GB1003085A - Process for the preparation of 10ª‰-methyl steroids - Google Patents

Process for the preparation of 10ª‰-methyl steroids

Info

Publication number
GB1003085A
GB1003085A GB790062A GB790062A GB1003085A GB 1003085 A GB1003085 A GB 1003085A GB 790062 A GB790062 A GB 790062A GB 790062 A GB790062 A GB 790062A GB 1003085 A GB1003085 A GB 1003085A
Authority
GB
United Kingdom
Prior art keywords
methyl
effected
group
methylation
protected
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
GB790062A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf 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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB1003085A publication Critical patent/GB1003085A/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
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Abstract

The invention comprises 10b -methyl-13b -n-propyl-gona-4,9(11)-dien-3-one derivatives of the general formula <FORM:1003085/C2/1> in which R represents the oxygen atom of a keto group, or a hydrogen atom and either a hydroxy group or an ester group derived from either a mineral acid or an organic carboxylic acid, and a process in which a 17b -acyloxy-13b -alkyl - 4,5 - seco - gon - 9 - ene - 3,5 - dione is protected at the 3-position, the 3-protected compound is subjected to methylation in the presence of an enolizing agent to effect methylation at the 10b -position and migration of the 9(10)-double bond to the 9(11)-position, the 3-protected keto group is liberated and the thus-freed ketonic compound is cyclized by alkali metal hydroxide into the corresponding 13b -alkyl - 17b - hydroxy - 10b - methyl - gona - 4,9(11)-dien-3-one. Protection of the 3-keto group may be effected by ketalization, e.g. with methyl-ethyl-dioxolan. Methylation may be effected with methyl iodide in the presence of potassium t.-amylate. Cyclization may be effected with potassium hydroxide in methanol. The 17b -hydroxy group in the so-obtained product may be oxidized to obtain the corresponding 17-keto compound with chromic anhydride in acetic acid, or esterified by an esterifying agent derived from either a mineral acid or an organic carboxylic acid. Specifications 979,892, 979,898 and 1,003,086 are referred to.
GB790062A 1961-03-01 1962-02-28 Process for the preparation of 10ª‰-methyl steroids Expired GB1003085A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR854250A FR1366728A (en) 1961-03-01 1961-03-01 New gonan derivatives and their preparation process

Publications (1)

Publication Number Publication Date
GB1003085A true GB1003085A (en) 1965-09-02

Family

ID=8749899

Family Applications (2)

Application Number Title Priority Date Filing Date
GB2877164A Expired GB1003086A (en) 1961-03-01 1962-02-28 Novel steroid compounds and their preparation
GB790062A Expired GB1003085A (en) 1961-03-01 1962-02-28 Process for the preparation of 10ª‰-methyl steroids

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB2877164A Expired GB1003086A (en) 1961-03-01 1962-02-28 Novel steroid compounds and their preparation

Country Status (6)

Country Link
BE (1) BE614522A (en)
BR (1) BR6236810D0 (en)
CH (1) CH406200A (en)
ES (1) ES275012A1 (en)
FR (1) FR1366728A (en)
GB (2) GB1003086A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL92952A (en) * 1990-01-03 1994-06-24 Teva Pharma R-enantiomers of n-propargyl-1-aminoindan compounds, their preparation and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
BE614522A (en) 1962-08-28
BR6236810D0 (en) 1973-05-24
ES275012A1 (en) 1962-05-01
FR1366728A (en) 1964-07-17
GB1003086A (en) 1965-09-02
CH406200A (en) 1966-01-31

Similar Documents

Publication Publication Date Title
GB1040554A (en) The manufacture of 3-keto-19-alkyl-steroids
Hassner et al. The Cleavage Reaction of 16-Oximino-17-keto Steroids1
GB1003085A (en) Process for the preparation of 10ª‰-methyl steroids
US2499247A (en) 2, 13 - dimethyldodecahydrophenanthrene hydroxy lactones and derivatives thereof
GB1158332A (en) New 7alpha-Methyl-19-Nor-Androstadienes and process for their Manufacture
US3032552A (en) 1-methyl steroids of the androstane series
GB1045979A (en) Improvements in or relating to 5,10-seco-5,19-cyclo-10-fluoro-steroids
US3357975A (en) 7alpha-mono-and dihalomethylestra-4, 9 (10)-dienes and 4, 9 (10), 11-trienes and their preparation
US2598648A (en) Process for the production of compounds of the androstane series
US3312720A (en) 3-desoxy-19-nor-androstenes
US3324152A (en) 1alpha-methyl-delta2-androstenes
GB974525A (en) Novel therapeutically-active steroid compounds, their preparation and incorporation into pharmaceutical compositions
US3004045A (en) delta5(10)-3,6-diketo androstenes
US3088952A (en) 1beta-cyano derivatives of delta4-3-keto pregnenes
US3260734A (en) 1, 1-ethylene-17alpha-alkyl-delta2-5alpha-androstene-17beta-ol compounds
GB855800A (en) New cyclopentanophenanthrene derivatives and process for the production thereof
GB1051580A (en)
GB1063816A (en) 10-a-methyl steroids
GB1085612A (en) New 16-alkyl pregnane derivatives and process for the preparation thereof
GB1019576A (en) Synthesis of steroids
GB1064078A (en) 5-a-pregnano-[3,2-c]pyrazole compounds
GB1003305A (en) Novel steroid compounds and their preparation
GB761526A (en) Steroid compounds
SE303486B (en)
GB982922A (en) New í¸-11ª‡-hydroxy-steroids and process for their manufacture