GB938566A - 18-oxygenated pregnanes and process for their manufacture - Google Patents

18-oxygenated pregnanes and process for their manufacture

Info

Publication number
GB938566A
GB938566A GB4342659A GB4342659A GB938566A GB 938566 A GB938566 A GB 938566A GB 4342659 A GB4342659 A GB 4342659A GB 4342659 A GB4342659 A GB 4342659A GB 938566 A GB938566 A GB 938566A
Authority
GB
United Kingdom
Prior art keywords
oxo
conimine
oxido
hydroxy
iminopregnadiene
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
GB4342659A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB938566A publication Critical patent/GB938566A/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
    • 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 D 20:N-18,20-iminopregnenes, particularly those that contain a free or functionally converted hydroxyl or oxo group in the 3-position and which may contain a further double bond in the ring system, e.g. D 4,20:N-3-oxo-18,20-iminopregnadiene, together with a process for the manufacture of an 18-oxygenated pregnane by treating a D 20:N-18,20-iminopregnene with nitrous acid, and if desired reacting the 18-hydroxy-20-oxo-pregnane so obtained with an oxidising agent and/or if desired converting an 18,20-dioxopregnane or a 20-oxopregnane-18-acid so obtained into a functional derivative thereof. The 18-hydroxy-20-oxopregnane may also exist in the tautomeric form 18,20-oxido-20-hydroxy pregnane and the 18,20-oxido-20 acyloxy compounds are obtained upon esterification. A detailed example illustrates the conversion of D 4,20:N-3-oxo-18,20-imino-pregnadiene to D 4-3-oxo-18,20-oxido-20-hydroxypregnene or 18-hydroxyprogesterone, its oxidation to 18-oxoprogesterone and its esterification to D 4-3-oxo-18,20-oxido-20-acetoxy pregnene. The D 20:N-18,20-iminopregnene compounds which may contain in the ring system, particularly in the 3- and 11-positions, free or functionally converted hydroxy and oxo groups, amino groups, e.g. methylamino, and also additional double bonds, particularly in the 1:2, 4:5, 5:6, or 9:11 positions, are obtained by halogenating an 18,20- iminopregnane compound and treating the N-halo compound so obtained with a base or by introducing the 20:N double bond by direct dehydrogenation, e.g. with mercuric acetate. Thus D 4,20:N-3-oxo-18,20-iminopregnadiene is prepared from conessine by cyanogen bromide treatment to give N,N1-dicyano-conimine, treatment of the latter with ethanolic KOH to give conimine, chlorination of conimine with N-chlorosuccinimide and reaction of the resulting N,N1-dichloro-conimine with sodium methylate in methanol to give D 4,20:N-3-imino-18,20-iminopregnadiene which is then hydrolysed with acid. Specification 910,768 is referred to.
GB4342659A 1958-12-19 1959-12-21 18-oxygenated pregnanes and process for their manufacture Expired GB938566A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH6754658 1958-12-19

Publications (1)

Publication Number Publication Date
GB938566A true GB938566A (en) 1963-10-02

Family

ID=4528051

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4342659A Expired GB938566A (en) 1958-12-19 1959-12-21 18-oxygenated pregnanes and process for their manufacture

Country Status (1)

Country Link
GB (1) GB938566A (en)

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