3403656 A GB 3403656A GB 810859 A GB810859 A GB 810859A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pregnene
- dione
- hydroxy
- methyl
- lower alkyl
- 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)
Abstract
The invention comprises 2-lower alkyl-11-oxygenated - 17a - hydroxy - 4 - pregnene - 3,20-diones having the general formula: <FORM:0810859/IV (b)/1> wherein R is hydrogen or fluorine, chlorine, bromine or iodine, R1 is a hydroxy or keto group and the lower alkyl radical contains from 1-8 carbon atoms inclusive, and a process for the preparation thereof which comprises treating a compound having the general formula: <FORM:0810859/IV (b)/2> wherein R, R1 and lower alkyl are as defined above, with an organic acid sulphonyl chloride selected from the group consisting of toluenesulphonyl chloride, benzenesulphonyl chloride, methanesulphonyl chloride, naphthylsulphonyl chloride to give the corresponding 11-oxygenated - 2 - lower alkyl - 17a - hydroxy - 21 - organic acid sulphonyloxy - 4 - pregnene - 3,20-dione; heating the latter compound in acetone solution with an alkali metal iodide to obtain the corresponding 11-oxygenated 2-lower alkyl-17a - hydroxy - 21 - iodo - 4 - pregnene - 3,20-dione and treating the thus obtained 21-iodo steroid with a reducing agent selected from the group consisting of zinc dust and acetic acid, an alkali metal thiosulphate, an alkali metal sulphite and an alkali metal hydrosulphite to give the corresponding 11-oxygenated 2-lower alkyl - 17a - hydroxy - 4 - pregnene - 3,20 - dione. The 11-hydroxy compounds may be converted to 11-keto compounds by chromic acid oxidation either as the first step before hydrolysis or as the last step. For the reduction there may be used sodium or potassium sulphite, sodium or potassium hydrosulphite or sodium or potassium thiosulphate. Examples disclose the production of 2-methyl-11b ,17a -dihydroxy - 4 - pregnene - 3,20 - dione, 2 - methyl - 9a - fluoro - 11b ,17a - dihydroxy - 4 - pregnene - 3,20 - dione, 2 - ethyl - 11b ,17a -dihydroxy - 4 - pregnene - 3,20 - dione, 2 - methyl - 9a - fluoro - 4 - pregnene - 3,11,20 - trione, 2 - methyl - and 2 - ethyl - 17a - 2 - methyl - 9a - chloro - and 9a - fluoro - 17a -hydroxy - 4 - pregnene - 3,11,20 - trione, 2-methyl - 11b ,17a - diacetoxy - 4 - pregnene - 3,20-dione, and other 17a -mono- and 11b ,17a -diesters of 2-alkyl-11-oxygenated-17a -hydroxy-4-pregnene-3,20-diones. Specifications 794,484, 794,485 and 794,489 are referred to.ALSO:2 - Lower alkyl - 11b ,17a - dihydroxy - 4-pregnene - 3,20 - diones and 2 - lower alkyl-17a - hydroxy - 4 - pregnene - 3,11,20 - triones are used in oral compositions as well as in topical applications. Orally they may be employed as tablets using polyethylene glycol 4000 or 6000 as a carrier or lactose and/or sucrose and a diluent. For topical use these compounds and their 9a -halo derivatives may be used as ointments, jellies, creams and aqueous suspensions. A dermatological and ophthalmic ointment comprises wool fat, mineral oil, 2-methyl-11b ,17a -dihydroxy-4-pregnene-3,20-dione and white petrolatum. An ointment incorporating an antibiotic comprises wool fat, mineral oil, neomycin sulphate, 2-methyl - 9a - fluoro - 11b ,17a - dihydroxy - 4-pregnene - 3,20 - dione and white petrolatum. In place of, or in addition to, neomycin sulphate other antibiotics such as bacitracin, circulin, polymyxin B sulphate, gramicidin, streptomycin sulphate, dihydrostreptomycin sulphate, oxytetracycline, chlorotetracycline, tetracycline, chloramphenicol and the sulphonamides can be employed. Specifications 794,484, 794,485 and 794,489, [Group IV (b)], are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US810859XA | 1955-11-16 | 1955-11-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB810859A true GB810859A (en) | 1959-03-25 |
Family
ID=22162015
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB34036/56A Expired GB810859A (en) | 1955-11-16 | 1956-11-07 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB810859A (en) |
-
1956
- 1956-11-07 GB GB34036/56A patent/GB810859A/en not_active Expired
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