GB920503A - New pregnane compounds and process for their manufacture - Google Patents

New pregnane compounds and process for their manufacture

Info

Publication number
GB920503A
GB920503A GB20522/59A GB2052259A GB920503A GB 920503 A GB920503 A GB 920503A GB 20522/59 A GB20522/59 A GB 20522/59A GB 2052259 A GB2052259 A GB 2052259A GB 920503 A GB920503 A GB 920503A
Authority
GB
United Kingdom
Prior art keywords
fluoro
hydroxy
diol
manufacture
pregnane 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
GB20522/59A
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.)
Syntex SA
Original Assignee
Syntex 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 Syntex SA filed Critical Syntex SA
Publication of GB920503A publication Critical patent/GB920503A/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
    • 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 compounds of the general formula <FORM:0920503/IV(a)/1> and esters thereof, (wherein X = F or Cl, X1 = H, F or Cl, Y = b -OH or = O, and R and R1 each represent a hydrogen atom or a saturated or unsaturated hydrocarbon radical or a heterocyclic radical) and in which there may be an additional double bond in the 1:2 position, together with their preparation by reacting the corresponding 16a ,17a -diol with an aldehyde or ketone RCOR1 in the presence of an acetalisation catalyst, e.g. copper sulphate, dry HCl, or HClO4. The 21-hydroxy group may be subsequently esterified or a 21ester hydrolysed with alkalis, e.g. sodium methoxide in methanol. Specified products include 16a ,17a - methylenedioxy - 6a - fluoro-D 4-pregnene-11b ,21-diol-3,20-dione, the 16a ,17a -(acetaldehyde)acetal of 6a -fluoro-16a -hydroxy-hydrocortisone and its 21-acetate, the 16a ,17a -acetonides of 6a -chloro-9a -fluoro-16-hydroxyprednisone and 6a ,9a -dichloro-16a -hydroxy cortisone, and the 16a ,17a -(methyl phenyl)ketal of 6a ,9a - difluoro-16a -hydroxyhydrocortisone and its 21-propionate. The invention is illustrated by eight examples. Specification 896,986 is referred to.
GB20522/59A 1958-06-13 1959-06-15 New pregnane compounds and process for their manufacture Expired GB920503A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
MX5124758 1958-06-13

Publications (1)

Publication Number Publication Date
GB920503A true GB920503A (en) 1963-03-06

Family

ID=19742851

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20522/59A Expired GB920503A (en) 1958-06-13 1959-06-15 New pregnane compounds and process for their manufacture

Country Status (3)

Country Link
CH (1) CH381680A (en)
FR (6) FR409M (en)
GB (1) GB920503A (en)

Also Published As

Publication number Publication date
FR526M (en) 1961-05-23
FR527M (en) 1961-05-23
CH381680A (en) 1964-09-15
FR528M (en) 1961-05-23
FR415M (en) 1961-04-17
FR525M (en) 1961-05-23
FR409M (en) 1961-04-10

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