GB931783A - New steroid compounds, and processes for their preparation - Google Patents

New steroid compounds, and processes for their preparation

Info

Publication number
GB931783A
GB931783A GB1934460A GB1934460A GB931783A GB 931783 A GB931783 A GB 931783A GB 1934460 A GB1934460 A GB 1934460A GB 1934460 A GB1934460 A GB 1934460A GB 931783 A GB931783 A GB 931783A
Authority
GB
United Kingdom
Prior art keywords
processes
subjecting
hydrogen
reduction
double bond
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
GB1934460A
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 GB931783A publication Critical patent/GB931783A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0007—Androstane derivatives not substituted in position 17
    • 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
    • C07J1/0003—Androstane derivatives
    • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • 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
    • C07J41/0016—Oximes
    • 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 compounds having the formula: <FORM:0931783/IV(a)/1> in which R1 reprents hydrogen or an acyl radical and X and Y are either both hydrogen or represent a 1,2-double bond, and processes for the production thereof by subjecting adrenosterone to nitrosation followed by reduction, e.g. with zinc and acetic acid, to form the corresponding 17-hydroxy-16-one-derivative, subjecting the product to the successive steps of esterification at the 17-position, protection at the 3-position, followed by reduction at the 11-position, e.g. with sodium borohydride, and saponification to remove the 17-ester group, ethynylating the 11-hydroxy product at the 16-position by means of acetylene in a basic medium and then regenerating the 3-ketone function to yield the desired 11b ,16b -dihydroxy-16a -ethynyl-androst-4-en-3-one, which can then, if desired, be converted by acylation into the corresponding 11-acyloxy compound and/or transforming into the corresponding compound having a 1,2-double bond, e.g. by means of Corynebacterium simplex. Specifications 788,895, 931,784 and 931,785 are referred to.
GB1934460A 1959-06-04 1960-06-01 New steroid compounds, and processes for their preparation Expired GB931783A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR796581A FR1344159A (en) 1959-06-04 1959-06-04 16-ethynyl teroid compounds of the androstane series and their production process

Publications (1)

Publication Number Publication Date
GB931783A true GB931783A (en) 1963-07-17

Family

ID=8715622

Family Applications (3)

Application Number Title Priority Date Filing Date
GB2024062A Expired GB931784A (en) 1959-06-04 1960-06-01 New steroid compounds and processes for their preparation
GB2024162A Expired GB931785A (en) 1959-06-04 1960-06-01 New steroid compounds, and processes for their preparation
GB1934460A Expired GB931783A (en) 1959-06-04 1960-06-01 New steroid compounds, and processes for their preparation

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB2024062A Expired GB931784A (en) 1959-06-04 1960-06-01 New steroid compounds and processes for their preparation
GB2024162A Expired GB931785A (en) 1959-06-04 1960-06-01 New steroid compounds, and processes for their preparation

Country Status (5)

Country Link
BE (1) BE591544A (en)
CH (1) CH421095A (en)
ES (1) ES258549A1 (en)
FR (1) FR1344159A (en)
GB (3) GB931784A (en)

Also Published As

Publication number Publication date
ES258549A1 (en) 1960-11-16
GB931785A (en) 1963-07-17
GB931784A (en) 1963-07-17
BE591544A (en) 1960-12-05
CH421095A (en) 1966-09-30
FR1344159A (en) 1963-11-29

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