GB1139505A - A process for the production of 17-‡-monoesters of 17-‡-hydroxy-20-keto-steroids - Google Patents

A process for the production of 17-‡-monoesters of 17-‡-hydroxy-20-keto-steroids

Info

Publication number
GB1139505A
GB1139505A GB1409165A GB1409165A GB1139505A GB 1139505 A GB1139505 A GB 1139505A GB 1409165 A GB1409165 A GB 1409165A GB 1409165 A GB1409165 A GB 1409165A GB 1139505 A GB1139505 A GB 1139505A
Authority
GB
United Kingdom
Prior art keywords
prepared
dione
hydrocarbonsulphonyloxy
triene
methyl
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
GB1409165A
Inventor
Niall Galbraith Weir
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo 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
Application filed by Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Priority to GB1409165A priority Critical patent/GB1139505A/en
Priority to US559083A priority patent/US3440252A/en
Priority to BE682890D priority patent/BE682890A/xx
Priority to DK321366A priority patent/DK118944B/en
Priority to FR66399A priority patent/FR1484277A/en
Priority to DE19661568690 priority patent/DE1568690A1/en
Priority to CH911066A priority patent/CH484890A/en
Priority to NL6608763A priority patent/NL6608763A/xx
Publication of GB1139505A publication Critical patent/GB1139505A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,139,505. 17α - Monoesters of 17α - hydroxy- 20-keto-steroids. GLAXO LABORATORIES Ltd. 14 June, 1966 [23 June, 1965], No. 14091/65. Heading C2U. 17α-acyloxy-20-keto-21-unsubstituted pregnanes are prepared by heating the corresponding 21-iodo compounds with a tertiary amine or a dialkyl sulphoxide, or by heating the corresponding 21-hydrocarbonsulphonyloxy or 21- bromo compounds under similar conditions but with the addition of a metal iodide. An inert solvent may also be present. The acyl group is derived from an alkyl, cycloalkyl, cycloalkylalkyl or aralkyl group. The 21-bromo starting material may be prepared from the 21-hydrocarbonsulphonyloxy compound and an alkali metal or alkaline earth metal bromide under anhydrous conditions in a solvent, and the 21- iodo starting material may be prepared similarly using an alkali metal or alkaline earth metal iodide, or it may be prepared from the 21-bromo compound using the same reagent. The process is particularly applicable to the preparation of 17α-monoesters of 21-deoxybetamethasone and 21 -deoxydexamethasone. 21-Hydrocarbonsulphonyloxy starting materials are prepared from the 21-ols and hydrocarbon sulphonyl halides. 21 - Hydroxy - 16 - # - methyl - 17α - propionyloxypregna - 1,4,9(11) - triene - 3,20 - dione is prepared by reacting 17α,21 - dihydroxy - 16# - methylpregna - 1,4,9(11) - triene - 3,20 - dione with triethyl orthopropionate to give 16#- methyl - 17α,21 - (1<SP>1</SP> - ethyl - 1<SP>1</SP> - ethoxymethylenedioxy) - pregna - 1,4,9(11) - triene - 3,20 - dione and hydrolysing this. 9α - Fluoro - 11#,21 - dihydroxy - 16α - methyl - 17α - propionyloxy - pregna - 1,4 - diene - 3,20 - dione is prepared similarly via dexamethasone 17α,21-ethyl orthopropionate.
GB1409165A 1965-06-23 1965-06-23 A process for the production of 17-‡-monoesters of 17-‡-hydroxy-20-keto-steroids Expired GB1139505A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
GB1409165A GB1139505A (en) 1965-06-23 1965-06-23 A process for the production of 17-‡-monoesters of 17-‡-hydroxy-20-keto-steroids
US559083A US3440252A (en) 1965-06-23 1966-06-21 Preparation of 21-deoxy steroids
BE682890D BE682890A (en) 1965-06-23 1966-06-21
DK321366A DK118944B (en) 1965-06-23 1966-06-22 Process for the preparation of 17α-acyloxysteroids from the pregnane series.
FR66399A FR1484277A (en) 1965-06-23 1966-06-22 Process for the preparation of 17alpha-acyloxy-steroids of the pregnan series
DE19661568690 DE1568690A1 (en) 1965-06-23 1966-06-23 Process for the production of steroid derivatives of the pregnancy series
CH911066A CH484890A (en) 1965-06-23 1966-06-23 Process for the preparation of 17-acyloxysteroids
NL6608763A NL6608763A (en) 1965-06-23 1966-06-23

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1409165A GB1139505A (en) 1965-06-23 1965-06-23 A process for the production of 17-‡-monoesters of 17-‡-hydroxy-20-keto-steroids

Publications (1)

Publication Number Publication Date
GB1139505A true GB1139505A (en) 1969-01-08

Family

ID=10034831

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1409165A Expired GB1139505A (en) 1965-06-23 1965-06-23 A process for the production of 17-‡-monoesters of 17-‡-hydroxy-20-keto-steroids

Country Status (5)

Country Link
BE (1) BE682890A (en)
CH (1) CH484890A (en)
DE (1) DE1568690A1 (en)
DK (1) DK118944B (en)
GB (1) GB1139505A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1510617A (en) * 1974-03-27 1978-05-10 Plurichemie Anstalt 16-methyl-9alpha-halo steroid esters and ethers and preparation thereof

Also Published As

Publication number Publication date
CH484890A (en) 1970-01-31
DE1568690A1 (en) 1970-03-26
BE682890A (en) 1966-12-21
DK118944B (en) 1970-10-26

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