GB957219A - New steroid compounds and processes for their preparation - Google Patents

New steroid compounds and processes for their preparation

Info

Publication number
GB957219A
GB957219A GB2705561A GB2705561A GB957219A GB 957219 A GB957219 A GB 957219A GB 2705561 A GB2705561 A GB 2705561A GB 2705561 A GB2705561 A GB 2705561A GB 957219 A GB957219 A GB 957219A
Authority
GB
United Kingdom
Prior art keywords
methyl
epoxy
pregnan
group
hydroxy
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
GB2705561A
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 GB957219A publication Critical patent/GB957219A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • 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 11b , 18-epoxy-16a -methyl-20-oxygeno-pregnan-3-one derivatives having the general formula: <FORM:0957219/C2/1> in which both the X and Y are hydrogen or together constitute a 4(5) double bond and the oxygenated grouping Z at the 20-position is =H(O.CO.H), =H(OH) or =O and processes for the preparation thereof by reducing and simultaneously saponifying a 3a -acyloxy-18,20b -epoxy-16a -methyl-5b -pregnan-11-one having the general formula: <FORM:0957219/C2/2> (where Ac represent an acyl radical derived from an organic carboxylic acid) by treatment with an alkaline reducing agent so as to yield 18, 20b -epoxy-3a , 11b -dihydroxy-16a -methyl-5b -pregnane and selectively oxidizing the 3a -hydroxyl group of the latter so as to yield 18, 20b -epoxy-11b -hydroxy-16a -methyl-5b -pregnan-3-one and then treating the latter with formic acid so as to effect migration of the epoxy bridge to the 11b ,18-position and esterifying the hydroxyl group thus created at the 20-position thus yielding the desired 11b , 18-epoxy - 20b - formyloxy - 16a -methyl-5b -pregnan-3-one. A D 4 double bond may be introduced into the product by bromination in 4-position followed by dehydrobromination. The 20-formyloxy group may be hydrolysed to form a 20-hydroxy group which on oxidation gives a 20-keto group. The starting 3a -acetoxy-18, 20b -epoxy-16a -methyl-5b -pregnan-11-one is obtained by reducing at 20-position 3a -acetoxy-16a -methyl-5b -pregnane-11, 20-dione and treating the 20-hydroxy compound thus obtained with lead tetracetate. Specifications 903,808, 957,220 and 957,221 are referred to.
GB2705561A 1960-07-29 1961-07-26 New steroid compounds and processes for their preparation Expired GB957219A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR834359A FR1365260A (en) 1960-07-29 1960-07-29 New oxygenated steroid derivatives and method of preparation

Publications (1)

Publication Number Publication Date
GB957219A true GB957219A (en) 1964-05-06

Family

ID=8736474

Family Applications (3)

Application Number Title Priority Date Filing Date
GB2705561A Expired GB957219A (en) 1960-07-29 1961-07-26 New steroid compounds and processes for their preparation
GB4668863A Expired GB957221A (en) 1960-07-29 1961-07-26 Novel steroid compounds and processes for their preparation
GB4668763A Expired GB957220A (en) 1960-07-29 1961-07-26 A novel steroid compound and processes for its preparation

Family Applications After (2)

Application Number Title Priority Date Filing Date
GB4668863A Expired GB957221A (en) 1960-07-29 1961-07-26 Novel steroid compounds and processes for their preparation
GB4668763A Expired GB957220A (en) 1960-07-29 1961-07-26 A novel steroid compound and processes for its preparation

Country Status (3)

Country Link
CH (1) CH400145A (en)
FR (1) FR1365260A (en)
GB (3) GB957219A (en)

Also Published As

Publication number Publication date
FR1365260A (en) 1964-07-03
GB957221A (en) 1964-05-06
GB957220A (en) 1964-05-06
CH400145A (en) 1965-10-15

Similar Documents

Publication Publication Date Title
GB1058543A (en) 16-methylene-steroids
GB957219A (en) New steroid compounds and processes for their preparation
GB931222A (en) Steroid compounds
GB1060793A (en) Improvements in or relating to steroids and the manufacture thereof
GB514437A (en) Manufacture of compounds of the aetio-cholanic acid series
GB985216A (en) Steroids
GB889379A (en) Improvements in or relating to derivatives of 11ª--hydroxy(and alkoxy)-11, 19-epoxyandrostanes
GB1077393A (en) New steroids
GB715402A (en) 16, 17-dihydroxy-20-keto-pregnenes and-pregnapolyenes and method for producing them
GB973892A (en) Process for the manufacture of d-homo-steroids and new d-homo-steroids
GB943951A (en) New steroid compounds, and processes for their preparation
GB536210A (en) Manufacture of pure compounds of the cyclopentanopolyhydrophenanthrene series
GB970486A (en) New steroid compounds and processes for their preparation
GB944842A (en) Process for the manufacture of esters of halogen-pregnanes
GB896980A (en) Process for the production of 6-methyl-3-keto-í~-steroid compounds
ES255441A1 (en) Procedure for the preparation of 16-methylene-steroids (Machine-translation by Google Translate, not legally binding)
GB878731A (en) New 6ª--chloro-steroids and process for the preparation thereof
GB516445A (en) Manufacture of carboxylic acids of the cyclopentanopolyhydrophenanthrene series
GB990365A (en) Cyclopenteno derivatives of the androstene, ª‡-androstane and ª‰-androstane series and process for their manufacture
GB908770A (en) A new steroid compound and its formation
GB970482A (en) New 17-desoxy corticosteroids and processes for their preparation
GB955614A (en) New steroid compound and processes
GB963287A (en) New steroid compounds and processes for their preparation
GB944841A (en) Process for the manufacture of halogen-pregnanes
GB970586A (en) New steroid compounds and processes for their preparation