GB836974A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Improvements in or relating to steroids and the manufacture thereof

Info

Publication number
GB836974A
GB836974A GB36231/58A GB3623158A GB836974A GB 836974 A GB836974 A GB 836974A GB 36231/58 A GB36231/58 A GB 36231/58A GB 3623158 A GB3623158 A GB 3623158A GB 836974 A GB836974 A GB 836974A
Authority
GB
United Kingdom
Prior art keywords
pregnadiene
dihydroxy
carbon atoms
lower alkyl
sulphate
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
Application number
GB36231/58A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Upjohn Co filed Critical Upjohn Co
Publication of GB836974A publication Critical patent/GB836974A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J5/00Normal 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J75/00Processes for the preparation of steroids in general

Abstract

The invention comprises a compound having the general formula <FORM:0836974/IV (b)/1> wherein R is hydrogen or the acyl radical of a hydrocarbon carboxylic acid containing from 1-8 carbon atoms inclusive, R1 is a lower alkyl radical containing from 1-8 carbon atoms inclusive and X is fluorine, chlorine, bromine or iodine and a process for the preparation thereof which comprises oxidizing a 2-lower alkyl-9a -halo - 11b ,17a - dihydroxy - 21 - acyloxy - 4,6-pregnadiene-3,20-dione with chromic acid. The 21-ester may be hydrolysed with sodium bicarbonate in ethanol to obtain 2-lower alkyl-9b -halo - 17a ,21 - dihydroxy - 4,6 - pregnadiene-3,11,20-trione. Examples describe the preparation of 2 - methyl - 9a - fluoro - 17a ,21 - dihydroxy - 4,6 - pregnadiene - 3,11,20 - trione-21-acetate, the corresponding 9a -bromo compound, the free triol, 2-ethyl-9a -chloro-17a ,21-dihydroxy - 4,6 - pregnadiene - 3,11,20 - trione-21-acetate and of compounds bearing in 2-position methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, heptyl, p octyl, phenyl or benzyl and in which the 21-acylate may be acetate, propionate, butyrate, benzoate, valerate, hexanoate, phenylpropionate, phenylacetate, anisate or nicotinate. Specification 836,973 also is referred to.ALSO:Compounds having the general formula <FORM:0836974/VI/1> wherein R is hydrogen or the acyl radical of a hydrocarbon carboxylic acid containing from 1-8 carbon atoms inclusive, R1 is a lower alkyl radical containing from 1-8 carbon atoms, and X is fluorine, chlorine, bromine or iodine, are valuable for topical use and employed in dermatological and ophthalmic ointments or therapeutic dentifrices. Additionally there may be present in the ointment antibiotics such as neomycin sulphate, bacitracin, circulin, polymyxin B sulphate, gramicidin, streptomycin sulphate, dihydrostreptomycin sulphate, oxytetracycline, chlortetracycline, tetracycline, and chloramphenicol. Sulphonamides may also be present. Specification 836,973 also is referred to.
GB36231/58A 1956-03-29 1957-02-06 Improvements in or relating to steroids and the manufacture thereof Expired GB836974A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US836974XA 1956-03-29 1956-03-29

Publications (1)

Publication Number Publication Date
GB836974A true GB836974A (en) 1960-06-09

Family

ID=22180086

Family Applications (1)

Application Number Title Priority Date Filing Date
GB36231/58A Expired GB836974A (en) 1956-03-29 1957-02-06 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB836974A (en)

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