GB1018997A - 6-aminosteroids and 6-oximino steroids - Google Patents

6-aminosteroids and 6-oximino steroids

Info

Publication number
GB1018997A
GB1018997A GB1022163A GB1022163A GB1018997A GB 1018997 A GB1018997 A GB 1018997A GB 1022163 A GB1022163 A GB 1022163A GB 1022163 A GB1022163 A GB 1022163A GB 1018997 A GB1018997 A GB 1018997A
Authority
GB
United Kingdom
Prior art keywords
amino
cycloandrostan
propylenedioxy
androst
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
GB1022163A
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.)
Abbott Laboratories
Original Assignee
Abbott Laboratories
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 Abbott Laboratories filed Critical Abbott Laboratories
Publication of GB1018997A publication Critical patent/GB1018997A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
    • 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 steroids of the formula <FORM:1018997/C2/1> (wherein Z is an oximino group NOH doubly bonded to the steroid nucleus at the 6-position or an amino or acylamino group NHR, R being hydrogen or acyl, singly bonded to the steroid nucleus at the 6-position in the a - or BETA-configuration; and Y is -O(CH2)nO-, n being 2 or 3 and the alkylene chain being optionally methyl substituted, and, when Z is NHR, Y can also be an oxygen atom, and the preparation of 6a -amino - 17 - ethylenedioxy- or 6a - amino - 17 - propylene (1,3)dioxy - 3a ,5a - cycloandrostane by heating the appropriate 3a ,5a -cycloandrostan -6,17-dione 17-ketal with an excess of hydroxylamine to give the corresponding 6-oxime, and reducing this in an alcoholic solution and in the presence of an alkali metal. Other 6a -amino compounds of the invention are prepared similarly, and can be acylated to the corresponding 6a -acylamino-17-ketals and subsequently hydrolysed to 6a -acylamino-17-oxo-3a ,5a -cycloandrostanes. Alternatively the 6a -amino -17-ketals can be hydrolysed directly with aqueous acid to salts of 6a -amino-17 oxo-3a ,5a -cycloandrostane, from which the free amine can subsequently be released. The 6b -amino compounds of the invention are prepared by treating a sulphonic ester of the appropriate ketal of 3b -hydroxy -androst-5-en-17-one with ammonia to give a 6b -amino-3a ,5a -cycloandrostan-17-one ketal, which can be acylated and/or hydrolysed as for the 6a -amino compounds. Examples are given, by-products in the reaction with ammonia of a sulphonic ester being 3a and 3b -amino-17 -ethylenedioxyandrost-5-enes, which are separated as their acetic acid salts by crystallization. A list of suitable acyl groups R is also provided. 17 - (1,3 - Propylenedioxy) - 3a ,5a - cycloandrostan - 6 - one is prepared by ketalizing 3b - hydroxy - androst - 5 - en - 17 - one to give 3b - hydroxy - 17 - (1,3 - propylenedioxy) - androst -5-ene, converting this to the 3 b -p-toluene-sulphonyloxy derivative, hydrolysing this to 17 - (1,3 - propylenedioxy) - 3a ,5a - cycloandrostan -6b -ol and oxidizing this.
GB1022163A 1962-03-16 1963-03-14 6-aminosteroids and 6-oximino steroids Expired GB1018997A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US18035762A 1962-03-16 1962-03-16

Publications (1)

Publication Number Publication Date
GB1018997A true GB1018997A (en) 1966-02-02

Family

ID=22660148

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1022163A Expired GB1018997A (en) 1962-03-16 1963-03-14 6-aminosteroids and 6-oximino steroids

Country Status (4)

Country Link
CH (1) CH423767A (en)
DE (1) DE1219482B (en)
FR (2) FR1351750A (en)
GB (1) GB1018997A (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3009925A (en) * 1959-12-07 1961-11-21 Upjohn Co 17-aminoandrostanes
US3000910A (en) * 1961-04-07 1961-09-19 Upjohn Co 17-isonitrose-3-aminoethers of the androstane series

Also Published As

Publication number Publication date
CH423767A (en) 1966-11-15
FR2585M (en) 1964-06-08
DE1219482B (en) 1966-06-23
FR1351750A (en) 1964-02-07

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