GB899804A - Improvements in or relating to 16-substituted-3-oxo-í~-steroid compounds - Google Patents

Improvements in or relating to 16-substituted-3-oxo-í~-steroid compounds

Info

Publication number
GB899804A
GB899804A GB153660A GB153660A GB899804A GB 899804 A GB899804 A GB 899804A GB 153660 A GB153660 A GB 153660A GB 153660 A GB153660 A GB 153660A GB 899804 A GB899804 A GB 899804A
Authority
GB
United Kingdom
Prior art keywords
compound
acetoxy
treating
hydrogen
methyl
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
GB153660A
Inventor
David Neville Kirk
Vladimir Petrow
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 GB153660A priority Critical patent/GB899804A/en
Priority to DEB60824A priority patent/DE1161265B/en
Priority to CH41161A priority patent/CH388951A/en
Priority to FR1564451D priority patent/FR1564451A/fr
Publication of GB899804A publication Critical patent/GB899804A/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 steroid compounds of the general formula <FORM:0899804/IV (b)/1> wherein R represents hydrogen or an acyl radical containing up to 10 carbon atoms, R1 represents hydrogen or the methyl radical, and R111 represents hydrogen and R11 represents <FORM:0899804/IV (b)/2> or R111 represents the methyl radical and R11 represents <FORM:0899804/IV (b)/3> and the preparation thereof by treating the corresponding 3-oxo-D 4-steroids of the general formula <FORM:0899804/IV (b)/4> wherein R, R1, R11 and R111 have the above significance, with 2,3-dicyano-1,4-benzoquinone which may be additionally substituted by 1 or 2 chlorine atoms, e.g. 2,3-dicyano-5,6-dichlorobenzoquinone, in an inert solvent. The Provisional Specification refers to compounds of the first general formula above wherein R represents hydrogen or a lower acyl radical, R1 and R11 represent hydrogen or the methyl radical, and R11 represents <FORM:0899804/IV (b)/5> and to the preparation of these compounds by a method similar to that given above. 17a - Acetoxy - 16 - ethylidenepregn - 4 - ene 3, 20 - dione is prepared by treating 3-acetoxypregna-5,16-dien-20-one with diazoethane to form 3b - acetoxy - 16, 17 - (11 - methyl - 21, 31 - diazacylopent - 21 - eno) - pregn - 5 - en - 20 - one, heating this compound to form 3b -acetoxy-16-ethylpregn-5,16-dien-20-one, treating this compound with alkaline hydrogen peroxide to form 16a , 17a - epoxy - 16b - methyl - 3b - hydroxy - pregn - 5 - en - 20 - one, acetylating this compound to form the corresponding 3b -acetoxy compound, treating this compound with hydrogen bromide in acetic acid to form 3b -acetoxy-16-ethylidene-17a -hydroxypregn-5-en-20-one, acetylating this compound to form 3b ,17a -diacetoxy-16-ethyl-idenepregn-5-en-20-one, selectively hydrolysing this compound to form 17a -acetoxy-16-ethylidene-3b -hydroxypregn-5-en-20-one, and oxidising this compound with aluminium t-butoxide. Specifications 852,847 and 854,343 are referred to. Reference has been directed by the Comptroller to Specifications 857,114 and 858,033.
GB153660A 1960-01-15 1960-01-15 Improvements in or relating to 16-substituted-3-oxo-í~-steroid compounds Expired GB899804A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB153660A GB899804A (en) 1960-01-15 1960-01-15 Improvements in or relating to 16-substituted-3-oxo-í~-steroid compounds
DEB60824A DE1161265B (en) 1960-01-15 1961-01-12 Process for the production of 3-oxo-í¸-steroids
CH41161A CH388951A (en) 1960-01-15 1961-01-13 Process for the preparation of a 3-oxo-1,4-steroid
FR1564451D FR1564451A (en) 1960-01-15 1961-01-14

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB153660A GB899804A (en) 1960-01-15 1960-01-15 Improvements in or relating to 16-substituted-3-oxo-í~-steroid compounds

Publications (1)

Publication Number Publication Date
GB899804A true GB899804A (en) 1962-06-27

Family

ID=9723685

Family Applications (1)

Application Number Title Priority Date Filing Date
GB153660A Expired GB899804A (en) 1960-01-15 1960-01-15 Improvements in or relating to 16-substituted-3-oxo-í~-steroid compounds

Country Status (4)

Country Link
CH (1) CH388951A (en)
DE (1) DE1161265B (en)
FR (1) FR1564451A (en)
GB (1) GB899804A (en)

Also Published As

Publication number Publication date
FR1564451A (en) 1969-04-25
CH388951A (en) 1965-03-15
DE1161265B (en) 1964-01-16

Similar Documents

Publication Publication Date Title
GB899804A (en) Improvements in or relating to 16-substituted-3-oxo-í~-steroid compounds
GB931296A (en) Steroid compounds
GB989881A (en) Improvements in or relating to 10 -methyl steroids and the production thereof
GB935116A (en) New cyclopentanophenanthrene derivatives and processes for the production thereof
GB970487A (en) Novel steroids compounds and processes for the preparation thereof
GB959869A (en) Oxasteroids of the pregnane series
GB899026A (en) Improvements in or relating to estratrienes
GB905526A (en) Improvements in or relating to epoxysteroids
GB965357A (en) Improvements in or relating to steroid compounds
GB881501A (en) Substituted pregnenes
GB896980A (en) Process for the production of 6-methyl-3-keto-í~-steroid compounds
GB908770A (en) A new steroid compound and its formation
GB952492A (en) New steroid compounds and processes for their preparation
GB934713A (en) New steroid compounds and processes for their preparation
GB1057337A (en) Novel 3-substituted-androst-11-ones and processes for their preparation
GB948523A (en) 2-halogenated steroids of the pregnane series
ES262796A1 (en) New steroid compounds and their production
GB951474A (en) Improvements in or relating to the bromination of steroid derivatives
GB887007A (en) New a-nor-steroid compounds
GB668533A (en) Process of introducing a double bond adjacent to a keto group in an organic compound
GB1086461A (en) 1,1-ethylene-17ª‡-alkyl-í¸-5ª‡-androsten-17ª‰-ols and their 17-esters and a process for their manufacture
GB934705A (en) Improvements in or relating to steroids
GB944718A (en) New steroid compounds and processes for their preparation
GB1005726A (en) Processes for the preparation of 17ª‡-ethynyl-17ª‰-hydroxy derivatives of 13ª‰-?-propyl-18-nor-estradiol
GB855800A (en) New cyclopentanophenanthrene derivatives and process for the production thereof