GB1059643A - Improvements in or relating to processes for preparing corticoid compounds - Google Patents

Improvements in or relating to processes for preparing corticoid compounds

Info

Publication number
GB1059643A
GB1059643A GB2285964A GB2285964A GB1059643A GB 1059643 A GB1059643 A GB 1059643A GB 2285964 A GB2285964 A GB 2285964A GB 2285964 A GB2285964 A GB 2285964A GB 1059643 A GB1059643 A GB 1059643A
Authority
GB
United Kingdom
Prior art keywords
tribromo
diol
preparing
pregnene
moles
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
GB2285964A
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.)
Smith Kline and French Laboratories Ltd
Original Assignee
Smith Kline and French Laboratories Ltd
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
Priority claimed from US286959A external-priority patent/US3187025A/en
Priority claimed from US347399A external-priority patent/US3231568A/en
Application filed by Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Publication of GB1059643A publication Critical patent/GB1059643A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises (a) a process for preparing 5-pregnene-3b ,17a ,21 - triol - 20 - one - 21 - acylates by reaction of a 5-pregnene-3b ,17a -diol-20-one or its 3-acetate with two moles of bromine to form a mixture of 5,6,21-tribromo-3b ,17a -diol-20-ones, separating the 5a ,6b ,21-tribromo isomer by addition of a basic reagent, and treating this with two to three moles of a sodium, potassium or calcium iodide in the presence of a sodium, potassium or calcium carboxylate having up to 6 carbon atoms, and (b) 5a ,6b ,21 - tribromo - pregnane - 3b ,17a - diol-20-one and its 16a -hydroxy derivative. Unprecipitated 5,6,21-tribromo-compounds may be treated with zinc dust and acetic acid or with chromous chloride to regenerate the starting material. The products may be subsequently oxidized chemically or microbiologically, optionally by way of their 5,6-dibromo-derivatives, to their 3-keto-D 4-analogues.
GB2285964A 1963-06-11 1964-06-02 Improvements in or relating to processes for preparing corticoid compounds Expired GB1059643A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US286959A US3187025A (en) 1963-06-11 1963-06-11 Process for preparing compound s
US347399A US3231568A (en) 1964-02-26 1964-02-26 Processes and intermediates for preparing 16alpha-methyl corticoids

Publications (1)

Publication Number Publication Date
GB1059643A true GB1059643A (en) 1967-02-22

Family

ID=26964160

Family Applications (2)

Application Number Title Priority Date Filing Date
GB4066865A Expired GB1060354A (en) 1963-06-11 1964-06-02 Process for preparing 3-keto-í¸-steroids
GB2285964A Expired GB1059643A (en) 1963-06-11 1964-06-02 Improvements in or relating to processes for preparing corticoid compounds

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB4066865A Expired GB1060354A (en) 1963-06-11 1964-06-02 Process for preparing 3-keto-í¸-steroids

Country Status (6)

Country Link
BE (1) BE649163A (en)
CH (1) CH433286A (en)
DE (1) DE1235907B (en)
GB (2) GB1060354A (en)
IT (2) IT1048877B (en)
NL (2) NL151088B (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1060392B (en) * 1958-02-20 1959-07-02 Merck Ag E Process for the production of Reichsteins substance S
DE1060860B (en) * 1958-03-29 1959-07-09 Merck Ag E Process for the production of Reichsteins substance S

Also Published As

Publication number Publication date
NL6406306A (en) 1964-12-14
CH433286A (en) 1967-04-15
BE649163A (en) 1964-12-11
IT1048876B (en) 1980-12-20
DE1235907B (en) 1967-03-09
NL151088B (en) 1976-10-15
NL6406303A (en) 1964-12-14
IT1048877B (en) 1980-12-20
GB1060354A (en) 1967-03-01

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