GB865673A - 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
GB865673A
GB865673A GB34618/57A GB3461857A GB865673A GB 865673 A GB865673 A GB 865673A GB 34618/57 A GB34618/57 A GB 34618/57A GB 3461857 A GB3461857 A GB 3461857A GB 865673 A GB865673 A GB 865673A
Authority
GB
United Kingdom
Prior art keywords
compound
pregnene
lower alkyl
trihydroxy
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
Application number
GB34618/57A
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 GB865673A publication Critical patent/GB865673A/en
Expired legal-status Critical Current

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds having the formula: <FORM:0865673/IV (b)/1> wherein R is hydrogen or the acyl radical of a hydrocarbon carboxylic acid containing 1-12 carbon atoms, R1 is an 11b -hydroxy or keto group and X is fluorine, chlorine, bromine, or iodine and a process for the production of a 3-keto-7-lower alkyl-D 4-cyclopentanophenanthrene compound which comprises reacting a 3-keto-D 4,6-compound otherwise unsubstituted in A and B rings with a lower alkyl Grignard compound in the presence of a cuprous chloride catalyst, the amount of Grignard reagent being in substantial molar excess of the steroid reactant. As Grignard reagent there may be used methyl magnesium bromide. 7-lower alkyl-11b , 21-dihydroxy-4, 17(20)-pregnadiene-3-one or a 21-acylate thereof is oxidatively hydroxylated e.g. with osmium tetroxide and an oxidising agent to obtain a 7-lower alkyl-11b , 17a , 21-trihydroxy-4-pregnene-3, 20-dione, which may be oxidised to form the corresponding 11-keto compound. Alternatively the 11-hydroxy compound may be dehydrated to obtain 7-lower alkyl-11b , 17a , 21-trihydroxy-4 9(11)-pregnadiene-3, 20-dione, 21 acylate which is reacted with Nbromoacetamide to obtain the corresponding 9a -bromo compound. The 9a -bromo compound on treatment with potassium acetate gives a 9, 11b -oxido compound which with hydrogen fluoride gives 9a -fluoro-11b , 17a , 21- trihydroxy-4- pregnene-3, 20- dione. Illustrative products of the invention are 7methyl-11b , 17a , 21-trihydroxy-4-pregnene-3, 20-dione, 7-methyl-17a , 21-dihydroxy-4-pregnene-3, 11, 20-trione, 7-methyl-9a -fluoro-11b , 17a , 21-trihydroxy-4-pregnene-4, 17(20)-[cis]-pregnadiene-3-one and the 21-acetates thereof. Specification 749.201 is referred to.ALSO:Pharmaceutical compositions incorporating 7-lower alkyl - 11b , 17a , 21 - trihydroxy - 4 - pregnene - 3,20 - diene and 7 - lower alkyl - 17a ,21-dihydroxy - 4 - pregnene - 3,11,20 - trione and their 21-esters are employed in ointments, creams, lotions and sprays. Antibiotics such as penicillins, neomycin, tetracycline and chloramphenicol may also be present. Specification 749,201 is referred to.
GB34618/57A 1956-12-10 1957-11-06 Improvements in or relating to steroids and the manufacture thereof Expired GB865673A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US865673XA 1956-12-10 1956-12-10

Publications (1)

Publication Number Publication Date
GB865673A true GB865673A (en) 1961-04-19

Family

ID=22199419

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34618/57A Expired GB865673A (en) 1956-12-10 1957-11-06 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB865673A (en)

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