GB943952A - A new steroid compound and its formation - Google Patents

A new steroid compound and its formation

Info

Publication number
GB943952A
GB943952A GB4418360A GB4418360A GB943952A GB 943952 A GB943952 A GB 943952A GB 4418360 A GB4418360 A GB 4418360A GB 4418360 A GB4418360 A GB 4418360A GB 943952 A GB943952 A GB 943952A
Authority
GB
United Kingdom
Prior art keywords
methyl
dione
hydroxy
trione
compound
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
GB4418360A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB943952A publication Critical patent/GB943952A/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
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • 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 18-nor-pregn-16-ene-3, 11, 20-trione and processes for the production thereof which comprise the steps of first reacting a 3a -acyloxy-17-hydroxy-17-methyl-18-nor -D-homoetiocholan-11-one with a Grignard reagent to yield a 3a -acyloxy-17-hydroxy-17-methyl-18-nor-D-homoetiocholan-11 -one, saponifying this latter and then oxidising the product and reacting same with a hydrogen halide to form the corresponding 17 - halogeno - 17 - methyl-18-nor-D-homoetiocholane-3, 11-dione thereafter eliminating the hydrogen halide from this compound to give a mixture of the D 16 and D 17 isomers of 17 - methyl - 18 - nor - D - homoetiocholene-3, 11-dione, resolving the mixture so as to separate the 17-methyl-18-nor-D-homoetiochol-16-en-3, 11-dione therefrom and then subjecting this compound to the action of ozone so as to form the 16, 17-ozonide of 17-methyl-18-nor-D-homoetiocholane-3, 11-dione reducing this product to give either 1b - formylmethylene - 2a -acetonyl-4bb -methyl-8ab -perhydrophenanthrene-4, 7-dione or the isomeric compound 16#x-hydroxy-18-nor-pregnane-3, 11, 20-trione and finally dehydrating either product of the reduction reaction to yield the desired 18-norpregn-16-ene-3, 11, 20-trione. Oxidation of the 3a -hydroxy group may be effected with N-bromosuccimide in t-butanol, elimination of hydrogen halide with a lithium-halidelithium carbonate couple and reduction of the ozonide with zinc and acetic acid. Specifications 832,244, 922,315, 943,951, 943,956, 943,957 and 943,958 are referred to.
GB4418360A 1959-12-24 1960-12-22 A new steroid compound and its formation Expired GB943952A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR814116A FR1280589A (en) 1959-12-24 1959-12-24 New 18-nor pregnanic derivative and method of preparation

Publications (1)

Publication Number Publication Date
GB943952A true GB943952A (en) 1963-12-11

Family

ID=8723042

Family Applications (4)

Application Number Title Priority Date Filing Date
GB4519062A Expired GB943956A (en) 1959-12-24 1960-12-22 Novel steroid compounds and processes for their preparation
GB4519162A Expired GB943957A (en) 1959-12-24 1960-12-22 New steroid compounds and processes for the production thereof
GB4519262A Expired GB943958A (en) 1959-12-24 1960-12-22 Novel steroid compounds and processes for their preparation
GB4418360A Expired GB943952A (en) 1959-12-24 1960-12-22 A new steroid compound and its formation

Family Applications Before (3)

Application Number Title Priority Date Filing Date
GB4519062A Expired GB943956A (en) 1959-12-24 1960-12-22 Novel steroid compounds and processes for their preparation
GB4519162A Expired GB943957A (en) 1959-12-24 1960-12-22 New steroid compounds and processes for the production thereof
GB4519262A Expired GB943958A (en) 1959-12-24 1960-12-22 Novel steroid compounds and processes for their preparation

Country Status (3)

Country Link
CH (1) CH394189A (en)
FR (1) FR1280589A (en)
GB (4) GB943956A (en)

Also Published As

Publication number Publication date
CH394189A (en) 1965-06-30
GB943956A (en) 1963-12-11
GB943958A (en) 1963-12-11
GB943957A (en) 1963-12-11
FR1280589A (en) 1962-01-08

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