GB850423A - Improvements in or relating to 6-methyl steroid compounds - Google Patents

Improvements in or relating to 6-methyl steroid compounds

Info

Publication number
GB850423A
GB850423A GB2206558A GB2206558A GB850423A GB 850423 A GB850423 A GB 850423A GB 2206558 A GB2206558 A GB 2206558A GB 2206558 A GB2206558 A GB 2206558A GB 850423 A GB850423 A GB 850423A
Authority
GB
United Kingdom
Prior art keywords
organic solvent
preparation
aqueous
yield
hours
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
GB2206558A
Inventor
Vladimir Petrow
David Morton Williamson
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.)
BDH Chemicals Ltd
Original Assignee
BDH Chemicals 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 BDH Chemicals Ltd filed Critical BDH Chemicals Ltd
Priority to GB2206558A priority Critical patent/GB850423A/en
Priority to CH7512359A priority patent/CH377810A/en
Priority to BE580502A priority patent/BE580502A/en
Priority to CH7553959A priority patent/CH374998A/en
Publication of GB850423A publication Critical patent/GB850423A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not 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
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • 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 steroids of the formulae <FORM:0850423/IV(b)/1> and the preparation of the steroids (I) by reacting 3b -hydroxy- or a 3b -acyloxy-6-methyl pregna-5 : 6-dien-20-one with diazomethane to yield the pyrazolines (III) and then thermally decomposing these to yield the desired products. The first process is preferably performed in an inert organic solvent such as diethyl ether and the reaction mixture allowed to stand at room temperature for periods of 16 to 40 hours. The thermal decomposition is advantageously performed at reflux temperature in an inert organic solvent of b.p. approximately the same as the m.p. of the pyrazoline for a duration of 3 to 5 hours, suitable solvents being dibutyl ether, p-cymene and ethylene glycol. The products containing a 3b -acyloxy group may be hydrolysed to the 3b -ol by heating with an alkali metal hydroxide or carbonate in an aqueous organic solvent such as aqueous acetone or aqueous t-butanol. Examples describe the preparation of the 3b -acetoxy compounds of the invention and hydrolysis of the 16-methyl compound to the 3b -ol, and the preparation of the latter compound direct by the processes of the invention. The Provisional Specification also comprises the subject-matter of the Specification 850,424.
GB2206558A 1958-07-09 1958-07-09 Improvements in or relating to 6-methyl steroid compounds Expired GB850423A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB2206558A GB850423A (en) 1958-07-09 1958-07-09 Improvements in or relating to 6-methyl steroid compounds
CH7512359A CH377810A (en) 1958-07-09 1959-06-30 Process for the preparation of 6a, 16-dimethylpregna-4,16-diene-3,20-dione
BE580502A BE580502A (en) 1958-07-09 1959-07-08 Process for the preparation of new 6,16-dimethylpregnane derivatives and products obtained
CH7553959A CH374998A (en) 1958-07-09 1959-07-09 Process for the preparation of 3B-oxy- and 3B-acyloxy-6,16-dimethylpregna-5,16-dien-20-one

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2206558A GB850423A (en) 1958-07-09 1958-07-09 Improvements in or relating to 6-methyl steroid compounds

Publications (1)

Publication Number Publication Date
GB850423A true GB850423A (en) 1960-10-05

Family

ID=10173334

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2206558A Expired GB850423A (en) 1958-07-09 1958-07-09 Improvements in or relating to 6-methyl steroid compounds

Country Status (3)

Country Link
BE (1) BE580502A (en)
CH (1) CH374998A (en)
GB (1) GB850423A (en)

Also Published As

Publication number Publication date
BE580502A (en) 1959-11-03
CH374998A (en) 1964-02-15

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