GB1045476A - 8ª‰-substituted-11ª‰-hydroxysteroids and their preparation - Google Patents

8ª‰-substituted-11ª‰-hydroxysteroids and their preparation

Info

Publication number
GB1045476A
GB1045476A GB597665A GB597665A GB1045476A GB 1045476 A GB1045476 A GB 1045476A GB 597665 A GB597665 A GB 597665A GB 597665 A GB597665 A GB 597665A GB 1045476 A GB1045476 A GB 1045476A
Authority
GB
United Kingdom
Prior art keywords
iminomethyl
acid
steroid
effected
formyl
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
GB597665A
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.)
Shionogi and Co Ltd
Original Assignee
Shionogi and Co Ltd
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 Shionogi and Co Ltd filed Critical Shionogi and Co Ltd
Publication of GB1045476A publication Critical patent/GB1045476A/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
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • 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
    • C07J75/00—Processes for the preparation of steroids in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises (1) a process for preparing an 8b - iminomethyl- or 8b - formyl-11b -hydroxy steroid wherein an N-acylated 8b , 11b -carboimidic lactone is subjected to reductive fission by the Birch reduction and, when required, the resulting 8b -iminomethyl-11b -hydroxy steroid is treated with an acid to give the corresponding 8b -formyl steroid; and (2) 8b - iminomethyl - 5a - 22 - ergostene-3b ,11b - diol and 3,3:17,17 - bisethylenedioxy-8b - iminomethyl - 5 - androsten - 11b - ol and the corresponding 8b -formyl steroids. The starting material may be of the androstane, pregnane, cholane, cholestane, sitostane, ergostane or spirostane series and may contain free or functionally converted hydroxyl and oxo groups and double bonds. If the reductive fission is effected in the presence of a proton source the 8b -iminomethyl steroid results directly; but when it is effected on an N-alkoxycarbonyl compound in the absence of a proton source an N-alkoxycarbonyl dihydrocarboimidic acid lactone results which is then hydrolysed with an alkali to the required 8-iminomethyl compound. The N-acylating group may be a lower (i.e. C1- 8) alkanoyl, aroyl, lower alkoxycarbonyl or aryloxy carbonyl group. The acid treatment may be effected with an acid, metal oxide or salt which can release protons or act as a pseudo acid.
GB597665A 1962-08-24 1963-08-23 8ª‰-substituted-11ª‰-hydroxysteroids and their preparation Expired GB1045476A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP3653462 1962-08-24
JP3653262 1962-08-24
JP3653362 1962-08-24
JP3653162 1962-08-24

Publications (1)

Publication Number Publication Date
GB1045476A true GB1045476A (en) 1966-10-12

Family

ID=27460278

Family Applications (3)

Application Number Title Priority Date Filing Date
GB597665A Expired GB1045476A (en) 1962-08-24 1963-08-23 8ª‰-substituted-11ª‰-hydroxysteroids and their preparation
GB3349063A Expired GB1045474A (en) 1962-08-24 1963-08-23 8ª‰-methyl-11ª‰-hydroxysteroids and their preparation
GB597565A Expired GB1045475A (en) 1962-08-24 1963-08-28 Steroid 8ª‰,11ª‰-carboimidic lactones and their preparation

Family Applications After (2)

Application Number Title Priority Date Filing Date
GB3349063A Expired GB1045474A (en) 1962-08-24 1963-08-23 8ª‰-methyl-11ª‰-hydroxysteroids and their preparation
GB597565A Expired GB1045475A (en) 1962-08-24 1963-08-28 Steroid 8ª‰,11ª‰-carboimidic lactones and their preparation

Country Status (2)

Country Link
CH (1) CH441298A (en)
GB (3) GB1045476A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109180775B (en) * 2018-09-05 2021-03-23 常州大学怀德学院 C-28 imine substituted betulin isomer derivative and preparation method and application thereof

Also Published As

Publication number Publication date
GB1045475A (en) 1966-10-12
GB1045474A (en) 1966-10-12
CH441298A (en) 1967-08-15

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