GB1413630A - Process for the manufacture of 14, 18-epoxyethano-iminosteroids - Google Patents

Process for the manufacture of 14, 18-epoxyethano-iminosteroids

Info

Publication number
GB1413630A
GB1413630A GB2583173A GB2583173A GB1413630A GB 1413630 A GB1413630 A GB 1413630A GB 2583173 A GB2583173 A GB 2583173A GB 2583173 A GB2583173 A GB 2583173A GB 1413630 A GB1413630 A GB 1413630A
Authority
GB
United Kingdom
Prior art keywords
group
free
esterified
etherified
steroids
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
GB2583173A
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.)
Novartis AG
Original Assignee
Ciba Geigy 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 Geigy AG filed Critical Ciba Geigy AG
Publication of GB1413630A publication Critical patent/GB1413630A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J71/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0036Nitrogen-containing hetero ring
    • C07J71/0057Nitrogen and oxygen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J41/00Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/005Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J71/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005Oxygen-containing hetero ring
    • C07J71/001Oxiranes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fodder In General (AREA)

Abstract

1413630 14,18-Epoxyethanoimino steroids CIBA-GEIGY AG 30 May 1973 [30 May 1972 25 Jan 1973] 25831/73 Heading C2U Steroids of the formula and their salts, wherein P is -CH(R)CH 3 in which R is a free, esterified or etherified OH group in the α- or #-configuration (alternatively known as 20S- and 20R-configuration); R 1 is a free or ketalized oxo group or a free, esterified or etherified OH group together with a H atom; R 2 is H 2 or H when a #<SP>7</SP>-double bond is present, or a free or ketalized oxo group or a free, esterified or etherified OH group together with a H atom; R 3 is H, C 1-6 alkyl or C 7-13 aralkyl ; R 4 is H 2 , or H when a #<SP>9(11)</SP>-double bond is present, or a free or ketalized oxo group, or a free, esterified OH group together with a H atom; R 5 is a H atom, or a free, esterified or etherified OH group, or together with R 1 , a 3α,9α-epoxy group, in which case R 1 is a free, esterified oretherified #-OH group and a 5#-H atom is present; R 6 is H 2 or O; and the #<SP>4</SP>-, #<SP>5</SP>-, #<SP>7</SP>- and #<SP>9(11)</SP>-double bonds are optional, are prepared by reacting corresponding 14#- (etherified hydroxy)-18-als with amines R 3 NH 2 to give 13-CH=NR 3 steroids, reducing these with metal hydride reducing agents to give 13-CH 2 NHR 3 steroids, reacting these with haloacetyl halides to give 13-CH 2 N(R 3 )COCH 2 X steroids (X is a halogen), treating these with a strong acid to release the free 14#-OH group and cyclizing the resulting compounds with a basic agent. Optionally and in any desired order the lactan group may then be reduced to the corresponding amino group using a complex metal hydride, functionally modified hydroxy and keto groups liberated, free OH groups esterified or etherified, a 7-OH group split off with the formation of a #<SP>7</SP>- double bond (if appropriate after prior protection of further free OH groups) and an 11-OH group oxidized to an 11-keto group. Specified products include batrachotoxinin A 7,8-dihydrobatrachotoxinin A; 20-epi-batrachotoxinin A; and 7,8-dihydro-20-epi-batrachotoxinin A; and esters and ethers of these compounds. (20S) - 3# - methoxy - 3α,9α - oxido - 7α,11α,20- triacetoxy - 14# - methylthio - methoxy - 18 - oxo- #<SP>16</SP> - 5# - pregnene is obtained from 3# - methoxy - 3α,9α : 14#,15#- dioxido - 7α,11α,18- triacetoxy - 20 - oxo - #<SP>16</SP> - 5# - pregnene via 3# - methoxy - 3α,9α - oxido - 7α,11α,18 - triacetoxy - 14# - hydroxy - 20 - oxo - #<SP>16</SP> - 5#- pregnene, the corresponding 14,18-diol, its 14,18- acetonide, the corresponding 20-ol (20R-form also isolated and (20S) - 3# - methoxy - 3α,9α - oxido - 7α,11α,- 20 - triacetoxy - 14#,18 - dihydroxy - #<SP>16</SP> - 5#- pregnene. The steroids produced by the novel process have therapeutic actions which resemble those of cardiac-active digitalis substances, and they may be made up into pharmaceutical compositions with suitable carriers. Specification 1,413,629 is referred to. Reference has been directed by the Comptroller to Specifications 1,318,932 and 1,336,434.
GB2583173A 1972-05-30 1973-05-30 Process for the manufacture of 14, 18-epoxyethano-iminosteroids Expired GB1413630A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH796772 1972-05-30
CH108073 1973-01-25

