GB1001193A - Improvements in or relating to the production of steroid compounds - Google Patents

Improvements in or relating to the production of steroid compounds

Info

Publication number
GB1001193A
GB1001193A GB2489762A GB2489762A GB1001193A GB 1001193 A GB1001193 A GB 1001193A GB 2489762 A GB2489762 A GB 2489762A GB 2489762 A GB2489762 A GB 2489762A GB 1001193 A GB1001193 A GB 1001193A
Authority
GB
United Kingdom
Prior art keywords
pregn
seco
compound
des
trione
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
GB2489762A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB1001193A publication Critical patent/GB1001193A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • 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 4,5-seco-19-nor-pregna-3,5,20-trione and a process for the preparation of 19-nor-pregn-4-en-3,20-dione, in which 4,5 - seco - 19 - nor - pregn - 9 - en - 3,5,20 - trione is subjected to catalytic stereo-specific hydrogenation so as to reduce the double bond at 9 (10)-position thereof thus forming 4,5 - seco - 19 - nor - pregna - 3,5,20-trione and the latter is treated with a cyclizing agent to yield the desired 19-nor-pregn-4-ene-3,20-dione. Hydrogenation may be effected in the presence of palladium or platinum in alkaline medium. Cyclization may be effected with sodium t-amylate or hydrochloric acid in acetic acid medium. 4,5-Seco-19-nor-pregn-9-ene-3,5,20-trione is obtained by oxidizing 17b -hydroxy - 5 - methoxy - des A - estra - 5,7,9-triene to obtain 5-methoxy-des-A-estra-5,7,9-trien-17-one, treating said 17-keto compound with acetylene to obtain 17a -ethynyl - 17b -hydroxy - 5 - methoxy - des A - estra - 5,7,9 triene, esterifying said 17a -ethynyl-17b -hydroxy compound to obtain the corresponding 17a -ethynyl-17b -acyloxy compound, hydrating said 17a - ethynyl - 17b - acyloxy compound to obtain 17b - acyloxy - 17a - acetyl - 5 - methoxy-des A-estra-5,7,9-triene, reducing said 17a -acetyl compound to obtain 20-hydroxy-19-nor-des A-pregn-9-en-5-one, oxidizing said 20-hydroxy compound to obtain 19-nor-des A-pregn-9-ene-5,20-dione and forming a 5-enamine thereof, treating said enamine with 1,3-dichloro-2-butene to obtain 3-chloro-4,5-seco-19 - nor - pregna - 2,9 - diene - 5,20 - dione, and treating said 3-chloro-4,5-seco compound with sulphuric acid to obtain the desired 4,5 - seco - 19 - nor - pregn - 9 - ene - 3,5,20-trione. Specification 1,001,192 is referred to.
GB2489762A 1961-06-28 1962-06-28 Improvements in or relating to the production of steroid compounds Expired GB1001193A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR866332A FR1369324A (en) 1961-06-28 1961-06-28 New process for preparing a 19-nor steroid

Publications (1)

Publication Number Publication Date
GB1001193A true GB1001193A (en) 1965-08-11

Family

ID=8758198

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2489762A Expired GB1001193A (en) 1961-06-28 1962-06-28 Improvements in or relating to the production of steroid compounds

Country Status (5)

Country Link
CH (1) CH411867A (en)
DK (1) DK111565B (en)
FR (1) FR1369324A (en)
GB (1) GB1001193A (en)
SE (1) SE310363B (en)

Also Published As

Publication number Publication date
FR1369324A (en) 1964-08-14
SE310363B (en) 1969-04-28
CH411867A (en) 1966-04-30
DK111565B (en) 1968-09-16

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