GB955612A - New steroid compounds, processes for their preparation and conversion into compounds of utility in the production of substituted corticosteroids - Google Patents

New steroid compounds, processes for their preparation and conversion into compounds of utility in the production of substituted corticosteroids

Info

Publication number
GB955612A
GB955612A GB852561A GB852561A GB955612A GB 955612 A GB955612 A GB 955612A GB 852561 A GB852561 A GB 852561A GB 852561 A GB852561 A GB 852561A GB 955612 A GB955612 A GB 955612A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
compound
dione
methyl
compounds
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
GB852561A
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 GB955612A publication Critical patent/GB955612A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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 the 3, 20-diketals of 17a -hydroxy-16a -methyl-pregn-4-ene-3, 20-dione having the formula: <FORM:0955612/C2/1> in which X represents an 11-keto group and a hydrogen atom at the 9-position, or an 11b -hydroxy and a hydrogen atom at the 9-position, or a 9(11)-double bond, and R is the residue of a ketal grouping and processes for the preparation thereof in which 3a , 17a -dihydroxy-16a -methyl-pregnane-11, 20-dione is oxidized to yield the corresponding 3-keto derivative which is brominated to produce the 4-bromo derivative thereof, the latter is dehydrobrominated so as to introduce a 4, 5-double bond, the resultant compound is ketalized to yield a 3, 20-diketal of 17a -hydroxy - 16a - methyl - pregn - 4 - ene - 3, 11, 20-trione, and if desired this compound is reduced at 11-position to obtain the corresponding 11b -hydroxy compound which may if desired be dehydrated to obtain a 3, 20-diketal of 17a -hydroxy - 16a - methyl - pregn - 4, 9(11) - diene-3, 20-dione. Subsequent hydrolysis regenerates the 3, 20-diketo compound which is iodinated at 21-position and treated with an acylating agent to obtain a 17a -hydroxy-21-acyloxy-16a -methylpregna-4, 9(11)-diene-3, 20-dione. The oxidation of the starting compound and bromination may be effected in a single stage with N-bromosuccinimide in t-butanol, whilst dehydrobromination may be effected with a lithium bromidelithium carbonate couple. Iodination in 21-position may be effected by treatment with iodine in the presence of calcium oxide and calcium chloride. Specifications 934,702, 955,613 and 955,614 are referred to.
GB852561A 1960-03-16 1961-03-08 New steroid compounds, processes for their preparation and conversion into compounds of utility in the production of substituted corticosteroids Expired GB955612A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR821557A FR1259501A (en) 1960-03-16 1960-03-16 Improvements made to the preparation of derivatives of pregnane 9alpha-halo 16 alpha-methylated

Publications (1)

Publication Number Publication Date
GB955612A true GB955612A (en) 1964-04-15

Family

ID=8727263

Family Applications (3)

Application Number Title Priority Date Filing Date
GB4717062A Expired GB955613A (en) 1960-03-16 1961-03-08 New steroid compounds and processes
GB4717162A Expired GB955614A (en) 1960-03-16 1961-03-08 New steroid compound and processes
GB852561A Expired GB955612A (en) 1960-03-16 1961-03-08 New steroid compounds, processes for their preparation and conversion into compounds of utility in the production of substituted corticosteroids

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB4717062A Expired GB955613A (en) 1960-03-16 1961-03-08 New steroid compounds and processes
GB4717162A Expired GB955614A (en) 1960-03-16 1961-03-08 New steroid compound and processes

Country Status (5)

Country Link
BE (1) BE601375A (en)
CH (1) CH395080A (en)
ES (1) ES265581A1 (en)
FR (1) FR1259501A (en)
GB (3) GB955613A (en)

Also Published As

Publication number Publication date
FR1259501A (en) 1961-04-28
ES265581A1 (en) 1961-07-01
BE601375A (en) 1961-09-15
CH395080A (en) 1965-07-15
GB955613A (en) 1964-04-15
GB955614A (en) 1964-04-15

Similar Documents

Publication Publication Date Title
GB902294A (en) Improvements in or relating to steroids and the manufacture thereof
GB955612A (en) New steroid compounds, processes for their preparation and conversion into compounds of utility in the production of substituted corticosteroids
GB929429A (en) Preparation of steroid compounds
GB1060793A (en) Improvements in or relating to steroids and the manufacture thereof
GB1045979A (en) Improvements in or relating to 5,10-seco-5,19-cyclo-10-fluoro-steroids
GB906443A (en) Steroid compounds
GB970482A (en) New 17-desoxy corticosteroids and processes for their preparation
US3646012A (en) Enamine salt protection of steroidal alpha beta-unsaturated ketones
GB1354164A (en) Steroido-oxazolines and processes for their production
GB934710A (en) New steroid compounds and processes for their production and conversion into substituted corticosteroids
GB935116A (en) New cyclopentanophenanthrene derivatives and processes for the production thereof
DE1518627C3 (en) Process for the dehydration of A-nor-B homosteroids
GB903049A (en) Steroid compounds, preparation thereof and compositions thereof
GB948545A (en) C-nor-steroids
GB1036276A (en) 7,16-dialkyl-pregnanes
AT333991B (en) PROCESS FOR MANUFACTURING NEW D-HOMO STEROIDS OF THE PREGNAN SERIES
NO132189B (en)
US3485854A (en) 16beta-methyl-9beta-fluoro-steroids
GB943951A (en) New steroid compounds, and processes for their preparation
GB994745A (en) Cyclopentanophenanthrene compounds and process for their production
GB944718A (en) New steroid compounds and processes for their preparation
GB877227A (en) Improvements in or relating to the production of steroid compounds, and the compounds thus produced
GB1077393A (en) New steroids
GB965572A (en) New steroid compounds and their formation
GB855800A (en) New cyclopentanophenanthrene derivatives and process for the production thereof