GB735429A - Cyclopentanophenanthrene derivatives and improved process for making same - Google Patents

Cyclopentanophenanthrene derivatives and improved process for making same

Info

Publication number
GB735429A
GB735429A GB7570/52A GB757052A GB735429A GB 735429 A GB735429 A GB 735429A GB 7570/52 A GB7570/52 A GB 7570/52A GB 757052 A GB757052 A GB 757052A GB 735429 A GB735429 A GB 735429A
Authority
GB
United Kingdom
Prior art keywords
diol
dione
pregnene
acetate
trione
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
GB7570/52A
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 GB735429A publication Critical patent/GB735429A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0735429/IV (b)/1> (wherein X is >CH2 or >C = O, and R is the residue of a lower fatty acid having up to 6 carbon atoms), together with a process for the preparation of 21-esters of D 4-pregnene-17a : 21-diol-3 : 20-dione and D 4-pregnene-17a : 21-diol-3 : 11 : 20-trione, which comprises dibrominating an ester of allopregnane-17a : 21-diol-3 : 20-dione or -3 : 11 : 20-trione, treating the resultant 2 : 4-dibromo compound with an alkali metal iodide to yield the corresponding 2-iodo-D 4-pregnene derivative, and finally eliminating the iodine atom by use of a reducing agent, e.g. sodium bisulphite or chromous chloride. In examples (1) allopregnane - 3 : 20 - dione-17a : 21-diol 21-acetate is brominated in chloroform-acetic acid containing hydrogen bromide, yielding 2 : 4-dibromoallopregnane-3 : 20-dione-17a : 21-diol 21-acetate, which is refluxed with sodium iodide in acetone, and the resultant 2 - iodo - D 4 - pregnene - 3 : 20 - dione - 17a : 21-diol 21-acetate refluxed with aqueous sodium bisulphite and dioxan, giving D 4-pregnene-3 : 20-dione-17a : 21-diol 21-acetate; Allopregnane - 3 : 11 : 20 - trione - 17a : 21 - diol 21-acetate is treated as in (1) employing chromous chloride for the final reduction step, yielding D 4 - pregnene - 3 : 11 : 20 - trione - 17a : 21-diol 21-acetate. Specifications 698,952 and 712,058 are referred to.
GB7570/52A 1951-03-28 1952-03-24 Cyclopentanophenanthrene derivatives and improved process for making same Expired GB735429A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US735429XA 1951-03-28 1951-03-28

Publications (1)

Publication Number Publication Date
GB735429A true GB735429A (en) 1955-08-24

Family

ID=22114323

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7570/52A Expired GB735429A (en) 1951-03-28 1952-03-24 Cyclopentanophenanthrene derivatives and improved process for making same

Country Status (1)

Country Link
GB (1) GB735429A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2838532A (en) * 1955-07-01 1958-06-10 Upjohn Co 6-halo-17(20)-pregnenes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2838532A (en) * 1955-07-01 1958-06-10 Upjohn Co 6-halo-17(20)-pregnenes

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