GB715402A - 16, 17-dihydroxy-20-keto-pregnenes and-pregnapolyenes and method for producing them - Google Patents

16, 17-dihydroxy-20-keto-pregnenes and-pregnapolyenes and method for producing them

Info

Publication number
GB715402A
GB715402A GB3026/52A GB302652A GB715402A GB 715402 A GB715402 A GB 715402A GB 3026/52 A GB3026/52 A GB 3026/52A GB 302652 A GB302652 A GB 302652A GB 715402 A GB715402 A GB 715402A
Authority
GB
United Kingdom
Prior art keywords
pregnen
pregnadiene
pregnene
triol
acetate
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
GB3026/52A
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.)
KNUD ABILDGAARD ELLING
Original Assignee
KNUD ABILDGAARD ELLING
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 KNUD ABILDGAARD ELLING filed Critical KNUD ABILDGAARD ELLING
Publication of GB715402A publication Critical patent/GB715402A/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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention comprises pregnane derivatives characterized by hydroxyl groups in the 16 and 17 positions, a 20-keto group and one or more double bonds, (preferably one or two). They may contain additional hydroxyl and keto groups, and are prepared by the oxidation of a D 16 : 17-pregnen-20-one with osmium tetroxide. Compounds which contain additional double bonds which are not in conjugation with a keto group are initially brominated, the bromo derivative oxidized as before and the product then debrominated with, e.g. sodium iodide, zinc dust. In examples: (1) D 5 : 16-pregnadien - 3b - ol - 20 - one - 3 - acetate is brominated in ether and acetic acid to 5 : 6-dibromo - D 16 - pregnen - 3b - ol - 20 - one acetate, which on treatment with osmium tetroxide in ether and finally sodium sulphite and zinc dust gives D 5-pregnen-3b : 16 : 17-triol-20-one; (2) 16-dehydroprogesterone on treatment with osmium tetroxide, followed by aqueous alcoholic sodium sulphite yields D 4-pregnen - 16 : 17 - diol - 3 : 20 - dione. In the manner of (1) D 11:16-pregnadien-3b -ol-20-one is converted to D 11-pregnene-3b : 16 : 17-triol-20-one; D 5:16-pregnadiene-3 : 21-diol-20-one 3 : 21-diacetate to D 5-pregnene-3 : 16 : 17 : 21-tetrol-20-one; and D 5:11:16-pregnatrien-3-ol-20-one acetate to D 5:11-pregnadiene-3 : 16 : 17-triol-20-one. In the manner of (2), D 8(9):16-pregnadiene - 3 : 5 - diol - 11 : 20 - dione - 3-acetate is converted to D 8(9)-pregnene-3 : 5 : 16 : 17 - tetrol - 11 : 20 - dione; and 21-acetoxy - D 4:16 - pregnadiene - 3 : 11 : 20-trione to D 4-pregnene-16 : 17 : p 21-triol-3 : 11 : 20-trione.
GB3026/52A 1951-02-09 1952-02-05 16, 17-dihydroxy-20-keto-pregnenes and-pregnapolyenes and method for producing them Expired GB715402A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DK715402X 1951-02-09

Publications (1)

Publication Number Publication Date
GB715402A true GB715402A (en) 1954-09-15

Family

ID=8152424

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3026/52A Expired GB715402A (en) 1951-02-09 1952-02-05 16, 17-dihydroxy-20-keto-pregnenes and-pregnapolyenes and method for producing them

Country Status (1)

Country Link
GB (1) GB715402A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1083813B (en) * 1957-06-21 1960-06-23 American Cyanamid Co Process for the preparation of 12ª ‡ -halogen-4-pregnen-16ª ‡ -, 17ª ‡, 21-triol-3, 11, 20-triones and their 16ª ‡, 21-dialkanoates
US3288679A (en) * 1966-03-23 1966-11-29 Squibb & Sons Inc Steroidal compositions and method of use

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1083813B (en) * 1957-06-21 1960-06-23 American Cyanamid Co Process for the preparation of 12ª ‡ -halogen-4-pregnen-16ª ‡ -, 17ª ‡, 21-triol-3, 11, 20-triones and their 16ª ‡, 21-dialkanoates
US3288679A (en) * 1966-03-23 1966-11-29 Squibb & Sons Inc Steroidal compositions and method of use

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