Publications (1)

Publication Number Publication Date
GB1413630A true GB1413630A (en) 1975-11-12

Family

ID=25686590

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2583173A Expired GB1413630A (en) 1972-05-30 1973-05-30 Process for the manufacture of 14, 18-epoxyethano-iminosteroids

Country Status (4)

Country Link
JP (1) JPS4961186A (en)
DE (1) DE2325873A1 (en)
FR (1) FR2186260B1 (en)
GB (1) GB1413630A (en)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1768162A1 (en) * 1968-04-06 1971-09-30 Schering Ag New 18-nor-14ss-pregnano- [13,14-f] -hexahydro-1,4-oxazepine
CH576488A5 (en) * 1969-06-13 1976-06-15 Ciba Geigy Ag
BE757924A (en) * 1969-10-24 1971-04-01 Geigy Ag J R STEROID COMPOUNDS WITH HETEROCYCLIC NITROGEN CORE, THEIR PREPARATION AND MEDICINAL PRODUCTS CONTAINING SUCH COMPOUNDS
CH583253A5 (en) * 1970-07-24 1976-12-31 Ciba Geigy Ag

Also Published As

Publication number Publication date
FR2186260B1 (en) 1977-04-15
JPS4961186A (en) 1974-06-13
FR2186260A1 (en) 1974-01-11
DE2325873A1 (en) 1973-12-13

Similar Documents

Publication Publication Date Title
GB1455270A (en) 11,11-alkylidene steroids
GB1254626A (en) New 19-hydroxy-3-aza-a-homo-steroids and a process for their manufacture
GB1413630A (en) Process for the manufacture of 14, 18-epoxyethano-iminosteroids
GB1399162A (en) 6-keto-delta1,3,5-10-steroids and process for the manufacture of 6-keto-delta1,3,5-10-steroids
DE2529969A1 (en) NEW HAPTENES DERIVED FROM TESTOSTERONE, METHODS FOR THEIR MANUFACTURE AND THEIR USE IN THE MANUFACTURE OF ANTIGENES
IE41233L (en) 11-substituted estrane steroids.
GB1450807A (en) Cardenolide glycosides and process for their manufacture
GB1530615A (en) 15,16-methylene-steroids of the pregnane series
GB1514621A (en) 13-ethynyl-and 13-(2-halovinyl)-steroids and their preparation
GB1140642A (en) 17-‡-cyanoethynyl-steroids
US3242169A (en) 6alpha-dimethylaminomethyl-3-oxo-delta4-steroids and method for producing same
US3318789A (en) Process for the manufacture of 19-nor-steroids
GB1311725A (en) 18-cyano pregnane compounds and process for their manufacture
GB1282520A (en) 06-methyl-steroids and processes for their preparation
GB1255950A (en) 08-methylene-steroids and process for their manufacture
US3002981A (en) Androstene-16-ones
GB1308656A (en) Cardadienolide derivatives and process for their manufacture
GB1051580A (en)
GB1208884A (en) Tetrahydropyranylethers of steroids and process for their manufacture
GB1495513A (en) Steroid compounds of the 20(22)-cardenolide series
US3275663A (en) 2-hydroxymethylene testosterone derivatives
US3053862A (en) 3-unsubstituted steroids of the pregnane series
GB1276743A (en) Aldehydes of the pregnane series and process for their manufacture
GB1371798A (en) Cardenolide derivatives and a process for their manufacture
GB1214507A (en) 03-alkyl-11-oxygenated-gonenes

Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee