ES255202A1 - Processes for the production of steroid compounds - Google Patents

Processes for the production of steroid compounds

Info

Publication number
ES255202A1
ES255202A1 ES0255202A ES255202A ES255202A1 ES 255202 A1 ES255202 A1 ES 255202A1 ES 0255202 A ES0255202 A ES 0255202A ES 255202 A ES255202 A ES 255202A ES 255202 A1 ES255202 A1 ES 255202A1
Authority
ES
Spain
Prior art keywords
methyl
pregna
trione
groups
protected
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
ES0255202A
Other languages
Spanish (es)
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.)
Laboratoires Francais de Chimiotherapie SA
Laboratoires Francaise de Chimiotherapie
Original Assignee
Laboratoires Francais de Chimiotherapie SA
Laboratoires Francaise de Chimiotherapie
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 Laboratoires Francais de Chimiotherapie SA, Laboratoires Francaise de Chimiotherapie filed Critical Laboratoires Francais de Chimiotherapie SA
Publication of ES255202A1 publication Critical patent/ES255202A1/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 11a ,17a -dihydroxy-16a -methyl-pregna-3,20-dione, the 3,20-diketals thereof, and a process for the preparation of compounds of the formula: <FORM:0934703/IV(a)/1> wherein R is =H(a -OH) or = O, which comprises condensing pregn-16-en-3,11,20-trione with diazo-methane in an inert organic solvent to form the corresponding 16,17-pyrazoline, subjecting this compound to thermolysis to form 16-methyl-pregn-16-en-3,11,20-trione, protecting the 3- and 20-keto groups of this compound, epoxidising the resultant product to form the corresponding 16a ,17a -epoxy-16b -methyl-pregna-3, 11,20-trione derivative wherein the 3 and 20 groups are protected, reacting this derivative with an alkali metal or an alkaline earth metal in the presence of a lower aliphatic amine to break the epoxide bridge, invert the steric position of the 16-methyl group and reduce the 11-ketone function, thereby obtaining the 11a ,17a -dihydroxy-16a -methyl-pregna-3,20-dione derivative wherein the 3- and 20- groups are protected and thereafter reliberating the protected keto groups to yield the desired compound in which R is =H(a -OH) followed, if desired, by oxidation of the latter to give the desired compound in which R is =O. Thermolysis of the 16,17-pyrazoline is effected by heating in a high b.p. solvent. The breaking of the epoxide bridge may be effected with lithium in the presence of monomethylamine at 0 DEG C. to -40 DEG C. Specifications 807,203, 874,779, 934,701 and 934,712 are referred to.
ES0255202A 1959-01-23 1960-01-22 Processes for the production of steroid compounds Expired ES255202A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR784845A FR1234733A (en) 1959-01-23 1959-01-23 Process for preparing 16 alpha-methyl pregnane-diones

Publications (1)

Publication Number Publication Date
ES255202A1 true ES255202A1 (en) 1960-11-16

Family

ID=8710465

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0255202A Expired ES255202A1 (en) 1959-01-23 1960-01-22 Processes for the production of steroid compounds

Country Status (5)

Country Link
BE (1) BE586857A (en)
CH (1) CH369757A (en)
ES (1) ES255202A1 (en)
FR (1) FR1234733A (en)
GB (2) GB934703A (en)

Also Published As

Publication number Publication date
GB934712A (en) 1963-08-21
FR1234733A (en) 1960-10-19
CH369757A (en) 1963-06-15
GB934703A (en) 1963-08-21
BE586857A (en) 1960-07-22

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