GB970586A - New steroid compounds and processes for their preparation - Google Patents

New steroid compounds and processes for their preparation

Info

Publication number
GB970586A
GB970586A GB28983/61A GB2898361A GB970586A GB 970586 A GB970586 A GB 970586A GB 28983/61 A GB28983/61 A GB 28983/61A GB 2898361 A GB2898361 A GB 2898361A GB 970586 A GB970586 A GB 970586A
Authority
GB
United Kingdom
Prior art keywords
pregn
ene
ketal
dione
hydroxy
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
GB28983/61A
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 GB970586A publication Critical patent/GB970586A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B22—CASTING; POWDER METALLURGY
    • B22C—FOUNDRY MOULDING
    • B22C9/00—Moulds or cores; Moulding processes
    • B22C9/02—Sand moulds or like moulds for shaped castings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055—Normal 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 at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • 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)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises pregn-4-en-3-one derivatives having the general formula: <FORM:0970586/C1/1> in which R2 represents the grouping =H(OY), R3 represents one of the groupings =H(CH2OY), =OH(CH2OY) or =(CH2OY)2, (where Y in the aforesaid groupings indicates an hydrogen atom or an acyl radical derived either from an organic carboxylic acid having 1-18 carbon atoms or from a mineral acid), and R4 represents the groups =H(OH) or the oxygen atom =O and their corresponding 3-ketal derivatives when R4 is the oxygen atom and R3 is H(CH2OY) or (CH2OY)2, a process for the production of 20, 21-dihydroxy -20- hydroxymethylene-pregn-4-ene-3,11-dione, in which the 21-hydroxy group is blocked by esterification prior to treatment thereof with an hydroxylating agent e.g. osmium tetroxide so as to yield upon saponification the desired 20,20-dihydroxy-20-hydroxymethylene-pregn-4-ene-3,11-dione and a process for the production of a 3-ketal of 20-hydroxymethylene-21-hydroxy-pregn-4-ene-3,11-dione and a 3-ketal of 20-bis-hydroxymethylene-21-hydroxy-pregn-4-ene-3,11-dione in which a 3-ketal of pregn-4-ene-3,11,21-trione is subjected to a Tollens condensation reaction with formaldehyde so as to yield a mixture of the desired 3-ketals. The 21-hydroxy-20-methylene-pregn-4-ene-3, 11 - dione starting material is formed by reacting a 3-ketal of pregn-4-ene-3,11,21-trione with formaldehyde to yield the 3-ketal of 20-methylene-pregn-4-ene-3,11,20-trione which is reduced e.g. with sodium borohydride to obtain the 3-ketal of 21-hydroxy-20-methylene-pregn-4-ene-3,11-dione, which is deketalized to obtain the desired 21-hydroxy-20-methylene-pregn-4-ene-3,11-dione. The 3-ketal of pregn-4-ene-3,11,21-trione starting material is in turn obtained by oxidation of the 3-ketal of 21-hydroxy-trans-pregna - 4, 17(20) - diene - 3, 11-dione so as to yield the corresponding 3-ketal of trans-pregna-4,17(20)-diene-3,11,21-trione which is then reduced. Any of the 3,11b -dihydroxy compounds obtained in the above processes may be oxidized to the corresponding 3-keto-11b -hydroxy compound e.g. with manganese dioxide. Specifications 970,587 and 970,588 are referred to.
GB28983/61A 1960-08-10 1961-08-10 New steroid compounds and processes for their preparation Expired GB970586A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR835529A FR1365261A (en) 1960-08-10 1960-08-10 Novel 3-oxo delta steroid compounds and method of preparation

Publications (1)

Publication Number Publication Date
GB970586A true GB970586A (en) 1964-09-23

Family

ID=8737231

Family Applications (3)

Application Number Title Priority Date Filing Date
GB7833/64A Expired GB970587A (en) 1960-08-10 1961-08-10 New steroid compounds and processes for their preparation
GB8251/64A Expired GB970588A (en) 1960-08-10 1961-08-10 New steroid compounds and processes for their preparation
GB28983/61A Expired GB970586A (en) 1960-08-10 1961-08-10 New steroid compounds and processes for their preparation

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB7833/64A Expired GB970587A (en) 1960-08-10 1961-08-10 New steroid compounds and processes for their preparation
GB8251/64A Expired GB970588A (en) 1960-08-10 1961-08-10 New steroid compounds and processes for their preparation

Country Status (4)

Country Link
CH (4) CH399456A (en)
ES (4) ES269699A1 (en)
FR (4) FR1365261A (en)
GB (3) GB970587A (en)

Also Published As

Publication number Publication date
FR1365261A (en) 1964-07-03
FR753M (en) 1961-08-21
ES269697A1 (en) 1961-11-16
FR754M (en) 1961-08-21
GB970588A (en) 1964-09-23
CH399455A (en) 1965-09-30
CH399454A (en) 1965-09-30
ES269698A1 (en) 1961-11-16
FR752M (en) 1961-08-21
ES269700A1 (en) 1961-11-16
GB970587A (en) 1964-09-23
ES269699A1 (en) 1961-11-16
CH401963A (en) 1965-11-15
CH399456A (en) 1965-09-30

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