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GB956273A - Improvements in or relating to the preparation of steroid compounds - Google Patents

Improvements in or relating to the preparation of steroid compounds

Info

Publication number
GB956273A
GB956273A GB2396260A GB2396260A GB956273A GB 956273 A GB956273 A GB 956273A GB 2396260 A GB2396260 A GB 2396260A GB 2396260 A GB2396260 A GB 2396260A GB 956273 A GB956273 A GB 956273A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
methyl
acetoxy
methylene
keto
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
GB2396260A
Inventor
Gordon Hanley Phillipps
William Graham
Gordon Ian Gregory
Joseph Elks
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.)
Glaxo Group Ltd
Original Assignee
Glaxo Group Ltd
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 Glaxo Group Ltd filed Critical Glaxo Group Ltd
Priority to GB2396260A priority Critical patent/GB956273A/en
Publication of GB956273A publication Critical patent/GB956273A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • 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)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 3b , 17a -dihydroxy -16- methylene -5a - pregn-9(11)-en -20- one, its 3-acetate, 3b -acetoxy-9a , 11b -dichloro -17a -hydroxy -16- methylene -5a - pregnan -20- one, 3b , 17a - dihydroxy -16b - methyl -5a - pregn-9 -20- one and its 3-acetate, together with a process for the preparation of 16b -methyl-17a -hydroxy hydroxy -20- keto -5a - steroids by subjecting a 16, 17-epoxy -16b -methyl -20- keto-steroid of the 5a -series to rearrangement in a solvent medium in the presence of an acid catalyst to form a 17a -hydroxy -16- methylene -20-keto- or 17a -hydroxy -16- methyl -D 15 -20- keto-steroid, or a mixture thereof, which product is then hydrogenated in the presence of a platinum or Raney nickel catalyst. The process is especially applicable to compounds of the general formula: <FORM:0956273/C2/1> in which R is hydrogen or acyl, X is keto, acyloxy, hydroxy or halogen, Y is hydrogen or halogen, or X and Y together signify a carbon-carbon double bond. The acid catalyst is preferably a strong acid (HBr, H2SO4, HClO4, HCO2H), and the rearrangement is preferably effected in a solvent medium of low ionising power e.g. an ether, thereby yielding mainly 16-methylene steroids, which give the 16b -methyl epimer on hydrogenation with platinum or nickel. Examples detail the conversion of 3b -acetoxy -16- methyl -5a - pregna-9(11), 16-dien -20- one into 3b -acetoxy -17a - hydroxy -16b - methyl -5a - pregn-9(11)-en -20- one, and the preparation of 3b -acetoxy -17a - hydroxy -16- methylene -5a -pregnane-11, 20-dione, 3b -acetoxy-9a , 11b -dichloro-17a -hydroxy -16- methylene -5a -pregnan -20- one, 9a , 11b - dichloro-3b , 17a -dihydroxy -16b - methyl -5a - pregnan -20- one and 3b -acetoxy -17a - hydroxy -16b - methyl-5a -pregnane-11, 20-dione under various conditions. Specifications 805,497 and 956,272 also are referred to.
GB2396260A 1959-07-20 1959-07-20 Improvements in or relating to the preparation of steroid compounds Expired GB956273A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2396260A GB956273A (en) 1959-07-20 1959-07-20 Improvements in or relating to the preparation of steroid compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2396260A GB956273A (en) 1959-07-20 1959-07-20 Improvements in or relating to the preparation of steroid compounds

Publications (1)

Publication Number Publication Date
GB956273A true GB956273A (en) 1964-04-22

Family

ID=10204186

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2396260A Expired GB956273A (en) 1959-07-20 1959-07-20 Improvements in or relating to the preparation of steroid compounds

Country Status (1)

Country Link
GB (1) GB956273A (en)

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