GB878731A - New 6ª--chloro-steroids and process for the preparation thereof - Google Patents

New 6ª--chloro-steroids and process for the preparation thereof

Info

Publication number
GB878731A
GB878731A GB29334/59A GB2933459A GB878731A GB 878731 A GB878731 A GB 878731A GB 29334/59 A GB29334/59 A GB 29334/59A GB 2933459 A GB2933459 A GB 2933459A GB 878731 A GB878731 A GB 878731A
Authority
GB
United Kingdom
Prior art keywords
methyl
hydroxy
chloro
dione
dichloro
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
GB29334/59A
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 GB878731A publication Critical patent/GB878731A/en
Expired legal-status Critical Current

Links

Classifications

    • 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 6-chloro-16-methyl steroids of the formulae: - <FORM:0878731/IV (b)/1> wherein X=H(OH), H(O Acyl) or O, R represents hydrogen, and in the D 4-compounds R may also represent an acyl group, and C1-2 is saturated or unsaturated, and their preparation by reacting D 5-3b -hydroxy-16-methyl-20-keto pregnene or a functional derivative thereof with chlorine, introducing a hydroxy or acyloxy group at C17 into the resulting 5,6-dichloro steroid in a known manner, preferably by 20-enol acylation epoxidation of the 17(20) double bond and cleavage of the 17,20-oxide, oxidising the 3-hydroxy or acyloxy group (after saponification) to 3-keto, treating the product with a strong acid to yield the corresponding D 4-3-keto-6a -chloro compound and if required introducing a double bond between C1 and C2, preferably with selenium dioxide or with Corynebacterium simplex, and/or esterifying the 17-hydroxy group. Examples detail the preparation of 16b -methyl-5a ,6b -dichloro-pregnan-3b -ol-20-one, its 17(20)-enol 3,20-diacetate, the 17,20-epoxide, 16b -methyl-5a , 6b -dichloro-pregnan- 17a -ol- 3,20-dione, 6a -chloro-16b - methyl-D 4- pregnen- 17a -ol-3,20-dione and its 17-acetate, propionate, valerate, hexahydrobenzoate and b -phenylpropionate, the corresponding D 1,4-pregnadien-17a -ol-3,20-dione and analogous 16a -methyl compounds.
GB29334/59A 1958-09-17 1959-08-27 New 6ª--chloro-steroids and process for the preparation thereof Expired GB878731A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
MX878731X 1958-09-17

Publications (1)

Publication Number Publication Date
GB878731A true GB878731A (en) 1961-10-04

Family

ID=19743125

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29334/59A Expired GB878731A (en) 1958-09-17 1959-08-27 New 6ª--chloro-steroids and process for the preparation thereof

Country Status (1)

Country Link
GB (1) GB878731A (en)

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