GB982947A - Process for the manufacture of ª‡,ª‰-unsaturated ketosteroids - Google Patents

Process for the manufacture of ª‡,ª‰-unsaturated ketosteroids

Info

Publication number
GB982947A
GB982947A GB2417161A GB2417161A GB982947A GB 982947 A GB982947 A GB 982947A GB 2417161 A GB2417161 A GB 2417161A GB 2417161 A GB2417161 A GB 2417161A GB 982947 A GB982947 A GB 982947A
Authority
GB
United Kingdom
Prior art keywords
keto
group
carbon
general formula
double bond
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
GB2417161A
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.)
Bayer Pharma AG
Original Assignee
Schering AG
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 Schering AG filed Critical Schering AG
Publication of GB982947A publication Critical patent/GB982947A/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
    • 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
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/005—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

a ,b - Unsaturated - keto - steroids which contain a methyl group on the carbon atom in the b -position are prepared by heating a pyrazolinosteroid obtained by the diazomethane attachment to the carbon-carbon double bond of a D 1-3-keto- or D 16-20-keto-steroid which is not oxygen substituted at the 11-position at a temperature at or above 140 DEG C. in the presence of an organic base, for example a base having a dissociation constant less than 10-6 such as quinoline, isoquinoline, quinaldine, collidine, lutidine, N,N-dimethylaniline, aniline and mixtures thereof. Organic nitrogen bases having a boiling-point below 140 DEG C. such as pyridine, may be used in which case the reaction is carried out under pressure. The preferred starting compounds for the above process have the general formula <FORM:0982947/C2/1> wherein R represents <FORM:0982947/C2/2> or an alkyl group, X represents hydrogen or the methyl group and the hydroxy group may be functionally converted, or the general formula <FORM:0982947/C2/3> wherein R1 represents hydrogen or a free or functionally converted hydroxyl group and R2 represents <FORM:0982947/C2/4> , <FORM:0982947/C2/5> or =O, and may also contain a D 4- or D 5-double bond or D 4,6-doubl bonds. Specifications 926,372, 948,269 and 965,090 are referred to.
GB2417161A 1960-08-27 1961-07-04 Process for the manufacture of ª‡,ª‰-unsaturated ketosteroids Expired GB982947A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DESCH28392A DE1135900B (en) 1960-08-27 1960-08-27 Process for the production of ª ‡, ª ‰ -unsaturated ketosteroids, which have a 1- or 16-position methyl group on the ª ‰ carbon atom

Publications (1)

Publication Number Publication Date
GB982947A true GB982947A (en) 1965-02-10

Family

ID=7431096

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2417161A Expired GB982947A (en) 1960-08-27 1961-07-04 Process for the manufacture of ª‡,ª‰-unsaturated ketosteroids

Country Status (4)

Country Link
BE (1) BE607547A (en)
CH (1) CH401036A (en)
DE (1) DE1135900B (en)
GB (1) GB982947A (en)

Also Published As

Publication number Publication date
CH401036A (en) 1965-10-31
BE607547A (en) 1962-02-26
DE1135900B (en) 1962-09-06

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