GB931224A - Steroid compounds and their production - Google Patents

Steroid compounds and their production

Info

Publication number
GB931224A
GB931224A GB1344363A GB1344363A GB931224A GB 931224 A GB931224 A GB 931224A GB 1344363 A GB1344363 A GB 1344363A GB 1344363 A GB1344363 A GB 1344363A GB 931224 A GB931224 A GB 931224A
Authority
GB
United Kingdom
Prior art keywords
bismethylenedioxy
ethylenedioxy
methyl
keto
allopregnane
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
GB1344363A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB931224A publication Critical patent/GB931224A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 3,6,11-triketo-16b -methyl-17(20), 20(21)-bismethylenedioxy-allo-pregnane and the corresponding 3-ethylene-dioxy compound, 3-ethylenedioxy-6b -hydroxy-6a ,16b -dimethyl-17(20), 20(21)-bismethylenedioxyallopregnane, and 3-ethylenedioxy-6,16b -dimethyl-11-keto (and 11b -hydroxy)-17(20),20(21)-bismethylenedioxy-5-pregnene; a process for the preparation of 3,6,11-triketo-16b -methyl-17(20),20(21) -bismethylene-dioxy-allopregnane by reacting 16b -methyl-cortisone with formaldehyde under strongly acidic conditions to produce 3,11-diketo-16b -methyl-17(20),20(21)-bismethylenedioxy-4-pregnene, treating this compound with ethylene glycol in the presence of an acid to produce 3-ethylenedioxy- 11-keto- 16b -methyl-17(20),20(21) - bismethylenedioxy-5-pregnene, oxidising this compound with a per-acid to produce 3-ethylenedioxy-5a ,6a -oxido-11-keto-16b -methyl- 17(20),20(21) -bis-methylenedioxy-allopregnane admixed with the corresponding 5b ,6b -oxido compound, treating this mixture or the 5a ,6a -oxido compound after chromatographic separation with anhydrous formic acid to produce a mixture of the C-5 and C-6 formates of 3,11-diketo- 5,6-dihydroxy- 16b -methyl-17(20), 20(21)-bismethylenedioxyallopregnane, and reacting this mixture with aqueous alkali metal hydroxide; a process for the preparation of 3-ethylenedioxy- 6,11-diketo- 16b -methyl-17(20),20(21) -bismethylenedioxy-allopregnane by reacting 3,6,11-triketo-16b -methyl-17(20),20(21) -bismethylenedioxy-allopregnane with butanone dioxolane; a process for the preparation of 3-ethylenedioxy-6a ,16b -dimethyl-6b -hydroxy- 11-keto-17(20), 20(21)-bismethylenedioxy-allopregnane by reacting 3-ethylenedioxy- 6,11- diketo- 16b -methyl-17(20),20(21) -bismethylenedioxy-allopregnane with a metal magnesium halide; a process for the preparation of 3-ethylene-dioxy-6,16b -dimethyl-11-keto- 17(20),20(21) -bismethylenedioxy-5-pregnene by reacting 3-ethylenedioxy-6a ,16b -dimethyl- 6b -hydroxy-11-keto-17(20), 20(21)-bismethylenedioxy-allopregnane with a dehydrating agent such as a thionyl halide; a process for the preparation of 3-ethylenedioxy-6,16b -dimethyl-11b -hydroxy-17(20),20(21) - bismethylenedioxy-5-pregnene by reducing the corresponding 11-keto compound with lithium aluminium hydride; and a process for the preparation of 3-keto-6a ,16b -dimethyl-11-keto (and b -hydroxy)- 17(20),20(21)- bismethylenedioxy-4-pregnene by treating the corresponding 3-ethylenedioxy-5-pregnene with p-toluenesulphonic acid in acetone. Specifications 867,786, 867,787 and 906,443 also are referred to.
GB1344363A 1958-10-01 1959-09-25 Steroid compounds and their production Expired GB931224A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US76452358A 1958-10-01 1958-10-01

Publications (1)

Publication Number Publication Date
GB931224A true GB931224A (en) 1963-07-17

Family

ID=25070956

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3271259A Expired GB931221A (en) 1958-10-01 1959-09-25 Steroid compounds
GB1344363A Expired GB931224A (en) 1958-10-01 1959-09-25 Steroid compounds and their production

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB3271259A Expired GB931221A (en) 1958-10-01 1959-09-25 Steroid compounds

Country Status (2)

Country Link
BE (1) BE583146A (en)
GB (2) GB931221A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB699256A (en) * 1951-01-31 1953-11-04 British Thomson Houston Co Ltd Improvements in and relating to eddy-current brakes with magnetic locking
DE3227312A1 (en) * 1982-07-19 1984-01-19 Schering AG, 1000 Berlin und 4709 Bergkamen NEW 6.16 DIMETHYL CORTICOIDS, THEIR PRODUCTION AND USE

Also Published As

Publication number Publication date
BE583146A (en) 1960-03-30
GB931221A (en) 1963-07-17

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