GB938566A - 18-oxygenated pregnanes and process for their manufacture - Google Patents
18-oxygenated pregnanes and process for their manufactureInfo
- 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
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.
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) |
-
1959
- 1959-12-21 GB GB4342659A patent/GB938566A/en not_active Expired
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